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Publikationen - Molekulare Signalverarbeitung

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Publikation

Wasternack, C.; Feussner, I.; The Oxylipin Pathways: Biochemistry and Function Annu. Rev. Plant Biol. 69, 363-386, (2018) DOI: 10.1146/annurev-arplant-042817-040440

Plant oxylipins form a constantly growing group of signaling molecules that comprise oxygenated fatty acids and metabolites derived therefrom. In the last decade, the understanding of biosynthesis, metabolism, and action of oxylipins, especially jasmonates, has dramatically improved. Additional mechanistic insights into the action of enzymes and insights into signaling pathways have been deepened for jasmonates. For other oxylipins, such as the hydroxy fatty acids, individual signaling properties and cross talk between different oxylipins or even with additional phytohormones have recently been described. This review summarizes recent understanding of the biosynthesis, regulation, and function of oxylipins.
Publikation

Wasternack, C.; Strnad, M.; Jasmonates: News on Occurrence, Biosynthesis, Metabolism and Action of an Ancient Group of Signaling Compounds Int. J. Mol. Sci. 19, 2539, (2018) DOI: 10.3390/ijms19092539

Jasmonic acid (JA) and its related derivatives are ubiquitously occurring compounds of land plants acting in numerous stress responses and development. Recent studies on evolution of JA and other oxylipins indicated conserved biosynthesis. JA formation is initiated by oxygenation of α-linolenic acid (α-LeA, 18:3) or 16:3 fatty acid of chloroplast membranes leading to 12-oxo-phytodienoic acid (OPDA) as intermediate compound, but in Marchantiapolymorpha and Physcomitrellapatens, OPDA and some of its derivatives are final products active in a conserved signaling pathway. JA formation and its metabolic conversion take place in chloroplasts, peroxisomes and cytosol, respectively. Metabolites of JA are formed in 12 different pathways leading to active, inactive and partially active compounds. The isoleucine conjugate of JA (JA-Ile) is the ligand of the receptor component COI1 in vascular plants, whereas in the bryophyte M. polymorpha COI1 perceives an OPDA derivative indicating its functionally conserved activity. JA-induced gene expressions in the numerous biotic and abiotic stress responses and development are initiated in a well-studied complex regulation by homeostasis of transcription factors functioning as repressors and activators.
Publikation

Wasternack, C.; Hause, B.; A Bypass in Jasmonate Biosynthesis – the OPR3-independent Formation Trends Plant Sci. 23, 276-279, (2018) DOI: 10.1016/j.tplants.2018.02.011

For the first time in 25 years, a new pathway for biosynthesis of jasmonic acid (JA) has been identified. JA production takes place via 12-oxo-phytodienoic acid (OPDA) including reduction by OPDA reductases (OPRs). A loss-of-function allele, opr3-3, revealed an OPR3-independent pathway converting OPDA to JA.
Publikation

Ortel, B.; Atzorn, R.; Hause, B.; Feussner, I.; Miersch, O.; Wasternack, C.; Jasmonate-induced gene expression of barley (Hordeum vulgare) leaves - the link between jasmonate and abscisic acid Plant Growth Regul. 29, 113-122, (1999) DOI: 10.1023/A:1006212017458

In barley leaves a group of genes is expressed in response to treatment with jasmonates and abscisic acid (ABA) [21]. One of these genes coding for a jasmonate-induced protein of 23 kDa (JIP-23) was analyzed to find out the link between ABA and jasmonates by recording its expression upon modulating independently, the endogenous level of both of them. By use of inhibitors of JA synthesis and ABA degradation, and the ABA-deficient mutant Az34, as well as of cultivar-specific differences, it was shown that endogenous jasmonate increases are necessary and sufficient for expression of this gene. The endogenous rise of ABA did not induce synthesis of JIP-23, whereas exogenous ABA did not act via jasmonates. Different signalling pathways are suggested and discussed.
Publikation

Miersch, O.; Kramell, R.; Parthier, B.; Wasternack, C.; Structure–activity relations of substituted, deleted or stereospecifically altered jasmonic acid in gene expression of barley leaves Phytochemistry 50, 353-361, (1999) DOI: 10.1016/S0031-9422(98)00597-4

Jasmonic acid and 66 structurally related compounds were tested to find the structural requirements which induce the expression of jasmonate-responsive genes in barley. An intact cyclopentanone ring as well as a pentenyl side chain exhibiting only minor alterations are necessary for this activity. The (−)-enantiomeric and the (+)-7-iso-enantiomeric structure increase activity of jasmonoyl compounds.
Publikation

Miersch, O.; Porzel, A.; Wasternack, C.; Microbial conversion of jasmonates - hydroxylations by Aspergillus niger Phytochemistry 50, 1147-1152, (1999) DOI: 10.1016/S0031-9422(98)00698-0

Aspergillus niger is able to hydroxylate the pentenyl side chain of (−)-jasmonic acid (JA) leading to (11S)- (−)-hydroxy-JA/ (11R)- (−)-hydroxy-JA (2:1) and (−)-11,12-didehydro-JA. Methyl (−)-jasmonate (JA-Me) is converted upon hydrolysis. During prolonged cultivation or at non-optimized isolation procedures, the 11-hydroxy- (9Z)-pentenyl side chain may isomerize to (10E)-9-hydroxy- and (9E)-11-hydroxy-compounds by allylic rearrangement. The fungus hydroxylates (±)-9,10-dihydro-JA at position C-11 into 11j-hydroxy-9,10-dihydro-JA. As JA-Me, the methyl dihydro-JA is hydroxylated only upon hydrolysis into the free acid.
Publikation

Miersch, O.; Bohlmann, H.; Wasternack, C.; Jasmonates and related compounds from Fusarium oxysporum Phytochemistry 50, 517-523, (1999) DOI: 10.1016/S0031-9422(98)00596-2

The culture filtrate of Fusarium oxysporum f sp matthiolae was inspected on the occurrence of jasmonates and related compounds. Among compounds described for the first time of biological origin are 7-iso-cucurbic acid, (1S,2S)- and (1S,2R)-3-oxo-2-pentylcyclopentane-1-butyric acid, (1S,2S)- and (1S,2R)-3-oxo-2-(2Z-pentenyl)cyclopentane-1-hexanoic acid, (1S,2S)- and (1S,2R)-3-oxo-2-pentylcyclopentane-1-hexanoic acid, (1S,2S)-3-oxo-2-(2Z-pentenyl)cyclopentane-1-octanoic acid, (1S,2S)-3-oxo-2-pentylcyclopentane-1-octanoic acid and N-[9,10-dihydro-7-iso-jasmonoyl]-(S)-isoleucine. The following metabolites were identified for the first time for this fungus: (−)-Jasmonic acid, 9,10-dihydrojasmonic acid and N-[(−)-jasmonoyl-(S)]-isoleucine were major constituents of the culture filtrate, whereas as minor metabolites occurred N-[9,10-dihydrojasmonoyl]-(S)-isoleucine, cucurbic acid and 3-oxo-2-(2Z-pentenyl)cyclopentane-1-butyric acid, 3-oxo-2-(2Z-pentenyl)cyclopentane-1-octanoic acid and 3-oxo-2-pentylcyclopentane-1-octanoic acid. All cyclopentanones found carried a cis- or trans-attached side chain. Didehydro-jasmonates, hydroxylated jasmonates or 12-oxophytodienoic acid could not be detected in the culture filtrate.
Publikation

Kramell, R.; Miersch, O.; Schneider, G.; Wasternack, C.; Liquid chromatography of jasmonic acid amine conjugates Chromatographia 49, 42-46, (1999) DOI: 10.1007/BF02467185

Racemic jasmonic acid (3R,7R/3S,7S)-(±)-JA) was chemically conjugated with different biogenic amines originating from aliphatic and aromatic α-amino acids by decarboxylation. The resulting isomeric compounds were subjected to reversed-phase high-performance liquid chromatography (HPLC) and to HPLC on the chiral stationary phases Chiralpak AS and Nucleodex β-PM. Under reversed-phase conditions, all the homologous amine derivatives tested could be separated from each other except the JA-conjugates containing 2-phenyl-ethylamine and 3-methylbutylamine. On both chiral supports the (3R,7R)-(−)-JA conjugates eluted earlier than those of the enantiomeric counterpart (3S,7S)-(+)-JA. On Chiralpak AS all the isomers studied could be separated to baseline with a mobile phase containingn-hexane and 2-propanol. The calculated resolution factors were between 1.80 and 4.17. The pairs of isomers were also chromatographed on the cyclodextrin stationary phase Nucleodex β-PM with methanol-triethylammonium acetate buffer as mobile phase. Under these conditions resolution factors were between 0.74 and 1.29. The individual isomers were chiroptically characterized by measurement of their circular dichroism.
Publikation

Kramell, R.; Porzel, A.; Miersch, O.; Schneider, G.; Wasternack, C.; Chromatographic resolution of peptide-like conjugates of jasmonic acid and of cucurbic acid isomers J. Chromatogr. A 847, 103-107, (1999) DOI: 10.1016/S0021-9673(99)00335-0

The chiral separation of peptide-like conjugates of jasmonic acid and of cucurbic acid isomers was investigated by liquid chromatography on Chiralpak AS and Nucleodex β-PM. The retention sequences reflect distinct chromatographic properties with respect to the chirality of the jasmonic acid part or of the cucurbic acid isomers. The chromatographic behaviour of the amide conjugates on a reversed-phase C18 column provides evidence for the resolution of diastereomeric conjugates depending on the chirality of both constituents of the conjugate molecule. The chromatographic procedures are suitable for the analytical and preparative separation of such conjugates.
Publikation

Kenton, P.; Mur, L. A. J.; Atzorn, R.; Wasternack, C.; Draper, J.; (—)-Jasmonic Acid Accumulation in Tobacco Hypersensitive Response Lesions Mol. Plant Microbe Interact. 12, 74-78, (1999) DOI: 10.1094/MPMI.1999.12.1.74

Tobacco infected with Pseudomonas syringae pv. phaseolicola undergoes a hypersensitive response (HR). Jasmonic acid (JA) accumulated within the developing lesion 3 to 9 h after infection and this accumulation preceded protein loss, cell death, and malondialdehyde accumulation. Accumulating JA consisted largely of the (—)-JA stereoisomer and was essentially restricted to the HR lesion.
  • Die Leibniz-Gemeinschaft
  • Digitalisierung in der Landwirtschaft
  • Martin-Luther Universität Halle
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