Miersch O, Porzel A, Wasternack C
Institut für Pflanzenbiochemie, Halle/Saale, Germany.
Phytochemistry. 1999 Apr;50(7):1147-52. 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 11 xi-hydroxy-9,10- dihydro-JA. As JA-ME, the methyl dihydro-JA is hydroxylated only upon hydrolysis into the free acid.
黑曲霉能够使（-）-茉莉酸（JA）的戊烯基侧链发生羟基化反应，生成（11S）-（-）-羟基-JA/（11R）-（-）-羟基-JA（2:1）和（-）-11,12-二脱氢-JA。（-）-茉莉酸甲酯（JA-Me）在水解后会发生转化。在长时间培养或非优化的分离过程中，11-羟基-（9Z）-戊烯基侧链可能通过烯丙基重排异构化为（10E）-9-羟基-和（9E）-11-羟基化合物。该真菌将（±）-9,10-二氢-JA在C-11位羟基化为11ξ-羟基-9,10-二氢-JA。与JA-ME一样，二氢-JA甲酯仅在水解为游离酸时才会发生羟基化反应。
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