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Two New Triterpene and a New Nortriterpene Glycosides from Phlomis viscosa

✍ Scribed by İhsan Çalış; Hasan Kırmızıbekmez; Deniz Taşdemir; Peter Rüedi


Publisher
John Wiley and Sons
Year
2004
Tongue
German
Weight
116 KB
Volume
87
Category
Article
ISSN
0018-019X

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✦ Synopsis


Abstract

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.


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