Structure revision of trichotoxin, a chlorinated polyketide isolated from a Trichodesmium thiebautii bloom. Issue 52 (28th December 2016)

• Record Type: Journal Article
• Authors: Bertin, Matthew J.; Zimba, Paul V.; He, Haiyin; Moeller, Peter D.R.
• Is Part Of: Tetrahedron letters. Volume 57:Issue 52(2016)
• Page Start: 5864
• Page End: 5867
• Publication Date: 2016-12-28
• Subjects: Cyanobacteria blooms -- Trichodesmium thiebautii -- Polyketide -- Trichotoxin; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.11.062
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: We have re-isolated and revised the original structure of the trichotoxin. Comparison of spectroscopic data provides strong support for revision. We have isolated and characterized an analog, trichotoxin B. 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 analog (2 ). Comparison of spectroscopic and spectrometric data of1 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 of1 and2 is proposed based on spectroscopic comparison to a close structural analog.