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. 2019 Dec 3;9:18249. doi: 10.1038/s41598-019-54815-6

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© The Author(s) 2019

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/.

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Flower of T. cinerariifolium (A) and biosynthetic pathway of pyrethrins (B). Proposed biosynthetic pathway of pyrethrins. Chrysanthemic acid and pyrethric acid as acid moieties are synthesized from dimethylallyl diphosphates by T. cinerariifolium chrysanthemyl diphosphate synthase (TcCDS), T. cinerariifolium alcohol dehydrogenase 2 (TcADH2), T. cinerariifolium aldehyde dehydrogenase 1 (TcALDH1), T. cinerariifolium chrysanthemol 10-hydroxylase (TcCHH), and T. cinerariifolium 10-carboxychrysanthemic acid 10-methyltransferase (TcCCMT). Pyrethrolone, jasmolone, and cinerolone as alcohol moieties are synthesized from linolenic acid by enzymes related to oxylipin pathway, including T. cinerariifolium jasmone hydroxylase (TcJMH), and unknown enzyme(s). Finally, chrysanthemoyl-CoA (the CoA-activated version of chrysanthemic acid) and pyrethrolone are esterified by T. cinerariifolium GDSL (Gly-Asp-Ser-Leu motif) lipase (TcGLIP) to produce pyrethrin I. Compounds and enzymes are indicated by red and blue text, respectively. Unidentified enzymes are indicated as question marks.