Isolation and biological evaluation of 8-epi-malyngamide C from the Floridian marine cyanobacterium Lyngbya majuscula.
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.
Kwan
Jason C
JC
Department of Medicinal Chemistry, University of Florida, Gainesville, Florida 32610, USA.
Teplitski
Max
M
Gunasekera
Sarath P
SP
Paul
Valerie J
VJ
Luesch
Hendrik
H
D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000458:Cyanobacteria / Q000737:chemistry*; D003512:Cyclohexanones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D005229:Fatty Acids, Monounsaturated / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D005431:Florida; D019073:HT29 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D053038:Quorum Sensing / Q000502:physiology; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D003512:Cyclohexanones; D005229:Fatty Acids, Monounsaturated; C548940:malyngamide C