Jasmonic acid biosynthesis by fungi: derivatives, first evidence on biochemical pathways and culture conditions for production

Abstract

Jasmonic acid (JA) and its derivatives called jasmonates (JAs) are lipid-derived signalling molecules that are produced by plants and certain fungi. Beside this function, JAs have a great variety of applications in flavours and fragrances production. In addition, they may have a high potential in agriculture. JAs protect plants against infections. Although there is much information on the biosynthesis and function of JA concerning plants, knowledge on these aspects is still scarce for fungi. Taking into account the practical importance of JAs, the objective of this review is to summarize knowledge on the occurrence of JAs from fungal culture media, their biosynthetic pathways and the culture conditions for optimal JA production as an alternative source for the production of these valuable metabolites.

Keywords: Culture medium; Fungi; Jasmonic acid; Metabolic pathway; Oxylipin; Submerged fermentation.

Figure 1. Chemical structure of the most important jasmonates found in fungi.

(A) Trans-compounds: 1, jasmonic acid; 2, jasmonic acid methyl ester; 3, jasmonoyl isoleucine, glycine, serine and threonine conjugates; 4, 3-oxo-2-(2-pentenyl)-1-butyric acid; 5, 3-oxo-2-(2-pentenyl)cyclopentane-1-hexanoic acid; 6, 3-oxo-2-(2-pentenyl)cyclopentane-1-octanoic acid; 7, 9,10-didehydro-JA; 8, 9,10-dihydro-7-iso-jasmonoyl-isoleucine; 9, 3-oxo-2-pentanylcyclopentane-1-butyric acid; 10, 3-oxo-2-pentanylcyclopentane-1-hexanoic acid; 11, 3-oxo-2-pentanyl)cyclopentane-1-octanoic acid. (B) cis-compounds: 1, jasmonic acid; 2, jasmonoyl isoleucine, glycine, serine and threonine conjugates; 3, 3-oxo-2-(2-pentenyl)-1-butyric acid; 4, 3-oxo-2-(2-pentenyl)cyclopentane-1-hexanoic acid; 5, 3-oxo-2-(2-pentenyl)cyclopentane-1-octanoic acid; 6, 9,10-didehydro-JA; 7, 9,10-dihydro-7-iso-jasmonoyl-isoleucine; 8, 3-oxo-2-pentanylcyclopentane-1-butyric acid; 9, 3-oxo-2-pentanylcyclopentane-1-hexanoic acid; 10, 3-oxo-2-pentanyl)cyclopentane-1-octanoic acid (all of them was found with trans- or cis-attached side chains). (C) 1, 2-(-3-hydroxy-2-(-pent-2-en-1-yl)cyclopentyl)acetic acid; 2, 8-hydroxy jasmonic acid; 3, 2-(-2-(-4-hydroxypent-2-en-1-yl)-3-oxocyclopentyl)acetic acid; 4, 4-(2-(4-hydroxypent-2-en-1-yl)-3-oxocyclopentyl)butanoic acid; 5, 4-(-2-(-1-hydroxypent-2-en-1-yl)-3-oxocyclopentyl) butanoic acid; 6: tuberonic acid; 7: 12-hydroxy jasmonic acid sulfate.

Figure 2. Synthesis of JA and its amino acid-conjugate JA-Ile in plants and fungi.

Synthesis of JA and its amino acid-conjugate JA-Ile in plants (A) and a scheme for OPDA formation in fungi. (B) Enzymes known only for Arabidopsis thaliana are indicated in yellow circles and those known from fungi are marked by grey circles. Abbreviations: AOC, allene oxide cyclase; AOS, allene oxide synthase; ddh-JA, 4,5-didehydro jasmonic acid; JA, jasmonic acid; JA-Ile, jasmonic acid isoleucine conjugate; JAR1, jasmonoyl amino acid conjugate synthase; LOX, lipoxygenase; OPC:8, 3-oxo-2-(2-pentenyl)-cyclopentane-1-octanoic acid; OPDA, cis-(+)-12-oxo-phytodienoic acid; OPR2,3, 12-oxo-phytodienoic acid reductase.