Gorgosterol biosynthesis

Anderson, D. G., Gorgosterol biosynthesis localisation of squalene formation in the zooxanthellar component of various gorgonians, Comp. Biochem. Physiol., 81B, 423, 1985. 

Scheme 13. Biosynthesis of the gorgosterol side-chain in dinofiageilates...

The biosynthesis of gorgosterol (93) has been the subject of much discussion and speculation, yet it was not until very recently that its origin was elucidated [60]. This study was performed by feeding radiolabeled sterols to a cell-free extract of the heterotrophic dinoflagellate Crypthecodinium cohnii. As was predicted [55] in 1970, the gorgosterol side-chain (in 93a) is produced from dinosterol (94) as shown in Scheme 13. 

Other biogenetically distinct cyclopropane side chain substitution patterns are typified by the sponge sterols calysterol (25) isolated from Calyx nicaensis, and petrosterol (19) found in Petrosia. Unlike the biosynthesis of gorgosterol-type (17)... 

Complex mixtures of mostly A -sterols, with cholesterol usually dominant, are found in the Coelenterates (1). Some species are of interest b use they possess the unusual C30 sterol gorgosterol. At present there is very little evidence to support biosynthesis of sterols in Coelenterates. 

Figure11.2 Biosynthesis of dinosterol, peridinosterol, and gorgosterol Djerassi, 1981 Djerassi and Doss, 1990 Giner and Djerassi, 1991).

Giner, J.-L. and Djerassi, C. (1991) Biosynthetic studies of marine lipids. 33. Biosynthesis of dinosterol, peridinosterol and gorgosterol imusual pattern of bioalkylation in dinoflagellate sterols. /. Otg. Chem., 56,2357-2363. 

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