- 著者
- 池田 浩人 森脇 英恵 松原 友規 湯川 美穂 岩瀬 由紀子 湯川 栄二 安藝 初美
- 出版者
- 公益社団法人 日本薬学会
- 雑誌
- YAKUGAKU ZASSHI (ISSN:00316903)
- 巻号頁・発行日
- vol.132, no.1, pp.145-153, 2012-01-01 (Released:2012-01-01)
- 参考文献数
- 8
- 被引用文献数
- 4 4
The influence of the presence of a galloyl group in catechin on complexation with risperidone (RISP) was examined using (−)-epigallocatechin gallate (EGCg) and (−)-epigallocatechin (EGC), which are present in green tea as tea catechins. By quantitative analysis using HPLC, it was found that EGCg formed an insoluble complex with RISP for concentration dependence, whereas EGC did not. The large contribution of the galloyl group of catechin to form an insoluble complex with RISP was recognized in this study. In a molecular modeling study, it was found that the EGCg-R complex (EGCg with RISP) formed three hydrogen bonds between the hydroxyl groups of EGCg and the two N atoms and an O atom of RISP. The hydrogen bond between the hydroxyl group of the galloyl ring in EGCg and the N atom of the piperidine ring in RISP stabilized EGCg-R more energetically. The EGC-R complex (EGC with RISP) also formed three hydrogen bonds, but the N atom of the piperidine ring in RISP did not participate in hydrogen bond formation. According to the calculation using the COSMO-RS method, the water solubility of the EGCg-R complex was 1/26 that of the EGC-R complex. Therefore, the EGCg-R complex was difficult to dissolve in water. In the 1H-NMR spectra of RISP in DMSO-d6, although chemical shifts of protons near the N atom on the piperidine ring moved downfield on the addition of EGCg, no change in chemical shifts of these protons was observed on the addition of EGC. Therefore, based on these results, the galloyl group of EGCg contributes to the formation of an insoluble complex between tea catechin and RISP, and this insoluble complex is stabilized by the hydrogen bond between the hydroxyl group of the galloyl ring in EGCg and the N atom of the piperidine ring in RISP.
- 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
- 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.