Cardenolide biosynthesis in foxglove

被引:57
作者
Kreis, W [1 ]
Hensel, A [1 ]
Stuhlemmer, U [1 ]
机构
[1] Univ Erlangen Nurnberg, Inst Bot & Pharmazeut Biol, D-91058 Erlangen, Germany
关键词
biosynthesis; cardenolides; cardiac glycosides; glycosidase; glycosyl transferase; enzymes; feeding experiments; Digitalis; oxido-reductases; secondary metabolism; Scrophulariaceae; tracer studies;
D O I
10.1055/s-2006-957500
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
The article reviews the state of knowledge on the biosynthesis of cardenolides in the genus Digitalis. It summarizes studies with labelled and unlabelled precursors leading to the formulation of the putative cardenolide pathway. Alternative pathways of cardenolide biosynthesis are discussed as well. Special emphasis is laid on enzymes involved in either pregnane metabolism or the modification of cardenolides. About 20 enzymes which are probably involved in cardenolide formation have been described "downstream" of cholesterol, including various reductases, oxido-reductases, glycosyl transferases and glycosidases as well as acyl transferases, acyl esterases and P450 enzymes. Evidence is accumulating that cardenolides are not assembled on one straight conveyor belt but instead are formed via a complex multidimensional metabolic grid. For example "fucose-type" cardenolides and "digitoxose-type" cardenolides seem to form via different biosynthetic branches and the "norcholanic acid pathway" identified recently seems to be operative only in the formation of fucose-type cardenolides.
引用
收藏
页码:491 / 499
页数:9
相关论文
共 80 条
[1]   BIOSYNTHESIS OF CARDENOLIDES IN DIGITALIS-LANATA [J].
ABERHART, DJ ;
LLOYDJON.JG ;
CASPI, E .
PHYTOCHEMISTRY, 1973, 12 (05) :1065-1071
[2]   MECHANISM OF 14-BETA-HYDROXYLATION IN BIOSYNTHESIS OF CARDENOLIDES - ROLE OF 14-BETA-CHOLEST-5-EN-3BETA-OL [J].
ANASTASIA, M ;
RONCHETTI, F .
PHYTOCHEMISTRY, 1977, 16 (07) :1082-1083
[3]   BIOSYNTHESIS OF CARDIAC-GLYCOSIDES - NUCLEOTIDE-BOUND 2,6-DIDEOXY-3-O-METHYLHEXOSES IN LEAF EXTRACTS OF NERIUM OLEANDER [J].
BAUER, P ;
KOPP, B ;
FRANZ, G .
PLANTA MEDICA, 1984, 50 (01) :12-14
[4]   PROGESTERONE METABOLISM IN DIGITALIS LANATA [J].
BENNETT, RD ;
SAUER, HH ;
HEFTMANN, E .
PHYTOCHEMISTRY, 1968, 7 (01) :41-&
[5]   A FUNCTION OF SITOSTEROL [J].
BENNETT, RD ;
HEFTMANN, E ;
WINTER, BJ .
PHYTOCHEMISTRY, 1969, 8 (12) :2325-&
[6]  
BOTTIGHEIMER U, 1995, 43 ANN C MED PLANT R
[7]  
Buhl W., 1984, THESIS U MARBURG
[8]   BIOSYNTHESIS OF PLANT STEROLS .4. AN INVESTIGATION OF A POSSIBLE MODE OF 14BETA-HYDROXYLATION IN DIGITOXIGENIN [J].
CASPI, E ;
LEWIS, DO .
PHYTOCHEMISTRY, 1968, 7 (05) :683-&
[9]   BIOSYNTHESIS OF PLANT STEROLS . CONVERSION OF CHOLESTEROL TO PREGNENOLONE IN DIGITALIS PURPUREA [J].
CASPI, E ;
LEWIS, DO ;
PIATAK, DM ;
THIMANN, KV ;
WINTER, A .
EXPERIENTIA, 1966, 22 (08) :506-&
[10]   UPTAKE, TRANSPORT AND STORAGE OF CARDENOLIDES IN FOXGLOVE - CARDENOLIDE SINKS AND OCCURRENCE OF CARDENOLIDES IN THE SIEVE TUBES OF DIGITALIS-LANATA [J].
CHRISTMANN, J ;
KREIS, W ;
REINHARD, E .
BOTANICA ACTA, 1993, 106 (05) :419-427