Mechanism of inhibition of rice bran lipase by polyphenols: A case study with chlorogenic acid and caffeic acid

Journal of Food Science

Volumn 72, Issue 8, 2007, Pages

  Raghavendra, M P ^a   Kumar, Parigi Ramesh ^a   Prakash, V ^a  

^a CENTRAL FOOD TECHNOLOGICAL RESEARCH INSTITUTE   (India)

Author keywords

Caffeic acid; Chlorogenic acid; Conformational stability; Hydrophobic interaction; Inactivation; Polyphenols; Rice bran lipase; Thermal denaturation temperature

Indexed keywords

CAFFEIC ACID; CAFFEIC ACID DERIVATIVE; CHLOROGENIC ACID; ENZYME INHIBITOR; FLAVONOID; PHENOL DERIVATIVE; POLYPHENOLS; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; CIRCULAR DICHROISM; DOSE RESPONSE; DRUG ANTAGONISM; ENZYMOLOGY; KINETICS; METABOLISM; OXIDATION REDUCTION REACTION; PROTEIN CONFORMATION; PROTEIN DENATURATION; RICE; SPECTROFLUOROMETRY; TEMPERATURE; ULTRAVIOLET SPECTROPHOTOMETRY;

CAFFEIC ACIDS; CHLOROGENIC ACID; CIRCULAR DICHROISM; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; FLAVONOIDS; KINETICS; LIPASE; ORYZA SATIVA; OXIDATION-REDUCTION; PHENOLS; PROTEIN CONFORMATION; PROTEIN DENATURATION; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET; TEMPERATURE;

EID: 35348883808     PISSN: 00221147     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1750-3841.2007.00488.x     Document Type: Article

References (72)

1. Aizono Y, Funatsu M, Fujiki Y, Watanabe M. 1976. Purification and characterization of rice bran lipase II. Agric Biol Chem 40 : 317 24.
2. Alison D, Purich DL. 1979. Practical considerations in the design of initial velocity enzyme rate assays. Methods Enzymol 63 : 3 22.
3. Baxter NJ, Lilley TH, Haslam E, Williamson MP. 1997. Multiple interactions between polyphenols and a salivary prolinerich protein repeat result in complexation and precipitation. Biochemistry 36 : 5566 77.
4. Belle V, Fournel A, Woudstra M, Ranaldi S, Prieri F, Thome V, Currault J, Verger R, Guigliarelli B, Carriere F. 2007. Probing the opening of the pancreatic lipase lid using site-directed spin labeling and EPR spectroscopy. Biochemistry 46 : 2205 14.
5. Breinholt V. 1999. Desirable versus harmful levels of intake of flavonoids and phenolic acids. In : Kumpulainen J, Salonen JE, editors. Natural antioxidants and anticarcinogens in nutrition, health and disease. Cambridge : The Royal Society of Chemistry, p 93 105.
6. Brzozowski AM, Derewenda U, Derewenda ZS, Dodson GG, Lawson DM, Turkenburg JP, Bjorkling F, Huge-Jensen B, Patkar SA, Thim LA. 1991. A model for interfacial activation in lipases from the structure of a fungal lipase-inhibitor complex. Nature 351 : 491 4.
7. Cheng JC, Dai F, Zhou B, Yang L, Liu, ZL. 2007. Antioxidant activity of hydroxycinnamic acid derivatives in human low density lipoprotein: mechanism and structure-activity relationship. Food Chem 104 : 132 9.
8. Dupas C, Baglieri AM, Ordonaud C, Tom D, Maillard, MN. 2006. Chlorogenic acid is poorly absorbed, independently of the food matrix: a Caco-2 cells and rat chronic absorption study. Mol Nutr Food Res 50 : 1053 60.
9. Duthie GG, Duthie SJ, Kyle JAM. 2000. Plant polyphenols in cancer and heart disease: implications as nutritional antioxidants. Nutr Res Rev 13 : 79 106.
10. Enochain RV, Saunders RM, Schultz WG, Beagle EC, Crowley PR. 1981. Stabilization of rice bran with extruder cookers and recovery of edible oil: a preliminary analysis of operational and financial feasibility. Marketing Research Report No. 1120, USDA.
11. Fromm HJ. 1979. Use of competitive inhibitors to study substrate binding order. Methods Enzymol 63 : 467 86.
12. Fujiki Y, Aizono Y, Funatsu M. 1978. Chemical properties of major subunit of rice bran lipase. Agri Biol Chem 42 : 599 606.
13. Funatsu M, Aizono Y, Hayashi K, Watanabe M, Eto M. 1973. Biochemical studies on rice bran lipase Part I. Purification and physical properties. Agric Biol Chem 35 : 734 42.
14. Gopalakrishna KN, Purnima Kaul, Ramesh Kumar P, Prakash V. 2002. Role of disulfide bridges in structure-activity relationship of plant lipases from wheat germ and rice bran. Ind J Biotechnol 1 : 188 96.
15. He Q, Yuanping L, Yao K. 2006. Effects of tea polyphenols on the activities of α- amylase, pepsin, trypsin and lipase. Food Chem 101 : 1178 82.
16. Hermoso J Pignol D, Kerfelec B, Crenon I, Chapus C, Fontecilla-Camps JC. 1996. Lipase activation by nonionic detergents. The crystal structure of the porcine lipase-colipase-tetraethylene glycol monooctyl ether complex. J Biol Chem 271 : 18007 16.
17. Herrmann K. 1989. Occurrence and content of hydroxycinnamic and hydroxybenzoic acid compounds in foods. CRC Crit Rev Food Sci Nutr 28 : 315 47.
18. Hirayama O, Matsuda H. 1975. Purification and characterization of lipolytic acyl hydrolases from rice bran. Nippon Nogei Kagaku Kaishi 49 : 569 76.
19. Hurell RF, Finot PA, Cuq JL. 1982. Protein-polyphenol reactions.1. Nutritional and metabolic consequences of the reaction between oxidized caffeic acid and the lysine residues of casein. Br J Nutr 47 : 191 211.
20. Juliano BO. 1994. Rice: chemistry and technology. St. Paul, Minn American Association of Cereal Chemists.
21. Kang J, Liu Y, Xie MX, Li S, Jiang M, Wang YD. 2004. Interactions of human serum albumin with chlorogenic acid and ferulic acid. Biochim Biophys Acta 1674 : 205 14.
22. Kontogianni A, Skouridou V, Sereti V, Stamatis H, Kolisis FN. 2003. Lipase-catalyzed esterification of rutin and naringin with fatty acids of medium carbon chain. J Mol Catal B Enzym 21 : 59 62.
23. Kroll J, Rawel H. 2001. Reactions of plant phenols with myoglobin: influence of chemical structure of the phenolic compounds. J Food Sci 66 : 48 58.
24. Lakkakula NR, Lima M, Walker T. 2004. Rice bran stabilization and rice bran oil extraction using ohmic heating. Bioresource Technol 92 : 157 61.
25. Laranjinha J, Vieira O, Madeira V, Almeida L. 1995. Two related phenolic antioxidants with opposite effects on vitamin E content in low density lipoprotein oxidized by ferryl myoglobin: consumption vs regeneration. Arch Biochem Biophys 323 : 373 81.
26. Lehrer SS, Fasman GD. 1966. The fluorescence of lysozyme and lysozyme substrate complexes. Biochem Biophys Res Commun 23 : 133 8.
27. Lineweaver H, Burk D. 1934. The determination of enzyme dissociation constant. J Am Chem Soc 56 : 658 66.
28. Mason HS, Peterson EW. 1955. The reaction of quinones with protamine and nucleoprotamine: N-terminal proline. J Biol Chem 212 : 485 93.
29. McCaskill DR, Zhang F. 1999. Use of rice bran oil in foods. Food Technol 53 (2 50 2.
30. Mogensen JE, Sehgal P, Otzen DE. 2005. Activation, inhibition, and destabilization of Thermomyces lanuginosus lipase by detergents. Biochemistry 44 : 1719 30.
31. Muralidhara BK, Prakash V. 1995. Interaction of 3′-O-caffeoyl d-quinic acid with human serum albumin. Int J Peptide Protein Res 46 : 1 8.
32. Nakai M, Fukui Y, Asami S, Ono YT, Iwashita T, Shibata H, Mitsunaga T, Hashimoto F, Kiso Y. 2005. Inhibitory effects of oolong tea polyphenols on pancreatic lipase in vitro. J Agric Food Chem 53 : 4593 8.
33. Nardini M, D'Aquino M, Tomassi G, Gentili V, Di Felice M, Scaccini C. 1995. Inhibition of human low-density lipoprotein oxidation by caffeic acid and other hydroxycinnamic acid derivatives. Free Rad Biol Med 19 : 541 52.
34. Nardini M, Cirillo E, Natella F, Mencarelli D, Comisso A, Scaccini, C. 2002. Detection of bound phenolic acids: prevention by ascorbic acid and ethylenediaminetetra acetic acid of degradation of phenolic acids during alkaline hydrolysis. Food Chem 79 : 119 24.
35. Nasirullah, Krishnamurthy MN, Nagaraja KV. 1989. Effect of stabilization on the quality characteristics of rice bran oil. J Am Oil Chem Soc 66 : 661 3.
36. Pace CN, Shirley BA, Thomson JA. 1989. Measuring the conformational stability of a protein. In : Crieghton TE, editor. The protein structure: a practical approach. Oxford : IRL Press. p 311 30.
37. Passicos E, Santarelli X, Coulon D. 2004. Regioselective acylation of flavonoids catalyzed by immobilized Candida antarctica lipase under reduced pressure. Biotechnol Lett 26 : 1073 6.
38. Raghavendra MP, Prakash V. 2002. Phenylboronic acids - a potent inhibitor of lipase from Oryza sativa. J Agric Food Chem 50 : 6037 41.
39. Raghavendra Rao SN, Ananthchar TK, Desikachar HSR. 1965. Oil content of bran from rice milled to different degrees of polishing. J Food Sci Technol 2 : 115 6.
40. Rajeshwara AN, Prakash V. 1995. Purification and characterization of lipase from rice (Oryza sativa L.) bran. Die Nahrung 39 : 406 18.
41. Rajeshwara AN, Gopalakrishna KN, Prakash V. 1996. Preferential interaction of denaturants with rice bran lipase. Int J Biol Macromol 19 : 1 7.
42. Ramezanzadeh FM, Rao RM, Prinyawiwatkul W, Marshall WE, Windhauser M. 2000. Effects of microwave heat, packaging, and storage temperature on fatty acid and proximate compositions in rice bran. J Agric Food Chem 48 (2 464 7.
43. Randall JM, Sayre RN, Schultz WG, Fong AP, Mossman RE, Trihethron, Saunders RM. 1985. Rice bran stabilization by extrusion cooking for extraction of edible oil. J Food Sci 50 (2 361 4, 368.
44. Rawel H, Kroll J, Riese B. 2000. Reactions of chlorogenic acid with lysozyme-physicochemical characterisation and proteolytic digestion of the derivatives. J Food Sci 65 : 1091 8.
45. Rawel H, Kroll J, Rohn S. 2001. Reactions of phenolic substances with lysozyme-physicochemical characterisation and proteolytic digestion of the derivatives. Food Chem 72 : 59 71.
46. Rawel HM, Czajka D, Rohn S, Kroll J. 2002a. Interactions of different phenolic acids and flavonoids with soy proteins. Int J Biol Macromol 30 : 137 50.
47. Rawel HM, Rohn S, Kruse HP, Kroll J. 2002b. Structural changes induced in bovine serum albumin by covalent attachment of chlorogenic acid. Food Chem 78 : 443 55.
48. Robbins RJ. 2003. Phenolic acids in foods: an overview of analytical methodology. J Agri Food Chem 51 : 2866 87.
49. Roche M, Dufour C, Mora N, Dangles O. 2005. Antioxidant activity of olive phenols: mechanistic investigation and characterization of oxidation products by mass spectrometry. Org Biomol Chem 3 : 423 30.
50. Rohn S, Rawel HM, Kroll J. 2002. Inhibitory effects of plant phenols on the activity of selected enzymes. J Agric Food Chem 50 : 3566 71.
51. Salvia A, Carrupta PA, Tillementb JP, Testaa B. 2001. Structural damage to proteins caused by free radicals: asessment, protection by antioxidants, and influence of protein binding. Biochem Pharmacol 61 : 1237 42.
52. Saunders RM. 1985. Rice bran: composition and potential food sources. Food Rev Int 1 (3 465 95.
53. Saunders RM. 1990. The properties of rice bran as a food stuff. Cer Foods World 35 : 632 62.
54. Sayre RN, Nayyar DK, Saunders RM. 1985. Extraction and refining of edible oil from extrusion-stabilized rice bran. J Am Oil Chem Soc 62 (6 1040 3.
55. Sbarraa V, Ristorcellia E, Petit-Thévenina JL, Teissedreb PL, Lombardoa D, Vérinea A. 2005. In vitro polyphenol effects on activity, expression and secretion of pancreatic bile salt-dependent lipase. Biochim Biophys Acta 1736 : 67 76.
56. Shahidi F, Naczk M. 1995. Food phenolics. Lancaster, Basel : Technomic Publishing Co.
57. Shastry BS, Raghavendra Rao MR. 1976. Chemical studies on rice bran lipase. Cereal Chem 53 : 190 200.
58. Siebert KJ. 1999. Effects of protein-polyphenol interactions on beverage haze, stabilization, and analysis. J Agric Food Chem 47 : 353 62.
59. Siebert KJ, Troukhanova NV, Lynn PY. 1996. Nature of polyphenol-protein interactions. J Agric Food Chem 44 : 80 5.
60. Sreenarayanan VV, Chattopadhyay PK. 1986. Rice bran stabilization by dielectric heating. J Food Proc Preserv 10 : 89 98.
61. Stamatis H, Sereti V, Kolisis FN. 2001. Enzymatic synthesis of hydrophilic and hydrophobic derivatives of natural phenolic acids in organic media. J Mol Catal B Enzym 11 : 323 8.
62. Stevenson DE, Wibisono R, Jensen DJ Stanley RA, Cooney JM. 2006. Direct acylation of flavonoid glycosides with phenolic acids catalysed by Candida antarctica lipase B (Novozym 435®). Enzyme Microb Technol 39 : 1236 41.
63. Sudhindra Rao K, Rajendran S, Rajeshwara AN, Prakash V. 1991. Structural stability of lipase from wheat germ in alkaline pH. J Protein Chem 10 : 291 9.
64. Suryaprakash P, Prakash V. 1995. Interaction of 3′-0-caffeoyl D-quinic acid with multisubunit protein helianthinin. J Biosci 20 : 531 49.
65. Suryaprakash P, Ramesh Kumar P, Prakash V. 2000. Thermodynamics of interaction of caffeic acid and quinic acid with multisubunit proteins. Int J Biol Macromol. 27 : 219 28.
66. Taubert D, Breitenbach T, Lazar A, Censarek P, Harlfinger S, Berkels R. 2003. Reaction rate constants of superoxide scavenging by plant antioxidants. Free Rad Biol Med 35 : 1599 607.
67. Thomas PP, Gopalkrishnan N, Damodaran AD. 1991. Rice bran lipase inactivation by microwaves for low free fatty acid oil. Oleagineux 46 : 245 46.
68. Todhunter JA. 1979. Reversible enzyme inhibition. Methods Enzymol 63 : 383 411.
69. Ward LD. 1985. Measurement of ligand binding to proteins by fluorescence spectroscopy. Methods Enzymol 117 : 400 14.
70. Widmer TL, Laurent N. 2006. Plant extracts containing caffeic acid and rosmarinic acid inhibit zoospore germination of Phytophthora spp. pathogenic to Theobroma cacao. Eur J Plant Pathol 115 : 377 88.
71. Yang JT, Wu CC, Martinez HM. 1986. Calculation of protein conformation from circular dichroism. Methods Enzymol 130 : 208 69.
72. Yeh CT, Yen GC. 2003. Effects of phenolic acids on human phenolsulfotransferases in relation to their antioxidant activity. J Agric Food Chem. 57 : 1474 9.