Pyrethric acid of natural pyrethrin insecticide: complete pathway elucidation and reconstitution in Nicotiana benthamiana
| العنوان: | Pyrethric acid of natural pyrethrin insecticide: complete pathway elucidation and reconstitution in Nicotiana benthamiana |
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| المؤلفون: | Ric C. H. de Vos, Henriëtte D. L. M. van Eekelen, Anthony L. Schilmiller, Haiyang Xu, Maarten A. Jongsma, Wei Li, Eran Pichersky |
| المصدر: | New Phytologist, 223(2), 751-765 New Phytologist 223 (2019) 2 |
| سنة النشر: | 2019 |
| مصطلحات موضوعية: | 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 |
| الوصف: | 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. |
| وصف الملف: | application/octet-stream; application/pdf |
| اللغة: | English |
| تدمد: | 0028-646X |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::1e7abb4afeafb901726600e98fe7ab00 https://research.wur.nl/en/publications/pyrethric-acid-of-natural-pyrethrin-insecticide-complete-pathway- |
| Rights: | OPEN |
| رقم الانضمام: | edsair.doi.dedup.....1e7abb4afeafb901726600e98fe7ab00 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 0028646X |
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