Isolation and Biological Evaluation of 8-epi-Malyngamide C from the Floridian Marine Cyanobacterium Lyngbya majuscula
- 18 February 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Natural Products
- Vol. 73 (3), 463-466
- https://doi.org/10.1021/np900614n
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 (IC50 15.4 and 5.2 μM, respectively) and to inhibit bacterial quorum sensing in a reporter gene assay.Keywords
This publication has 32 references indexed in Scilit:
- Three New Malyngamides from a Papua New Guinea Collection of the Marine Cyanobacterium Lyngbya majusculaJournal of Natural Products, 2002
- A New Biologically Active Malyngamide from a New Zealand Collection of the Sea Hare Bursatella leachiiJournal of Natural Products, 2002
- Malyngamides O and P from the Sea Hare Stylocheilus longicaudaJournal of Natural Products, 2000
- Malyngamides M and N from the Hawaiian Red Alga Gracilaria coronopifoliaJournal of Natural Products, 1998
- Two malyngamides from the caribbean cyanobacterium Lyngbya majusculaPhytochemistry, 1987
- Structure of malyngamide CThe Journal of Organic Chemistry, 1985
- Malyngamide A, a novel chlorinated metabolite of the marine cyanophyte Lyngbya majusculaJournal of the American Chemical Society, 1979
- Stylocheilamide, an unusual constituent of the sea hare Stylocheilus longicaudaJournal of the American Chemical Society, 1978
- Malyngamides D and E, two trans-7-methoxy-9-methylhexadec-4-enamides from a deep water variety of the marine cyanophyte Lyngbya majusculaThe Journal of Organic Chemistry, 1978
- (−)-trans-7(S)-Methoxytetradec-4-enoic acid and related amides from the marine cyanophyte Lyngbya majusculaPhytochemistry, 1978