Identification of syn- and anti-Anethole-2,3-epoxides in the Metabolism of trans-Anethole by the Newly Isolated Bacterium Pseudomonas putida JYR-1

详细信息    查看全文

• 作者：Jiyoung Ryu ; Jiyoung Seo ; Youngshim Lee ; Yoongho Lim ; Joong-Hoon Ahn ; and Hor-Gil Hur
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2005
• 出版时间：July 27, 2005
• 年：2005
• 卷：53
• 期：15
• 页码：5954 - 5958
• 全文大小：85K
• 年卷期：v.53,no.15(July 27, 2005)
• ISSN：1520-5118

文摘

Bacterial strain JYR-1, which utilizes high concentrations (up to 100 mM) of trans-anethole as thesole source of carbon and energy, was isolated from soil. It grew to OD_600nm = 2.6 with a doublingtime of 8 h when grown on 20 mM trans-anethole. Strain JYR-1 was identified as Pseudomonasputida based on the partial gene sequence of its 16S rDNA. Elution profiles of culture extracts wereexamined by high-performance liquid chromatography and showed that four metabolites wereproduced from the bacterial culture containing trans-anethole that were not detected in controlexperiments. LC-MS analysis showed molecular weights of 138.2, 164.5, 164.3, and 152.3. Themetabolites with molecular weights at 152.3 and 138.2 were confirmed to be p-anisic acid andp-hydroxybenzoic acid, respectively, when compared with HPLC retention times and molecular weightsof authentic compounds. The metabolites with molecular weights at 164.5 and 164.3 were furtheranalyzed 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 epoxideson the propene group of the compound.Keywords: trans-Anethole; Pseudomonas; flavor; phenylpropanoid; biotransformation