Glycosidic Constituents of the Leaves of an Okinawan Leguminosae Plant, Derris trifoliate Lour

From the leaves of Derris trifoliata, collected in Okinawa, 15 glycosidic compounds were isolated and identified.


A new phenolic glucoside from an Uzbek medicinal plant, Origanum tyttanthum

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.


Sesquiterpene Lactone from the Roots of Ferula varia and Their Cytotoxic Activity,

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.


Tricalysioside P-U: Ent-kaurane glucosides and a labdane glucoside from leaves of Tricalysia dubia Ohwi

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.


Bridelioside, a new lignan glycoside from Bridelia glauca Bl. f. balansae (Tucht.) Hatushima


Chemical constituents of an Uzbek medicinal plant, Perovskia scrophularifolia


Tricalysiolide G and tricalysiols A and B:rearranged ent-kaurane-type and ent-kaurane-type diterpenoids from the leaves of Tricalysia dubia (Lindl.) Ohwi


Identification of Antioxidative Compounds from Stevia

ステビア中の抗酸化性物質の同定

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.

ステビアの抗酸化成分を同定するに当たり，ステビアをメタノール抽出し，その抽出物の溶媒分画のうち，特異的にDPPHラジカル消去活性の強かった酢酸エチル可溶画分から，3種の活性成分を単離・同定した．この単離物質は，すべて，脂質の酸化に対して十分な抗酸化性を有することが判明した．ステビアの抗酸化性はこれまでカリウム等の無機塩によるものとされてきたが2)，今回の有機フェノール成分もステビア抗酸化性に十分に寄与している可能性が考えられた．


5-O-glucosyldihydrolavones from the leaves Helicia cochinchinensis

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.


Bridelionosides A-F:Megastigmane glucosides from Bridelia glauca f. balansae

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.


Radical-scavenging activities of new megastigmane glucosides from Macaranga tanarius (L.)Muelll.-Arg.

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.


Trypanocidal constituents of Dracocephalum komarovi


Tricalysiolides A-F new rearranged ent-kaurane diterpenes from Tricalysia dubia


Tricalysiosides H-O:Ent-kaurane glucosides from the leaves of Tricalysia dubia

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.


Recovery of Antioxidant Activity from Carnosol Quinone: Antioxidants Obtained from a Water-Promoted Conversion of Carnosol Quinone

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.

Journal of Agricultural and Food Chemistry


Staphylionosides A-K: Megastigmane Glucosides from the Leaves of Staphylea bumalda DC.

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.


Lanceocrepidiasides A-F, glucosides of guaiane-type sesquiterpene from Crepidiastrum lanceolatum

沖縄で民間薬，食用として用いられているホソバワダン地上部より6種の新グアイアン型セスキテルペン配糖体6種を8種の既知化合物と共に単離し，その化学構造を明らかにした．


Indole alkaloids from Rheum maximowiczii

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.


Screening for Tyrosinase Inhibitors among Extracts of Seashore Plants and Identification of Potent Inhibitors from Garcinia subelliptica

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.

Bioscience, Biotechnology, and Biochemistry


Prenylated Benzophenones and Xanthones from Hypericum scabrum

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.


Terpenic and phenolic glycosides from leaves of Breynia officinalis HEMSL

沖縄産トウダイグサ科植物オオシマコバンノキ葉部の配糖体成分を検索した結果，4種の新テルペン配糖体，breyniaionosideA-Dと共に3種のフェノール性新配糖体を単離し，その化学構造を明らかにした．


Thermal recovery of antioxidant activity from carnosol quinone, the main antioxidation product of carnosol

Journal of the Science of Food and Agriculture


Folk medicine in Uzbekistan: I. Toshkent, Djizzax, and Samarqand provinces

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.


Glochidiolide, isoglochidiolide, acuminaminoside, and glochidacuminosides A-D from the leaves of Glochidion acuminatum MUELL.

沖縄産トウダイグサ科植物ウラジロカンコノキ葉部の成分研究を行い，新規のbutenolide二量体2種，含窒素C-8二量体acuminaminoside，C-8化合物の配糖体4種を単離し，その化学構造をX線結晶解析を含む手法により明らかにした．


Lasianthionosides A-C, megastigmane glucosides from leaves of Lasianthus fordii

沖縄産アカネ科植物タシロルリミノキ葉部の配糖体成分を検索し，4種の既知化合物と共に3種の新メガスチグマン配糖体lasianthionosides A，B，Cを単離し，その化学構造をX線結晶解析を含む手法により明らかにした．


C,O-diglycosylapigenin from the leaves of Rhamnella inaequilata

沖縄産ヤエヤマネコノチチ葉部の配糖体成分を検索し，2種の既知フラボンC- ジグりコシドと共にrhamnellaflavosides A,B,Cと命名したC，O- ジグリコシルフラボンを単離し，その化学構造をスペクトル解析および化学反応の結果より明らかにした．


A trypanocidal diterpene with novel skeleton from Dracocephalum komarovi


Sesquiterpenoids from Artemisia tenuisecta

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.


Cytotoxic Screening of Medicinal and Edible Plants in Okinawa, Japan, and Identification of the Main Toxic Constituent of Rhodea japonica (Omoto)

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).

Bioscience, Biotechnology, and Biochemistry


A Simple Detection Method of Powerful Antiradical Compounds in the Raw Extract of Plants and Its Application for the Identification of Antiraducal Plant Constituents

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.

Journal of Agricultural and Food Chemistry


Muscanone:a 3-O-(1",8",14"-trimenyl)naringenin from Commiphora

オマーン産Commiphora wightii枝部より抗カビ活性を有する新naringeninny誘導体，musucanoneを単離し，その化学構造を明らかにした．


GlochidionosidesA-D:megastigmane glucosides from leaves of Glochidion Zeylanicum (Gaertn.)A. Juss.

沖縄産トウダイグサ科植物葉部の配糖体を検索した結果単離することができたメガスチグマン配糖体glochidionionosides A-Dの化学構造を明らかにした．


Stereochemistry of megastigmane glucosides from Glochidion zeylanicum and Alangium premnifolium

沖縄産カキバカンコノキおよびシマウリノキから単離されたメガスチグマン配糖体のうち，その一部の絶対立体配置が未解明の計4種のメガスチグマン配糖体の絶対立体配置につきmodified Moscher法を利用することにより明らかにした．


New icetexane and 20 norabietane diterpenes with trypanocidal activity from Dracocephalum komarovi.

ウズベキスタン産薬用植物Dracocephalum komarovi全草から抗トリパノゾーマ活性を有する新ジテルペン計3種を単離し，その化学構造を明らかにした．


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.


Larvicidal activity of extract and triterpenoids from Lantana camara

クマツズラ科植物Lantana camaraのbrine schrimp lethality assayで活性を示す画分より3種のトリテルペンを単離すると共に2種のlarvaeに対する活性を検討した．


Polysulfide Derivatives from Ferula foetida

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.


A new megastigmane glucoside from Phlomis spinidens

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.

ウズベキスタン産しそ科植物Phlomis spinidensの微量成分を検索し，phlomisionosideと命名したメガスチグマン配糖体を単離し，その化学構造を明らかにした．


Cytotoxic Activity of Quinone Derivatives of Phenolic Diterpenes from Sage


An iridoid glucoside dimer and non-glycosidic iridoid from the leaves of Lasianthus wallichii

沖縄産アカネ科植物マルバルリミノキ葉部の配糖体成分を検索し5種の既知化合物と共に，新非配糖体イリドイドおよびイリドイド配糖体2量体を単離し，その化学構造を明らかにした．


An Unusual Sesquiterpene Derivative from Ferula Kuhistanica

Ferula Kuhistanicaより単離したセスキテルペン誘導体の構造決定と活性を明らかにした．


Turpinionosides A-E; megastigmane glucosides from leaves of Turpinia ternata

沖縄産ミツバウツギ科植物，ショウベンノキ葉部の配糖体成分を検索しturpinionosides A-Eと命名したメガスチグマン配糖体5種を単離し，その化学構造を明らかにした．


Structural Identification of New Curcumin Dimers and Their Contribution to the Antioxidant Mechanism

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.

Journal of Agricultural and Food Chemistry


Tricalysiosides A-G; Rearranged ent-kaurenoid glycosides from the leaves of Tricalysia dubia

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.

沖縄産アカネ科植物シロミミズ葉部の配糖体成分を検索した結果，新転移ーent-カウラノイド配糖体7種を単離し，X線結晶解析を含む手法を用いてその構造を明らかにした．


Coumarins and γ-pyrone derivatives from Prangos pabularia: antibacterial activity and inhibition of cytokine release


Benzoylphloroglucinol Derivatives from Hypericum scabrum

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).


Contribution of a combination of ponicidin and acyclovir/gancyclovir to the antitumor effifiency of the herpes simplex virus thymidine kinase gene therapy system

しそ科植物より単離されたジテルペン，ponicidinがherpes simplex virus thymidine kinase gene therapy 系の抗腫瘍活性にacyclovir/ganciclovirと併用した場合に抗腫瘍活性を増大させることをin vivoの実験により明らかにした．


Antioxidant-related activities of ethanol extracts from edible and medicinal plants cultivated in Okinawa, Japan

沖縄産食薬用植物エタノール抽出物の抗酸化関連活性


Flow Cytometric Estimation on Cytotoxic Activity of Leaf Extracts from Seashore Plants in Subtropical Japan: Isolation, Quantification and Cytotoxic Action of (-)-Deoxypodpphyllotoxin

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.


Monoacylglycerol from Punica granatum seed oil

健康に資する天然物探索の一環としてザクロ種子油の成分を検索し，主成分として1-O-trans,cis,trans-9,11,13-octadecatrienoyl glycerolを単離，同定した．


Recovery Mechanism of the Antioxidant Activity from Carnosic Acid Quinone, an Oxidized Sage and Rosemary Antioxidant

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.


A bis-sesquiterpene and sesquiterpenolides from Inula macrophylla

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.


Sesquiterpenoids from the fruits of Ferula kuhistanica and antibacterial activity of the constituents of F. kuhistanica

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).


Myrisinionosides A-E: megastigmane glycosides from leaves of Myrisine sequinii

沖縄産Myrisine sequinii葉部の配糖体成分を検索した結果，5種の新メガスチグマン配糖体を単離し，その化学構造を明らかにした．


Phlomisflavosides A and B, new flavonol diglycosides from Phlomis spinidens

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．


Chemical Constituents of Prangos tschimganica; Structure Elucidation and Absolute Configuration of Coumarin and Furanocoumarin Derivatives with Anti-HIV Activity

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.


Glochiflavanosides A-D:flavanol glucosides from the leaves of Glochidion zeylanicum (Gaertn.) A Juss.

沖縄産トウダイグサ科植物カキバカンコノキ葉部より4種のフラバノール配糖体，glochiflavanosidesA-Dを単離し，その化学構造を明らかにした．


Farnesyl Hydroxybenzoic Acid Derivatives from Ferula kuhistanica

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.


Isolation and Antioxidant Activity of the Galloyl Flavonol Glycosides from a Seashore Plant, Pemphis acidula

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.

Bioscience, Biotechnology, and Biochemistry


Antioxidant Mechanism of Carnosic Acid: Structural Identification of Two Oxidation Products

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.

Journal of Agricultural and Food Chemistry


A new neoclerodane diterpenoid from Scutellaria hematochlora

ウズベキスタン産シソ科植物Scutellaria hematochloraからneoclerodan型新ジテルペンを単離しその化学構造を明らかにした．


Chemical Studies on Antioxidant Mechanism of Curcumin: Analysis of Oxidative Coupling Products from Curcumin and Linoleate

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.


Sesquiterpenes and Monoterpenes from the Bark of Inula macrophylla

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.


Terpenoids and γ-pyrone derivatives from Prangos tschimganica

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.


Phenylbutanoids and stilbene derivatives of Rheum maximowiczii

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.


Traditional medicine in Turkey X. Folk medicine in Central Anatolia

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.

トルコ共和国中央Anatolia地方の伝統薬について現地調査し，その起源植物名，伝統的な用法などについて報告した．


Sesquiterpenoids from Ferula kuhistanica

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.


Labdane diterpenoids from Marrubium globosum ssp. globosum

トルコ産薬用植物Marrubium globosum ssp. globosumのジテルペン成分について検索し，labdane 骨格を有する新微量成分を単離しその化学構造を明らかにした．


A Novel Radical Terminated Compound Produced in the Antioxidation Process of Curcumin against Oxidation of a Fatty Acid Ester


Isolation of lignan glucoside and neolignan sulfate from the leaves of Glochidion zeylanicum (Gaertn) A. Juss.

沖縄産カキバカンコノキのリグナン関連物質を検索し，2種の新化合物を4種の既知化合物と共に単離氏，新化合物についてはその化学構造を明らかにした．


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

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.

Journal of Agricultural and Food Chemistry


A new mwgastigmane and a new tetraketide from leaves of Euscaphis japonica

沖縄産ミツバウツギ科植物ゴンズイ葉部より新メガスチグマンおよびテトラケチドを単離しその化学構造を明らかにした．


Sesquiterpene Phenylpropanoid and Sesquiterpene Chromone Derivatives from Ferula pallida

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.


Phlorigidosides A-C, iridoid glucosides from Phlomis rigida

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.

トルコ産Phlomis rigida地上部の配糖体成分を検索し，5種の既知物質とともに3種の新イリドイド配糖体を単離しその化学構造を明らかにした．


Megastigmane, benzyl and phenethyl alcohol glycosides, and 4,4`-dimethoxytruxinic acid catalpol diester from the leaves of Premna subscandens

沖縄産クマツズラ科植物Premna subscandens葉部より4種の新化合物を単離し，その化学構造を明らかにした．


Glochidionolactone A-F: butenolide glucosides from leaves of Glochidion zeylanicum

沖縄産トウダイグサ科植物カキバカンコノキ葉部から6種の新butenolide配糖体を単離し，その化学構造をX線結晶解析の手法も含め明らかにした．


Coumarins and bicoumarin from Ferula sumbul: anti-HIV activity and inhibition of cytokine release

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.


Prenylated Benzoic Acid Derivatives from Ferula kuhistanica

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.


Macrophyllidimers A and B, two novel sesquiterpene dimers from the bark of Inula macrophylla


Macrophyllols A and B, Two Unusual Novel Sesquiterpene and Monoterpene Dimers from the Bark of Inula macrophylla

[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.


Iridoid glycosides from Lonicera quinquelocularis

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.

インドのヒマラヤ地方に分布するスイカズラ科植物Loncera quinquelocularisの配糖体成分を検索し既知のloganin, swerosideの他に，新配糖体を単離し，その化学構造を明らかにした．


A new phenylpropanoid-glycerol conjugate from Helitiera littoralis Dryand

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.

沖縄産サキシマスホウノキ葉部の成分を検索し，7種の既知化合物と共に新phenylpropanoid-glycerol conjugateを単離し，その化学構造を明らかにした．


Potentiation of ganciclovir toxity in herpes simplex virus thymidine kinase/ganciclovir administration system by ponicidin

シソ科植物から単離されたジテルペン，ponicidinが抗ウイルス剤ACVおよびGCVの作用をherpes simplex virusのthimidine kinaseを活性化することにより相乗的に強めることをin vitroの実験結果より明らかにした．


Oleanene palmitate from Ximenia americana


C18 acetylenic fatty acids of Ximenia americana

Ximenia americana地下部の成分をbrine shrimp lethality testなどの生物検定法に従い分画し，活性物質として2種のC18アセチレン結合を含む脂肪酸を単離しその化学構造を明らかにした．

Journal of Agricultural and Food Chemistry


Quality evaluation of plant dye Henna with glycosides

植物染料hennaの配糖体と品質について

植物染料Henna(Lawsonia inermisの葉)の品質評価法として指標物質として従来用いられていたlawsone(この化合物は抽出過程で生じた人口産物と考えられる)に変え，2種の配糖体を指標物質とした評価法を確立すると共に，種々の市場品についてその品質を評価した．


New sesquiterpene glucosides from Crepidiastrum lanceolatum

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.

沖縄地方で民間薬，食用として用いられているホソバワダン地下部の配糖体成分を検索しcrepidialanceosides A, Bの2種の新セスキテルペン配糖体を単離し，その化学構造を明らかにした．


Sesquiterpene Coumarins and Related Derivatives from Ferula pallida

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.


Hydroquinone diglycoside acyl esters from leaves of Myrsine sequinii

沖縄産Myrsine seguinii 葉部の配糖体成分を検索し，5種の新フェノール性配糖体seguinosides G-Kを単離しその化学構造を明らかにした．


Nepetaracemosides A and B: iridoid glucosides from Nepeta racemosa


Secoiridoid glycosides from Gentiana olivierii

ウズベキスタン産薬用植物Gentiana olivieri全草の成分について検討を加え，7種の既知セコイリドイド配糖体を同定すると共に，3種の新苦味セコイリドイド配糖体を単離しその化学構造を明らかにした．


A collagen network foreffector from leaves of Premna subscandensmation

M細胞は長期間in vitroで培養するとコラーゲン繊維ネットワークを形成するが，それに影響を及ぼす天然物検索の過程でPremna subscandensより活性物質としてacteosideを同定した．


Euscapholide and its Glucoside from Leaves of Euscaphis japanica

沖縄産ミツバウツギ科植物ゴンズイ葉部から新テトラケチドおよびその配糖体を単離し，その化学構造を明らかにした．


Premnaodorosides D-G: Acyclic monoterpene diols iridoid glucoside diester from leaves of Premna subscandens

石垣島産Premna subscandens葉部より4しゅの新イリドイド配糖体premnaodorosides D-Gを単離し，その化学構造を明らかにした．


Phenylbutenoids from the Rhizomes of Alpinia flabellata


Evaluation of Antioxidant Activity of Environmental Plants: Activity of the Leaf Extracts from Seashore Plants

Journal of Agricultural and Food Chemistry


Traditional medicine in Turkey IX. Folk medicine in north west Anatolia

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.

トルコ共和国西北Anatolia地方の伝統薬について調査し，その起源植物，用法などについて報告した．


Chemical Studies on Antioxidant Mechanism of Curcuminoid: Analysis of Radical Reaction Products from Curcumin


Phlomisethanoside, a phenylethanoid glycoside from Phlomis grandiflora var. grandiflora

トルコ産シソ科植物Phlomis grandiflora var. grandiflora地上部の配糖体成分を検索し，新フェニルエタノイド配糖体，phlomisethanosideを単離しその化学構造を明らかにした．


Hydroquinone glycosides from leaves of Myrisine sequinii

沖縄産Myrisine sguinii葉部よりarbutin関連の新配糖体6種を単離しその化学構造を明らかにした．


(+)-Isolarisiresinol 3a-O-sulfate from the leaves of Myrsine sequinii


Iridoid glucosides with different acyl moieties from globurarinin and globularimin

石垣島産Premna subscandens 葉部より5種の新イリドイド配糖体を単離し，その化学構造を明らかにした．


Nuclear magnetic resonance and biosynthetic studies of neoantimycin and structure elucidation of isoneoantimycin, a minor metabolite related to neoantimycin

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.

Streptoverticillium orinociの産生する抗生物質neoantimycinの全H，CNMRシグナルを帰属し，その知見に基づき生合成時の立体化学につき検討を加えた．また，同菌が生産する微量成分，isoneoantimycinの化学構造を明らかにした．


Synthesis of (+-)-Cassumunins A and B, New Curcuminoid Antioxidants Having Protective Activity of the Living Cell against Oxidative Damage


An acyclic monoterpene glucosyl ester from Lantana lilacia

ブラジルで健康増進の目的で用いられているLantana lilacia地上部の成分につき検討を加え，verbascosideを同定すると共に，新モノテルペングルコシルエステルを単離し，その化学構造を明らかにした．


Sesquiterpene glycosides and seaquilignan glycosides from stems of Alangium premnifolium


Iridoid and eugenol glycosides from Nepeta cadmea

トルコ産シソ科植物Nepeta cadmea地上部より4種の新イリドイド配糖体及び1種の新eugenol配糖体を単離し，その化学構造を明らかにした．


A novel dimeric butenolide, glochidiolide from the leaves of Glochidion acuminatum

沖縄産トウダイグサ科植物ウラジロカンコノキ葉部より非常にユニークな化学構造を持つbutenolide二量体を単離し，その構造をX線結晶解析により明らかにした．


Glochidioboside, a glucoside of (7S,8R)-dihydrodehydroconiferyl alcohol from leaves of Glochidion obovatum

沖縄産トウダイグサ科植物カンコンキ葉部の成分につき検討を加え，5種の既知化合物を同定すると共に，新ネオリグナン配糖体glochidiobosideを単離し，その化学構造を明らかにした．


Euscapholide and its glucosides from leaves Euscaphis japonica

沖縄産ミツバウツギ科植物ゴンズイ葉部より新テトラケチドおよびその配糖体を単離し，その化学構造を明らかにした．


10-O-acylated iridoid glucosides from leaves of Premna subscandens

石垣島産Premna subscandens葉部から10種の新イリドイド配糖体を単離し，その構造がcatalpolおよびasystasioside Eの10-アシル誘導体であることを明らかにした．


A guaianolide and a germacranolide from Achillea santolina

エジプト北部産のキク科植物Ahillea santolinaのセスキテルペン成分について検討し既知化合物5種を同定すると共に2種の新セスキテルペンラクトンを単離し，その化学構造をX1線結晶解析を含む手法により明らかにした．


Premethanosides A and B, phenylethanoids from leaves of Premna subscabdebs

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．


Synthesis of Cassumunin A, a Potent Antiinnflamatory Antioxidant from a Medicinal Ginger, Zingiber cassumunar


Megastigmane glycosides from Salvia nemorosa

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．


Traditional medicine in Turkey. VIII. Folk medicine in east Anatolia ; Erzurum, Erzincan, Agri, Kars, Igdir Provinces


Megastigmane glucosides from Stachys byzantiana

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．


Longirabdolide E,F and G,6,7-seco-ent-kaurenoids from Rabdosia longituba

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．


Antiviral activity of 5,6,7-trimethoxyflavone and its potentiation of antiherpes activity of acyclovir

5,6,7-trimethoxyflavoneがHSV-1および人サイトメガウイルスおよびポリオウイルスに対して比較的強い阻害活性を示すことを明らかにするとともに，その阻害の機構に示唆を与えた．

The Journal of Antimicrobial Chemotherapy


Traditional medicine in Turkey VI. Folk medicine in West Anatolia: Afyon, Kütahya, Denizli, Muğla, Aydin provinces


トルコ産Nepeta nuda ssp albifloraからアグリコン部が通常のイリドイド配糖体のそれの鏡像体であるイリドイド配糖体nepetanudosides B, C, Dを単離し，その化学構造を明らかにした．


Nepetacilicioside, a new iridoid glucoside from Nepeta cilicia

トルコ産Nepeta cilicia地上部から既知のvelpetinの他に，新イリドイド配糖体nepetaciliciosideを単離し，その化学構造を明らかにした．


Bioactive ent-kaurenoids from Annona senegalensis

Annona senegalensis樹皮抽出物のcytotoxityを指標とした分画により4種の活性ent-kaurenoidを単離すると共に，そのがん細胞に対する細胞毒性を検討した．


Synthesis of pygmaeosine E, a linear abietane diterpene from Pygmaeopremna hebacea (Roxb.) Moldenke

Dehydroabietic acidより製したmethyl 12-methoxy-7-oxo-8,11,13-abietatrien-18-oateからlinear abietane型ジテルペン，pygmaeosine Eを合成した．


中国産Taxus yunnanensis地下部の成分を検索し，2種の新taxane型ジテルペンを単離し，その化学構造を明らかにした．


Longirabdolide D, a new 6,7-seco-ent-kaurenoid from Rabdosia longituba

広島県豊田郡で採集したシソ科植物アキチョウジ地上部から新ジテルペンlongirabdolide Dを単離し，その化学構造を明らかにした．


Marrubinones A and B, New Labdane Diterpenoids from Marrubium astracanicum(Labiatae)


Traditional medicine in Turkey. VII: Folk medicine in middle and west Black Sea regions

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．


Iridoid glucosides from the leaves and stems of Duranta erecta

沖縄産タイワンレンギョウ葉部および枝部より4種の新イリドイド配糖体duranterectosides A-Dを単離し，その化学構造を明らかにした．


Alangionosides G-M:glycosides of megastigmane derivatives from Alangium premnifolium

沖縄産シマウリノキ葉部から新メガスチグマン配糖体alangionosides G-Mを単離し，その化学構造を明らかにした．


Rabdoternin D-G,ent-7beta,20-epoxykaurens from Rabdosia ternifolia

中国産シソ科植物Rabdosia ternifoliaの微量成分を検討し，4種の新ジテルペンを単離し，その化学構造を明らかにした．


Rabdoshikoccins A and B, 8,9-seco-ent-kaurenoids form Rabdosia shikokiana var.occidentalis

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．


Longirabdolides A and B, 6,7-seco-ent-kaurenoids from Rabdosia longituba

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．


Studies on the blue pigments produced from genipin and methyl amine I. Structures of brrownish-red pigments, intermediate leading to the blue pigments

Genipinとメチルアミンと酸素存在下生成する青色色素の生成過程を検討するため，酸素非存在下で生成する赤色色素の構造について検討を加え，それらが2-methyl-4carbomethoxy-2-pyridine誘導体の単量体，二量体，三量体，四量体であることを明らかにした．


Longirabdolactone and longirabdacetal, 6,7-seco-ent-kaurenoids from Rabdosia longituba

広島市郊外で採集したしそ科植物，アキチョウジ地上部より新ジテルペン，longirabdolactoneおよびlongirabdacetalを単離し，その化学構造を明らかにした．


Orthosiphol D and E, minor diterpenes from Orthosiphon stamineus

沖縄県で栽培されたクミスクチンの微量成分を検索した結果，2種の新ピマラン型ジテルペン，orthosiphol D, Eを単離し，その化学構造を明らかにした．


Rabdokaurins C and D, two new diterpenes from Rabdosia longituba

岡山県で採集したRabdosia longituba地上部より新ジテルペン，rabdokaurins C, Dを単離し，その化学構造を明らかにした．


Inflexarabdonins I,J and K, ent-kaurenoids from Rabdosia inflexa

広島産ヤマハッカの微量ジテルペン成分を検索し，新ent-kaurene型ジテルペン，inflexarabdonins, I, J, Kを単離し，その化学構造を明らかにした．


Diterpenoid constituents of Rabdosia longituba

大分県日田郡で採集したアキチョウジ地上部のジテルペン成分を検索し，得られた新ジテルペンの化学構造を明らかにした．


Plygalae Radixとしてよく用いられる生薬であるPolygala tenuifoliaの根のキサントン成分を検索し，6種の新キサントンを単離し，その化学構造を明らかにした．


Diterpenoids having ent-kaurene and ent-spiro-seco-kaurene skeletons from Rabdosia longituba

広島県神石郡で採集したRabdosia longituba地上部の微量ジテルペンを検索し，新ジテルペンrabdokaurins A, Bを単離し，その化学構造を明らかにした．


The enantioselective metabolism of p-cymene in rabbit

p-Cymeneのウサギでの代謝の立体化学について検討した．即ち，その代謝産物の構造を明らかにすることにより，イソプロピル基のpro-S メチル基の酸化が優先的に起こる事を明らかにした．


Fragments of acylated 6-alpha-L-rhamnopyranosylcatalpol from leaves of Premna japonica

クマツズラ科植物ハマクサギ葉部の配糖体成分を検索し5種の新化合物を単離し，それらがモノアシルラムノピラノースの構造を持つことを明らかにした．


Iridoid diglycoside monoacyl esters from stems of Premna japonica

クマツヅラ科植物ハマクサギ枝部の配糖体成分を検索し，3種の新イリドイド配糖体を単離し，その化学構造を6-O-rhamnosylcatalpolのモノアシルたいであることを明らかにした．


Ent-kaurene diterpenoids from Rabdosia loxothyrsa

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．


Revision of the structures of isodonal, rabdolasional and related diterpenoids

ジテルペン，isodonal, rabdolasionalおよび関連化合物の構造について2次元NMRを用いて再検討し，従来提出去れていた化学構造式を訂正した．


Structure elucidation of inflexarabdonins G and H:two new diterpenoids from Rabdosia inflexa

シソ科植物ヤマハッカ葉部の微量ジテルペンを検索し，新ジテルペン，inflexarabdonin G, Hを単離し，その化学構造を明らかにした．


Studies on the diterpenoid constituents of Rabdosia ternifolia: structure elucidation of new diterpenoids, rabdoternins A, B and C

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．


Isolongirabdiol, a new diterpenoid from Rabdosia longituba

広島市安芸区で採集したRabdosia longituba地上部のジテルペン成分を検索し，新ジテルペンisolongirabdiolを単離し，その化学構造を明らかにした．


Monoterpene glucosides having a cross conjugated dienone system

バラか植物コデマリ葉部の配糖体成分を検索し，交差共役系を持つモノテルペングルコシド3種を単離し，その化学構造を明らかにした．


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．


Diterpenoid constituents of Rabdosia umbrosa (Maxim.) Hara: Isolation and structure elucidation of two new diterpenoids, umbrosianin and rabdoumbrosanin


Inflexarabdonins A and B, diterpenoids from Rabdosia inflexa

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．


Cytotoxic and antitumor activities of Rabdosia diterpenoids

従来の研究過程で分離したRabdosia ジテルペン24種についてHela細胞に対するcytotoxityを検討した．また，そのうち，15種については，Ehrlich ascites carcinoma cellに対するin vivoでのマウスの延命効果を検討し，その結果について報告した．


New phenolic glucosides from Lawsonia inermis

ミソハギ科植物Lawsonia inermis葉部の配糖体成分を検索し，新フェノール性配糖体，lawsoniasideおよびlaliosideを単離し，その化学構造を明らかにした．


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)

広島市近郊で採集した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rabdolongin Aの化学構造を明らかにした．また，同時に単離されたrabdolobgin B(=maeocrystal D)の絶対立体配置についても明らかにした．


A new phenolic glycoside from Phthiirospermum japonicum

ゴマノハグサ科植物シオガマギクの配糖体成分を検索し，4種の既知フェノール配糖体，3種の既知イリドイド配糖体を単離，同定すると共に，1新フェニルエタノイド配糖体，phtheirospermosideを単離し，その化学構造を明らかにした．


Structure elucidation of longikaurins A and B, new biologically active diterpenoids

徳島産アキチョウジ葉部から単離された主ジテルペンlongikaurin AおよびBの化学構造を明らかにした．また，oridoninからdihydrolongikaurin Aへの化学変換についても報告した．

Journal of the Chemical Society, Perkin Transactions 1


Structure elucidation of new diterpenoids isolated from Rabdosia umbrosa var. leucantha

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．

Journal of Chemical Society Perkin Transaction 1


Four new iridoid glucoside p-coumaroyl esters from ajuga decumbens

シソ科植物キランソウ全草の配糖体成分を検索し，4種の新イリドイド配糖体,decumbeside A-Dを単離し，その化学構造を明らかにした．


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

徳島県の県木であるヤマモモの細菌性gallの成分について検討し，正常植物からは見出されていない「7，0」-メタサイクロファンの5-deoxymyricanoneを単離し，その化学構造を明らかにした．


Structures of ememogin and trichorabdonin, minor diterpenoids from Rabdosia trichocarpa

シソ科植物クロバナヒキオコシ葉部の微量ジテルペン成分を検索しememoginおよびtrichorabdoninを単離し，その化学構造を明らかにした．また，本植物の主成分であるenmeinからtrichorabdonin への化学変換についても報告した．


Structures of sculponeatin A, B and C, three new diterpenoids having unique acetal structures from Rabdosia sculponeata

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．


Structure of phyllostachysin A: novel antineoplastic diterpenoid from Rabdosia phyllostachys

中国産Rabdosia phyllostachysのジテルペン成分を検索した結果，抗腫瘍活性を有するphyllostachysinを単離し，その化学構造が，特異な7,20-cyclo-ent-kaurenoid骨格を持つことを明らかにした．


Streptomyces antibioticus strain Tu 99の産生する抗生物質ketomycinがphenylalaninや2,5-dihydrophenylalaninを経由せず，prephenic acidおよびchorismic acidを経由して生合成される事を明らかにすると共に生成過程の立体化学についても報告した．


Fungal metabolites. II. Structure elucidation of minor metabolites, valinotricin, cyclonerodiol oxide, and epicyclonerodiol oxide, from Trichoderma polysporum


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

ユキノシタ科Hydrangea植物2種から特異な構造を有するセコイリドイド配糖体を単離し，その化学構造を明らかにした．


Structure of rabdolatifolin, a diterpenoid from Rabdosia umbrosa var. latifolia

シソ科植物コーシンヤマハッカ地上部のジテルペン成分を検索し，5種の既知化合物を同定すると共に，8,9-seco-ent-kaurene骨格を持つ新化合物rabdolatifolinを単離し，その化学構造を明らかにした．


Structures of shikodomedin (X-ray analysis) and shikokiamedin: new cytotoxic 8,9-seco-ent-kaurenoids from Rabdosia shikokiana var. intermedia

徳島産タカクマヒキオコシ地上部のジテルペン成分を検索し，8,9-seco-ent-kaurene骨格を持つshikodomedinおよびshikokiamedinを単離し，その化学構造をX線結晶解析を含む手法により決定した．


Structures of lasiocarpanin, rabdolasional and carpalasionin: new diterpenoids from Rabdosia lasiocarpa

シソ科植物タイワンヒキオコシ地上部のジテルペン成分を検索し，新ジテルペンlasiocarpanin, rabdolasional, carpalasioninの3種を単離し，その化学構造をあきらかにした．


Longikaurins C, D, E and F: New diterpenoids from Rabdosia longituba

徳島県産アキチョウジ葉部の微量ジテルペン成分を検索し，抗菌活性を示すlongikaurins C-Fを単離し，その化学構造を明らかにした．


Studies on monoterpene glucosides and related natural products.XLI. Chemical conversion of geniposide into 10-hydroxyloganin

イリドイド配糖体loganinnからセコイリドイド配糖体secologaninへの五員環開烈の際の中間体と考えられていた10-hydroxyloganinをクチナシ果実の主成分であるgeniposideから合成した．


シソ科植物カメバヒキオコシ葉部のジテルペン成分を検索し，ent-kaurene骨格を有する6種の新ジテルペンleukamenin A-Fを単離し，その化学構造を決定した．


Structures of effusanins, antibacterial diterpenoids from Rabdosia effusa

静岡県産セキヤノアキチョウジ地上部のジテルペン成分を検索し，抗菌活性を示すジテルペン5種，effusanins A-Eを単離し，その化学構造を明らかにした．


Bitter diterpenoids from Isodon shikokianus var. intermedius

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．


Studies on monoterpene glucosides and related natural products.XXXIX. Biogenetic-type transformation of geniposide into plumieride

イリドイド配糖体の中では比較的複雑な構造のplumierideをそのbiogenesisを考慮し，クチナシ果実の主成分であるgeniposideから8段階の反応で合成した．


Two new iridoid glucosides from Mussaenda parviflora and Mussaenda shikokiana

アカネ科植物コンロンカおよびヒロハノコンロンカから2種の新イリドイド配糖体，mussaenosideおよびshanzhiside methyl esterを単離し，その化学構造を明らかにした．


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

セコイリドイド配糖体が7-deoxyloganic acidからloganinを経て生合成される時，7-deoxyloganic acid のC-8プロトンは保持されることを標識化合物の投与実験の結果から明らかにした．


Studies on monoterpene glucosides and related natural products.XXXII. Iridoid glucosides of Tarenna kotoensis var. gyokushinka

アカネ科植物ギョクシンカの配糖体成分を検索し，既知のgeniposidic acidとixosideを同定すると共に．新イリドイド配糖体，tarennnosideを単離し，その化学構造を明らかにした．


Two new iridoid glucosides from Ixora chinensis

アカネ科植物サンタンカの配糖体成分を検索し，既知のgeniposidic acidと共に，新イリドイド配糖体，ixorosideおよびixosideを単離し，その化学構造を明らかにした．


Studies on monoterpene glucosides and related natural products.XXIII. Biosynthesis of secoiridoid glucosides, gentiopicroside, morroniside, oleuropein and jasminin

種々の標識化合物の植物への投与実験の結果，genntiopicroside型およびoleuropein型，両タイプのセコイリドイド配糖体とも中間にsecologaninを経由して生合成されることを明らかにした．


Two iridoid glucosides from Gardenia jasminoides fruits

アカネ科植物クチナシの果実の微量配糖体を検索し，2種の新イリドイド配糖体gardosideおよびscandoside methyl esterを単離し，その化学構造を明らかにした．また，geniposideからgardosideへの化学変換に成功した．


On the lignan glucosides of Symplcos lucida

クロキSymplocos lucida葉部から新リグナン配糖体2種を単離し，その化学構造を明らかにした．

Journal of the Pharmaceutical Society of Japan


Studies on monoterpene glucosides and related natural products.XVII. The intermediacy of 7-deoxyloganic acid and loganin in the biosynthesis of several iridoid glucosides

標識化合物の種々の植物への投与実験の結果，7-deoxyloganic acidが種々のイリドイド配糖体の生合成中間体であることを明らかにした．また，loganinがその次の中間体として介在していることも明らかにした．


Studies on monoterpene glucosides and related natural products. XVIII. Formation sequences of iridoid glucosides in highly oxidized levels

数種の高度に酸化されたイリドイド配糖体が生合成されるとき7-deoxyloganic acid,loganinからの生成過程を種々の標識イリドイド配糖体の植物への投与実験の結果より明らかにした．


Studies on monoterpene glucosides and related natural products.XIII. Incorporation of [10-14C]-sweroside into gentiopicroside and the alkaloids in Vinca and Cinchona plants

Swerosideの10位を特異的に14Cで標識した化合物を合成氏，その植物への投与実験の結果から，インドールアルカロイドの非トリプトファン部にセコイリドイド配糖体が取り込まれることを証明した．