Caryo-phyllene

If these assumptions be correct, there must be at least four natural sesquiterpenes of the caryophyllene character, namely, those represented by formulae (1) and (3), and the terp-caryophyllene and im-caryo-phyllene of Semmler. The most characteristic derivatives of the caryophyllenes are the following —... 

Nine compounds from branches with leaves and green fruit from apple consistently elicited an antennal response in codling female moths (Cydia po-monella, Lepidoptera), including methyl salicylate, ( )-/3-farnesene, /3-caryo-phyllene, 4,8-dimethyl-f,3( )-7-nonatriene, (3Z)-hexenol, (Z, )-a-farnesene, ( , )-a-farnesene, linalool and germacrene D [378]. 

GC-MS. The major compounds were found to be trans-linalool oxide and a-terpineol, whereas the dry black pepper oil contained a- and (3-pinenes, d-limonene and (3-caryo-phyllene as major components. When fresh pepper oil was isolated by distillation and analysed by GC and GC-MS, the compounds were found to be of a different nature to that of fresh pepper aromatic compounds (Menon, 2000). 

The number of sesquiterpenoids which can be formally derived from a caryo-phyllene-type precursor has risen quite dramatically in the last few years and includes the following structural types -... 

Phytochemistry The plant contains tanshinones (Sairafianpour et al. 2001). Water-distiUed essential oils from leaves collected in Arslonbob (Kyrgyzystan) contained cineole, pinene, epi-13-manool, bomyl acetate, camphene, camphor, caryo-phyllene, caryophyUene oxide, humulene, caryophylladienol, bomeol, and other compounds (Basher et al. 1997). 

Mehta, G., D. N. Dhar, and S. C. Suri Addition of Chlorosulphonyl Isocyanate to Some Polycyclic Sesquiterpenes, Longifolene, Isolongifolene, a-Cedrene, Caryo-phyllene and Thujopsene. Indian. J. Chem. 16B, 87 (1978). 

Caryophyllene, a compound found in oil of cloves, has the molecular formula C15H24 and has no triple bonds. Reaction of caryo-phyllene with an excess of hydrogen in the presence of a platinum catalyst produces a compound with the formula Ci5H28- How many... 

Devi, J.R., 1979. Microbiological transformation of terpenes Part XXVI. Microbial transformation of caryo-phyllene. Ind. J. Biochem. Biophys., 16 76-79. 

Lourens et al. (2004) evaluated the in vitro biological activity and chemical composition of the EOs of four indigenous South African Helichrysum species (Asteraceae), such as Helichrysum dasyanthum, Helichrysum felinum (strawberry everlasting), Helichrysum excisum, and. Helichrysum petiolare (licorice plant). An interesting anti-inflammatory effect could be observed in the lipooxy-genase-5 assay at doses between 25 and 32 pg/mL. Analysis of the chemical composition showed that the EOs comprise mainly monoterpenes such as a-pinene, 1,8-cineole, andp-cymene, only the oil of Helichrysum felinum was dominated by sesquiterpenes in low concentrations with P-caryo-phyllene as main compound on top. 

In the area of natural product synthesis, the isomeric sesquiterpenes, caryo-phyllene, and isocaryophyllene have been studied with respect to monohydro-boration with dicyclohexylborane and the hydroboration of a butadiene telomer, 3-acetoxy-octa-l, 7-diene, is the first step in a study regarding the synthesis of d7-a-lipoic acid. The reaction of organoboranes with 2,5-dihy-droxy-l,4-benzoquinone with subsequent application to the synthesis of rapanone has been studied. ... 

C. verum leaf oil contains high concentrations of eugenol (Ceylon type 80-88% Seychelles type 87-96%) it also contains many of the major constituents present in cinnamon bark oil (e.g., benzyl benzoate (6%), cinnamaldehyde, cinnamyl acetate, eugenol acetate, benzaldehyde, linalool, a-ter-pinene, and others), as well as other minor compounds, including a-humulene, 3-caryo-phyllene, a-ylangene, methyl cinnamate, and cinnamyl acetate (masada ravindran). °... 

Clove bud oil contains 60-90% eugenol, 2-27% eugenol acetate, and 5-12% P-caryo-phyllene, with minor constituents such as methyl salicylate, methyl eugenol, benzalde-hyde, methyl amyl ketone, a-ylangene, and chavicol also present (arctander masada). ... 

The seeds contain two potent antiulcer principles, namely, I -acetoxychavicol acetate and I -acetoxyeugenol acetate. Caryo-phyllene oxide, caryophyllenol I, caryophyl-lenol II, pentadecane, 7-heptadecane, and fatty acid methyl esters have also been isolated. The seeds contain diterpenes-I and -II (15a-and ISP-isomers), which have been patented in Japan as antitumor agents. It also exerted anti-inflammatory activity in both acute and chronic inflammation. The ethanolic extract of the herb showed significant antiulcer activity in rats, which has been attributed to the antisecretory and cytoprotective activities of the plant. 

A soln. of K-ferf-butoxide in ferf-butanol added to a soln. of a crude mixture of stereoisomeric 1,10-decalindiol monotosylates in ferf-butanol, and kept 45 min. at 35° frans-5-cyclodecenone. Y 82%. P. S. Wharton, G. A. Hiegel, and R. V. Goombs, J. Org. Ghem. 28, 3217 (1963) with mesylates instead of tosylates cf. H. H. Westen, Helv. 47, 575 (1964) with NaH in dimethyl sulfoxide, caryo-phyllene ring skeleton, cf. E. J. Gorey, R. B. Mitra, and H. Uda, Am. Soc. 86, 485 (1964). 

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