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

被引:10
作者
Belisle, Richard S. [1 ]
Via, Christopher W. [1 ]
Schock, Tracey B. [2 ]
Villareal, Tracy A. [3 ]
Zimba, Paul V. [4 ,5 ]
Beauchesne, Kevin R. [6 ]
Moeller, Peter D. R. [6 ]
Bertin, Matthew J. [1 ]
机构
[1] Univ Rhode Isl, Dept Biomed & Pharmaceut Sci, Coll Pharm, 7 Greenhouse Rd, Kingston, RI 02881 USA
[2] NIST, Hollings Marine Lab, 331 Ft Johnson Rd, Charleston, SC 29412 USA
[3] Univ Texas Austin, Marine Sci Inst, 750 Channel View Dr, Port Aransas, TX 78373 USA
[4] Texas A&M, Ctr Coastal Studies, 6300 Ocean Dr, Corpus Christi, TX 78412 USA
[5] Texas A&M, Dept Life Sci, 6300 Ocean Dr, Corpus Christi, TX 78412 USA
[6] Natl Ocean Serv, Emerging Toxins Program, NOAA, Hollings Marine Lab, 331 Ft Johnson Rd, Charleston, SC 29412 USA
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
Trichodesmium; Thiazole; Heterocycles; CYANOBACTERIUM LYNGBYA-MAJUSCULA; NATURAL-PRODUCT; CURACIN-A; BIOSYNTHESIS; HETEROCYCLES; METABOLITE;
D O I
10.1016/j.tetlet.2017.09.027
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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-2 A cells (EC50: 13.3 +/- 1.1 mu M). (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4066 / 4068
页数:3
相关论文
共 17 条
[1]   2,4-Disubstituted thiazoles as multitargated bioactive molecules [J].
Arora, Preeti ;
Narang, Rakesh ;
Nayak, Surendra Kumar ;
Singh, Sachin Kumar ;
Judge, Vikramjeet .
MEDICINAL CHEMISTRY RESEARCH, 2016, 25 (09) :1717-1743
[2]   Structure revision of trichotoxin, a chlorinated polyketide isolated from a Trichodesmium thiebautii bloom [J].
Bertin, Matthew J. ;
Zimba, Paul V. ;
He, Haiyin ;
Moeller, Peter D. R. .
TETRAHEDRON LETTERS, 2016, 57 (52) :5864-5867
[3]  
BERTIN MJ, 2017, MAR DRUGS, V15
[4]   Isoprenoid-like alkylations in polyketide biosynthesis [J].
Calderone, Christopher T. .
NATURAL PRODUCT REPORTS, 2008, 25 (05) :845-853
[5]   Biosynthetic pathway and gene cluster analysis of curacin A, an antitubulin natural product from the tropical marine cyanobacterium Lyngbya majuscula [J].
Chang, ZX ;
Sitachitta, N ;
Rossi, JV ;
Roberts, MA ;
Flatt, PM ;
Jia, JY ;
Sherman, DH ;
Gerwick, WH .
JOURNAL OF NATURAL PRODUCTS, 2004, 67 (08) :1356-1367
[6]   MYCOTHIAZOLE, A POLYKETIDE HETEROCYCLE FROM A MARINE SPONGE [J].
CREWS, P ;
KAKOU, Y ;
QUINOA, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (13) :4365-4368
[7]   Structure and biosynthesis of the jamaicamides, new mixed polyketide-peptide neurotoxins from the marine cyanobacterium Lyngbya majuscula [J].
Edwards, DJ ;
Marquez, BL ;
Nogle, LM ;
McPhail, K ;
Goeger, DE ;
Roberts, MA ;
Gerwick, WH .
CHEMISTRY & BIOLOGY, 2004, 11 (06) :817-833
[8]   STRUCTURE OF CURACIN-A, A NOVEL ANTIMITOTIC, ANTIPROLIFERATIVE, AND BRINE SHRIMP TOXIC NATURAL PRODUCT FROM THE MARINE CYANOBACTERIUM LYNGBYA-MAJUSCULA [J].
GERWICK, WH ;
PROTEAU, PJ ;
NAGLE, DG ;
HAMEL, E ;
BLOKHIN, A ;
SLATE, DL .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (06) :1243-1245
[9]   Heterocycles in drugs and drug discovery [J].
Gomtsyan, A. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2012, 48 (01) :7-10
[10]   Structure and absolute stereochemistry of hectochlorin, a potent stimulator of actin assembly [J].
Marquez, BL ;
Watts, KS ;
Yokochi, A ;
Roberts, MA ;
Verdier-Pinard, P ;
Jimenez, JI ;
Hamel, E ;
Scheuer, PJ ;
Gerwick, WH .
JOURNAL OF NATURAL PRODUCTS, 2002, 65 (06) :866-871