Enzymatic acylation of flavonoids: Effect of the nature of the substrate, origin of lipase, and operating conditions on conversion yield and regioselectivity

Journal of Agricultural and Food Chemistry

Volumn 55, Issue 23, 2007, Pages 9496-9502

  Chebil, Latifa ^a   Anthoni, Julie ^a   Humeau, Catherine ^a   Gerardin, Christine ^a   Engasser, Jean Marc ^a   Ghoul, Mohamed ^a  

^a UNIVERSITÉ DE LORRAINE   (France)

Author keywords

Acetylation; Candida antarctica lipase B; Flavonoid; Pseudomonas cepacia lipase C; Regioselectivity

Indexed keywords

FLAVONOID; LIPASE B, CANDIDA ANTARCTICA; SOLVENT; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; BURKHOLDERIA CEPACIA; CHEMISTRY; COMPARATIVE STUDY; ENZYME SPECIFICITY; ENZYMOLOGY; GLYCOSYLATION; METABOLISM;

ACYLATION; BURKHOLDERIA CEPACIA; FLAVONOIDS; GLYCOSYLATION; LIPASE; SOLVENTS; SUBSTRATE SPECIFICITY;

BURKHOLDERIA CEPACIA; CANDIDA ANTARCTICA; PSEUDOMONAS;

EID: 36749090008     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf071943j     Document Type: Article

References (36)

1. Burda, S.; Oleszek, W. Antioxidant and antiradical activities of flavonoids. J. Agric. Food Chem. 2001, 49, 2774-2779.
2. Di Carlo, G.; Mascolo, N.; Izzo, A. A.; Capasso, F. Flavonoids: Old and new aspects of a class of natural therapeutic drugs. Life Sci. 1999, 65, 337-353.
3. Formica, J. V.; Regelson, W. Review of the biology of quercetin and related bioflavonoids. Food Chem. Toxicol. 1995, 33, 1061-1080.
4. Ross, J. A.; Kasum, C. M. Dietary flavonoids: Bioavailability, metabolic effects, and safety. Annu. Rev. Nutr. 2002, 22, 19-34.
5. Harborne, J. B.; Williams, C. A. Advances in flavonoid research since 1992. Phytochemistry 2000, 55, 481-504.
6. Cherng, J. M.; Shieh, D. E.; Chiang, W.; Chang, M. Y.; Chiang, L. C. Chemopreventive effects of minor dietary constituents in common foods on human cancer cells. Biosci. Biotechnol. Biochem. 2007, 71, 1500-1504.
7. Ramos, S. Effects of dietary flavonoids on apoptotic pathways related to cancer chemoprevention. J. Nutr. Biochem. 2007, 18, 427-442.
8. Ishihara, K.; Nakajima, N. Structural aspects of acylated plant pigments: stabilization of flavonoid glucosides and interpretation of their functions. J. Mol. Catal B: Enzym. 2003, 23, 411-417.
9. Kitao, S.; Ariga, T.; Matsudo, T.; Sekine, H. The syntheses of catechin-glucosides by transglycosylation with Leuconostoc mesenteroides sucrose phosphorylase. Biosci. Biotechnol. Biochem. 1993, 57, 2010-2015.
10. Tommasini, S.; Raneri, D.; Ficarra, R.; Calabro, M. L.; Stancanelli, R.; Ficarra, P. Improvement in solubility and dissolution rate of flavonoids by complexation with β-cyclodextrin. J. Pharmaceut. Biomed. Anal. 2004, 35, 379-387.
11. Ardhaoui, M.; Falcimaigne, A.; Ognier, S.; Engasser, J. M.; Moussou, P.; Pauly, G.; Ghoul, M. Effect of acyl donor chain length and substitutions pattern on the enzymatic acylation of flavonoids. J. Biotechnol. 2004, 110, 265-272.
12. Lambusta, D.; Nicolosi, G.; Patti, A.; Piattelli, M. Enzyme-mediated regioprotection-deprotection of hydroxyl groups in (+)-catechin. Synthesis 1993, 11, 1155-1158.
13. Lambusta, D.; Nicolosi, G.; Patti, A.; Sanfilippo, C. Application of lipase catalysis in organic solvents for selective protection-deprotection of bioactive compounds. J. Mol. Catal. B: Enzym. 2003, 22, 271-277.
14. Mellou, F.; Loutrari, H.; Stamatis, H.; Roussos, C.; Kolisis, F. N. Enzymatic esterification of flavonoids with unsaturated fatty acids: Effect of the novel esters on vascular endothelial growth factor release from K562 cells. Process Biochem. 2006, 41, 2029-2034.
15. Ardhaoui, M.; Falcimaigne, A.; Engasser, J. M.; Moussou, P.; Pauly, G.; Ghoul, M. Enzymatic synthesis of new aromatic and aliphatic esters of flavonoids using Candida antarctica lipase as biocatalyst. Biocatal. Biotransform. 2004, 22, 253-259.
16. Ardhaoui, M.; Falcimaigne, A.; Engasser, J.-M.; Moussou, P.; Pauly, G.; Ghoul, M. Acylation of natural flavonoids using lipase of Candida antarctica as biocatalyst. J. Mol. Catal. B: Enzym. 2004, 29, 63-67.
17. Chebil, L.; Humeau, C.; Falcimaigne, A.; Engasser, J.-M.; Ghoul, M. Enzymatic acylation of flavonoids. Process Biochem. 2006, 41, 2237-2251.
18. Danieli, B.; Luisetti, M.; Sampognaro, G.; Carrea, G.; Riva, S. Regioselective acylation of polyhydroxylated natural compounds catalyzed by Candida Antarctica lipase B (Novozym 435) in organic solvents. J. Mol. Catal. B: Enzym. 1997, 3, 193-201.
19. Katsoura, M. H.; Polydera, A. C.; Tsironis, L.; Tselepis, A. D.; Stamatis, H. Use of ionic liquids as media for the biocatalytic preparation of flavonoid derivatives with antioxidant potency. J. Biotechnol. 2006, 123, 491-503.
20. Kontogianni, A.; Skouridou, V.; Sereti, V.; Stamatis, H.; Kolisis, F. N. Regioselective acylation of flavonoids catalyzed by lipase in low toxicity media. Eur. J. Lipid Sci. Technol. 2001, 103, 655-660.
21. Kontogianni, A.; Skouridou, V.; Sereti, V.; Stamatis, H.; Kolisis, F. N. Lipase-catalyzed esterification of rutin and naringin with fatty acids of medium carbon chain. J. Mol. Catal B: Enzym. 2003, 21, 59-62.
22. Mellou, F.; Lazari, D.; Skaltsa, H.; Tselepis, A. D.; Kolisis, F. N.; Stamatis, H. Biocatalytic preparation of acylated derivatives of flavonoid glycosides enhances their antioxidant and antimicrobial activity. J. Biotechnol. 2005, 116, 295-304.
23. Nakajima, N.; Ishihara, K.; Itoh, T.; Furuya, T.; Hamada, H. Lipase-catalyzed direct and regioselective acylation of flavonoid glucoside for mechanistic investigation of stable plant pigments. J. Biosci. Bioeng. 1999, 87, 105-107.
24. Min Sin, Y.; Woong Choo, K.; Ho Lee, T. Synthesis of fructose esters by Pseudomonas sp. lipase in anhydrous pyridine. Biotechnol. Lett. 1998, 20, 91-94.
25. Agrawal, P. K. Carbon-13 NMR of Flavonoids; Elsevier: Berlin, 1989; pp 78-79.
26. Stevenson, D. E.; Wibisono, R.; Jensen, D. J.; Stanley, R. A.; Cooney, J. M. Direct acylation of flavonoid glycosides with phenolic acids catalysed by Candida antarctica lipase B (Novozym 435(R)). Enzyme Microb. Technol. 2006, 39, 1236-1241.
27. Hazarika, S.; Goswami, P.; Dutta, N. N. Lipase catalysed transesterification of 2-O-benzylglycerol with vinyl acetate: solvent effect. Chem. Eng. J. 2003, 94, 1-10.
28. MacManus, D. A.; Vulfson, E. N. Reversal of regioselectivity in the enzymatic acylation of secondary hydroxyl groups mediated by organic solvents. Enzyme Microb. Technol. 1997, 20, 225-228.
29. Lopez, R.; Montero, E.; Sanchez, F.; Canada, J.; Fernandez-Mayoralas, A. Regioselective acetylations of alkyl β-D-xylopyranosides by use of lipase PS in organic solvents and application to the chemoenzymic synthesis of oligosaccharides. J. Org. Chem. 1994, 59, 7027-7032.
30. Passicos, E.; Santarelli, X.; Coulon, D. Regioselective acylation of flavonoids catalyzed by immobilized Candida antarctica lipase under reduced pressure. Biotechnol. Lett. 2004, 26, 1073-1076.
31. Arcos, J. A.; Bernabé, M.; Otero, C. Quantitative enzymatic production of 1,6-diacyl sorbitol esters. Biotechnol. Bioeng. 1998, 60, 53-60.
32. Arcos, J. A.; Bernabé, M.; Otero, C. Quantitative enzymatic production of 6-acylglucose esters. Biocatal Biotransform. 1998, 57, 505-509.
33. Van Acker, S. A. B. E.; de Groot, M. J.; van den Berg, D.-J.; Tromp, M. N. J. L.; Donne-Op den Kelder, G.; van der Vijgh, W. J. F.; Bast, A. A Quantum chemical explanation of the antioxidant activity of flavonoids. Chem. Res. Toxicol. 1996, 9, 1305-1312.
34. Russo, N. T. M.; Uccella, N. Semiempirical molecular modeling into quercetin reactive site: structural, conformational, and electronic features. J. Agric. Food Chem. 2000, 48, 3232-3237.
35. Erkoc, S.; Erkoc, F.; Keskin, N. Theoretical investigation of quercetin and its radical isomers. J. Mol. Struct. 2003, 631, 141-146.
36. Shin, J.-S.; Kim, K.-S.; Kim, M.-B.; Jeong, J.-H.; Kim, B.-K. Synthesis and hypoglycemic effect of chrysin derivatives. Bioorg. Med. Chem. Lett. 1999, 9, 869-874.