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The sesquiterpene fraction of the essential oil of Artemisia laciniata Willd.
Author(s) -
Weyerstahl Peter,
Marschall Helga,
Schröder Martin,
Wahlburg HansChristian,
Kaul Vijay K.
Publication year - 1997
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/(sici)1099-1026(199709/10)12:5<315::aid-ffj662>3.0.co;2-q
Subject(s) - sesquiterpene , chemistry , bicyclic molecule , moiety , diastereomer , stereochemistry , essential oil , fraction (chemistry) , monoterpene , diterpene , organic chemistry , enol , chromatography , catalysis
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‐9α‐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 2 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. © 1997 John Wiley & Sons, Ltd.