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Microbial Catalyzed Regio-Selective Demethylation of Colchicine by Streptomyces griseus ATCC 13273

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Abstract

Colchicinoids and their derivatives are of great importance in pharmaceutical applications, and colchicine is usually used as the first choice for the treatment of gout. To expand the structural diversities and clinical application of colchicinoids, many attempts have been established for the derivatives with better activity or less toxicity. Herein, in this paper, we report a direct microbial transformation of colchicine into 2-O-demethyl-colchicine (M1) and 3-O-demethl-colchicine (M2) by Streptomyces griseus ATCC 13273. It is noteworthy that when DMF was used as co-solvent, the yield of M1 and M2 could reach up to 51 and 31%, respectively. All the structures of the metabolites were elucidated unambiguously by ESI-MS, 1H–NMR, 13C–NMR, and 2D–NMR spectroscopy.

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Acknowledgements

This work was supported by the Program for New Century Excellent Talents in University. Thanks also given to the “111 Project” from the Ministry of Education of China, the Fundamental Research Funds for the Central Universities (JKZ2011017), and the scientific and innovation research of college graduate in Jangsu province (CXLX11_0788).

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Authors and Affiliations

  1. State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, Jiangsu, 210009, China

    Chao Zhang, Xian Sun, Shao Hua Xu & Jian Zhang

  2. Jiangsu Key Laboratory of TCM Evaluation and Translational Research, China Pharmaceutical University, Nanjing, Jiangsu, 211198, China

    Bo Yang Yu

  3. State Key Laboratory of Natural Medicines, China Pharmaceutical University, 639 Long Mian Avenue, Jiang Ning, Nanjing, 211198, China

    Jian Zhang

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  1. Chao Zhang
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  2. Xian Sun
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Correspondence to Jian Zhang.

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Zhang, C., Sun, X., Xu, S.H. et al. Microbial Catalyzed Regio-Selective Demethylation of Colchicine by Streptomyces griseus ATCC 13273. Appl Biochem Biotechnol 183, 1026–1034 (2017). https://doi.org/10.1007/s12010-017-2480-x

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  • DOI: https://doi.org/10.1007/s12010-017-2480-x

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