Bacterial metabolism of alpha-pinene: pathway from alpha-pinene oxide to acyclic metabolites in Nocardia sp. strain P18.3.
Over 20 gram-positive bacteria were isolated by elective culture with (+/-)-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. 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.
Griffiths
E T
ET
Department of Biochemistry, University College of Wales, Aberystwyth, Dyfed, Great Britain.
Bociek
S M
SM
Harries
P C
PC
Jeffcoat
R
R
Sissons
D J
DJ
Trudgill
P W
PW
D000446:Aldehyde-Lyases / Q000378:metabolism*; D000081008:Bicyclic Monoterpenes; D001711:Biotransformation; D004591:Electrophoresis, Polyacrylamide Gel; D007700:Kinetics; D039821:Monoterpenes; D009615:Nocardia / Q000378:metabolism*; D010101:Oxygen Consumption; D013729:Terpenes / Q000378:metabolism*
D000081008:Bicyclic Monoterpenes; D039821:Monoterpenes; D013729:Terpenes; C053997:2-pinene oxide; D000446:Aldehyde-Lyases; C053996:alpha-pinene oxide lyase; C005451:alpha-pinene