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

doi:10.1021/ol101752n

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

Department of Pharmacology and Neuroscience

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

62 Scopus citations

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 language	English (US)
Pages (from-to)	4490-4493
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	20
DOIs	https://doi.org/10.1021/ol101752n
State	Published - Oct 15 2010

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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.",

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AU - Pereira, Alban R.

AU - Cao, Zhengyu

AU - Engene, Niclas

AU - Soria-Mercado, Irma E.

AU - Murray, Thomas F.

AU - Gerwick, William H.

PY - 2010/10/15

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N2 - 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.

AB - 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.

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

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