Genoketides A1 and A2, new octaketides and biosynthetic intermediates of chrysophanol produced by Streptomyces sp AK 671

被引:9
作者
Fiedler, Hans-Peter [1 ]
Dieter, Anke [1 ]
Guider, Tobias A. M. [3 ]
Kajahn, Inga [3 ]
Hamm, Andreas [3 ]
Brown, Ros [2 ]
Jones, Amanda L. [2 ]
Goodfellow, Michael [2 ]
Mueller, Werner E. G. [4 ]
Bringmann, Gerhard [3 ]
机构
[1] Univ Tubingen, Inst Mikrobiol, D-72076 Tubingen, Germany
[2] Univ Newcastle, Sch Biol, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England
[3] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
[4] Johannes Gutenberg Univ Mainz, Inst Physiol Chem, Angew Mol Biol Abt, D-55099 Mainz, Germany
关键词
Streptomyces; octaketides; chrysophanol; fermentation; structure elucidation; antitumor activity;
D O I
10.1038/ja.2008.63
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
The new aromatic polyketides genoketide A1, genoketide A2 and prechrysophanol glucuronide are biosynthetic intermediates of the octaketide chrysophanol. They were isolated from the alkaliphilic strain Streptomyces sp. AK 671 together with the new metabolite chrysophanol glucuronide. The structures of the compounds were elucidated by mass spectrometry and NMR methods. Genoketide A2 exhibited a slight and prechrysophanol glucuronide a more pronounced inhibition of the proliferation of L5178y lymphoma cells.
引用
收藏
页码:464 / 473
页数:10
相关论文
共 21 条
[1]  
[Anonymous], 1993, NAT PROD LETT
[2]   Pyrocoll, an antibiotic, antiparasitic and antitumor compound produced by a novel alkaliphilic Streptomyces strain [J].
Dieter, A ;
Fiedler, HP ;
Goodfellow, M ;
Müller, WEG ;
Brun, R ;
Beil, W ;
Bringmann, G .
JOURNAL OF ANTIBIOTICS, 2003, 56 (07) :639-646
[3]   Bhimamycin A∼E and bhimanone:: Isolation, structure elucidation and biological activity of novel quinone antibiotics from a terrestrial streptomycete [J].
Fotso, S ;
Maskey, RP ;
Grün-Wollny, I ;
Schulz, KP ;
Munk, M ;
Laatsch, H .
JOURNAL OF ANTIBIOTICS, 2003, 56 (11) :931-941
[4]  
FRANCK B, 1981, LIEBIGS ANN CHEM, P2106
[5]   BIOGENETIC-TYPE SYNTHESES OF EMODIN AND CHRYSOPHANOL [J].
HARRIS, TM ;
WEBB, AD ;
HARRIS, CM ;
WITTEK, PJ ;
MURRAY, TP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (19) :6065-6067
[6]   Lactonamycin Z, an antibiotic and antitumor compound produced by Streptomyces sanglieri strain AK 623 [J].
Höltzel, A ;
Dieter, A ;
Schmid, DG ;
Brown, R ;
Goodfellow, M ;
Beil, W ;
Jung, G ;
Fiedler, HP .
JOURNAL OF ANTIBIOTICS, 2003, 56 (12) :1058-1061
[7]   Genetic contributions to understanding polyketide synthases [J].
Hopwood, DA .
CHEMICAL REVIEWS, 1997, 97 (07) :2465-2497
[8]   Heterologous biosynthesis of truncated hexaketides derived from the actinorhodin polyketide synthase [J].
Kalaitzis, JA ;
Moore, BS .
JOURNAL OF NATURAL PRODUCTS, 2004, 67 (08) :1419-1422
[9]  
KRUPA J, 1989, LIEBIGS ANN CHEM, P699
[10]  
LESSMANN K, 1989, Z NATURFORSCH B, V44, P353