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

TETRAHEDRON LETTERS

卷:57

Article

Bertin, Matthew J.¹  Zimba, Paul V.²  He, Haiyin³  Moeller, Peter D. R.⁴ 

[1] Univ Rhode Isl, Dept Biomed & Pharmaceut Sci, Coll Pharm, 7 Greenhouse Rd, Kingston, RI 02881 USA

[2] Texas A&M, Dept Life Sci, 6300 Ocean Dr, Corpus Christi, TX 78412 USA

[3] Biosortia Pharmaceut, Hollings Marine Lab, 331 Ft Johnson Rd, Charleston, SC 29412 USA

[4] NOAA, Emerging Toxins Program, Natl Ocean Serv, Hollings Marine Lab, 331 Ft Johnson Rd, Charleston, SC 29412 USA

关键词: Cyanobacteria blooms;    Trichodesmium thiebautii;    Polyketide;    Trichotoxin;   

DOI  :  10.1016/j.tetlet.2016.11.062

来源: Elsevier

【 摘 要 】

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 analog (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 analog trichotoxin B (2). Absolute configuration of 1 and 2 is proposed based on spectroscopic comparison to a close structural analog. (C) 2016 Elsevier Ltd. All rights reserved.

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