Journal of Microbiology and Biotechnology
The Korean Society for Microbiology and Biotechnology publishes the Journal of Microbiology and Biotechnology.

2020 ; Vol.30-1: 11~20

AuthorRubin Thapa Magar, Jae Kyung Sohng
Place of dutyDepartment of Life Science and Biochemical Engineering, Sun Moon University, Republic of Korea
TitleA Review on Structure, Modifications and Structure-Activity Relation of Quercetin and Its Derivatives
PublicationInfo J. Microbiol. Biotechnol.2020 ; Vol.30-1
AbstractQuercetin and its derivatives are important metabolites that belong to the flavonol class of flavonoids. Quercetin and some of the conjugates have been approved by the FDA for human use. They are widely distributed among plants and have various biological activities, such as being anticancer, antiviral, and antioxidant. Hence, the biosynthesis of novel derivatives is an important field of research. Glycosylation and methylation are two important modification strategies that have long been used and have resulted in many novel metabolites that are not present in natural sources. A strategy for modifying quercetin in E. coli by means of glycosylation, for example, involves overexpressing respective glycosyltransferases (GTs) in the host and metabolic engineering for increasing nucleoside diphosphate sugar (NDP sugar). Still others have used microorganisms other than E. coli, such as Streptomyces sp., for the biotransformation process. The overall study of the structural activity relationship has revealed that modification of some residues in quercetin decreased one activity but increased others. This review summarizes all of the information mentioned above.
Full-Text
Key_wordQuercetin, glycosylation, methylation, biotransformation
References
  1. Nemeth K, Piskuła MK. 2007. Food content, processing, absorption and metabolism of onion flavonoids. Crit. Rev. Food Sci. Nutr. 47: 397-409.
    Pubmed CrossRef
  2. Berardini N, Fezer R, Conrad J, Beifuss U, Carle R, Schieber A. 2005. Screening of mango (Mangifera indica L.) cultivars for their contents of flavonol O- and xanthone C-glycosides, anthocyanins and pectin. J. Agric. Food Chem. 53: 1563-1570.
    Pubmed CrossRef
  3. Ramal ho SD, de Sousa LR, Burger MC, Lima MI, da Sil va MF, Fernandes JB, et al. 2015. Evaluation of flavonols and derivatives as human cathepsin B inhibitor. Nat. Prod. Res. 29: 2212-2214.
    Pubmed CrossRef
  4. Qiu X, Kroeker A, He S, Kozak R, Audet J, Mbikay M, Chretien M. 2016. Prophylactic efficacy of quercetin 3-β -O -D-glucoside against Ebola virus infection. Antimicrob. Agents Chemother. 60: 5182-5188.
    Pubmed CrossRef Pubmed Central
  5. Lee S, Sy S, Lee Y, Park Y, Kim BG, Ahn JH, et al. 2011. Rhamnetin production based on the rational design of the poplar O-methyltransferase enzyme and its biological activities. Bioorg. Med. Chem. Lett. 21: 3866-3870.
    Pubmed CrossRef
  6. Makino T, Shimizu R, Kanemaru M, Suzuki Y, Moriwaki M, Mizukami H. 2009. Enzymatically modified isoquercitrin, alpha-oligoglucosyl quercetin 3-O-glucoside, is absorbed more easily than other quercetin glycosides or aglycone after oral administration in rats. Biol. Pharm. Bull. 32: 2034-2040.
    Pubmed CrossRef
  7. Darsandhari S, Bae JY, Shrestha B,Yamaguchi T, Jung HJ, Han JM, et al. 2018. Enzymatic synthesis of novel quercetin sialyllactoside derivatives. Nat. Prod. Res. 6: 1-9.
  8. Lee YS, Huh JY, Nam SH, Kim D, Lee SB. 2013. Synthesis of quercetin-3-O-glucoside from rutin by Penicillium decumbens naringinase. J. Food Sci. 78: C411-415.
    Pubmed CrossRef
  9. de Araújo ME, Moreira Franco YE, Alberto TG, Sobreiro MA, Conrado MA, Priolli DG, et al. 2012. Enzymatic deglycosylation of rutin improves its antioxidant and antiproliferative activities. Food Chem. 141: 266-273.
    Pubmed CrossRef
  10. Lee YS, Woo JB, Ryu SI, Moon SK, Han NS, Lee SB. 2017. Glucosylation of flavonol and flavanones by Bacillus cyclodextrin glucosyltransferase to enhance their solubility and stability. Food Chem. 229: 75-83.
    Pubmed CrossRef
  11. Rha CS, Choi JM, Jung YS, Kim ER, Ko MJ, Seo DH, et al. 2019. High-efficiency enzymatic production of αisoquercitrin glucosides by amylosucrase from Deinococcus geothermalis. Enzym. Microb. Technol. 120: 84-90.
    Pubmed CrossRef
  12. Kim JH, Shin KH, Ko JH, Ahn JH. 2006. Gl ucosyl ation of flavonols by Escherichia coli expressing glucosyltransferase from rice (Oryza sativa). J. Biosci. Bioeng. 102: 135-137.
    Pubmed CrossRef
  13. Pandey RP, Malla S, Simkhada D, Kim BG, Sohng JK. 2013. Production of 3-O-xylosyl quercetin in Escherichia coli. Appl. Microbiol. Biotechnol. 97: 1889-1901.
    Pubmed CrossRef
  14. Yoon JA, Kim BG, Lee WJ, Lim Y, Chong Y, Ahn JH. 2002. Production of a novel quercetin glycoside through metabolic engineering of Escherichia coli. Appl. Environ. Microbiol. 78: 4256-4262.
    Pubmed CrossRef Pubmed Central
  15. An DG, Yang SM, Kim BG, Ahn JH. 2016. Biosynthesis of two quercetin O-diglycosides in Escherichia coli. J. Ind. Microbiol. Biotechnol. 43: 841-849.
    Pubmed CrossRef
  16. Choi GS, Kim HJ, Kim EJ, Lee SJ, Lee Y, Ahn JH. 2018. Stepwise synthesis of quercetin bisglycosides using engineered Escherichia coli. J. Microbiol. Biotechnol. 28: 1859-1864.
    Pubmed CrossRef
  17. Han SH, Kim BG, Yoon JA, Chong Y, Ahn JH. 2014. Synthesis of flavonoid O-pentosides by Escherichia coli through engineering of nucleotide sugar synthesis pathways and glycosyltransferase. Appl. Environ. Microbiol. 80: 2754-2762.
    Pubmed CrossRef Pubmed Central
  18. Kim SY, Lee HR, Park KS, Kim BG, Ahn JH. 2015. Metabolic engineering of Escherichia coli for the biosynthesis of flavonoid O-glucuronides and flavonoid O-galactoside. Appl. Microbiol. Biotechnol. 99: 2233-2242.
    Pubmed CrossRef
  19. Pandey RP, Jung HY, Parajuli P, Nguyen THT, Bashyal P, Sohng JK. 2019. A synthetic approach for biosynthesis of miquelianin and scutellarin A in Escherichia coli. Appl. Sci. 9: 215.
    CrossRef
  20. Kim BG, Shin KH, Lee Y, Hur HG, Lim Y, Ahn JH. 2005. Multiple regiospecific methylations of a flavonoid by plant O-methyltransferases expressed in E. coli. Biotechnol. Lett. 27: 1861-1864.
    Pubmed CrossRef
  21. Darsandhari S, Dhakal D, Shrestha B, Parajuli P, Seo JH, Kim TS, et al. 2018. Characterization of regioselective flavonoid O-methyltransferase from the Streptomyces sp. KCTC 0041BP. Enzym. Microb. Technol. 113: 29-36.
    Pubmed CrossRef
  22. Xu JQ, Fan N, Yu BY, Wang QQ, Zhang J. 2017. Biotransformation of quercetin by Gliocladium deliquescens NRRL 1086. Chin. J. Nat. Med. 15: 615-624.
    CrossRef
  23. Marvalina C, Azerada R. 2011. Microbial glucuronidation of polyphenols. J. Mol. Catal. B Enzym. 73: 43-52.
    CrossRef
  24. Ma B, Zeng J, Shao L, Zhan J. 2013. Efficient bioconversion of quercetin into a novel glycoside by Streptomyces rimosus subsp. rimosus ATCC 10970. J. Biosci. Bioeng. 115: 24-26.
    Pubmed CrossRef Pubmed Central
  25. Hosny M, Dhar K, Rosazza JPN. 2001. Hydroxylations and methylations of quercetin, fisetin, and catechin by Streptomyces griseus. J. Nat. Prod. 64: 462-465.
    Pubmed CrossRef
  26. de MB Costa EM, Pimenta FC, Luz WC, de Oliveira V. 2008. Selection of filamentous fungi of the Beauveriagenus able to metabolize quercetin like mammalian cells. Braz. J. Microbiol. 39: 405-408.
    CrossRef
  27. Lesjak M, Beara I, Simin I, Pintać D, Majkić T, Bekvalac K, et al. 2018. Antioxidant and anti-inflammatory activities of quercetin and its derivatives. J. Funct. Foods. 40: 68-75.
    CrossRef
  28. Rice-Evans CA, Miller NJ, Paganga G. 1996. Structureantioxidant activity relationships of flavonoids and phenolic acids. Free Radic. Biol. Med. 20: 933-956.
    CrossRef
  29. Santos AC, Uyemura SA, Lopes JL, Bazon JN, Mingatto FE, Curti C. 1998. Effect of naturally occurring flavonoids on lipid peroxidation and membrane permeability transition in mitochondria. Free Radic. Biol. Med. 24: 1455-1461.
    CrossRef
  30. Lee CW, Seo JY, Lee J, Choi JW, Cho S, Bae JY, et al. 2017. 3-O-Glucosylation of quercetin enhances inhibitory effects on the adipocyte differentiation and lipogenesis. Biomed. Pharmacother. 95: 589-598.
    Pubmed CrossRef



Copyright © 2009 by the Korean Society for Microbiology and Biotechnology.
All right reserved. Mail to jmb@jmb.or.kr
Online ISSN: 1738-8872    Print ISSN: 1017-7825    Powered by INFOrang Co., Ltd