Biocatalytic preparation of alkyl esters of citrus flavanone glucoside prunin in organic media

Process Biochemistry

Volumn 46, Issue 1, 2011, Pages 94-100

  Céliz, Gustavo ^a   Daz, Mirta ^a  

^a UNIVERSIDAD NACIONAL DE SALTA   (Argentina)

Author keywords

Citrus; Flavanones; Flavonoids; Lipases; Naringin; Prunin

Indexed keywords

CITRUS; FLAVANONES; FLAVONOIDS; NARINGIN; PRUNIN;

ACETONE; ACETONITRILE; ALKYLATION; ESTERIFICATION; ESTERS; ISOMERS; ORGANIC SOLVENTS; REGIOSELECTIVITY; RESINS;

LIPASES;

CANDIDA ANTARCTICA; CITRUS; RHIZOMUCOR; RHIZOMUCOR MIEHEI;

EID: 78650245192     PISSN: 13595113     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.procbio.2010.07.022     Document Type: Article

References (46)

1. K.A. Lyseng-Williamson, and C.M. Perry Micronised purified flavonoid fraction: a review of its use in chronic venous insufficiency, venous ulcers and haemorrhoids Drugs 63 2003 71 100
2. M.C. Misra, and Imlitemsu Drug treatment of haemorrhoids Drugs 65 2005 1481 1491
3. G. Ellenrieder Biotransformations of citrus flavanone glycosides A. Pandey, Concise encyclopedia of bioresource technology 2004 The Haworth press New York 189 200
4. O. Benavente-Garcia, and J. Castillo Update on uses and properties of citrus flavonoids: new findings in anticancer, cardiovascular, and anti-inflammatory activity J Agric Food Chem 56 2008 6185 6205
5. G. Ellenrieder, S. Blanco, and M. Daz Hydrolysis of supersaturated naringin solutions by free and immobilized naringinase Biotechnol Tech 12 1998 63 65
6. J.S. Choi, T. Yokozawa, and H. Oura Antihyperlipidemic effect of flavonoids from Prunus davidiana J Nat Prod 54 1991 218 224
7. J.S. Choi, T. Yokozawa, and H. Oura Improvement of hyperglycemia and hyperlipemia in streptozotocin-diabetic rats by a methanolic extract of Prunus davidiana stems and its main component, prunin Planta Med 57 1991 208 211
8. X. Han, J. Pan, D. Ren, Y. Cheng, P. Fan, and H. Lou Naringenin-7-O- glucoside protects against doxorubicin-induced toxicity in H9c2 cardiomyocytes by induction of endogenous antioxidant enzymes Food Chem Toxicol 46 2008 3140 3146
9. X. Han, D. Ren, P. Fan, T. Shen, and H. Lou Protective effects of naringenin-7-O-glucoside on doxorubicin-induced apoptosis in H9C2 cells Eur J Pharmacol 581 2008 47 53
10. Y. Imai, S. Tsukaharas, S. Asada, and Y. Sugimoto Phytoestrogens/ Flavonoids reverse breast cancer resistance protein/ABCG2-mediated multidrug resistance Cancer Res 64 2004 4346 4352
11. K.E. Malterud, T.E. Bremnes, A. Faegri, T. Moe, and E.K. Sandanger Dugstad Flavonoids from the wood of salix caprea as inhibitors of wood-destroying fungi J Nat Prod 48 1985 559 563
12. H. Yao, Z.X. Liao, Q. Wu, G.Q. Lei, Z.J. Liu, and D.F. Chen Antioxidative flavanone glycosides from the branches and leaves of Viscum coloratum Chem Pharm Bull 54 2006 133 135
13. L. Chebil, C. Humeau, A. Falcimaigne, J.M. Engasser, and M. Ghoul Enzymatic acylation of flavonoids Process Biochem 41 2006 2237 2251
14. J. Viskupičová, E. Šturdík, and M. Ondrejovič Enzymatic transformation of flavonoids Acta Chim Slovaca 2 2009 88 106
15. Y. Watanabe, M. Nagai, K. Yamanaka, K. Jose, and M. Nomura Synthesis of lauroyl phenolic glycoside by immobilized lipase in organic solvent and its antioxidative activity Biochem Eng J 43 2009 261 265
16. M.H. Katsoura, A.C. Polydera, L. Tsironis, A.D. Tselepis, and H. Stamatis Use of ionic liquids as media for the biocatalytic preparation of flavonoid derivatives with antioxidant potency J Biotechnol 123 2006 491 503
17. M.H. Katsoura, A.C. Polydera, P. Katapodis, F.N. Kolisis, and H. Stamatis Effect of different reaction parameters on the lipase-catalyzed selective acylation of polyhydroxylated natural compounds in ionic liquids Process Biochem 42 2007 1326 1334
18. S.H. Youn, H.J. Kim, T.H. Kim, and C.S. Shin Lipase-catalyzed acylation of naringin with palmitic acid in highly concentrated homogeneous solutions J Mol Catal B Enzym 46 2007 26 31
19. B. Danieli, P. De Bellis, G. Carrea, and S. Riva Enzyme-mediated regioselective acylations of flavonoid disaccharide monoglycosides Helv Chim Acta 73 1990 1837 1844
20. S. Riva, B. Danieli, and M. Luisetti A two-step efficient chemoenzymatic synthesis of flavonoid glycoside malonates J Nat Prod 59 1996 618 621
21. N. Nakajima, K. Ishihara, T. Itoh, T. Furuya, and H. Hamada Lipase-catalyzed direct and regioselective acylation of flavonoid glucoside for mechanistic investigation of stable plant pigments J Biosci Bioeng 87 1999 105 107
22. C. Gao, O. Mayon, D.A. MacManus, and E.N. Vulfson Novel enzymatic approach to the synthesis of flavonoid glycosides and their esters Biotechnol Bioeng 71 2000 235 243
23. A. Kontogianni, V. Skouridou, V. Sereti, H. Stamatis, and F.N. Kolisis Regioselective acylation of flavonoids catalyzed by lipase in low toxicity media Eur J Lipid Sci Technol 103 2001 655 660
24. Otto RT, Geers B, Weiss A, Petersohn D, Schlotmann K, Schroeder KL. Novel flavone glycoside derivatives for use in cosmetics, pharmaceuticals and nutrition. WO 0179245 2001.
25. S. Gayot, X. Santarelli, and D. Coulon Modification of flavonoid using lipase in non-conventional media: effect of the water content J Biotechnol 101 2003 29 36
26. A. Kontogianni, V. Skouridou, V. Sereti, H. Stamatis, and F.N. Kolisis Lipase-catalyzed esterification of rutin and naringin with fatty acids of medium carbon chain J Mol Catal B Enzym 21 2003 59 62
27. E. Passicos, X. Santarelli, and D. Coulon Regioselective acylation of flavonoids catalyzed by immobilized Candida antarctica lipase under reduced pressure Biotechnol Lett 26 2004 1073 1076
28. F. Mellou, D. Lazari, H. Skaltsa, A.D. Tselepis, F.N. Kolisis, and H. Stamatis Biocatalytic preparation of acylated derivatives of flavonoid glycosides enhances their antioxidant and antimicrobial activity J Biotechnol 116 2005 295 304
29. F. Mellou, H. Loutrari, H. Stamatis, C. Roussos, and F.N. Kolisis Enzymatic esterification of flavonoids with unsaturated fatty acids: effect of the novel esters on vascular endothelial growth factor release from K562 cells Process Biochem 41 2006 2029 2034
30. ®) Enzyme Microb Technol 39 2006 1236 1241
31. Geronazzo H, Robin J, Blanco S, Cuevas C, Ellenrieder G. Aprovechamiento integral de residuos de producción y procesamiento de pomelos. Un proyecto de innovación tecnólogica. In Actas VIII Congreso Argentino de Ciencia y Tecnología de Alimentos. Argentina: Santa Fe. 1999.
32. F. Soria, and G. Ellenrieder Thermal inactivation and product inhibition of Aspergillus terreus CECT 2663 α-rhamnosidase and their role on hydrolysis of naringin solutions Biosci Biotechnol Biochem 66 2002 1442 1449
33. W. Brand-Williams, M.E. Cuvelier, and C. Berset Use of a free radical method to evaluate antioxidant activity LWT Food Sci Technol 28 1995 25 30
34. M. Degueil-Castaing, B. de Jeso, S. Drouillard, and B. Maillard Enzymatic reactions in organic synthesis: 2-ester interchange of vinyl esters Tetrahedron Lett 28 1987 953 954
35. S. Hazarika, P. Goswami, and N.N. Dutta Lipase catalysed transesterification of 2-o-benzylglycerol with vinyl acetate: solvent effect Chem Eng J 94 2003 1 10
36. L. Chebil, J. Anthoni, C. Humeau, C. Gerardin, J.M. Engasser, and M. Ghoul Enzymatic acylation of flavonoids: effect of the nature of the substrate. origin of lipase, and operating conditions on conversion yield and regioselectivity J Agric Food Chem 55 2007 9496 9502
37. B. Danieli, M. Luisetti, G. Sampognaro, G. Carrea, and S. Riva Regioselective acylation of polyhydroxylated natural compounds catalyzed by Candida antarctica lipase B (Novozym 435) in organic solvents J Mol Catal B Enzym 3 1997 193 201
38. K. Ishihara, and N. Nakajima Structural aspects of acylated plant pigments: stabilization of flavonoid glucosides and interpretation of their functions J Mol Catal B Enzym 23 2003 411 417
39. J. Uppenberg, and M.T. Hansen The sequence, crystal structure determination and refinement of two crystal forms of lipase B from Candida antarctica Structure 2 1994 293 308
40. R.T. Otto, H. Scheib, U.T. Bornscheuer, J. Pleiss, C. Syldatk, and R.D. Schmid Substrate specificity of lipase B from Candida antarctica in the synthesis of arylaliphatic glycolipids J Mol Catal B Enzym 8 2000 201 211
41. J. Pleiss, M. Fischer, and R.D. Schmid Anatomy of lipase binding sites: the scissile fatty acid binding site Chem Phys Lipids 93 1998 67 80
42. J. Uppenberg, N. Öhrner, M. Noria, K. Hule, G.J. Kleywegt, and S. Patear Crystallographic and molecular-modeling studies of lipase B from Candida antarctica reveal a stereospecificity pocket for secondary alcohol Biochemistry (Wash) 34 1995 16838 16851
43. N.R. Pedersen, R. Wimmer, J. Emmersen, P. Degn, and L.H. Pedersen Effect of fatty acid chain length on initial reaction rates and regioselectivity of lipase-catalysed esterification of disaccharides Carbohydr Res 337 2002 1179 1184
44. R.L. Prior, X. Wu, and K. Schaich Standardized methods for the determination of antioxidant capacity and phenolics in foods and dietary supplements J Agric Food Chem 53 2005 4290 4302
45. N. Balasundram, K. Sundram, and S. Samman Phenolic compounds in plants and agri-industrial by-products: antioxidant activity, occurrence, and potential uses Food Chem 99 2006 191 203
46. C.A. Rice-Evans, N.J. Miller, and G. Paganga Structure-antioxidant activity relationships of flavonoids and phenolic acids Free Radic Biol Med 20 1996 933 956