A Model Study of Fecapentaenes: Mutagens of Bacterial Origin with Alkylating Properties

Abstract

Fecapentaene-14 and -12 are directly acting mutagens that do not require metabolic activation. Their unusual structure suggests a possible mechanism of action. A carbocation that is formed by the addition of an electrophilic species (such as a proton) to the enol ether is most probably the reactive species. A series of model enol ethers with conjugated systems of various lengths was prepared, and a correlation between mutagenicity and increasing reactivity of derived carbocations was found. The glycerol moiety does not play a crucial role in the overall reactivity of the fecapentaenes.

Plasmalogens the neglected regulatory and scavenging lipid species

“…Biochemically they contain a pentaenyl group (Bruce et al, 1982;Gupta et al, 1983Gupta et al, , 1984Hirai et al, 1985) and are produced by anaerobic Bacteroides spp. (Knudsen, 1986;Lederman et al, 1980;Van Tassel et al, 1982) from precursors known as plasmalopentaenes.…”

Chemical transformations of bile salts by the intestinal microflora

“…Finally, other endogenous compounds such as ketosteroids and glycerol ethers linked to long-chain polyunsaturated alcohols (fecapentaenes) were also shown to act as cancer inducers or promoters (Gupta et al, 1984). …”

Epidemiology and Mechanisms Relating Diet to Risk of Colorectal Cancer

“…Fecapentaenes, compounds with a central pentaene structure and a chain length of 12 or 14C, are direct acting alkylating mutagens (Gupta et al 1984). They are known to be produced by Bacteroides spp., the commonest species in the human colon, probably from plasmalogen phospholipids (Van Tassel1 et al 1989) which are structural components of lipid bilayers and which have their own unique pathway of biosynthesis.…”