Bisabolene oxide

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]. 

Resistant hirsutum race stocks Texas No. 254 and 810 also are deficient of bisabolene and B-bisabolol stocks 810, 1055, and 1123 have greatly increased caryophyllene oxide contents and stock 953 has greatly reduced concentrations of caryophyl 1 ene, caryophyl 1 ene oxide, and humulene (Table II). It is tempting to attribute the known increased resistance to insects in the Texas race stocks to the changes in volatile profiles, but this hypothesis remains to be proven. 

Terpenes in Asiatic and wild cottons. Volatile terpene profiles also were measured in two collections of the African wild cotton, . anomalum. and in four collections of the Asiatic cotton, arboreum. Both species lacked or had very low levels ofY-bisabolene and s-bisabolol (Table III). The Asiatic cottons also contained large percentages (7.5-33.0%) of caryophyl 1 ene oxide. We recently began to study the volatile terpenes in New World wild species. These preliminary studies indicate that species that lack hemigossypoione also are devoid of all volatile terpenes. We have no explanation for this interesting relationship. 

The main volatile components isolated from bacuri shells using various isolation methods, such as steam distillation and supercritical CO2 extractions were (Z)-linalool oxide, ( )-linalool oxide, 2-pentanone, 2-nonanone, ds-hexenyl acetate, methyl dodecacanoate, and several hydrocarbons, including bisabolene [46]. 

Although bisabolenes are quite common plant constituents, they are relatively rare as fungal metabolites. Cheimonophylion A (5.14) is a highly oxidized bisabolene that was isolated from a Basidiomycete, Cheimonophyllum candi-dissimium, and which was toxic towards nematodes. 

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... 

Comforth and his colleagues have investigated the stereochemistry of isomerization of isopentenyl to dimethylallyl pyrophosphate in isoprenoid biosynthesis. They find that the prototropic change involved is stereochemically different from the superficially analogous association of C5 units. Bisabolene appears to be excluded as an intermediate in the biosynthesis of helicobasidin and trichothecin by recent labelling studies (see also Vol. 1, p. 232, ref. 81) and a 1,4-hydride shift in the initially formed intermediate is indicated. The loss of the C-14 methyl group in cholesterol biosynthesis differs from loss of the C-4 methyl groups. The 32-carbon atom is released at the aldehyde oxidation level as formic acid. 

Beeswax, white Beeswax, yellow Benzoic, acid Benzyl tiglate y-Bisabolene Brominated vegetable oil 3-Butylidenephthalide Butyloxepanone 3-Butylphthalide Calcium lactate Caramel Castor (Ricinus communis) oil Citronellyl isovalerate Citronellyloxy acetaldehyde p-Cresyl isovalerate p-Cresyl octanoate Crotonic acid p-Cyclocitral p-Damascenone 9-Decenal trans-4-Decenal Diacetyl tartaric acid esters of mono- and diglycerides Diethyl malate Difurfuryl disulfide Dihydroeugenol Dihydro-a-ionone Dihydrojasmone Diisobutyl ketone Diisopropyl disulfide 3,4-Dimethylcyclopentane-1,2-dione Dimethyl dicarbonate 2,5 Dimethyl-3-furanthiol p-a-Dimethylstyrene Diphenyl oxide Ethyl acetate... 

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... 

In the course of the investigation of the antioxidative activity of EOs obtained from three different citrus species (Rutaceae), p-bisabolene was also determined for its antioxidative property. The LDL oxidation was measured spectrophotometrically at 234 nm by the formation of TEARS. The resnlts were expressed as nmol malonic dialdehyde/mg of protein. In the test system, p-bisabolene inhibited only TEARS formation from the AAPH-induced oxidation of LDL (Takahashi et al., 2003). 

The oxidized bisabolene derivative a-bisabolol with antiphlogistic properties is a main active compound in German chamomile (Matricaria recutita). Depending on the origin of the plants and the chemotype or variety, varying proportions of the oxides (bisabolol oxide A, bisabolol oxide B, or bisabolone oxide A) may be present in the respective oils [30]. a-Bisabolol can also be found in larger... 

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