Epoxy allylic carbocations as conceptual intermediates in the biogenesis of diverse marine oxylipins

Lipids

Volumn 31, Issue 12, 1996, Pages 1215-1231

  Gerwick, William H ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; EPOXIDE; LIPOXYGENASE; POLYUNSATURATED FATTY ACID;

BIOGENESIS; BIOSYNTHESIS; BLUE GREEN ALGA; EPOXIDATION; EVOLUTION; GREEN ALGA; MARINE ENVIRONMENT; NONHUMAN; RED ALGA; REVIEW;

ALGAE; ALLYL COMPOUNDS; ANIMALS; CATIONS; EPOXY COMPOUNDS; ETHERS; FATTY ACIDS, UNSATURATED; FATTY ALCOHOLS; LACTONES; LIPIDS; MOLECULAR STRUCTURE; PROSTAGLANDINS;

ALGAE; CHLOROPHYTA; CYANOBACTERIA; MAMMALIA; RHODOPHYTA;

EID: 0030459935     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02587906     Document Type: Review

References (73)

1. Gerwick, W.H. (1994) Structure and Biosynthesis of Marine Algal Oxylipins, Biochim. Biophys. Acta 1211, 243-255.
2. Gerwick, W.H., and Bernart, M. (1993) Eicosanoids and Related Compounds from Marine Algae, in Advances in Marine Biotechnology: Pharmaceutical and Bioactive Natural Products (Attaway, D.H., and Zaborsky, O.R., eds.) Vol. 1, pp. 101-152, Plenum Press, New York.
3. Iguchi, K., Kaneta, S., Mori, K., Yamada, Y., Honda, A., and Mori, Y. (1986) Bromovulone I and lodovulone I, Unprecedented Brominated and Iodinated Marine Prostanoids with Antitumor Activity Isolated from the Japanese Stolonifer Clavularia viridis Quoy and Gaimard, J. Chem. Soc., Chem. Commun. 981-982.
4. Gerwick, W.H., Nagle, D.G., and Proteau, P.J. (1993) Oxylipins from Marine Invertebrates, in Topics in Current Chemistry (Scheuer, P.J., ed.) Vol. 167, Springer-Verlag, Berlin, pp. 117-180.
5. Gerwick, W.H. (1993) Carbocyclic Oxylipins of Marine Origin, Chem. Rev. 93, 1807-1823.
6. Honda, A., Yamamoto, Y., Mori, Y., Yamada, Y., and Kikuchi, H. (1985) Antileukemic Effect of Coral-Prostanoids Clavulones from the Stolonifer Clavularia viridis on Human Myeloid Leukemia (HL-60) Cells, Biochem. Biophys. Res. Commun. 130, 515-523.
7. Gerhart, D.J. (1991) Emesis, Learned Aversion, and Chemical Defense in Octocorals: a Central Role for Prostaglandins?, Am. J. Physiol 260, R839-R843.
8. Lands, W.E.M. (1986) Fish in Human Health, Academic Press, Orlando.
9. Proteau, P.J., and Gerwick, W.H. (1993) Divinyl Ethers and Hydroxy Fatty Acids from Three Species of Laminaria (Brown Algae), Lipids 28, 783-787.
10. Solem, M.L., Jiang, Z.D., and Gerwick, W.H. (1989) Three New and Bioactive Icosanoids from the Temperate Red Marine Alga Farlowia mollis, Lipids 24, 256-260.
11. Gerwick, W.H., Moghaddam, M.F., and Hamberg, M. (1991) Oxylipin Metabolism in the Red Alga Gracilariopsis lemaneiformis: Mechanism of Formation of Vicinal Dihydroxy Fatty Acids, Arch. Biochem. Biophys. 290, 436-444.
12. Sok, D.E., and Kim, M.R. (1994) Conversion of α-Linolenic Acid to Dihydro(pero)xyoctadecatrienoic Acid Isomers by Soybean and Potato Lipoxygenases, J. Agric. Food Chem. 42, 2703-2708.
13. 2 Synthetase Complex from Plexaura homomalla, J. Am. Chem. Soc. 95, 2054-2055.
14. Hamberg, M., and Gerwick, W.H. (1993) Biosynthesis of Vicinal Dihydroxy Fatty Acids in the Red Alga Gracilariopsis lemaneiformis: Identification of a Sodium-Dependent 12-Lipoxygenase and a Hydroperoxide Isomerase, Arch. Biochem. Biophys. 305, 115-122.
15. Hawkins, D.J., and Brash, A.R. (1989) Mechanism of Biosynthesis of 11R- and 12R-Hydroxyeicosatetraenoic Acids by Eggs of the Sea Urchin, FEBS Lett. 247, 9-12.
16. Gaffney, B.J., Boyington, J.C., Amzel, L.M., Doctor, K.S., Progge, S.T., and Yuan, S.M. (1995) Lipoxygenase Structure and Mechanism, Adv. Prostaglandin Thromboxane Leukotriene Res. 23, 11-16.
17. Gardner, H.W. (1991) Recent Investigations into the Lipoxygenase Pathway of Plants, Biochim. Biophys. Acta 1084, 221-239.
18. Vick, B.A., and Zimmerman, D.C. (1987) Pathways of Fatty Acid Hydroperoxide Metabolism in Spinach Leaf Chloroplasts, Plant Physiol. 85, 1073-1078.
19. Song, W.-C., and Brash, A.R. (1991) Purification of an Allene Oxide Synthase and identification of the Enzyme as a Cytochrome P-450, Science 253, 781-784.
20. Song, W.-C., Baertschi, S.W., Boeglin, W.E., Harris, T.M., and Brash, A.R. (1993) Formation of Epoxyalcohols by a Purified Allene Oxide Synthase, J. Biol. Chem. 268, 6293-6298.
21. Ullrich, V., and Brugger, R. (1994) Prostacyclin and Thromboxane Synthase: New Aspects of Hemethiolate Catalysis, Angew. Chem. Int. Ed. Engl. 33, 1911-1919.
22. Hamberg, M. (1987) Mechanism of Corn Hydroperoxide Isomerase: Detection of 12,13(S)-oxido-9(Z), 11-Octadecadienoic Acid, Biochim. Biophys. Acta 920, 76-84.
23. Corey, E.J., Matsuda, S.P.T., Nagata, R., and Cleaver, M.B. (1988) Biosynthesis of 8-R-HPETE and Preclavulone-A from Arachidonate in Several Species of Caribbean Coral. A Widespread Route to Marine Prostanoids, Tetrahedron Lett. 29, 2555-2558.
24. 2 from 15-Hydroxyeicosatetraenoic Acid, Archiv. Biochem. Biophys. 290, 427-433.
25. Gardner, H.W. (1984) Acid Catalysis of a Linoleic Acid Hydroperoxide: Formation of Epoxides by an Intramolecular Cyclization of the Hydroperoxide Group, J. Org. Chem. 49, 508-515.
26. Gardner, H.W. (1979) Stereospecificity of Linoleic Acid Hydroperoxide Isomerase from Corn Germ, Lipids 14, 208-211.
27. ′Z)-dienyloxy]non-(8E)-enoic (Colneleic) Acid and (13R)-Hydroxy-12-oxo-octadec-(9Z)-enoic Acid by Plant Enzymes, J. Chem. Soc., Chem. Commun., 503-504.
28. 18O]Hydroperoxylinolenic Acid by Hydroperoxide Cyclase, Lipids 15, 468-471.
29. 2]Hydroperoxyoctadeca(10E),(12Z)-dienoic Acid, J. Chem. Soc., Chem. Commun., 502-503.
30. Corey, E.J., De, B., Ponder, J.W., and Berg, J.M. (1984) The Stereochemistry and Biosynthesis of Hybridalactone, an Eicosanoid from Laurencia hybrida, Tetrahedron Lett. 25, 1015-1018.
31. Nagle, D.G., and Gerwick, W.H. (1994) Structure and Stereo-chemistry of Constanolactones A-G, Lactonized Cyclopropyl Oxylipins from the Red Marine Alga Constantinea simplex, J. Org. Chem. 59, 7227-7237.
32. Todd, J.S., Proteau, P.J., and Gerwick, W.H. (1993) Egregiachlorides A-C: New Chlorinated Oxylipins from the Marine Brown Alga Egregia menziesii, Tetrahedron Lett. 34, 7689-7692.
33. Moghaddam, M.F., Gerwick, W.H., and Ballantine, D.L. (1990) Discovery of the Mammalian Insulin Release Modulator Hepoxilin B3 from the Tropical Red Algae Platysiphonia miniata and Cottoniella filamentosa, J. Biol. Chem. 265, 6126-6130.
34. Bernart, M.W., and Gerwick, W.H. (1994) Eicosanoids from the Tropical Red Alga Murrayella periclados, Phytochemistry 36, 1233-1240.
35. Hamberg, M. (1992) A Method for Determination of the Absolute Stereochemistry of α,β-Epoxy Alcohols Derived from Fatty Acid Hydroperoxides, Lipids 27, 1042-1046.
36. Bernart, M.W., and Gerwick, W.H. (1988) Isolation of 12-(S)-HEPE from the Red Marine Alga Murrayella periclados and Revision of Structure of an Acyclic Icosanoid from Laurencia hybrida. Implications to the Biosynthesis of the Marine Prostanoid Hybridalactone, Tetrahedron Lett. 29, 2015-2018.
37. Jiang, Z.-D. (1992) Novel Oxylipins and Heterocycles from the Rhodophyta and Cyanophyta, Ph.D Thesis, Oregon State University, Corvallis, pp. 62-87.
38. Cardellina II, J.H., and Moore, R.E. (1980) Malyngic Acid, A New Fatty Acid from Lyngbya majuscula, Tetrahedron 36, 993-996.
39. Pace-Asciak, C.R., Reynaud, D., and Demin, P.M. (1995) Hepoxilins: A Review on Their Enzymatic Formation, Metabolism and Chemical Synthesis, Lipids 30, 107-114.
40. 3-C, a Glutathione Conjugate, Biochim. Biophys. Acta 1084, 60-68.
41. Galliard, T., Phillips, D.R., and Frost, D.J. (1973) Novel Divinyl Ether Fatty Acids in Extracts of Solanum tuberosum, Chem. Phys. Lipids 11, 173-180.
42. Galliard, T., and Matthew, J.A. (1975) Enzymic Reactions of Fatty Acid Hydroperoxides in Extracts of Potato Tuber, Biochim. Biophys. Acta 398, 1-9.
43. Fahlstadius, P., and Hamberg, M. (1990) Stereospecific Removal of the pro-R Hydrogen at C-8 of (9S)-Hydroperoxyoctadecadienoic Acid in the Biosynthesis of Colneleic Acid, J. Chem. Soc. Perkin Trans. 1, 2027-2030.
44. Andrianarison, R.-H., Beneytout, J.-L., and Tixier, M. (1989) An Enzymatic Conversion of Lipoxygenase Products by a Hydroperoxide Lyase in Blue-Green Algae (Oscillatoria sp.), Plant Physiol. 91, 1280-1287.
45. Proteau, P.J., and Gerwick, W.H. (1992) Cymathere Ethers A and B: Bicyclic Oxylipins from the Marine Brown Alga Cymathere triplicata, Tetrahedron Lett. 33, 4393-4396.
46. Roland, W.G. (1984) Resource Management Biology for the Edible Kelp Cymathere triplicata, Can. J. Fish. Aquat. Sci. 41, 271-277.
47. Druehl, L.D., Baird, R., Lindwall, A., Lloyd, K.E., and Pakula, S. (1988) Longline Cultivation of Some Laminariaceae in British Columbia, Canada, Aquacult. Fish. Manage. 19, 253-263.
48. Proteau, P.J. (1993) Oxylipins from Temperate Marine Algae and a Photoprotective Sheath Pigment from Blue-Green Algae, Ph.D. Thesis, Oregon State University, Corvallis, pp. 20-130.
49. Schieberle, P., Ofner, S., and Grosch, W. (1990) Evaluation of Potent Odorants in Cucumbers (Cucumis sativus) and Muskmelons (Cucumis melo) by Aroma Extract Dilution Analysis, J. Food Sci. 55, 193-195.
50. Niwa, H., Watanabe, M., Inagaki, H., and Yamada, K. (1994) Didemnilactones A and B and Neodidemnilactone, Three New Fatty Acid Metabolites Isolated from the Tunicate Didemnum moseleyi (Herdman), Tetrahedron 50, 7385-7400.
51. Congreve, M.S., Holmes, A.B., Hughes, A.B., and Looney, M.G. (1993) Ascidiatrienolide A is a 10-Membered Lactone, J. Am. Chem. Soc. 115, 5815-5816.
52. Lindquist, N., and Fenical, W. (1989) Ascidiatrienolides A-C, Novel Lactonized Eicosanoids from the Colonial Marine Ascidian Didemnum candidum, Tetrahedron Lett. 30, 2735-2738.
53. Bernart, M.W., Whatley, G., and Gerwick, W.H. (1993) Unprecedented Oxylipins from the Marine Green Alga Acrosiphonia coalita, J. Nat. Prod. 56, 245-259.
54. Nagle, D.G., and Gerwick, W.H. (1990) Constanolactones A and B, Novel Cyclopropyl Hydroxy Eicosanoids from the Temperate Red Alga Constantinea simplex, Tetrahedron Lett. 31, 2995-2998.
55. Nagle, D.G. (1994) Novel Oxylipins and Other Bioactive Metabolites from Marine Algae, Ph.D. Thesis, Oregon State University, Corvallis, pp. 50-126.
56. Niwa, H., Wakamatsu, K., and Yamada, K. (1989) Halicholactone and Neohalicholactone. Two Novel Fatty Acid Metabolites from the Marine Sponge Halichondria okadai Kadota, Tetrahedron Lett. 30, 4543-4546.
57. Kigoshi, H., Niwa, H., Yamada, K., Stout, T.J., and Clardy, J. (1991) The Three-Dimensional Structure of Neohalicholactone, an Unusual Fatty Acid Metabolite from the Marine Sponge Halichondria okadai Kadota, Tetrahedron Lett. 32, 24272428.
58. Proteau, P.J., Rossi, J.V., and Gerwick, W.H. (1994) Absolute Stereochemistry of Neohalicholactone from the Brown Alga Laminaria sinclairii, J. Nat. Prod. 57, 1717-1719.
59. Critcher, D.J., Connolly, S., and Wills, M. (1995) The Total Asymmetric Synthesis of Halicholactone and Neohalicholactone, Tetrahedron Lett. 36, 3763-3766.
60. Higgs, M.D., and Mulheirn, L.J. (1981) Hybridalactone, an Unusual Fatty Acid Metabolite from the Red Alga Laurencia hybrida (Rhodophyta, Rhodomelaceae), Tetrahedron 37, 4259-4262.
61. Higgs, M.D. (1981) Antimicrobial Components of the Red Alga Laurencia hybrida (Rhodophyta, Rhodomelaceae), Tetrahedron 37, 4255-4258.
62. Steinberg, P.D. (1995) Seasonal Variation in the Relationship Between Growth Rate and Phlorotannin Production in the Kelp Ecklonia radiata, Oecologia 102, 169-173.
63. Kurata, K., Taniguchi, K., Shiraishi, K., Hayama, N., Tanaka, I., and Suzuki, M., (1989) Ecklonialactone-A and -B, Two Unusual Metabolites from the Brown Alga Ecklonia stolonifera Okamura, Chemistry Lett., 267-270.
64. Kurata, K., Taniguchi, K., Shiraishi, K., and Suzuki, M. (1993) Ecklonialactones-C-F from the Brown Alga Ecklonia stolonifera, Phytochemistry 33, 155-159.
65. Todd, J.S., Proteau, P.J., and Gerwick, W.H. (1994) The Absolute Configuration of Ecklonialactones A, B, and E, Novel Oxylipins from Brown Algae of the Genera Ecklonia and Egregia, J. Nat. Prod. 57, 171-174.
66. Graber, M.A., Gerwick, W.H., and Cheney, D.P. (1996) The Isolation and Characterization of Agardhilactone, a Novel Oxylipin from the Marine Red Alga Agardhiella subulata, Tetrahedron Lett. 37, 4635-4638.
67. Wang, R., and Shimizu, Y. (1990) Bacillariolides I and II, a New Type of Cyclopentane Eicosanoids from the Diatom Nitzschia pungens, J. Chem. Soc., Chem. Commun. 413-414.
68. Novelli, A., Kispert, J., Fernandez-Sanchez, M.T., Torreblanca, A., and Zitko, V. (1992) Domoic Acid-Containing Toxic Mussels Produce Neurotoxicity in Neuronal Cultures Through a Synergism Between Excitatory Amino Acids, Brain Res. 577, 41-48.
69. Wang, R., Shimizu, Y., Steiner, J.R., and Clardy, J. (1993) The Absolute Configuration of Bacillariolides I and II, a New Type of Cyclopentane Icosanoids from a Marine Diatom, J. Chem. Soc., Chem. Commun. 379-381.
70. Coll, J.C. (1992) The Chemistry and Chemical Ecology of Octocorals (Coelenterata, Anthozoa, Octocorallia), Chem. Rev. 92, 613-631.
71. Iguchi, K., Kaneta, S., Mori, K., and Yamada, Y. (1987) A New Marine Epoxy Prostanoid With an Antiproliferative Activity from the Stolonifer Clavularia viridis Quoy and Gaimard, Chem. Pharm. Bull. 35, 4375-4376.
72. Baker, B.J., and Scheuer, P.J. (1994) The Puniglandins: 10-Chloroprostanoids from the Octocoral Telesto riisei, J. Nat. Prod. 57, 1346-1353.
73. 2, and Its Acetate, Methyl Ester) in the Gorgonian Plexaura homomalla Chemistry of Coelenterates. XV., Tetrahedron Lett., 5185-5188.