Journal
TETRAHEDRON
Volume 66, Issue 2, Pages 455-461Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.11.042
Keywords
Chemical ecology; Chemical defense; Antimicrobial; Sesquiterprene; Marine natural product; Macroalga; Peyssonnelia
Categories
Funding
- NSF-IGERT
- NIH ICBG [U01-TW007401]
- NSF [OCE-0726689]
- Direct For Biological Sciences
- Division Of Environmental Biology [919508] Funding Source: National Science Foundation
- Direct For Biological Sciences
- Division Of Environmental Biology [743024] Funding Source: National Science Foundation
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Pharmacologically-motivated marine natural product investigations have yielded a large variety of structurally unique compounds with interesting biomedical properties, but the natural roles of these molecules often remain unknown. While secondary metabolites may function as antimicrobial chemical defenses, few studies have examined this hypothesis. In the present investigation, chromatographic fractions from 69 collections of Fijian red macroalgae representing at least 43 species were evaluated for growth inhibition of three microbial pathogens and saprophytes of marine macrophytes. At least one microbe was suppressed by fraction(s) of all evaluated algae, suggesting that antimicrobial defenses are common among tropical seaweeds. From these leads, peyssonoic acids A-B (1-2), novel sesquiterpene hydroquinones, were isolated from the crustose red alga Peyssonnelia sp. At ecologically realistic concentrations, both compounds inhibited growth of Pseudoalteromonas bacteriolytica, a bacterial pathogen of marine algae, and Lindra thalassiae, a fungal pathogen of marine algae, and exhibited modest antineoplastic activity against ovarian cancer cells. The peyssonoic acids included one novel carbon skeleton and illustrated the utility of ecological studies in natural product discovery. (C) 2009 Elsevier Ltd. All rights reserved.
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