Abstract
We observed that the unstable 13 2, 17 3-cyclopheophorbide a enol is one of the most abundant pigments in recent sediments (Black Sea, Mediterranean Sea, Peru margin) and here we report its isolation and structure determination (high-performance liquid chromatography, ultraviolet-visible spectrometry, mass spectrometry, and nuclear magnetic resonance). This enol has been considered as the precusor of sedimentary chlorins and porphyrins bearing either a seven + five- or a seven-membered ring system. Analysis of sediment trap samples collected from the Peru Upwelling area revealed relatively high concentrations of 13 2, 17 3-cyclopheophorbide a enol in trap samples containing high concentrations of metabolically derived carotenoid transformation products. The abundance of 13 2, 17 3-cyclopheophorbide a enol in sediment trap samples and recent sediments suggests that formation of an exocyclic seven-membered ring is a major diagenetic pathway for chlorophylls. Biologically mediated transformations of chlorophylls can therefore yield products not included in the classical Triebs degradation scheme for cyclic tetrapyrroles.
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