α-L-rhamnosidases: Old and new insights

Industrial Enzymes: Structure, Function and Applications

Volumn , Issue , 2007, Pages 117-140

  Manzanares, Paloma ^a   Vallés, Salvador ^a   Ramòn, Daniel ^a,b   Orejas, Margarita ^a  

^a INSTITUTO DE AGROQUÍMICA Y TECNOLOGÍA DE ALIMENTOS CSIC   (Spain)

^b UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84892234760     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/1-4020-5377-0_8     Document Type: Chapter

References (88)

1. Acquati, W. and Ponzone, C. (2000) Preparation of desglucodesrhamnoruscin by hydrolysis of Ruscus aculeatus steroid glycosides by fermentation in the presence of Aspergillus niger. Patent number WO200073489-A.
2. Altschul, S.F., Madden, T.L., Schaffer, A.A., Zhang, J., Zhang, Z., Miller, W. and Lipman, D.J. (1997) Gapped BLAST and PSI-BLAST: a new generation of protein database search programs. Nucleic Acid Res. 25, 3389-3402.
3. Bader, G., Wray, V., Just, U. and Hiller, K. (1998) Enzymatic hydrolysis of the cytotoxic glycoside virgaureasaponin 1. Phytochem. 49, 153-156.
4. Bae, E.-A., Shin, J.-E. and Kim, D.-H. (2005) Metabolism of ginsenoside Re by human intestinal microflora and its estrogenic effect. Biol. Pharm. Bull. 28, 1903-1908.
5. Bar-Peled, M., Lewinsohn, E., Fluhr, R. and Gressel, J. (1991) UDP-rhamnose-flavanone-7-O-glucoside- 2"-O-rhamnosyltransferase- purification and characterization of an enzyme catalysing the production of bitter compounds in citrus. J. Biol. Chem. 226, 20953-20959.
6. Barker, S.A., Somers, P.J. and Stacey, M. (1965) Arrangement of the L-rhamnose units in Diplococcus pneumoniae type II polysaccharide. Carbohydr. Res. 1, 106-115.
7. Benavente-García, O., Castillo, J., Marín, F.R., Ortuño, A. and Del Río, J.A. (1997) Uses and properties of Citrus flavonoids. J. Agric. Food Chem. 45, 4505-4515.
8. Birgisson, H., Hreggvidsson, G.O., Fridjónsson, O.H., Mort, A., Kristjánsson, J.K. and Mattiasson, B. (2004) Two new thermostable α-L-rhamnosidases from a novel thermophilic bacterium. Enzyme Microb. Technol. 34, 561-571.
9. Bokkenheuser, V.D., Shackleton, C.H.L. and Winter, J. (1987) Hydrolysis of dietary flavonoid glycosides by strains of intestinal Bacteroides from humans. Biochem. J. 248, 953-956.
10. Bourbouze, R., Percheron, F. and Courtois, J.E. (1976) α-L-Rhamnosidase from Fagopyrum esculentum: purification and some properties. Eur. J. Biochem. 63, 331-337.
11. Boyle, P., Diehm, C. and Roberston, C. (2003) Meta-analysis of clinical trials of Cyclo 3 Fort in the treatment of chronic venous insufficiency. Int. Angiol. 22, 250-262.
12. Chang, P.R. and Muir, A. (2004) Isoquercitrin-enriched composition prepared by incubating solution having rutin after adding naringinase, terminating the incubation, the proportion of isoquercitrin in composition being controlled by adjusting duration of incubation. Patent Number WO2004027074-A2.
13. Chen, Y.-C., Shen, S.-C. and Lin, H.-Y. (2003) Rutinoside at C7 attenuates the apoptosis-inducing activity of flavonoids. Biochem. Pharmacol. 66, 1139-1150.
14. Chua, J.E.H., Manning, P.A. and Morona, R. (1999) The Shigella flexneri bacteriophage Sf6 tailspike protein (TSP)/endorhamnosidase is related to the bacteriophage P22 TSP and has a motif common to exo- and endoglycanases, and C-5 epimerases. Microbiol. 145, 1649-1659.
15. Coutinho, P.M. and Henrissat, B. (1999) Carbohydrate-active Enzymes server at URL http://afmb.cnrs-mrs.fr/CAZY/.
16. Davies, G. and Henrissat, B. (1995) Structures and mechanisms of glycosyl hydrolases. Structure 3, 853-859.
17. Del Nobile, M.A., Piergiovanni, L., Buonocore, G.G., Fava, P., Puglisi, M.L. and Nicolais, L. (2003) Naringinase immobilization in polymeric films intended for food packaging applications. J. Food Sci. 68, 2046-2049.
18. Deng, L., Kasper, D.L., Krick, T.P. and Wessels, M.R. (2000) Characterization of the linkage between the type III capsular polysaccharide and the bacterial cell wall of group B Streptococcus. J. Biol. Chem. 275, 7497-7504.
19. Di Lazzaro, A., Morana, A., Schiraldi, C., Martino, A., Ponzone, C. and De Rosa, M. (2001) An enzymatic process for the production of the pharmacologically active glycoside desglucodesrhamnoruscin from Ruscus aculeatus L.J. Mol. Catal. B.-Enzym. 11, 307-314.
20. Friedman, M. and McDonald, G.M. (1997) Potato glycoalkaloids: chemistry, analysis, safety, and plant physiology. Crit. Rev. Plant Sci. 16, 55-132.
21. Gallego, M.V., Piñaga, F., Ramón, D. and Vallés, S. (1996) Production and characterization of an Aspergillus terreus α-L-rhamnosidase of oenological interest. Z. Lebensm.-Unters.-Forsch. 203, 522-527.
22. Gallego, M.V., Piñaga, F., Ramón, D. and Vallés, S. (2001) Purification and characterization of an Aspergillus terreus α-L-rhamnosidase of interest in winemaking. J. Food Sci. 66, 204-209.
23. Giavasis, I., Harvey, L.M. and McNeil, B. (2000) Gellan gum. Crit. Rev. Biotech. 20, 177-211.
24. Grimaldi, A., Bartowsky, E. and Jiranek, V. (2005) A survey of glycosidase activities of commercial wine strains of Oenococcus oeni. Int. J. Food Microbiol. 105, 233-244.
25. González-Barrio, R., Trindade, L.M., Manzanares, P., de Graaff, L. H., Tomás-Barberán, A. and Espín, J.C. (2004) Production of bioavailable flavonoid glucosides in fruit juices and green tea by use of fungal α-L-rhamnosidases. J. Agric. Food Chem. 52, 6136-6142.
26. Günata, Z. (2003) Flavor enhancement in fruit juices and derived beverages by exogenous glycosidases and consequences of the use of enzyme preparations. In Handbook of Food Enzymology. Whitaker, J.R., Voragen, A.G.J. and Wong, D.W.S. eds. Marcel Dekker Inc., New York, pp 303-330.
27. Günata, Y.Z., Bayonove, C.L., Baumes, R.L. and Cordonnier, R.E. (1985) The aroma of grapes. I. Extraction and determination of free and glycosidically bound fractions of some grape aroma components. J. Chromatogr. 331, 83-90.
28. Haruko, U. and Haruko, O. (1999) Glycobiology of the plant glycoprotein epitope: structure, immunogenicity and allergenicity of plant glycotopes. Trends Glycosci. Glycotech. 11, 413-428.
29. Hashimoto, W., Miyake, O., Nankai, H. and Murata, K. (2003) Molecular identification of an α-L-rhamnosidase from Bacillus sp. strain GL1 as an enzyme involved in complete metabolism of gellan. Arch. Biochem. Biophys. 15, 235-244.
30. Hashimoto, W. and Murata, K. (1998) α-L-Rhamnosidase of Sphingomonas sp. R1 producing an unusual exopolysaccharide of sphingan. Biosci. Biotechnol. Biochem. 62, 1068-1074.
31. Hashimoto, W., Nankai, H., Sato, N., Kawai, S. and Murata, K. (1999) Characterization of α-L-rhamnosidase of Bacillus sp. GL1 responsible for the complete depolymerization of gellan. Arch. Biochem. Biophys. 368, 56-60.
32. Henrissat, B. (1991) A classification of glycosyl hydrolases based on amino acid similarities. Biochem. J. 280, 309-316.
33. Higgings, D., Thompson, J. and Gibson, T. (1996) Using CLUSTAL for multiple sequence alignments. Methods Enzymol. 266, 383-402.
34. Hollman, P.C., Bijsman, M.N., van Gameren, Y., Cnossen, E.P., de Vries, J.P. and Katan, M.B. (1999) The sugar moiety is a major determinant of the absorption of dietary flavonoid glycosides in man. Free Radical Res. 31, 569-573.
35. Hughes, H.B., Morrissey, J.P. and Osbourn, A.E. (2004) Characterisation of the saponin hydrolysing enzyme avenacoside-α-L-rhamnosidase from the fungal pathogen of cereals, Stagonospora avenae. Eur. J. Plant. Pathol. 110, 421-427.
36. Jang, I.-S. and Kim, D.-H. (1996) Purification and characterization of α-L-rhamnosidase from Bacteroides JY-6, a human intestinal bacterium. Biol. Pharm. Bull. 19, 1546-1549.
37. Jansson, P.-E. and Lindberg, B. (1983) Structural studies of gellan gum, an extracellular polysaccharide elaborated by Pseudomona elodea. Carbohydr. Res. 124, 135-139.
38. Kaji, A. and Ichimi, T. (1973) α-L-Rhamnosidase activity in culture filtrate of Corticium rolfsii. Enzymic activity at low pH. Agr. Biol. Chem. 37, 431-432.
39. Kim, J.H., Curtis-Long, M.J., Seo, W.D., Lee, J.H., Lee, B.W., Yoon, Y.J., Kang, K.Y. and Park, K.H. (2005) α-L-Rhamnosidase inhibitory activities of polyhydroxylated pyrrolidine. Bioorg. Med. Chem. Lett. 15, 4282-4285.
40. Kumar, S., Tamura, K. and Nei, N. (2004) MEGA3: Integrated software for molecular evolutionary genetics analysis and sequence alignment. Brief Bioinform. 5, 150-63.
41. Kurosawa, Y., Ikeda, K. and Egami, F. (1973) α-L-Rhamnosidases of the liver of Turbo cornutus and Aspergillus niger. J. Biochem. 73, 31-37.
42. Manzanares, P., de Graaff, L.H. and Visser, J. (1997) Purification and characterization of an α-L-rhamnosidase from Aspergillus niger. FEMS Microbiol. Lett. 157, 279-283.
43. Manzanares, P., Orejas, M., Gil, J.V., de Graaff, L.H., Visser, J. and Ramón, 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.
44. Manzanares, P., Orejas, M., Ibáñez, E., Vallés, S. and Ramón, D. (2000) Purification and characterization of an α-L-rhamnosidase from Aspergillus nidulans. Lett. Appl. Microbiol. 31, 198-202.
45. Manzanares, P., van den Broeck, H., de Graaff, L.H. and Visser, J. (2001) Purification and characterization of two different α-L-rhamnosidases, RhaA and RhaB, from Aspergillus aculeatus. Appl. Environ. Microbiol. 67, 2230-2234.
46. Martearena, M.R., Blanco, S. and Ellenrieder, G. (2003) Synthesis of alkyl-α-L-rhamnosides by water soluble alcohols enzymatic glycosylation. Bioresource Technol. 90, 297-303.
47. Matsumoto, H., Hanamura, S. and Hirayama, M. (2002) Enzymatic production of purified anthocyanins and crystalline products from natural resources, for use in (functional) foods, beverages, drugs and cosmetics. Patent Number WO200222847-A.
48. McMahon, H., Zoecklein, B.W., Fugelsang, K. and Jasinski, Y. (1999) Quantification of glycosidase activity in selected yeasts and lactic acid bacteria. J. Ind. Microbiol. Biotechnol. 23, 198-203.
49. Miake, F., Murata, K., Kuroiwa, A., Kumamoto, T., Kuroda, S., Terasawa, T., Tone, H. and Watanabe, K. (1995) Characterization of Pseudomonas paucimobilis FP2001 which forms flagella depending upon the presence of rhamnose in liquid medium. Microbiol. Immunol. 39, 437-442.
50. Miake, F., Satho, T., Takesue, H., Yanagida, F., Kashige, N. and Watanabe, K. (2000) Purification and characterization of intracellular α-L-rhamnosidase from Pseudomonas paucimobilis FP2001. Arch. Microbiol. 173, 65-70.
51. Miklosy, E. and Polos, V. (1995) Yeasts with β-D-glucosidase activity: properties and posible aplication in winemaking processes. Acta Alimentaria 24, 167-180.
52. Mimaki, Y., Kuroda, M., Kameyama, A., Yokosuka, A. and Sashida, Y. (1998) New steroidal constituents of the underground parts of Ruscus aculeatus and their cytostatic activity on HL-60 cells. Chem. Pharm. Bull. 46, 298-303.
53. Miyata, T., Kashige, N., Satho, T., Yamaguchi, T., Aso, Y. and Miake F. (2005) Cloning, sequence analysis, and expression of the gene encoding Sphingomonas paucimobilis FP2001 α-L-rhamnosidase. Curr. Microbiol. 51, 105-109.
54. Monti, D., Pisvejcová, A., Kren, V., Lama, M. and Riva, S. (2004) Generation of an α-L-rhamnosidase library and its application for the selective derhamnosylation of natural products. Biotechnol. Bioeng. 87, 763-771.
55. Morrissey, J.P., Wubben, J.P. and Osbourn, A.E. (2000) Stagonospora avenae secretes multiple enzymes that hydrolyse oat leaf saponins. Mol. Plant Microbe Interact. 13, 1041-1052.
56. Mutter, M., Beldman, G., Schols, H.A. and Voragen, A.G.J. (1994) Rhamnogalacturonan α-L-rhamnopyranohydrolase. A novel enzyme specific for the terminal nonreducing rhamnosyl unit in rhamnogalacturonan regions of pectin. Plant Physiol. 106, 241-250.
57. Norouzian, D., Hosseinzadeh, A., Inanlou, D.N. and Moazami, N. (1999) Various techniques used to immobilize naringinase produced by Penicillium decumbens PTCC 5248. World J. Microbiol. Biotechnol. 15, 501-502.
58. Ochsner, U.A., Fiechter, A. and Reiser, J. (1994) Isolation, characterization, and expression in Escherichia coli of the Pseudomonas aeruginosa rhlAB genes encoding a rhamnosyltransferase involved in rhamnolipid biosurfactant synthesis. J. Biol. Chem. 31, 19787-19795.
59. Oda, Y., Saito, K., Ohara-Takada, A. and Mori, M. (2002) Hydrolysis of the potato glycoalkaloid α-chaconine by filamentous fungi. J. Biosci. Bioeng. 94, 321-325.
60. Orejas, M., Ibáñez, E. and Ramón, D. (1999) The filamentous fungus Aspergillus nidulans produces an α-L-rhamnosidase of potential oenological interest. Lett. Appl. Microbiol. 28, 383-388.
61. Osbourn, A.E. (1996a) Saponins and plant defense-a soap history. Trends Plant Sci. 1, 4-9.
62. Osbourn, A.E. (1996b) Preformed antimicrobial compounds and plant defense against fungal attack. Plant Cell 8, 1821-1831.
63. Pearson, W.R. (1990) Rapid and sensitive sequence comparison with FASTP and FASTA. Methods Enzymol. 183, 63-98.
64. Pisvejcová, A., Monti, D., Sedmera, P., Tarabiono, C., Lama, M., Riva, S. and Kren, V. (2003) α-L-rhamnosidases and their use in selective trimming of natural compounds. 12th European Carbohydrate Symposium. Grenoble, France, July 6-11. PC022.
65. Prakash, S., Singhal, R.S. and Kulkarni, P.R. (2002) Enzymic debittering of Indian grapefruit (Citrus paradis) juice. J. Sci. Food Agric. 82, 394-397.
66. Puri, M., Kaur, H. and Kennedy, J.F. (2005) Covalent immobilization of naringinase for the transformation of a flavonoid. J. Chem. Technol. Biotechnol. 80, 1160-1165.
67. Puri, M., Marwaha, S.S., Kothari, R.M. and Kennedy, J.F. (1996) Biochemical basis of bitterness in citrus fruit juices and biotech approaches for debbitering. Crit. Rev. Biotechnol. 16, 145-155.
68. Qian, S., Yu, H., Zhang, C., Lu, M., Wang, H. and Jin, F. (2005) Purification and characterization of dioscin-α-L-rhamnosidase from pig liver. Chem. Pharm. Bull. 53, 911-914.
69. Renault, J.-H., Thepenier, P., Zeches-Hanrot, M., Le Men-Olivier, L., Durand, A., Foucault, A. and Margraft, R. (1997) Preparative separation of anthocyanins by gradient elution centrifugal partition chromatography. J. Chromatogr. A 763, 345-352.
70. Ridley, B.L., O'Neill, M.A. and Mohnen, D. (2001) Pectins: structure, biosynthesis and oligogalacturoniderelated signalling. Phytochem. 57, 929-967.
71. Rodríguez, M.E., Lopes, C.A., van Broock, M., Vallés, S., Ramón, D. and Caballero, A.C. (2004) Screening and typing of patagonian wine yeasts for glycosidase activities. J. Appl. Microbiol. 96, 84-95.
72. Romero, C., Manjón, A., Bastida, J. and Iborra, J.L. (1985) A method for assaying the rhamnosidase activity of naringinase. Anal. Biochem. 149, 566-571.
73. Sánchez, M.A., Romero, C., Manjón, A. and Iborra, J.L. (1987) Activity of soluble and immobilized hesperidinase on insoluble hesperidin. Biotechnol. Lett. 9, 871-874.
74. Scaroni, E., Cuevas, C., Carrillo, L. and Ellenrieder, G. (2002) Hydrolytic properties of crude α-L-rhamnosidases produced by several wild strains of mesophilic fungi. Lett. Appl. Microbiol. 34, 461-465.
75. Soares, N.F.F. and Hotchkiss, J.H. (1998) Naringinase immobilization in packaging films for reducing naringin concentration in grapefruit juice. J. Food Sci. 63, 61-65.
76. Steinbacher, S., Seckler, R., Miller, S., Steipe, B., Huber, R. and Reinemer, P. (1994) Crystal structure of P22 tailspike protein: interdigitated subunits in a thermostable trimer. Science 265, 383-386.
77. Suzuki, H. (1962) Hydrolysis of flavonoid glycosides by enzymes: rhamnodiastase from Rhamnus and other sources. Arch. Biochem. Biophys. 99, 476-483.
78. Takatsu, T., Takahashi, S., Takamatsu, Y., Shioiri, T., Iwado, S. and Haneishi, T. (1987a) Chloropolysporins A, B and C, novel glycopeptide antibiotics from Faenia interjecta p.nov. IV. Partially deglycosylated derivatives. J. Antibiot. (Tokyo) 40, 941-945.
79. Takatsu, T., Katayama, T., Nakajima, M., Takahashi, S., Haneishi, T., Magaribuchi, T. and Tajima, M. (1987b) Chloropolysporins A, B and C, novel glycopeptide antibiotics from Faenia interjecta p.nov. V. Comparative studies of the biological properties. J. Antibiot. (Tokyo) 40, 946-952.
80. Thompson, J.D., Higgins, D.G. and Gibson, T.J. (1994) CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res. 22, 4673-4680.
81. Trummler, K., Effenberger, F. and Syldatk, C. (2003) An integrated microbial/enzymatic process for production of rhamnolipids and L-(+)-rhamnose from rapeseed oil with Pseudomonas sp. DSM 2847. Eur. J. Lipid Sci. Technol. 105, 563-571.
82. de Vries, R.P., van Grieken, C., vanKuyk, P.A. and Wösten, H.A. B. (2005) The value of genome sequences in the rapid identification of novel genes encoding specific plant cell wall degrading enzymes. Curr. Genom. 6, 157-187.
83. Yanai, T. and Sato, M. (2000) Purification and characterization of an α-L-rhamnosidase from Pichia angusta X349. Biosci. Biotechnol. Biochem. 64, 2179-2185.
84. Yokozawa, T. and Owada, S. (1999) Effects of ginsenoside Rd in cephaloride-induced renal disorder. Nephron 81, 200-207.
85. Young, N.M., Johnston, R.A.Z. and Richards, J.C. (1989) Purification of the α-L-rhamnosidase of Penicillium decumbens and characteristics of two glycopeptide components. Carbohydr. Res. 191, 53-62.
86. Yu, H., Gong, J., Zhang, C. and Jin, F. (2002) Purification and characterization of ginsenoside-α-Lrhamnosidase. Chem. Pharm. Bull. 50, 175-178.
87. Yu, H., Liu, H., Zhang, C., Tan, D., Lu, M. and Jin, F. (2004) Purification and characterization of gypenoside-α-L-rhamnosidase hydrolysing gypenoside-5 into ginsenoside Rd. Process Biochem. 39, 861-867.
88. Zverlov, V.V., Hertel, C., Bronnenmeier, K., Hroch, A., Kellermann, J. and Schwarz, W.H. (2000) The thermostable α-L-rhamnosidase RamA of Clostridium stercorarium: biochemical characterization and primary structure of a bacterial α-L-rhamnoside hydrolase, a new type of inverting glycoside hydrolase. Mol. Microbiol. 35, 173-179.