Bisabolene epoxide

Scheme 8 Syntheses of cis-Z- and Jrans-Z-bisabolene epoxide pheromone components from Nezara viridula and other stink bug species, part 1 [67,71,76,77]...

Scheme 10 Conversion of ds-Z-bisabolene epoxide to trans-Z-bisabolene epoxide...

Extract of odors collected from sexually mature males of the green stink bug, Acrostemum hilare Ssy (Hemiptera Pentatomidae), showed one major sex-specific component, (45)- r-(Z )-bisabolene epoxide [(45)-cis-2 -BAE]. The crude extract was attractive to females, but when separated into four fractions, only the portion containing (45)-c -2 -BAE and the minor component AS)-trans-Z- AE was attractive to females. The fraction was as attractive as the crude extract suggesting that the former contained all the components. Neither the cis- nor the trans- BAE alone was attractive to females, but a 95 5 cis-.trans blend, mimicking the ratio naturally produced by males was attractive to females in Y-tube bioassays. " ... 

Ryu JH, Jeong YS, Sohn DH (1999) A new bisabolene epoxide from Tussilago farfara, and inhibition of nitric oxide synthesis in LPS-activated macrophages. J Nat Prod 62(10) 1437-1438 Saadali B, Boriky D, Blaghen M, Vanhaelen M, Talbi M (2001) Alkamides from Artemisia dracunculus. Phytochemistry 58(7) 1083-1086... 

New bisabolane sesquiterpenoids from a variety of plant sources include (95)— (102).59-64 f-y-Bisabolene-8,9-epoxide (103) has been isolated from the alga Laurencia nipponica.65 This compound is possibly the precursor of various halo-genated chamigranes which are abundant in Laurencia algae. 

Qccurance and Identification. An early report of cotton volatile composition by Minyard et al. (44) involved steam distillation of large quantities of leaves and flowers. Major compounds identified included the monoterpenes a-pinene, B-pinene, myrcene, trans-B-ocimene, and limonene ( 4). Several other monoterpene hydrocarbons were also present in low concentration. Since that report, many other terpenes have been identified in cotton essential oil steam distillates and solvent extracts. These compounds include cyclic hydrocarbons such as bisabolene, caryophyllene, copaene and humulene (45-47), the cyclic epoxide caryophyllene oxide (45), cyclic alcohols such as bisabolol, spathulenol, and the aromatic compound... 

Gyanchandani [85] has thus chromatographed caraway seed oil and dill oil under standard conditions and determined the position of the limonene epoxide (1,2) which had been formed by autoxidation of limonene. Nigam, Sahasrabudhe and Levi [185] have detected piperitone oxide in peppermint oils in a similar way. Attention has been drawn repeatedly to the bisabolene oxides I, II and III along with chamazulene in the assessment of camomile oils [78, 224, 305, 306]. 

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