Nakiterpiosin and nakiterpiosinone, novel cytotoxic C-nor-D-homosteroids from the Okinawan sponge Terpios hoshinota

被引:55
作者
Teruya, T [1 ]
Nakagawa, S [1 ]
Koyama, T [1 ]
Arimoto, H [1 ]
Kita, M [1 ]
Uemura, D [1 ]
机构
[1] Nagoya Univ, Grad Sch Sci, Dept Chem, Nagoya, Aichi 4648602, Japan
关键词
C-nor-D-homosteroid; the sponge Terpios hoshinota; nakiterpiosin; nakiterpiosinone; cytotoxicity;
D O I
10.1016/j.tet.2003.08.083
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two new cytotoxic compounds, nakiterpiosin (1) and nakiterpiosinone (2), were isolated from the Okinawan sponge Terpios hoshinota. Their structures were determined by spectroscopic analysis. The absolute stereostructure of 1 was also determined by a modified Mosher's method. Nakiterpiosin (1) and nakiterpiosinone (2) showed potent cytotoxicity against mouse lymphocytic leukemia cell (P388). (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6989 / 6993
页数:5
相关论文
共 16 条
[1]  
Cragg GM, 1999, CANCER INVEST, V17, P153
[2]   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
[3]   HALOGENATED ALICYCLIC MONOTERPENES FROM RED ALGAE PLOCAMIUM [J].
CREWS, P ;
WISEMAN, EK ;
MONTANA, P .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (01) :116-120
[4]   CATASTROPHES, PHASE-SHIFTS, AND LARGE-SCALE DEGRADATION OF A CARIBBEAN CORAL-REEF [J].
HUGHES, TP .
SCIENCE, 1994, 265 (5178) :1547-1551
[5]   ADRENOCORTICOSTEROIDS - CHEMISTRY, SYNTHESIS AND DISTURBANCES IN DISEASE [J].
JAMES, VHT ;
FEW, JD .
CLINICS IN ENDOCRINOLOGY AND METABOLISM, 1985, 14 (04) :867-892
[6]  
Long BH, 1998, CANCER RES, V58, P1111
[7]   TREATMENT OF CUSHINGS-DISEASE BY O,P'DDD - SURVEY OF 62 CASES [J].
LUTON, JP ;
MAHOUDEAU, JA ;
BOUCHARD, P ;
THIEBLOT, P ;
HAUTECOUVERTURE, M ;
SIMON, D ;
LAUDAT, MH ;
TOUITOU, Y ;
BRICAIRE, H .
NEW ENGLAND JOURNAL OF MEDICINE, 1979, 300 (09) :459-464
[8]   THE MEDICAL-TREATMENT OF CUSHINGS-SYNDROME [J].
MILLER, JW ;
CRAPO, L .
ENDOCRINE REVIEWS, 1993, 14 (04) :443-458
[9]   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
[10]   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