Herbacic acid, a simple prototype of 5,5,5-trichloroleucine metabolites from the sponge Dysidea herbacea

被引:33
作者
MacMillan, JB [1 ]
Molinski, TF [1 ]
机构
[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA
来源
JOURNAL OF NATURAL PRODUCTS | 2000年 / 63卷 / 01期
关键词
D O I
10.1021/np990468j
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Dysidea herbacea, collected at Harrier Reef on the Great Barrier Reef, contains the novel metabolite herbacic acid as the major trichloroleucine metabolite. Herbacic acid appears to be an early product of direct free-radical chlorination of leucine and is a prototype for further transformation of the free carboxylic acid group and generation of complex trichloromethyl metabolites, including natural products of the dysidenin family.
引用
收藏
页码:155 / 157
页数:3
相关论文
共 25 条
[1]   REVISED ABSOLUTE-CONFIGURATION OF DYSIDENIN AND ISODYSIDENIN [J].
BISKUPIAK, JE ;
IRELAND, CM .
TETRAHEDRON LETTERS, 1984, 25 (28) :2935-2936
[2]   DYSIDAMIDE, A NOVEL METABOLITE FROM A RED-SEA SPONGE DYSIDEA-HERBACEA [J].
CARMELY, S ;
GEBREYESUS, T ;
KASHMAN, Y ;
SKELTON, BW ;
WHITE, AH ;
YOSIEF, T .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1990, 43 (11) :1881-1888
[3]  
CHARLES C, 1978, TETRAHEDRON LETT, P1519
[4]   NOVEL SPONGE DERIVED AMINO-ACIDS .17. A NOVEL CHLORINATED KETIDE AMINO-ACID, HERBAMIDE-A, FROM THE MARINE SPONGE DYSIDEA-HERBACEA [J].
CLARK, WD ;
CREWS, P .
TETRAHEDRON LETTERS, 1995, 36 (08) :1185-1188
[5]  
DUMDEI EJ, 1999, AUST J CHEM, V50, P1139
[6]   NEW POLYCHLORINATED METABOLITES FROM A BARRIER-REEF COLLECTION OF THE SPONGE DYSIDEA-HERBACEA [J].
ERICKSON, KL ;
WELLS, RJ .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1982, 35 (01) :31-38
[7]   Cellular origin of chlorinated diketopiperazines in the dictyoceratid sponge Dysidea herbacea (Keller) [J].
Flowers, AE ;
Garson, MJ ;
Webb, RI ;
Dumdei, EJ ;
Charan, RD .
CELL AND TISSUE RESEARCH, 1998, 292 (03) :597-607
[8]   New diketopiperazines from the sponge Dysidea chlorea [J].
Fu, X ;
Ferreira, MLG ;
Schmitz, FJ ;
Kelly-Borges, M .
JOURNAL OF NATURAL PRODUCTS, 1998, 61 (10) :1226-1231
[9]  
GARSON MJ, 1994, SPONGES SPACE TIME B, P437
[10]  
Hartung J, 1999, ANGEW CHEM INT EDIT, V38, P1209, DOI 10.1002/(SICI)1521-3773(19990503)38:9<1209::AID-ANIE1209>3.0.CO