TY - JOUR
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.
KW - 20-hexopyranosid-2-ulose
KW - Gymnema sylvestre Asclepiadaceae antisweet activity gymnemic acid saponin gymnemic acid-VIII gymnemic acid-IX oxo-glycoside D-ara£z>
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U2 - 10.1248/cpb.40.1366
DO - 10.1248/cpb.40.1366
M3 - Article
C2 - 1327559
AN - SCOPUS:0026693047
VL - 40
SP - 1366
EP - 1375
JO - Chemical and Pharmaceutical Bulletin
JF - Chemical and Pharmaceutical Bulletin
SN - 0009-2363
IS - 6
ER -