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

Research output: Contribution to journalArticle

26 Citations (Scopus)

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

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Metabolites
Veratridine
Polyketides
Sodium Channels
Neurons
Sodium
lipoamide
Cyanobacteria

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Nunnery, J. K., Engene, N., Byrum, T., Cao, Z., Jabba, S. V., Pereira, A. R., ... 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

Biosynthetically intriguing chlorinated lipophilic metabolites from geographically distant tropical marine cyanobacteria. / Nunnery, Joshawna K.; Engene, Niclas; Byrum, Tara; Cao, Zhengyu; Jabba, Sairam V.; Pereira, Alban R.; Matainaho, Teatulohi; Murray, Thomas F.; Gerwick, William H.

In: Journal of Organic Chemistry, Vol. 77, No. 9, 04.05.2012, p. 4198-4208.

Research output: Contribution to journalArticle

Nunnery, JK, Engene, N, Byrum, T, Cao, Z, Jabba, SV, Pereira, AR, Matainaho, T, Murray, TF & Gerwick, WH 2012, 'Biosynthetically intriguing chlorinated lipophilic metabolites from geographically distant tropical marine cyanobacteria', Journal of Organic Chemistry, vol. 77, no. 9, pp. 4198-4208. https://doi.org/10.1021/jo300160e
Nunnery, Joshawna K. ; Engene, Niclas ; Byrum, Tara ; Cao, Zhengyu ; Jabba, Sairam V. ; Pereira, Alban R. ; Matainaho, Teatulohi ; Murray, Thomas F. ; Gerwick, William H. / Biosynthetically intriguing chlorinated lipophilic metabolites from geographically distant tropical marine cyanobacteria. In: Journal of Organic Chemistry. 2012 ; Vol. 77, No. 9. pp. 4198-4208.
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