Pyrethric acid of natural pyrethrin insecticide: complete pathway elucidation and reconstitution in Nicotiana benthamiana

Autor: Ric C. H. de Vos, Henriëtte D. L. M. van Eekelen, Anthony L. Schilmiller, Haiyang Xu, Maarten A. Jongsma, Wei Li, Eran Pichersky
Jazyk: angličtina
Rok vydání: 2019
Předmět:
0106 biological sciences
0301 basic medicine
Insecticides
Methyltransferase
type II pyrethrins
Physiology
Stereochemistry
cytochrome P450 oxidoreductase
Nicotiana benthamiana
Plant Science
Flowers
01 natural sciences
Methylation
pyrethric acid
Catalysis
Substrate Specificity
03 medical and health sciences
chemistry.chemical_compound
Cytochrome P-450 Enzyme System
aldehyde dehydrogenase
Gene Expression Regulation
Plant
Pyrethrin
Pyrethrins
Tobacco
Moiety
Tanacetum cinerariifolium
Gene
Phylogeny
Plant Proteins
chemistry.chemical_classification
Chrysanthemum cinerariifolium
biology
Plant Extracts
alcohol dehydrogenase
SABATH methyltransferase
biology.organism_classification
Biosynthetic Pathways
Chrysanthemic acid
Plant Leaves
030104 developmental biology
Enzyme
chemistry
BIOS Applied Metabolic Systems
natural insecticides
010606 plant biology & botany
Zdroj: New Phytologist, 223(2), 751-765
New Phytologist 223 (2019) 2
ISSN: 0028-646X
Popis: In the natural pesticides known as pyrethrins, which are esters produced in flowers of Tanacetum cinerariifolium (Asteraceae), the monoterpenoid acyl moiety is pyrethric acid or chrysanthemic acid. We show here that pyrethric acid is produced from chrysanthemol in six steps catalyzed by four enzymes, the first five steps occurring in the trichomes covering the ovaries and the last one occurring inside the ovary tissues. Three steps involve the successive oxidation of carbon 10 (C10) to a carboxylic group by TcCHH, a cytochrome P450 oxidoreductase. Two other steps involve the successive oxidation of the hydroxylated carbon 1 to give a carboxylic group by TcADH2 and TcALDH1, the same enzymes that catalyze these reactions in the formation of chrysanthemic acid. The ultimate result of the actions of these three enzymes is the formation of 10‐carboxychrysanthemic acid in the trichomes. Finally, the carboxyl group at C10 is methylated by TcCCMT, a member of the SABATH methyltransferase family, to give pyrethric acid. This reaction occurs mostly in the ovaries. Expression in N. benthamiana plants of all four genes encoding aforementioned enzymes, together with TcCDS, a gene that encodes an enzyme that catalyzes the formation of chrysanthemol, led to the production of pyrethric acid.
Databáze: OpenAIRE
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