1996-Marine Natural Products

Marine Natural Products D. John Faulkner Scripps Institution of Oceanography, University of California, San Diego, La Jolla, CA 92093-02 12, USA ~~~~~~~~~~

Reviewing the literature published during 1994 (Continuing the coverage of literature in Natural Product Reports, 1995, Vol. 12, p. 223) 1 2 3

4 5 6 7 8 9 10 11 12 13

Introduction Marine Microorganisms and Phytoplankton Green Algae Brown Algae Red Algae Sponges Coelenterates Bryozoans Molluscs Tunica tes Echinoderms Miscellaneous References

2 Marine Microorganisms and Phytoplankton Marine bacteria are rapidly becoming recognized as potentially useful sources of compounds of biomedical interest. While it is common to find metabolites previously isolated from terrestrial microorganisms in bacteria from coastal waters, those bacteria isolated from deeper waters or from the tissues of marine algae, invertebrates and fishes have yielded some interesting new compounds. This is not always the case, however, as is demonstrated by the isolation of o-aminophenol (1) as the OH

1 Introduction This Report is a review of the literature of marine natural product chemistry for 1994. Earlier reports published in this journal cover the period from 1977 to December 1993.'-" The format for this review is identical to that of the previous reports, except that compounds from cyanobacteria (or blue-green algae) are now included in the section on marine microorganisms and phytoplankton. The review does not provide a comprehensive coverage of all research involving chemicals from marine organisms but concentrates on reports of novel marine natural products with interesting biological and pharmaceutical properties. Biochemical studies involving marine organisms and reports of primary metabolites are specifically omitted. Research on the biosynthesis of marine natural products has been reviewed in detail elsewherel2, and l3 is not included in this report. Wherever possible, the biological and pharmacological properties of new marine natural products have been reported but papers detailing the pharmacological studies are beyond the scope of this review. In the area of synthetic organic chemistry, the review focuses on reports of the total synthesis of marine natural products or close analogues, particularly those papers that redefine chemical structures. No attempt has been made to review the patent literature or conference abstracts and reports. The spate of excellent reviews that appeared in 1993 was followed by a relative dearth of such reviews in 1994. Four of these reviews, ' Oxylipins from marine invertebrates ',14 ' Structure and biosynthesis of marine algal oxylipins ',15 ' New marine prostanoids, clavulones, halogenovulones, and punaglandins',16 and 'Aquatic invertebrates open up new perspectives in eicosanoid research: biosynthesis and bioactivity ',17 all emphasize the wide distribution of eicosanoids and related compounds throughout the marine environment. A short review of ' Strategies for the discove

ry of secondary metabolites from marine bacteria ' stresses the differences between marine and terrestrial bacteria. An interesting historical account of ciguatera research is found in 'Ciguatera and its off-shootschance encounters en route to a molecular structure'.lg A review entitled 'The discovery of marine natural products with therapeutic potential '20 provides a realistic overview of the contributions of marine natural products research to the drug discovery effort. 75

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1

(2)

antimicrobial agent from a purple bacterium isolated from a sponge of the genus Adocia.21A symmetrical bis-indole, 7,7bis(3-indolyl)-p-cresol (2), was isolated as an antimicrobial constituent of a Vibrio sp. that was isolated from the marine sponge Hyatella sp.22Similar bis-indoles, vibrindole A (3) and the known metabolite 2,2-di(3-indolyl)-3-indolone (4),23were

H (4)

H

obtained from a strain of Vibrioparahaemolyticus isolated from .~~ the toxic mucus of the boxfish Ostracion c u b i c u~Trisindoline ( 5 ) is an isomer of (4)that was produced by a Vibrio sp. isolated from the sponge Hyrtios~ l t u mVibrio gazogenes ATCC29988, .~~ which was isolated from a marine mud sample, contained magnesidin A (6) as a mixture of tautomers.26An isolate of the

(5)

Mg2+ 2

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