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Two New Triterpene and a New Nortriterpene Glycosides from Phlomis viscosa
Author(s) -
Çalış İhsan,
Kırmızıbekmez Hasan,
Taşdemir Deniz,
Rüedi Peter
Publication year - 2004
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200490059
Subject(s) - chemistry , triterpene , glycoside , stereochemistry , oleanane , epimer , hydroxymethyl , carboxylic acid , terpene , saponin , organic chemistry , medicine , alternative medicine , pathology
The isolation and structure elucidation of two new oleanane‐type triterpene glycosides, 29‐( β ‐ D ‐glucopyranosyloxy)‐2 α ,3 β ,23‐trihydroxyolean‐12‐en‐28‐oic acid (=(2 α ,3 β ,4 α ,29 α )‐29‐( β ‐ D ‐glucopyranosyloxy)‐2,3,23‐trihydroxyolean‐12‐en‐28‐oic acid; 1 ) and its C(20)‐epimer, 30‐( β ‐ D ‐glucopyranosyloxy)‐2 α ,3 β ,23‐trihydroxyolean‐12‐en‐28‐oic acid (=(2 α ,3 β ,4 α ,29 β )‐29‐ β ‐ D ‐glucopyranosyloxy)‐2,3,23‐trihydroxyolean‐12‐en‐28‐oic acid; 2 ), and a novel nortriterpene glycoside, (17 S )‐2 α ,18 β ,23‐trihydroxy‐3,19‐dioxo‐19(18→17)‐ abeo‐28‐norolean‐12‐en‐25‐oic acid β ‐ D ‐glucopyranosyl ester (=(1 R ,2 S ,4a S ,4b R ,6a R ,7 R ,9 R ,10a S ,10b S )‐3,4,4a,4b,5,6,6a,7,8,9,10,10a,10b,11‐tetradecahydro‐1‐hydroxy‐7‐(hydroxymethyl)‐3′,4′,4a,4b,7‐pentamethyl‐2′,8‐ dioxospiro[chrysene‐2(1 H ),1′‐cyclopentane]‐10a‐carboxylic acid β ‐ D ‐glucopyranosyl ester; 3 ) from Phlomis viscosa (Lamiaceae) are reported. The structures of the compounds were asigned by means of spectroscopic (IR, 1D‐ and 2D‐NMR, and LC‐ESI‐MS) and chemical (acetylation) methods.