Parazoanthines A-E, hydantoin alkaloids from the mediterranean sea anemone Parazoanthus axinellae

Nadja Cachet; Grégory Genta-Jouve; Erik L. Regalado; Redouane Mokrini; Philippe Amade; Gérald Culioli; Olivier P. Thomas

doi:10.1021/np900437y

Parazoanthines A-E, hydantoin alkaloids from the mediterranean sea anemone Parazoanthus axinellae

Nadja Cachet, Grégory Genta-Jouve, Erik L. Regalado, Redouane Mokrini, Philippe Amade, Gérald Culioli, Olivier P. Thomas

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

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Abstract

Five new hydantoin alkaloids, named parazoanthines A-E (1-5), were isolated as the major constituents of the Mediterranean sea anemone Parazoanthus axinellae. Their structural elucidation was achieved through NMR spectroscopic and mass spectrometric analyses. The absolute configuration of the chiral compounds 1 and 4 was determined by comparison between experimental and TDDFT-calculated CD spectra. The configuration of the trisubstituted double bond of 2, 3, and 5 was deduced from the ³J_H6-C4 coupling constant value. This family of alkaloids represents the first example of natural 3,5-disubstituted hydantoins that do not exhibit a methyl at N-3. All compounds were tested for their natural toxicity (Microtox assay), and parazoanthine C (3) exhibited the highest natural toxicity.

Original language	English
Pages (from-to)	1612-1615
Number of pages	4
Journal	Journal of Natural Products
Volume	72
Issue number	9
DOIs	https://doi.org/10.1021/np900437y
Publication status	Published - 25 Sep 2009
Externally published	Yes

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title = "Parazoanthines A-E, hydantoin alkaloids from the mediterranean sea anemone Parazoanthus axinellae",

abstract = "Five new hydantoin alkaloids, named parazoanthines A-E (1-5), were isolated as the major constituents of the Mediterranean sea anemone Parazoanthus axinellae. Their structural elucidation was achieved through NMR spectroscopic and mass spectrometric analyses. The absolute configuration of the chiral compounds 1 and 4 was determined by comparison between experimental and TDDFT-calculated CD spectra. The configuration of the trisubstituted double bond of 2, 3, and 5 was deduced from the 3JH6-C4 coupling constant value. This family of alkaloids represents the first example of natural 3,5-disubstituted hydantoins that do not exhibit a methyl at N-3. All compounds were tested for their natural toxicity (Microtox assay), and parazoanthine C (3) exhibited the highest natural toxicity.",

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T1 - Parazoanthines A-E, hydantoin alkaloids from the mediterranean sea anemone Parazoanthus axinellae

AU - Cachet, Nadja

AU - Genta-Jouve, Grégory

AU - Regalado, Erik L.

AU - Mokrini, Redouane

AU - Amade, Philippe

AU - Culioli, Gérald

AU - Thomas, Olivier P.

PY - 2009/9/25

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N2 - Five new hydantoin alkaloids, named parazoanthines A-E (1-5), were isolated as the major constituents of the Mediterranean sea anemone Parazoanthus axinellae. Their structural elucidation was achieved through NMR spectroscopic and mass spectrometric analyses. The absolute configuration of the chiral compounds 1 and 4 was determined by comparison between experimental and TDDFT-calculated CD spectra. The configuration of the trisubstituted double bond of 2, 3, and 5 was deduced from the 3JH6-C4 coupling constant value. This family of alkaloids represents the first example of natural 3,5-disubstituted hydantoins that do not exhibit a methyl at N-3. All compounds were tested for their natural toxicity (Microtox assay), and parazoanthine C (3) exhibited the highest natural toxicity.

AB - Five new hydantoin alkaloids, named parazoanthines A-E (1-5), were isolated as the major constituents of the Mediterranean sea anemone Parazoanthus axinellae. Their structural elucidation was achieved through NMR spectroscopic and mass spectrometric analyses. The absolute configuration of the chiral compounds 1 and 4 was determined by comparison between experimental and TDDFT-calculated CD spectra. The configuration of the trisubstituted double bond of 2, 3, and 5 was deduced from the 3JH6-C4 coupling constant value. This family of alkaloids represents the first example of natural 3,5-disubstituted hydantoins that do not exhibit a methyl at N-3. All compounds were tested for their natural toxicity (Microtox assay), and parazoanthine C (3) exhibited the highest natural toxicity.

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Parazoanthines A-E, hydantoin alkaloids from the mediterranean sea anemone Parazoanthus axinellae

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