Isolation and X-ray crystal structure of racemic xestospongin D from the Singapore marine sponge Niphates sp

被引:18
作者
Pettit, GR
Orr, B
Herald, DL
Doubek, DL
Tackett, L
Schmidt, JM
Boyd, MR
Pettit, RK
Hooper, JNA
机构
[1] ARIZONA STATE UNIV,DEPT CHEM,TEMPE,AZ 85287
[2] NCI,FREDERICK CANC RES & DEV CTR,LAB DRUG DISCOVERY RES & DEV,DTP,DGT,FREDERICK,MD 21702
[3] WESTERN OREGON STATE COLL,DEPT BIOL,MONMOUTH,OR 97361
[4] QUEENSLAND MUSEUM,SESSILE MARINE INVERTEBRATES,BRISBANE,QLD 4101,AUSTRALIA
关键词
D O I
10.1016/0960-894X(96)00225-9
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
(+/-)-Xestospongin D (2) has been isolated from the Singapore marine sponge Niphates sp. The natural product was found to be racemic in contrast to earlier isolations of (+)-xestospongin D from Xestospongia and Haliclona species. The (+/-)-xestospongin D was found to inhibit growth of certain human cancer cell lines comprising the NCI panel (e.g., leukemia subpanel, mean GI(50) 3.62 +/- 2.02 x 10(-6)M; breast subpanel, mean GIS, 4.53 +/- 1.98 x 10(-6)M) as well as the murine P388 lymphocytic leukemia (ED(50) 1.7 mu g/mL) and the bacterium Micrococcus luteus. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:1313 / 1318
页数:6
相关论文
共 24 条
[1]  
ALTOMARE A, SIR92 PROGRAM AUTOMA
[2]   ZUR KONFIGURATIONSBESTIMMUNG VON CHINOLIZIN-DERIVATEN [J].
BOHLMANN, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1957, 69 (20) :641-642
[3]   SOME PRACTICAL CONSIDERATIONS AND APPLICATIONS OF THE NATIONAL-CANCER-INSTITUTE IN-VITRO ANTICANCER DRUG DISCOVERY SCREEN [J].
BOYD, MR ;
PAULI, KD .
DRUG DEVELOPMENT RESEARCH, 1995, 34 (02) :91-109
[4]   STEREOCHEMICAL STUDIES OF NITROGEN BRIDGEHEAD COMPOUNDS BY SPECTRAL MEANS [J].
CRABB, TA ;
NEWTON, RF ;
JACKSON, D .
CHEMICAL REVIEWS, 1971, 71 (01) :109-&
[5]  
DURST UN, 1991, Z KARDIOL, V80, P294
[6]   PHARMACOLOGICALLY ACTIVE SUBSTANCES FROM SOUTHERN PACIFIC MARINE-INVERTEBRATES [J].
ENDO, M ;
NAKAGAWA, M ;
HAMAMOTO, Y ;
ISHIHAMA, M .
PURE AND APPLIED CHEMISTRY, 1986, 58 (03) :387-394
[7]   NIPHATESINES E-H, NEW PYRIDINE ALKALOIDS FROM THE OKINAWAN MARINE SPONGE NIPHATES SP [J].
KOBAYASHI, J ;
ZENG, CM ;
ISHIBASHI, M ;
SHIGEMORI, H ;
SASAKI, T ;
MIKAMI, Y .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (11) :1291-1294
[8]   NIPHATESINES A-D, NEW ANTINEOPLASTIC PYRIDINE ALKALOIDS FROM THE OKINAWAN MARINE SPONGE NIPHATES SP [J].
KOBAYASHI, J ;
MURAYAMA, T ;
KOSUGE, S ;
KANDA, F ;
ISHIBASHI, M ;
KOBAYASHI, H ;
OHIZUMI, Y ;
OHTA, T ;
NOZOE, S ;
SASAKI, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (12) :3301-3303
[9]   ARAGUPETROSINE-A, A NEW VASODILATIVE MACROCYCLIC QUINOLIZIDINE ALKALOID FROM AN OKINAWAN MARINE SPONGE XESTOSPONGIA SP [J].
KOBAYASHI, M ;
KAWAZOE, K ;
KITAGAWA, I .
TETRAHEDRON LETTERS, 1989, 30 (31) :4149-4152
[10]  
KOBAYASHI M, 1989, CHEM PHARM BULL, V37, P1676