Palmyrolide A, an unusually stabilized neuroactive macrolide from palmyra atoll cyanobacteria

Alban R. Pereira, Zhengyu Cao, Niclas Engene, Irma E. Soria-Mercado, Thomas F. Murray, William H. Gerwick

Research output: Contribution to journalArticle

49 Citations (Scopus)

Abstract

Palmyrolide A (1) is a new neuroactive macrolide isolated from a marine cyanobacterial assemblage composed of Leptolyngbya cf. and Oscillatoria spp. collected from Palmyra Atoll. It features a rare N-methyl enamide and an intriguing t-butyl branch; the latter renders the adjacent lactone ester bond resistant to hydrolysis. Consistent with its significant suppression of calcium influx in cerebrocortical neurons (IC50 = 3.70 μM), palmyrolide A (1) showed a relatively potent sodium channel blocking activity in neuro-2a cells (IC50 = 5.2 μM), without appreciable cytotoxicity.

Original languageEnglish
Pages (from-to)4490-4493
Number of pages4
JournalOrganic Letters
Volume12
Issue number20
DOIs
StatePublished - Oct 15 2010

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Macrolides
Cyanobacteria
neurons
Inhibitory Concentration 50
hydrolysis
esters
calcium
Oscillatoria
retarding
Sodium Channels
Lactones
Cytotoxicity
cells
Neurons
Hydrolysis
Esters
Calcium
palmyrolide A

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Pereira, A. R., Cao, Z., Engene, N., Soria-Mercado, I. E., Murray, T. F., & Gerwick, W. H. (2010). Palmyrolide A, an unusually stabilized neuroactive macrolide from palmyra atoll cyanobacteria. Organic Letters, 12(20), 4490-4493. https://doi.org/10.1021/ol101752n

Palmyrolide A, an unusually stabilized neuroactive macrolide from palmyra atoll cyanobacteria. / Pereira, Alban R.; Cao, Zhengyu; Engene, Niclas; Soria-Mercado, Irma E.; Murray, Thomas F.; Gerwick, William H.

In: Organic Letters, Vol. 12, No. 20, 15.10.2010, p. 4490-4493.

Research output: Contribution to journalArticle

Pereira, AR, Cao, Z, Engene, N, Soria-Mercado, IE, Murray, TF & Gerwick, WH 2010, 'Palmyrolide A, an unusually stabilized neuroactive macrolide from palmyra atoll cyanobacteria', Organic Letters, vol. 12, no. 20, pp. 4490-4493. https://doi.org/10.1021/ol101752n
Pereira, Alban R. ; Cao, Zhengyu ; Engene, Niclas ; Soria-Mercado, Irma E. ; Murray, Thomas F. ; Gerwick, William H. / Palmyrolide A, an unusually stabilized neuroactive macrolide from palmyra atoll cyanobacteria. In: Organic Letters. 2010 ; Vol. 12, No. 20. pp. 4490-4493.
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