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Biosynthetically intriguing chlorinated lipophilic metabolites from geographically distant tropical marine cyanobacteria.

Publication ,  Journal Article
Nunnery, JK; Engene, N; Byrum, T; Cao, Z; Jabba, SV; Pereira, AR; Matainaho, T; Murray, TF; Gerwick, WH
Published in: The Journal of organic chemistry
May 2012

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.

Duke Scholars

Published In

The Journal of organic chemistry

DOI

EISSN

1520-6904

ISSN

0022-3263

Publication Date

May 2012

Volume

77

Issue

9

Start / End Page

4198 / 4208

Related Subject Headings

  • Vinyl Compounds
  • Thioctic Acid
  • Organic Chemistry
  • Nuclear Magnetic Resonance, Biomolecular
  • Neurotransmitter Agents
  • Molecular Structure
  • Mice
  • Halogenation
  • Geography
  • Cyanobacteria
 

Citation

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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. The Journal of Organic Chemistry, 77(9), 4198–4208. https://doi.org/10.1021/jo300160e
Nunnery, Joshawna K., Niclas Engene, Tara Byrum, Zhengyu Cao, Sairam V. Jabba, Alban R. Pereira, Teatulohi Matainaho, Thomas F. Murray, and William H. Gerwick. “Biosynthetically intriguing chlorinated lipophilic metabolites from geographically distant tropical marine cyanobacteria.The Journal of Organic Chemistry 77, no. 9 (May 2012): 4198–4208. https://doi.org/10.1021/jo300160e.
Nunnery JK, Engene N, Byrum T, Cao Z, Jabba SV, Pereira AR, et al. Biosynthetically intriguing chlorinated lipophilic metabolites from geographically distant tropical marine cyanobacteria. The Journal of organic chemistry. 2012 May;77(9):4198–208.
Nunnery, Joshawna K., et al. “Biosynthetically intriguing chlorinated lipophilic metabolites from geographically distant tropical marine cyanobacteria.The Journal of Organic Chemistry, vol. 77, no. 9, May 2012, pp. 4198–208. Epmc, doi:10.1021/jo300160e.
Nunnery JK, Engene N, Byrum T, Cao Z, Jabba SV, Pereira AR, Matainaho T, Murray TF, Gerwick WH. Biosynthetically intriguing chlorinated lipophilic metabolites from geographically distant tropical marine cyanobacteria. The Journal of organic chemistry. 2012 May;77(9):4198–4208.
Journal cover image

Published In

The Journal of organic chemistry

DOI

EISSN

1520-6904

ISSN

0022-3263

Publication Date

May 2012

Volume

77

Issue

9

Start / End Page

4198 / 4208

Related Subject Headings

  • Vinyl Compounds
  • Thioctic Acid
  • Organic Chemistry
  • Nuclear Magnetic Resonance, Biomolecular
  • Neurotransmitter Agents
  • Molecular Structure
  • Mice
  • Halogenation
  • Geography
  • Cyanobacteria