title: Lyngbyabellins K-N from Two Palmyra Atoll Collections of the Marine CyanobacteriumMoorea bouillonii.
abstract: Five lipopeptides of the lyngbyabellin structure class, four cyclic (1-3, and5) and one linear (4), were isolated from the extracts of two collections of filamentous marine cyanobacteria obtained from Palmyra Atoll in the Central Pacific Ocean. Their planar structures and absolute configurations were elucidated by combined 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, metabolites2and3possessed rare mono-chlorination on the 3-acyloxy-2-methyloctanoate residue while lyngbyabellin N (5) had an unusualN,N-dimethylvaline terminus. Lyngbyabellin N also possessed a leucine statine residue, and showed strong cytotoxic activity against HCT116 colon cancer cell line (IC50= 40.9 ± 3.3 nM).
authors.affiliation: Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California San Diego, 9500 Gilman Dr. MC 0212, La Jolla, CA, 92093, USA.
authors.forename: Hyukjae
authors.initials: H
authors.lastname: Choi
authors.affiliation: Department of Chemistry and Biochemistry, University of California San Diego,9500 Gilman Dr., La Jolla, CA, 92093, USA.
authors.forename: Emily
authors.initials: E
authors.lastname: Mevers
authors.affiliation: Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California San Diego, 9500 Gilman Dr. MC 0212, La Jolla, CA, 92093, USA.
authors.forename: Tara
authors.initials: T
authors.lastname: Byrum
authors.affiliation: Division of Hematology & Oncology, Department of Internal Medicine, Henry Ford Hospital, Detroit, MI, 48202, USA.
authors.forename: Frederick A
authors.initials: FA
authors.lastname: Valeriote
authors.affiliation: Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California San Diego, 9500 Gilman Dr. MC 0212, La Jolla, CA, 92093, USA.|Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego, La Jolla, CA, 92093, USA.
authors.forename: William H
authors.initials: WH
authors.lastname: Gerwick
keywords: Biological Activity; Natural Products; Peptides; Structure Elucidation