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Conversion of nornicotine to 6-hydroxy-nornicotine and 6-hydroxy-myosmine by Shinella sp. strain HZN7

  • Applied genetics and molecular biotechnology
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Abstract

Nornicotine is a natural alkaloid produced by plants in the genus Nicotiana and is structurally related to nicotine. Importantly, nornicotine is the direct precursor of tobacco-specific nitrosamine N′-nitrosonornicotine, which is a highly potent human carcinogen. Microbial detoxification and degradation of nicotine have been well characterized; however, until now, there has been no information on the molecular mechanism of nornicotine degradation. In this study, we demonstrate the transformation of nornicotine by the nicotine-degrading strain Shinella sp. HZN7. Three transformation products were identified as 6-hydroxy-nornicotine, 6-hydroxy-myosmine, and 6-hydroxy-pseudooxy-nornicotine by UV spectroscopy, high-resolution mass spectrometry, nuclear magnetic resonance, and Fourier transform-infrared spectroscopy analyses. The two-component nicotine dehydrogenase genes nctA1 and nctA2 were cloned, and their product, NctA, was confirmed to be responsible for the conversion of nornicotine into 6-hydroxy-nornicotine as well as nicotine into 6-hydroxy-nicotine. The 6-hydroxy-nicotine oxidase, NctB, catalyzed the oxidation of 6-hydroxy-nornicotine to 6-hydroxy-myosmine, and it spontaneously hydrolyzed into 6-hydroxy-pseudooxy-nornicotine. However, 6-hydroxy-pseudooxy-nornicotine could not be further degraded by strain HZN7. This study demonstrated that nornicotine is partially transformed by strain HZN7 via nicotine degradation pathway.

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Acknowledgments

This work was supported by the National Natural Science Foundation of China (Nos. 31500082 and 31422003), China Postdoctoral Science Foundation (No. 2014 M560495), and the Program for New Century Excellent Talents in University (NCET-13-0861).

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Authors and Affiliations

  1. Key Laboratory of Agricultural Environmental Microbiology, Ministry of Agriculture, College of Life Sciences, Nanjing Agricultural University, Nanjing, 210095, China

    Jiguo Qiu, Na Li, Youjian Yang & Jian He

  2. College of Life Sciences, Zhejiang University, Hangzhou, 310058, China

    Zhenmei Lu

  3. College of Environment, Zhejiang University of Technology, Hangzhou, 310014, China

    Yun Ma

  4. College of Environmental and Resource Sciences, Zhejiang University, Hangzhou, 310058, China

    Lili Niu & Weiping Liu

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  1. Jiguo Qiu
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Correspondence to Jian He.

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Qiu, J., Li, N., Lu, Z. et al. Conversion of nornicotine to 6-hydroxy-nornicotine and 6-hydroxy-myosmine by Shinella sp. strain HZN7. Appl Microbiol Biotechnol 100, 10019–10029 (2016). https://doi.org/10.1007/s00253-016-7805-0

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  • DOI: https://doi.org/10.1007/s00253-016-7805-0

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