Creation of bioactive non-natural flavonoids via combinatorial prenylation–glycosylation cascades

References

[1] Saha S, Prinsa , Kawsar SMA. Natural flavonoids as primary amoebic meningoencephalitis inhibitor: virtual screening, molecular docking, MD simulation, MMPBSA, density functional theory, principal component, and gibbs free energy landscape analyses. Chem Biodiversity. 2024; 22: 1–15.

[2] Karak P. Biological activities of flavonoids: an overview. Int J Pharm Sci Res. 2019; 10: 1567–1574.

[3] Chen S, Wang X, Cheng Y, Gao H, Chen X. A review of classification, biosynthesis, biological activities and potential applications of flavonoids. Molecules. 2023; 28: 4982.

[4] Maideen NMP, Hadda TB, Almalki FA, Laarousi H, Soliman SSM, Kawsar SMA. Black seeds (Nigella sativa) for the management of dengue viral disease: insight into the evidence and POM analyses for the identification of antiviral pharmacophore sites: a review. J Med Herb Ethnomed. 2023; 14: 19–36.

[5] Karim T, Almatarneh MH, Rahman S, Alodhayb AN, Albrithen H, Hossain MM, et al. In silico prediction of antibacterial activity of quinolone derivatives. ChemistrySelect. 2024; 9: 1–20.

[6] Uçar K, Göktaş Z. Biological activities of naringenin: a narrative review based on in vitro and in vivo studies. Nutr Res. 2023; 119: 43–55.

[7] Gao HY, Liu Y, Tan FF, Zhu LW, Jia KZ, Tang YJ. The advances and challenges in enzymatic C-glycosylation of flavonoids in plants. Curr Pharm Des. 2022; 28: 1466–1479.

[8] Mukai R. Prenylation enhances the biological activity of dietary flavonoids by altering their bioavailability. Biosci Biotechnol Biochem. 2018; 82: 207–215.

[9] Lv HW, Wang QL, Luo M, Zhu MD, Liang HM, Li WJ, et al. Phytochemistry and pharmacology of natural prenylated flavonoids. Arch Pharmacal Res. 2023; 46: 207–272.

[10] Wang H, Wu Y, Liu Y, Zhao L, Pei J. Screening and characterizing flavone synthases and its application in biosynthesizing vitexin from naringenin by a one-pot enzymatic cascade. Enzyme Microb Technol. 2022; 160:110101.

[11] Zhang Z, He Y, Huang Y, Ding L, Chen L, Liu Y, et al. Development and optimization of an in vitro multienzyme synthetic system for production of kaempferol from naringenin. J Agricult Food Chem. 2018; 66: 8272–8279.

[12] Sun H, Liu Z, Zhao H, Ang EL. Recent advances in combinatorial biosynthesis for drug discovery. Drug Des Devel Ther. 2015; 9: 823–833.

[13] Li H, Ma W, Lyv Y, Gao S, Zhou J. Glycosylation modification enhances (2S)-naringenin production in Saccharomyces cerevisiae. ACS Synth Biol. 2022; 11: 2339–2347.

[14] Dai X, Shi X, Yang C, Zhao X, Zhuang J, Liu Y, et al. Two UDP-glycosyltransferases catalyze the biosynthesis of bitter flavonoid 7-O-neohesperidoside through sequential glycosylation in tea plants. J Agricult Food Chem. 2022; 70: 2354–2365.

[15] Deng Y, Yang P, Zhang Q, Wu Q, Feng L, Shi W, et al. Genomic insights into the evolution of flavonoid biosynthesis and O-methyltransferase and glucosyltransferase in Chrysanthemum indicum. Cell Rep. 2024; 43:113725.

[16] Kim JH, Kim BG, Park Y, Ko JH, Lim CE, Lim J, et al. Characterization of flavonoid 7-O-glucosyltransferase from Arabidopsis thaliana. Biosci Biotechnol Biochem. 2006; 70: 1471–1477.

[17] Thapa SB, Pandey RP, Bashyal P, Yamaguchi T, Sohng JK. Cascade biocatalysis systems for bioactive naringenin glucosides and quercetin rhamnoside production from sucrose. Appl Microbiol Biotechnol. 2019; 103: 7953–7969.

[18] Yu X, Li SM. Prenylation of flavonoids by using a dimethylallyltryptophan synthase, 7-DMATS, from Aspergillus fumigatus. ChemBioChem. 2011; 12: 2280–2283.

[19] Zhou K, Yu X, Xie X, Li SM. Complementary flavonoid prenylations by fungal indole prenyltransferases. J Nat Prod. 2015; 78: 2229–2235.

[20] Zhang X, Yao W, Tang Y, Ye J, Niu T, Yang L, et al. Coupling the isopentenol utilization pathway and prenyltransferase for the biosynthesis of licoflavanone in recombinant Escherichia coli. J Agricult Food Chem. 2024; 72: 15832–15840.

RIGHTS & PERMISSIONS

2026 The Author(s). mLife published by John Wiley & Sons Australia, Ltd on behalf of Institute of Microbiology, Chinese Academy of Sciences.