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Jasmonic acid is not a biosynthetic intermediate to produce the pyrethrolone moiety in pyrethrin II
Pyrethrum (Tanacetum cinerariifolium) produces insecticidal compounds known as pyrethrins. Pyrethrins are esters; the acid moiety is either trans-chrysanthemic acid or pyrethric acid and the alcohol moiety of pyrethrins is either pyrethrolone, cinerolone, or jasmolone. It was generally accepted that...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7156398/ https://www.ncbi.nlm.nih.gov/pubmed/32286354 http://dx.doi.org/10.1038/s41598-020-63026-3 |
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author | Matsui, Ryo Takiguchi, Kisumi Kuwata, Naoshige Oki, Katsunari Takahashi, Kosaku Matsuda, Kazuhiko Matsuura, Hideyuki |
author_facet | Matsui, Ryo Takiguchi, Kisumi Kuwata, Naoshige Oki, Katsunari Takahashi, Kosaku Matsuda, Kazuhiko Matsuura, Hideyuki |
author_sort | Matsui, Ryo |
collection | PubMed |
description | Pyrethrum (Tanacetum cinerariifolium) produces insecticidal compounds known as pyrethrins. Pyrethrins are esters; the acid moiety is either trans-chrysanthemic acid or pyrethric acid and the alcohol moiety of pyrethrins is either pyrethrolone, cinerolone, or jasmolone. It was generally accepted that cis-jasmone was biosynthetic intermediate to produce the alcohol moieties of pyrethrin, and the biosynthetic origin of the cis-jasmone was postulated to be jasmonic acid. However, there was no direct evidence to prove this hypothesis. In order to uncover the origin of pyrethrolone moiety in pyrethrin II, feeding experiments were performed employing deuterium- and (13)C-labeled compounds as substrates, and the expected labeled compounds were analyzed using UPLC MS/MS system. It was found that the pyrethrolone moiety in pyrethrin II was derived from 12-oxo-phytodienoic acid (OPDA), iso-OPDA and cis-jasmone but not from methyl jasmonate and 3-oxo-2-(2′-[Z]-pentenyl)-cyclopentane-1-hexanoic acid. The results supported that the biosynthesis of the pyrethrolone moiety in pyrethrin II partially used part of the jasmonic acid biosynthetic pathway, but not whole. |
format | Online Article Text |
id | pubmed-7156398 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-71563982020-04-19 Jasmonic acid is not a biosynthetic intermediate to produce the pyrethrolone moiety in pyrethrin II Matsui, Ryo Takiguchi, Kisumi Kuwata, Naoshige Oki, Katsunari Takahashi, Kosaku Matsuda, Kazuhiko Matsuura, Hideyuki Sci Rep Article Pyrethrum (Tanacetum cinerariifolium) produces insecticidal compounds known as pyrethrins. Pyrethrins are esters; the acid moiety is either trans-chrysanthemic acid or pyrethric acid and the alcohol moiety of pyrethrins is either pyrethrolone, cinerolone, or jasmolone. It was generally accepted that cis-jasmone was biosynthetic intermediate to produce the alcohol moieties of pyrethrin, and the biosynthetic origin of the cis-jasmone was postulated to be jasmonic acid. However, there was no direct evidence to prove this hypothesis. In order to uncover the origin of pyrethrolone moiety in pyrethrin II, feeding experiments were performed employing deuterium- and (13)C-labeled compounds as substrates, and the expected labeled compounds were analyzed using UPLC MS/MS system. It was found that the pyrethrolone moiety in pyrethrin II was derived from 12-oxo-phytodienoic acid (OPDA), iso-OPDA and cis-jasmone but not from methyl jasmonate and 3-oxo-2-(2′-[Z]-pentenyl)-cyclopentane-1-hexanoic acid. The results supported that the biosynthesis of the pyrethrolone moiety in pyrethrin II partially used part of the jasmonic acid biosynthetic pathway, but not whole. Nature Publishing Group UK 2020-04-14 /pmc/articles/PMC7156398/ /pubmed/32286354 http://dx.doi.org/10.1038/s41598-020-63026-3 Text en © The Author(s) 2020 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/. |
spellingShingle | Article Matsui, Ryo Takiguchi, Kisumi Kuwata, Naoshige Oki, Katsunari Takahashi, Kosaku Matsuda, Kazuhiko Matsuura, Hideyuki Jasmonic acid is not a biosynthetic intermediate to produce the pyrethrolone moiety in pyrethrin II |
title | Jasmonic acid is not a biosynthetic intermediate to produce the pyrethrolone moiety in pyrethrin II |
title_full | Jasmonic acid is not a biosynthetic intermediate to produce the pyrethrolone moiety in pyrethrin II |
title_fullStr | Jasmonic acid is not a biosynthetic intermediate to produce the pyrethrolone moiety in pyrethrin II |
title_full_unstemmed | Jasmonic acid is not a biosynthetic intermediate to produce the pyrethrolone moiety in pyrethrin II |
title_short | Jasmonic acid is not a biosynthetic intermediate to produce the pyrethrolone moiety in pyrethrin II |
title_sort | jasmonic acid is not a biosynthetic intermediate to produce the pyrethrolone moiety in pyrethrin ii |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7156398/ https://www.ncbi.nlm.nih.gov/pubmed/32286354 http://dx.doi.org/10.1038/s41598-020-63026-3 |
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