Literature DB >> 32189813

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

Richard S Belisle1, Christopher W Via1, Tracey B Schock2, Tracy A Villareal3, Paul V Zimba4, Kevin R Beauchesne5, Peter D R Moeller5, Matthew J Bertin1.   

Abstract

Mass spectrometry-guided isolation of the lipophilic extract of Trichodesmium bloom material led to the isolation and structure characterization of a new thiazole-containing di-chlorinated polyketide (1). The structure of 1 was deduced using 1D and 2D NMR analysis, high-resolution mass spectrometry analysis and complementary spectroscopic procedures. Trichothiazole A possesses interesting structural features, such as a terminal alkyne, two vinyl chlorides and a 2,4-disubstituted thiazole. Trichothiazole A showed moderate cytotoxicity to Neuro-2A cells (EC50: 13.3 ± 1.1 μM).

Entities:  

Keywords:  Trichodesmium; heterocycles; thiazole

Year:  2017        PMID: 32189813      PMCID: PMC7079771          DOI: 10.1016/j.tetlet.2017.09.027

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


  10 in total

1.  Barbamide, a chlorinated metabolite with molluscicidal activity from the Caribbean cyanobacterium Lyngbya majuscula.

Authors:  J Orjala; W H Gerwick
Journal:  J Nat Prod       Date:  1996-04       Impact factor: 4.050

2.  WS75624 A and B, new endothelin converting enzyme inhibitors isolated from Saccharothrix sp. No. 75624. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities.

Authors:  Y Tsurumi; H Ueda; K Hayashi; S Takase; M Nishikawa; S Kiyoto; M Okuhara
Journal:  J Antibiot (Tokyo)       Date:  1995-10       Impact factor: 2.649

3.  Biosynthetically intriguing chlorinated lipophilic metabolites from geographically distant tropical marine cyanobacteria.

Authors:  Joshawna K Nunnery; Niclas Engene; Tara Byrum; Zhengyu Cao; Sairam V Jabba; Alban R Pereira; Teatulohi Matainaho; Thomas F Murray; William H Gerwick
Journal:  J Org Chem       Date:  2012-04-19       Impact factor: 4.354

4.  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

5.  Total synthesis and biological evaluation of +-kalkitoxin, a cytotoxic metabolite of the cyanobacterium Lyngbya majuscula.

Authors:  James D White; Qing Xu; Chang-Sun Lee; Frederick A Valeriote
Journal:  Org Biomol Chem       Date:  2004-06-28       Impact factor: 3.876

Review 6.  Isoprenoid-like alkylations in polyketide biosynthesis.

Authors:  Christopher T Calderone
Journal:  Nat Prod Rep       Date:  2008-06-18       Impact factor: 13.423

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

Authors:  Matthew J Bertin; Paul V Zimba; Haiyin He; Peter D R Moeller
Journal:  Tetrahedron Lett       Date:  2016-11-15       Impact factor: 2.415

8.  Structure and absolute stereochemistry of hectochlorin, a potent stimulator of actin assembly.

Authors:  Brian L Marquez; Karl Shawn Watts; Alexandre Yokochi; Mary Ann Roberts; Pascal Verdier-Pinard; Jorge I Jimenez; Ernest Hamel; Paul J Scheuer; William H Gerwick
Journal:  J Nat Prod       Date:  2002-06       Impact factor: 4.050

9.  Structure and biosynthesis of the jamaicamides, new mixed polyketide-peptide neurotoxins from the marine cyanobacterium Lyngbya majuscula.

Authors:  Daniel J Edwards; Brian L Marquez; Lisa M Nogle; Kerry McPhail; Douglas E Goeger; Mary Ann Roberts; William H Gerwick
Journal:  Chem Biol       Date:  2004-06

10.  Wewakazole, a novel cyclic dodecapeptide from a Papua New Guinea Lyngbya majuscula.

Authors:  Lisa M Nogle; Brian L Marquez; William H Gerwick
Journal:  Org Lett       Date:  2003-01-09       Impact factor: 6.005

  10 in total

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