Biosynthesis and in vitro enzymatic synthesis of the isoleucine conjugate of 12-oxo-phytodienoic acid from the isoleucine conjugate of α-linolenic acid. Issue 6 (1st April 2018)

• Record Type: Journal Article
• Authors: Uchiyama, Akira; Yaguchi, Takaomi; Nakagawa, Hiroyuki; Sasaki, Kento; Kuwata, Naoshige; Matsuura, Hideyuki; Takahashi, Kosaku
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 28:Issue 6(2018)
• Page Start: 1020
• Page End: 1023
• Publication Date: 2018-04-01
• Subjects: AOC allene oxide cyclase -- AOS allene oxide synthase -- COI1 coronatine insensitive 1 -- 12, 13-EOT allene oxide -- FW fresh weight -- GC–MS gas chromatography-mass spectrometry -- 13-HPOT 13(S)-hydroperoxyoctadecatrienoic acid -- JA jasmonic acid -- JA-Ile jasmonoyl-l-isoleucine -- JAR1 jasmonic acid-resistant 1 -- JAZ jasmonate-ZIM domain -- LC-MS/MS liquid chromatography-tandem mass spectrometry -- LA-Ile isoleucine conjugate of α-linolenic acid -- OPC-8:0 3-oxo-2-(cis-2′-pentenyl)-cyclopentane-1-octanoic acid -- OPDA-Ile isoleucine conjugate of OPDA -- OPR 12-oxo-phytodienoic acid reductase -- SCF skp-cullin-F box; Arabidopsis thaliana -- Jasmonates -- LA-Ile -- OPDA-Ile -- 12-oxo-phytodienoic acid; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2018.02.030
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: The isoleucine conjugate of 12-oxo-phytodienoic acid (OPDA-Ile), a new member of the jasmonate family, was recently identified in Arabidopsis thaliana and might be a signaling molecule in plants. However, the biosynthesis and function of OPDA-Ile remains elusive. This study reports an in vitro enzymatic method for synthesizing OPDA-Ile, which is catalyzed by reactions of lipoxygenase (LOX), allene oxide synthase (AOS), and allene oxide cyclase (AOC) using isoleucine conjugates of α -linolenic acid (LA-Ile) as the substrate. A. thaliana fed LA-Ile exhibited a marked increase in the OPDA-Ile concentration. LA-Ile was also detected in A. thaliana. Furthermore, stable isotope labelled LA-Ile was incorporated into OPDA-Ile. Thus, OPDA-Ile is biosynthesized via the cyclization of LA-Ile in A. thaliana.