Cyanogenic glycosides: A case study for evolution and application of cytochromes P450

被引：107

作者：

Bak S. ^{[1
]}

Paquette S.M. ^{[2
]}

Morant M. ^{[1
]}

Morant A.V. ^{[1
]}

Saito S. ^{[1
]}

Bjarnholt N. ^{[1
]}

Zagrobelny M. ^{[1
]}

Jørgensen K. ^{[1
]}

Osmani S. ^{[1
]}

Simonsen H.T. ^{[1
]}

Pérez R.S. ^{[1
]}

Van Heeswijck T.B. ^{[1
]}

Jørgensen B. ^{[3
]}

Møller B.L. ^{[1
]}

机构：

[1] Department of Plant Biology, Center for Molecular Plant Physiology (PlaCe), Royal Veterinary and Agricultural University, 1871 Frederiksberg Copenhagen

[2] Department of Biological Structure, University of Washington, HSB G-514/Box 357420, Seattle

[3] Research Group Cell Wall Biology and Molecular Virology, Department of Genetics and Biotechnology, Danish Institute of Agricultural Sciences, 1871 Frederiksberg Copenhagen

来源：

Phytochemistry Reviews | 2006年 / 5卷 / 2-3期

关键词：

CYP79; Metabolic engineering; Metabolons; Plant-insect interactions; Systems biology;

D O I：

10.1007/s11101-006-9033-1

中图分类号：

学科分类号：

摘要：

Cyanogenic glycosides are ancient biomolecules found in more than 2,650 higher plant species as well as in a few arthropod species. Cyanogenic glycosides are amino acid-derived β-glycosides of α-hydroxynitriles. In analogy to cyanogenic plants, cyanogenic arthropods may use cyanogenic glycosides as defence compounds. Many of these arthropod species have been shown to de novo synthesize cyanogenic glycosides by biochemical pathways that involve identical intermediates to those known from plants, while the ability to sequester cyanogenic glycosides appears to be restricted to Lepidopteran species. In plants, two atypical multifunctional cytochromes P450 and a soluble family 1 glycosyltransferase form a metabolon to facilitate channelling of the otherwise toxic and reactive intermediates to the end product in the pathway, the cyanogenic glycoside. The glucosinolate pathway present in Brassicales and the pathway for cyanoalk(en)yl glucoside synthesis such as rhodiocyanosides A and D in Lotus japonicus exemplify how cytochromes P450 in the course of evolution may be recruited for novel pathways. The use of metabolic engineering using cytochromes P450 involved in biosynthesis of cyanogenic glycosides allows for the generation of acyanogenic cassava plants or cyanogenic Arabidopsis thaliana plants as well as L. japonicus and A. thaliana plants with altered cyanogenic, cyanoalkenyl or glucosinolate profiles. © 2006 Springer Science+Business Media B.V.

引用

页码：309 / 329

页数：20

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