Biosynthesis and metabolism of jasmonates

Schaller, Florian; Schaller, Andreas; Stintzi, Annick

doi:10.1007/bf02637260

Cited by 95 publications

(147 citation statements)

References 184 publications

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“…In addition, methyl jasmonate is the main component of the scent of jasmine flowers and contributes to the precious flavors of Rosmarinus, Gardenia, Artemisia and lemon oil. cis-jasmone, which acts as either an attractant or a repellent for various insects, is a decarboxylated derivative of jasmonic acid generated by oxidative degradation of jasmonate (Schaller et al, 2005).…”

Section: Fatty Acid-derived and Other Lipophylic Flavor Compoundsmentioning

confidence: 99%

Biosynthesis of plant‐derived flavor compounds

Schwab¹,

Davidovich‐Rikanati²,

Lewinsohn³

2008

The Plant Journal

942

704

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SummaryPlants have the capacity to synthesize, accumulate and emit volatiles that may act as aroma and flavor molecules due to interactions with human receptors. These low-molecular-weight substances derived from the fatty acid, amino acid and carbohydrate pools constitute a heterogenous group of molecules with saturated and unsaturated, straight-chain, branched-chain and cyclic structures bearing various functional groups (e.g. alcohols, aldehydes, ketones, esters and ethers) and also nitrogen and sulfur. They are commercially important for the food, pharmaceutical, agricultural and chemical industries as flavorants, drugs, pesticides and industrial feedstocks. Due to the low abundance of the volatiles in their plant sources, many of the natural products had been replaced by their synthetic analogues by the end of the last century. However, the foreseeable shortage of the crude oil that is the source for many of the artifical flavors and fragrances has prompted recent interest in understanding the formation of these compounds and engineering their biosynthesis. Although many of the volatile constituents of flavors and aromas have been identified, many of the enzymes and genes involved in their biosynthesis are still not known. However, modification of flavor by genetic engineering is dependent on the knowledge and availability of genes that encode enzymes of key reactions that influence or divert the biosynthetic pathways of plant-derived volatiles. Major progress has resulted from the use of molecular and biochemical techniques, and a large number of genes encoding enzymes of volatile biosynthesis have recently been reported.

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Section: Fatty Acid-derived and Other Lipophylic Flavor Compoundsmentioning

confidence: 99%

Biosynthesis of plant‐derived flavor compounds

Schwab¹,

Davidovich‐Rikanati²,

Lewinsohn³

2008

The Plant Journal

942

704

View full text Add to dashboard Cite

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“…JAs were then shown to be active inducers of antimicrobial phytoalexins by Gundlach et al (1992), and subsequent work clearly established their defense gene-inducing activity for induced resistance against insect predators and pathogens (for a review, see Reymond and Farmer, 1998;Weiler et al, 1998;Blé e, 2002). Such a role was unequivocally confirmed by the analysis of mutants compromised in either the synthesis or the perception of JA signals (for a review, see Schaller et al, 2005).…”

Section: Introductionmentioning

confidence: 95%

The Crystal Structure of Arabidopsis thaliana Allene Oxide Cyclase: Insights into the Oxylipin Cyclization Reaction

2006

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We describe the crystallization and structure elucidation of Arabidopsis thaliana allene oxide cyclase 2 (AOC2), a key enzyme in the biosynthesis of jasmonates. In a coupled reaction with allene oxide synthase, AOC2 releases the first cyclic and biologically active metabolite, 12-oxo-phytodienoic acid (OPDA). AOC2 (AT3G25770) folds into an eight-stranded antiparallel b-barrel with a C-terminal partial helical extension. The protein forms a hydrophobic binding cavity with two distinct polar patches. AOC2 is trimeric in crystals, in vitro and in planta. Based on the observed folding pattern, we assigned AOC2 as a low molecular weight member of the lipocalin family with enzymatic activity in plants. We determined the binding position of the competitive inhibitor vernolic acid (a substrate analog) in the binding pocket. Based on models for bound substrate 12,13-epoxy-9,11,15-octadecatrienoic acid and product OPDA, we propose a reaction scheme that explains the influence of the C15 double bond on reactivity. Reaction is promoted by anchimeric assistance through a conserved Glu residue. The transition state with a pentadienyl carbocation and an oxyanion is stabilized by a strongly bound water molecule and favorable p-p interactions with aromatic residues in the cavity. Stereoselectivity results from steric restrictions to the necessary substrate isomerizations imposed by the protein.

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“…This is an important fact, since lipid acyl hydrolases are lipolytic enzymes that are involved in changes of membrane lipids and release fatty acids (Galliard, 1971). Linolenic acid, for example, can serve as precursors for the biosynthesis of jasmonic acid and its derivatives known for their regular function in plant defence and adaptation to stressful conditions (Schaller et al, 2005;Creelman & Mullet, 1997). Moreover, acyl hydrolases can stimulate the mobilization of lipid reserves to provide sugars that are involved in osmotic adjustment (Creelman & Mullet, 1997).…”

Section: The Effect Of Drought Stress On Soluble Proteins Lipid Acylmentioning

confidence: 99%

Influence of Drought and Wounding Stress on Soluble Phenols and Proteins in Potato Tubers

Wegener¹,

Jansen²,

Jürgens³

2014

SAR

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Potato is a valuable source for phytochemicals like vitamins, minerals, plant phenols, amino acids and proteins. However, environmental stress may affect the level of all these components. In this study, two purple breeding clones and one yellow fleshed cultivar (cv.) were assessed in their response to drought and wounding stress in two consecutive years. The plants were grown in the greenhouse under control (sufficient water supply) and with drought stress conditions. After harvest the tubers were analyzed for the content of soluble phenols and proteins in fresh tissue and after wounding. In addition, free amino acids (AAS) and activity of lipid acyl hydrolases (LAH) were assayed in control and drought stressed tubers. The results revealed significant differences in soluble phenols and proteins between genotypes, and that drought stress significantly increased the level of soluble proteins (P < 0.0001) and LAH activity (P < 0.001), but had no significant effect on the concentration of phenols. Moreover, total amounts of free AAS were higher in the drought stress variant. Wounding stress caused a significant increase of soluble phenols in cv. Agave. But, this was less prominent in purple clones which in general had higher contents of phenols. Proteins were also enhanced as a result of wounding, although, the effect of wounding stress on their level was smaller than that of drought stress.

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Biosynthesis and metabolism of jasmonates

Cited by 95 publications

References 184 publications

Biosynthesis of plant‐derived flavor compounds

Biosynthesis of plant‐derived flavor compounds

The Crystal Structure of Arabidopsis thaliana Allene Oxide Cyclase: Insights into the Oxylipin Cyclization Reaction

Influence of Drought and Wounding Stress on Soluble Phenols and Proteins in Potato Tubers

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