Liu H M, Kiuchi F, Tsuda Y
Faculty of Pharmaceutical Sciences, Kanazawa University, Japan.
Chem Pharm Bull (Tokyo). 1992 Jun;40(6):1366-75. doi: 10.1248/cpb.40.1366.
The structure of gymnemagenin (3 beta,16 beta,21 beta,22 alpha,23,28-hexahydroxy-olean-12-ene), the sapogenin of the antisweet principles of Gymnema sylvestre, was established by X-ray analysis of the 3 beta,23;21 beta,22 alpha-di-O-isopropylidene derivative. On the basis of this result, the structure of deacylgymnemic acid was elucidated as the 3-O-beta-glucuronide from the carbon-13 nuclear magnetic resonance spectra. Five antisweet principles, gymnemic acid-III, -IV, -V, -VIII, and -IX, were isolated in pure states from the hot water extract of leaves of Gymnema sylvestre. Of these, three (GA-III, -IV, and -V) were known, while two (GA-VIII and -IX) were new compounds. The structures of GA-VIII and -IX were elucidated as 3'-O-beta-D-arabino-2-hexulopyranosyl gymnemic acid-III and -IV, respectively.
匙羹藤皂苷元(3β,16β,21β,22α,23,28 - 六羟基齐墩果 - 12 - 烯)是匙羹藤抗甜味成分的皂苷元,其结构通过对3β,23;21β,22α - 二 - O - 异亚丙基衍生物进行X射线分析得以确定。基于这一结果,通过碳 - 13核磁共振光谱阐明了去酰基匙羹藤酸的结构为3 - O - β - 葡萄糖醛酸苷。从匙羹藤叶的热水提取物中分离出了5种抗甜味成分,即匙羹藤酸 - III、 - IV、 - V、 - VIII和 - IX,并获得了它们的纯品。其中,3种(GA - III、 - IV和 - V)是已知的,而另外2种(GA - VIII和 - IX)是新化合物。GA - VIII和 - IX的结构分别被阐明为3'-O - β - D - 阿拉伯糖 - 2 - 己酮糖基匙羹藤酸 - III和 - IV。