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Chemical and Pharmaceutical Bulletin
Vol. 40 (1992) No. 6 P 1366-1375

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http://doi.org/10.1248/cpb.40.1366


The structure of gymnemagenin (3β, 16β, 21β, 22α, 23, 28-hexahydroxy-olean-12-ene), the sapogenin of the antisweet principles of Gymnema sylvestre, was established by X-ray analysis of the 3β, 23;21β, 22α-di-O-isopropylidene derivative. On the basis of this result, the structure of deacylgymnemic acid was elucidated as the 3-O-β-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-β-D-arabino-2-hexulopyranosyl gymnemic acid-III and -IV, respectively.

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