Abstract
Fecapentaene-12 and fecapentaene-14 are genotoxic polyunsaturated ether-lipids produced by the colonic microflora in humans and pigs. Although the fecapentaenes have been extensively characterized, little is known about the nature of the precursors from which they are produced. We purified one form of these precursors from feces of an individual who excreted high levels of fecapentaene-12 and its precursors. Purification was carried out by a series of extractions and precipitation in organic solvents followed by silica and amine high performance liquid chromatography. The purified precursor had identical UV spectral characteristics as the fecapentaenes indicating that it contained the same ether-linked pentaenyl functional group. However, it was not mutagenic. The precursor was amphiphilic in nature, behaving like a synthetic “model” ether-phospholipid on silica and C18 thin layer chromatography. When incorporated into phosphatidylcholine micelles it could be hydrolyzedin vitro by a combination of lipase and phospholipase C to fecapentaene-12. Our findings indicate that the general structure of this precursor is that of a phospholipid, specifically a plasmalogen—the exact structures of which remain to be determined.
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Abbreviations
- BHT:
-
butylated hydroxytoluene
- MTBE:
-
methyl tert-butyl
- PBS:
-
phosphate-buffered saline
- BHI:
-
brain-heart infusion broth
- PRAS:
-
prereduced and anaerobically sterilized
- RCM:
-
Radial Compression Module
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Van Tassell, R.L., Piccariello, T., Kingston, D.G.I. et al. The precursors of fecapentaenes: Purification and properties of a novel plasmalogen. Lipids 24, 454–459 (1989). https://doi.org/10.1007/BF02535156
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DOI: https://doi.org/10.1007/BF02535156