Enzymatic synthesis and characterization of arbutin glucosides using glucansucrase from Leuconostoc mesenteroides B-1299CB

Applied Microbiology and Biotechnology

Volumn 77, Issue 3, 2007, Pages 559-567

  Moon, Young Hwan ^a   Nam, Seung Hee ^b   Kang, Jin ^a   Kim, Young Min ^a   Lee, Jin Ha ^a   Kang, Hee Kyung ^a   Breton, Vincent ^d   Jun, Woo Jin ^a   Park, Ki Deok ^a   Kimura, Atsuo ^c   Kim, Doman ^a  

^a Chonnam National University   (South Korea)

^b Jeonnam Agricultural Research and Extension Service   (South Korea)

^c HOKKAIDO UNIVERSITY   (Japan)

^d UNIVERSITÉ CLERMONT AUVERGNE   (France)

Author keywords

Acceptor reaction; Arbutin; Dextransucrase; Glucoside; Leuconostoc mesenteroides

Indexed keywords

ACCEPTOR REACTION; ARBUTIN; DEXTRANSUCRASE; GLUCOSIDE; LEUCONOSTOC MESENTEROIDES;

CHARACTERIZATION; COLUMN CHROMATOGRAPHY; DERIVATIVES; ENZYME ACTIVITY; ENZYME INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SYNTHESIS (CHEMICAL);

GLUCOSE;

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 4 HYDROXYPHENYL BETA ISOMALTOSIDE; 4 HYDROXYPHENYL BETA ISOMALTOTRIOSIDE; ARBUTIN; ARBUTIN GLUCOSIDE; CARBON 13; GLUCANSUCRASE; GLUCOSIDE; INTERSTITIAL COLLAGENASE; MONOPHENOL MONOOXYGENASE; SCAVENGER; SUCRASE; SUCROSE; UNCLASSIFIED DRUG;

ALCOHOL; ENZYME; GAS CHROMATOGRAPHY; GLUCOSE; INHIBITION; LIQUID CHROMATOGRAPHY;

ARTICLE; BACTERIAL STRAIN; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; CORRELATION ANALYSIS; ENZYME SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HUMAN TISSUE; LEUCONOSTOC MESENTEROIDES; NONHUMAN; QUANTUM CHEMISTRY; ULTRAVIOLET B RADIATION;

ARBUTIN; GLUCOSIDES; GLYCOSYLTRANSFERASES; LEUCONOSTOC;

LEUCONOSTOC MESENTEROIDES;

EID: 36248977079     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-007-1202-7     Document Type: Article

References (23)

1. Funayama M, Arakawa H, Yamamoto R, Nishino T, Shin T, Murao S (1995) Effects of alpha and beta arbutin on activity of tyrosinase from mushroom and mouse melanoma. Biosci Biotechnol Biochem 59:143-147
2. Ho JN, Lee YH, Park JS, Jun WJ, Kim HK, Hong BS, Shin DH, Cho HY (2005) Protective effects of aucubin isolated from Eucommia ulmoides against UVB-induced oxidative stress in human skin fibroblasts. Biol Pharm Bull 28:1244-1248
3. Hori I, Nihei KN, Kubo I (2004) Structural criteria for depigmenting mechanisn of arbutin. Phytother Res 18:475-479
4. Jin YH, Lee SJ, Chung MH, Park JH, Cho TH, Lee SK (1999) Aloesin and arbutin inhibit tyrosinase activity in a synergistic manner via a different action mechanism. Arch Pharm Res 22:232-236
5. Kasenko A, Hoffman, Hoffman CA, Shape ES, Jackson RW (1953) Enzymatic synthesis of dextran. Acceptor specificity and chain initiation. J Biol Chem 200:793-801
6. Kim D, Kim DW (1999) Facile purification and characterization of dextransucrase from Leuconostoc mesenteroides B-512FMCM. J. Microbiol Biotechnol 9:219-222
7. Kim MJ, Lee SB, Lee HS, Lee SY, Baek JS, Kim D, Moon TW, Robyt JF, Park KH (1999) Comparative study of the inhibition of. α. -glucosidase,. α. -amylase, and cyclomaltodextrin glucanosyltransferase by acarbose, isoacarbose, and acarviosine-glucose. Arch Biochem Biophys 371:277-283
8. Kim D, Robyt JF, Lee SY, Lee JH, Kim YM (2003) Dextran molecular size and degree of branching as a function of sucrose concentration, pH, and temperature of reaction of Leuconostoc mesenteroides B-512FMCM dextransucrase. Carbohydr Res 338:1183-1189
9. Koepsell HJ, Tsuchiya HM, Hellman N, Koepsell HJ, Tsuchiya HM, Hellman NN, Maeda K, Fukuda M (1996) Arbutin: mechanism of its depigmenting action in human melanocyte culture. J Pharmacol Exp Ther 276(2):765-769
10. Maeda K, Fukuda M (1996) Arbutin: mechanism of its depigmenting action in human melanocyte culture. J Pharmacol Exp Ther 276:765-769
11. Moon YH, Kim G, Lee JH, Jin XJ, Kim DW, Kim D (2006a) Enzymatic synthesis and characterization of novel epigallocatechin gallate glucosides. J Mol Catal B Enzym 40:1-7
12. Moon YH, Lee JH, Ahn JS, Nam SH, Oh DK, Park DH, Chung HJ, Kang SS, Day DF, Kim D (2006b) Synthesis, structure analyses, and characterization of novel epigallocatechin gallate (EGCG) glycosides using the glucansucrase from Leuconostoc mesenteroides B-1299CB. J Agric Food Chem 54:1230-1237
13. Moon YH, Lee JH, Jhon DY, Jun WJ, Kang SS, Sim J, Choi H, Moon JH, Kim D (2007) Synthesis and characterization of novel quercetin-. α. -glucopyranosides using glucansucrase from Leuconostoc mesenteroides. Enzyme Microb Technol 40:1124-1129
14. Mukerjea R, Kim D, Robyt JF (1996) Simplified and improved methylation analysis of saccharides, using a modified procedure and thin-layer chromatography. Carbohydr Res 292:11-20
15. Robyt JF (1995) Mechanism in the glucansucrase synthesis of polysaccharides and oligosaccharides from sucrose. Adv Carbohydr Chem Biochem 51:133-168
16. Robyt JF, Martin PJ (1983) Mechanism of synthesis of d-glucans by d-glucosyltransferase from treptococcus mutans 6715. Carbohydr Res 113:301-315
17. Seo ES, Lee JH, Park JY, Kim D, Han HJ, Robyt JF (2005) Enzymatic synthesis and anti-coagulant effect of salicin analogs by using the Leuconostoc mesenteroides glucansucrase acceptor reaction. J Biotechnol 117:31-38
18. Sugimoto K, Nishimura T, Nomura K, Sugimoto K, Takashi K (2003) Syntheses of arbutin-. α. -glycosides and a comparison of their inhibitory effects with those of. α. -arbutin and arbutin in human tyrosinae. Chem Pharm Bull 51:798-801
19. Sugimoto K, Nomura K, Nishimura T, Kiso T, Sugimoto K, Takashi K (2005) Syntheses of. α. -arbutin-. α. -glycosides and their inhibitory effects on human tyrosinae. J Biosci Bioeng 99:272-276
20. Tomita K, Fukudo M, Kawasaki K (1990) Mechanism of arbutin inhibitory effect on melanogenesis and effect on the human skin with cosmetic use. Fragrance J 6:72-77
21. Watanabe H, Shimizu T, Nishihira J, Abe R, Nakayama T, Taniguchi M, Sabe H, Ishibashi T, Shimizu H (2004) Ultraviolet A-induced production of matrix metalloproteinase-1 is mediated by macrophage migration inhibitory factor (MIF) in human dermal fibroblasts. J Biol Chem 279:1676-1683
22. Yoon SH, Robyt JF (2002) Synthesis of acarbose analogues by transglycosylation reactions of Leuconostoc mesenteroides B-512FMC and B-742CB dextransucrases. Carbohydr Res 337:2427-2435
23. Yoon SH, Fulton DB, Robyt JF (2004) Enzymatic synthesis of two salicin analogues by reaction of salicyl alcohol with Bacillus macerans cyclomaltodextrin glucanyltransferase and. Leuconostoc mesenteroides. B-742CB dextransucrase. Carbohydr Res 339:1517-1529