Sesquiterpenes biogenesis

Hendrickson, J. B. Stereochemical Implications in Sesquiterpene Biogenesis. Tetrahedron 7, 82 (1959). 

Parker W, Roberts J S, Ramage R 1967 Sesquiterpene biogenesis. Quart Rev 21 331-363... 

The second component, pleraplysillin-1 (37), is a new type of sesquiterpene with a carbon skeleton so far unique [the classical review of sesquiterpene biogenesis by Parker et al. (757) and the comprehensive review of sesquiterpenes chemistry by Bryant 33) may be consulted. 

Figure 3. Biogenesis of predominant sesquiterpene and heliocide skeleta.

The flavour of distillates from apple and pear is characterised by typical aroma compounds from these fruits formed by enzymatic degradation of fatty acids to C6-fragments like hexanol, trans-2-hexenol, as well as ethyl esters and acetates of hexanoic acid. In distillates of pears, especially of the variety Bartlett pear, the characteristic pear flavour is mainly dominated by the ethyl and methyl esters of frans-2-czs-4-decadienoic acid and trans-2-trans-A-decadienoic acid [27-29], The biogenesis of these monounsaturated, diunsaturated, and triunsaturated esters may be explained by -oxidation of unsaturated linoleic and linolenic acid in the fruits. The sesquiterpene compound a-farnesene, which is formed during postharvest ripening and storage of Bartlett pears [28], shows that quality and intensity of distilled pear spirits is mainly influenced by the quality and degree of ripeness of the fruits. 

Harrison, B. and Crews, P. 1996. The structure and probable biogenesis of Helianane, a heterocyclic sesquiterpene, from the Indo-Pacific sponge Haliclona fascigera. J. Org. Chem. 62, 2646-2648... 

Fischer NH, Olivier EJ, Fischer HD (1979) The Biogenesis and Chemistry of Sesquiterpene Lactones. Prog Chem Org Nat Prod 38 270, 272... 

Cyclization humulene-4,S epoxide. Treatment ol this epoxide (1) with BF, etherate results in cyclization to equal amounts of the two isomeric alcohols 2 and 3, related to the sesquiterpene africanol 4, of marine origiia. Such a reaction could be involved in biogenesis of 4. ... 

Sutherland, M.D. and Park, R.J. (1967) Sesquiterpenes and their biogenesis in My-oporum desertii A. Cunn, in Terpenoids in Plants (ed. J. Pridham). Academic Press, London, pp. 147-57. 

Sesquiterpenes, as already reported in the previous sections, are the most widespread Lactarius metabolites however, a few species possess a particular metabolism which leads to secondary metabolites of other classes. Moreover, interesting new compounds with a different biogenesis have been isolated also from species producing large quantities of sesquiterpenes. 

In a study of the hydrocarbons from Reunion vetiver oil, a compound of the structure (ii) has been isolated, referred to as prezizaene. Zizaene (iii) can be detected in the acid-catalysed isomerisation of prezizaene, both of which are finally isomerised to three new hydrocarbons. The biogenesis of the zizaane-type sesquiterpenes is considered to involve cyclisation of (+)-v-curcumene (i) as shown. Personal communication from Professor... 

The biogenesis of those sesquiterpenes with a gem-dimethyl cyclopropane ring has been considered in terms of a precursor such as (384). This compound, bi-cyclogermacrene, has now been isolated from the peel oil of Citrus junos, together with germacrene-B and Bicycloelemene (385), previously isolated, is an... 

Over the last two decades discoveries in the field of marine natural products chemistry have yielded a remarkable array of novel secondary metabolites. These have included structure classes arising from a variety of biosynthetic pathways, some of which are unique to the marine environment. One class of marine metabolite that has received a considerable amount of attention, both through the abundance of structural variants and the biological properties ascribed to specific examples, is that involving the mixed biogenesis of a sesquiterpene unit with a quinol or a quinone. This review sets out to present a comprehensive survey of the known examples of this structure class, 1 to 108 (1-52). 

C 2H 02, Mr 194.27. Besides anastrephin, S. is an important component in the pheromone systems of tropical fruit- flies of the genus Anastrepha. The biogenesis of S., which is possibly a precursor of anastrephin, presumably involves the sesquiterpene alcohol famesol. ... 

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