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

  • Bin Wei
  • Ya-Kun Wang
  • Wen-Hui Qiu
  • Si-Jia Wang
  • Yue-Hong Wu
  • Xue-Wei XuEmail author
  • Hong WangEmail author


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.


C-glycosides C–C glycosidic bond Puerarin Deglycosylation Intestinal bacteria 


Funding information

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).

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Ethical approval

This article does not contain any studies with human participants or animals performed by any of the authors.


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Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Key Laboratory of Marine Ecosystem and BiogeochemistryState Oceanic Administration & Second Institute of Oceanography, Ministry of Natural ResourcesHangzhouPeople’s Republic of China
  2. 2.College of Pharmaceutical Science & Collaborative Innovation Center of Yangtze River Delta Region Green PharmaceuticalsZhejiang University of TechnologyHangzhouPeople’s Republic of China
  3. 3.Center for Human Nutrition, David Geffen School of MedicineUniversity of CaliforniaLos AngelesUSA

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