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

Abstract In plants, cis-jasmone (CJ) is synthesized from α-linolenic acid (LA) via two biosynthetic pathways using jasmonic acid (JA) and iso-12-oxo-phytodienoic acid (iso-OPDA) as key intermediates. However, there have been no reports documenting CJ production by microorganisms. In the present stud...

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Autores principales:	Ryo Matsui, Naruki Amano, Kosaku Takahashi, Yodai Taguchi, Wataru Saburi, Hideharu Mori, Norio Kondo, Kazuhiko Matsuda, Hideyuki Matsuura
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2017
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/2ed71dbd77da4cdd8803ef4a1e2e8283
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spelling	oai:doaj.org-article:2ed71dbd77da4cdd8803ef4a1e2e82832021-12-02T12:32:23ZElucidation of the biosynthetic pathway of cis-jasmone in Lasiodiplodia theobromae10.1038/s41598-017-05851-72045-2322https://doaj.org/article/2ed71dbd77da4cdd8803ef4a1e2e82832017-07-01T00:00:00Zhttps://doi.org/10.1038/s41598-017-05851-7https://doaj.org/toc/2045-2322Abstract In plants, cis-jasmone (CJ) is synthesized from α-linolenic acid (LA) via two biosynthetic pathways using jasmonic acid (JA) and iso-12-oxo-phytodienoic acid (iso-OPDA) as key intermediates. However, there have been no reports documenting CJ production by microorganisms. In the present study, the production of fungal-derived CJ by Lasiodiplodia theobromae was observed for the first time, although this production was not observed for Botrytis cinerea, Verticillium longisporum, Fusarium oxysporum, Gibberella fujikuroi, and Cochliobolus heterostrophus. To investigate the biosynthetic pathway of CJ in L. theobromae, administration experiments using [18,18,18-2H3, 17,17-2H2]LA (LA-d5), [18,18,18-2H3, 17,17-2H2]12-oxo-phytodienoic acid (cis-OPDA-d5), [5′,5′,5′-2H3, 4′,4′-2H2, 3′-2H1]OPC 8:0 (OPC8-d6), [5′,5′,5′-2H3, 4′,4′-2H2, 3′-2H1]OPC 6:0 (OPC6-d6), [5′,5′,5′-2H3, 4′,4′-2H2, 3′-2H1]OPC 4:0 (OPC4-d6), and [11,11-2H2, 10,10-2H2, 8,8-2H2, 2,2-2H2]methyl iso-12-oxo-phytodienoate (iso-MeOPDA-d8) were carried out, revealing that the fungus produced CJ through a single biosynthetic pathway via iso-OPDA. Interestingly, it was suggested that the previously predicted decarboxylation step of 3,7-didehydroJA to afford CJ might not be involved in CJ biosynthesis in L. theobromae.Ryo MatsuiNaruki AmanoKosaku TakahashiYodai TaguchiWataru SaburiHideharu MoriNorio KondoKazuhiko MatsudaHideyuki MatsuuraNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 7, Iss 1, Pp 1-9 (2017)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Ryo Matsui Naruki Amano Kosaku Takahashi Yodai Taguchi Wataru Saburi Hideharu Mori Norio Kondo Kazuhiko Matsuda Hideyuki Matsuura Elucidation of the biosynthetic pathway of cis-jasmone in Lasiodiplodia theobromae
description	Abstract In plants, cis-jasmone (CJ) is synthesized from α-linolenic acid (LA) via two biosynthetic pathways using jasmonic acid (JA) and iso-12-oxo-phytodienoic acid (iso-OPDA) as key intermediates. However, there have been no reports documenting CJ production by microorganisms. In the present study, the production of fungal-derived CJ by Lasiodiplodia theobromae was observed for the first time, although this production was not observed for Botrytis cinerea, Verticillium longisporum, Fusarium oxysporum, Gibberella fujikuroi, and Cochliobolus heterostrophus. To investigate the biosynthetic pathway of CJ in L. theobromae, administration experiments using [18,18,18-2H3, 17,17-2H2]LA (LA-d5), [18,18,18-2H3, 17,17-2H2]12-oxo-phytodienoic acid (cis-OPDA-d5), [5′,5′,5′-2H3, 4′,4′-2H2, 3′-2H1]OPC 8:0 (OPC8-d6), [5′,5′,5′-2H3, 4′,4′-2H2, 3′-2H1]OPC 6:0 (OPC6-d6), [5′,5′,5′-2H3, 4′,4′-2H2, 3′-2H1]OPC 4:0 (OPC4-d6), and [11,11-2H2, 10,10-2H2, 8,8-2H2, 2,2-2H2]methyl iso-12-oxo-phytodienoate (iso-MeOPDA-d8) were carried out, revealing that the fungus produced CJ through a single biosynthetic pathway via iso-OPDA. Interestingly, it was suggested that the previously predicted decarboxylation step of 3,7-didehydroJA to afford CJ might not be involved in CJ biosynthesis in L. theobromae.
format	article
author	Ryo Matsui Naruki Amano Kosaku Takahashi Yodai Taguchi Wataru Saburi Hideharu Mori Norio Kondo Kazuhiko Matsuda Hideyuki Matsuura
author_facet	Ryo Matsui Naruki Amano Kosaku Takahashi Yodai Taguchi Wataru Saburi Hideharu Mori Norio Kondo Kazuhiko Matsuda Hideyuki Matsuura
author_sort	Ryo Matsui
title	Elucidation of the biosynthetic pathway of cis-jasmone in Lasiodiplodia theobromae
title_short	Elucidation of the biosynthetic pathway of cis-jasmone in Lasiodiplodia theobromae
title_full	Elucidation of the biosynthetic pathway of cis-jasmone in Lasiodiplodia theobromae
title_fullStr	Elucidation of the biosynthetic pathway of cis-jasmone in Lasiodiplodia theobromae
title_full_unstemmed	Elucidation of the biosynthetic pathway of cis-jasmone in Lasiodiplodia theobromae
title_sort	elucidation of the biosynthetic pathway of cis-jasmone in lasiodiplodia theobromae
publisher	Nature Portfolio
publishDate	2017
url	https://doaj.org/article/2ed71dbd77da4cdd8803ef4a1e2e8283
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Elucidation of the biosynthetic pathway of cis-jasmone in Lasiodiplodia theobromae

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