Saccharothriolides A-C, novel phenyl-substituted 10-membered macrolides isolated from a rare actinomycete Saccharothrix sp.

被引:21
作者
Lu, Shan [1 ]
Nishimura, Shinichi [1 ]
Hirai, Go [2 ]
Ito, Masashi [3 ]
Kawahara, Teppei [4 ]
Izumikawa, Miho [4 ]
Sodeoka, Mikiko [2 ]
Shin-Ya, Kazuo [5 ]
Tsuchida, Toshio [3 ]
Kakeya, Hideaki [1 ]
机构
[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Dept Syst Chemotherapy & Mol Sci, Div Bioinformat & Chem Genom,Sakyo Ku, Kyoto 6068501, Japan
[2] RIKEN, Synthet Organ Chem Lab, Wako, Saitama 3510198, Japan
[3] MicroBioPharm Japan Co Ltd MBJ, Div Res & Dev, Iwata, Shizuoka 4380078, Japan
[4] JBIC, Koto Ku, Tokyo 1350064, Japan
[5] Natl Inst Adv Ind Sci & Technol, Koto Ku, Tokyo 1350064, Japan
基金
日本学术振兴会;
关键词
BIOSYNTHETIC GENE-CLUSTER; UNIVERSAL NMR DATABASE; STEREOCHEMICAL ASSIGNMENT; ACYCLIC COMPOUNDS; ANTIBIOTICS; CREATION;
D O I
10.1039/c5cc01953b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Three new 10-membered macrolides, saccharothriolides A-C (1-3), were discovered from a rare actinomycete Saccharothrix sp. A1506. All of the sp(3) carbons in the 10-membered ring had chirality, which was determined by extensive spectroscopic analysis and TDDFT-calculation of ECD spectra. Saccharothriolide B (2) exhibited cytotoxicity against human tumor cell lines HeLa and HT1080.
引用
收藏
页码:8074 / 8077
页数:4
相关论文
共 18 条
[1]   Biosynthesis of the ansamycin antibiotic rifamycin: deductions from the molecular analysis of the rif biosynthetic gene cluster of Amycolatopsis mediterranei S699 [J].
August, PR ;
Tang, L ;
Yoon, YJ ;
Ning, S ;
Muller, R ;
Yu, TW ;
Taylor, M ;
Hoffmann, D ;
Kim, CG ;
Zhang, XH ;
Hutchinson, CR ;
Floss, HG .
CHEMISTRY & BIOLOGY, 1998, 5 (02) :69-79
[2]   Bioactive microbial metabolites -: A personal view [J].
Bérdy, J .
JOURNAL OF ANTIBIOTICS, 2005, 58 (01) :1-26
[3]   Advances in the Universal NMR Database: Toward the Determination of the Relative Configurations of Large Polypropionates [J].
Fleury, Etienne ;
Lannou, Marie-Isabelle ;
Bistri, Olivia ;
Sautel, Francois ;
Massiot, Georges ;
Pancrazi, Ange ;
Ardisson, Janick .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (29) :4992-5001
[4]   Toward creation of a universal NMR database for the stereochemical assignment of acyclic compounds: The case of two contiguous propionate units [J].
Kobayashi, Y ;
Lee, J ;
Tezuka, K ;
Kishi, Y .
ORGANIC LETTERS, 1999, 1 (13) :2177-2180
[5]   SACCHAROTHRIX - A NEW GENUS OF THE ACTINOMYCETALES RELATED TO NOCARDIOPSIS [J].
LABEDA, DP ;
TESTA, RT ;
LECHEVALIER, MP ;
LECHEVALIER, HA .
INTERNATIONAL JOURNAL OF SYSTEMATIC BACTERIOLOGY, 1984, 34 (04) :426-431
[6]   Toward creation of a universal NMR database for the stereochemical assignment of acyclic compounds: Proof of concept [J].
Lee, J ;
Kobayashi, Y ;
Tezuka, K ;
Kishi, Y .
ORGANIC LETTERS, 1999, 1 (13) :2181-2184
[7]   Characterization of the biosynthetic gene cluster for the antifungal polyketide soraphen A from Sorangium cellulosum So ce26 [J].
Ligon, J ;
Hill, S ;
Beck, J ;
Zirkle, R ;
Molnár, I ;
Zawodny, J ;
Money, S ;
Schupp, T .
GENE, 2002, 285 (1-2) :257-267
[8]   Ammocidin, a new apoptosis inducer in Ras-dependent cells from Saccharothrix sp.: I.: Production, isolation and biological activity [J].
Murakami, R ;
Tomikawa, T ;
Shin-Ya, K ;
Shinozaki, J ;
Kajiura, T ;
Kinoshita, T ;
Miyajima, A ;
Seto, H ;
Hayakawa, Y .
JOURNAL OF ANTIBIOTICS, 2001, 54 (09) :710-713
[9]   Ammocidins B, C and D, new cytotoxic 20-membered macrolides from Saccharothrix sp AJ9571 [J].
Murakami, Ryo ;
Shinozaki, Junko ;
Kajiura, Takayuki ;
Kozone, Ikuko ;
Takagi, Motoki ;
Shin-Ya, Kazuo ;
Seto, Haruo ;
Hayakawa, Yoichi .
JOURNAL OF ANTIBIOTICS, 2009, 62 (03) :123-127
[10]   Sacchathridine A, a Prostaglandin Release Inhibitor from Saccharothrix sp. [J].
Nakae, Koichi ;
Kurata, Ikuko ;
Kojima, Fukiko ;
Igarashi, Masayuki ;
Hatano, Masaki ;
Sawa, Ryuichi ;
Kubota, Yumiko ;
Adachi, Hayamitsu ;
Nomoto, Akio .
JOURNAL OF NATURAL PRODUCTS, 2013, 76 (04) :720-722