ISSN:
1573-1561
Keywords:
Dipterocarpus kerrii
;
sesquiterpenes
;
chemical synthesis
;
dienol
;
tropical biology
;
termiticide
;
Neotermes
;
α-gurjunene
;
γ-gurjunene
;
γ-gurjunenol
;
bioassay
;
stereochemistry
Source:
Springer Online Journal Archives 1860-2000
Topics:
Biology
,
Chemistry and Pharmacology
Notes:
Abstract Originally isolated fromDipterocarpus kerrii, the two previously uncharacterized sesquiterpenes,1 and20, were synthesized from α-gurjunene. A novel process involvingm-chloroperoxybenzoic acid oxidation ofα-gurjunene produced20 in one step. Spectroscopic studies determined that the diene moiety in20 is nonconjugated and also found the C-4 tertiary alcohol center to have theα-configuration, while the other stereocenters have configurations matching the corresponding centers inα-gurjunene. Bioassays with termites demonstrated that20 was more toxic than1, resulting in a 50% mortality in seven days when offered toNeotermes ?dalbergiae on filter papers. The chemicals appear to result from biotransformation ofα-gurjunene. In view of its similarity to the known sesquiterpeneγ-gurjunene, we suggest that20 be referred to asγ-gurjunenol.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00982134
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