Sesquiterpenes patchoulol

N.A. Sesquiterpenes patchoulol, bulnesene.99 Aphrodisiac, antidepressant, antiseptic. 

The related tricyclic sesquiterpene patchoulol (48a) is a good substrate for microorganisms and hy-droxylation at various sites can be accomplished, for example at C-S by Choanephora circinana in 74% yield (equation 14). Hydroxylation of the methyl group on C-4 can be accomplished by PenicUlium ru-brum FX-318 in 75% yield,and of the C-14 methyl group in (lf )-caryolan-l-ol (48b) by Aspergillus niger (MMP 521) in 26% yield. ... 

Croteau, R., S. L. Munck, C. C. Akoh, H. J. Fisk, and D. M. Satterwhite, Biosynthesis of the sesquiterpene patchoulol from famesyl pyrophosphate in leaf extracts of Pogostemon cablin (patchouli) Mechanistic considerations. Arch. Biochem. Biophys. 256, 56-68 (1987). 

The guaianes, like the eudesmanes, are derived from a further internal cychzation of germacrene A. The family includes matricin (81) and chamazulene (82), major components of the extract of German chamomile Matricaria chamomilla), which has anti-inflammatory properties (Castleman 2003). Related to the guaianes is the tricyclic sesquiterpene patchoulol (83), a perfumery raw material which is the major component... 

Patchouli alcohol. Patchouli oil comes from Pogostemonpatchouli and the main constituent is patchouli alcohol [5986-55-0] (105) or patchoulol. Another component of the essential oil is norpatchoulenol (106), a norsesquiterpene derivative as a minor (3—5%) constituent, important ia determining the overall odor of the essential oil (197). The price of patchouli oil ia 1995 was 20.90/kg from Indonesia (69). Alarge proportion of the oil (40—60%) is comprised of sesquiterpene hydrocarbons that do not have much odor value. World production of the oil was at about 750 t ia 1984. It is valuable ia perfumery bases because of its characteristic woody, herbaceous odor (198). 

One year later, Schalk [89] described a process for cloning sesquiterpene synthases from patchouli plants Pogostemon cablin) and the enzyme-catalysed terpenoid production. Various sesquiterpenes can be obtained by this method, for instance patchoulol and other germacrene-type sesquiterpenes. 

In this instance, the sesquiterpene olefin cyclase activity could not be separated from the patchoulol synthase activity and showed similar pH and metal ion requirements, suggesting that the olefmic products are derived by diversion of the various carbocation intermediates (Cane, 1990). 

Munck, S.L. and Croteau, R. (1990) Purification and characterization of the sesquiterpene cyclase patchoulol synthase from Pogostemon cablin. Arch. Biochem. Biophys. 282, 58-64. 

The sesquiterpene (C15) molecules include structures like hydrocarbons () -bisabolene, j3-caryophylene), alcohols (famesol, carotol, patchoulol), ketones (nootkatone) and aldehydes (anisaldehyde, valerenal). 

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