Biosynthetically intriguing chlorinated lipophilic metabolites from geographically distant tropical marine cyanobacteria

Joshawna K. Nunnery, Niclas Engene, Tara Byrum, Zhengyu Cao, Sairam V. Jabba, Alban R. Pereira, Teatulohi Matainaho, Thomas F. Murray, William H. Gerwick

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27 Scopus citations

Abstract

Five new vinylchlorine-containing metabolites, the lipoamides janthielamide A and kimbeamides A-C and the ketide-extended pyranone kimbelactone A, have been isolated from collections of marine cyanobacteria made in Curaçao and Papua New Guinea. Both janthielamide A and kimbeamide A exhibited moderate sodium channel blocking activity in murine Neuro-2a cells. Consistent with this activity, janthielamide A was also found to antagonize veratridine-induced sodium influx in murine cerebrocortical neurons. These lipoamides represent the newest additions to a relatively rare family of marine cyanobacterial-derived lipoamides and a new structural class of compounds exhibiting neuromodulatory activities from marine cyanobacteria.

Original languageEnglish (US)
Pages (from-to)4198-4208
Number of pages11
JournalJournal of Organic Chemistry
Volume77
Issue number9
DOIs
StatePublished - May 4 2012

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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    Nunnery, J. K., Engene, N., Byrum, T., Cao, Z., Jabba, S. V., Pereira, A. R., Matainaho, T., Murray, T. F., & Gerwick, W. H. (2012). Biosynthetically intriguing chlorinated lipophilic metabolites from geographically distant tropical marine cyanobacteria. Journal of Organic Chemistry, 77(9), 4198-4208. https://doi.org/10.1021/jo300160e