Microbial conversion of jasmonates-hydroxylations by Aspergillus niger.
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 11 xi-hydroxy-9,10- dihydro-JA. As JA-ME, the methyl dihydro-JA is hydroxylated only upon hydrolysis into the free acid.
Miersch
O
O
Institut für Pflanzenbiochemie, Halle/Saale, Germany. omiersch@ipb.uni-halle.de
Porzel
A
A
Wasternack
C
C
D001234:Aspergillus niger / Q000378:metabolism*; D001711:Biotransformation; D003517:Cyclopentanes / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D006900:Hydroxylation; D019906:Nuclear Magnetic Resonance, Biomolecular; D054883:Oxylipins; D010937:Plant Growth Regulators / Q000378:metabolism
D003517:Cyclopentanes; D054883:Oxylipins; D010937:Plant Growth Regulators; C011006:jasmonic acid