Dinor-oxo-phytodienoic acid: a new hexadecanoid signal in the jasmonate family

• Published in: Proceedings of the National Academy of Sciences - PNAS 1997-09, Vol.94 (19), p.10473-10478
• Main Authors: Weber, H, Vick, B.A, Farmer, E.E
• Format: Article
• Language: English
• Subjects: ACIDE GRAS; ACIDE JASMONIQUE; ACIDE LINOLEIQUE; ACIDO JASMONICO; ACIDO LINOLEICO; ACIDOS GRASOS; Arabidopsis - growth & development; Arabidopsis - metabolism; ARABIDOPSIS THALIANA; Biological Sciences; Cyclopentanes - metabolism; DANOS MECANICOS; DEGAT MECANIQUE; DERIVATIVES; Esters; Ethers; Family members; FATTY ACIDS; Fatty Acids, Unsaturated - isolation & purification; Fatty Acids, Unsaturated - metabolism; FEUILLE; Flaxseed; HOJAS; ISOLATION; JASMONIC ACID; LEAVES; LINOLEIC ACID; LONG CHAIN FATTY ACIDS; Mass Spectrometry; MECHANICAL DAMAGE; Molecules; OXIDACION; OXIDATION; OXYDATION; Oxylipins; Plant Growth Regulators - metabolism; Plant tissues; Plants; PRECURSORS; Signal Transduction; SOLANUM TUBEROSUM; Solvents
• ISSN: 0027-8424; 1091-6490
• DOI: 10.1073/pnas.94.19.10473

Jasmonic acid and its precursors are potent regulatory molecules in plants. We devised a method for the simultaneous extraction of these compounds from plant leaves to quantitate changes in the levels of jasmonate family members during health and on wounding. During our study, we identified a novel 16-carbon cyclopentenoic acid in leaf extracts from Arabidopsis and potato. The new compound, a member of the jasmonate family of signals, was named dinor-oxo-phytodienoic acid. Dinor-oxo-phytodienoic acid was not detected in the Arabidopsis mutant fad5, which is incapable of synthesizing 7Z,10Z,13Z-hexadecatrienoic acid (16:3), suggesting that the metabolite is derived directly from plastid 16:3 rather than by beta-oxidation of the 18-carbon 12-oxo-phytodienoic acid. Simultaneous quantitation of jasmonate family members in healthy leaves of Arabidopsis and potato suggest that different plant species have different relative levels of jasmonic acid, oxo- phytodienoic acid, and dinor-oxo-phytodienoic acid. We term these profiles "oxylipin signatures." Dinor-oxo-phytodienoic acid levels increased dramatically in Arabidopsis and potato leaves on wounding, suggesting roles in wound signaling. Treatment of Arabidopsis with micromolar levels of dinor-oxo-phytodienoic acid increased the ability of leaf extracts to transform linoleic acid into the alpha-ketol 13-hydroxy-12-oxo-9(Z) octadecenoic acid indicating that the compound can regulate part of its own biosynthetic pathway. Tightly regulated changes in the relative levels of biologically active jasmonates may permit sensitive control over metabolic, developmental, and defensive processes in plants