title: Convergent evolution in biosynthesis of cyanogenic defence compounds in plants and insects.
abstract: For more than 420 million years, plants, insects and their predators have co-evolved based on a chemical arms race including deployment of refined chemical defence systems by each player. Cyanogenic glucosides are produced by numerous plants and by some specialized insects and serve an important role as defence compounds in these intimate interactions. Burnet moth larvae are able to sequester cyanogenic glucosides from their food plant as well as to carry out de novo biosynthesis. Here we show that three genes (CYP405A2, CYP332A3 and UGT33A1) encode the entire biosynthetic pathway of cyanogenic glucosides in the Burnet moth Zygaena filipendulae. In both plants and insects, convergent evolution has led to two multifunctional P450 enzymes each catalysing unusual reactions and a glucosyl-transferase acting in sequence to catalyse cyanogenic glucoside formation. Thus, plants and insects have independently found a way to package a cyanide time bomb to fend off herbivores and predators.
authors.affiliation: Plant Biochemistry Laboratory, Department of Plant Biology and Biotechnology, University of Copenhagen, 40 Thorvaldsensvej, DK 1871 Frederiksberg C, Copenhagen, Denmark.
authors.forename: Niels Bjerg
authors.initials: NB
authors.lastname: Jensen
authors.forename: Mika
authors.initials: M
authors.lastname: Zagrobelny
authors.forename: Karin
authors.initials: K
authors.lastname: Hjernø
authors.forename: Carl Erik
authors.initials: CE
authors.lastname: Olsen
authors.forename: Jens
authors.initials: J
authors.lastname: Houghton-Larsen
authors.forename: Jonas
authors.initials: J
authors.lastname: Borch
authors.forename: Birger Lindberg
authors.initials: BL
authors.lastname: Møller
authors.forename: Søren
authors.initials: S
authors.lastname: Bak
mesh_terms: D000595:Amino Acid Sequence; D000818:Animals; D016000:Cluster Analysis; D003577:Cytochrome P-450 Enzyme System / Q000235:genetics*; D019143:Evolution, Molecular; D056726:Genetic Association Studies; D005960:Glucosides; D006027:Glycosides / Q000096:biosynthesis*; D016695:Glycosyltransferases / Q000235:genetics*; D008958:Models, Molecular; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009036:Moths / Q000201:enzymology* / Q000235:genetics; D009570:Nitriles; D010802:Phylogeny; D010944:Plants / Q000201:enzymology* / Q000235:genetics; D013045:Species Specificity; D013057:Spectrum Analysis
chemical_list: D005960:Glucosides; D006027:Glycosides; D009570:Nitriles; C007173:cyanogenic glycosides; D003577:Cytochrome P-450 Enzyme System; D016695:Glycosyltransferases; C005091:linamarin; C001556:lotaustralin