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Natural Product Glycosylation: Biocatalytic Synthesis of Quercetin-3,4′-O-diglucoside

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Abstract

Flavonoids have gained much attention for their proposed positive effects for human health. Glycosylation is a significant method for the structural modification of various flavanols, resulting in glycosides with increased solubility, stability, and bioavailability compared with the corresponding aglycone. Natural product glycosylation by using enzymes has emerged as a topic of interest as it offers a sustainable and economical alternative source so as to address supply scalability limitations associated with plant-based production. Quercetin-3,4′-O-diglucoside, as one of the major but trace bioactive flavonoids in onion (Allium cepa), is superior or at least equal to quercetin aglycone in its bioavailability. In the present study, the onion-derived enzyme, UGT73G1, coupled with sucrose synthase, StSUS1, from Solanum tuberosum formed a circulatory system to produce quercetin-3,4′-O-diglucoside from quercetin, which preferred sucrose as a sugar donor and quercetin as a sugar acceptor. The optimal conditions were determined in order to increase the production of quercetin-3,4′-O-diglucoside. The maximum concentration of quercetin-3,4′-O-diglucoside achieved in a 10-mL reaction was 427.11 mg/L, from the conversion of 1 g/L of quercetin for 16 h at 40 °C and pH 7.2.

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Funding

This work was financially funded by the NSFC (21878155), PAPD, Qing Lan Project of Jiangsu Universities, Six Talent Peaks Project in Jiangsu Province, and Jiangsu Synergetic Innovation Center for Advanced Bio-Manufacture.

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Authors and Affiliations

  1. College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing, 211800, China

    Ping Sun, Ruxin Cai, Liangliang Chen, Yan Li, Honghua Jia, Ming Yan & Kequan Chen

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  1. Ping Sun
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  2. Ruxin Cai
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  3. Liangliang Chen
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  4. Yan Li
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Contributions

RC, PS, and YL conceived and designed the study. RC, PS, and LC performed the experiments and analyzed the data. PS and RC wrote the paper. YL, HJ, KC, and MY reviewed and edited the manuscript. All authors read and approved the manuscript.

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Correspondence to Yan Li.

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

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The authors declare that they have no competing interests.

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Ping Sun and Ruxin Cai are contributed to the work equally and should be regarded as co-first authors.

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Sun, P., Cai, R., Chen, L. et al. Natural Product Glycosylation: Biocatalytic Synthesis of Quercetin-3,4′-O-diglucoside. Appl Biochem Biotechnol 190, 464–474 (2020). https://doi.org/10.1007/s12010-019-03103-0

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