Sterols sponges

A recent and surprising finding in sponge sterol biosynthesis is the observation that certain 24-alkyl sterols can be transformed to cholesterol [46,48, 50]. This is particularly unusual, as this pathway operates in organisms which are also... 

Djerassi, C. and Silva, C. J., Biosynthetic studies of marine lipids. 41. Sponge sterols origin and biosynthesis, Acc. Chem. Res., 24, 371, 1991. 

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)... 

Australian sample collected in the Darwin Reservoir. The above compounds exhibited hypermethylation of one terminal isoprene unit, previously only exhibited by the methylated side chain of some sponge sterols 40 ... 

Stoilov, I.L., J.E. Thompson, J-H. Cho, and C. Djerassi Biosynthetic studies of marine lipids. Stereochemical aspects and hydrogen migrations in the biosynthesis of the triply alkylated side chain of the sponge sterol strongylosterol. J. Am. Chem. Soc. 108, 8235 (1986). 

Bohlin, L., H.P. Gehrken, P.J. Scheuer, and C. Djerassi Minor and Trace Sterols in Marine Invertebrates XVI. 3 -Hydroxymethyl-A- or-5a-gorgostane, a Novel Sponge Sterol. Steroids 35, 295 (1980). 

Li, X., and C. Djerassi Minor and Trace Sterols in Marine Invertebrates. 40. Structure and Synthesis of Axinyssasterol, 25-Methylfucosterol and 24-Ethyl-24-methyl-cholesterol - Novel Sponge Sterols with Highly Branched Side Chains. Tetrahedron Lett. 24, 665 (1983). 

In sponge sterols the configuration 2A(S) is privileged compared with the configuration 2A R)-, consequently, dihydrobrassicasterol 2%) and clionasterol (C29) are much more frequent than campesteroi and sitosterol. 

Cho, J.-H. and Djerassi, C. (1987a) Minor and trace sterols in marine invertebrates. 58. Stereostmcture and synthesis of new sponge sterols jaspisterol and isojaspisterol. ]. Org. Chem., 52, 4517—4521. 

Doss, G.A., Proudfoot, J.R., Silva, C.J., and Djerassi, C. (1990) Biosynthetic studies of marine lipids. 24. Experimental demonstration of an unprecedented cyclopropane-cydopropene rearrangement in the biosynthesis of the sponge sterol petrosterol. f Am. Chem. Soc., 112, 305-310. 

Jacob, M.R., Hossain, C.F., Mohammed, K.A., SmiDie, T.J., Clark, A. M., Walker, L.A., and Nagle, D.G. (2003) Reversal of fluconazole resistance in multidrug efflux-resistant fimgi by the Dysidea arenaria sponge sterol 9a,lla,-epoxycholest-7-ene-3p,5a,6a,19-tetrol-6-acetate. J. Nat. Prod., 66,1618-1622. 

John, V, Stoilov, l.L, Djerassi, C., Karuso, P., Poiner, A., and Scheuer, P.J. (1989) Biosynthetic studies of marine lipids. 20. Sequence of double-bond introduction in the sponge sterol 24p-methylcholesta-5,7,22,25-tetraen-3p-ol. J. Org. Chem, 54,1642-1647. 

Kerr, R.G., Kerr, S.L, and Djerassi, C. (1991b) Biosynthetic studies of marine lipids. 26. Elucidation of the biosynthesis of mutasterol, a sponge sterol with a quaternary carbon in its side chain. J. Org. Chem., 56,63-66. 

Silva, C.J. and Djerassi, C. (1991) Sterols in marine invertebrates. Part 64. Isolation, stereochemistry, and biosynthesis of sormosterol, a novel cyclopropane-containing sponge sterol. Collect. Czech. Chem. Commun., 56, 1093-1105. 

Stoilov, I.L., Thompson, J.E., and Djerassi. C. (1986d) Biosynthetic studies of marine hpids. 10. Double side chain extension in the triply alkylated sponge sterol xestosterol. Tetrahedron Lett., 27, 4821-4824. 

Li, X. and Djerassi, C. (1983) Minor trace sterols in marine invertebrates 40. Structure and synthesis of axinyssasterol, 25-methylfucosterol and 24-ethyl-24methylcholesterol novel sponge sterols with highly branched side chains. Tetrahedron Lett, 24, 665-668. 

Proudfoot, (.R Li, X and Djerassi, C. (1985) Minor and trace sterols from marine invertebrates. 50. Stereostructure and synthesis of nicasterol, a novel cyclopropane[Pg.1333]

Cho, J.-H., Thompson, J.E., Stoilov, I.L, and DjerassL C. (1988) Biosynthetic studies of marine lipids, 14. 24(28)-dehydroaplysterol and other sponge sterols from Jaspis stdlijera. J. Org. Chern., S3, 3466-3469. 

Since then, progress on sponge sterol research has been reported by Bergmann who reviewed the subject up to about 1960 (77). An earlier review on marine invertebrate sterols was written by the same author in 1949 16). 

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