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Potamopholide, a New Sesquiterpene Lactone From Vernonia potamophila
Author(s) -
Kilonda Amuri,
Mihigo Shetonde,
Lohohola Osomba,
Tshibey Tshibangu Sha,
Compernolle Frans,
Toppet Suzanne,
Hoornaert Georges J.
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200301)2003:1<123::aid-ejoc123>3.0.co;2-b
Subject(s) - chemistry , sesquiterpene , sesquiterpene lactone , lactone , stereochemistry , organic chemistry
A new sesquiterpene lactone, named potamopholide, was isolated along with the known triterpene lupeol from the leaves of Vernonia potamophila . The stereochemical structure of the new compound, (3 R *,4 S *,5 E ,8 S *,10 S *)‐3,8‐epoxy‐3,4,13‐trihydroxy‐1‐oxogermacra‐5,7(11)‐dien‐6,12‐olide, was elucidated by mass spectrometric (CIMS, EIMS, HREIMS) and NMR spectroscopic (HMQC, HMBC, NOESY) analyses and by comparison with closely related compounds. The analysis was confirmed by MM+ geometry optimisation of the conformational structure. This 3,8‐O‐bridged 10‐membered ring hemiacetal seems to be related structurally to known 1,4‐O‐bridged compounds. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)