Galactosylation of steroidal saponins by β-galactosidase from Lactobacillus bulgaricus L3

Glycoconjugate Journal

Volumn 33, Issue 1, 2016, Pages 53-62

  Zhang, Jie ^a,c   Lu, Lili ^b   Lu, Li ^a   Zhao, Yang ^a   Kang, Liping ^d   Pang, Xu ^a   Liu, Jingyuan ^a   Jiang, Tengchuan ^a   Xiao, Min ^b   Ma, Baiping ^a  

^a BEIJING INSTITUTE OF RADIATION MEDICINE   (China)

^b SHANDONG UNIVERSITY   (China)

^c Deutsches Kunststoff Institut   (Germany)

^d INSTITUTE OF CHINESE MATERIA MEDICA   (China)

Author keywords

Galactosylation; Lactobacillus bulgaricus L3; Steroidal saponins; galactosidase

Indexed keywords

26 O BETA DEXTRO GALACTOPYRANOSYL (1-6) BETA DEXTRO GLUCOPYRANOSYL 5ALPHA FUROST 3BETA ,22ALPHA TRIOL 12 ONE 3 O BETA DEXTRO GLUCOPYRANOSYL (1-2) [O BETA DEXTRO XYLOPYRANOSYL (1-3)] BETA DEXTRO GLUCOPYRANOSYL (1-4) BETA DEXTRO GALACOTOPYRANOSIDE; 26 O BETA DEXTRO GALACTOPYRANOSYL (1-6) BETA DEXTRO GLUCOPYRANOSYL 5ALPHA FUROST 3BETA ,22ALPHA TRIOL 12 ONE 3 O BETA DEXTRO GLUCOPYRANOSYL (1-2) [O BETA DEXTRO XYLOPYRANOSYL (1-3)] BETA DEXTRO GLUCOPYRANOSYL FUROST 4 EN 22ALPHA,26 DIOL 3,12 DIONE; BETA GALACTOSIDASE; DELTONIN; DICHOTOMIN; DIOSCIN; KHELLIN; PARVIFLOSIDE; POLIANTHOSIDE D; PROTODIOSCIN; SAPONIN DERIVATIVE; SAPONIN II; TERRESTRININ D; TIMOSAPONIN AIII; TIMOSAPONIN BII; TRIGONEOSIDE; TYPASPIDOGENIN; TYPASPIDOSIDE H1; UNCLASSIFIED DRUG; BACTERIAL PROTEIN; GALACTOSE; SAPONIN;

ARTICLE; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG STRUCTURE; ENZYME MECHANISM; ENZYME SPECIFICITY; GALACTOSYLATION; LACTOBACILLUS DELBRUECKII SUBSP. BULGARICUS; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROCESS OPTIMIZATION; STRUCTURE ANALYSIS; ANALOGS AND DERIVATIVES; CHEMISTRY; ENZYMOLOGY; LACTOBACILLUS; METABOLISM;

BACTERIAL PROTEINS; BETA-GALACTOSIDASE; GALACTOSE; LACTOBACILLUS; SAPONINS; SUBSTRATE SPECIFICITY;

EID: 84955473809     PISSN: 02820080     EISSN: 15734986     Source Type: Journal    
DOI: 10.1007/s10719-015-9632-4     Document Type: Article

References (28)

1. Fu, Y.L., Yu, Z.Y., Tang, X.M., Zhao, Y., Yuan, X.L., Wang, S., Ma, B.P., Cong, Y.W.: Pennogenin glycosides with spirostanol structure are strong platelet agonists: structural requirement for activity and mode of platelet agonist synergism. J. Thromb. Haemost. 6, 524-533 (2008)
2. Zhao, Y., Kang, L.P., Liu, Y.X., Liang, Y.G., Tan, D.W., Yu, Z.Y., Cong, Y.W., Ma, B.P.: Steroidal Saponins from the Rhizome of Paris polyphylla and their cytotoxic activities. Planta Med. 75, 356-362 (2009)
3. Li, T.J., Qiu, Y., Yang, P.Y., Rui, Y.C., Chen, W.S.: Timosaponin B-II improves memory and learning dysfunction induced by cerebral ischemia in rats. Neurosci. Lett. 421, 147-151 (2007)
4. Desmet, T., Soetaert, W., Bojarová, P., Křen, V., Dijkhuizen, L., Eastwick-Field, V., Schiller, A.: Enzymatic glycosylation of small molecules: challenging substrates require tailored catalysts. Chem. Eur. J. 18, 10786-10801 (2012)
5. Crout, D.H.G., MacManus, D.A., Critchley, P.: Stereoselective galactosyl transfer to cis-cyclohexa-3, 5-diene-1, 2-diol. J. Chem. Soc. Chem. Commun. 6, 376-378 (1991)
6. Park, A.R., Oh, D.K.: Galacto-oligosaccharide production using microbial β-galactosidase: current state and perspectives. Appl. Microbiol. Biotechnol. 85, 1279-1286 (2010)
7. Oliveira, C., Guimarães, P.M., Domingues, L.: Recombinant microbial systems for improved β-galactosidase production and biotechnological applications. Biotechnol. Adv. 29, 600-609 (2011)
8. Crout, D.H.G., MacManus, D.A., Critchley, P.: Enzymatic synthesis of glycosides using the β-galactosidase of Escherichia coli: regio-and stereo-chemical studies. J. Chem. Soc. Perkin Trans. 1(7), 1865-1868 (1990)
9. Gais, H.J., Zeissler, A., Maidonis, P.: Diastereoselective D-galactopyranosyl transfer to meso diols catalyzed by β-galactosidases. Tetrahedron Lett. 29, 5743-5744 (1988)
10. Van Rantwijk, F., Woudenberg-van Oosterom, M., Sheldon, R.A.: Glycosidase-catalysed synthesis of alkyl glycosides. J. Mol. Catal. B Enzym. 6, 511-532 (1999)
11. Yang, Y.B., Wang, M., Liang, Y., Liang, J.Y.: Transgalactosylation of isotaxiresinol by beta-galactosidase. J. China. Pharmaceut. Univers. 33, 526-528 (2002)
12. Shimizu, R., Shimabayashi, H., Moriwaki, M.: Enzymatic production of highly soluble myricitrin glycosides using β-galactosidase. Biosci. Biotechnol. Biochem. 70, 940-948 (2006)
13. Kim, G.E., Lee, J.H., Jung, S.H., Seo, E.S., Jin, S.D., Kim, G.J., Cha, J., Kim, E.J., Park, K.D., Kim, D.: Enzymatic synthesis and characterization of hydroquinone galactoside using Kluyveromyces lactis lactase. J. Agric. Food Chem. 58, 9492-9497 (2010)
14. Fang, Y., Xu, W., Wu, J., Xu, Z.K.: Enzymatic transglycosylation of PEG brushes by β-galactosidase. Chem. Commun. 48, 11208-11210 (2012)
15. Lu, L.L., Xu, S.Z., Jin, L., Zhang, D.Y., Li, Y.M., Xiao, M.: Synthesis of galactosyl sucralose by β-galactosidase from Lactobacillus bulgaricus L3. Food Chem. 134, 269-275 (2012)
16. Majumder, A.B., Singh, B., Gupta, M.N.: Diastereoselective synthesis of (R)-(alkyl)-β-d-galactopyranoside by using β-galactosidase (Aspergillus oryzae) in low-water media. Bioorg. Med. Chem. Lett. 18, 124-128 (2008)
17. Takayama, S., Shimazaki, M., Qiao, L., Wong, C.H.: Synthesis of lactosamine derivatives usingβ-galactosidase from Bacillus circulans. Bioorg. Med. Chem. Lett. 6, 1123-1126 (1996)
18. Ismail, A., Linder, M., Ghoul, M.: Optimization of butylgalactoside synthesis by β-galactosidase from Aspergillus oryzae. Enzym. Microb. Technol. 25, 208-213 (1999)
19. Santiago, R.D., Fernández-Mayoralas, A., García-Junceda, E.: Enzymatic synthesis of disaccharides by β-galactosidase-catalyzed glycosylation of a glycocluster. J. Mol. Catal. B Enzym. 11, 71-79 (2000)
20. Giacomini, C., Irazoqui, G., Gonzalez, P., Batista-Viera, F., Brena, M.B.: Enzymatic synthesis of galactosyl-xylose by Aspergillusoryzae β-galactosidase. J. Mol. Catal. B Enzym. 159, 19-20 (2002)
21. Nakano, H., Shizuma, M., Murakami, H., Kiryu, T., Kiso, T.: One-pot synthesis of glycosyl poly (arbutin) by enzymatic glycosylation followed by polymerization with peroxidase. J. Mol. Catal. B Enzym. 33, 1-8 (2005)
22. Wang, Y.Z., Feng, B., Huang, H.Z., Kang, L.P., Cong, Y., Zhou, W.B., Zou, P., Cong, Y.W., Song, X.B., Ma, B.P.: Glucosylation of steroidal saponins by syclodextrin glucanotransferase. Planta Med. 76, 1-8 (2010)
23. Zhou, W.B., Feng, B., Huang, H.Z., Qin, Y.J., Wang, Y.Z., Kang, L.P., Zhao, Y., Wang, X.N., Cai, Y., Tan, D.W., Ma, B.P.: Enzymatic synthesis of α-glucosyl-timosaponin BII catalyzed by the extremely thermophilic enzyme: Toruzyme 3.0 L. Carbohydr. Res. 345, 1752-1759 (2010)
24. Lu, L.L., Gu, G.F., Xiao, M., Wang, F.S.: Separation and structure analysis of trisaccharide isomers produced from lactose by Lactobacillus bulgaricus L3 β-galactosidase. Food Chem. 121, 1283-1288 (2010)
25. Lu, L.L., Xu, S.Z., Zhao, R.F., Zhang, D.Y., Li, Z.Y., Li, Y.M., Xiao, M.: Synthesis of galactooligosaccharides by CBD fusion β-galactosidase immobilized on cellulose. Bioresour. Technol. 116, 327-333 (2012)
26. Ma, B.P., Dong, J.X., Wang, B.J., Yan, X.Z.: New Spirostanol Glycosides from Anemarrhena asphodeloides. Acta Pharm. Sin. 31, 271-277 (1996)
27. Jin, J.M., Zhang, Y.J., Yang, C.R.: Spirostanol and furostanol glycosides from the fresh tubers of Polianthes tuberosa. J. Nat. Prod. 67, 5-9 (2004)
28. Kang, L.P., Wu, K.L., Yu, H.S., Pang, X., Liu, J., Han, L.F., Zhang, J., Zhao, Y., Xiong, C.Q., Song, X.B., Liu, C., Cong, Y.W., Ma, B.P.: Steroidal saponins from Tribulus terrestris. Phytochemistry 107, 182-189 (2014)