Nakiterpiosin, a novel cytotoxic C-nor-D-homosteroid from the Okinawan sponge Terpios hoshinota

被引:34
作者
Teruya, T [1 ]
Nakagawa, S [1 ]
Koyama, T [1 ]
Suenaga, K [1 ]
Kita, M [1 ]
Uemura, D [1 ]
机构
[1] Nagoya Univ, Dept Chem, Grad Sch Sci, Nagoya, Aichi 4648602, Japan
关键词
D O I
10.1016/S0040-4039(03)01267-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel cytotoxic compound, nakiterpiosin (1), was isolated from the Okinawan sponge Terpios hoshinota. Its structure was determined by spectroscopic analysis. The absolute stereostructure of 1 was also determined by a modified Mosher's method. Nakiterpiosin showed potent cytotoxicity against P388 cells. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5171 / 5173
页数:3
相关论文
共 9 条
[1]   HALOGEN REGIOCHEMISTRY AND SUBSTITUENT STEREOCHEMISTRY DETERMINATION IN MARINE MONOTERPENES BY C-13 NMR [J].
CREWS, P ;
NAYLOR, S ;
HANKE, FJ ;
HOGUE, ER ;
KHO, E ;
BRASLAU, R .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (08) :1371-1377
[2]   HALOGENATED ALICYCLIC MONOTERPENES FROM RED ALGAE PLOCAMIUM [J].
CREWS, P ;
WISEMAN, EK ;
MONTANA, P .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (01) :116-120
[3]   CATASTROPHES, PHASE-SHIFTS, AND LARGE-SCALE DEGRADATION OF A CARIBBEAN CORAL-REEF [J].
HUGHES, TP .
SCIENCE, 1994, 265 (5178) :1547-1551
[4]   NAKIENONES A-C AND NAKITRIOL, NEW CYTOTOXIC CYCLIC C-11 METABOLITES FROM AN OKINAWAN CYANOBACTERIAL (SYNECHOCYSTIS SP) OVERGROWTH OF CORAL [J].
NAGLE, DG ;
GERWICK, WH .
TETRAHEDRON LETTERS, 1995, 36 (06) :849-852
[5]   HIGH-FIELD FT NMR APPLICATION OF MOSHER METHOD - THE ABSOLUTE-CONFIGURATIONS OF MARINE TERPENOIDS [J].
OHTANI, I ;
KUSUMI, T ;
KASHMAN, Y ;
KAKISAWA, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4092-4096
[6]   2 STEROIDAL ALKALOIDS FROM A MARINE SPONGE, PLAKINA SP [J].
ROSSER, RM ;
FAULKNER, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (26) :5157-5160
[7]  
*ROY SOC CHEM, 1971, VER ALK REG REV ALK, V1
[8]   Terpiodiene:: A novel tricyclic alcohol from the Okinawan sponge Terpios hoshinota [J].
Teruya, T ;
Nakagawa, S ;
Koyama, T ;
Suenaga, K ;
Uemura, D .
CHEMISTRY LETTERS, 2002, (01) :38-39
[9]   Arachidonic acid and α-linolenic acid, feeding attractants for the crown-of-thorns sea star Acanthaster planci, from the sea urchin Toxopneustes pileolus [J].
Teruya, T ;
Suenaga, K ;
Koyama, T ;
Nakano, Y ;
Uemura, D .
JOURNAL OF EXPERIMENTAL MARINE BIOLOGY AND ECOLOGY, 2001, 266 (02) :123-134