Skip to main content
SpringerLink
Log in

Controllable Regioselective Acylation of Rutin Catalyzed by Enzymes in Non-aqueous Solvents

  • Published:
Biotechnology Letters Aims and scope Submit manuscript

Abstract

An efficient route to synthesize 3′′- and 4′′′-vinyl rutin esters has been developed by enzyme-catalyzed regioselective acylation of rutin with divinyl dicarboxylates in organic media. Alkaline protease from Bacillus subtilis provided 3′′-O-substituted vinyl rutin esters in pyridine, and Novozym 435 gave 4′′′-O-substituted vinyl rutin esters in tert-butanol.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • M Ardhaoui A Falcimaigne JM Engasser P Moussou G Pauly M Ghoul (2004) ArticleTitleAcylation of natural flavonoids using lipase of Candida antarctica as biocatalyst J. Mol. Catal. B-Enzym. 29 63–67 Occurrence Handle10.1016/j.molcatb.2004.02.013

    Article  Google Scholar 

  • B Danieli M Luisetti G Sampognaro G Carrea S Riva (1997) ArticleTitleRegioselective acylation of polyhydroxylated natural compounds catalyzed by Candida antarctica lipase B (Novozym 435) in organic solvents J. Mol. Catal. B-Enzym. 3 193–201 Occurrence Handle10.1016/S1381-1177(96)00055-0

    Article  Google Scholar 

  • B Danieli PD Bellis (1990) ArticleTitleEnzyme-mediated regioselective acylation of flavonoid disaccharide monoglycosides Helv. Chim. Acta 73 1837–1844 Occurrence Handle10.1002/hlca.19900730705

    Article  Google Scholar 

  • E Enaud C Humeau B Piffaut M Girardin (2004) ArticleTitleEnzymatic synthesis of new aromatic esters of phloridzin J. Mol. Catal. B-Enzym. 27 1–6 Occurrence Handle10.1016/j.molcatb.2003.08.002

    Article  Google Scholar 

  • PJ Ferguson E Kurowska DJ Freeman AF Chambers DJ Koropatnick (2004) ArticleTitleA flavonoid fraction from cranberry extract inhibits proliferation of human tumor cell lines J. Nutr. 134 1529–1535 Occurrence Handle15173424

    PubMed  Google Scholar 

  • CL Gao P Mayon DA MacManus EN Vulfson (2001) ArticleTitleNovel enzymatic approach to the synthesis of flavonoid glycosides and their esters Biotechnol. Bioeng. 71 235–243 Occurrence Handle10.1002/1097-0290(2000)71:3<235::AID-BIT1013>3.0.CO;2-M

    Article  Google Scholar 

  • S Gayot X Santarelli D Coulon (2003) ArticleTitleModification of flavonoid using lipase in non-conventional media: effect of the water content J. Biotechnol. 101 29–36 Occurrence Handle10.1016/S0168-1656(02)00286-9 Occurrence Handle12523967

    Article  PubMed  Google Scholar 

  • A Kontogianni V Skouridou V Sereti H Stamatis FN Kolisis (2003) ArticleTitleLipase-catalyzed esterification of rutin and naringin with fatty acids of medium carbon chain J. Mol. Catal. B-Enzym. 21 59–62 Occurrence Handle10.1016/S1381-1177(02)00139-X

    Article  Google Scholar 

  • P Lagiou E Samoli A Lagiou A Tzonou A Kalandidi J Peterson J Dwyer D Trichopoulos (2004) ArticleTitleIntake of specific flavonoid classes and coronary heart disease – a case-control study in Greece Eur. J. Clin. Nutr. 58 1643–1648 Occurrence Handle10.1038/sj.ejcn.1602022 Occurrence Handle15226759

    Article  PubMed  Google Scholar 

  • VV Mozhaev CL Budde JO Rich AY Usyatinsky PC Michels YL Khmelnitsky DS Clark JS Dordick (1998) ArticleTitleRegioselective enzymatic acylation as a tool for producing solution-phase combinatorial libraries Tetrahedron 54 3971–3982 Occurrence Handle10.1016/S0040-4020(98)00129-X

    Article  Google Scholar 

  • N Nakajima K Ishihara T Itoh T Furuya H Hamada (1999) ArticleTitleLipase-catalyzed direct and regioselective acylation of flavonoid glucoside for mechanistic investigation of stable plant pigments J. Biosci. Bioeng. 87 105–107 Occurrence Handle10.1016/S1389-1723(99)80017-6 Occurrence Handle16232434

    Article  PubMed  Google Scholar 

  • E Passicos X Santarelli D Coulon (2004) ArticleTitleRegioselective acylation of flavonoids catalyzed by immobilized Candida antarctica lipase under reduced pressure Biotechnol. Lett. 26 1073–1076 Occurrence Handle10.1023/B:BILE.0000032967.23282.15 Occurrence Handle15218382

    Article  PubMed  Google Scholar 

  • S Riva (1996) ArticleTitleA two-step efficient chemoenzymatic synthesis of flavonoid glycoside malonates J. Nat. Prod. 59 618–621 Occurrence Handle10.1021/np960239m Occurrence Handle8786368

    Article  PubMed  Google Scholar 

  • Y Sakihama MF Cohen SC Grace H Yamasaki (2002) ArticleTitlePlant phenolic antioxidant and prooxidant activities: phenolics-induced oxidative damage mediated by metals in plants Toxicology 177 67–80 Occurrence Handle10.1016/S0300-483X(02)00196-8 Occurrence Handle12126796

    Article  PubMed  Google Scholar 

  • N Wang Q Wu BK Liu Y Cai XF Lin (2004) ArticleTitleEnzyme-catalyzed regioselective synthesis of lipophilic guaifenesin ester derivatives J. Mol. Catal. B-Enzym. 27 97–102 Occurrence Handle10.1016/j.molcatb.2003.10.002

    Article  Google Scholar 

  • K Yoshimoto Y Itatani Y Tsuda (1980) ArticleTitle13C-Nuclear magnetic resonance spectra of O-acylglucose. Additivity of shift parameters and its application to structure elucidations Chem. Pharm. Bull. 28 2065–2074

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Zhejiang University, 310027, Hangzhou, People’s Republic of China

    Yong-mei Xiao, Qi Wu, Wei-bo Wu, Qing-yi Zhang & Xian-fu Lin

Authors
  1. Yong-mei Xiao
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Qi Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Wei-bo Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Qing-yi Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Xian-fu Lin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Xian-fu Lin.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Xiao, Ym., Wu, Q., Wu, Wb. et al. Controllable Regioselective Acylation of Rutin Catalyzed by Enzymes in Non-aqueous Solvents. Biotechnol Lett 27, 1591–1595 (2005). https://doi.org/10.1007/s10529-005-2513-3

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10529-005-2513-3

Keywords

Search

Navigation