Naringinases: Occurrence, characteristics, and applications

Applied Microbiology and Biotechnology

Volumn 90, Issue 6, 2011, Pages 1883-1895

  Ribeiro, Maria H ^a  

^a RESEARCH INSTITUTE FOR MEDICINES IMED ULISBOA   (Portugal)

Author keywords

L Rhamnosidase; D Glucosidase; Deglycosylation; Glycosides; Immobilization; Naringinase

Indexed keywords

BIOCHEMICAL PROPERTIES; CITRUS JUICES; DEBITTERING; DEGLYCOSYLATION; ENZYME COMPLEXES; FOOD INDUSTRIES; NARINGIN; NARINGINASE; SUBSTRATE SPECIFICITY; WINE INDUSTRY;

FRUIT JUICES; GLUCOSE; SUBSTRATES; WINE;

GLYCOSIDES;

ANTIBIOTIC AGENT; AURANTIIN; ENZYME; GINSENOSIDE; GLYCOLIPID; ISOQUERCITRIN; NARINGINASE; PRUNIN; QUERCETIN; RHAMNOSE; STEROID; UNCLASSIFIED DRUG;

ANTIBIOTICS; BIOCHEMISTRY; BIOTECHNOLOGY; BIOTRANSFORMATION; ENZYME ACTIVITY; FOOD INDUSTRY; HYDROLYSIS; IMMOBILIZATION; PHARMACEUTICAL INDUSTRY; STEROID; SUBSTRATE;

AROMA; BIOTRANSFORMATION; CITRUS FRUIT; DEBITTERING; DEGLYCOSYLATION; ENZYME ACTIVITY; ENZYME SYNTHESIS; HYDROLYSIS; NONHUMAN; SHORT SURVEY; TASTE ACUITY; WINE;

BETA-GLUCOSIDASE; BIOTECHNOLOGY; FOOD TECHNOLOGY; MULTIENZYME COMPLEXES; MULTIPROTEIN COMPLEXES; SUBSTRATE SPECIFICITY; TECHNOLOGY, PHARMACEUTICAL;

CITRUS;

EID: 79958195828     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-011-3176-8     Document Type: Short Survey

References (78)

1. Amaro MI, Rocha J, Vila-Real H, Eduardo-Figueira M, Mota-Filipe H, Sepodes B, Mota-Filipe H, Ribeiro MHL (2009) Anti-inflamatory activity of naringin and the biosynthesised naringenin by naringinase immobilised in microstructure materials in a model DSS-induced colitis in mice. Food Res Int 42:1010-1017
2. Birgisson H, Wheat JO, Hreggvidsson GO, Kristjansson JK, Mattiasson B (2007) Immobilization of a recombinant Escherichia coli producing a thermostable rhamnosidase: creation of a bioreactor for hydrolyses of naringin. Enz Microb Technol 40:1181-1187
3. Bram B, Solomons GL (1965) Production of the enzyme naringinase by Aspergillus niger. Appl Microbiol 13:842-845
4. Busto MD, Meza V, Ortega N, Perez-Mateos M (2007) Immobilization of naringinase from Aspergillus niger CECT 2088 in poly (vinyl alcohol) cryogels for the debittering of juices. Food Chem 104:1177-1182 (Pubitemid 46764470)
5. Caldini C, Bonomi F, Pifferi PG, Lanzarini G, Galente YM (1994) Kinetic and immobilization studies on fungal glycosidase for aroma enhancement in wine. Enz Microb Technol 16:286-291 (Pubitemid 24128064)
6. Chang H-Y, Lee Y-B, Bae H-A, Huh J-Y, Nam S-H, Sohn H-S, Lee HJ, Lee S-B (2011) Purification and characterisation of Aspergillus sojae naringinase: the production of prunin exhibiting markedly enhanced solubility with in vitro inhibition of HMG-CoA reductase. Food Chem 124:234-241
7. Chen Y, Shen S, Lin H (2003) Rutinoside at C7 attenuates the apoptosis-inducing activity of flavonoids. Biochem Pharm 66:1139-1150 (Pubitemid 37130289)
8. Chien PJ, Fuu S, Shyu YT (2001) Monitoring enzymatic debittering in grapefruit juice by high performance liquid chromatography. J Food Drug Anal 9:115-120 (Pubitemid 33690816)
9. Daniels L, Linhardt RJ, Bryan BA, Mayerl F, Pickenhagen M (1990) Methods for producing rhamnose. US Patent 4(933):281
10. Davis DW (1947) Determination of flavonones in citrus juice. Anal Chem 19:46-48
11. Dunlap WJ, Hagen RE, Wender SH (1962) Preparation and properties of rhamnosidase and glucosidase fractions from a fungal flavonoid glycosidase preparation, "Naringinase C-100". J Food Sci 27:597-601
12. Ellenrieder G, Blanco S, Daz M (1998) Hydrolysis of supersaturated naringin solutions by free and immobilized naringinase. Biotechnol Technol 12:63-65 (Pubitemid 28102196)
13. Elujoba AA, Hardman R (1987) Diosgenin production by acid and enzymatic hydrolysis of fenugreek. Fitoterapia 58:299-303 (Pubitemid 18000243)
14. Erlund I (2004) Review of the flavonoids quercetin, hesperetin, and naringenin. Dietary sources, bioactivities, bioavailability, and epidemiology. Nutr Res 24:851-874
15. Esaki S, Ohishi A, Katsumata A, Sugiyama N, Kamiya S (1993) Synthesis of alpha-L-mannopyranosyl-containing disaccharides and phenols as substrates for the alpha-L-mannosidase activity of commercial naringinase. Biosci Biotechnol Biochem 57:2099-2103
16. Feng B, Kang L, Ma B, Quan B, Zhou W, Wang Y, Zhao Y, Liu Y, Wang S (2007) The substrate specificity of a glucoamylase with steroidal saponin-rhamnosidase activity from Curvularia lunata. Tetrahedron 63:6796-6812 (Pubitemid 46856597)
17. Ferreira L, Afonso C, Vila-Real H, Alfaia A, Ribeiro MHL (2008) Debittering of grapefruit juice with naringinase. Food Technol Biotechnol 46:144-148
18. Fukumoto J, Okada S (1973) Naringinase production by fermentation. Jpn Patent 7(306):554
19. Gorinstein S, Leontowicz H, Leontowicz M, Krzeminski R, Gralak M, Delgado-Licon E, Ayala ALM, Katrich E, Trakhtenberg SJ (2005) Comparison of the contents of the main antioxidant compounds and the antioxidant activity of white grapefruit and his new hybrid. Agr Food Chem 53:3223-3228
20. Habelt K, Pittner F (1983) A rapid method for the determination of naringin, prunin, and naringenin applied to the assay of naringinase. Anal Biochem 134:393-397
21. Hall DH (1938) A new enzyme of the glycosidase type. Chem Ind 57:473
22. Hoechst (1994) Alpha-rhamnosidase production by Penicillium sp., and purification and characterization. German Patent EP 599, 159
23. Ito T, Takiguchi Y (1970) Naringinase production by Cochiobolus miyabeanus. Jpn Patent 7(014):875
24. Jansz ER, Nikawela JK, Gooneratne J, Theivendirarajah K (1994) Studies on the bitter principle and debittering of Palmyrah fruit pulp. J Sci Food Agr 65:185-189 (Pubitemid 2096150)
25. Jimeno A, Manjon A, Canovas M, Iborra JL (1987) Use of naringinase immobilized on glycophase-coated porous glass for fruit juice debittering. Process Biochem 22:13-16
26. Kishi K (1955) Production of naringinase from Aspergillus niger. Kagaku to Kogyo. Chem Ind Jpn 29:140
27. 1 from protopanaxatriol-type ginseng saponin mixture. Planta Med 69:285-286
28. Ko SR, Choi KJ, Suzuki K, Suzuki Y (2003b) Enzymatic preparation of ginsenosides Rg2, Rh1, and F1. Chem Pharm Bull 51:404-408
29. Magario I, Ma X, Neumann A, Syldatk C, Hausmann R (2008) Nonporous magnetic micro-particles: comparison to porous enzyme carriers for a diffusion rate-controlled enzymatic conversion. J Biotechnol 134:72-78
30. Magario I, Neumann A, Oliveros E, Syldatk C (2009a) Deactivation kinetics and response surface analysis of the stability of alpha-L-rhamnosidase from Penicillium decumbens. Appl Biochem Biotechnol 152:29-41
31. Magario I, Vielhauer O, Neumann A, Hausmann R, Syldatk C (2009b) Kinetic analysis and modeling of the liquid-liquid conversion of emulsified di-rhamnolipids by Naringinase from Penicillium decumbens. Biotechnol Bioeng 102:9-19
32. Manjon A, Bastida J, Romero C, Jimeno A, Iborra JL (1985) Immobilization of naringinase on glycophase-coated porous glass. Biotechnol Lett 7:477-482 (Pubitemid 15001407)
33. Manjon A, Iborra JL, Gómez JL, Gómez E, Bastida J, Bódalo A (1987) Evaluation of the effectiveness factor along immobilized enzyme fixed-bed reactors: design of a reactor with naringinase covalently immobilized into glycophase-coated porous glass. Biotechnol Bioeng 30:491-497 (Pubitemid 17657485)
34. Manzanares P, Orejas M, Gil JV, Graaff LH, Visser J, Ramon D (2003) Construction of a genetically modified wine yeast strain expressing the Aspergillus aculeatus rhaA gene, encoding an α-L-rhamnosidase of enological interest. Appl Environ Microbiol 69:7558-7562 (Pubitemid 38585418)
35. Marques J, Vila-Real HJ, Alfaia AJ, Ribeiro MHL (2007) Modelling of the high pressure-temperature effects on naringin hydrolysis based on response surface methodology. Food Chem 105:504-510 (Pubitemid 47048540)
36. Mateles RI, Perlman D, Humphery AE, Deindorfer FH (1965) Fermentation review. Biotechnol Bioeng 7:54-758
37. Miller GL (1959) Use of dinitrosalicylic acid reagent for determination of reducing sugar. Anal Chem 31:426-428
38. Mishra P, Kar R (2003) Treatment of grapefruit juice for bitterness removal by amberlite IR 120 and amberlite IR 400 and alginate entrapped naringinase enzyme. J Food Sci 68:1229-1233 (Pubitemid 36632062)
39. Nobile MAD, Piergiovanni L, Buonocore GG, Fava P, Puglisi ML, Nicolais L (2003) Naringinase immobilization in polymeric films intended for food packaging applications. J Food Sci 68:2046-2049 (Pubitemid 37024116)
40. Nomura D (1965) Studies on the naringinase produced by Coniothyrium diplodiella I. The properties of naringinase and the removal of co-existing pectinase from the enzyme preparation. Enzymologia 29:272-282
41. Norouzian D, Hosseinzadeh A, Inanlou DN, Moazami N (1999) Various techniques used to immobilize naringinase produced by Penicillium decumbens PTCC 5248. World J Microbiol Biotechnol 15:501-502 (Pubitemid 29478327)
42. Nunes MA, Vila-Real H, Fernandes PC, Ribeiro MHL (2010) Immobilization of naringinase in PVA-alginate matrix using an innovative technique. Appl Biochem Biotechnol 160:2129-2147
43. Okada S, Kishi K, Higashihara M, Fukumoto J (1963) Studies on the purification properties of naringinase from Aspergillus niger. J Agric Chem Soc 37:142
44. Olsons AC, Gray GM, Guadagni DG (1979) Naringin bitterness of grapefruit juice debittered with naringinase immobilized in a hollow fiber. J Food Sci 44:1358-1361
45. Orejas M, Ibanez E, Ramon D (1999) The filamentous fungus Aspergillus nidulans produces an α-L-rhamnosidase of potential oenological interest. Lett Appl Microbiol 28:383-388 (Pubitemid 29229512)
46. Pedro HAL, Alfaia AJ, Marques J, Vila-Real HJ, Calado A, Ribeiro MHL (2007) Design of an immobilized enzyme system for naringin hydrolysis at high-pressure. Enz Microb Technol 40:442-446 (Pubitemid 46073156)
47. Prakash S, Singhal RS, Kulkarni PR (2002) Enzymatic debittering of Indian grapefruit (Citrus paradasis) juice. J Sci Food Agric 82:394-397 (Pubitemid 34220145)
48. Puri M, Banerjee U (2000) Production, purification, and characterization of the debittering enzyme naringinase. Biotechnol Adv 18:207-217 (Pubitemid 30446084)
49. Puri M, Kalra S (2005) Purification and characterization of naringinase from a newly isolated strain of Aspergillus niger 1344 for the transformation of flavonoids. World J Microbiol Biotechnol 21:753-758 (Pubitemid 41073919)
50. Puri M, Marwaha SS, Kothari RM, Kennedy JF (1996) Studies on the applicability of alginate entrapped naringinase for the debittering of Kinnow juice. Enz Microb Technol 18:281-285 (Pubitemid 26077599)
51. Puri M, Seth M, Marwaha SS, Kothari RM (2001) Debittering of Kinnow juice by covalent bound naringinase on hen egg white. Food Biotechnol 15:13-23 (Pubitemid 34152374)
52. Puri M, Kaur H, Kennedy JF (2005) Covalent immobilization of naringinase for the transformation of a flavonoid. J Chem Technol Biotechnol 80:1160-1165 (Pubitemid 41419393)
53. Puri M, Kaur A, Singh RS, Singh A (2009) Response surface optimization of medium components for naringinase production from Staphylococcus xylosus MAK2. Appl Biochem Biotechnol 162:181-191
54. Puri M, Kaur A, Barrow CJ, Singh RS (2010) Citrus peel influences the production of an extracellular naringinase by Staphylococcus xylosus MAK2 in a stirred tank reactor. Appl Microbiol Biotechnol. doi:10.1007/s0025301028974
55. Ribeiro IAC, Ribeiro MHL (2008) Kinetic modelling of naringin hydrolysis using a bitter sweet alfa-rhamnopyranosidase immobilized in k-carrageenan. J Mol Catal B Enz 51:10-18 (Pubitemid 350297035)
56. Ribeiro IA, Rocha J, Sepodes B, Mota-Filipe H, Ribeiro MHL (2008) Effect of naringin enzymatic hydrolysis towards naringenin on the anti-inflammatory activity of both compounds. J Mol Catal BEnz 52-53:13-18
57. Ribeiro MHL, Afonso C, Vila-Real HJ, Alfaia AJ, Ferreira L (2010) Contribution of response surface methodology to the modeling of naringin hydrolysis by naringinase Ca- alginate beads under high pressure. LWT Food Sci Technol 43:482-487
58. Roitner M, Schalkhammer Th, Pittner F (1984) Preparation of prunin with the help of immobilized naringinase pretreated with alkaline buffer. App Biochem Biotech 9:483-488
59. Saerens K, Bogaert IV, Soetaert W, Vandamme E (2009) Production of glucolipids and specialty fatty acids from sophorolipids by Penicillium decumbens naringinase: optimization and kinetics. Biotechn J 4:517-524
60. Sankyo (1988) Preparation of antibiotic chloropolysporin-C. Jpn Patent 63(146):797
61. Şekeroǧlu G, Fadiloǧlu S, Göǧü ş F (2006) Immobilization and characterization of naringinase for the hydrolysis of naringin. Eur Food Res Technol 224:55-60
62. Shanmugam V, Yadav KDS (1995) Extracellular production of alpharhamnosidase by Rhizopus nigricans. Ind J Exp Biol 33:705-707
63. Soares N, Hotchkiss F (1998) Naringinase immobilization in packaging films for reducing naringin concentration in grapefruit. J Food Sci 63:61-65 (Pubitemid 28165272)
64. Soria F, Ellenrieder G, Grasselli M, Navarro del Cañizo AA, Cascone O (2004) Fractionation of the naringinase complex from Aspergillus terreus by dye affinity chromatography. Biotechnol Lett 26:1265-1268 (Pubitemid 39384830)
65. Spagma G, Barbagallo RN, Martino A, Pifferi PG (2000) A simple method of purifying glycosidase: α-L-rhamnopyranosidases from Aspergillus niger to increase the aroma of Moscato wine. Enzyme Microb Technol 27:522-30
66. Suzuki H (1962) Hydrolysis of flavonoid glycosides by enzymes (Rhamnodiastase) from Rhamnus and other sources. Arch Biochem Biophys 99:476-483
67. Thammawat K, Pongtanya P, Juntharasri V, Wongvithoonyaporn P (2008) Isolation, preliminary enzyme characterization and optimization of culture parameters for production of naringinase isolated from Aspergillus niger BCC 25166. Kasetsart J Nat Sci 42:61-72 (Pubitemid 351196033)
68. Thomas DW, Smythe CV, Labbee MD (1958) Enzymatic hydrolysis of naringin, the bitter principle of grapefruit. Food Res 23:591-598
69. Ting SV (1958) Enzymatic hydrolysis of naringin in grapefruit. J Agric Food Chem 6:546-549
70. Tsen H-Y, Tsai S-Y (1988) Comparison of the kinetics and factors affecting the stabilities of chitin-immobilized naringinases from two fungal sources. J Ferment Technol 66:193-198
71. Tsen H-Y, Tsai S-Y, Gee-Kaite Yu (1989) Fiber entrapment of naringinase from Penicillium sp. and application to fruit juice debittering. J Ferm Bioeng 67:186-189
72. Vila-Real HJ, Alfaia AJ, Calado AT, Ribeiro MHL (2007) High pressure-temperature effects on enzymatic activity: naringin bioconversion. Food Chem 102:565-570 (Pubitemid 46108258)
73. Vila-Real H, Alfaia AJ, Emilia Rosa M, Calado ART, Ribeiro MHL (2010a) An innovative sol-gel naringinase bioencapsulation process for glycosides hydrolysis. Process Biochem 45:841-850
74. Vila-Real H, Alfaia AJ, Rosa J, Góis P, Rosa ME, Calado ART, Ribeiro MHL (2010b) α-Rhamnosidase and β-glucosidase expressed by naringinase immobilized on new ionic liquid sol-gel matrices: activity and stability studies. J Biotechnol. doi:10.1016/j.jbiotec.2010.08.005
75. Vila-Real H, Alfaia AJ, Calado ART, Ribeiro MHL (2010c) Improvement of activity and stability of soluble and sol-gel immobilized naringinase in co-solvent systems. J Mol Catal B Enz 65:91-101
76. Yanai T, Sato M (2000) Purification and characterization of α-L-rhamnosidases from Pichia angusta X349. Biosci Biotechnol Biochem 64(10):2179-85
77. Young NM, Johnston RAZ, Richards JC (1989) Purification of the α-L-rhamnosidase of Penicillium decumbens and characterisation of two glycopeptide components. Carbohydr Res 191:53-62
78. Zverlov VV, Hertel C, Bronnenmeier K, Hroch A, Kellermann J, Schwarz WH (2000) The thermostable alpha-L-rhamnosidase RamA of Clostridium stercorarium: biochemical characterization and primary structure of a bacterial alpha-L-rhamnoside hydrolase, a new type of inverting glycoside hydrolase. Mol Microb 35:173-179 (Pubitemid 30032280)