Isolation and Structure Elucidation of Gymnemic Acids, Antisweet Principles of Gymnema sylvestre

Hong Min Liu; Fumiyuki Kiuchi; Yoshisuke Tsuda

doi:10.1248/cpb.40.1366

Isolation and Structure Elucidation of Gymnemic Acids, Antisweet Principles of Gymnema sylvestre

Hong Min Liu, Fumiyuki Kiuchi, Yoshisuke Tsuda

Research output: Contribution to journal › Article › peer-review

104 Citations (Scopus)

Abstract

The structure of gymnemagenin (3/?,16/?,21/?,22a,23,28-hexahydroxy-olean-l 2-ene), the sapogenin of the antisweet principles of Gymnema sylvestre, was established by X-ray analysis of the 3/?,23;21/?,22a-di-0~isopropylidene derivative. On the basis of this result, the structure of deacylgymnemic acid was elucidated as the 3-0-/?-glucuronide from the carbon-13 nuclear magnetic resonance spectra. Five antisweet principles, gymnemic acid-IIl, -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-/?-D-ara£i7f0-2-hexulopyranosyl gymnemic acid-III and -IV, respectively.

Original language	English
Pages (from-to)	1366-1375
Number of pages	10
Journal	Chemical and Pharmaceutical Bulletin
Volume	40
Issue number	6
DOIs	https://doi.org/10.1248/cpb.40.1366
Publication status	Published - 1992
Externally published	Yes

Keywords

20-hexopyranosid-2-ulose
Gymnema sylvestre Asclepiadaceae antisweet activity gymnemic acid saponin gymnemic acid-VIII gymnemic acid-IX oxo-glycoside D-ara£z>

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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title = "Isolation and Structure Elucidation of Gymnemic Acids, Antisweet Principles of Gymnema sylvestre",

abstract = "The structure of gymnemagenin (3/?,16/?,21/?,22a,23,28-hexahydroxy-olean-l 2-ene), the sapogenin of the antisweet principles of Gymnema sylvestre, was established by X-ray analysis of the 3/?,23;21/?,22a-di-0~isopropylidene derivative. On the basis of this result, the structure of deacylgymnemic acid was elucidated as the 3-0-/?-glucuronide from the carbon-13 nuclear magnetic resonance spectra. Five antisweet principles, gymnemic acid-IIl, -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-/?-D-ara£i7f0-2-hexulopyranosyl gymnemic acid-III and -IV, respectively.",

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author = "Liu, {Hong Min} and Fumiyuki Kiuchi and Yoshisuke Tsuda",

year = "1992",

doi = "10.1248/cpb.40.1366",

language = "English",

volume = "40",

pages = "1366--1375",

journal = "Chemical and Pharmaceutical Bulletin",

issn = "0009-2363",

publisher = "Pharmaceutical Society of Japan",

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T1 - Isolation and Structure Elucidation of Gymnemic Acids, Antisweet Principles of Gymnema sylvestre

AU - Liu, Hong Min

AU - Kiuchi, Fumiyuki

AU - Tsuda, Yoshisuke

PY - 1992

Y1 - 1992

N2 - The structure of gymnemagenin (3/?,16/?,21/?,22a,23,28-hexahydroxy-olean-l 2-ene), the sapogenin of the antisweet principles of Gymnema sylvestre, was established by X-ray analysis of the 3/?,23;21/?,22a-di-0~isopropylidene derivative. On the basis of this result, the structure of deacylgymnemic acid was elucidated as the 3-0-/?-glucuronide from the carbon-13 nuclear magnetic resonance spectra. Five antisweet principles, gymnemic acid-IIl, -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-/?-D-ara£i7f0-2-hexulopyranosyl gymnemic acid-III and -IV, respectively.

AB - The structure of gymnemagenin (3/?,16/?,21/?,22a,23,28-hexahydroxy-olean-l 2-ene), the sapogenin of the antisweet principles of Gymnema sylvestre, was established by X-ray analysis of the 3/?,23;21/?,22a-di-0~isopropylidene derivative. On the basis of this result, the structure of deacylgymnemic acid was elucidated as the 3-0-/?-glucuronide from the carbon-13 nuclear magnetic resonance spectra. Five antisweet principles, gymnemic acid-IIl, -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-/?-D-ara£i7f0-2-hexulopyranosyl gymnemic acid-III and -IV, respectively.

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Isolation and Structure Elucidation of Gymnemic Acids, Antisweet Principles of Gymnema sylvestre

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