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Foetidissimosides C–F, Novel Glycosides from the Roots of Cucurbita foetidissima

✍ Scribed by Ghezala Gaidi; Tomofumi Miyamoto; Holger Lerche; Marie-Aleth Lacaille-Dubois


Book ID
102257274
Publisher
John Wiley and Sons
Year
2004
Tongue
German
Weight
107 KB
Volume
87
Category
Article
ISSN
0018-019X

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✦ Synopsis


Abstract

Two novel echinocystic acid (=(3__β__,16__α__)‐3,16‐dihydroxyolean‐12‐en‐28‐oic acid) glycosides, foetidissimosides C (1), and D (2), along with new cucurbitane glycosides, i.e., foetidissimosides E/F (3/4) as an 1 : 1 mixture of the (24__R__)/(24__S__) epimers, were obtained from the roots of Cucurbita foetidissima. Their structures were elucidated by means of a combination of homo‐ and heteronuclear 2D‐NMR techniques (COSY, TOCSY, NOESY, ROESY, HSQC, and HMBC), and by FAB‐MS. The new compounds were characterized as (3__β__,16__α__)‐28‐{[Oβ‐D‐glucopyranosyl‐(1→3)‐Oβ‐D‐xylopyranosyl‐(1→4)‐O‐6‐deoxy‐α‐L‐mannopyranosyl‐(1→2)‐α‐L‐arabinopyranosyl]oxy}‐16‐hydroxy‐28‐oxoolean ‐12‐en‐3‐yl β‐D‐glucopyranosiduronic acid (1), (3__β,16__α)‐16‐hydroxy‐28‐oxo‐28‐{{Oβ‐D‐xylopyranosyl‐(1→3)‐O‐[β‐D‐xylopyranosyl‐(1→4)]‐O‐6‐deoxy‐α‐L‐mannopyranosyl‐(1→2)‐α‐L‐arabinopyranosyl}oxy}olean‐12‐en‐3‐yl β‐D‐glucopyranosiduronic acid (2), and (3__β,9__β,10__α__,11__α__,24__R__)‐ and (3__β__,9__β__,10__α__,11__α__,24__S__)‐25‐(β‐D‐glucopyranosyloxy)‐9‐methyl‐19‐norlanost‐5‐en‐3‐yl 2‐Oβ‐D‐glucopyranosyl‐β‐D‐glucopyranoside (3 and 4, resp.).


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