The marinopyrroles, antibiotics of an unprecedented structure class from a marine Streptomyces sp.

被引:236
作者
Hughes, Chambers C. [1 ]
Prieto-Davo, Alejandra [1 ]
Jensen, Paul R. [1 ]
Fenical, William [1 ]
机构
[1] Univ Calif San Diego, Scripps Inst Oceanog, Ctr Marine Biotechnol & Biomed, La Jolla, CA 92093 USA
关键词
D O I
10.1021/ol702952n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cultivation of an obligate marine Streptomyces strain has furnished the marinopyrroles A and B, densely halogenated, axially chiral metabolites that contain an uncommon bispyrrole structure. X-ray analysis of marinopyrrole B showed that the natural product exists as an atropoenantiomer with the M-configuration. Though configurationally stable at room temperature, M(-)-marinopyrrole A can be racemized at elevated temperatures to yield the non-natural P-(+)-atropo-enantiomer. The marinopyrroles possess potent antibiotic activities against methicillin-resistant Staphylococcus aureus.
引用
收藏
页码:629 / 631
页数:3
相关论文
共 18 条
[11]  
SANTO RD, 1994, FARMACO, V49, P229
[12]   Statistical approaches for estimating actinobacterial diverity in marine sediments [J].
Stach, JEM ;
Maldonado, LA ;
Masson, DG ;
Ward, AC ;
Goodfellow, M ;
Bull, AT .
APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 2003, 69 (10) :6189-6200
[13]   PSEUDOMONAS PIGMENTS .3. DERIVATIVES OF PYOLUTEORIN [J].
TAKEDA, R .
BULLETIN OF THE AGRICULTURAL CHEMICAL SOCIETY OF JAPAN, 1959, 23 (02) :126-130
[14]   STRUCTURE OF A NEW ANTIBIOTIC, PYOLUTEORIN [J].
TAKEDA, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (17) :4749-4750
[15]   SYNTHESEN N-SUBSTITUIERTER PYRROLE [J].
TREIBS, A ;
HITZLER, O .
CHEMISCHE BERICHTE-RECUEIL, 1957, 90 (05) :787-788
[16]   Antibacterial natural products in medicinal chemistry - Exodus or revival? [J].
von Nussbaum, Franz ;
Brands, Michael ;
Hinzen, Berthold ;
Weigand, Stefan ;
Haebich, Dieter .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (31) :5072-5129
[17]  
Wu J, 2002, ANGEW CHEM INT EDIT, V41, P1740, DOI 10.1002/1521-3773(20020517)41:10<1740::AID-ANIE1740>3.0.CO
[18]  
2-7