Environmentally benign synthesis of natural glycosides using apple seed meal as green and robust biocatalyst

Journal of Biotechnology

Volumn 133, Issue 4, 2008, Pages 469-477

  Yu, Hui Lei ^a   Xu, Jian He ^a   Lu, Wen Ya ^b   Lin, Guo Qiang ^b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Apple seed meal; Biocatalysis; Glycoside synthesis; Green chemistry; Salidroside

Indexed keywords

APPLE SEED MEAL; GREEN CHEMISTRY;

ALUMINA; BIOCATALYSTS; CROSSLINKING; FRUITS; MICROWAVES; SYNTHESIS (CHEMICAL);

SEED;

4 METHOXYBENZYL O BETA DEXTRO GLUCOPYRANOSIDE; AGLYCONE; CINNAMYL O BETA DEXTRO GLUCOPYRANOSIDE; GLUCOSIDE; GLYCOSIDE; SALIDROSID; TERT BUTYL ALCOHOL; UNCLASSIFIED DRUG;

ADSORPTION; ARTICLE; BIOCATALYST; BIOREACTOR; CARBOHYDRATE ANALYSIS; CHEMICAL REACTION; CROSS LINKING; FOOD PROCESSING; MEAL; NONHUMAN; PRIORITY JOURNAL; PROTEIN IMMOBILIZATION; PROTEIN STRUCTURE;

ALUMINUM OXIDE; CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLUCOSIDASES; GLUCOSIDES; GLYCOSIDES; MALUS; MICROSCOPY, ELECTRON, SCANNING; MOLECULAR STRUCTURE; PHENOLS; SEEDS;

MALUS X DOMESTICA;

EID: 38749090539     PISSN: 01681656     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jbiotec.2007.12.003     Document Type: Article

References (26)

1. Ahmed F., Stein A., and Lye G.J. In situ product removal to enhance the yield of biocatalytic reactions with competing equilibria: α-glucosidase catalysed synthesis of disaccharides. J. Chem. Technol. Biotechnol. 76 (2001) 971-977
2. Akita H., Kurashima K., Nakamura T., and Kato K. Chemoenzymatic synthesis of naturally occurring β-glucosides. Tetrahedron Asymmetry 10 (1999) 2429-2439
3. Akita H., Kawahara E., Kishida M., and Kato K. Synthesis of naturally occurring β-d-glucopyranoside based on enzymatic β-glycosidation. J. Mol. Catal. B: Enzym. 40 (2006) 8-15
4. Azerad R. Editorial overview: better enzymes for green chemistry. Curr. Opin. Biotechnol. 12 (2001) 533-534
5. Bonanome A., Pagnan A., Caruso D., Toia A., Xamin A., and Fedeli E. Evidence of postprandial absorption of olive oil phenols in humans. Nutr. Metab. Cardiovasc. Dis. 10 (2000) 111-120
6. Centi G., and Perathoner S. Catalysis and sustainable (green) chemistry. Catal. Today 77 (2003) 287-297
7. Darbinyan V., Kteyan A., Panossian A., Gabrielian E., Wikman G., and Wagner H. Rhodiola rosea in stress induced fatigue-a double blind cross-over study of a standardized extract SHR-5 with a repeated lowdose regimen on the mental performance of healthy physicians during night duty. Phytomedicine 7 (2000) 365-371
8. de Roode B.M., van Beek J.A., van der Padt M.C., Franssen R., and Boom R.M. The integrated enzymatic production and downstream processing of hexyl glucoside. Enzyme Microb. Technol. 29 (2001) 513-520
9. de Roode B.M., Olihoek L., van der Padt A., Franssen M.C.R., and Boom R.M. Downstream processing of enzymatically produced geranyl glucoside. Biotechnol. Prog. 17 (2001) 881-886
10. Faber K., and Patel R. Chemical biotechnology: a happy marriage between chemistry and biotechnology: asymmetric synthesis via green chemistry. Curr. Opin. Biotechnol. 11 (2000) 517-519
11. Lee M.W., Lee Y.A., Park H.M., Toh S.H., Lee E.J., and Jang H.D. Antioxidative phenolic compounds from the roots of Rhodiola sachalinensis A. Bor. Arch. Pharm. Res. 23 (2000) 455-458
12. Linh P.T., Kim Y.H., Hong S.P., Jian J.J., and Kang J.S. Quantitative determination of salidroside and tyrosol from the underground part of Rhodiola rosea by high performance liquid chromatography. Arch. Pharm. Res. 23 (2000) 349-352
13. Ming H.Q. The synthesis of salidroside and its pharmacological properties. Chin. J. Pharm. Bull. 21 6 (1986) 373-375
14. Ming H.Q., Xia G.C., and Zhang R.D. Advanced research on Rhodiola. Chin. Traditional Herb. Drugs 19 5 (1988) 229-234
15. Saratikov A.S. Rhodioloside, a new glycoside from Rhodiola rosea and its pharmacological properties. Die Pharmazie 69 (1968) 394-398
16. Tong A.M., Lu W.Y., Xu J.H., and Lin G.Q. Use of apple seed meal as a new source of β-glucosidase for enzymatic glucosylation of 4-substituted benzyl alcohols and tyrosol in monophasic aqueous-dioxane medium. Bioorg. Med. Chem. Lett. 14 (2004) 2095-2097
17. Tong A.M., Lu W.Y., Xu J.H., and Lin G.Q. Construction and optimization of a monophasic organic-water system for enzymatic synthesis of ρ-nitrobenzyl β-d-glucopyranosides by reverse hydrolysis. J. Mol. Catal. B: Enzymatic 32 (2005) 83-88
18. Troshchenko J. Synthesis of glucoside of 2-(p-hydroxyphenyl)-ethanol (tyrosol). Khim. Prir. Soedin. (Russian) 5 4 (1969) 256-260
19. Udintsev S.N., and Schakhov V.P. Decrease of cyclophosphamide haematotoxicity by Rhodiola rosea root extract in mice with Ehrlich and Lewis transplantable tumors. Eur. J. Cancer 27 (1991) 1182
20. Wu S.X., Zu Y.G., and Wu M. High yield production of salidroside in the suspension culture of Rhodiola sachalinensis. J. Biotechnol. 106 (2003) 33-43
21. Xu J.F., Su Z.G., and Feng P.S. Activity of tyrosol glucosyltransferase and improved salidroside production through biotransformation of tyrosol in Rhodiola sachalinensis cell cultures. J. Biotechnol. 61 (1998) 69-73
22. Xu J.F., Liu C.B., Han A.M., Feng P.S., and Su Z.G. Strategies for the improvement of salidroside production in cell suspension cultures of Rhodiola sachalinensis. Plant Cell Rep. 17 (1998) 288-293
23. Yi Q., Sarney D.B., Khan J.A., and Vulfson E.N. A novel approach to biotransformations in aqueous-organic two-phase systems: enzymatic synthesis of alkyl β-d-glucosides using microencapsulated β-glucosidase. Biotechnol. Bioeng. 60 (1998) 387-390
24. Yu H.L., Xu J.H., Lu W.Y., and Lin G.Q. Identification, purification and characterization of β-glucosidase from apple seed as a novel catalyst for synthesis of O-glucosides. Enzyme Microb. Technol. 40 (2007) 354-361
25. Zhang L., Somasundaran P., and Maltesh C. Adsorption of n-dodecyl-β-d-maltoside on solids. J. Colloid Interface Sci. 191 (1997) 202-208
26. Zhang C.Z., Yu H.S., Lu M.C., Li J., and Jin F.X. Enzymic synthesis of salidroside: purification and characterization of salidrosidase from Aspergillas niger. Process Biochem. 40 (2005) 3143-3147