Identification of syn- and anti-anethole-2,3-epoxides in the metabolism of trans-anethole by the newly isolated bacterium Pseudomonas putida JYR-1.
Bacterial strain JYR-1, which utilizes high concentrations (up to 100 mM) of trans-anethole as the sole source of carbon and energy, was isolated from soil. It grew to OD(600)(nm) = 2.6 with a doubling time of 8 h when grown on 20 mM trans-anethole. Strain JYR-1 was identified as Pseudomonas putida based on the partial gene sequence of its 16S rDNA. Elution profiles of culture extracts were examined by high-performance liquid chromatography and showed that four metabolites were produced from the bacterial culture containing trans-anethole that were not detected in control experiments. LC-MS analysis showed molecular weights of 138.2, 164.5, 164.3, and 152.3. The metabolites with molecular weights at 152.3 and 138.2 were confirmed to be p-anisic acid and p-hydroxybenzoic acid, respectively, when compared with HPLC retention times and molecular weights of authentic compounds. The metabolites with molecular weights at 164.5 and 164.3 were further analyzed by NMR and were proved to be stereoisomer syn- and anti-anethole epoxides. Therefore, strain JYR-1 most likely initiates the metabolism of trans-anethole through the formation of epoxides on the propene group of the compound.
Ryu
Jiyoung
J
Department of Environmental Science and Engineering and Water Reuse Technology Center, Gwangju Institute of Science and Technology, Gwangju, Korea.
Seo
Jiyoung
J
Lee
Youngshim
Y
Lim
Yoongho
Y
Ahn
Joong-Hoon
JH
Hur
Hor-Gil
HG
D000081248:Allylbenzene Derivatives; D000840:Anisoles / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D004269:DNA, Bacterial / Q000737:chemistry; D004852:Epoxy Compounds / Q000032:analysis* / Q000378:metabolism*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D016958:Pseudomonas putida / Q000145:classification / Q000235:genetics / Q000378:metabolism*; D012336:RNA, Ribosomal, 16S / Q000235:genetics; D012988:Soil Microbiology
D000081248:Allylbenzene Derivatives; D000840:Anisoles; D004269:DNA, Bacterial; D004852:Epoxy Compounds; D012336:RNA, Ribosomal, 16S; C006578:anethole