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Characterization of the catabolic pathway for a phenylcoumaran-type lignin-derived biaryl in Sphingobium sp. strain SYK-6

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Abstract

Sphingobium sp. strain SYK-6 is capable of degrading various lignin-derived biaryls. We determined the catabolic pathway of a phenylcoumaran-type compound, dehydrodiconiferyl alcohol (DCA) in SYK-6, and identified some of the DCA catabolism genes. In SYK-6 cells, the alcohol group of DCA was oxidized to the carboxyl group, first at the B-ring side chain and then at the A-ring side chain. The resultant metabolite was degraded to 5-formylferulate and vanillin through the decarboxylation and the Cα–Cβ cleavage of the A-ring side chain. Based on the DCA catabolic pathway, alcohol dehydrogenase (ADH) and aldehyde dehydrogenase (ALDH) genes are thought to be involved in the conversion of DCA into an aldehyde intermediate (DCA-L) and the conversion of DCA-L into a carboxylic acid intermediate (DCA-C), respectively. SLG_05620 and SLG_24930, which belong to quinohemoprotein ADH and aryl ADH, respectively, were isolated as the genes responsible for the oxidation of DCA. In addition to these genes, multiple genes similar to SLG_05620 and SLG_24930 were found to confer DCA oxidation activities on Escherichia coli cells. In order to identify the DCA-L dehydrogenase genes, the DCA-L oxidation activities of the SYK-6 gene products of putative twenty-one ALDH genes were examined. Significant activities were observed in the four ALDH gene products, including the SLG_27910 product, which showed the highest activity. The disruption of SLG_27910 caused a decreased conversion of DCA-L, suggesting that SLG_27910 plays an important role in the DCA-L oxidation. In conclusion, no specific gene seems to be solely responsible for the conversion of DCA and DCA-L, however, the multiple genes encoding quinohemoprotein ADH and aryl ADH genes, and four ALDH genes are probably involved in the conversion processes.

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Acknowledgments

This work was supported in part by the “Development of Preparatory Basic Bioenergy Technology” grant from The New Energy and Industrial Technology Development Organization (NEDO) of Japan and the “Advanced Low Carbon Technology Research and Development Program” grant from The Japan Science and Technology Agency (JST).

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Authors and Affiliations

  1. Department of Bioengineering, Nagaoka University of Technology, Nagaoka, Niigata, 940-2188, Japan

    Kenji Takahashi, Naofumi Kamimura, Daisuke Kasai, Masao Fukuda & Eiji Masai

  2. Forestry and Forest Products Research Institute, Tsukuba, Ibaraki, 305-8687, Japan

    Shojiro Hishiyama

  3. Department of Environmental Engineering and Green Technology, Malaysia-Japan International Institute of Technology, Universiti Teknologi Malaysia, 54100, Kuala Lumpur, Malaysia

    Hirofumi Hara

  4. College of Bioresource Sciences, Nihon University, Fujisawa, Kanagawa, 252-0880, Japan

    Yoshihiro Katayama

  5. Graduate School of Bio-Applications and Systems Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo, 184-8588, Japan

    Shinya Kajita

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  1. Kenji Takahashi
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  2. Naofumi Kamimura
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  3. Shojiro Hishiyama
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  4. Hirofumi Hara
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  5. Daisuke Kasai
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  6. Yoshihiro Katayama
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  7. Masao Fukuda
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  8. Shinya Kajita
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  9. Eiji Masai
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Correspondence to Eiji Masai.

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Takahashi, K., Kamimura, N., Hishiyama, S. et al. Characterization of the catabolic pathway for a phenylcoumaran-type lignin-derived biaryl in Sphingobium sp. strain SYK-6. Biodegradation 25, 735–745 (2014). https://doi.org/10.1007/s10532-014-9695-0

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  • DOI: https://doi.org/10.1007/s10532-014-9695-0

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