Structure Identification: |
Journal of bacteriology,1987,169(11):4972-9. | Bacterial metabolism of alpha-pinene: pathway from alpha-pinene oxide to acyclic metabolites in Nocardia sp. strain P18.3.[Reference: WebLink] | METHODS AND RESULTS: Over 20 gram-positive bacteria were isolated by elective culture with (+/-)-alpha-pinene((+)-alpha-Pinene/(-)-alpha-Pinene) as the sole carbon source. One of these strains, Nocardia sp. strain P18.3, was selected for detailed study. alpha-Pinene-grown cells oxidized, without lag, alpha-pinene, alpha-pinene oxide (epoxide), and the cis and trans isomers of 2-methyl-5-isopropylhexa-2,5-dienal. No other tested terpene was oxidized at a significant rate. alpha-Pinene was not metabolized by cell extracts in the presence or absence of NADH or NADPH. Cell extracts catalyzed a rapid decyclization of alpha-pinene oxide, in the absence of added cofactors, with the formation of cis-2-methyl-5-isopropylhexa-2,5-dienal. Further oxidation of the aldehyde to the corresponding acid occurred in the presence of NAD. Both activities were induced by growth with alpha-pinene.
CONCLUSIONS:
A rapid, nonenzymic transformation of the cis aldehyde into the trans isomer occurred in glycine buffer. The trans isomer was also a substrate for the NAD-linked aldehyde dehydrogenase.
The distribution of the alpha-pinene oxide lyase in alpha-pinene-utilizing Pseudomonas spp. was also investigated and was compatible with the two alternative ring-cleavage sequences that have been proposed on the basis of accumulated metabolites. |
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