Hiroyuki Mizuguchi, Y Nariai, S Kato, T Nakano, T Kanayama, Yoshiki Kashiwada, Hisao Nemoto, Kazuyoshi Kawazoe, Yoshihisa Takaishi, Yoshiaki Kitamura, Noriaki Takeda and Hiroyuki Fukui : Maackiain is a novel antiallergic compound that suppresses transcriptional upregulation of the histamine H1 receptor and interleukin-4 genes., Pharmacology Research & Perspectives, Vol.3, No.5, e00166, 2015.
(要約)
Kujin contains antiallergic compounds that inhibit upregulation of histamine H1 receptor (H1R) and interleukin (IL)-4 gene expression. However, the underlying mechanism remains unknown. We sought to identify a Kujin-derived antiallergic compound and investigate its mechanism of action. The H1R and IL-4 mRNA levels were determined by real-time quantitative RT-PCR. To investigate the effects of maackiain in vivo, toluene-2,4-diisocyanate (TDI)-sensitized rats were used as a nasal hypersensitivity animal model. We identified (-)-maackiain as the responsible component. Synthetic maackiain showed stereoselectivity for the suppression of IL-4 gene expression but not for H1R gene expression, suggesting distinct target proteins for transcriptional signaling. (-)-Maackiain inhibited of PKCδ translocation to the Golgi and phosphorylation of Tyr(311) on PKCδ, which led to the suppression of H1R gene transcription. However, (-)-maackiain did not show any antioxidant activity or inhibition of PKCδ enzymatic activity per se. Pretreatment with maackiain alleviated nasal symptoms and suppressed TDI-induced upregulations of H1R and IL-4 gene expressions in TDI-sensitized rats. These data suggest that (-)-maackiain is a novel antiallergic compound that alleviates nasal symptoms in TDI-sensitized allergy model rats through the inhibition of H1R and IL-4 gene expression. The molecular mechanism underlying its suppressive effect for H1R gene expression is mediated by the inhibition of PKCδ activation.
Shin-Ichiro Kurimoto, Jian-Xin Pu, Han-Dong Sun, Yoshihisa Takaishi and Yoshiki Kashiwada : Coleifolides A and B, Two New Sesterterpenoids from the Aerial Parts of Scutellaria coleifolia H.Lév., Chemistry & Biodiversity, Vol.12, No.8, 1200-1207, 2015.
(要約)
Coleifolides A and B (1 and 2), two new sesterterpenoids with a -methyl-,-unsaturated--lactone moiety, were isolated from the aerial parts of Scutellaria coleifolia H.Lév. (Lamiaceae), together with three known compounds. Their structures were elucidated by NMR and MS examinations. Coleifolides A and B were concluded to be partially racemic compounds by the HPLC analysis using a chiral column or introduction of chiral derivatizing agents. The absolute configuration of the major isomer was determined by analyses of the CD spectrum as well as NMR data of (R)- and (S)-2-NMA derivatives. Coleifolides A and B are structurally similar to manoalide derivatives, previously isolated from marine sponges, and appear to be the first examples of this type of compounds being isolated from higher plants.
Shin-ichiro Kurimoto, Jian-Xin Pu, Han-Dong Sun, Yoshihisa Takaishi and Yoshiki Kashiwada : Acylated neo-clerodanes and 19-nor-neo-clerodanes from the aerial parts of Scutellaria coleifolia (Lamiaceae)., Phytochemistry, Vol.116, 298-304, 2015.
(要約)
Scutefolides A1 and A2, two acylated neo-clerodanes with a 19,18--lactone, scutefolides B1, B2 and C, three 19-nor-neo-clerodanes, together with scutefolides D, E1, E2 and F, four neo-clerodanes, were isolated from the EtOAc-soluble fraction of the aerial parts of Scutellaria coleifolia. Their structures were established on the basis of spectroscopic analysis. The absolute configurations of four of these compounds were elucidated by the CD exciton chirality method. Cytotoxic activities of scutefolides D-F against four cancer cell lines (KB, A549, HeLa, and MCF7) were also evaluated, but they were inactive.
Tsuyoshi Goto, Noritaka Hirazawa, Yoshihisa Takaishi and Yoshiki Kashiwada : Antiparasitic effect of matrine and oxymatrine (quinolizidine alkaloids) on the ciliate Cryptocaryon irritans in the red sea bream Pagrus major., Aquaculture, Vol.437, 339-343, 2015.
Chika Hashida, Naonobu Tanaka, Kazuyoshi Kawazoe, Kotarou Murakami, Han-Dong Sun, Yoshihisa Takaishi and Yoshiki Kashiwada : Hypelodins A and B, polyprenylated benzophenones from Hypericum elodeoides., Journal of Natural Medicines, Vol.68, No.4, 737-742, 2014.
(要約)
Two new polyprenylated benzophenones, hypelodins A (1) and B (2), were isolated from the aerial parts of the Chinese medicinal plant Hyperium elodeoides (Choisy). Their structures were elucidated on the basis of spectroscopic evidence. Hypelodin A (1) is a polyprenylated benzophenone having a tetrahydropyrane ring with three prenyl groups and one 4-methyl-1,3-pentadiene moiety, while hypelodin B (2) has a cage-like structure with a 6/6/5/7/6/5 hexacyclic ring system.
Hisako Sasaki, Hirofumi Shibata, Kiyoshi Imabayashi, Yoshihisa Takaishi and Yoshiki Kashiwada : Prenylated Flavonoids from the Stems and Leaves of Desmodium caudatum and Evaluation of Their Inhibitory Activity against the Film-Forming Growth of Zygosaccharomyces rouxii F51., Journal of Agricultural and Food Chemistry, Vol.62, No.27, 6345-6353, 2014.
(要約)
In order to provide scientific evidence for the relationship between the traditional usage, stems and leaves of Desmodium caudatum being used for protecting miso from spoilage, and its Japanese name (miso-naoshi), phytochemical study on the stems and leaves of this plant was carried out. Seven new prenylated flavonoids (1-3, 15-18), together with 19 known compounds (4-14, 19-26), were isolated, and the structures of new compounds were elucidated by extensive spectroscopic analyses. The minimum inhibitory concentrations (MICs) of 28 flavonoids, including 17 compounds (1, 2, 4, 5, 7-14, 20-22, 24, 25) isolated in this study and 11 flavonoids (27-37) previously isolated from the roots of this plant, against the film-forming yeast of Zygosaccharomyces rouxii F51 were determined. Fifteen compounds (2, 4, 5, 11, 12, 14, 21, 22, 25, 27, 28, 32-35) inhibited the film-forming growth of Z. rouxii F51 (MIC values, 7.8-62.5 g/mL), among which 2'',2''-dimethylpyran-(5'',6'':7,8)-5,2'-dihydroxy-4'-methoxy-(2R,3R)-dihydroflavonol (11) demonstrated potent inhibitory activity with an MIC value of 7.8 g/mL.
Shin-ichiro Kurimoto, Yoshihisa Takaishi, Fakhruddin Ali Ahmed and Yoshiki Kashiwada : Triterpenoids from the fruits of Azadirachta indica (Meliaceae)., Fitoterapia, Vol.92, 200-205, 2014.
(要約)
Four new triterpenoids, indicalilacols A-D (1-4), were isolated from the MeOH extract of the fruits of Azadirachta indica, including a new 19(109)abeo-tirucallane derivative, two new tirucallane-type triterpenoids, and a new euphane-type triterpenoid, along with three known tirucallane-type triterpenoids. Their structures were elucidated on the basis of spectroscopic analyses. The absolute configuration of 2 was elucidated by the chemical conversion of 2 into 21-oxo-melianodiol 24,25-acetonide. Compounds 2, 6-8 exhibited moderate cytotoxicity against three human cancer cell lines, including multidrug-resistant (MDR) cancer cells (KB-C2). Although compound 5 was not cytotoxic against any of the tested cancer cell lines, 5 showed cytotoxicity against KB-C2 cells in the presence of 2.5 M colchicine, suggesting that 5 might have an MDR-reversal effect.
Yoshiki Kashiwada, Yuka Omichi, Shin-ichiro Kurimoto, Hirofumi Shibata, Yoshiyuki Miyake, Tsukasa Kirimoto and Yoshihisa Takaishi : Conjugates of a secoiridoid glucoside with a phenolic glucoside from the flower buds of Lonicera japonica Thunb., Phytochemistry, Vol.96, 423-429, 2013.
(要約)
Secoiridoid glucosides, including two conjugates with a phenolic and two conjugates with a nicotinic acid derivative (3 and 4), together with seven known secoiridoid derivatives, were isolated from flower buds of Lonicera japonica. The structures were elucidated by spectroscopic analyses. Anti-influenza activities of six isolated compounds were also evaluated by plaque assay and neuraminidase inhibitory assay.
Yoshihiro Suyama, Shin-ichiro Kurimoto, Kazuyoshi Kawazoe, Kotarou Murakami, Han-Dong Sun, Shun-Lin Li, Yoshihisa Takaishi and Yoshiki Kashiwada : Rigenolide A, a new secoiridoid glucoside with a cyclobutane skeleton, and three new acylated secoiridoid glucosides from Gentiana rigescens Franch., Fitoterapia, Vol.91, 166-172, 2013.
(要約)
Rigenolide A (1), a new secoiridoid glucoside with a cyclobutane skeleton and three new acylated secoiridoid glucosides, 2'-(2,3-dihydroxybenzoyl)-gentiopicroside (2), 2'-(2,3-dihydroxybenzoyl)-swertiamarin (3), 3'-(2,3-dihydroxybenzoyl)-sweroside (4), along with two noriridoids (7 and 8) and two known secoiridoid glucosides (5 and 6), were isolated from Gentiana rigescens Franch. The structures of new compounds were elucidated by extensive spectroscopic analyses. The isolated compounds were evaluated for DPPH free-radical scavenging activity.
Takashi Ichiyanagi, Yoshiki Kashiwada, Yasuo Shida, Michiko Sekiya, Yoshihiko Hatano, Yoshihisa Takaishi and Yasumasa Ikeshiro : Structural elucidation and biological fate of two glucuronyl metabolites of pelargonidin 3-O--D-glucopyranoside in rats., Journal of Agricultural and Food Chemistry, Vol.61, No.3, 569-578, 2013.
(要約)
A high proportion of pelargonidin 3-O--D-glucopyranoside (Pg3G) is metabolized to glucuronides and excreted in mammal urine after ingestion of strawberry fruit, suggesting that these metabolites play important functional roles in vivo. The aim of the present study was to elucidate the structures and determine the biological fate of the two dominant metabolites of Pg3G in rats to enable an accurate discussion of the biological properties of anthocyanins. Authentic Pg3G was orally administered to rats. One pelargonidin monoglucuronide and three Pg3G-monoglucuronides (glucuronides of the glucoside) were identified together with intact Pg3G in both blood plasma and urine samples. The structures of the two dominant metabolites were elucidated as pelargonidin 3-O--D-glucuronide (Pg3GlcA) and pelargonidin 3-O--D-glucuronyl-(12)--D-glucoside by means of (1)H and (13)C nuclear magnetic resonance spectroscopy and heteronuclear multiple-bond connective spectroscopy. The bioavailability of Pg3G in its intact form was 0.31% of the orally administered dose, and 0.65% was absorbed in the Pg3GlcA form.
Hisako Sasaki, Yoshiki Kashiwada, Hirofumi Shibata and Yoshihisa Takaishi : Prenylated flavonoids from the roots of Desmodium caudatum and evaluation of their antifungal activity., Planta Medica, Vol.78, No.17, 1851-1856, 2012.
(要約)
Two new prenylated flavonoids (1, 4) and two new prenylated C-methyl-flavonoids (6, 7), together with four known flavonoids (2, 3, 5, 8), were isolated from the roots of Desmodium caudatum. The structures of the new compounds were elucidated by extensive spectroscopic analyses including 1D-, 2D-NMR and MS. The antifungal activities of five compounds (1, 2, 4, 6, 8) as well as nine flavonoids (9-17) previously isolated from this plant against Aspergillus niger, Penicillium sp., Rhizopus sp., and Trichophyton sp. were evaluated. Compound 6 showed potent antifungal activity against Trichophyton sp. with a minimum inhibitory concentration (MIC) value of 1.95 µg/mL.
Hisako Sasaki, Yoshiki Kashiwada, Hirofumi Shibata and Yoshihisa Takaishi : Prenylated flavonoids from Desmodium caudatum and evaluation of their anti-MRSA activity., Phytochemistry, Vol.82, 136-142, 2012.
(要約)
Seven prenylated flavonoids and a prenylated chromanochroman derivative, together with eight known flavonoids, were isolated from roots of Desmodium caudatum. The 15 structures were elucidated by extensive spectroscopic analyses. The antibacterial activity of many of other compounds was evaluated against methicillin-resistant Staphylococcus aureus (MRSA: COL and 5) by a disc diffusion method, and the minimum inhibitory concentrations (MICs) to MRSA were determined.
Tamotsu Tanaka, Ayaka Kassai, Mayumi Ohmoto, Katsuya Morito, Yoshiki Kashiwada, Yoshihisa Takaishi, Mai Urikura, Jun-ichi Morishige, Kiyoshi Satouchi and Akira Tokumura : Quantification of phosphatidic acid in foodstuffs using TLC-imaging technique, Journal of Agricultural and Food Chemistry, Vol.60, No.16, 4156-4161, 2012.
(要約)
Apical application of lysophosphatidic acid (LPA), a growth-factor-like phospholipid, was shown to prevent or restore gastrointestinal (GI) disorders, such as diarrhea and stomach ulcer, in experimental animals. Because LPA is formed from phosphatidic acid (PA) by the activity of digestive phospholipase A(2), PA is a potential component for dietary treatment of such GI disorders. Here, we quantified PA contained in 38 foodstuffs and 3 herbs by a thin-layer-chromatography-imaging technique. Vegetables belonging to Brassicaceae, such as cabbage leaves (700 nmol/g of wet weight) and Japanese radish leaves (570 nmol/g), contained higher amounts of PA than other foodstuffs. Amounts of PA in fruits, cereals, and starchy root vegetables were below 300 nmol/g. Animal foodstuffs contained low amounts of PA (<60 nmol/g). Interestingly, leaves of Mallotus japonicas, a Japanese edible herb used for treatment of stomach ulcer, had the highest PA (1410 nmol/g) among those examined. The data shown here will be useful for the development of dietary treatment for a damaged GI tract.
Yoshiki Kashiwada, Fakhruddin Ali Ahmed, Shin-ichiro Kurimoto, Sang-Yong Kim, Hirofumi Shibata, Toshihiro Fujioka and Yoshihisa Takaishi : New α-glucosides of caffeoyl quinic acid from the leaves of Moringa oleifera Lam., Journal of Natural Medicines, Vol.66, No.1, 217-221, 2012.
(要約)
Two new caffeoyl quinic acid α-glucosides, together with three known caffeoyl quinic acids and five known flavonoid glucosides, were isolated from the leaves of Moringa oleifera Lam. The structures of the new compounds were elucidated as 4-O-(4'-O-α-D-glucopyranosyl)-caffeoyl quinic acid (1) and 4-O-(3'-O-α-D-glucopyranosyl)-caffeoyl quinic acid (2) by spectroscopic analyses.
Shin-ichiro Kurimoto, Yoshiki Kashiwada, Kuo-Hsiung Lee and Yoshihisa Takaishi : Triterpenes and a triterpene glucoside from Dysoxylum cumingianum and their cytotoxicity., Phytochemistry, Vol.72, No.17, 2205-2211, 2011.
(要約)
Six triterpenes and a triterpene glucoside were isolated from the MeOH extract of the leaves of Dysoxylum cumingianum together with three known triterpenes. Their structures were elucidated by extensive spectroscopic analyses. In cytotoxicity assays against three human cancer cell lines, including a multi-drug resistant cancer cell line (KB-C2), compounds 1, 2 and 5 demonstrated significantly enhanced cytotoxicity against KB-C2 cells in the presence of 2.5 μM colchicine, as compared with those in the absence of colchicine. This result suggested that these triterpenes might show some MDR-reversing effects.
Kim Sang-Yong, Yoshiki Kashiwada, Kazuyoshi Kawazoe, Kotarou Murakami, Sun Han-Dong, Li Shun-Lin and Yoshihisa Takaishi : Spicachlorantins G-J, New Lindenane Sesquiterpenoid Dimers from the Roots of Chloranthus spicatus., Chemical & Pharmaceutical Bulletin, Vol.59, No.10, 1281-1284, 2011.
(要約)
Four new lindenane sesquiterpenoid dimers, spicachlorantins G-J (1-4), were isolated from the roots of Chloranthus spicatus together with seven known compounds, including chloramultilide A, shizukaol B, shizukaol D, shizukaol F, shizukaol P, chlorahololide D, and cycloshizukaol A. The planar structures of the new compounds were established by 1D-, 2D-NMR, and MS analyses. The absolute configurations of these compounds were determined by analyzing rotating Overhauser enhancement and exchange spectroscopy (ROESY) and circular dichroism (CD) spectra.
Shin-ichiro Kurimoto, Yoshiki Kashiwada, Susan L. Morris-Natschke, Kuo-Hsiung Lee and Yoshihisa Takaishi : Dyscusins AC, Three New Steroids From the Leaves of Dysoxylum cumingianum., Chemical & Pharmaceutical Bulletin, Vol.59, No.10, 1303-1306, 2011.
(要約)
Three new steroids dyscusins A-C (1-3), including a stigmastane-type sterol and two pregnanes, together with two known steroids were isolated from the leaves of Dysoxylum cumingianum (Meliaceae). Their structures were elucidated on the basis of extensive spectroscopic analyses. In a cytotoxicity assay, compound 1 showed ten-fold enhanced cytotoxicity against multi-drug resistant cancer cells (KB-C2) in the presence of 2.5 µM colchicine as compared with the absence of colchicine. This notable finding indicated that 1 possessed a multi-drug resistant reversal effect.
Ahmed Ali Fakhruddin, Kim Sang-Yong, Kurimoto Shin-ichiro, Sasaki Hisako, Hirofumi Shibata, Yoshiki Kashiwada and Yoshihisa Takaishi : Biflavonoids from Flowers of Butea monosperma (Lam.) Taub., Heterocycles, Vol.83, No.9, 2079-2089, 2011.
Yoshiki Kashiwada, Nishimura Kazuya, Kurimoto Shin-ichiro and Yoshihisa Takaishi : New 29-nor-cycloartanes with a 3,4-seco- and a novel 2,3-seco-structure from the leaves of Sinocalycanthus chinensis., Bioorganic & Medicinal Chemistry, Vol.19, No.9, 2790-2796, 2011.
(要約)
Eight new triterpenoids, including sinocalycanchinensins A-E (1-5) with a 3,4-seco-29-nor-cycloartane skeleton, sinocalycanchinensin F (6) possessing a novel 2,3-seco-29-nor-cycloartane skeleton, and 29-nor-cycloartanes, sinocalycanchinensins G and H (7 and 8), have been isolated from the leaves of Sinocalycanthus chinensis. Their structures were elucidated on the basis of spectroscopic examinations. The cytotoxicities of the isolated new triterpenes against a panel of human cancer cell lines, including multi-drug resistant (MDR) cancer cell lines, were also evaluated. Compound 5 demonstrated enhanced cytotoxicity against MDR KB cells in the presence of colchicine, although all the compounds showed moderate or no cytotoxicities.
Xiong Juan, Taniguchi Masatoshi, Yoshiki Kashiwada, Yamagishi Takashi and Yoshihisa Takaishi : Seven new dammarane triterpenes from the floral spikes of Betula platyphylla var. japonica., Journal of Natural Medicines, Vol.65, No.1, 217-223, 2011.
(要約)
Seven new dammarane-type triterpenoids, including two 20(S)-hydroxy-25-methoxy-dammar-23-enes (1 and 2), two 20(S),24(R)-epoxydammaranes (3 and 4), a cabralealactone (5), and two 20(S),25-epoxydammaranes (6 and 7), together with seven known triterpenes (8-14), were isolated from the floral spikes of Betula platyphylla var. japonica. The structures for all compounds were elucidated by the analyses of extensive spectroscopic data, as well as chemical examinations.
Kurimoto Shin-ichiro, Okasaka Mamoru, Yoshiki Kashiwada, K Olimjon Kodzhimatov and Yoshihisa Takaishi : Four new glucosides from the aerial parts of Mediasia macrophylla, Journal of Natural Medicines, Vol.65, No.1, 180-185, 2011.
(要約)
As part of our chemical studies on the medical plants in Uzbekistan aimed at searching for new drug leads, we have examined the aerial parts of Mediasia macrophylla. This has resulted in the isolation of four new glucosides, together with 30 known compounds. The structures of new compounds were elucidated as (1'S)-(4-hydroxyphenyl) ethane-1',2'-diol 2'-O-β-glucopyranoside (1), 3-(4'-methoxyphenyl)-propanol 1-O-β-glucopyranoside (2), 2-methoxy-3-hydroxy-5-(E)-propenyl-phenol 1-O-β-glucopyranoside (3), 1-O-angeloyl-β-glucopyranose (4), on the basis of spectral analysis.
Wen Zhang, Zhi Yao, Wen Yan Zhang, Xiang Xing Zhang, Yoshihisa Takaishi and Quan Hong Duan : Immunosuppressive sesquiterpenes from Buddleja daviddi, Planta Medica, Vol.76, No.16, 1882-1887, 2010.
(要約)
Six new sesquiterpenes, 2,6(12),10-humulatrien-7β-ol-1-one (1), 2 α-acetoxy-5α-methoxy-enantio-caryophylla-8(15)-en-3-one (2), 2α-acetoxy-5α-hydroxy-enantio-caryophylla-8(15)-en-3-one (3), 2α-acetoxy-4β,5α-hydroxy-enantio-caryophylla-8(15)-en-3-one ( 4), 2α-acetoxy-4β,5β-hydroxy-enantio-caryophylla-8(15)-en-3-one (5), 2β-acetoxy-4-caryophyllen-8β-ol-3-one (6), and nineteen known compounds were isolated from the ethanol extract of Buddleja daviddi. The structures were elucidated by spectroscopic methods. Compounds 8-11, 14, 16, 17, and 20 showed significant immunosuppressive activities, and 8-11 and 14 were cytotoxic on HeLa and L929 cell lines.
Jie Teng, Rong Zhang, Yan-Wen Zhang, Hong-Quan Duan and Yoshihisa Takaishi : A new labdanic norditerpene from Pinus sylvestris, Natural Product Research, Vol.24, No.17, 1587-1591, 2010.
(要約)
A new labdanic norditerpene and six known labdanic diterpenes were isolated from the petroleum ether extract of the needles of Pinus sylvestris. By spectroscopic methods, the isolated compounds were determined as 15-norpinifolic acid (1), pinifolic acid (2), 4-eplimbricataloic acid (3), monomethyl pinifolate (4), 18α-acetoxylabd-8(17)-en-15-oic acid (5), 2-pentenoic acid (6) and 3β-hydroxy-8(17),E-13-labdadien-15-oic acid (7), respectively. Compound 1 showed significant anti-tumour activity.
(キーワード)
Chromatography, High Pressure Liquid / Diterpenes / Drug Screening Assays, Antitumor / HeLa Cells / Humans / Magnetic Resonance Spectroscopy / Pinus / Spectrometry, Mass, Electrospray Ionization / Spectrophotometry, Ultraviolet / Spectroscopy, Fourier Transform Infrared
Xiong Juan, Yoshiki Kashiwada, Chen Chin-Ho, Qian Keduo, Morris-Natschke L. Susan, Lee Kuo-Hsiung and Yoshihisa Takaishi : Conjugates of Betulin Derivatives with AZT as Potent Anti-HIV Agents., Bioorganic & Medicinal Chemistry, Vol.18, No.17, 6451-6469, 2010.
(要約)
Fourteen novel conjugates of 3,28-di-O-acylbetulins with AZT were prepared as anti-HIV agents, based on our previously reported potent anti-HIV triterpene leads, including 3-O-acyl and 3,28-di-O-acylbetulins. Nine of the conjugates (49-53, 55, 56, 59, and 60) exhibited potent anti-HIV activity at the submicromolar level, with EC(50) values ranging from 0.040 to 0.098muM in HIV-1(NL4-3) infected MT-4 cells. These compounds were equipotent or more potent than 3-O-(3',3'-dimethylsuccinyl)betulinic acid (2), which is currently in Phase IIb anti-AIDS clinical trial.
Four new prenylated acylphloroglucinols, petiolins J-M (1-4), were isolated from aerial parts of Hypericum pseudopetiolatum var. kiusianum, and the structures were elucidated by spectroscopic data and a single-crystal X-ray diffraction analysis. Petiolin J (1) exhibited antimicrobial activity.
Hiroaki Yanagawa, Junji Terao, Eiji Takeda, Yoshihisa Takaishi, Yoshiki Kashiwada, Kazuyoshi Kawazoe, Fushitani Shuji, Koichiro Tsuchiya, Aiko Yamauchi, Sato Chiho and Minoru Irahara : Consultation clinics for complementary and alternative medicine at Japanese university hospitals: An analysis at Tokushima University Hospital, Experimental and Therapeutic Medicine, Vol.1, No.3, 481-483, 2010.
(要約)
Here, we report on a Consultation Clinic for Complementary and Alternative Medicine (CAM) which we established at Tokushima University Hospital in July of 2007 with the aim of providing person-to-person information on CAM, though not CAM therapy itself. In December of 2008, we received 55 applications for consultation, 37% concerning health foods, 37% Japanese herbal medicine (Kampo), and 26% various other topics. The consultants (nutritionists and pharmacists) communicated individually with 38 applicants; malignancies (26%) and cardiovascular disease (24%) were the main underlying concerns. To promote the quality of consultation, data was collected by means of focus group interviews concerning the perspective of the consultants. Safe and effective use of CAM requires a network of communication linking individuals, consultation teams, physicians, primary care institutions and university hospitals. To advance this goal, we plan to broaden the efforts described herein. Our findings indicate that the specific role of the consultation clinic in promoting the scientific use of CAM merits further study.
Shin-ichiro Kurimoto, Mamoru Okasaka, Yoshiki Kashiwada, Olimjon Kodzhimatov and Yoshihisa Takaishi : A new C14-polyacetylenic glucoside with an -pyrone moiety and four new C10-polyacetylenic glucosides from Mediasia macrophylla, Phytochemistry, Vol.71, No.5-6, 688-692, 2010.
(要約)
Polyacetylenic glucosides (1-5) were isolated from the MeOH extract of Mediasia macrophylla, and their structures were established by spectroscopic analyses. Compounds 2-4 were the first examples of C(10)-polyacetylenic glucosides found in the family Umbelliferae, while compound 1 was a unique polyacetylenic glucoside possessing an alpha-pyrone moiety.
Xiong Juan, Taniguchi Masatoshi, Yoshiki Kashiwada, Sekiya Michiko, Yamagishi Takashi and Yoshihisa Takaishi : Papyriferic Acid Derivatives as Reversal Agents of Multidrug Resistance in Cancer Cells., Bioorganic & Medicinal Chemistry, Vol.18, No.8, 2964-2975, 2010.
(要約)
Forty-one derivatives of papyriferic acid were prepared based on our previous finding that methyl papyriferate (3) showed potent reversing effect on cytotoxicity of colchicine against multidrug resistance (MDR) human cancer cells (KB-C2), and evaluated for their cytotoxicity and effect on reversing P-gp-mediated MDR against KB-C2 cells. 3-O-(Morpholino-beta-oxopropanoyl)-12beta-acetoxy-3alpha,25-dihydroxy-(20S,24R)-epoxydammarane (37) significantly increased the sensitivity of colchicine against KB-C2 cells by 185-fold at 5microg/mL (7.4microM), and the cytotoxicity of colchicine was recovered to nearly that of sensitive (KB) cells. The other several new amide derivatives also exhibited potent reversal activity comparable to or more potent than methyl papyriferate and verapamil.
Naonobu Tanaka, Takaaki Kubota, Yoshiki Kashiwada, Yoshihisa Takaishi and Jun'ichi Kobayashi : Petiolins F-I, benzophenone rhamnosides from Hypericum pseudopetiolatum var. kiusianum., Chemical & Pharmaceutical Bulletin, Vol.57, No.10, 1171-1173, 2009.
(要約)
Four new benzophenone-O-rhamnosides, petiolins F-I (1-4), were isolated from aerial parts of Hypericum pseudopetiolatum var. kiusianum, and the structures were elucidated by spectroscopic data and chemical means.
Naonobu Tanaka, Yoshiki Kashiwada, Sang-Yong Kim, Michiko Sekiya, Yasumasa Ikeshiro and Yoshihisa Takaishi : Xanthones from Hypericum chinense and their cytotoxicity evaluation., Phytochemistry, Vol.70, No.11-12, 1456-1461, 2009.
(要約)
A xanthonolignoid, 2-O-demethylkielcorin, and a phenylxanthone, chinexanthone A, were isolated from stems of Hypericum chinense together with four known xanthonolignoids and seven known xanthones. Their structures were established by spectroscopic analysis, as their optical properties and absolute stereochemistry determined. The cytotoxicities of the isolated xanthone derivatives as well as additional 32 xanthones against a panel of human cancer cell lines were also evaluated.
Naonobu Tanaka, Yoshiki Kashiwada, Sang Yong Kim, Waka Hashida, Michiko Sekiya, Yasumasa Ikeshiro and Yoshihisa Takaishi : Acylphloroglucinol, biyouyanagiol, biyouyanagin B, and related spiro-lactones from Hypericum chinense., Journal of Natural Products, Vol.72, No.8, 1447-1452, 2009.
(要約)
Biyouyanagiol (1), an acylphloroglucinol-related compound having a unique cyclopenta-1,3-dione moiety, was isolated from a Japanese traditional medicinal plant, Hypericum chinense, together with three new spiro-lactone-related derivatives, biyouyanagin B (2), 5,6-dihydrohyperolactone D (3), and 4-hydroxyhyperolactone D (4). Their structures were established on the basis of spectroscopic evidence. In a cytotoxicity assay against human cancer cell lines including multidrug-resistant (MDR) cancer cell lines, several compounds demonstrated enhanced cytotoxicity against MDR KB cells in the presence of colchicine.
Sang-Yong Kim, Yoshiki Kashiwada, Kazuyoshi Kawazoe, Kotarou Murakami, Han-Dong Sun, Shun-Lin Li and Yoshihisa Takaishi : Spicachlorantins A and B, New Dimeric Sesquiterpenes from the roots of Chloranthus spicatus., Phytochemistry Letters, Vol.2, No.3, 110-113, 2009.
Jun-Yi Hu, Zhi Yao, Ying-Qian Xu, Yoshihisa Takaishi and Hong-Quan Duan : Triterpenes from Astilbe chinensis., Journal of Asian Natural Products Research, Vol.11, No.3, 236-242, 2009.
(要約)
Six new triterpenes, 3beta,6beta-dihydroxyurs-12-en-27-oic acid (1), 3beta,6beta,24-trihydroxyurs-12-en-27-oic acid (2), 3beta,6beta,7alpha-trihydroxyurs-12-en-27-oic acid (3), 3beta-acetoxy-6beta-hydroxyurs-12-en-27-oic acid (4), 3beta,6beta,24-trihydroxyolean-12-en-27-oic acid (5), and 3beta,6beta,7alpha-trihydroxyolean-12-en-27-oic acid (6), were isolated from the rhizomes of Astilbe chinensis. Their structures were elucidated on the basis of 1D- and 2D-NMR analyses and HR-MS experiments. The isolated compounds exhibited significant cytotoxic activities against the SK-N-SH and HL-60 cell lines.
Jin-Bo Fang, Zhi Yao, Jia-Chun Chen, Yan-Wen Liu, Yoshihisa Takaishi and Hong-Quan Duan : Cytotoxic triterpene saponins from Alternanthera philoxeroides., Journal of Asian Natural Products Research, Vol.11, No.3, 261-266, 2009.
(要約)
Four new pentacyclic triterpene saponins, philoxeroidesides A-D (1-4) were isolated from the aerial parts of Alternanthera philoxeroides. Their structures were elucidated on the basis of 1D- and 2D-NMR experiments and MS analyses. Philoxeroidesides A-D (1-4) showed cytotoxic activities against SK-N-SH and HL60 cell lines.
Naonobu Tanaka, Yoshiki Kashiwada, Tatsuro Nakano, Hirofumi Shibata, Tomihiko Higuchi, Michiko Sekiya, Yasumasa Ikeshiro and Yoshihisa Takaishi : Chromone and chromanone glucosides from Hypericum sikokumontanum and their anti-Helicobacter pylori activities., Phytochemistry, Vol.70, No.1, 141-146, 2009.
(要約)
Chromone glucosides, takanechromones A-C (1, 2 and 5) and chromanone glucosides, named takanechromanones A and B (3 and 4), were isolated from the methanolic extracts of Hypericumsikokumontanum together with 27 known compounds. Their structures were established based on spectroscopic evidence. The isolated compounds and some chromone derivatives were assayed for antimicrobial activity against Helicobacter pylori and cytotoxicity against human cancer cell lines.
Freddy Ramos, Yoshihisa Takaishi, Yoshiki Kashiwada, Coralia Osorio, Carmenza Duque, Ricardo Acuna and Yoshinori Fujimoto : Ent-3,4-seco-labdane and ent-labdane diterpenoids from Croton stipuliformis (Euphorbiaceae), Phytochemistry, Vol.69, No.12, 2406-2410, 2008.
(要約)
From a methanolic extract of the leaves of Croton stipuliformis, three ent-3,4-seco-labdanes (1-3) and an ent-labdane (4) together with the known compounds 6-hydroxynidorellol (5), maravuic acid, and sitosterol were isolated and identified from their spectroscopic data. The absolute stereochemistry of compound 4 was determined by application of Mosher's method in the NMR tube.
Waka Hashida, Naonobu Tanaka, Yoshiki Kashiwada, Michiki Sekiya, Yasumasa Ikeshiro and Yoshihisa Takaishi : Tomoenones A-H, cytotoxic phloroglucinol derivatives from Hypericum ascyron, Phytochemistry, Vol.69, No.11, 2225-2230, 2008.
(要約)
Phloroglucinol derivatives tomoeones A-H (1-8) and three known compounds were isolated from leaves of Hypericum ascyron. Their structures were established based on spectroscopic analyses. They are all acylphloroglucinol derivatives possessing a spiro skeleton with geminal isoprenyl groups and a monoterpene moiety, and they are stereoisomers to each other at C-4 and C-13. They appear to be a class of phloroglucinol derivatives. Cytotoxicities of the isolated phloroglucinol derivatives against human tumor cell lines, including multidrug-resistant (MDR) cancer cell lines, were evaluated. Tomoeone F (6) demonstrated significant cytotoxicity against KB cells with an IC50 value of 6.2 microM. Compound 6 was also cytotoxic against MDR cancer cell lines (KB-C2 and K562/Adr), which was more potent than doxorubicin.
Chika Hashida, Naonobu Tanaka, Yoshiki Kashiwada, Makoto Ogawa and Yoshihisa Takaishi : Prenylated Phrologrucinol Derivatives from Hypericum perforatum var. angustifolium, Chemical & Pharmaceutical Bulletin, Vol.56, No.8, 1164-1167, 2008.
(要約)
Two new prenylated phloroglucinol derivatives and 15 known compounds were isolated from the aerial parts of Hypericum perforatum var. angustifolium. Their structures were determined on the basis of spectroscopic evidence.
Pu Liu, Zhi Yao, Wen Zhang, Yoshihisa Takaishi and Hong-Quan Duan : Novel Nortriterpenes from Phlomis umbrosa., Chemical & Pharmaceutical Bulletin, Vol.56, No.7, 951-955, 2008.
(要約)
We isolated 8 novel 28-noroleanane-derived spirocyclic triterpenoids with unusual skeleton structures, phlomisone (1), phlomistetraol A (2), phlomistetraol B (3), phlomistetraol C (4), phlomispentaol (5), phlomishexaol A (6), phlomishexaol B (7), and phlomisin (8), from the ethanol extract of Phlomis umbrosa rhizomes. Their structures were elucidated on the basis of spectroscopic methods, including 1D, 2D nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HR-MS), and X-ray analyses. Compounds 1-3, 5, and 7 exhibited positive cytotoxic activities against the carcinoma cell lines Hela and L929 in vitro, and these bioactive data suggested that the C-18 and C-21 positions had oxygenated functions that can improve the activity of the compound.
(キーワード)
Antineoplastic Agents, Phytogenic / Cell Line, Tumor / Humans / Magnetic Resonance Spectroscopy / Mass Spectrometry / Phlomis / Triterpenes
Two new phloroglucinol derivatives possessing chromane skeleton, petiolins A (1) and B (2), and a new phloroglucinol derivative containing a dihydrofuran ring, petiolin C (3), were isolated from aerial parts of Hypericum pseudopetiolatum var. kiusianum. The gross structures of 1-3 were elucidated by spectroscopic data, and the relative stereochemistry of 3 was elucidated by NOESY data. Petiolins A-C (1-3) showed modest cytotoxicity, while petiolin C (3) exhibited antifungal activity.
Mamoru Okasaka, Yoshiki Kashiwada, Olimjon K. Kodzhimatov, Ozodbek Ashurmetov and Yoshihisa Takaishi : Monoterpene glycosides from Paeonia hybrida, Phytochemistry, Vol.69, No.8, 1767-1772, 2008.
(要約)
Monoterpene glycosides (1-5, and 7), together with 14 known compounds, were isolated from the methanol extract of the roots of Paeonia hybrida. These compounds included a paeoniflorin-related glycoside with a hybrid structure of paeoniflorin and paeonovicinoside (1), a monoterpene glucoside biogenetically related to lactiflorin (2), a paeoniflorin-related monoterpene (3), arbiflorin-related monoterpenes (4 and 5), and a tymol-related monoterpene glycoside (7). Their structures were elucidated by extensive spectroscopic examinations.
(キーワード)
Benzoic Acids / Bridged Compounds / Glucosides / Glycosides / Magnetic Resonance Spectroscopy / Medicine, Chinese Traditional / Methanol / Molecular Structure / Paeonia / Plant Roots / Terpenes
Shunsuke Ishida, Mamoru Okasaka, Freddy A. Ramos, Yoshiki Kashiwada, Yoshihisa Takaishi, Olimjon K. Kodzhimatov and Ozodbek Ashumetov : New Alkaloid from the aerial parts of Condonopsis clematidea, Journal of Natural Medicines, Vol.62, No.2, 236-238, 2008.
(要約)
A new codonopsine-related alkaloid and 13 known compounds were isolated from the aerial parts of Codonopsis clematidea (Campanulaceae). The structure of the new compound was elucidated by two-dimensional nuclear magnetic resonance and other spectral examinations.
Yoshio Takeda, Maki Tomonari, Shihoko Arimoto, Toshiya Masuda, Hideaki Otsuka, Katsuyoshi Matsunami, Gisho Honda, Michiho Ito, Yoshihisa Takaishi, Fumiyuki Kiuchi, Olimjon K. Khodzhimatov and Ozodbek A. Ashurmetov : A new phenolic glucoside from an Uzbek medicinal plant, Origanum tyttanthum, Journal of Natural Medicines, Vol.62, No.1, 71-74, 2008.
(要約)
A new phenolic glucoside was isolated from the aerial parts of Origanum tyttanthum, an Uzbek medicinal plant, together with 12 known compounds. The structure of the new compound was elucidated as 4-O-beta-D-glucopyranosylbenzyl-3'-hydroxyl-4'-methoxybenzoate (1) based on the spectral and chemical evidence.
Michiko Sekiya, Yoshiki Kashiwada, Tomohiro Nabekura, Shuji Kitagawa, Takashi Yamagishi, Takako Yokozawa, Takashi Ichiyanagi, Yasumasa Ikeshiro and Yoshihisa Takaishi : Effect of Triterpenoids from the Floral Spikes of Betula platyphylla var. japonica on Glycoprotein Function, Planta Medica, Vol.73, No.15, 1558-1562, 2007.
(要約)
One of the major causes of multidrug resistance (MDR) in cancer cells is over-expression of P-glycoprotein (P-gp). We studied the effects of 20 triterpenes isolated from the floral spikes of Betula platyphylla var. japonica ( B. platyphylla) on P-gp function based on our previous finding that some of them showed MDR reversing effects. We evaluated accumulations and effluxes of rhodamine 123 as a P-gp substrate with P-gp over-expressing KB-C2 cells. Among the 20 triterpenes, compounds 3, 4, 8, 9, 13, 15, and 20 increased rhodamine 123 accumulations in KB-C2 cells, and three ( 8, 13, and 20) of them also inhibited efflux of rhodamine 123 out of cells. In addition, compounds 13 and 20 showed a weak inhibitory activity of P-gp ATPase. These results suggested that MDR reversing effects of compounds 13 and 20 are partly involved in inhibition of P-gp ATPase.
Wen Zhou, Hongru Li, Shufen Li, 高石 喜久, Hongquan Duan : Study on chromatographic fingerprint of extractive from Tripterygium wilfordii with supercritical carbon dioxide., China Journal of Chinese Materia Medica, Vol.32, No.8, 706-709, 2007年.
(要約)
To establish the chromatographic fingerprint of supercritical carbon dioxide extract of Tripterygium wilfordii. HPLC method was applied for quality assessment of T. Wilfordii, HPLC analysis was performed on Kromasil C18 (4. 6 mm x 250 mm, 5 microm) with the mixture of acetonitrile-1% per thousand H3PO4, as mobile phase in gradient mode. The samples were detected at UV of 267 nm with column temperature of 35 degrees C, analytic time was 80 min; Flow-rate was 1.0 mL x min(-1). The chromatographic fingerprint of ten batches of samples was determined, for establishing the chromatographic fingerprint of T. Wilfordii. Indicating 27 peaks in common, identified 21 peaks with chemical reference and HPLC-MS, and the HPLC fingerprint was established. The method is steady and accurate with a good repeatability and can be used as a quality control method for T. Wilfordii.
Kyoko Suzuki, Mamoru Okasaka, Yoshiki Kashiwada, Yoshihisa Takaishi, Gisho Honda, Michiho Ito, Yoshio Takeda, Olimjon K. Kodshimatov, Ozodbek Ashurmetov, Michiko Sekiya and Yasumasa Ikeshiro : Sesquiterpene Lactone from the Roots of Ferula varia and Their Cytotoxic Activity,, Journal of Natural Products, Vol.70, No.12, 1915-1918, 2007.
(要約)
The ethyl acetate-soluble fraction from a MeOH extract of the roots of Ferula varia gave six new sesquiterpene lactones (1-6) and five known sesquiterpenes (7-11). Their structures were established on the basis of spectroscopic evidence. The cytotoxic activities of 1-11 were evaluated against selected human cancer cell lines. Compound 4 showed significant selective cytotoxicity against multidrug-resistant cancer cells (KB-C2). The cytotoxicities of compounds 1, 3, 5, 8, and 11 against KB-C2 cells were enhanced in the presence of nontoxic concentrations of colchicine.
Chan Ming Li, Zhi Yao, Wen Yan Zhang, Yoshihisa Takaishi and Quan Hong Duan : A novel chalcone derivative from Onychium japonicum., Chinese Chemical Letters, Vol.18, No.7, 840-842, 2007.
Ying-Qian Xu, Zhi Yao, Jun-Yi Hu, Jie Teng, Yoshihisa Takaishi and Hong-Quan Duan : Immunosuppressive terpenes from Prinsepia utilis., Journal of Asian Natural Products Research, Vol.9, No.6-8, 637-642, 2007.
(要約)
Two new hemiterpenes, utililactone (1) and epiutililactone (2), along with nine known compounds (3-11), were isolated from the leaves of Prinsepia utilis. Their structures were elucidated on the basis of spectroscopic data. The isolated compounds showed significant immunosuppressive activities.
Pu Liu, Jie Teng, Yanwen Zhang, 高石 喜久, Hongyuan Duan : Chemical constituents from rhizome of Phlomis umbrosa., Yao Xue Xue Bao, Vol.42, No.4, 401-404, 2007年.
(要約)
Phlomis umbrosa is a traditional medicinal plant, distributed in the north of China. In the west of Hubei province, its roots were used in the treatment of the rheumatic diseases in Tujia nationality. To study the chemical constituents from the rhizome of Phlomis umbrosa chemical constituents were isolated from the plant by using repeated silica gel, toyopearl HW-40 and preparative HPLC chromatography. The structures of the compounds were elucidated on the basis of one and two dimensional NMR spectroscopic techniques and HRESI-MS. Ten compounds, 6"-syringyl-sesamoside (1), decaffeoylverbascoside (2), calcelarioside B (3), verbascoside (4), isoverbascoside (5), alyssonoside (6), sesamoside (7), shanzhiside methyl ester (8), 8-acetyl-shanzhiside methyl ester (9), 7-epiphlomiol (10) were isolated from P. umbrosa. Compound 1 is a new compound. Compounds 2-6 are isolated from this plant for the first time.
Yoshiki Kashiwada, Michiko Sekiya, Kimihisa Yamazaki, Yasumasa Ikeshiro, Toshihiro Fujioka, Takashi Yamagishi, Shuji Kitagawa and Yoshihisa Takaishi : Triterpenoids from the Floral Spikes of Betula platyphylla var. japonica and Their Reversing Activity against Multidrug-Resistant Cancer Cells, Journal of Natural Products, Vol.70, No.4, 623-627, 2007.
(要約)
Four new triterpenes, together with 16 known triterpenes, were isolated from the floral spikes of Betula platyphylla var. japonica in a search for compounds capable of reversing multidrug resistance in cancer cells. The structures of the new triterpenes were elucidated as 3,4-seco-olean-4(23),13(18)-dien-3-oic acid (1), 3,4-seco-urs-4(23),20(30)-dien-3-oic acid (2), 3-O-methylmalonylepiocotillol II (6), and 3-O-methylmalonylcabraleahydroxylactone (16) by spectroscopic examination. The cytotoxicity of the isolated triterpenes against human cancer cell lines as well as multidrug-resistant cancer cell lines was evaluated. Most of the isolated triterpenes showed very weak cellular toxicities. Although no discernible differences were found in the cytotoxicities for the tested compounds against sensitive and resistant cell lines, the cytotoxicities for several triterpenes against multidrug-resistant cancer cell lines (KB-C2 or K562/Adr) were enhanced in the presence of nontoxic concentrations of colchicine or doxorubicin. Compound 10 reversed the cytotoxicity of colchicine against KB-C2 cells at 8.1 microM and showed comparable potency to 5 microM verapamil.
(キーワード)
Antineoplastic Agents, Phytogenic / Betula / Colchicine / Drug Resistance, Multiple / Drug Resistance, Neoplasm / Drug Screening Assays, Antitumor / Humans / Japan / KB Cells / Molecular Structure / Triterpenes
Naonobu Tanaka and Yoshihisa Takaishi : Xanthones from Stems of Hypericum chinense, Chemical & Pharmaceutical Bulletin, Vol.55, No.1, 19-21, 2007.
(要約)
Six new xanthones, 4,6-dihydroxy-2,3-dimethoxyxanthone (1), 2,6-dihydroxy-3,4-dimethoxyxanthone (2), 6-hydroxy-2,3,4-trimethoxyxanthone (3), 3,6-dihydroxy-1,2-dimethoxyxanthone (4), 4,7-dihydroxy-2,3-dimethoxyxanthone (5), and 3,7-dihydroxy-2,4-dimethoxyxanthone (6) were isolated from the stems of Hypericum chinense, together with four known xanthones. Their structures were established based on spectroscopic studies.
(キーワード)
Chromatography, High Pressure Liquid / Hypericum / Magnetic Resonance Spectroscopy / Plant Stems / Spectrophotometry, Infrared / Xanthones
Lin Quan Yu, Quan Hong Duan, Yuan Wen Gao and Yoshihisa Takaishi : A new triterpene and a saponin from Centella asiatica, Chinese Chemical Letters, Vol.18, No.1, 62-64, 2007.
Pu Liu, Yoshihisa Takaishi and Quan Hong Duan : Two new phenylethanoid glycosides from the roots of Phlomis umbrosa, Chinese Chemical Letters, Vol.18, No.2, 155-157, 2007.
Y.-B. Liu, W. Jia, Z. Yao, Q. Pan, Yoshihisa Takaishi and H.-Q. Duan : Two eudesmane sesquiterpenes from Laggera pterodonta, Journal of Asian Natural Products Research, Vol.9, No.3, 233-237, 2007.
Mamoru Okasaka, Yoshihisa Takaishi, Yoshiki Kashiwada, K. Olimjon Kodzhimatov, Ozodbek Ashurmetov, J. Ai Lin, Mark L. Consentino and Kuo-Hsiung Lee : Terpenoids from Juniperus polycarpus var. seravschanica, Phytochemistry, Vol.67, No.24, 2635-2640, 2006.
(要約)
Two eudesmanes, two abietanes, two podocarpanes and other nine known compounds were isolated from the dried fruits of Juniperus polycarpus var. seravschanica. Their structures were established on the basis of analysis of spectroscopic evidence. Some of the isolated terpenoids showed antimalarial activity.
Yu Quan-Lin, Duan Hong-Quan, Yoshihisa Takaishi and Gao Wen-Yuan : A Novel Triterpene from Centella asiatica, Molecules, Vol.11, No.9, 661-665, 2006.
(要約)
A novel triterpene, 2alpha,3beta,20,23-tetrahydroxyurs-28-oic acid (1), was isolated from the aerial part of Centella asiatica. Its structure was elucidated by spectroscopic methods, including 2D-NMR spectra. It displayed no activity against Hela and A549 cell lines at concentrations of 10 and 30 microg/mL, respectively.
Masafumi Horiuch, Chihiro Murakami, Narihiko Fukamiya, Donglei Yu, Tzu-Hsuan Chen, F. Kenneth Bastow, De-Cheng Zhang, Yoshihisa Takaishi, Yasuhiro Imakura and Kuo-Hsiung Lee : Tripfordines A-C, Sesquiterpene Pyridine Alkaloids from Tripterygium wilfordii, and Structure Anti-HIV Activity Relationships of Tripterygium Alkaloids, Journal of Natural Products, Vol.69, No.9, 1271-1274, 2006.
(要約)
Three new sesquiterpene pyridine alkaloids, tripfordines A-C (1-3), were isolated from an ethanolic extract of the roots of Tripterygium wilfordii, along with eight known pyridine alkaloids, and tested for in vitro cytotoxic and anti-HIV activity. The structures of the new compounds were established on the basis of spectroscopic data interpretation. Anti-HIV structure-activity relationships (SAR) for this compound type are proposed on the basis of the screening results from the newly isolated compounds and prior data of known sesquiterpene pyridine alkaloids. The position of a carboxyalkyl chain on the pyridine moiety was not critical since both 2'- and 4'-substituted compounds exhibited high anti-HIV activity (EC(50) 0.1 microg/mL). In contrast, a hydroxy group at C-8' (carboxypropyl side chain) or C-9' (carboxybutyl side chain) was found to affect anti-HIV activity.
Naonobu Tanaka and Yoshihisa Takaishi : Xanthones from Hypericum chinense, Phytochemistry, Vol.67, No.19, 2146-2151, 2006.
(要約)
Six xanthones, 1,3,7-trihydroxy-2-(2-hydroxy-3-methyl-3-butenyl)-xanthone (1), 1,7-dihydroxy-2,3-[2''-(1-hydroxy-1-methylethyl)-dihydrofurano]-xanthone (2), 1,3,7-trihydroxy-5-methoxyxanthone (3), 1,7-dihydroxy-5,6-dimethoxyxanthone (4), 4,5-dihydroxy-2,3-dimethoxyxanthone (5), 1,3-dihydroxy-2,4-dimethoxyxanthone (6) and 21 known xanthones were isolated from the leaves and stems of Hypericum chinense. Their structures were established based on spectroscopic studies.
Hiroyuki Nakagawa, Yoshihisa Takaishi, Naonobu Tanaka, Koichiro Tsuchiya, Hirofumi Shibata and Tomihiko Higuti : Chemical Constituents from the Peels of Citrus sudachi, Journal of Natural Products, Vol.69, No.8, 1177-1179, 2006.
(要約)
A methanol extract of the peels of Citrus sudachi gave five new compounds (1-5) and 27 known compounds. The structures were elucidated on the basis of spectroscopic evidence. Several of these compounds were assayed for antimicrobial activity against methicillin-resistant Staphylococcus aureus and Helicobacter pylori, and sudachitin (6) and 3'-demethoxysudachitin (7) were the most active.
Freddy A. Ramos, Yoshihisa Takaishi, Kazuyoshi Kawazoe, Coralia Osorio, Carmenza Duque, Ricardo Acuna, Yoshinori Fujimoto, Mtsunobu Sato, Masato Okamoto, Tetsuya Oshikawa and S. U. Ahmed : Immunosuppressive diacetylenes, ceramides and cerebrosides from Hydrocotyle leucocephalata, Phytochemistry, Vol.67, No.11, 1143-1150, 2006.
(要約)
Three C-17 diacetylenic compounds (1-3), one monoterpenoid (4), seven ceramides (leucoceramides A-G, 5a-g), six cerebrosides (leucocerebrosides A-F, 6a-f) and nine known compounds were isolated from the methanolic extract of Hydrocotyle leucocephala. Their structures were established by spectroscopic methods. The isolated compounds 1-3, 5a-g, 6a-f and 7 were shown to be active in the lipopolysaccharide (LPS) induced cytokine production assay for IL-10, IL-12, and TNF-alpha.
Y.-B. Liu, W. Jia, W.-Y. Gao, A.-H. Zhao, Y.-W. Zhang, Yoshihisa Takaishi and H.-Q. Duan : Two eudesmane sesquiterpenes from Laggera pterodonta, Journal of Asian Natural Products Research, Vol.8, No.4, 303-307, 2006.
(要約)
The phytochemical study of the aerial parts of Laggera pterodonta afforded two new eudesmane sesquiterpenes, 3alpha,4beta,11-trihydroxyenantioeudesmane (pterodontriol E) (1) and 4beta,8beta,11-trihydroxyenantioeudesmane (pterodontriol F) (2), along with seven known compounds. Their structures were elucidated on the basis of spectroscopic data.
F.A. Ramos, Yoshihisa Takaishi, M. Shirotori, Y. Kawaguchi, Koichiro Tsuchiya, Hirofumi Shibata, Tomihiko Higuti, T. Tadokoro and M. Takeuchi : Antibacterial and Antioxidant Activities of Quercetin Oxidation Products from Yellow Onion (Alliu cepa) Skin, Journal of Agricultural and Food Chemistry, Vol.54, No.10, 3551-3357, 2006.
(要約)
Four new quercetin-derived oxidation products (1-4) and lunularin-4-O-beta-D-glucoside (5) were isolated from a water extract of onion (Allium cepa) skin, together with 17 other known compounds. Antibacterial assays for the isolated compounds showed that 2-(3,4-dihydroxyphenyl)-4,6-dihydroxy-2-methoxybenzofuran-3-one (1) presented selective activity against Helicobacter pylori strains and 3-(quercetin-8-yl)-2,3-epoxyflavanone (4) showed antibacterial activity against MRSA and H. pylori strains at the same time that it increased susceptibility of MRSA to beta-lactams. Evaluation of antioxidant activity against DPPH for the isolated compounds showed that the new derivative compounds (1-4) and 2,5,7,3',4'-pentahydroxy-3,4-flavandione (6) are more active than quercetin.
J.Y. Hu, Z. Yao, J. Teng, Yoshihisa Takaishi and H.Q. Duan : Two New Triterpenes from Astilbe chinensis, Chinese Chemical Letters, Vol.17, No.5, 628-630, 2006.
Jeong-Yong Cho, Jae-Hak Moon, Hye-Kyung Kim, Seung-Jin Ma, Seon-Jae Kim, Mi-Young Jang, Kazuyoshi Kawazoe, Yoshihisa Takaishi and Keun-Hyung Park : Isolation and structural elucidation of antimicrobial compounds from buckwheat hull, Journal of Microbiology and Biotechnology, Vol.16, No.4, 538-542, 2006.
K Kondo, Yoshihisa Takaishi, Hirofumi Shibata and Tomihiko Higuti : ILSMRs (intensifier of β-lactam-susceptibility in methicillin-resistant Staphylococcus aureus) from Tara [Caesalpinia spinosa (Molina) Kuntze], Phytomedicine, Vol.13, No.3, 209-212, 2006.
(要約)
Four quinic acid gallates were isolated from the dried pods of Tara [Caesalpinia spinosa (Molina) Kuntze]. These compounds intensified the susceptibility of methicillin-resistant Staphylococcus aureus (MRSA) to oxacillin. 3,4,5-Tri-O-galloylquinic acid methyl ester (2) was the most effective compound of them.
J.Y. Hu, W. Qiao, Yoshihisa Takaishi and H.Q. Duan : A New Hemiterpene Derivative From Pyinsepia utilis, Chinese Chemical Letters, Vol.17, No.2, 198-200, 2006.
Xiao-Dong Wang, Wei Jia, Wen-Yuan Gao, Rong Zhang, Yan-Wen Zhang, Jun Zhang, Yoshihisa Takaishi and Hong-Quan Duan : Terpene alkaloids from Tripterygium wilfordii, Journal of Asian Natural Products Research, Vol.7, No.5, 755-759, 2005.
(要約)
Two new sesquiterpene alkaloids, 1beta-hydroxy-2beta,5alpha,11-triacetoxy-7beta-nicotinoyl-8beta-benzoyl-dihydroagarofuran, and 1beta,5alpha,11-triacetoxy-7beta-nicotinoyl-8beta-benzoyl-dihydroagarofuran were isolated from the xylem of Tripterygium wilfordii, together with six known compounds. Their structures were elucidated on the basis of spectroscopic studies.
Kazuyoshi Kawazoe, Mami Tabata, Kotaro Murakami and Yoshihisa Takaishi : A Novel Drimane-Type Sesquiterpene from Limonium wrightii, Natural Medicines, Vol.59, No.4, 186-188, 2005.
(要約)
A new drimane-type sesquiterpene, (2S^*,6R^*)-2,6-dihydroxyisodrimenin (1) was isolated from the aerial part of a subtropical plant, Limonium wrightii (HANCE) KUNTZE (Plumbaginaceae), along with drimenin (3), hovetrichoside C (10) and six known tyramides (4-9), and the structures were elucidated by spectroscopic methods. Compound 1 is the first example of a 2-hydroxyisodrimenin-type sesquiterpene.
Wataru Sakane, Noriyuki Hara, Yoshinori Fujimoto, Yoshihisa Takaishi, Ricardo Acuña, Coralia Osorio and Carmenza Duque : Cupaniol, a New Branched Polyprenol, from Cupania latifolia, Chemical & Pharmaceutical Bulletin, Vol.53, No.8, 1037-1039, 2005.
(要約)
A new branched polyprenol, designated cupaniol, has been isolated from the methanol extract of the leaves of Cupania latifolia (Sapindaceae). The structure was determined to be (2E,6E,12E,16E)-3,7,13,17,21-pentamethyl-10-(1-methylethenyl)-2,6,12,16,20-docosapentaen-1-ol on the basis of spectral analysis and conversion to a known compound.
Naonobu Tanaka, Mamoru Okasaka, Youko Ishimaru, Yoshihisa Takaishi, Mitsunobu Sato, Masato Okamoto, Tetsuya Oshikawa, Sharif Uddin Ahmed, L. Mark Consentino and Kuo-Hsiung Lee : Biyouyanagin A, an Anti-HIV Agent from Hypericum chinense L. var. salicifolium, Organic Letters, Vol.7, No.14, 2997-2999, 2005.
(要約)
[structure: see text] A structurally unique hydrophobic compound, biyouyanagin A, was isolated from the MeOH extract of the leaves of Hypericum chinense L. var. salicifolium. The structure of biyouyanagin A was elucidated on the basis of spectroscopic evidence. Biyouyanagin A showed a significant activity against HIV and inhibited cytokine production.
Xiaodong Wang, Wenyuan Gao, Zhi Yao, Shaoyu Zhang, Yanwen Zhang, Yoshihisa Takaishi and Hongquan Duan : Immunosuppressive Sesquiterpenes from Tripterygium wilfordii, Chemical & Pharmaceutical Bulletin, Vol.53, No.6, 607-610, 2005.
(要約)
Five new sesquiterpenes, 1beta-furanoyl-2beta,3alpha,7alpha,8beta,11-pentaacetoxy-4alpha,5alpha-dihydroxy-dihydroagarofuran (1), 1beta,2beta,3alpha,5alpha,7beta,8beta,11-heptaacetoxy-dihydroagarofuran (2), 1beta-furanoyl-2beta,3alpha,7alpha,8beta,11-pentaacetoxy-5alpha-hydroxy-dihydroagarofuran (3), 1beta,7beta,8alpha-triacetoxy-2beta-furanoyl-4alpha-hydroxy-11-isobutyryloxy-dihydroagarofuran (4), and 1beta-nicotinoyl-2beta,5alpha,7beta-triacetoxy-4alpha-hydroxy-11-isobutyryloxy-8alpha-furanoyl-dihydroagarofuran (5), were isolated from the xylem of Tripterygium wilfordii, together with a known compound (6). Their structures were elucidated on the basis of spectroscopic studies. Compounds 2-5 showed significant immunosuppressive activities.
Toshimasa Ochi, Hirofumi Shibata, Tomihiko Higuti, Ko-hei Kodama, Takenori Kusumi and Yoshihisa Takaishi : Anti-Helicobacter pylori Compounds from Santalum album, Journal of Natural Products, Vol.68, No.6, 819-824, 2005.
(要約)
Six new sesquiterpenes, (Z)-2beta-hydroxy-14-hydro-beta-santalol (1), (Z)-2alpha-hydroxy-albumol (2), 2R-(Z)-campherene-2,13-diol (3), (Z)-campherene-2beta,13-diol (4), (Z)-7-hydroxynuciferol (5), and (Z)-1beta-hydroxy-2-hydrolanceol (6), together with five known compounds, (Z)-alpha-santalol (7), (Z)-beta-santalol (8), (Z)-lanceol (9), alpha-santaldiol (10), and beta-santaldiol (11), were isolated from Santalum album, by using bioassay-guided fractionation for Helicobacter pylori. The structures were determined by extensive NMR studies. The absolute configuration of compound 3 was determined by a modified Mosher method. The crude extracts as well as the isolated compounds showed antibacterial activity against H. pylori. Especially, compounds 7 and 8 have strong anti-H. pylori activities against a clarithromycin-resistant strain (TS281) as well as other strains.
Adriana Bonilla, Carmenza Duque, Cristina Garzón, Yoshihisa Takaishi, Kazutaka Yamaguchi, Noriyuki Hara and Yoshinori Fujimoto : Champanones, yellow pigments from the seeds of champa (Campomanesia lineatifolia), Phytochemistry, Vol.66, No.14, 1736-1740, 2005.
(要約)
Chemical investigation of the methanol extract of the seeds of Campomanesia lineatifolia Ruiz and Pav. (Myrtaceae) led to the isolation of two new beta-triketone type compounds, named champanones A (1) and B (2), together with the known 2,3-dihydro-5-hydroxy-6,8,8-trimethyl-2-phenyl-4H-1-benzopyran-4,7(8H)-dione (champanone C) (3). The structures of 1 and 2 were determined to be 2,2,4,4-tetramethyl-6-(1-oxo-3-phenylprop-2-enyl) cyclohexane-1,3,5-trione (occurs as an enol form) and 2,2,4-trimethyl-6-(1-oxo-3-phenylprop-2-enyl)cyclohexane-1,3,5-trione (occurs as an enol form), respectively, by means of spectroscopic analysis. The three compounds showed mild antimicrobial activity.
Ai Suga, Yoshihisa Takaishi, Hiroyuki Nakagawa, Tadashi Iwasa, Mitsunobu Sato and Masato Okamoto : Chemical Constituents from Fruits and Seeds of Myrica rubra (Myricaceae), Natural Medicines, Vol.59, No.2, 70-75, 2005.
(要約)
Two dammarane-type triterpenes and one steroid were isolated from the fruits of Myrica rubra and one furofran lignan was isolated from the seeds of M.rubra. Their structures were determined on the basis of spectral evidence. In addition, 16 known compounds were assayed for LPS-induced cytokine production.
Toshimasa Ochi, Yoshihisa Takaishi, Hirofumi Shibata, Higuti Tomihiko and Mai Kataoka : Chemical Constituents of Capsicum annuum L var. angulosum, and Anti Helicobacter pylori Activity, Natural Medicines, Vol.59, No.2, 76-84, 2005.
(要約)
One new and 47 known compounds were isolated from the fruits and the stems of Capsicum annuum var. angulosum. The structures of the isolated new and known compounds were determined by extensive NMR studies and compared with a reference value of the spectral data. Furthermore, antibacterial activity against Helicobacter pylori of the isolated 41 compounds was measured.
(キーワード)
Capsicum annuum var. angulosum / Helicobacter pylori / antibacterial activity
Takaaki Sagawa, Yoshihisa Takaishi, Yoshinori Fujimoto, Carmenza Duque, Coralia Osorio, Freddy Ramos, Garzon Cristina, Mitsunobu Sato, Masato Okamoto, Tetsuya Oshikawa and Sharif Uddin Ahmed : Cyclobutane Dimers from the Colombian Medicinal Plant Achyrocline bogotensis, Journal of Natural Products, Vol.68, No.4, 502-505, 2005.
(要約)
Five cyclobutane dimers, achyrodimers A-E (1-5), along with 11 known compounds were isolated from the methanol extract of the Colombian medicinal plant Achyrocline bogotensis. Their structures were elucidated by spectroscopy. Several of these compounds were screened for cytokine-inducing activity in human peripheral blood mononuclear cells.
Nozomi Komakine, Yoshihisa Takaishi, Gisho Honda, Michiho Ito, Yoshio Takeda, Olimjon K. Kodzhimatov and Ozodbek Ashurmetov : Indole alkaloids from Rheum maximowiczii, Natural Medicines, Vol.59, No.1, 45-48, 2005.
(要約)
A new indol alkaloid along with 17 known compounds were isolated from the seeds of Rheum maximowiczii Losinsk (Polygonaceae). Its structure was elucidated from the 2D NMR and other spectral evidence. Several of these compounds were screened for cytokine-inducing activity on human peripheral blood mononuclear cells. The cytokine-inducing activity of some of the isolated compounds is also reported.
Hirofumi Shibata, Kyoko Kondo, Ryo Katsuyama, Kazuyoshi Kawazoe, Youichi Sato, Kotaro Murakami, Yoshihisa Takaishi, Naokatu Arakaki and Tomihiko Higuti : Alkyl Gallates, Intensifiers of ß-Lactam Susceptibility in Methicillin-Resistant Staphylococcus aureus, Antimicrobial Agents and Chemotherapy, Vol.49, No.2, 549-555, 2005.
(要約)
We found that ethyl gallate purified from a dried pod of tara (Caesalpinia spinosa) intensified beta-lactam susceptibility in methicillin-resistant and methicillin-sensitive strains of Staphylococcus aureus (MRSA and MSSA strains, respectively). This compound and several known alkyl gallates were tested with MRSA and MSSA strains to gain new insights into their structural functions in relation to antimicrobial and beta-lactam susceptibility-intensifying activities. The maximum activity of alkyl gallates against MRSA and MSSA strains occurred at 1-nonyl and 1-decyl gallate, with an MIC at which 90% of the isolates tested were inhibited of 15.6 microg/ml. At concentrations lower than the MIC, alkyl gallates synergistically elevated the susceptibility of MRSA and MSSA strains to beta-lactam antibiotics. Such a synergistic activity of the alkyl gallates appears to be specific for beta-lactam antibiotics, because no significant changes were observed in the MICs of other classes of antibiotics examined in this study. The length of the alkyl chain was also associated with the modifying activity of the alkyl gallates, and the optimum length was C5 to C6. The present work clearly demonstrates that the length of the alkyl chain has a key role in the elevation of susceptibility to beta-lactam antibiotics.
Erdem Yesilada, Erdal Bedir, Çalış İhsan, Yoshihisa Takaishi and Yasukazu Ohmoto : Effects of triterpene saponins from Astragalus species on in vitro cytokine release, Journal of Ethnopharmacology, Vol.96, No.1-2, 71-77, 2005.
(要約)
Roots of Astragalus species are used to treat leukemia and for wound healing in Turkish folk medicine. In order to evaluate this information, the effect of 13 cycloartane- and 1 oleanan-type triterpene saponins isolated from Turkish species (Astragalus brachypterus, Astragalus cephalotes, Astragalus microcephalus, and Astragalus trojanus), as well as methanol extracts from the roots of three Astragalus species (Astragalus cephalotes, Astragalus oleifolius and Astragalus trojanus) were studied. Cytokine concentrations of interleukins IL-1beta, IL-8 and TNF-alpha after bacterial lipopolysaccharide (LPS) and IL-2, IL-4 and INF-gamma after phorbolacetate (PHA) stimulation were determined using commercial enzyme-linked immunosorbent assay (ELISA) kits. All triterpene saponins tested in the present study showed a prominent IL-2 inducing activity between 35.9% and 139.6%. Among the extracts the highest score was obtained for Astragalus oleifolius (141.2%). Glycosides of 20,24-epoxy and 20,25-epoxy cycloartanes showed higher IL-2 inducing activity than those of acyclic-cycloartane derivatives as well as aglycone of 20,24-epoxy cycloartanes, cycloastrogenol. Especially the activity of Astragaloside VII, a tridesmosidic glycoside of cycloastrogenol, was the most remarkable. The oleanan-type triterpene saponin also showed a prominent IL-2 inducing activity. IL-2 is a cytokine produced by activated T cells, which has shown powerful immunostimulatory and antineoplastic properties. Accordingly, the IL-2 inducing activity of the triterpene saponins might be the mechanism involved in order to explain the immunomodulatory and anticancer effects of Astragalus species.
Kentaro Kogure, Aiko Yamauchi, Akira Tokumura, Kyoko Kondou, Naonobu Tanaka, Yoshihisa Takaishi and Kenji Fukuzawa : Novel antioxidants isolated from plants of the genera Ferula, Inula, Prangos and Rheum collected in Uzbekistan, Phytomedicine, Vol.11, No.7-8, 645-651, 2004.
(要約)
We examined the effects of 48 compounds isolated from Ferula pallida, F. penninervis, Inula macrophylla, Prangos pabularia, P. tschimganica and Rheum maximowiczii collected in Uzbekistan on ADP/Fe2+-induced lipid peroxidation of egg yolk phosphatidylcholine liposomes. Of those compounds, 23 inhibited ADP/Fe2+-induced lipid peroxidation and nine showed especially strong inhibition of lipid peroxidation. Most compounds that inhibited peroxidation scavenged the 1,1'-diphenyl-2-picrylhydrazyl (DPPH) radical, indicating that the inhibition was due to radical scavenging. However, some compounds did not scavenge DPPH but inhibited lipid peroxidation significantly, suggesting that their inhibitory effect was not due to radical scavenging but to some other mechanism, such as prevention of Fe2+ function. Thus, we found various new antioxidants, some of which had a unique mechanism of action, in Ferula, Inula, Prangos and Rheum plants collected in Uzbekistan as seeds used in medicine.
Hiroyuki Nakagawa, Yoshihisa Takaishi, Yoshinori Fujimoto, Carmenza Duque, Cristina Garzon, Mitsunobu Sato, Masato Okamoto, Tetsuya Oshikawa and Sharif Uddin Ahmed : Chemical Constituents from the Colombian Medicinal Plant Maytenus laevis, Journal of Natural Products, Vol.67, No.11, 1919-1924, 2004.
(要約)
The methanol extract of the bark of the Colombian medicinal plant Maytenus laevis gave six new compounds and 28 known compounds. The structures of the new and known compounds were elucidated on the basis of spectroscopic evidence. Several of these compounds were screened for cytokine-inducing activity on human PBMCs to investigate antitumor effects, and canophyllol (12) demonstrated the most effective induction of the cytokines.
Yousuke Kawaguchi, Toshimasa Ochi, Yoshihisa Takaishi, Kazuyoshi Kawazoe and Kuo-Hsiung Lee : New Sesquiterpenes from Capsicum annuum, Journal of Natural Products, Vol.67, No.11, 1893-1896, 2004.
(要約)
The ethyl acetate soluble fraction of a MeOH extract of the dried stems and roots of Capsicum annum gave 10 new sesquiterpenoids (1-10) and nine known compounds. The structures of the new compounds were elucidated on the basis of spectroscopic evidence. The isolated new compounds were evaluated for their cytotoxic activities.
Naonobu Tanaka, Yoshihisa Takaishi, Yasuhiro Shikishima, Yuka Nakanishi, Kenneth Bastow, Kuo-Hsiung Lee, Gisho Honda, Michiho Ito, Yoshio Takeda, Olimjon K. Kodzhimatov and Ozodbek Ashurmetov : Prenylated Benzophenones and Xanthones from Hypericum scabrum, Journal of Natural Products, Vol.67, No.11, 1870-1875, 2004.
(要約)
Two new polyprenylated benzophenones, a new polyprenylated phloroglucinol, and six new xanthone derivatives were isolated from the aerial parts of the Uzbekistan medicinal plant Hypericum scabrum. Their structures were elucidated on the basis of spectroscopic evidence. The isolated compounds showed moderate cytotoxicity for human tumor cells.
Naonobu Tanaka, Nobuyuki Ooba, Hongquan Duan, Yoshihisa Takaishi, Yuka Nakanishi, Kenneth Bastow and Kuo-Hsiung Lee : Kaurane and abietane diterpenoids from Tripterygium doianum (Celastraceae), Phytochemistry, Vol.65, No.14, 2071-2076, 2004.
(要約)
Extraction of Tripterygium doianum (Celastraceae) afforded five new diterpenoids and 11 known diterpenoids belonging to the ent-kaurane and abietane families. Their structures were established based on spectroscopic studies. The isolated compounds showed moderate cytotoxicity against human tumor cell assays.
Mamoru Okasaka, Yoshihisa Takaishi, Kentaro Kogure, Kenji Fukuzawa, Hirofumi Shibata, Tomihiko Higuti, Gisho Honda, Michiho Ito, Olimjon K. Kodzhimatov and Ozodbek Ashurmetov : New Stilbene Derivatives from Calligonum leucocladum, Journal of Natural Products, Vol.67, No.6, 1044-1046, 2004.
(要約)
Two new stilbene derivatives, (E)-resveratrol 3-(6' '-galloyl)-O-beta-D-glucopyranoside (1) and (E)-resveratrol 3-(4' '-acetyl)-O-beta-D-xylopyranoside (2), and five known stilbene derivatives (3-7) were isolated from the dried aerial parts of Calligonum leucocladum. Their structures were established on the basis of spectroscopic evidence. Compound 1 showed antioxidant activity and a restorative effect of the inhibition of oxacillin to oxacillin/methicillin-resistant Staphylococcus aureus.
Sezik Ekrem, Erdem Yesilada, Hüsnitdin Shadidoyatov, Zeynullah Kulivey, Alim M. Nigmatullaev, Aripov N. Hamdulla, Yoshihisa Takaishi, Yoshio Takeda and Gisho Honda : Folk medicine in Uzbekistan: I. Toshkent, Djizzax, and Samarqand provinces, Journal of Ethnopharmacology, Vol.92, No.2-3, 197-207, 2004.
(要約)
Uzbekistan is one of the Turcic republics in Central Asia where a desert continental climate mainly prevails in territories. Nevertheless, this expedition was carried out in the northeast and east higher lands, where flora is richer. The interviews were performed in seven villages of Toshkent and in neighboring provinces of Samarqand, Djizzax and at Urgut Bazaar of Samarqand. Altogether 177 folk remedies were recorded in the surveyed area. Among these folk remedies, 162 remedies were obtained from 79 different kinds of plant species that belong to 31 different families, whereas, 15 animal originated remedies that belong to 8 different animals are listed, which includes their vernacular and scientific names, indications and recipes for preparations.
(キーワード)
Uzbekistan / Folk medicine / Toshkent / Samarqand / Djizzax
Wenyuan Gao, Rong Zhang, Wei Jia, Jun Zhang, Yoshihisa Takaishi and Hongquan Duan : Immunosuppressive Diterpenes from Veronicastrum sibiricum, Chemical & Pharmaceutical Bulletin, Vol.52, No.1, 136-137, 2004.
(要約)
Two new diterpenes, named sibiriquinone A (1) and B (2), along with four known diterpenes have been isolated from the aerial part of Veronicastrum sibiricum. Their structures were elucidated by spectroscopy. The isolated compounds showed significant immunosuppressive activities.
Ai Suga, Yoshihisa Takaishi, Satoru GOTO, Tatsuo Munakata, Izumi Yamauchi and Kentaro Kogure : Two lignan dimers from bamboo stems (Phyllostachys edulis), Phytochemistry, Vol.64, No.5, 991-996, 2003.
(要約)
Phyllostadimers A and B, two bis-lignans in which the two lignan units are directly connected by a C-C bond, were isolated from stems of bamboo, Phyllostachys edulis. Their structures were determined on the basis of spectral evidence. In addition, 14 known compounds were also obtained throughout the investigation. Phyllostadimer A significantly inhibited liposomal lipid peroxidation.
Masahiro Nagase, Jinsei Oto, Sin Sugiyama, Kouichi Yube, Yoshihisa Takaishi and Nobuo Sakato : Apoptosis Induction in HL-60 Cells and Inhibition of Topoisomerase II by Triterpene Celastrol, Bioscience, Biotechnology, and Biochemistry, Vol.67, No.9, 1883-1887, 2003.
(要約)
Celastrol, which is a triterpene purified from Celastraceae plants, has anticancer and anti-inflammatory activities. In this study we investigated to clarify whether celastrol can induce apoptosis in a human leukemia HL-60 model system. Celastrol was found to induce apoptosis, and the rank order of the potency of celastrol and its derivatives to induce internucleosomal DNA fragmentation was found to be celastrol>cela-H>the other derivatives=vehicle control. Many anticancer agents are known to possess the ability to inhibit topoisomerase II, so the inhibitory activities of celastrol and its derivatives on topoisomerase II were also explored. The rank order of the inhibitory activity was found to be celastrol>etoposide>cela-H, indicating that the apoptosis-inducing activities of cela derivatives correspond to their inhibitory activities on topoisomerase II. These data suggested that celastrol may cause its effects such as anticancer activity by the mechanism of apoptosis along with topoisomerase II inhibition.
Toshimasa Ochi, Yoshihisa Takaishi, Kentarou Kogure and Izumi Yamauti : Antioxidant Activity of a New Capsaicin Derivative from Capsicum annuum, Journal of Natural Products, Vol.66, No.8, 1094-1096, 2003.
(要約)
A new capsaicin derivative, 6' ',7' '-dihydro-5',5' "-dicapsaicin (1), and a known capsaicin metabolite, omega-hydroxycapsaicin (2),(1) were isolated from the fruit of Capsicum annuum. Their structures were established on the basis of spectroscopic evidence. Compound 1 showed almost the same antioxidant activity as capsaicin, but did not have a pungent taste.
(キーワード)
Antioxidants / Capsaicin / Capsicum / Fruit / Japan / Lipid Metabolism / Liposomes / Molecular Structure / Nuclear Magnetic Resonance, Biomolecular / Plants, Medicinal / Taste
From the aerial part of Artemisia tenuisecta Nevski (Asteraceae) a new sesquiterpene along with 16 known sesquiterpenoides were isolated. Its relative structure was elucidated as 1α-acetoxyeudesm- 4,5-expoxy-6β,11βH-12,6-olide from the 2D NMR and other spectral evidence.
Kazuyoshi Kawazoe, Yoshiko Tsubouchi, Norasyikin Abdullah, Yoshihisa Takaishi, Hirofumi Shibata, Tomihiko Higuti, Hitoshi Hori and Makoto Ogawa : Sesquiterpenoids from Artemisia gilvescens and an Anti-MRSA Compound, Journal of Natural Products, Vol.66, No.4, 538-539, 2003.
(要約)
A new secoguaianolide sesquiterpene (1) was isolated along with its three stereoisomers (2-4) from the nonmedicinal plant Artemisia gilvescens. The structure of 1 was elucidated to be (4S,5S)-dihydro-5-[(1R,2S)-2-hydroxy-2-methyl-5-oxo-3-cyclopenten-1-yl]-3-methylene-4-(3-oxobutyl)-2(3H)-furanone on the basis of 2D NMR and other spectroscopic evidence. Five known sesquiterpenoids were also isolated from this plant, and one of them (5) showed activity against methicillin-resistant Staphylococcus aureus (MRSA).
Yasuhiro Shikishima, Yoshihisa Takaishi, Gisho Honda, Michiho Ito, Yoshio Takeda, Motoo Tori, Shigeru Takaoka, Olimjon K. Kodzhimatov and Ozodbek Ashurmetov : Sesquiterpenes from Ferula penninervis, Journal of Natural Products, Vol.65, No.12, 1897-1903, 2002.
(要約)
The ethyl acetate soluble extract of the dried roots of Ferula penninervis gave 17 new sesquiterpenes [15 of the guaiane-type, ferupennins A-O (1-15), and two of the eudesmane-type, 1alpha-hydroxy-2-oxo-5alpha,7beta,11betaH-eudesm-3-en-6alpha,12-olide (16) and penninervin (17)] and nine known sesquiterpenes. The structures of the new compounds were elucidated on the basis of spectroscopic evidence and X-ray analysis. The absolute configuration of ferupennin A (1) was determined by a modified Mosher method.
Hongquan Duan, Yoshihisa Takaishi, Motoo Tori, Shigeru Takaoka, Gisho Honda, Michiho Ito, Yoshio Takeda, Olimjon K. Kodzhimatov and Ozodebek A Ashurmetov : Polysulfide Derivatives from Ferula foetida, Journal of Natural Products, Vol.65, No.11, 1667-1669, 2002.
(要約)
The ethyl acetate-soluble fraction from a methanol extract of Ferula foetida has afforded six new sulfide derivatives, (E)-3-methylsulfinyl-2-propenyl sec-butyl disulfide (foetisulfide A) (1), (Z)-3-methylsulfinyloxy-2-propenyl sec-butyl disulfide (foetisulfide B) (2), (E)-3-methylsulfinyloxy-2-propenyl sec-butyl disulfide (foetisulfide C) (3), bis(3-methylthio-2E-propenyl) disulfide (foetisulfide D) (4), 3,4,5-trimethyl-2-thiophenecarboxylic acid (foetithiophene A) (5), 3,4,5-trimethyl-2-(methylsulfinyloxymethyl)thiophene (foetithiophene B) (6), along with six known compounds. The structures of 1-6 were established on the basis of spectroscopic studies, with the elucidation of 5 confirmed by single-crystal X-ray crystallography.
The extract of Tripterygium doianum (Celastraceae) afforded three triterpenoids [3beta-acetoxy-11-ursen-13alpha,30-olide, 25-chloro-24-hydroxytirucall-7-en-3-one and tirucall-7-en-3,24-dione], two sesquiterpenoids [5alpha-acetoxy-1beta,8alpha-bis-cinnamoyl-4alpha-hydroxydihydroagarofuran and 5alpha-acetoxy-1beta-benzoyl-8alpha-cinnamoyl-4alpha-hydroxydihydroagarofuran] and nine known triterpenoids. Their structures were established based on spectroscopic studies.
Michiko Matsuhisa, Yasuhiro Shikishima, Yoshihisa Takaishi, Gisho Honda, Michiho Ito, Yoshio Takeda, Hirofumi Shibata, Tomihiko Higuti, Olimjon K. Kodzhimatov and Ozodbek Ashurmetov : Benzoylphloroglucinol Derivatives from Hypericum scabrum, Journal of Natural Products, Vol.65, No.3, 290-294, 2002.
(要約)
Nine new polyprenylated benzoylphloroglucinol derivatives, hyperibones A-I (1-9), were isolated from the aerial parts of the Uzbekistan medicinal plant Hypericum scabrum. Their structures were determined mainly on the basis of spectroscopic evidence (2D NMR and HRMS). Compounds 1, 2, and 4 showed mild in vitro antibacterial activity against methicillin-resistance Staphylococus aureus (MRSA) and methicillin-sensitive Staphylococus aureus (MSSA).
Hongquan Duan, Yoshihisa Takaishi, Yoshinori Fujimoto, Cristina Garzon, Coralia Osorio and Carmenza Duque : Chemical Constituents from the Colombian Medicinal Plant Niphogeton ternata, Chemical & Pharmaceutical Bulletin, Vol.50, No.1, 115-117, 2002.
(要約)
Two coumarins and one polyacetylene, 5-O-(3-chloro-2-hydroxy-3-methylbutyl)-8-methoxypsoralen(1), 2', 3'-dihydro-jatamansin(2), and 10-chloro-1-heptadecene-4, 6-diyne-3, 8, 9-triol(3), along with 15 known compounds(4-18), were isolated from the methanol extract of Niphogeton ternata. Their structures were elucidated by spectroscopy.
Hongquan Duan, Yoshihisa Takaishi, Hiroshi Momota, Yasukazu Ohmoto and Takao Taki : Immunosuppressive constituents from Saussurea medusa, Phytochemistry, Vol.59, No.1, 85-90, 2002.
(要約)
The methanol extract of Saussurea medusa Maxim afforded two lignans: 2alpha-guaicyl-4-oxo-6alpha-catechyl-3,7-dioxabicyclo [3.3.0]octane and 1alpha-hydroxy-2alpha,4alpha-guaicyl-3,7-dioxabicyclo[3.3.0]octane; two chlorophyll derivatives: 13-epi-phaeophorbide-a and 13-epi-phaeophorbide-a methyl ester; one megastigmane derivative: 3beta-hydroxy-5alpha,6alpha-epoxy-7-megastigmen-9-one, along with 19 known compounds. Their structures were established on the basis of spectroscopic studies.
D. Deliorman, E. Yesilada, F. Ergun, Y. Tsuchiya and Yoshihisa Takaishi : The antioxidant activity of the extracts and fractions from Carduus nutans L., Gazi Universitesi Eczacilik Fakultesi Dergisi, Vol.19, No.1, 61-66, 2002.
121.
Bo Fu, Bao-Ning Su, Yoshihisa Takaishi, Gisho Honda, Michiho Ito, Yoshio Takeda, Olimjon K. Kodzhimatov and Ozodbek Ashurmetov : A bis-sesquiterpene and sesquiterpenolides from Inula macrophylla, Phytochemistry, Vol.58, No.7, 1121-1128, 2001.
(要約)
Macrophyllidimer C, a novel bis-sesquiterpene, in which the two sesquiterpene units are directly connected by a C-C bond, and eight other sesquiterpenolides were obtained from the bark of Inula macrophylla. Seven of these, macrophyllilactones A-G, are new eudesmanolide- and elemanolide-type sesquiterpenes. Their structures were determined on the basis of spectroscopic evidence and chemical reaction.
(キーワード)
Inula macrophylla / Compositae / Macrophyllidimer C / bis-Sesquiterpene / Macrophyllilactones A G / Eudesmanolide and elemanolide sesquiterpenes
Kimiko Tamemoto, Yoshihisa Takaishi, Bei Chen, Kazuyoshi Kawazoe, Hirofumi Shibata, Tomihiko Higuti, Gisho Honda, Michiho Ito, Yoshio Takeda, Olimjon K. Kodzhimatov and Ozodbek Ashurmetov : Sesquiterpenoids from the fruits of Ferula kuhistanica and antibacterial activity of the constituents of F. kuhistanica, Phytochemistry, Vol.58, No.5, 763-767, 2001.
(要約)
Ethyl acetate extracts of the air-dried fruits of Ferula kuhistanica afforded three daucane esters: kuhistanicaol H, I and J, together with nine other known compounds. Their structures were established on the basis of spectroscopic evidence. Isolated compounds in this paper and previously reported compounds from the roots and stems of F. kuhistanica were tested for antibacterial activity. Some of them were selectively toxic against Gram-positive bacteria, including methicillin-sensitive and methicillin-resistant Staphylococcus aureus (MSSA and MRSA).
Yoshio Takeda, Natsuko Isai, Toshiya Masuda, Gisho Honda, Yoshihisa Takaishi, Michiho Ito, Hideaki Otsuka, Ozodebek A Ashurmetov and Olimjon K Khodzhimatov : Phlomisflavosides A and B, new flavonol diglycosides from Phlomis spinidens, Chemical & Pharmaceutical Bulletin, Vol.49, No.8, 1039-1041, 2001.
(要約)
ウズベキスタン産シソ科植物Phlomis spinidensの配糖体成分を検索し，新フラボノールdiglycosides,phlomisflavosides A, Bを単離し，その化学構造を明らかにした．
125.
Yasuhiro Shikishima, Yoshihisa Takaishi, Gisho Honda, Michiho Ito, Yoshio Takeda, Olimjon K. Kodzhimatov, Ozodbek Ashurmetov and Kuo-Hsing Lee : Chemical Constituents of Prangos tschimganica; Structure Elucidation and Absolute Configuration of Coumarin and Furanocoumarin Derivatives with Anti-HIV Activity, Chemical & Pharmaceutical Bulletin, Vol.49, No.7, 877-880, 2001.
(要約)
The methanol extract of the dried aerial parts of Prangos tschimganica gave three new coumarin derivatives and 30 known coumarin derivatives. Their structures were established on the basis of chemical and spectroscopic evidence. Absolute configuration of the isolated compounds were determined by using a modified Mosher's method. Some of the isolated compounds showed anti-HIV activity.
Bei Chen, Yoshihisa Takaishi, Kazuyoshi Kawazoe, Kimiko Tamemoto, Gisho Honda, Michiho Ito, Yoshio Takeda, Olimjon K. Kodzhimatov and Ozodbek Ashurmetov : Farnesyl Hydroxybenzoic Acid Derivatives from Ferula kuhistanica, Chemical & Pharmaceutical Bulletin, Vol.49, No.6, 707-710, 2001.
(要約)
Four new farnesyl hydroxybenzoic acid derivatives, kuhistanols E-H(1-4), were isolated from the roots of the Uzbekistan medicinal plant Ferula kuhistanica. The structures of the new compounds were elucidated based on spectroscopic and chemical evidence.
Hiroyuki Nakagawa, Hongquan Duan and Yoshihisa Takaishi : Limonoids from Citrus sudachi, Chemical & Pharmaceutical Bulletin, Vol.49, No.5, 649-651, 2001.
(要約)
Four new limonoid derivatives, 1-O-methylichangensin(1), sudachinoid A(2), B(3), and C(4)were isolated from the seeds of Citrus sudachi, together with the known compounds ichangensin, obacunone, obacunoic acid and limonin, and the structures of the new compounds were elucidated based on spectroscopic and chemical evidence.
Bao-Ning Su, Yoshihisa Takaishi, Tetsuya Yabuuchi, Takenori Kusumi, Motoo Tori, Shigeru Takaoka, Gisho Honda, Michiho Ito, Yoshio Takeda, Olimjon K. Kodzhimatov and Ozodbek Ashurmetov : Sesquiterpenes and Monoterpenes from the Bark of Inula macrophylla, Journal of Natural Products, Vol.64, No.4, 466-471, 2001.
(要約)
Eleven new sesquiterpenes (1--11) and two thymol derivatives (12, 13), along with 12 known sesquiterpenes and monoterpenes, were isolated from the bark of Inula macrophylla. Their structures were determined on the basis of spectral evidence (especially by HREIMS and 2D NMR) as well as chemical transformations. The structure of macrophyllic acid A (1) was confirmed by X-ray analysis, and the absolute configuration of 1 was determined on the basis of the appropriate chemical conversions and the application of a modified Mosher's method.
Yasuhiro Shikishima, Yoshihisa Takaishi, Gisho Honda, Michiho Ito, Yoshio Takeda, Olimjon K. Kodzhimatov and Ozodbek Ashurmetov : Terpenoids and γ-pyrone derivatives from Prangos tschimganica, Phytochemistry, Vol.57, No.1, 135-141, 2001.
(要約)
The methanol extract of the dried aerial parts of Prangos tschimganica afforded seven monoterpenoids and four gamma-pyrone derivatives. Their structures were established on the basis of chemical and spectroscopic evidence.
Hong-Quan Duan, Yoshihisa Takaishi, Yong-Feng Jia and Duan Li : Sesquiterpene polyol esters from Tripterygium wilfordii, Phytochemistry, Vol.56, No.4, 341-346, 2001.
(要約)
The extract (T(II)) of Tripterygium wilfordii Hook f. afforded four sesquiterpene esters: 1beta,2beta,5alpha,8beta,11-pentaacetoxy-4alpha-hydroxy-3alpha(2'-methylbutanoyl)-15-nicotinoyl-7-oxo-dihydroagarofuran; 1beta,5alpha,11-triacetoxy-7beta-benzoyl-4alpha-hydroxy-8beta-nicotinoyl-dihydroagarofuran; 1beta,2beta,5alpha,11-tetraacetoxy-8alpha-benzoyl-4alpha-hydroxy-7beta-nicotinoyl-dihydroagarofuran; 5alpha-benzoyl-4alpha-hydroxy-1beta,8alpha-dinicotinoyl-dihydro- agarofuran as well as one other known sesquiterpene ester. Their structures were established on the basis of spectroscopic studies.
Shikishima Yasuhiro, Yoshihisa Takaishi, Gisho Honda, Michiho Ito, Yoshio Takeda, Olimjon K. Kodzhimatov and Ozodbek Ashurmetov : Phenylbutanoids and stilbene derivatives of Rheum maximowiczii, Phytochemistry, Vol.56, No.4, 377-381, 2001.
(要約)
The methanol extract of the dried roots of Rheum maximowiczii afforded four phenylbutanoid and two stilbene derivatives. Their structures were established on the basis of chemical and spectroscopic studies.
Ekrem Sezik, Erdem Yesilada, Gisho Honda, Yoshihisa Takaishi, Yoshio Takeda and Toshihiro Tanaka : Traditional medicine in Turkey X. Folk medicine in Central Anatolia, Journal of Ethnopharmacology, Vol.75, No.2-3, 95-115, 2001.
Hongquan Duan, Yoshihisa Takaishi, Hiroshi Momota, Yasukazu Ohmoto, Takao Taki, Yongfeng Jia and Duan Li : Immunosuppressive Sesquiterpene Alkaloids from Tripterygium wilfordii, Journal of Natural Products, Vol.64, No.5, 582-587, 2001.
(要約)
Nine new sesquiterpene pyridine alkaloids [wilfornines A (1), B (2), C (3), D (4), E (5), F (8), and G (9); wilfordinines I (6) and J (7)] and six known compounds (10-15) were isolated from a clinically used extract (T(II)) of Tripterygium wilfordii. The structures of 1-9 were elucidated by spectroscopic and chemical methods. The inhibitory effects on cytokine production of 1-3 and several related compounds were evaluated. Compounds 10 and 14 showed significant inhibitory effects on cytokine production.
(キーワード)
Alkaloids / Anti-Inflammatory Agents / China / Cytokines / Humans / Immunosuppressive Agents / Magnetic Resonance Spectroscopy / Monocytes / Plants, Medicinal / Prednisolone / Sesquiterpenes / Spectrometry, Mass, Fast Atom Bombardment / Spectrophotometry, Infrared
Kazuyoshi Kawazoe, Aki Yutani, Kimiko Tamemoto, Shuko Yuasa, Hirofumi Shibata, Tomihiko Higuti and Yoshihisa Takaishi : Phenylnaphthalene Compounds from the Subterranean Part of Vitex rotundifolia and Their Antibacterial Activity Against Methicillin-Resistant Staphylococcus aureus, Journal of Natural Products, Vol.64, No.5, 588-591, 2001.
(要約)
A careful investigation of the subterranean part of Vitex rotundifolia has shown that this plant contains five novel lignans having a 1-phenylnaphthalene-type skeleton together with four known lignans. These structures were elucidated on the basis of spectroscopic data. Furthermore, some of the isolated compounds showed antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA).
Erdem Yesilada, Koichiro Tsuchiya, Yoshihisa Takaishi and Kazuyoshi Kawazoe : Isolation and characterization of free radical scavenging flavonoid glycosides from the flowers of Spartium junceum by activity-guided fractionation, Journal of Ethnopharmacology, Vol.73, No.3, 471-478, 2000.
(要約)
Spartium junceum L. (Fabaceae) flowers are used for the treatment of peptic ulcers in Turkish folk medicine. The possible superoxide dismutase-like activity of the extracts, fractions and constituents obtained through activity-guided fractionation were studied by using in vitro electron spin resonance spectrometry, in order to explain the role of antioxidant principles in the potent antiulcerogenic activity of the extract. Despite the fact that the triterpene, spartitrioside, which was previously reported as the active antiulcerogenic constituent of the flowers was found almost inactive, the flavonoid-rich fractions showed potent antioxidant activity. Five flavonoid glycosides bearing catechol structure in ring B were isolated from the butanol extract and their structures were elucidated using 1H- and 13C-NMR techniques as isoquercitrin (quercetin 3beta-glucoside) (1,); luteolin 4'beta-glucoside (2); quercetin 3, 4'-diglucoside (3); azaleatin 3beta-glucoside (quercetin 5-methylether 3beta-glucoside) (4), quercetin 4'beta-glucoside (5). Flavonoids (2) and (4) showed the highest in vitro antioxidant activity with 22.59 and 19.08 U/ml, respectively.
Bei Chen, Rie Teranishi, Kazuyoshi Kawazoe, Yoshihisa Takaishi, Gisho Honda, Michiho Itoh, Michiho Itoh, Yoshio Takeda and Olimjon K. Kodzhimatov : Sesquiterpenoids from Ferula kuhistanica, Phytochemistry, Vol.54, No.7, 717-722, 2000.
(要約)
Methanol extracts of the air-dried roots and stems of Ferula kuhistanica afforded seven daucane-type sesquiterpenes, called kuhistanicaol A-G, together with 13 known daucane esters. Their structures were established on the basis of spectroscopic evidence and the results of chemical reactions.
(キーワード)
Ferula kuhistanica / Umbelliferae / Sesquiterpenes / Daucane esters / Kuhistanicaol A G
Erdem Yesilada, Yoshihisa Takaishi, Tetsuro Fujita and Ekrem Sezik : Anti-ulcerogenic effects of Spartium junceum flowers on in vivo test models in rats, Journal of Ethnopharmacology, Vol.70, No.3, 219-226, 2000.
(要約)
Flowers of Spartium junceum L. (Fabaceae) are used for the treatment of gastric ulcers in Turkish folk medicine. Through bioassay-guided fractionation using chemical and chromatographical means and water immersion and restraint-induced stress ulcer model in rats, a saponin fraction was determined as the potent anti-ulcerogenic ingredient. The active fraction was also highly effective in preventing ethanol- and pyloric ligation-induced gastric lesions as well as inhibiting gastric secretion volume, gastric pH and titratable acidity, but did not affect the hexosamine content of the gastric mucosa. A novel oleanen-type triterpenic saponin, named as spartitrioside, was isolated as the active principle by using chromatographical separation techniques.
Hongquan Duan, Yoshihisa Takaishi, Hiroshi Momota, Yasukazu Ohmoto, Takao Taki, Yongfeng Jia and Duan Li : Triterpenoids from Tripterygium wilfordii, Phytochemistry, Vol.53, No.7, 805-810, 2000.
(要約)
The extract (T(II)) of Tripterygium wilfordii Hook f. afforded four triterpenoids: wilforic acid D (3beta,24-epoxy-2alpha-hydroxy-24R*-ethoxy-29-friedelanoic acid); (E) 3beta,24-epoxy-2-oxo-3alpha-hydroxy-29-friedelanoic acid; (F) 2beta-hydroxy-3-oxo-friedelan-29-oic acid; 29-hydroxy-3-oxo-olean-12-en-28-oic acid and 17 known triterpenoids. Their structures were established on the basis of spectroscopic studies. In a bioactivity analysis, only the known dulcioic acid compound showed a significant inhibitory effect on cytokine production.
Bao-Ning Su, Yoshihisa Takaishi, Tetsuya Yabuuchi, Takenori Kusumi, Motoo Tori and Shigeru Takaoka : The structures and absolute configurations of macrophyllic acids A E, five new rearranged eudesmane sesquiterpene acids from the bark of Inula macrophylla, Tetrahedron Letters, Vol.41, No.14, 2395-2400, 2000.
(キーワード)
Inula macrophylla / compositae / macrophyllic acids A E / sesquiterpene acid / new carbon skeleton / NMR data / chemical transformation / X-ray analysis / absolute configuration / biosynthetic pathway
Bao-Ning Su, Yoshihisa Takaishi, Gisho Honda, Michiho Itoh, Yoshio Takeda, Olimjon K. Kodzhimatov and Ozodbek Ashurmetov : Sesquiterpene Phenylpropanoid and Sesquiterpene Chromone Derivatives from Ferula pallida, Journal of Natural Products, Vol.63, No.4, 520-522, 2000.
(要約)
Four novel compounds-two sesquiterpene phenylpropanoid derivatives, pallidones G (1) and H (2), and two sesquiterpene chromone derivatives, pallidones I (3) and J (4)-have been isolated from the roots of Ferula pallida. Their structures were determined on the basis of NMR and HREIMS evidence.
Reiko Fujita, Hongquan Duan and Yoshihisa Takaishi : Terpenoids from Tripterigyum hypoglaucum, Phytochemistry, Vol.53, No.6, 715-722, 2000.
(要約)
Six terpenoids have been isolated from the root bark of Tripterygium hypoglaucum, along with 14 known compounds. The structures of the terpenoids were elucidated as 3,11,14-oxo-abieta-8,12-diene, 3beta-hydroxy-12,14-dimethoxyabieta-8,11,13-triene, 3beta-hydroxy-11alpha-ethoxyurs-12-ene, 3beta-hydroxy-11alpha-methoxyurs-12-ene, 3beta-hydroxy-11alpha-methoxyolean-12-ene-28-oic acid, and 1beta-benzoyl-8alpha-cinnamoyl-4alpha,5alpha- dihydroxydihydroagarofuran.
Ping Zhou, Yoshihisa Takaishi, Hongquan Duan, Bei Chen, Gisho Honda, Michiho Itoh, Yoshio Takeda, Kodzhimatov K. Olimjon and Kuo-Hsing Lee : Coumarins and bicoumarin from Ferula sumbul: anti-HIV activity and inhibition of cytokine release, Phytochemistry, Vol.53, No.6, 689-697, 2000.
(要約)
The methanol extract of the dried roots of Ferula sumbul afforded two furanocoumarin esters, fesumtuorin A, B, one bicoumarin, fesumtuorin C, five spirobicoumarins, fesumtuorin D, E, F, G and H, along with nineteen known coumarins. Their structures were established on the basis of spectroscopic studies. Some of the isolated compounds showed anti-HIV activity and very weak inhibition of cytokine release.
Hongquan Duan, Yoshihisa Takaishi, Yasuhiro Imakura, Yongfong Jia, Duan Li, Mark L Cosentino and Kuo-Hsiung Lee : Sesquiterpene Alkaloids from Tripterygium hypoglaucum and Tripterygium wilfordii: A New Class of Potent Anti-HIV Agents, Journal of Natural Products, Vol.63, No.3, 357-361, 2000.
(要約)
Five new sesquiterpene pyridine alkaloids [triptonines A (1) and B (2), and wilfordinines A (3), B (4), and C (5)] and two known compounds (peritassine A and hypoglaunine C) were isolated from Tripterygium hypoglaucum and a clinically used extract of Tripterygium wilfordii. The structures of 1-5 were elucidated by spectroscopic methods. The anti-HIV activity of 1, 2, and several related compounds was evaluated. Triptonine B (2) demonstrated potent anti-HIV activity with an EC(50) value of <0.10 microg/mL and an in vitro therapeutic index value of >1000.
Bei Chen, Kazuyoshi Kawazoe, Yoshihisa Takaishi, Gisho Honda, Michiho Itoh, Yoshio Takeda, Olimjon K. Kodzhimatov and Ozodbek Ashurmetov : Prenylated Benzoic Acid Derivatives from Ferula kuhistanica, Journal of Natural Products, Vol.63, No.3, 362-365, 2000.
(要約)
Four new prenylated benzoic acid derivatives, kuhistanols A-D (1-4), along with one known compound, 3-farnesyl-p-hydroxybenzoic acid (5), have been isolated from the roots of the Uzbekistan medicinal plant, Ferula kuhistanica. Their structures were established on the basis of chemical and spectral evidence. Compound 4 showed a significant inhibitory effect on cytokine production in lipopolysaccharide-stimulated human peripheral mononuclear cells.
Bao-Ning Su, Yoshihisa Takaishi, Motoo Tori, Shigeru Takaoka, Gisho Honda, Michiho Itoh, Yoshio Takeda, Olimjon K. Kodzhimatov and Ozodbek Ashurmetov : Macrophyllidimers A and B, two novel sesquiterpene dimers from the bark of Inula macrophylla, Tetrahedron Letters, Vol.41, No.9, 1475-1479, 2000.
(キーワード)
Inula macrophylla / Compositae / macrophyllidimers A and B / sesquiterpene dimer / NMR data / X-ray analysis
Bao-Ning Su, Yoshihisa Takaishi, Motoo Tori, Shigeru Takaoka, Gisho Honda, Michiho Itoh, Yoshio Takeda, Olimjon K. Kodzhimatov and Ozodbek Ashurmetov : Macrophyllols A and B, Two Unusual Novel Sesquiterpene and Monoterpene Dimers from the Bark of Inula macrophylla, Organic Letters, Vol.2, No.4, 493-496, 2000.
(要約)
[structure: see text] Two novel sesquiterpene and monoterpene dimers, macrophyllols A (1) and B (2), were isolated from the bark of Inula macrophylla. Their structures were determined on the basis of spectral evidence (especially HREIMS and 2D NMR) as well as chemical transformation. The structure of macrophyllol A (1) was confirmed by X-ray analysis. The possible biosynthetic pathways of macrophyllols A (1) and B (2) are discussed.
(キーワード)
Dimerization / Inula / Magnetic Resonance Spectroscopy / Mass Spectrometry / Molecular Structure / Terpenes / Trees
Bao-Ning Su, Yoshihisa Takaishi, Gisho Honda, Michiho Itoh, Yoshio Takeda, Olimjon K. Kodzhimatov and Ozodbek Ashurmetov : Sesquiterpene Coumarins and Related Derivatives from Ferula pallida, Journal of Natural Products, Vol.63, No.4, 436-440, 2000.
(要約)
Six new compounds-two sesquiterpene coumarins, pallidones A and B (1, 2), and four related derivatives, pallidones C-F (3-6), as well as two known sesquiterpene coumarins, feselol (7) and conferol (8), have been isolated from the EtOAc extracts of the roots of Ferula pallida. All structures of these compounds were determined on the basis of spectral evidence, especially 2D NMR ((1)H-(1)H COSY, HSQC, HMBC, and NOESY) and HRMS. The possible biosynthetic pathway of pallidones C-F (3-6) is discussed.
Akira Iida, Tomohiro Mihara, Tetsuro Fujita and Yoshihisa Takaishi : Peptidic immunosuppressants from the fungus Trichoderma polysporum, Bioorganic & Medicinal Chemistry Letters, Vol.9, No.24, 3393-3396, 1999.
(要約)
Three new 10-residue lipopeptaibols, trichopolyns III-V have been isolated from the fungus Trichoderma polysporum together with the known trichopolyns I and II. Structure determination has been achieved on the basis of spectroscopic and chemical evidence. These peptides have been shown to suppress the proliferation of lymphocytes in mouse allogeneic mixed lymphocyte reaction.
Bao-Ning Su, Yoshihisa Takaishi and Takenori Kusumi : Morinols A-L, twelve novel sesquineolignans and neolignans with a new carbon skeleton from morina chinensis, Tetrahedron, Vol.55, No.51, 14571-14586, 1999.
Bao-Ning Su and Yoshihisa Takaishi : Morinols A and B, Two Novel Tetrahydropyran Sesquineolignans with a New Carbon Skeleton from Morina chinensis, Chemistry Letters, Vol.28, No.12, 1315-1316, 1999.
155.
Hitomi Taninaka, Yoshihisa Takaishi, Gisho Honda, Yasuhiro Imakura, Ekrem Sezik and Erdem Yesilada : Terpenoids and aromatic compounds from Daphne oleoides ssp. oleoides, Phytochemistry, Vol.52, No.8, 1525-1529, 1999.
Bao-Ning Su and Yoshihisa Takaishi : Morinins L-P, Five New Phenylpropanol Derivatives from Morina chinensis, Chemical & Pharmaceutical Bulletin, Vol.47, No.11, 1569-1572, 1999.
Hongquan Duan, Yoshihisa Takaishi, Yongfong Jia and Duan Li : Sesquiterpene Alkaloids from Extracts of Tripterygium wilfordii, Chemical & Pharmaceutical Bulletin, Vol.47, No.11, 1664-1667, 1999.
Hongquan Duan, Yoshihisa Takaishi, Hiroshi Momota, Yasukazu Ohmoto, Takao Taki, Yongfeng Jia and Duan Li : Immunosuppressive Diterpenoids from Tripterygium wilfordii, Journal of Natural Products, Vol.62, No.11, 1522-1525, 1999.
(要約)
A clinically used extract of Tripterygium wilfordii afforded three new diterpenoids-3beta,19-dihydroxyabieta-8,11,13-triene (triptobenzene L) (1); 12,19-dihydroxy-3-oxoabieta-8,11,13-triene (triptobenzene M) (2); and 19-hydroxy-3,7-dioxo-abieta-8,11, 13-triene (triptobenzene N) (3)-along with 14 known diterpenoids. The structures of 1-3 were established on the basis of spectroscopic studies. Of the known compounds, the stereochemistry at C-4 of triptonediol (4) was reassigned. Tripterifordin (8) and 13-epi-manoyl oxide-18-oic acid (9) showed significant inhibitory effects on cytokine production.
(キーワード)
Anti-Inflammatory Agents / Cytokines / Depression, Chemical / Diterpenes, Abietane / Humans / Immunosuppressive Agents / Magnetic Resonance Spectroscopy / Medicine, Chinese Traditional / Phenanthrenes / Plants, Medicinal / Prednisolone / Spectrophotometry, Infrared / Spectrophotometry, Ultraviolet
Bao-Ning Su, Yoshihisa Takaishi, Hong-Quan Duan and Bei Chen : Phenylpropanol Derivatives from Morina chinensis, Journal of Natural Products, Vol.62, No.10, 1363-1366, 1999.
(要約)
Seven new phenylpropanol derivatives, named morinins A-G (1-7), along with five known compounds, 4-O-methylcinnamyl alcohol, 4-O-methylcinnamyl methyl ether, 4-O-methylcinnamyl acetate, p-methoxybenzaldehyde, and 4-O-methyl-(E)-coniferyl alcohol, have been isolated from the roots of the medicinal Chinese plant, Morina chinensis. Their structures were determined on the basis of spectral data, especially 2D NMR and HRMS.
Bao-Ning Su and Yoshihisa Takaishi : Morinins H-K, Four Novel Phenylpropanol Ester Lipid Metabolites from Morina chinensis, Journal of Natural Products, Vol.62, No.9, 1325-1327, 1999.
(要約)
The medicinal plant, Morina chinensis, afforded four novel phenylpropanol ester lipid metabolites, named morinins H-K (1-4). Their structures were identified on the basis of spectral data interpretation.
Yesilada Erdem and Yoshihisa Takaishi : A saponin with anti-ulcerogenic effect from the flowers of Spartium junceum, Phytochemistry, Vol.51, No.7, 903-908, 1999.
(要約)
A new oleanene-type saponin with potent anti-ulcerogenic activity was isolated from the flowers of Spartium junceum. The various techniques of NMR spectral analysis, viz. 1H, 13C, DEPT, C-H COSY, H-H COSY, COLOC, NOESY, HMBC, HMQC, in conjunction with EI- and FAB-mass spectrometry, revealed that the structure of the isolated saponin was 3-O-[alpha-L-rhamnopyranosyl-(1-->2) -O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucuronopyranosyl]-3 beta,16beta,22 beta,24-tetrahydroxy-olean-12-ene and named as spartitrioside.
Hongquan Duan, Yoshihisa Takaishi, Masahiko Bando, Masaru Kido, Yasuo Imakura and KuoHsiung Lee : Novel sesquiterpene esters with alkaloid and monoterpene and related compounds from Tripterygium hypoglaucum: A new class of potent anti-HIV agents, Tetrahedron Letters, Vol.40, No.15, 2969-2972, 1999.
Erdem Yesilada, Ekrem Sezik, Gisho Honda, Yoshihisa Takaishi, Yoshio Takeda and Toshihiro Tanaka : Traditional medicine in Turkey IX. Folk medicine in north west Anatolia, Journal of Ethnopharmacology, Vol.64, No.3, 195-210, 1999.
Kimiko Nakano, Chaiki Yoshida, Wakako Furukawa, Yoshihisa Takaishi and Kozo Shishido : Terpenoids in Transformed Root Culture of Tripterygium Wilfordii, Phytochemistry, Vol.49, No.6, 1821-1824, 1998.
172.
Kimiko Nakano, Chaiki Yoshida, Wakako Furukawa, Yoshihisa Takaishi and Kozo Shishido : Terpenoids in transformed root culture of Tripterygium wilfordii, Phytochemistry, Vol.49, No.6, 1821-1824, 1998.
(要約)
Investigation of a hairy root culture of Tripterygium wilfordii var. regelii transformed with Agrobacterium rhizogenes resulted in the isolation of new diterpenoid and sesquiterpenoid together with known triterpenoids. These structures were determined by spectroscopic analyses.
Erdem Yesilada, Didem Deliorman, Fatma Ergun, Yoshihisa Takaishi and Yukihisa Ono : Effects of the Turkish subspecies of Viscum album on macrophage-derived cytokines, Journal of Ethnopharmacology, Vol.61, No.3, 195-200, 1998.
(要約)
Viscum album L. herbs are used for the treatment of various diseases. Apart from their immunostimulatory, antitumor, and hypotension inducing activities, anti-inflammatory effects has also been recorded in the literature. Since the immunostimulatory activity of mistletoe is mainly attributed to a stimulation of the mononuclear phagocytic system and to an induction of inflammation by macrophage-derived cytokines, utilization based on anti-inflammatory activity seems in contrast with its use as immunostimulant. The inhibitory effects of 80% ethanol extracts and subfractions obtained by petroleum ether, diethylether, ethylacetate and n-butanol from three Turkish subspecies of V. album L. (ssp. album, ssp. abietis, ssp. austriacum) against interleukins (IL-1alpha and IL-1beta) and tumor necrosis factor-alpha were studied. Ethanolic (80%) extracts of all three subspecies exhibited almost no significant inhibitory activity on the proinflammatory cytokines, at least in the concentrations applied in this study. In contrast, they induce a concentration dependent stimulation of these cytokines. On the other hand, moderate to weak, dose dependent inhibitory effects were observed on fractionation, which may be attributed to the existence of less polar components with anti-inflammatory activity. Based on our results, it was concluded that the utilization of ethanol extracts for anti-inflammatory purposes would not be beneficial probably due to the partial extraction of the low-molecular-weight polypeptides, i.e. viscotoxins, which induce an inflammatory response. Moreover, for anti-inflammatory effects, extracts of Viscum album ssp. austriacum may be preferred, since higher inhibitory ratios were obtained against inflammatory cytokines than with the other two subspecies.
(キーワード)
Interleukin-1α / Interleukin-1β / Loranthaceae / Mistletoe / Tumor necrosis factor-α / Viscum album ssp. abietis / Viscum album ssp.album / Viscum album ssp. austriacum
J Oto, Z Islam, Yoshihisa Takaishi and N Sakato : Biological Activity of the Triterpene Celastrol : Analysis from the Viewpoint of the Apoptosis Induction, Technical Bulletein of Faculty of Agriculture, Vol.50, 79-87, 1998.
176.
Kimiko Nakano, Yoshiko Oose and Yoshihisa Takaishi : A novel epoxy-triterpene and nortriterpene from callus cultures of Tripterygium wilfordii, Phytochemistry, Vol.46, No.7, 1179-1182, 1997.
Mineo Niwa, Noriko Nakamura, Keiko Kitajima, Mari Ueda, Yasuyuki Tsutsumishita, Shiroh Futaki and Yoshihisa Takaishi : Benzoquinones Inhibit the Expression of Inducible Nitric Oxide Synthase Gene`, Biochemical and Biophysical Research Communications, Vol.239, No.2, 367-371, 1997.
(要約)
Benzoquinones inhibited the production of NO induced by LPS and gamma-IFN in C6 glia cells. The mechanistic studies showed that benzoquinones inhibited the expression of iNOS mRNA through inactivation of NF kappa B. Benzoquinones may be a useful candidate for the development of a drug to treat disease due to iNOS gene over-expression.
Erdem Yesilada, Osman Üstün, Ekrem Sezik, Yoshihisa Takaishi, Yukihisa Ono and Gisho Honda : Inhibitory effects of Turkish folk remedies on inflammatory cytokines: interleukin-1α, interleukin-1β and tumor necrosis factor α, Journal of Ethnopharmacology, Vol.58, No.1, 59-73, 1997.
(キーワード)
Turkish folk medicine / Interleukin-1 inhibition / Tumor necrosis factor inhibition
Yoshihisa Takaishi, Kaname Miyagi, Kazuyoshi Kawazoe, Kimiko Nakano, Kunhua Li and Hongquan Duan : Terpenoids from Tripterygium wilfordii var. regelii, Phytochemistry, Vol.45, No.5, 975-978, 1997.
Hongquan Duan, Kazuyoshi Kawazoe and Yoshihisa Takaishi : Sesquiterpene alkaloids from Tripterygium hypoglaucum and Tripterygium wilfordii: A New Class of Potent Anti-HIV Agents, Phytochemistry, Vol.45, No.3, 617-621, 1997.
Kimiko Nakano, Yoshiko Oose, Yuuko Masuda, Hikari Kamada and Yoshihisa Takaishi : A diterpenoid and triterpenes from tissue cultures of Tripterygium wilfordii, Phytochemistry, Vol.45, No.2, 293-296, 1997.
Ekrem Sezik, Erdem Yesilada, Mamoru Tabata, Gisho Honda, Yoshihisa Takaishi, Tetsuro Fujita, Toshihiro Tanaka and Yoshio Takeda : Traditional medicine in Turkey. VIII. Folk medicine in east Anatolia ; Erzurum, Erzincan, Agri, Kars, Igdir Provinces, Economic Botany, Vol.51, No.3, 195-211, 1997.
190.
Gisho Honda, Erdem Yeşilada, Mamoru Tabata, Ekrem Sezik, Tetsuro Fujita, Yoshio Takeda, Yoshihisa Takaishi and Toshihiro Tanaka : Traditional medicine in Turkey VI. Folk medicine in West Anatolia: Afyon, Kütahya, Denizli, Muğla, Aydin provinces, Journal of Ethnopharmacology, Vol.53, No.2, 75-87, 1996.
Mineo Niwa, Yasuyuki Tsutsumishita, Yumiko Kawai, Hideo Takahara, Noriko Nakamura, Shiroh Futaki, Yoshihisa Takaishi, Wataru Kondoh and Hideki Moritoki : Suppression of Inducible Nitric Oxide Synthase mRNA Expression by Tryptoquinone A, Biochemical and Biophysical Research Communications, Vol.224, No.2, 579-585, 1996.
(要約)
Triptoquinone A (TQA), which is an anti-inflammatory constituent in plants, was studied for its suppressive effect on nitric oxide production by LPS. TQA significantly suppressed smooth muscle relaxation and increase in cyclic GMP levels by nitric oxide (NO) in an L-arginine-induced relaxation experiment. The mechanistic studies showed that TQA did not directly inhibit NO radicals and inducible nitric oxide synthase (iNOS) enzyme but suppressed IL-1 beta and iNOS mRNA expression by LPS. The suppression level of iNOS gene expression by TQA was comparable to that by dexamethasone. TQA may be a useful candidate for the development of a drug as a potent inhibitor of iNOS gene over-expression.
Hideki Moritoki, Tetsuhiro Hisayama, Kann Kida, Wataru Kondoh, Shinnichi Inoue and Yoshihisa Takaishi : Inhibition by triptoquinone-A of LPS- and IL-1β-primed induction of no synthase in rat thoracic aorta, Life Sciences, Vol.59, No.3, PL49-PL54, 1996.
Kyoko Hayashi, Toshimitsu Hayashi, Kunie Ujita and Yoshihisa Takaishi : Characterization of antiviral activity of a sesquiterpene, triptofordin C-2, The Journal of Antimicrobial Chemotherapy, Vol.37, No.4, 759-768, 1996.
194.
Kimiko Nakano, Yuu Kanai, Ktaro Murakami and Yoshihisa Takaishi : Cucurbitacin glycosides from Caput nigri, Phytochemistry, Vol.39, No.1, 205-207, 1995.
Akira Iida, Y Tanaka, T Mihara, Mamoru Tabata, Gisho Honda, Tetsuro Shingu, Yoshio Takeda, Yoshihisa Takaishi, Erdem Yesilada, Ekrem Sezik and Tetsuro Fujita : Marrubinones A and B, New Labdane Diterpenoids from Marrubium astracanicum(Labiatae), Chemical & Pharmaceutical Bulletin, Vol.43, No.9, 1454-1457, 1995.
197.
Erdem Yesilada, Gisho Honda, Ekrem Sezik, Mamoru Tabata, Tetsuro Fujita, Toshihiro Tanaka, Yoshio Takeda and Yoshihisa Takaishi : Traditional medicine in Turkey. VII: Folk medicine in middle and west Black Sea regions, Economic Botany, Vol.49, No.4, 406-422, 1995.
(要約)
トルコ共和国黒海中西部沿岸の伝統薬について現地調査し，起源植物，用法などについて記述した．
198.
Kimiko Nakano, Yuu Kanai, Kotaro Murakami, Yoshihisa Takaishi and Toshiaki Tomimatsu : Nor-cucurbitacin glucosides from Caputo nigri, Phytochemistry, Vol.37, No.3, 817-820, 1994.
Hironori Sassa, Kentaro Kogure, Yoshihisa Takaishi and Hiroshi Terada : Structural basis of potent antiperoxidation activity of the triterpene celastrol in mitochondria: Effect of negative membrane surface charge on lipid peroxidation, Free Radical Biology and Medicine, Vol.17, No.3, 201-207, 1994.
Kozo Shishido, Kiyoto Goto, Shizuka Miyoshi, Yoshihisa Takaishi and Masayuki Shibuya : Synthetic studies on diterpenoid quinones with interleukin-1 inhibitory activity. Total synthesis of (.+-.)- and (+)-triptoquinone A, The Journal of Organic Chemistry, Vol.59, No.2, 406-414, 1994.
M. Okuda, A. Iida and Yoshihisa Takaishi : Fungal Metabolites X. The effect of Peptide Antibiotics, Trichosporins-Bs, on the Respiratory Activity of Mitochondria, Biological & Pharmaceutical Bulletin, Vol.17, 482-485, 1994.
203.
K. Matuura, O. Shoma and Yoshihisa Takaishi : Fungal Metabolites XV. Primary Structures of Antibiotic Peptides,Hypelcins B-I ,B-II ,B-III ,B-IV and B-V from Hypocrea peltata, Chemical & Pharmaceutical Bulletin, Vol.42, 1063-1069, 1994.
204.
Tetsuro Fujita, Yoshihisa Takaishi, Yoshio Takeda, Tetsuji Fujiyama and Takahito Nishi : Fungal metabolites. II. Structure elucidation of minor metabolites, valinotricin, cyclonerodiol oxide, and epicyclonerodiol oxide, from Trichoderma polysporum, Chemical & Pharmaceutical Bulletin, Vol.32, No.11, 4419-4425, 1984.
高石 喜久, Freddy A. Ramos, 田所 哲男, 竹内 実 : 玉葱皮に含まれる新規な抗菌・抗酸化化合物, New Food Industry, Vol.49, No.11, 1-8, 2007年11月.
国際会議:
1.
Sang-Yong Kim, Naonobu Tanaka, Yoshiki Kashiwada, Yoshihisa Takaishi, Jun'ichi Kobayashi and Mareshige Kojoma : Studies on the constituents of Chloranthus japonicus sieb., Planta Medica, Vol.80, 784, Oxford, Mississipi, USA, Aug. 2014.
Ishii Yasuyo, Kim Sang-Yong, Yoshihisa Takaishi and Yoshiki Kashiwada : Hydroxycinnamoyl 1,2-dihydro¬furo[3,2-e]tryptamine derivatives from defatted safflower seeds., International Congress on Natural Products Research, New York, Jul. 2012.
4.
Kurimoto Shin-ichiro, Pu Jian-Xin, Sun Han-Dong, Yoshihisa Takaishi and Yoshiki Kashiwada : Sesterterpenoids and diterpenoids from the aerial parts of Scutellaria coleifolia Levl, International Congress on Natural Products Research, New York, Jul. 2012.
5.
Sasaki Hisako, Sato Hisayo, Yoshiki Kashiwada, Kazuyoshi Kawazoe, Kotarou Murakami, Hirofumi Shibata, Sun Han-Dong, Li Shun-Lin and Yoshihisa Takaishi : Studies on the constituents of Cudrania tricuspidata, International Congress on Natural Products Research, New York, Jul. 2012.
6.
Kim Sang-Yong, Yoshiki Kashiwada, Kazuyoshi Kawazoe, Kotarou Murakami, Sun Han-Dong, Li Shun-Lin and Yoshihisa Takaishi : STUDIES ON THE CONSTITUENTS OF CHLORANTHUS SPICATUS (THUNB.) MAKINO, 2011 AMERICAN SOCIETY OF PHARMACOGNOSY ANNUAL MEETING, 74, San Diego, Aug. 2011.
7.
Sasaki Hisako, Yoshiki Kashiwada, Hirofumi Shibata and Yoshihisa Takaishi : STUDIES ON THE CONSTITUENTS OF DESMODIUM CAUDATUM, 2011 AMERICAN SOCIETY OF PHARMACOGNOSY ANNUAL MEETING, San Diego, Aug. 2011.
8.
Omichi Yuka, Kurimoto Shin-ichiro, Yoshiki Kashiwada, Hirofumi Shibata, Miyake Yoshiyuki, Kirimoto Tsukasa and Yoshihisa Takaishi : THE CONSTITUENTS OF THE FLOWER BUDS OF LONICERA JAPONICA AND THEIR ANTI-INFLUENZA ACTIVITIY, 2011 AMERICAN SOCIETY OF PHARMACOGNOSY ANNUAL MEETING, 66, San Diego, Aug. 2011.
9.
Yoshiki Kashiwada, Xiong Juan, Chen Chin-Ho, Qian Keduo, Morris-Natschke L. Susan, Lee Hsiung Kuo and Yoshihisa Takaishi : CONJUGATES OF BEVIRIMAT WITH BETURIN DERIVATIVES AS ANTI-HIV AGENTS, 2011 AMERICAN SOCIETY OF PHARMACOGNOSY ANNUAL MEETING, 66, Aug. 2011.
10.
Kurimoto Shin-ichiro, Yoshiki Kashiwada, Lee Kuo-Hsiung and Yoshihisa Takaishi : CHEMICAL STUDY ON DYSOXYLUM CUMINGIANUM (MELIACEAE), 2011 AMERICAN SOCIETY OF PHARMACOGNOSY ANNUAL MEETING, 58, San Diego, Jul. 2011.
11.
Daisuke Tsuji, T Koyama, Yoshiki Kashiwada, Yoshihisa Takaishi and Kouji Itou : Lycorine induces differentiation from embryonic stem cells into PSA-NCAM-positive cells, ICS2010, Chiba, Aug. 2010.
12.
Yoshihisa Takaishi, Yoshiki Kashiwada, Hashida Waka, Mikuchi Kousuke and Koichiro Tsuchiya : FERULOYL MUCIC ACID DERIVATIVES AS SIRT1 STUMULATOR FROM CITRUS SUDACHI HORT. EX SHIRAI., 50th Annual Meeting of the American Society of Pharmacognosy, Honolulu, Jun. 2009.
13.
Yoshiki Kashiwada, Xiong Juan, Kilgore R. Nicole, Wild T. Carl, Allaway P. Graham, Lee Kuo-Hsiung and Yoshihisa Takaishi : 3-O-ACYL BETULIN DERIVATIVE AND AZT CONJUGATE AS ANTI-HIV AGENTS., 50th Annual Meeting of the American Society of Pharmacognosy, Honolulu, Jun. 2009.
14.
Xiong Juan, Taniguchi Masatoshi, Yoshiki Kashiwada, Yamagishi Takashi and Yoshihisa Takaishi : AMIDE DERIVATIVES OF PAPYRIFERIC ACID AS MDR-REVERSING AGENTS., 50th Annual Meeting of the American Society of Pharmacognosy, Honolulu, Jun. 2009.
15.
Kim Sang-Yong, Yoshiki Kashiwada, Kazuyoshi Kawazoe, Kotarou Murakami, Sun Han-Dong, Li Shun-Lin and Yoshihisa Takaishi : STUDIES ON THE CONSTITUENTS OF CHLORANTHUS SPICATUS (THUNB.) MAKINO., 50th Annual Meeting of the American Society of Pharmacognosy, Honolulu, Jun. 2009.
16.
Kurimoto Shin-ichiro, Suzuki Kyoko, Yoshiki Kashiwada, Okasaka Mamoru, Kodzhimatov K. Olimjon and Yoshihisa Takaishi : STUDY ON MEDICINAL PLANTS OF UZBEKISTAN: CONSTITUENTS OF THE ROOTS OF FERULA VARIA (SCHRENK) TRAUTV., 50th Annual Meeting of the American Society of Pharmacognosy., Honolulu, Jun. 2009.
17.
Sang-Yong Kim, Yoshiki Kashiwada, Yoshihisa Takaishi, Kazuyoshi Kawazoe, Kotarou Murakami and Shun-Lin Li : Studies on the constituents of Chloranthus spicatus (Thumb.) Makino., 7th Joint Meeting of AFERP, ASP, GA, PSE&SIF, 1059, Athens, Aug. 2008.
18.
Yoshiki Kashiwada, Masatoshi Taniguchi, Xiong Juan, Takashi Yamagishi and Yoshihisa Takaishi : Triterpene derivatives and their reversing activity against multidrug resistant cancer cells., 7th Joint Meeting of AFERP, ASP, GA, PSE&SIF, Athens, Aug. 2008.
成相 祐希, Hiroyuki Mizuguchi, 永井 浩章, 金山 知代, 加藤 周平, Yoshiyuki Yoshimura, Yoshiki Kashiwada, Hisao Nemoto, Yoshihisa Takaishi, Noriaki Takeda and Hiroyuki Fukui : Identification of the target molecule of the new anti-allergic compound, maackiain from Kujin, 第85回日本薬理学会年会, Mar. 2012.
熊 娟, 柏田 良樹, Chen Chin-Ho, Lee Kuo-Hsiung, 高石 喜久 : Research on Anti-HIV Natural Products (25) –Betulin Derivatives and AZT conjugates as Anti-HIV Agents with Multi-Mechanisms of Action-, 日本薬学会第130年会, No.2, 222, 2010年3月.
柏田 良樹, 熊 娟, R. Nicole Kirgore, T. Carl Wirl, P. Graham Allaway, Kuo-Hsiung Lee, 高石 喜久 : 抗HIV天然物に関する研究 (23) -ベツリンをリードとしたマルチメカニズムな抗HIV活性分子の創成研究-, 日本薬学会第129年会, No.2, 226, 2009年3月.
109.
熊 娟, 谷口 昌聖, 柏田 良樹, 山岸 喬, 高石 喜久 : Research on Plant-Derived MDR-Reversing Agents (7): Amide Derivatives of Papyriferic Acid as MDR-reversing Agents., 日本薬学会第129年会, No.2, 227, 2009年3月.
柏田 良樹, 高石 喜久, Kilgore R. Nicole, Wild T. Carl, Allaway P. Graham, Lee Kuo-Hsiung : 抗HIV天然物に関する研究(20)-3-O-Glutaryl-betulin及び-dihydrobetulin ester誘導体の抗HIV活性―, 日本薬学会第127年会, 2007年3月.
Tomihiko Higuti, Hirofumi Shibata, Youichi Sato, Yoshihisa Takaishi, Kazuyoshi Kawazoe and Kotaro Murakami : Medical composition for treating infection with drugresistant Staphylococcus aureus, PIXXD2 WO 2004066992 A1 20040812 CAN 141:167738 AN 2004:648378 CAPLUS (Apr. 2004).