New cytotoxic oxygenated fucosterols from the brown alga Turbinaria conoides

被引:67
作者
Sheu, JH [1 ]
Wang, GH [1 ]
Sung, PJ [1 ]
Duh, CY [1 ]
机构
[1] Natl Sun Yat Sen Univ, Dept Marine Resources, Kaohsiung 804, Taiwan
来源
JOURNAL OF NATURAL PRODUCTS | 1999年 / 62卷 / 02期
关键词
D O I
10.1021/np980233s
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Fucosterol (1), 24 xi-hydroperoxy-24-vinylcholesterol (2), 29-hydroperoxystigmasta-5,24(28)-dien-3 beta-ol (3), 24-ethylcholesta-4,24(28)-dien-3-one (4), 24 xi-hydroperoxy-24-ethylcholesta-4,28(29) (5), 24-ethylcholesta-4,24(28)-dien-3,6-dione (6), 24 xi-hydroperoxy-24-ethylcholesta-4,28(29)(7), 6 beta-hydroxy-24-ethylcholesta-4, 24(28)-dien-3-one (8), and 24 xi-hydroperoxy-6 beta-hydroxy-24-ethylcholesta-4,-28(29)-dien-3-one (9) were isolated from the marine brown alga Turbinaria conoides. The structures of these compounds were established by spectral analysis. Isolated for the first time from a natural source, the oxygenated fucosterols 4-9 exhibit cytotoxicity against various cancer cell lines.
引用
收藏
页码:224 / 227
页数:4
相关论文
共 20 条
[1]   TURBINARIC ACID, A CYTO-TOXIC SECOSQUALENE CARBOXYLIC-ACID FROM THE BROWN ALGA TURBINARIA-ORNATA [J].
ASARI, F ;
KUSUMI, T ;
KAKISAWA, H .
JOURNAL OF NATURAL PRODUCTS, 1989, 52 (05) :1167-1169
[2]   ENE REACTIONS OF ALLYLICALLY STANNYLATED CHOLESTENES - SINGLET OXYGENATION OF 7-ALPHA-TRIPHENYLSTANNYLCHOLEST-5-EN-3-BETA-OL, AND OF 7-ALPHA-TRIPHENYLSTANNYL-CHOLEST-5-ENE-3-ONE AND 7-ALPHA-TRIBUTYLSTANNYL-CHOLEST-5-ENE-3-ONE, AND THE REARRANGEMENT OF 5-ALPHA-TRIBUTYLSTANNYLPEROXY-3-BETA-BENZOYLOXYCHOLEST-6-ENE AND OF 7-ALPHA-TRIBUTYLSTANNYLPEROXY-3-BETA-BENZOYLOXYCHOLEST-5-ENE [J].
DANG, HS ;
DAVIES, AG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (07) :1095-1101
[3]  
FORST DJ, 1968, TETRAHEDRON LETT, P3779
[4]   SIDE CHAIN-HYDROXYLATED STEROLS OF THE RED ALGA ASPARAGOPSIS-ARMATA - SIGNIFICANT PRODUCTS OR ARTIFACTS DUE TO AUTOXIDATION [J].
FRANCISCO, C ;
COMBAUT, G ;
TESTE, J ;
TARCHINI, C ;
DJERASSI, C .
STEROIDS, 1979, 34 (02) :163-169
[5]  
GERAN RI, 1972, CANC CHEMOTHER REP, V3, P1
[6]  
Greca MD, 1990, J NAT PRODUCTS, V53, P1430, DOI DOI 10.1021/np50072a005
[7]   24-HYDROPEROXY-24-VINYL-CHOLESTEROL, A NEW NATURAL HYDROPEROXIDE ISOLATED FROM 2 TUNICATES - PHALLUSIA-MAMILLATA AND CIONA-INTESTINALIS [J].
GUYOT, M ;
DAVOUST, D ;
BELAUD, C .
TETRAHEDRON LETTERS, 1982, 23 (18) :1905-1906
[8]  
GUYOT M, 1983, J CHEM RES S, P188
[10]   SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF CYTOTOXIC 7-HYDROXY STEROLS [J].
HELTZEL, CE ;
GUNATILAKA, BAL ;
KINGSTON, DGI ;
HOFMANN, GA ;
JOHNSON, RK .
JOURNAL OF NATURAL PRODUCTS, 1994, 57 (05) :620-628