Tetrocarcins N and O, glycosidic spirotetronates from a marine-derived Micromonospora sp identified by PCR-based screening

被引:19
作者
Tan, Yi [1 ,2 ]
Hu, Yuanyuan [1 ,2 ]
Wang, Qiang [1 ,2 ]
Zhou, Hongxia [1 ,2 ]
Wang, Yiguang [1 ,2 ]
Gan, Maoluo [1 ,2 ,3 ]
机构
[1] Chinese Acad Med Sci, Inst Med Biotechnol, Beijing 100050, Peoples R China
[2] Peking Union Med Coll, Beijing 100050, Peoples R China
[3] Chinese Acad Med Sci, Inst Mat Med, State Key Lab Bioact Substance & Funct Nat Med, Beijing 100050, Peoples R China
基金
中国国家自然科学基金;
关键词
ANTI-TUMOR ANTIBIOTICS; FERMENTATION; APOPTOSIS;
D O I
10.1039/c6ra17026a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Two new glycosidic spirotetronate antibiotics, tetrocarcins N (1) and O (2), were isolated and identified from the marine-derived Micromonospora sp. 5-297 using a PCR-based genetic screening method targeting the dTDP-glucose-4,6-dehydratase gene. Their structures were determined by extensive IR, NMR, and MS spectroscopic analyses. Tetrocarcin O (2) is a derivative of 1 that lacks the terminal L-amicetose moiety at C-9. Compound 1 and 2 exhibited antibacterial activity against Bacillus subtilis with MIC values of 2 and 64 mu g mL(-1), respectivly. It seems that the sugar moieties at C-9 and the formyl group at C-32 play important roles in the antibacterial activity of the tetrocarcins.
引用
收藏
页码:91773 / 91778
页数:6
相关论文
共 21 条
[1]   Tetrocarcin-A-induced ER stress mediates apoptosis in B-CLL cells via a Bcl-2-independent pathway [J].
Anether, G ;
Tinhofer, I ;
Senfter, M ;
Greil, R .
BLOOD, 2003, 101 (11) :4561-4568
[2]  
[Anonymous], STEREOCHEMISTRY FUND
[3]  
[Anonymous], 2012, METH DIL ANT SUSC TE
[4]   Distribution of dTDP-glucose-4,6-dehydratase gene and diversity of potential glycosylated natural products in marine sediment-derived bacteria [J].
Chen, Feifei ;
Lin, Ling ;
Wang, Lu ;
Tan, Yi ;
Zhou, Hongxia ;
Wang, Yiguang ;
Wang, Yong ;
He, Weiqing .
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 2011, 90 (04) :1347-1359
[5]   Identification and functional analysis of dTDP-Glucose-4,6-dehydratase gene and its linked gene cluster in an aminoglycoside antibiotics producer of Streptomyces tenebrarius H6 [J].
Du, Y ;
Li, TB ;
Wang, YGG ;
Xia, HZ .
CURRENT MICROBIOLOGY, 2004, 49 (02) :99-107
[6]   A comprehensive review of glycosylated bacterial natural products [J].
Elshahawi, Sherif I. ;
Shaaban, Khaled A. ;
Kharel, Madan K. ;
Thorson, Jon S. .
CHEMICAL SOCIETY REVIEWS, 2015, 44 (21) :7591-7697
[7]   Saccharothrixones A-D, Tetracenomycin-Type Polyketides from the Marine-Derived Actinomycete Saccharothrix sp 10-10 [J].
Gan, Maoluo ;
Liu, Bin ;
Tan, Yi ;
Wang, Qiang ;
Zhou, Hongxia ;
He, Hongwei ;
Ping, Yuhui ;
Yang, Zhaoyong ;
Wang, Yiguang ;
Xiao, Chunling .
JOURNAL OF NATURAL PRODUCTS, 2015, 78 (09) :2260-2265
[8]   THE STRUCTURE OF TETRONOLIDE, THE AGLYCONE OF ANTI-TUMOR ANTIBIOTIC TETROCARCIN [J].
HIRAYAMA, N ;
KASAI, M ;
SHIRAHATA, K ;
OHASHI, Y ;
SASADA, Y .
TETRAHEDRON LETTERS, 1980, 21 (26) :2559-2560
[9]   Arisostatins A and B, new members of tetrocarcin class of antibiotics from Micromonospora sp TP-A0316 -: II.: Structure determination [J].
Igarashi, Y ;
Takagi, K ;
Kan, Y ;
Fujii, K ;
Harada, K ;
Furumai, T ;
Oki, T .
JOURNAL OF ANTIBIOTICS, 2000, 53 (03) :233-240
[10]   Sweet antibiotics - the role of glycosidic residues in antibiotic and antitumor activity and their randomization [J].
Kren, Vladimir ;
Rezanka, Tomas .
FEMS MICROBIOLOGY REVIEWS, 2008, 32 (05) :858-889