Lagunapyrones A-C: Cytotoxic acetogenins of a new skeletal class from a marine sediment bacterium

被引:31
作者
Lindel, T [1 ]
Jensen, PR [1 ]
Fenical, W [1 ]
机构
[1] UNIV CALIF SAN DIEGO,SCRIPPS INST OCEANOG,LA JOLLA,CA 92093
基金
美国国家卫生研究院;
关键词
D O I
10.1016/0040-4039(96)00014-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The structures of the lagunapyrones A-C (1-3), novel, cytotoxic alpha-pyrones, produced in fermentation by a marine bacterium, have been assigned on the basis of comprehensive spectroscopic analyses. Transformation of lagunapyrone B (2) to its [1', 3'-C-13(2)]-labelled acetonide allowed the relative stereochemistry of the flexible 1,3-diol moiety to be determined.
引用
收藏
页码:1327 / 1330
页数:4
相关论文
共 11 条
[1]   H-1 AND C-13 ASSIGNMENTS FROM SENSITIVITY-ENHANCED DETECTION OF HETERONUCLEAR MULTIPLE-BOND CONNECTIVITY BY 2D MULTIPLE QUANTUM NMR [J].
BAX, A ;
SUMMERS, MF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) :2093-2094
[2]   CHEMICAL STUDIES OF MARINE-BACTERIA - DEVELOPING A NEW RESOURCE [J].
FENICAL, W .
CHEMICAL REVIEWS, 1993, 93 (05) :1673-1683
[3]  
FLEMING I, 1992, J CHEM SOC PERKIN TR, V1, P3267
[4]   LEPTOMYCIN-A AND LEPTOMYCIN-B NEW ANTI-FUNGAL ANTIBIOTICS .2. STRUCTURE ELUCIDATION [J].
HAMAMOTO, T ;
SETO, H ;
BEPPU, T .
JOURNAL OF ANTIBIOTICS, 1983, 36 (06) :646-650
[5]   A NEW ANTIBIOTIC, STRUCTURALLY RELATED TO LEPTOMYCIN-A, FLATTENS THE MORPHOLOGY OF V-RAS(TS)NRK CELLS [J].
HOSOKAWA, N ;
IINUMA, H ;
NAGANAWA, H ;
HAMADA, M ;
TAKEUCHI, T ;
ITOH, T ;
HORI, M .
JOURNAL OF ANTIBIOTICS, 1993, 46 (04) :676-678
[6]   STEREOCHEMISTRY OF ALTERNATING POLYOL CHAINS - C-13 NMR ANALYSIS OF 1,3-DIOL ACETONIDES [J].
RYCHNOVSKY, SD ;
SKALITZKY, DJ .
TETRAHEDRON LETTERS, 1990, 31 (07) :945-948
[7]   ANALYSIS OF 2 C-13 NMR CORRELATIONS FOR DETERMINING THE STEREOCHEMISTRY OF 1,3-DIOL ACETONIDES [J].
RYCHNOVSKY, SD ;
ROGERS, B ;
YANG, G .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (13) :3511-3515
[8]  
SUMMERS MF, 1986, J AM CHEM SOC, V108, P2093
[9]   TRIALKYLSILYL TRIFLATES .6. FACILE PROCEDURE FOR ACETALIZATION UNDER APROTIC CONDITIONS [J].
TSUNODA, T ;
SUZUKI, M ;
NOYORI, R .
TETRAHEDRON LETTERS, 1980, 21 (14) :1357-1358
[10]   EFFECTS OF LEPTOMYCIN-B ON THE CELL-CYCLE OF FIBROBLASTS AND FISSION YEAST-CELLS [J].
YOSHIDA, M ;
NISHIKAWA, M ;
NISHI, K ;
ABE, K ;
HORINOUCHI, S ;
BEPPU, T .
EXPERIMENTAL CELL RESEARCH, 1990, 187 (01) :150-156