Isolation and biological evaluation of 8-epi-malyngamide C from the Floridian marine cyanobacterium Lyngbya majuscula.

Abstract

A new stereoisomer of malyngamide C, 8-epi-malyngamide C (1), and the known compound lyngbic acid [(4E,7S)-7-methoxytetradec-4-enoic acid] were isolated from a sample of Lyngbya majuscula collected near Bush Key, Dry Tortugas, Florida. The structure of 1 was determined by NMR and MS experiments. The absolute configuration of 1 was determined by selective Mitsunobu inversion of C-8 to give malyngamide C, as determined by NMR, MS, and comparison of specific rotation. Both 1 and malyngamide C were found to be cytotoxic to HT29 colon cancer cells (IC(50) 15.4 and 5.2 microM, respectively) and to inhibit bacterial quorum sensing in a reporter gene assay.

• Authors: Jason C Kwan, Max Teplitski, Sarath P Gunasekera, Valerie J Paul, Hendrik Luesch
• Journal: Journal of natural products (J Nat Prod) Vol. 73 Issue 3 Pg. 463-6 (Mar 26 2010) ISSN: 1520-6025 [Electronic] United States
• PMID: 20166701 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents
• Cyclohexanones
• Fatty Acids, Monounsaturated
• malyngamide C

Topics

• Antineoplastic Agents (chemistry, isolation & purification, pharmacology)
• Cyanobacteria (chemistry)
• Cyclohexanones (chemistry, isolation & purification, pharmacology)
• Drug Screening Assays, Antitumor
• Fatty Acids, Monounsaturated (chemistry, isolation & purification, pharmacology)
• Florida
• HT29 Cells
• Humans
• Inhibitory Concentration 50
• Marine Biology
• Molecular Structure
• Nuclear Magnetic Resonance, Biomolecular
• Quorum Sensing (physiology)
• Stereoisomerism