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Structure revision of trichotoxin, a chlorinated polyketide isolated from a Trichodesmium thiebautii bloom.

ABSTRACT: NMR-guided fractionation of the lipophilic extract of Trichodesmium thiebautii filaments led to the isolation of a phenyl-containing chlorinated polyketide (1) and an alkyne-containing analogue (2). Comparison of spectroscopic and spectrometric data of 1 with the data of the previously reported trichotoxin, strongly suggested that these metabolites were identical and supports a structural revision of trichotoxin and its designation as trichotoxin A. In addition, we report the isolation and characterization of the alkyne-containing analogue trichotoxin B (2). Absolute configuration of 1 and 2 is proposed based on spectroscopic comparison to a close structural analog.

SUBMITTER: Bertin MJ

PROVIDER: S-EPMC7062361 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature

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Structure revision of trichotoxin, a chlorinated polyketide isolated from a Trichodesmium thiebautii bloom.

Bertin Matthew J MJ Zimba Paul V PV He Haiyin H Moeller Peter D R PDR

Tetrahedron letters 20161115 52

NMR-guided fractionation of the lipophilic extract of Trichodesmium thiebautii filaments led to the isolation of a phenyl-containing chlorinated polyketide (1) and an alkyne-containing analogue (2). Comparison of spectroscopic and spectrometric data of 1 with the data of the previously reported trichotoxin, strongly suggested that these metabolites were identical and supports a structural revision of trichotoxin and its designation as trichotoxin A. In addition, we re ...[more]

PMID: 32153305

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