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Discovery and mechanism of intestinal bacteria in enzymatic cleavage of C–C glycosidic bonds

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Abstract

C-Glycosides, a special type of glycoside, are frequently distributed in many kinds of medicinal plants, such as puerarin and mangiferin, showing various and significant bioactivities. C-Glycosides are usually characterized by the C–C bond that forms between the anomeric carbon of sugar moieties and the carbon atom of aglycon, which is usually resistant against acidic hydrolysis and enzymatic treatments. Interestingly, C-glycosides could be cleaved by several intestinal bacteria, but whether the enzymatic cleavage of C–C glycosidic bond is reduction or hydrolysis has been controversial; furthermore, whether existence of a “C-glycosidase” directly catalyzing the cleavage is not clear. Here we review research advances about the discovery and mechanism of intestinal bacteria in enzymatic cleavage of C–C glycosidic bond with an emphasis on the identification of enzymes manipulation the deglycosylation. Finally, we give a brief conclusion about the mechanism of C-glycoside deglycosylation and perspectives for future study in this field.

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Funding

This work was financially supported by the National Key R&D Program of China (2017YFE0103100), the National Natural Science Foundation of China (No. 81773628 and No. 81741165), and the National 111 Project (No. D17012).

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Author notes

  1. Bin Wei and Ya-Kun Wang contributed equally to this work.

Authors and Affiliations

  1. Key Laboratory of Marine Ecosystem and Biogeochemistry, State Oceanic Administration & Second Institute of Oceanography, Ministry of Natural Resources, 310012, Hangzhou, People’s Republic of China

    Bin Wei, Yue-Hong Wu & Xue-Wei Xu

  2. College of Pharmaceutical Science & Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, 310014, Hangzhou, People’s Republic of China

    Bin Wei, Ya-Kun Wang, Wen-Hui Qiu, Si-Jia Wang & Hong Wang

  3. Center for Human Nutrition, David Geffen School of Medicine, University of California, Rehabilitation Building 32-21, 1000 Veteran Avenue, Los Angeles, CA, 90024, USA

    Si-Jia Wang

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  1. Bin Wei
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  2. Ya-Kun Wang
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  3. Wen-Hui Qiu
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  4. Si-Jia Wang
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Correspondence to Xue-Wei Xu or Hong Wang.

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Wei, B., Wang, YK., Qiu, WH. et al. Discovery and mechanism of intestinal bacteria in enzymatic cleavage of C–C glycosidic bonds. Appl Microbiol Biotechnol 104, 1883–1890 (2020). https://doi.org/10.1007/s00253-019-10333-z

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  • DOI: https://doi.org/10.1007/s00253-019-10333-z

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