title: The inhibitory activity of natural products on plant p-hydroxyphenylpyruvate dioxygenase.
abstract: The inhibitory activity of 34 natural products of various structural classes on hydroxyphenylpyruvate dioxygenase (HPPD), the target site for triketone herbicides, and the mode of interaction of selected natural products were investigated. Recombinant HPPD from arabidopsis is sensitive to several classes of natural compounds including, in decreasing order of sensitivity, triketones, benzoquinones, naphthoquinones and anthraquinones. The triketone natural products acted as competitive tight-binding inhibitors, whereas the benzoquinones and naphthoquinones did not appear to bind tightly to HPPD. While these natural products may not have optimal structural features required for in vivo herbicidal activity, the differences in their kinetic behavior suggest that novel classes of HPPD inhibitors may be developed based on their structural backbones.
authors.affiliation: Isagro Ricerca Srl, via G. Fauser, 4, 28100 Novara, Italy.
authors.forename: Giovanni
authors.initials: G
authors.lastname: Meazza
authors.forename: Brian E
authors.initials: BE
authors.lastname: Scheffler
authors.forename: Mario R
authors.initials: MR
authors.lastname: Tellez
authors.forename: Agnes M
authors.initials: AM
authors.lastname: Rimando
authors.forename: Joanne G
authors.initials: JG
authors.lastname: Romagni
authors.forename: Stephen O
authors.initials: SO
authors.lastname: Duke
authors.forename: Dhammika
authors.initials: D
authors.lastname: Nanayakkara
authors.forename: Ikhlas A
authors.initials: IA
authors.lastname: Khan
authors.forename: Ehab A
authors.initials: EA
authors.lastname: Abourashed
authors.forename: Franck E
authors.initials: FE
authors.lastname: Dayan
mesh_terms: D015111:4-Hydroxyphenylpyruvate Dioxygenase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D000880:Anthraquinones / Q000494:pharmacology; D017360:Arabidopsis / Q000201:enzymology*; D016227:Benzoquinones / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products / Q000737:chemistry / Q000494:pharmacology*; D006540:Herbicides / Q000494:pharmacology; D009285:Naphthoquinones / Q000737:chemistry / Q000494:pharmacology; D011994:Recombinant Proteins / Q000037:antagonists & inhibitors / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: D000880:Anthraquinones; D016227:Benzoquinones; D001688:Biological Products; D006540:Herbicides; D009285:Naphthoquinones; D011994:Recombinant Proteins; C004532:quinone; D015111:4-Hydroxyphenylpyruvate Dioxygenase