Moromycins A and B, isolation and structure elucidation of C-glycosylangucycline-type antibiotics from Streptomyces sp KY002

被引:31
作者
Abdelfattah, Mohamed S. [1 ]
Kharel, Madan Kumar [1 ]
Hitron, John Andrew [1 ]
Baig, Irfan [1 ]
Rohr, Juergen [1 ]
机构
[1] Univ Kentucky, Coll Pharm, Div Pharmaceut Sci, Lexington, KY 40536 USA
来源
JOURNAL OF NATURAL PRODUCTS | 2008年 / 71卷 / 09期
基金
美国国家卫生研究院;
关键词
D O I
10.1021/np800281f
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Two new anticancer antibiotics of the angucycline class, moromycins A and B (1, 2), along with the known microbial metabolites saquayamycin B (3) and fridamycin D (4) were isolated from the ethyl acetate extract of a culture broth of the terrestrial Streptomzyces sp. KY002. The structures consist of a tetrangomycin core and various C- and O-glycosidically linked deoxysugars. The chemical structures of the new secondary metabolites were elucidated by 1D and 2D NMR and by mass spectrometry. Moromycin B (2) showed significant cytotoxicity against H-460 human lung cancer and MCF-7 human breast cancer cells.
引用
收藏
页码:1569 / 1573
页数:5
相关论文
共 40 条
[1]   Seitomycin:: Isolation, structure elucidation and biological activity of a new angucycline antibiotic from a terrestrial streptomycete [J].
Abdelfattah, M ;
Maskey, RP ;
Asolkar, RN ;
Grün-Wollny, I ;
Laatsch, H .
JOURNAL OF ANTIBIOTICS, 2003, 56 (06) :539-542
[2]  
[Anonymous], 2000, Practical Streptomyces genetics, DOI DOI 10.1111/J.1365-2427.2007.01876.X
[3]   On the acceptor substrate of C-glycosyl-transferase UrdGT2:: Three prejadomycin C-glycosides from an engineered mutant of Streptomyces globisporus 1912 ΔlndE(urdGT2) [J].
Baig, Irfan ;
Kharel, Madan ;
Kobylyanskyy, Anton ;
Zhu, Lili ;
Rebets, Yuriy ;
Ostash, Bohdan ;
Luzhetskyy, Andriy ;
Bechthold, Andreas ;
Fedorenko, Victor A. ;
Rohr, Juergen .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (46) :7842-7846
[4]   Interspecies physiological variation as a tool for cross-species assessments of global warming-induced endangerment: validation of an intrinsic determinant of macroecological and phylogeographic structure [J].
Bernardo, Joseph ;
Ossola, Ryan J. ;
Spotila, James ;
Crandall, Keith A. .
BIOLOGY LETTERS, 2007, 3 (06) :695-698
[5]   Physiological constraints on organismal response to global warming: mechanistic insights from clinally varying populations and implications for assessing endangerment [J].
Bernardo, Joseph ;
Spotila, James R. .
BIOLOGY LETTERS, 2006, 2 (01) :135-139
[6]   Frigocyclinone, a novel angucyclinone antibiotic produced by a Streptomyces griseus strain from Antarctica [J].
Bruntner, C ;
Binder, T ;
Pathom-aree, W ;
Goodfellow, M ;
Bull, AT ;
Potterat, O ;
Puder, C ;
Hörer, S ;
Schmid, A ;
Bolek, W ;
Wagner, K ;
Mihm, G ;
Fiedler, HP .
JOURNAL OF ANTIBIOTICS, 2005, 58 (05) :346-349
[7]   A classification of nucleotide-diphospho-sugar glycosyltransferases based on amino acid sequence similarities (vol 326, pg 929, 1997) [J].
Campbell, JA ;
Davies, GJ ;
Bulone, V ;
Henrissat, B .
BIOCHEMICAL JOURNAL, 1998, 329 :719-719
[8]   A classification of nucleotide-diphospho-sugar glycosyltransferases based on amino acid sequence similarities [J].
Campbell, JA ;
Davies, GJ ;
Bulone, V ;
Henrissat, B .
BIOCHEMICAL JOURNAL, 1997, 326 :929-939
[9]  
Dann M, 1965, Antimicrob Agents Chemother (Bethesda), V5, P832
[10]   DERIVATIVES OF SAQUAYAMYCIN-A AND SAQUAYAMYCIN-B REGIOSELECTIVE AND DIASTEREOSELECTIVE ADDITION OF ALCOHOLS TO THE L-ACULOSE MOIETY [J].
HENKEL, T ;
ZEECK, A .
JOURNAL OF ANTIBIOTICS, 1990, 43 (07) :830-837