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The sesquiterpene fraction of the essential oil of Artemisia laciniata Willd.

✍ Scribed by Peter Weyerstahl; Helga Marschall; Martin Schröder; Hans-Christian Wahlburg; Vijay K. Kaul

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
204 KB
Volume
12
Category
Article
ISSN
0882-5734

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✦ Synopsis

The sesquiterpene fraction of the essential oil from Artemisia laciniata Willd. (Compositae) from the Kashmir region of India was analysed and found to contain mainly oxygenated derivatives. The main constituent, about 4% of the total oil, is silphiperfol-5-en-3-ol A (29). Besides many other minor compounds possessing this rare skeleton, the biogenetically related presilphiperfolan-9a-ol (17, ca. 2%) was isolated. Almost all the other compounds represent the davanones (21, 27, 32) and their oxygenated derivatives (23, 36, 37, 40). Most important are the bicyclic artedouglasia oxides (13, 15, 24, 30) and the laciniatafuranones (12, 14, 16, 19, 20). Five of the eight possible diastereoisomers of this novel compound were isolated and stereochemically assigned by extensive 1 H-NMR studies and molecular modelling considerations. Two compounds, the 3-hydroxyisodavonone ( 23) and its 1,2-dehydro derivative (37) show a unique keto enol moiety. Presilphiperfolan-9-ol (17, woody, sweet) and silphiperfol-5-en-3-ol A (29, woody, ambergris) contribute remarkably to the interesting odour of this Artemisia oil.

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