Isolation, structure elucidatiion and biosynthesis of biologically active natural products (natural medicine, traditional medicine, biologically active substance, structure elucidation) (On the constituents of traditional medicine in Turkic people and related plants. On the constituents of plants grown under subtropical climate.)
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Book:
1.
井上 博之, 上田 伸一, 井上 謙一郎 and Yoshio Takeda : 天然物化学, 株式会社 廣川書店, Tokyo, 1976.
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.
(Summary)
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.
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.
(Summary)
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.
Otsuka Hideaki, Shitamoto Junko, He Dong-Hui, Matsunami Katsuyoshi, Shinzato Takakazu, Aramoto Mitsunori, Yoshio Takeda and Kanchanapoom Tripetch : Tricalysioside P-U: Ent-kaurane glucosides and a labdane glucoside from leaves of Tricalysia dubia Ohwi, Chemical & Pharmaceutical Bulletin, Vol.55, No.11, 1600-1605, 2007.
(Summary)
Further extensive isolation work on the 1-BuOH-soluble fraction of a MeOH extract of Tricalysia dubia afforded five new ent-kaurane glucosides (4-8) and one new labdane glucoside (9), together with a known megastigmane glucoside, sammangaoside B (1), and monoterpene glucosides (2, 3). The structures of the new compounds were elucidated by analyses of one- and two-dimensional NMR spectroscopic data. The absolute configuration of the 9-position of sammangaoside B was revised to S and its total stereochemistry was established by the modified Mosher's method.
Dong-Hui He, Katsuyoshi Matsunami, Hideaki Otsuka, Takakazu Shinzato, Mitsunori Aramoto, Masahiko Bando and Yoshio Takeda : Tricalysiolide G and tricalysiols A and B:rearranged ent-kaurane-type and ent-kaurane-type diterpenoids from the leaves of Tricalysia dubia (Lindl.) Ohwi, Journal of Natural Medicines, Vol.61, No.1, 46-50, 2007.
Stevia (<I>Stevia rebaudiana</I>), a well-known sweet herb, has been reported to have potent antioxidant activity. Methanolic extract of Stevia was fractionated and subsequently purified according to the results of DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging assay, producing three active compounds. Structural analysis of these compounds revealed that they were 3,4-dicaffeolylquinic acid, 3,5-dicaffeolylquinic acid and quercetin-3-O-α-rhamnopyranoside. Their antioxidant activity was measured using a radical initiator AAPH 2,2'-azobis(2-amidinopropane)hydrochloride -induced lipid oxidation system. While their activity was not as high as that of trolox, the three isolated compounds exhibited potent antioxidant activity at a concentration of 60μmol/l.
From the leaves of Helicia cochinchinensis, collected on Okinawa Island, seven phenolic glucosides and two terpenic glucosides were isolated. Five of the phenolic glucosides were previously known, being identified with p-coumaric and ferulic acids glucosyl esters, rhodioloside, helicidiol, and naringenin 5-O-beta-D-glucopyranoside. The structures of two other phenolic glucosides, named heliciosides A and B, were elucidated to be 5-O-beta-D-glucosides of 3-hydroxyflavanone, namely aromadendrin and taxifolin, by means of spectroscopic analyses. The two terpenic glucosides were identified with ampelopsisionoside and icariside C1.
Etsuko Sueyoshi, Hui Liu, Katsuyoshi Matsunami, Hideaki Otsuka, Takakazu Shinzato, Mitsunori Aramoto and Yoshio Takeda : Bridelionosides A-F:Megastigmane glucosides from Bridelia glauca f. balansae, Phytochemistry, Vol.67, No.22, 2483-2493, 2006.
(Summary)
The chemical investigation of leaves of Bridelia glauca f. balansae afforded six megastigmane glucosides, named bridelionosides A-F, along with seven known megastigmane glucosides. Their structures were determined by a combination of spectroscopic analyses and by application of the modified Mosher's method.
Katsuyoshi Matsunami, Ichiko Takamori, Takakazu Shinzato, Mitsunori Aramoto, Kazunari Kondo, Hideaki Otsuka and Yoshio Takeda : Radical-scavenging activities of new megastigmane glucosides from Macaranga tanarius (L.)Muelll.-Arg., Chemical & Pharmaceutical Bulletin, Vol.54, No.10, 1403-1407, 2006.
(Summary)
Four new megastigmane glucosides, named macarangiosides A-D (2-5), together with mallophenol B, lauroside E, methyl brevifolin carboxylate, and hyperin and isoquercitrin as a mixture were isolated from the leaves of Macaranga tanarius (L.) MULL.-ARG. (Euphorbiaceae). Their structures were elucidated by spectroscopic and chemical analyses. Macarangioside A-C (2-4) and mallophenol B were galloylated on glucose moiety and possessed the potent 2,2-diphenyl-picrylhydrazyl (DPPH) radical-scavenging activity.
Dong-Hui He, Katsuyoshi Matsunami, Hideaki Otsuka, Takakazu Shinzato, Mitsunori Aramoto, Masahiko Bando and Yoshio Takeda : Tricalysiosides H-O:Ent-kaurane glucosides from the leaves of Tricalysia dubia, Phytochemistry, Vol.66, No.24, 2857-2864, 2005.
(Summary)
Eight ent-kaurane glucosides, named tricalysiosides H-O, were isolated from Tricalysia dubia. Tricalysioside H possessed a hydroxyl group at the 1-position, to which the glucose moiety was attached. The structure was first elucidated by means of spectroscopic data analysis and finally confirmed by X-ray crystallography. Since acid hydrolysis of 1 gave D-glucose, the aglycone was proved to have an enantio-kaurane type skeleton. The structures of tricalysiosides I-O were mainly elucidated from analysis of spectroscopic evidence.
Toshiya Masuda, Takuya Kirikihira and Yoshio Takeda : Recovery of Antioxidant Activity from Carnosol Quinone: Antioxidants Obtained from a Water-Promoted Conversion of Carnosol Quinone, Journal of Agricultural and Food Chemistry, Vol.53, No.17, 6831-6834, 2005.
(Summary)
Carnosol is one of the main antioxidants in sage and rosemary. Although carnosol quinone is the antioxidation product of carnosol and has a very weak antioxidant activity, its treatment in water-containing solvent restored its strong antioxidant activity. HPLC analysis of the water-stimulated recovery reaction of the antioxidant activity revealed that the strong activity was due to the reproduced carnosol. The analysis also showed that an almost equal amount of quinone derivatives of rosmanol (rosmanol quinone) was produced in the reaction along with the carnosol. The rosmanol was formed by the addition of 1 equiv of water and the following isomerization from carnosol quinone in the water-containing solvent. The formed rosmanol was also found to be oxidized by the remaining carnosol quinone to produce rosmanol quinone. At the same time, carnosol quinone was reduced to afford carnosol. This redox phenomenon is an important part of the mechanism for the recovery of the antioxidant activity from carnosol quinone under the water-containing conditions.
(Keyword)
Acetonitriles / Antioxidants / Benzoquinones / Chromatography, High Pressure Liquid / Diterpenes, Abietane / oxidation and reduction / Phenanthrenes / Rosmarinus / Salvia officinalis / Solvents / Water
Qian Yu, Katsuyoshi Matsunami, Hideaki Otsuka and Yoshio Takeda : Staphylionosides A-K: Megastigmane Glucosides from the Leaves of Staphylea bumalda DC., Chemical & Pharmaceutical Bulletin, Vol.53, No.7, 800-807, 2005.
(Summary)
Chemical investigation of leaves of Staphylea bumalda DC., collected in the suburbs of Hiroshima City, afforded 11 new megastigmane glucosides, named staphylionosides A-K (3-13), along with two known megastigmane glucosides (1, 2). The relative structures were elucidated from spectroscopic evidence, and the absolute structures of the aglycones were determined by means of the combination of beta-D-glucosylation-induced shift-trends and the modified Mosher's method.
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.
(Summary)
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.
Toshiya Masuda, Daiki Yamashita, Yoshio Takeda and Shigetomo Yonemori : Screening for Tyrosinase Inhibitors among Extracts of Seashore Plants and Identification of Potent Inhibitors from Garcinia subelliptica, Bioscience, Biotechnology, and Biochemistry, Vol.69, No.1, 197-201, 2005.
(Summary)
The tyrosinase inhibitory activity of methanol extracts of the leaves of 39 plant species growing on the seashore of Iriomote island (Okinawa, Japan) was investigated. The extracts of Hibiscus tiliaceus, Carex pumila, and Garcinia subelliptica showed potent activity among them. The inhibitors in the extract of Garcinia subelliptica were purified by assay-guided fractionation to give two biflavonoids. These were known compounds (2R,3S-5,7,4',5'',7'',3''',4'''-heptahydroxy flavanone[3-8''] flavone and 5,7,4',5'',7'',3''',4'''-heptahydroxy[3-8''] biflavanone), although their strong inhibitory activity toward tyrosinase is revealed for the first time in this work. One of these biflavonoids (2R,3S-5,7,4',5'',7'',3''',4'''-heptahydroxy flavanone[3-8''] flavone) showed much stronger activity (IC50 2.5 microM) than that of kojic acid (IC50 9.1 microM) when L-tyrosine was used as the substrate.
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.
(Summary)
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.
Toshiya Masuda, Takuya Kirikihira, Yoshio Takeda and Shigetomo Yonemori : Thermal recovery of antioxidant activity from carnosol quinone, the main antioxidation product of carnosol, Journal of the Science of Food and Agriculture, Vol.84, No.11, 1421-1427, 2004.
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.
(Summary)
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.
(Keyword)
Uzbekistan / Folk medicine / Toshkent / Samarqand / Djizzax
Hideaki Otsuka, Yoshio Takeda, Eiji Hirata, Takakazu Shinzato and Masahiko Bando : Glochidiolide, isoglochidiolide, acuminaminoside, and glochidacuminosides A-D from the leaves of Glochidion acuminatum MUELL., Chemical & Pharmaceutical Bulletin, Vol.52, No.5, 591-596, 2004.
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.
Toshiya Masuda, Yasuo Oyama, Natsuko Ymamamoto, Chisato Umebayashi, Hiromi Nakao, Yukiko Toi, Yoshio Takeda, Katsuo Nakamoto, Hideki Kuninaga, Yukari NIshizato and Akira Nonaka : Cytotoxic Screening of Medicinal and Edible Plants in Okinawa, Japan, and Identification of the Main Toxic Constituent of Rhodea japonica (Omoto), Bioscience, Biotechnology, and Biochemistry, Vol.67, No.6, 1401-1404, 2003.
(Summary)
The cytotoxic activity of ethanol extracts from 53 parts of 36 species of medicinal and edible plants cultivated in Okinawa was measured by using K562 human leukemia cells by a flow cytometric method. Two extracts from Rhodea japonica and Hypericum chinense were cytotoxic at a concentration of 10 microg/ml. The main cytotoxic constituent of Rhodea japonica was isolated and identified to be rhodexin A, which has been isolated as a cardetonic agent of the plant. The IC(50) value for rhodexin A against the growth of K562 cells was 19 nM, this activity being much stronger than that of ouabain (IC(50), 60 nM).
Toshiya Masuda, Yuzuru Inaba, Tomomi Maekawa, Yoshio Takeda, Hidemasa Yamaguchi, Katsuo Nakamoto, Hideki KUninaga, Saori NIshizato and Akira Nonaka : A Simple Detection Method of Powerful Antiradical Compounds in the Raw Extract of Plants and Its Application for the Identification of Antiraducal Plant Constituents, Journal of Agricultural and Food Chemistry, Vol.51, No.7, 1831-1838, 2003.
(Summary)
A simple detection method for a powerful radical scavenging compound in a mixture containing a large variety of compounds, such as the raw extract of edible plants, was developed using 1,1-diphenyl-2-picrylhydrazyl (DPPH) as the radical reagent. The method was established on the basis of the features of the typical chain-breaking antioxidation reaction mechanism, which suggests that the radical scavenging antioxidant should be converted to other stable nonradical compounds during the reaction. This method requires only a simple HPLC instrument, and the disappearance or decrease in the peak intensity, which is induced by the addition of DPPH. This change is monitored by the HPLC to detect the powerful radical scavenger from the complex mixture. The method was applied to the detection and identification of the most powerful antiradical compound in the extracts of three antioxidatively active plant extracts (Psidium guajava, Citrus depressa, and Hypericum chinense). The radical scavenging efficiency of a newly identified compound from H. chinense was also compared with that of Trolox and catechin using the method.
Majekodunmi Oladeji Fatope, Khamis S Suad Al-Burtomani, John O Ochei, Abdulrahman O Abdulnour, Z Salma M Al-Kindy and Yoshio Takeda : Muscanone:a 3-O-(1",8",14"-trimenyl)naringenin from Commiphora, Phytochemistry, Vol.62, No.8, 1251-1255, 2003.
Nahoko Uchiyama, Fumiyuki Kiuchi, Michiho Ito, Gisho Honda, Yoshio Takeda, Olimjon K Khodzhimatov and Ozodbek A Ashurmetov : New icetexane and 20 norabietane diterpenes with trypanocidal activity from Dracocephalum komarovi., Journal of Natural Products, Vol.66, No.1, 128-131, 2003.
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.
(Summary)
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.
Majekodunmi Oladeji Fatope, Labaran Salihu, Stephen K Asante and Yoshio Takeda : Larvicidal activity of extract and triterpenoids from Lantana camara, Pharmaceutical Biology, Vol.40, No.8, 564-567, 2002.
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.
(Summary)
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.
Yoshio Takeda, Natsuko Isai, Toshiya Masuda, Hideaki Otsuka, Gisho Honda, Yoshihisa Takaishi, Fumiyuki Kiuchi, Michiho Ito, Ozodebek A Ashurmetov and Olimjon K Khodzhimatov : A new megastigmane glucoside from Phlomis spinidens, Natural Medicines, Vol.56, No.5, 200-203, 2002.
(Summary)
A new megastigmane glucoside, phlomisionoside (1) was isolated from the aerial parts of Phlomis spinidens and the structure was elucidated by spectroscopic and chemical analyses.
Toshiya Masuda, Yukiko Toi, Hiromi Bando, Tomomi Maekawa, Yoshio Takeda and Hidemasa Yamaguchi : Structural Identification of New Curcumin Dimers and Their Contribution to the Antioxidant Mechanism, Journal of Agricultural and Food Chemistry, Vol.50, No.9, 2524-2530, 2002.
(Summary)
As a part of the research project on the elucidation of the chain-breaking antioxidant mechanism of natural phenolics against the oxidation of food components, curcumin, a main turmeric pigment, was investigated. A relatively high concentration of curcumin gave three dimers as radical termination products in addition to the coupling products with curcumin and the lipid hydroperoxide. The structural analysis of these dimers and quantitative analysis of their production rates revealed that radical-radical termination mainly occurred at the 2-position of curcumin. The contribution of the pathway for production of these dimers to the antioxidant mechanism of curcumin was estimated from the concentration-dependent data of the antioxidant activity and formation rates of these termination products. The A-A termination (dimer formation) was estimated to contribute at least about 40% of the entire antioxidant process against ethyl linoleate oxidation.
Dong-Hui He, Hideaki Otsuka, Eiji Hirata, Takakazu Shinzato, Masahiko Bando and Yoshio Takeda : Tricalysiosides A-G; Rearranged ent-kaurenoid glycosides from the leaves of Tricalysia dubia, Journal of Natural Products, Vol.65, No.5, 685-688, 2002.
(Summary)
Seven rearranged ent-kaurane glycosides, named tricalysiosides A-G (1-7), were isolated from the leaves of Tricalysia dubia collected on Okinawa Island. Their C-18 and 19 methyls were found to have rearranged to form an alpha,beta-unsaturated gamma-lactone ring, with other functional groups remotely located only on C-15, -16, and -17 of the five-membered ring. Information available from various kinds of two-dimensional NMR spectra was limited and insufficient to allow total characterization of the structures. Finally, using X-ray crystallographic analysis, the structure of tricalysioside A (1) was determined to be 4-nor-18-homo-ent-kauran-4(18)-en-15beta,16beta,17-triol-3beta,19-olide 16-O-beta-D-glucopyranoside (1). On the basis of the crystal structure of 1, the structures of the other tricalysiosides (2-7) were also established.
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.
(Summary)
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).
Kyoko Hayashi, Toshimitsu Hayashi, Han-dong Sun and Yoshio Takeda : Contribution of a combination of ponicidin and acyclovir/gancyclovir to the antitumor effifiency of the herpes simplex virus thymidine kinase gene therapy system, Human Gene Therapy, Vol.13, No.3, 415-423, 2002.
Toshiya Masuda, Yasuo Oyama, Shigetomo Yonemori, Yoshio Takeda, Yuko Yamanazaki, Shinichi Mizuguchi, Mami Nakata and Tomochika Tanaka : Flow Cytometric Estimation on Cytotoxic Activity of Leaf Extracts from Seashore Plants in Subtropical Japan: Isolation, Quantification and Cytotoxic Action of (-)-Deoxypodpphyllotoxin, Phytotherapy Research, Vol.16, No.4, 353-358, 2002.
(Summary)
The cytotoxic activity of methanol extracts of leaves collected from 39 seashore plants in Iriomote Island, subtropical Japan was examined on human leukaemia cells (K562 cells) using a flow cytometer with two fluorescent probes, ethidium bromide and annexin V-FITC. Five extracts (10 microg/mL) from Hernandia nymphaeaefolia, Cerbera manghas, Pongamia pinnata, Morus australis var. glabra and Thespesia populnea greatly inhibited the growth of K562 cells. When the concentration was decreased to 1 microg/mL, only one extract from H. nymphaeaefolia still inhibited the cell growth. A cytotoxic compound was isolated from the leaves by bioassay-guided fractionation and was identified as (-)-deoxypodophyllotoxin (DPT). The fresh leaves of H. nymphaeaefolia contained a remarkably high amount of DPT (0.21 +/- 0.07% of fresh leaf weight), being clarified by a quantitative HPLC analysis. DPT at 70-80 pM started to inhibit the growth of K562 cells in an all-or-none fashion and at 100 pM or more it produced complete inhibition in all cases. Therefore, the slope of the dose-response curve was very steep. DPT at 100 pM or more decreased the cell viability to 50%-60% and increased the number of cells undergoing apoptosis (annexin V-positive cells). The results indicate that DPT contributes to the cytotoxic action of the extract from the leaves of H. nymphaeaefolia on K562 cells.
Toshiya Masuda, Yuzuru Inaba, Tomomi Maekawa, Yoshio Takeda, Tadatoshi Tamura and Hidemasa Yamaguchi : Recovery Mechanism of the Antioxidant Activity from Carnosic Acid Quinone, an Oxidized Sage and Rosemary Antioxidant, Journal of Agricultural and Food Chemistry, Vol.50, No.21, 5863-5869, 2002.
(Summary)
A solution of carnosic acid quinone, which is a radical chain-termination product having no antioxidant activity in the antioxidant reaction of carnosic acid, recovers potent antioxidant activity upon standing. The HPLC analysis of an aged solution of carnosic acid quinone revealed that several antioxidants are produced in the solution. From the time-course and quantitative analyses of the formation of the products and their structural analysis, an antioxidant mechanism from carnosic acid quinone is proposed that includes a redox reaction of carnosic acid quinone in addition to the isomerization to lactone derivatives. In the first stage of antioxidation, carnosic acid, the reduction product from carnosic acid quinone, contributes to the potent antioxidant activity of the solution. This proposed mechanism can explain one of the reasons for the strong antioxidant activity of the extract of the popular herbs sage and rosemary.
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.
(Summary)
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.
(Keyword)
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.
(Summary)
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.
(Summary)
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．
56.
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.
(Summary)
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.
Hideaki Otsuka, Eiji Hirata, Takakazu Shinzato and Yoshio Takeda : Glochiflavanosides A-D:flavanol glucosides from the leaves of Glochidion zeylanicum (Gaertn.) A Juss., Chemical & Pharmaceutical Bulletin, Vol.49, No.7, 921-923, 2001.
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.
(Summary)
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.
Toshiya Masuda, Kumiko Iritani, Shigetomo Yonemori, Yasuo Oyama and Yoshio Takeda : Isolation and Antioxidant Activity of the Galloyl Flavonol Glycosides from a Seashore Plant, Pemphis acidula, Bioscience, Biotechnology, and Biochemistry, Vol.65, No.6, 1302-1309, 2001.
(Summary)
Four kinds of galloyl flavonol glycosides were found in the leaf extract of Pemphis acidula, a plant growing on the subtropical seashore. Their chemical structures were elucidated to be quercetin or kaempferol 6"-O-galloyl-beta-D-glycosides by using spectroscopic and chemical analyses. One of the flavonols, kaempferol-3-O-(6-O-galloyl-beta-D-galactopyranoside), was newly isolated from natural sources and its structure was completely determined in this investigation. The antioxidant-related activities of the galloyl flavonoids were examined by the DPPH antiradical activity, inhibition of methyl linoleate oxidation, and inhibition of oxidative cell death. These results were compared with those of the corresponding non-galloylated flavonol glycosides and their aglycones. The galloyl flavonoids showed more efficient activity than that of the corresponding flavonol glycosides, but not more than that of the corresponding aglycones in the three assays applied.
(Keyword)
Africa / Animals / Antioxidants / Bepridil / Biphenyl Compounds / Brain / Cell Death / Chromatography, High Pressure Liquid / Flavonoids / Gallic Acid / Glycosides / Hydrolysis / Magnetic Resonance Spectroscopy / Male / Oxidation-Reduction / Pacific Islands / Picrates / Plant Leaves / Plants / Rats
Toshiya Masuda, Yuzuru Inaba and Yoshio Takeda : Antioxidant Mechanism of Carnosic Acid: Structural Identification of Two Oxidation Products, Journal of Agricultural and Food Chemistry, Vol.49, No.11, 5560-5565, 2001.
(Summary)
To determine the antioxidant mechanism of food phenolics against the oxidation of food components, the reaction of carnosic acid, an antioxidative constituent of the popular herbs sage and rosemary, was investigated in the presence of ethyl linoleate and the radical oxidation initiator 2,2'-azobis(2,4-dimethylvaleronitrile). During this process, carnosic acid was oxidized to an o-quinone and a hydroxy p-quinone, the chemical structures of which were confirmed by physical and chemical techniques. From a quantitative time course analysis of the production of these quinones, an antioxidant mechanism of carnosic acid is proposed, consisting of the oxidative coupling reaction with the peroxyl radical at the 12- or 14-position of carnosic acid and subsequent degradation reactions.
Toshiya Masuda, Tomomi Moekawa, Kayo Hidaka, Hiromi Bando, Yoshio Takeda and Hidemasa Yamaguchi : Chemical Studies on Antioxidant Mechanism of Curcumin: Analysis of Oxidative Coupling Products from Curcumin and Linoleate, Journal of Agricultural and Food Chemistry, Vol.49, No.5, 2539-2547, 2001.
(Summary)
As a part of a research project on the antioxidant mechanism of natural phenolics in food components, curcumin, a turmeric antioxidant, was investigated in the presence of ethyl linoleate as one of the polyunsaturated lipids. During the antioxidation process, curcumin reacted with four types of linoleate peroxyl radicals. Six reaction products were observed in the reaction and subsequently isolated. Their structures were determined by physical techniques, revealing that they have novel tricyclic structures, including a peroxyl linkage. On the basis of the formation pathway for their chemical structures, an antioxidant mechanism of curcumin in polyunsaturated lipids was proposed, which consisted of an oxidative coupling reaction at the 3'-position of the curcumin with the lipid and a subsequent intramolecular Diels--Alder reaction.
(Keyword)
Antioxidants / Chromatography, High Pressure Liquid / Coloring Agents / Curcumin / Linoleic Acid / oxidation and reduction / Peroxides
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.
(Summary)
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.
(Summary)
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.
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.
(Summary)
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.
(Summary)
Traditional medicine used in Central Anatolia; Ankara, Kayseri, Niğde and south-eastern parts of Karaman and Konya provinces have been studied. Two hundred and ninety one folk remedies obtained from 103 plant species belonging to 40 families and 4 animal species are reported with their vernacular names, parts used, methods of preparing remedies and therapeutic usage.
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.
(Summary)
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.
(Keyword)
Ferula kuhistanica / Umbelliferae / Sesquiterpenes / Daucane esters / Kuhistanicaol A G
Toshiya Masuda, Hiromi Bando, Tomomi Maekawa, Yoshio Takeda and Hidemasa Yamaguchi : A Novel Radical Terminated Compound Produced in the Antioxidation Process of Curcumin against Oxidation of a Fatty Acid Ester, Tetrahedron Letters, Vol.41, No.13, 2157-2160, 2000.
Hideaki Otsuka, Eiji Hirata and Yoshio Takeda : Isolation of lignan glucoside and neolignan sulfate from the leaves of Glochidion zeylanicum (Gaertn) A. Juss., Chemical & Pharmaceutical Bulletin, Vol.48, No.7, 1084-1086, 2000.
Toshiya Masuda, Shinichi Mizuguchi, Tomochika Tanaka, Kumiko Iritani, Yoshio Takeda and Sigetomo Yonemori : Isolation and Structure Determination of New Antioxidative Ferulic Acid Glucoside Esters from the Rhizomes of Alpinia speciosa, a Zingiberaceae Plant Used in Okinawan Food Culture, Journal of Agricultural and Food Chemistry, Vol.48, No.5, 1479-1484, 2000.
(Summary)
An assay-guided isolation gave three antioxidants including two newly identified compounds from the rhizomes of Alpinia speciosa, which is used as an important plant in the food culture of the Okinawa area of Japan. Spectroscopic analysis of the two new compounds revealed them to be new glucoside esters of ferulic acid. The antioxidant activity of the esters was measured using two different methods. Both compounds showed greater activity than that of Trolox in the TLC method; however, one of the compounds showed weaker inhibitory activity than that of Trolox and epicatechin against AMVN-induced methyl linoleate oxidation.
Yoshio Takeda, Yoshihiro Okada, Toshiya Masuda, Eiji Hirata, Anki Takushi, Qian Yu and Hideaki Otsuka : A new mwgastigmane and a new tetraketide from leaves of Euscaphis japonica, Chemical & Pharmaceutical Bulletin, Vol.48, No.5, 752-754, 2000.
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.
(Summary)
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.
From the aerial parts of Phlomis rigida, three iridoid glucosides, phlorigidoside A (2-O-acetyllamiridoside), B (8-O-acetyl-6-beta-hydroxyipolamide) and C (5-deoxysesamoside), were isolated together with the known iridoid glucosides, shanzhiside methyl ester, 8-O-acetylshanzhiside methyl ester, deoxypulcheloside I, lamiridoside, and 6-beta-hydroxyipolamide. The structures of the new compounds were elucidated based on spectral and chemical evidence.
Hirokazu Sudo, Toshinori Ide, Hideaki Otsuka, Eiji Hirata, Anki Takushi and Yoshio Takeda : Megastigmane, benzyl and phenethyl alcohol glycosides, and 4,4`-dimethoxytruxinic acid catalpol diester from the leaves of Premna subscandens, Chemical & Pharmaceutical Bulletin, Vol.48, No.4, 542-546, 2000.
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.
(Summary)
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.
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.
(Summary)
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.
(Keyword)
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.
(Summary)
[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.
(Keyword)
Dimerization / Inula / Magnetic Resonance Spectroscopy / Mass Spectrometry / Molecular Structure / Terpenes / Trees
S. Kumar, O.P. Sati, V.D. Semwal, M. Nautial and Yoshio Takeda : Iridoid glycosides from Lonicera quinquelocularis, Phytochemistry, Vol.53, No.4, 499-501, 2000.
(Summary)
A new iridoid glycoside 6'-O-beta-apiofuranosylsweroside was isolated from the ethanolic extract of the roots of Lonicera quinquelocularis along with the known compounds loganin and sweroside.
Yoshio Takeda, Hideko Shimidzu, Toshiya Masuda, Eiji Hirata, Anki Takushi, Takakazu Shinzato and Hideaki Otsuka : A new phenylpropanoid-glycerol conjugate from Helitiera littoralis Dryand, Natural Medicines, Vol.54, No.1, 22-25, 2000.
(Summary)
From the leaves of Helitiera littoralis, a new phenylpropanoid-glycerolconjugate was isolated together with known compounds, isolariciresinol-3a-O-β-D-glucoside, (Z)-3-hexenyl β-D-glucoside, methyl [β-D-xylopyranosyl-(1→6)-β-D-glucopyranosyl]-salicylate, afzelin, astragalin, quercitrin and tribuloside. The structure of the new compound was elucidated as 2-O-[4'-(3"-hydroxypropyl)-2',5'-dimethoxyphenyl]-1-O-β-D-glucopyranosylglycerol by spectral and chemical evidence.
Kyoko Hayashi, Toshimitsu Hayashi, Han-dong Sun and Yoshio Takeda : Potentiation of ganciclovir toxity in herpes simplex virus thymidine kinase/ganciclovir administration system by ponicidin, Cancer Gene Therapy, Vol.7, No.1, 45-52, 2000.
Yoshio Takeda, Hiroyuki Morikawa, Toshiya Masuda, Eiji Hirata, Takakazu Shinnzato and Hideaki Otsuka : New sesquiterpene glucosides from Crepidiastrum lanceolatum, Natural Medicines, Vol.56, No.2, 51-54, 2000.
(Summary)
From the underground parts of Crepidiastrum lanceolatum, two new sesquiterpene glucoside p-hydroxyphenylacetic acid esters, crepidialanceosides A and B, were isolated together with two known compounds, youngiaside D and sonchuside A. The structures of new compounds were elucidated based on spectral analyses and chemical evidence.
(Keyword)
Crepidiastrum lanceolatum / Asteraceae / crepidialanceosides A and B / sesquiterpene glucoside p-hydroxyphenylacetic acid ester / guaiane
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.
(Summary)
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.
Yoshio Takeda, Yoshihiro Okada, Toshiya Masuda, Eiji Hirata, Anki Takushi and Hideaki Otsuka : Euscapholide and its Glucoside from Leaves of Euscaphis japanica, Phytochemistry, Vol.49, No.8, 2565-2568, 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.
(Summary)
Folk medicine in northwest Anatolia has been studied and 116 remedies prepared from 67 plant and 8 animal species are described, each with vernacular names, methods of preparation and traditional uses.
(Keyword)
Northwest Anatolia / Traditional medicine / Turkey
Toshiya Masuda, Kayo Hidaka, Ayumi Shinohara, Tomomi Maekawa and Yoshio Takeda : Chemical Studies on Antioxidant Mechanism of Curcuminoid: Analysis of Radical Reaction Products from Curcumin, Journal of Agricultural and Food Chemistry, Vol.47, No.1, 71-77, 1999.
Hirokazu Sudo, Toshinori Ide, Hideaki Otsuka, Eiji Hirata, Anki Takushi and Yoshio Takeda : Iridoid glucosides with different acyl moieties from globurarinin and globularimin, Phytochemistry, Vol.49, No.3, 783-786, 1998.
Yoshio Takeda, Toshiya Masuda, Takashi Matsumoto, Yuusuke Takechi, Tetsurou Shingu and Heinz G Floss : Nuclear magnetic resonance and biosynthetic studies of neoantimycin and structure elucidation of isoneoantimycin, a minor metabolite related to neoantimycin, Journal of Natural Products, Vol.61, No.8, 978-981, 1998.
(Summary)
In preparation for biosynthetic studies on the 3,4-dihydroxy-2, 6-dimethyl-5-phenylvaleric acid portion of neoantimycin (1), the 1H and 13C NMR signals of 1 were assigned unambiguously by means of 2D correlation spectroscopy and NOE experiments. The previously undetermined absolute stereochemistry at C-15 and C-16 was deduced as (S) and (S). The structure of isoneoantimycin (2) was also elucidated. The methyl groups of methionine and propionate were incorporated stereospecifically into C-13 and C-12 of 1, respectively, and the configuration of the methyl group of methionine is inverted in the process. The results also suggest the intervention of phenylpyruvate as an actual precursor.
Toshiya Masuda, Hiroyuki Matsumura, Yasuo Oyama, Yoshio Takeda, Akiko Jitoe, Atsuko Kida and Kayo Hidaka : Synthesis of (+-)-Cassumunins A and B, New Curcuminoid Antioxidants Having Protective Activity of the Living Cell against Oxidative Damage, Journal of Natural Products, Vol.61, No.5, 609-613, 1998.
105.
Yoshio Takeda, Akiko Takechi, Toshiya Masuda and Hideaki Otsuka : An acyclic monoterpene glucosyl ester from Lantana lilacia, Planta Medica, Vol.64, No.1, 78-79, 1998.
Yoshio Takeda, Chieko Mima, Toshiya Masuda, Eiji Hirata, Anki Takushi and Hideaki Otsuka : Glochidioboside, a glucoside of (7S,8R)-dihydrodehydroconiferyl alcohol from leaves of Glochidion obovatum, Phytochemistry, Vol.49, No.7, 2137-2139, 1998.
Basma A. A. A. Balboul, Ahmed A. Ahmed, Hideaki Otsuka, Masahiko Bando, Masaru Kido and Yoshio Takeda : A guaianolide and a germacranolide from Achillea santolina, Phytochemistry, Vol.46, No.6, 1045-1049, 1997.
Hirokazu Sudo, Anki Takushi, Toshinori Ide, Hideaki Otsuka, Eiji Hirata and Yoshio Takeda : Premethanosides A and B, phenylethanoids from leaves of Premna subscabdebs, Phytochemistry, Vol.46, No.6, 1147-1150, 1997.
(Summary)
Premna subscandens葉部より，4種の既知phenyethanoid配糖体と共に，2種の新phenylethanoid配糖体，premnethanosides A, Bを単離し，その化学構造を明らかにした．
114.
Toshiya Masuda, Akiko Jitoe, Atsuko Kida and Yoshio Takeda : Synthesis of Cassumunin A, a Potent Antiinnflamatory Antioxidant from a Medicinal Ginger, Zingiber cassumunar, Natural Products Letters, Vol.10, 13-16, 1997.
トルコ産シソ科植物Salvia nemorosa地上部の配糖体成分を検索し，5種の既知化合物を同定すると共に3種の新メガスチグマン配糖体salvionosides A, B, Cを単離し，その化学構造を明らかにした．
116.
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.
117.
Yoshio Takeda, Hongjie Zhang, Toshiya Masuda, Gisho Honda, Hideaki Otsuka, Ekrem Sezik, Erdem Yesilada and Handong Sun : Megastigmane glucosides from Stachys byzantiana, Phytochemistry, Vol.44, No.7, 1335-1337, 1997.
(Summary)
トルコ産シソ科植物Stachys byzantina地上部の配糖体成分を検索し，5種の既知化合物を同定すると共に，2種の新メガスチグマン配糖体byzantionosides A, Bを単離し，その化学構造を明らかにした．
118.
Yoshio Takeda, Yukako Futatsuishi, Takashi Matsumoto, Toshiya Masuda, Hiroshi Terada and Hideaki Otsuka : Longirabdolide E,F and G,6,7-seco-ent-kaurenoids from Rabdosia longituba, Phytochemistry, Vol.45, No.4, 785-789, 1997.
(Summary)
シソ科植物アキチョウジ地上部のジテルペン成分を検索し新ジテルペンlongirabdolides E, F, Fを単離し，その化学構造を明らかにした．
119.
Kyoko Hayashi, Toshimitsu Hayashi, Hideaki Otsuka and Yoshio Takeda : Antiviral activity of 5,6,7-trimethoxyflavone and its potentiation of antiherpes activity of acyclovir, The Journal of Antimicrobial Chemotherapy, No.39, 821-824, 1997.
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.
Majekodunmi O. Fatope, Oladimeji T. Audu, Yoshio Takeda, Lu Zeng, Guoen Shi, Hiroko Shimada and Jerry L. McLaughlin : Bioactive ent-kaurenoids from Annona senegalensis, Journal of Natural Products, Vol.59, No.3, 301-303, 1996.
Takashi Matsumoto, Yoshio Takeda, Kimiko Soh, Hisashi Goto and Sachihiko Imai : Synthesis of pygmaeosine E, a linear abietane diterpene from Pygmaeopremna hebacea (Roxb.) Moldenke, Chemical & Pharmaceutical Bulletin, Vol.44, No.7, 1318-1325, 1996.
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.
128.
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.
(Summary)
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．
129.
Yoshio Takeda, Youko Morimoto, Takashi Matsumoto, Eiji Hirata, Anki Takushi, Choei Ogimi and Hideaki Otsuka : Iridoid glucosides from the leaves and stems of Duranta erecta, Phytochemistry, Vol.38, No.4, 1431-1435, 1995.
Yoshio Takeda, Yukako Futatsuishi, Takashi Matsumoto, Hiroshi Terada and Hideaki Otsuka : Rabdoshikoccins A and B, 8,9-seco-ent-kaurenoids form Rabdosia shikokiana var.occidentalis, Phytochemistry, Vol.35, No.5, 1289-1291, 1994.
(Summary)
シソ科植物サンインヒキオコシ地上部から新8,9-seco-ent-kaurene型ジテルペン，rabdoshikoccins A, Bを単離し，その化学構造を明らかにした．
133.
Yoshio Takeda, Takashi Matsumoto and Hideaki Otsuka : Longirabdolides A and B, 6,7-seco-ent-kaurenoids from Rabdosia longituba, Phytochemistry, Vol.35, No.5, 1275-1278, 1994.
(Summary)
シソ科植物Rabdosia longituba地上部から新6,7-seco-ent-kaurenoid型ジテルペン，longirabdolides A, Bを単離しその化学構造を明らかにした．
134.
Ryousuke Touyama, Yoshio Takeda, Kenichiro Inoue, Ikuo Kawamura, Masahiko Yatsuzuka, Takeshi Ikumoto, Shingu Tetsuro, Yokoi Toshio and Hiroyuki Inouye : Studies on the blue pigments produced from genipin and methyl amine I. Structures of brrownish-red pigments, intermediate leading to the blue pigments, Chemical & Pharmaceutical Bulletin, Vol.42, No.3, 668-673, 1994.
Yoshio Takeda, Matsumoto Takashi, Hiromitsu Terao, Yukako Futatsuishi, Tetsuro Shingu, Toshihiro Nohara and Tetsuya Kajomoto : Orthosiphol D and E, minor diterpenes from Orthosiphon stamineus, Phytochemistry, Vol.33, No.2, 411-415, 1993.
Yoshio Takeda, Yukako Futatsuishi, Teruyoshi Ichihara, Takashi Matsumoto, Hiromitsu Terao, Hiroshi Terada and Hideaki Otsuka : Rabdokaurins C and D, two new diterpenes from Rabdosia longituba, Chemical & Pharmaceutical Bulletin, Vol.41, No.4, 685-687, 1993.
中国産Rabdosia loxothyrsa葉部のジテルペン成分を検索し，新ジテルペンrabdoloxin A, Bを単離し，その化学構造を明らかにした．
146.
Yoshio Takeda, Tetsuro Fujita, Han-Dong Sun, Yoshinori Minami, Masamitsu Ochi and C.C. Chen : Revision of the structures of isodonal, rabdolasional and related diterpenoids, Chemical & Pharmaceutical Bulletin, Vol.38, No.7, 1877-1880, 1990.
Yoshio Takeda, Teruyoshi Ichihara, Kazuo Yamasaki and Hideaki Otsuka : Structure elucidation of inflexarabdonins G and H:two new diterpenoids from Rabdosia inflexa, Planta Medica, Vol.56, No.3, 281-283, 1990.
Yoshio Takeda, Koichi Takeda, Tetsuro Fujita, Han-Dong Sun and Yoshinori Minami : Studies on the diterpenoid constituents of Rabdosia ternifolia: structure elucidation of new diterpenoids, rabdoternins A, B and C, Chemical & Pharmaceutical Bulletin, Vol.38, No.2, 439-442, 1990.
(Summary)
中国産Rabdosia ternifolia葉部のジテルペン成分を検索し3種の新ジテルペン，rabdoternin A, B, Cを単離し，その化学構造を明らかにした．
149.
Yoshio Takeda, Teruyoshi Ichihara and Hideaki Otsuka : Isolongirabdiol, a new diterpenoid from Rabdosia longituba, Journal of Natural Products, Vol.53, No.1, 138-142, 1990.
Yoshio Takeda, Teruyoshi Ichihara, Tetsuro Fujita and Akira Ueno : Diterpenoids from Rabdosia inflexa, Phytochemistry, Vol.28, No.9, 2423-2426, 1989.
(Summary)
シソ科ヤマハッカの微量jテルペン成分を検索し，4種の新ジテルペン，inflexarabdonins C, D, E, Fを単離し，その化学構造を明らかにした．
152.
Yoshio Takeda, Teruyoshi Ichihara, Tetsuro Fujita and Akira Ueno : Ent-kaurenoids from Rabdosia umbrosa, Phytochemistry, Vol.28, No.6, 1691-1694, 1989.
(Summary)
Rabdosia umbrosa 5 ent-kaurene
153.
Yoshio Takeda, Teruyoshi Ichihara, Tetsuro Fujita and Akira Ueno : Diterpenoid constituents of Rabdosia umbrosa (Maxim.) Hara: Isolation and structure elucidation of two new diterpenoids, umbrosianin and rabdoumbrosanin, Chemical & Pharmaceutical Bulletin, Vol.37, No.5, 1213-1215, 1989.
(Summary)
2 umbrosianin rabdoumbrosnin
154.
Yoshio Takeda, Teruyoshi Ichihara, Kazuo Yamasaki and Hideaki Otsuka : Inflexarabdonins A and B, diterpenoids from Rabdosia inflexa, Phytochemistry, Vol.28, No.3, 851-854, 1989.
(Summary)
広島市内で採集したRabdosia inflexaから新ジテルペン，inflexarabdonin A, Bを単離し，その化学構造をスペクトルデータおよび化学反応の結果より明らかにした．
Yoshio Takeda, Teruyoshi Ichihara and Hideaki Otsuka : Studies on the diterpenoids of Rabdosia longituba (Miq.) Hara: structure of a new bitter diterpenoid, rabdolongin A and the absolute stereochemistry of rabdolongin B (maeocrystalD), Chemical & Pharmaceutical Bulletin, Vol.36, No.6, 2079-2083, 1988.
Yoshio Takeda, Tetsuro Fujita and Tetsuro Shingu : Structure elucidation of longikaurins A and B, new biologically active diterpenoids, Journal of the Chemical Society, Perkin Transactions 1, No.2, 379-383, 1988.
Yoshio Takeda, Teruyoshi Ichihara, Yoshihisa Takaishi, Tetsuro fujita, Tetsuro Shingu and Genjiro Kusano : Structure elucidation of new diterpenoids isolated from Rabdosia umbrosa var. leucantha, Journal of Chemical Society Perkin Transaction 1, No.11, 2403-2409, 1987.
(Summary)
シソ科植物葉部のジテルペン成分を検索し4種の新ジテルペン，kamekaurin,kamebakaurinin,kamebaacetals A, Bを単離しその化学構造を明らかにした．
161.
Yoshio Takeda, Satomi Tsuchida and Tetsuro Fujita : Four new iridoid glucoside p-coumaroyl esters from ajuga decumbens, Phytochemistry, Vol.26, No.8, 2303-2306, 1987.
Yoshio Takeda, Tetsuro Fujita, Tetsuro Shingu and Choei Ogimi : Studies on the bacterial gall of Myrica rubra:isolation of a new [7.0]-metacyclphane from the gall and DL-phenylacetic acid from the culture of gall forming bacteria, Chemical & Pharmaceutical Bulletin, Vol.35, No.6, 2569-2573, 1987.
Yoshio Takeda, Koichi Takeda and Tetsuro Fujita : Structures of ememogin and trichorabdonin, minor diterpenoids from Rabdosia trichocarpa, Journal of the Chemical Society, Perkin Transactions 1, No.4, 689-694, 1986.
Han-Dong Sun, Zhow-Wen Lin, Yun-Long Xu, Yoshinori Minami, Teruyoshi Marunaka, Tsuneo Togo, Yoshio Takeda and Tetsuro Fujita : Structures of sculponeatin A, B and C, three new diterpenoids having unique acetal structures from Rabdosia sculponeata, Heterocycles, Vol.24, No.1, 1-4, 1986.
(Summary)
中国産シソ科植物葉部のジテルペン成分を検索し，非常にユニークなアセタール構造を有するsculponeatin A, B, Cを単離し，その化学構造を明らかにした．
165.
Tetsuro Fujita, Han-Dong Sun, Yoshio Takeda, Yoshinori Minami, Teruyoshi Marunaka, Zhon-Wen Lin and Yun-Long Xu : Structure of phyllostachysin A: novel antineoplastic diterpenoid from Rabdosia phyllostachys, Chemical Communications, No.23, 1738-1739, 1985.
Shinichi Uesato, Yoshio Takeda, Toshihiro Hashimoto, Kenichi Uobe and Hiroyuki Inouye : Studies on monoterpene glucosides and related natural products Part 51. Absolute structures of hydrangenosides A, B, C, D, E, F, and G, novel type secoiridoid glucosides from two Hydrangea plants, Helvetica Chimica Acta, Vol.67, No.8, 2111-2127, 1984.
Yoshio Takeda, Tetsuro Fujita and Akira Ueno : Structure of rabdolatifolin, a diterpenoid from Rabdosia umbrosa var. latifolia, Phytochemistry, Vol.22, No.11, 2531-2533, 1983.
Tetsuro Fujita, Yoshio Takeda, Tetsuro Shingu, Masaru Kido and Zenei Taira : Structures of shikodomedin (X-ray analysis) and shikokiamedin: new cytotoxic 8,9-seco-ent-kaurenoids from Rabdosia shikokiana var. intermedia, Chemical Communications, No.3, 162, 1982.
Yoshio Takeda, Tetsuro Fujita and C.C. Chen : Structures of lasiocarpanin, rabdolasional and carpalasionin: new diterpenoids from Rabdosia lasiocarpa, Chemistry Letters, No.6, 833-836, 1982.
Tetsuro Fujita, Yoshio Takeda and Tetsuro Shingu : Longikaurins C, D, E and F: New diterpenoids from Rabdosia longituba, Heterocycles, Vol.16, No.2, 227-230, 1981.
Kenichiro Inoue, Yoshio Takeda, Takao Tanahashi and Hiroyuki Inouye : Studies on monoterpene glucosides and related natural products.XLI. Chemical conversion of geniposide into 10-hydroxyloganin, Chemical & Pharmaceutical Bulletin, Vol.29, No.4, 970-980, 1981.
Tetsuro Fujita, Yoshio Takeda and Tetsuro Shingu : Bitter diterpenoids from Isodon shikokianus var. intermedius, Phytochemistry, Vol.18, No.2, 299-301, 1979.
(Summary)
シソ科植物タカクマヒキオコシの微量ジテルペン成分としてshikodokaurins A, Bを単離し，その化学構造を明らかにした．
177.
Kenichiro Inoue, Yoshio Takeda, Hiroshi Nishimura and Hiroyuki Inouye : Studies on monoterpene glucosides and related natural products.XXXIX. Biogenetic-type transformation of geniposide into plumieride, Chemical & Pharmaceutical Bulletin, Vol.27, No.12, 3115-3122, 1979.
Yoshio Takeda, Hiroshi Nishimura and Hiroyuki Inouye : Two new iridoid glucosides from Mussaenda parviflora and Mussaenda shikokiana, Phytochemistry, Vol.16, No.9, 1401-1404, 1977.
Yoshio Takeda and Hiroyuki Inouye : Studies on monoterpene glucosides and related natural products.XXX. The fate of the C-8 proton of 7-deoxyloganic acid in the biosynthesis of secoiridoid glucosides, Chemical & Pharmaceutical Bulletin, Vol.24, No.1, 79-84, 1976.
Yoshio Takeda, Hiroshi Nishimura and Hiroyuki Inouye : Studies on monoterpene glucosides and related natural products.XXXII. Iridoid glucosides of Tarenna kotoensis var. gyokushinka, Chemical & Pharmaceutical Bulletin, Vol.24, No.6, 1216-1218, 1976.
Yoshio Takeda, Hiroshi Nishimura and Hiroyuki Inouye : Two new iridoid glucosides from Ixora chinensis, Phytochemistry, Vol.14, No.12, 2647-2650, 1975.
Hiroyuki Inouye, Shinichi Ueda, Kenichiro Inoue and Yoshio Takeda : Studies on monoterpene glucosides and related natural products.XXIII. Biosynthesis of secoiridoid glucosides, gentiopicroside, morroniside, oleuropein and jasminin, Chemical & Pharmaceutical Bulletin, Vol.22, No.3, 676-686, 1974.
Hiroyuki Inouye, Yoshio Takeda and Hiroshi Nishimura : On the lignan glucosides of Symplcos lucida, Journal of the Pharmaceutical Society of Japan, Vol.93, No.1, 44-46, 1973.
Hiroyuki Inouye, Shinichi Ueda, Yasuhiko Aoki and Yoshio Takeda : Studies on monoterpene glucosides and related natural products.XVII. The intermediacy of 7-deoxyloganic acid and loganin in the biosynthesis of several iridoid glucosides, Chemical & Pharmaceutical Bulletin, Vol.20, No.6, 1287-1296, 1972.
Hiroyuki Inouye, Shinichi Ueda and Yoshio Takeda : Studies on monoterpene glucosides and related natural products. XVIII. Formation sequences of iridoid glucosides in highly oxidized levels, Chemical & Pharmaceutical Bulletin, Vol.20, No.6, 1305-1311, 1972.
Hiroyuki Inouye, shinichi Ueda and Yoshio Takeda : Studies on monoterpene glucosides and related natural products.XIII. Incorporation of [10-14C]-sweroside into gentiopicroside and the alkaloids in Vinca and Cinchona plants, Chemical & Pharmaceutical Bulletin, Vol.19, No.3, 587-594, 1971.
Hideaki Otsuka and Yoshio Takeda : Diference of constituents between Glochidion species and diversity of constituents in Rabdosia longituba, Foods & Food Ingredients Journal of Japan, Vol.212, No.5, 365-373, May 2007.
2.
Yoshio Takeda and Hideaki Otsuka : Recent Advances in the Chemistry of Diterpenoids from Rabdosia Species, Studies in Natural Products Chemistry, Vol.15 Strcture and Chemistry(Part C), 111-185, 1995.
Hiroyuki Inouye and Yoshio Takeda : Biosynthetic studies on secoiridoid glucosides, Advances in Natural Products Chemistry,eds. by S. Natori, N. Ikegawa and M.Suzuki, 261-274, 1981.
(Summary)
セコイリドイド配糖体の生合成について概略を述べるとともに，著者の実験例についても紹介した．
4.
Hiroyuki Inouye, Shinichi Ueda and Yoshio Takeda : Biosynthesis of Secoiridoid glucosides, Heterocycles, Vol.4, No.3, 527-565, 1976.
Hideaki Otsuka and Yoshio Takeda : Polar Constituents of Glochidion Acuminatum, The 6th Joint Seminar Recent Advances in Natural Medicine Research Proceedings, 136, Kingdom of Thailand, Dec. 2003.
Naonobu Tanaka, 石丸 陽子, Mamoru Okasaka, Yoshihisa Takaishi, Yoshio Takeda, 本多 義昭, 伊藤 三千穂 and Kuo-Hsiung Lee : Searching for Bioactive Constituents from Hypericum Genus (Clusiaceae), 47th Symposium on the Chemistry of Natural Products Tokushima 2005, Vol.P61, 413-418, Oct. 2005.
14.
趙 大鵬, 松浪 勝義, 大塚 英昭 and Yoshio Takeda : ダンギク(Caryopteris incana Miq.)の成分研究, The 52th Annual Meeting of the Japanese Society of Pharmacognosy, Vol.59, No.4, 34, Sep. 2005.
15.
松浪 勝義, 大塚 英昭 and Yoshio Takeda : オオバギの葉部の成分研究, 日本薬学会 第125年会, Vol.31-0744, Mar. 2005.
16.
劉 輝, 大塚 英昭 and Yoshio Takeda : マルヤマカンコノキの成分, 日本薬学会 第125年会, Vol.31-0745, Mar. 2005.
17.
Yoshio Takeda : On the Constituents of Glochidion Obovatum, 日本薬学会 第124回年会, Sep. 2004.
Restructure and structure-activity relationship of the osteoporotic improvement effect compounds derived from echinoderms. (Project/Area Number: 22590112 )
Mechanism of radio-sensitizing effect caused by angiogenesis inhibitor (Project/Area Number: 21591726 )
COMPARATIVE STUDY ON TRADITIONAL MEDICINES OF TURKIC PEOPLE (3) (Project/Area Number: 15406003 )
Antioxidant Mechanism Studies for Food Phenol Based on the Radical Reaction Products with Food Components (Project/Area Number: 12660116 )
COMPARATIVE STUDY ON TRADITIONAL MEDICINES OF TURKIC PEOPLE (2) (Project/Area Number: 12576027 )
Comparative Study on the Traditional Medicine of Turkic People (Project/Area Number: 09041182 )