Lyngbyabellins K–N from Two Palmyra Atoll Collections of the Marine Cyanobacterium Moorea bouillonii

European Journal of Organic Chemistry - Tập 2012 Số 27 - Trang 5141-5150 - 2012
Hyukjae Choi1, Emily Mevers2, Tara Byrum1, Frederick A. Valeriote3, William H. Gerwick4,5
1Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California San Diego, 9500 Gilman Dr. MC 0212, La Jolla, CA 92093, USA, Fax: +1-858-534-0529 Homepage: http://gerwick.ucsd.edu/
2Department of Chemistry and Biochemistry, University of California San Diego, 9500 Gilman Dr, La Jolla, CA 92093, USA.
3Division of Hematology & Oncology, Department of Internal Medicine, Henry Ford Hospital, Detroit, MI 48202, USA
4Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California San Diego, 9500 Gilman Dr. MC 0212, La Jolla, CA 92093, USA, Fax: +1‐858‐534‐0529 Homepage: http://gerwick.ucsd.edu/
5Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, La Jolla, CA 92093, USA

Tóm tắt

AbstractFive lipopeptides of the lyngbyabellin structure class, four cyclic (1–3 and 5) and one linear (4), were isolated from the extracts of two collections of filamentous marine cyanobacteria obtained from the Palmyra Atoll in the Central Pacific Ocean. Their planar structures and absolute configurations were elucidated through a combination of spectroscopic and chromatographic analyses as well as chemical synthesis of fragments. In addition to structural features typical of the lyngbyabellins, such as two thiazole rings and a chlorinated 2‐methyloctanoate residue, these new compounds possess several unique aspects. Of note, metabolites 2 and 3 possess rare monochlorination on the 3‐acyloxy‐2‐methyloctanoate residue, whereas lyngbyabellin N (5) has an unusual N,N‐dimethylvaline terminus. Lyngbyabellin N also possesses a leucine statine residue and shows strong cytotoxic activity against the HCT116 colon cancer cell line (IC50 = 40.9 ± 3.3 nM).

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European Journal of Organic Chemistry

Tập 2012 Số 27

5141-5150

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