- 著者
- 藤岡 稔大 岩元 雅代 岩瀬 由紀子 八山 しづ子 岡部 光 三橋 國英 山内 辰郎
- 出版者
- 天然有機化合物討論会実行委員会
- 雑誌
- 天然有機化合物討論会講演要旨集
- 巻号頁・発行日
- vol.30, pp.165-172, 1988
Dammarane-type triterpene glycosides, named actinostemmoside A, B, C, D, G and H, baccharane-type triterpene glycosides, actinostemmoside E and F, and oleanane-type triterpene glycosides, lobatoside A, B, C, D, E, F, G and H were isolated from the herb of Actinostemma lobatum MAXIM. (Cucurbitaceae). Their structures were elucidated on the basis of the spectral and chemical evidences as shown in the text. The structure of actinostemmoside F was elucidated mainly on the basis of two dimensional-incredible natural abundance double quantum transfer experiment (2D-INADEQUATE) spectrum. Among dammarane-type actinostemmosides, D is the glycoside of the first naturally occurring dammarane having the (20R)-configuration, and actinostemmosides E and F are the second baccharane-type triterpene glycosides isolated from the natural source. Lobatoside B, C, D, E, F and G are cyclic bisdesmosides similar to tubeimoside I isolated from the tuber of Bolbostemma paniculatum (MAXIM.) FRANQUET. (Cucurbitaceae), and this is the second instance of the isolation of cyclic bisdesmoside from the plant kingdom.
1 0 0 0 Studies on Cerbera. I. Cardiac Glycosides in the Seeds, Bark, and Leaves of Cerbera manghas L.
- 著者
- 阿部 フミ子 山内 辰郎
- 出版者
- 公益社団法人日本薬学会
- 雑誌
- Chemical & pharmaceutical bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.25, no.10, pp.2744-2748, 1977-10-25
Cardenolides in the seeds, bark, and leaves of Cerbera manghas L. were investigated. From the seeds, tanghinigenin glycosides were isolated along with known digitoxigenin glycosides, cerberin, neriifolin, thevetin B, and 2'-O-acetyl thevetin B. From the barks of root and stem, gentiobiosyl thevetoside, glucosyl thevetoside, and thevetoside of tanghinigenin and 17βH-tanghinigenin were obtained. The cardenolides in the air-dried leaves were found to vary with seasons. 17βH-neriifolin is major and preferable to neriifolin in July, while 17βH-deacetyltanghinin and deacetyltanghinin present in the leaves of Feb.
- 著者
- 阿部 フミ子 長尾 常敦 岡部 光 山内 辰郎 丸林 信洋 上田 幾彦
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.38, no.8, pp.2127-2129, 1990-08-25 (Released:2008-03-31)
- 参考文献数
- 5
- 被引用文献数
- 7 10
Parsonsianine, a 14-membered macrocyclic pyrrolizidine alkaloid, composed of retronecine, (2S, 3R)-2, 3-dihydroxy-2-ethylbutanoic acid and (2R, 3S)-2, 3-dihydroxy-2-isopropylbutanedioic acid, was isolated from the leaves of Parsonsia laevigata and the structure was determined by means of nuclear magnetic resonance and X-ray analysis.
- 著者
- 藤岡 稔大 岩元 雅代 岩瀬 由紀子 八山 しづ子 岡部 光 三橋 國英 山内 辰郎
- 出版者
- 天然有機化合物討論会実行委員会
- 雑誌
- 天然有機化合物討論会講演要旨集
- 巻号頁・発行日
- vol.30, pp.165-172, 1988
Dammarane-type triterpene glycosides, named actinostemmoside A, B, C, D, G and H, baccharane-type triterpene glycosides, actinostemmoside E and F, and oleanane-type triterpene glycosides, lobatoside A, B, C, D, E, F, G and H were isolated from the herb of Actinostemma lobatum MAXIM. (Cucurbitaceae). Their structures were elucidated on the basis of the spectral and chemical evidences as shown in the text. The structure of actinostemmoside F was elucidated mainly on the basis of two dimensional-incredible natural abundance double quantum transfer experiment (2D-INADEQUATE) spectrum. Among dammarane-type actinostemmosides, D is the glycoside of the first naturally occurring dammarane having the (20R)-configuration, and actinostemmosides E and F are the second baccharane-type triterpene glycosides isolated from the natural source. Lobatoside B, C, D, E, F and G are cyclic bisdesmosides similar to tubeimoside I isolated from the tuber of Bolbostemma paniculatum (MAXIM.) FRANQUET. (Cucurbitaceae), and this is the second instance of the isolation of cyclic bisdesmoside from the plant kingdom.
- 著者
- 岡部 光 宮原 由美 山内 辰郎
- 出版者
- 天然有機化合物討論会
- 雑誌
- 天然有機化合物討論会講演要旨集
- 巻号頁・発行日
- no.24, pp.95-102, 1981-09-10
An extensive survey for the triterpenoid constituents of Momordica charantia L. has been carried out in this laboratory, and so far, five glycosides (momordicosides A-E) of cucurbit-5-ene derivatives were isolated from the seeds, and their structures were determined. They are unique cucurbitacins being highly oxygenated only in the side chain and having no oxygen function at C_<11>. This study concerns the structure elucidation of two bitter glycosides, momordicosides K and L, and four non-bitter glycosides, momordicosides F_1, F_2, G and I isolated from the fruits. The structure of F_1 was proposed as 3-O-β-D-glucopyranoside of 5,19-epoxy-25-methoxy-5β-cucurbita-6,23-dien-3β-ol on the basis of PMR, CMR and CD spectral data and chemical conversion into a cucurbit-5-ene derivative. G is the corresponding β-D-allopyranoside. F_2 and I are the C_<25>-OH derivatives corresponding to G and F_1, respectively. K and L were determined as 7-O-β-D-glucopyranosides of 19-oxo-25-methoxy-cucurbita-5,23-diene-3β, 7β-diol and its C_<25>-OH derivative, respectively, on the basis of spectral data and chemical correlation with F_1-aglycone. F_1, F_2, G and I are the first cucurbitacins having 5β-cucurbitane nucleus found in nature, and K and L are noted as the new cucurbitacins having C_9-aldehyde and 7-O-β-D-glucopyranosyl groups. Among momordicosides, G and F_2 are the first triterpenoid glycosides having D-allose as a component sugar.
キョウチクトウ(Nerium indicum Mill.)葉には強心配糖体が高濃度に含有されており、葉を食草とするキョウチクトウスズメガ(Daphnis nerii L,以下D.nerii)の幼虫は強心配糖体を摂取し蓄積する可能性があるにもかかわらず、体色は明らかに保護色を呈している。幼虫が強心配糖体をいかに処理しているかを知るために、葉、幼虫、および幼虫の糞(以下frass)について強心配糖体の比較検討を行った。葉、幼虫、frassの抽出エキスのHPLCによる比較を行い、さらに各々のエキスについて通常のカラムクロマトを行って含有強心配糖体の単離、同定を試みた。葉においては主配糖体であるoleandrin gentiobiosideをはじめ、odoroside A,adynerin,D^<16>-adynerinなどがgentiobiose基を結合したtriosideとして得られたが、monosideとしても比較的少量のoleandrin,adynerin,odoroside A,D^<16>-adynerinなどが得られた。葉におけるoleandrinとadynerinの比は明らかにoleandrinが主配糖体であることが確認された。これに対し、幼虫およびfrassでは配糖体はすべてgentiobiose基が加水分解を受けてmonosideに移行している。またoleandrinは16位アセチル基も鹸化されてdeacetyloleandrinに変化していることが、oleandrinの減少、deacetyloleandrinの増加から明らかになった。この結果、幼虫およびfrassエキスでは、主配糖体は非活性のadynerin,次いでdeacetyloleandrinでありoleandrinは少なく、とくに幼虫のエキスではHPLCにおいても非常に低いピークが観察されるのみであった。したがって、虫体内の強心配糖体は質的にも毒性の弱い構成と考えられ、幼虫にとって保護色は必要と推定された。Frassから得られたadynerinの収量は異常に高い値を示し、幼虫におけるadynerinは、キョウチクトウ葉の成分中もっとも高い濃度で虫体から検出されたursolic acidとともに、その虫体における意義についてさらに検討する必要がある。