[Glyyunnanprosapogenin and glyyunnansapogenin from the roots of Glycyrrhiza yunnanensis]

Abstract

Two new triterpenoidal sapogenins of oleanane type, namely glyyunnanprosapogenin D (V) and glyyunnansapogenin F (IX) were isolated from the roots of Glycyrrhiza yunnanensis Cheng f. et L. K. Tai, family Leguminosae, collected from Yunnan Province, China. V was obtained as hexaacetate and dimethyl ester form (Vc), mp 168-170 degrees C, C56H78O22, which gave an aglycone macedonic acid (V') and two molecules of glucuronic acid after hydrolysis with hydrochloric acid. The spectral analysis of 13CNMR and 1HNMR showed that Vc had two glycoside residues attached to the aglycone, and therefore the structure of V was established as oleana-11, 13(18)-dien-29-oic acid, 3 beta, 21 alpha-di-(O-beta-D-glucuronic acid) pyranoside. IX was obtained as its diacetate and monomethyl ester form (IXc), mp 188-190 degrees C, C35H50O7. The IR, 1HNMR and UV spectra showed that the IXc had a skeleton of oleanane type triterpenoid with heteroannular diene. IXb, diacetate of IX, unpurified, was converted to IXf with chromium trioxide in glacial acetic acid. IXf, mp 160-164 degrees C, C30H46O8, was proved to be olean-12-en-11-oxo-3 beta,24-diacetoxy-18 beta-hydroxy-30-oic acid, 30 in equilibrium 18 beta lactone with another carbonyl group at C-15,16,21 or 22 by the analysis of 13CNMR, 1HNMR and MS spectra.(ABSTRACT TRUNCATED AT 250 WORDS)