Epoxy allylic carbocations as conceptual intermediates in the biogenesis of diverse marine oxylipins
- 1 December 1996
- Vol. 31 (12) , 1215-1231
- https://doi.org/10.1007/bf02587906
Abstract
Marine organisms, especially marine algae, are extremely rich in a diversity of novel oxylipin structures. Many of these oxylipins contain functionalities and rings of a type and location unknown in mammalian systems. In this perspective reviewing marine oxylipins, a proposal is formulated for the central intermediacy of an epoxy allylic carbocation in the biogenesis of these diverse structures. This proposal is strengthened by the relatively large number of examples which are consistent with this type of mechanistic transformation.Keywords
This publication has 67 references indexed in Scilit:
- Absolute Stereochemistry of Neohalicholactone from the Brown Alga Laminaria sinclairiiJournal of Natural Products, 1994
- Structure and stereochemistry of constanolactones A-G, lactonized cyclopropyl oxylipins from the red marine alga Constantinea simplexThe Journal of Organic Chemistry, 1994
- Structure and biosynthesis of marine algal oxylipinsBiochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, 1994
- Ascidiatrienolide A is a 10-membered lactoneJournal of the American Chemical Society, 1993
- Recent investigations into the lipoxygenase pathway of plantsBiochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, 1991
- Hepoxilin A3 (HxA3) is formed by the rat aorta and is metabolized into HxA3-C, a glutathione conjugateBiochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, 1991
- Mechanism of biosynthesis of 11R‐ and 12R‐hydroxyeicosatetraenoic acids by eggs of the sea urchin Strongylocentrotus purpuratusFEBS Letters, 1989
- Mechanism of corn hydroperoxide isomerase: detection of 12,13(S)-oxido-9(Z),11-octadecadienoic acidBiochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, 1987
- A new marine epoxy prostanoid with an antiproliferative activity from the stolonifer Clavularia viridis Quoy and Gaimard.CHEMICAL & PHARMACEUTICAL BULLETIN, 1987
- Antileukemic effect of coral-prostanoids clavulones from the stolonifer Clavularia viridis on human myeloid leukemia (HL-60) cellsBiochemical and Biophysical Research Communications, 1985