Elucidation of the biosynthetic pathway of cis-jasmone in Lasiodiplodia theobromae

Matsui, Ryota; Amano, Naruki; Takahashi, Kosaku; Taguchi, Yodai; Saburi, Wataru; Mori, Haruhide; Kondo, Norio; Matsuda, Kazuhiko; Matsuura, Hideyuki

doi:10.1038/s41598-017-05851-7

Cited by 23 publications

(22 citation statements)

References 38 publications

(39 reference statements)

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“…S8). One was S8a) assumed from the biosynthetic pathway reported by Koch et al 10 , and the other was 19,20 . An anhydrous lanolin paste (100 mg) containing Me-iso-OPDA-d 10 (10 μmol) was applied to the leaves of pyrethrum, and the treated leaves were harvested after 24 h. The analyses using UPLC MS/MS in MRM mode targeting endogenous (Fig.…”

Section: Resultsmentioning

confidence: 97%

“…Synthesis of [ 2 H 2 -4, 2 H 2 -3, 2 H 3 -1] cis-jasmone (Fig. 4a, CJ-d 7 ) was performed according to the reported method 19 , and used for feeding experiments. In the case of the compound being incorporated into pyrethrin II, the predicted labeled compound was [ 2 H 2 -4′, 2 H 1 -3′, 2 H 3 -1′] pyrethrin II (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…[ (Fig. 5a, Me-iso-OPDA-d 10 ) was synthesized according to the reported method 19 . In the case of the applied compound being incorporated into pyrethrin II, two types of labeled compounds were predicted (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…It was reported that α-LA is a starting compound to produce OPDA and the pyrethrolone moiety of pyrethrin I 14,26 . In a previous paper, we reported that a pathogenic fungus, Lasiodiplodia theobromae, synthesized cis-jasmone via iso-OPDA, while JA was not incorporated into the compound 19 . However, Koch et al reported that exogenously applied JA was metabolized to cis-jasmone 10 .…”

Section: Detection Of Pyrethrins In the Leaves Of Pyrethrum By Uplc Mmentioning

confidence: 99%

“…However, Dabrowska et al reported another biosynthetic pathway of cis-jasmone via iso-OPDA (Fig. 2) 18 , and it was recently found that cis-jasmone produced in the pathogenic fungus, Lasiodiplodia theobromae was derived from α-LA, OPDA, and iso-OPDA but not from OPCs 8:0, 6:0, 4:0 and JA 19,20 . Therefore, at present, it cannot be clearly stated that the biosynthetic origin of pyrethrolone, cinerolone, and jasmolone moieties in pyrethrin is JA, although it was generally accepted that JA is involved to produce the alcohol moieties in pyrethrin.…”

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confidence: 99%

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Jasmonic acid is not a biosynthetic intermediate to produce the pyrethrolone moiety in pyrethrin II

Matsui

Takiguchi

Kuwata

et al. 2020

Sci Rep

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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. Pyrethrum (Tanacetum cinerariifolium, formerly Chrysanthemum cinerariifolium) is a plant in the Asteraceae family that synthesizes insecticides known as pyrethrin (Fig. 1), and it was found that the highest levels of production were observed in flowers 1,2 , whereas a smaller amount was observed in leaves. Since pyrethrin shows remarkable toxicity against a wide range of insect species but low toxicity to warm-blooded animals, pyrethrin has been used for pest control 1. Until the middle of the 20 th century, Japan was the world's largest producer of pyrethrum, and it had been thought to be ideal to collect flowers before they were fully opened. However, pyrethroids, which are synthetic analogs of pyrethrin, are used at much higher amounts than pyrethrin as pest control agents due to their lower cost to produce and their effectiveness, even though they are less safe to vertebrates and less biodegradable 3,4. Recently, some researchers have noted the emergence of resistance among insects and toxicity toward mammals and fish 5. From the chemical structural viewpoint, pyrethrin has ester linkages in the chemical structure and is classified into two types (Fig. 1): type I esters have a chrysanthemoyl moiety, whereas type II esters have a pyrethroyl moiety having additional ester linkage composing methoxycarbonyl group. A common and distinctive structural feature of the acid moieties is a cyclopropane ring moiety. The alcohol-containing parts of pyrethrin are either pyrethrolone, cinerolone, or jasmolone, which all have a similar basic structure with that of cis-jasmone. The enzyme producing the ester linkage was identified as a GDSL lipase-like protein 6 , which was encoded on TcGLIP (Fig. S1). The synthesis of the acid and alcohol moieties of pyrethrin is not fully understood. For the acid moiety, it was demonstrated that T. cinerariifolium flowers have the enzyme trans-chr...

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Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Detection Of Pyrethrins In the Leaves Of Pyrethrum By Uplc Mmentioning

confidence: 99%

mentioning

confidence: 99%

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Jasmonic acid is not a biosynthetic intermediate to produce the pyrethrolone moiety in pyrethrin II

Matsui

Takiguchi

Kuwata

et al. 2020

Sci Rep

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High production of jasmonic acid by Lasiodiplodia iranensis using solid‐state fermentation: Optimization and understanding

Shen

Zheng

et al. 2022

Biotechnology Journal

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Background Jasmonic acid (JA) is a plant hormone involved in regulating developmental and growth controls as well as photosynthesis. In addition, this hormone protects the plant against insects and has good applications in agriculture, the flavored industry and other fields. Filamentous fungus generally produces JA using liquid static culture. In the present study, a solid‐state fermentation (SSF) method is developed for high production of JA using Lasiodiplodia iranensis. Main methods and major results By selecting the solid substrate and optimizing the initial water content, inoculum volume, loading volume and other culture conditions, the maximum JA yield reached 5306.38 mg kg–1 when fermented for 12 days in a petri dish containing a medium with crushed wheat as the solid substrate and 75% initial water content. The logistic and Luedeking–Piret models were used to characterize the relationship between microbial growth and product synthesis in the SSF process, and the maximum JA production is predicted to be 5263.23 mg kg–1, which is close to the experimental value. Liquid chromatography with tandem mass spectrometry (LC‐MS/MS) is used to examine the metabolic changes that develop during fermentation. The results indicate that JA biosynthesis occurs in the α‐linolenic acid metabolic pathway, of which 13(S)‐HpOTrE is a key intermediate metabolite and both 13(S)‐HOTrE and traumatic acid are byproducts of the branches of its synthesis. Conclusions and implications The results of this study provide a method for obtaining high JA yields by SSF, and offer new insights for understanding the production of JA by fungal fermentation.

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Investigation Of The Biosynthesis Pathway That Generates cis‐Jasmone

Inoue,

Tsuzuki,

Matsuda

et al. 2023

ChemBioChem

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Researchers have established that (+)‐7‐iso‐jasmonic acid ((+)‐7‐iso‐JA) is an intermediate in the production of cis‐jasmone (CJ); however, the biosynthetic pathway of CJ has not been fully described. Previous reports stated that CJ, a substructure of pyrethrin II produced by pyrethrum (Tanacetum cinerariifolium), is not biosynthesized through this biosynthetic pathway. To clarify the ambiguity, stable isotope‐labelled jasmonates were synthesized, and compounds were applied to apple mint (Mentha suaveolens) via air propagation. The results showed that cis‐jasmone is not generated from intermediate (+)‐7‐iso‐JA, and (+)‐7‐iso‐JA is not produced from 3,7‐dideydro‐JA (3,7‐ddh‐JA); however, 3,7‐didehydro‐JA and 4,5‐didehydro‐7‐iso‐JA were converted into CJ and JA, respectively.

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Elucidation of the biosynthetic pathway of cis-jasmone in Lasiodiplodia theobromae

Cited by 23 publications

References 38 publications

Jasmonic acid is not a biosynthetic intermediate to produce the pyrethrolone moiety in pyrethrin II

Jasmonic acid is not a biosynthetic intermediate to produce the pyrethrolone moiety in pyrethrin II

High production of jasmonic acid by Lasiodiplodia iranensis using solid‐state fermentation: Optimization and understanding

Investigation Of The Biosynthesis Pathway That Generates cis‐Jasmone

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