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

doi:10.1021/jo300160e

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

Department of Pharmacology and Neuroscience

Research output: Contribution to journal › Article › peer-review

28 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 language	English (US)
Pages (from-to)	4198-4208
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	77
Issue number	9
DOIs	https://doi.org/10.1021/jo300160e
State	Published - May 4 2012

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo300160e

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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 journal › Article › peer-review

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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 Cura{\c c}ao 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.",

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AU - Nunnery, Joshawna K.

AU - Engene, Niclas

AU - Byrum, Tara

AU - Cao, Zhengyu

AU - Jabba, Sairam V.

AU - Pereira, Alban R.

AU - Matainaho, Teatulohi

AU - Murray, Thomas F.

AU - Gerwick, William H.

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AB - 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.

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Biosynthetically intriguing chlorinated lipophilic metabolites from geographically distant tropical marine cyanobacteria

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