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Literature DB >> 32153305

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

Matthew J Bertin¹, Paul V Zimba², Haiyin He³, Peter D R Moeller⁴.

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.

Entities: CellLine Chemical Disease Species

Keywords: Cyanobacteria blooms; Trichodesmium thiebautii; polyketide; trichotoxin

Year: 2016 PMID： 32153305 PMCID： PMC7062361 DOI： 10.1016/j.tetlet.2016.11.062

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

19 in total

1. Credneramides A and B: neuromodulatory phenethylamine and isopentylamine derivatives of a vinyl chloride-containing fatty acid from cf. Trichodesmium sp. nov.

Authors: Karla L Malloy; Takashi L Suyama; Niclas Engene; Hosana Debonsi; Zhengyu Cao; Teatulohi Matainaho; Carmenza Spadafora; Thomas F Murray; William H Gerwick
Journal: J Nat Prod Date: 2011-12-12 Impact factor: 4.050

2. Two classes of metabolites from Theonella swinhoei are localized in distinct populations of bacterial symbionts.

Authors: C A Bewley; N D Holland; D J Faulkner
Journal: Experientia Date: 1996-07-15

Review 3. Biologically active secondary metabolites from marine cyanobacteria.

Authors: Joshawna K Nunnery; Emily Mevers; William H Gerwick
Journal: Curr Opin Biotechnol Date: 2010-10-26 Impact factor: 9.740

4. Biosynthetic origin of natural products isolated from marine microorganism-invertebrate assemblages.

Authors: T Luke Simmons; R Cameron Coates; Benjamin R Clark; Niclas Engene; David Gonzalez; Eduardo Esquenazi; Pieter C Dorrestein; William H Gerwick
Journal: Proc Natl Acad Sci U S A Date: 2008-02-04 Impact factor: 11.205

Review 5. Biosynthesis of polyketide synthase extender units.

Authors: Yolande A Chan; Angela M Podevels; Brian M Kevany; Michael G Thomas
Journal: Nat Prod Rep Date: 2009-01 Impact factor: 13.423

6. A novel natural phenyl alkene with cytotoxic activity.

Authors: In Hyun Hwang; Joonseok Oh; Anna Kochanowska-Karamyan; Robert J Doerksen; MinKyun Na; Mark T Hamann
Journal: Tetrahedron Lett Date: 2013-05-18 Impact factor: 2.415

7. Terminal alkene formation by the thioesterase of curacin A biosynthesis: structure of a decarboxylating thioesterase.

Authors: Jennifer J Gehret; Liangcai Gu; William H Gerwick; Peter Wipf; David H Sherman; Janet L Smith
Journal: J Biol Chem Date: 2011-02-27 Impact factor: 5.157

8. Biosynthetic pathway and gene cluster analysis of curacin A, an antitubulin natural product from the tropical marine cyanobacterium Lyngbya majuscula.

Authors: Zunxue Chang; Namthip Sitachitta; James V Rossi; Mary Ann Roberts; Patricia M Flatt; Junyong Jia; David H Sherman; William H Gerwick
Journal: J Nat Prod Date: 2004-08 Impact factor: 4.050

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

1. Credneramides A and B: neuromodulatory phenethylamine and isopentylamine derivatives of a vinyl chloride-containing fatty acid from cf. Trichodesmium sp. nov.

2. Two classes of metabolites from Theonella swinhoei are localized in distinct populations of bacterial symbionts.

Review 3. Biologically active secondary metabolites from marine cyanobacteria.

4. Biosynthetic origin of natural products isolated from marine microorganism-invertebrate assemblages.

Review 5. Biosynthesis of polyketide synthase extender units.

6. A novel natural phenyl alkene with cytotoxic activity.

7. Terminal alkene formation by the thioesterase of curacin A biosynthesis: structure of a decarboxylating thioesterase.

8. Biosynthetic pathway and gene cluster analysis of curacin A, an antitubulin natural product from the tropical marine cyanobacterium Lyngbya majuscula.

Review 9. Isoprenoid-like alkylations in polyketide biosynthesis.

Review 10. Trichodesmium--a widespread marine cyanobacterium with unusual nitrogen fixation properties.

1. Trichothiazole A, a dichlorinated polyketide containing an embedded thiazole isolated from Trichodesmium blooms.

2. Isolation of Isotrichophycin C and Trichophycins G-I from a Collection of Trichodesmium thiebautii.