Skip to main content
SpringerLink
Log in
Book cover

Enzymatic Transformation pp 137–214Cite as

Glycosylation of Some Selected Phenols and Vitamins

  • Chapter
  • First Online:

  • 1343 Accesses

Abstract

Section 8.1 describes the synthesis of glycosides of water-insoluble phenols such as guaiacol, eugenol, curcumin, N-vanillyl-nonanamide and capsaicin and water-soluble phenols like vanillin, dl-dopa, l-dopa, dopamine, serotonin and epinephrine with carbohydrates: d-glucose, d-galactose, d-mannose, d-fructose, d-arabinose, d-ribose, maltose, sucrose, lactose, d-mannitol and d-sorbitol.

Section 8.2 deals with enzymatic syntheses of more water-soluble thiamin (vitamin B1), riboflavin (vitamin B2) and pyridoxine (vitamin B6) and fat-soluble retinol (vitamin A), ergocalciferol (vitamin D2), cholecalciferol (Vitamin D3) and α-tocopherol (vitamin E). The reactions were investigated and discussed (Chap. 9) in terms of incubation period, pH, buffer, enzyme and substrate concentrations and regio- and stereoselectivity.

This is a preview of subscription content, log in via an institution.

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   129.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

References

  • Akao T, Yoshino T, Kobashi K, Hatlori M (2002) Evaluation of salicin as an antipyretic prodrug that does not cause gastric injury. Planta Med 68:714–718

    Article  PubMed  CAS  Google Scholar 

  • Andreotti G, Giordano A, Tramice A, Mollo E, Trincone A (2006) Hydrolyses and transglycosylations performed by purified α-D-glucosidase of the marine mollusk Aplysia fasciata. J Biotechnol 122:274–284

    Article  PubMed  CAS  Google Scholar 

  • Andrews RS, Pridham JB (1965) Structure of dopa glucoside from Vicia faba. Nature 205:1213–1214

    Article  CAS  Google Scholar 

  • Angerlacenci M (2007) Dopamine dysregulation of ­movement control in L-dopa induced dyskinesia. Trends Neurosci 30(5):236–243

    Article  CAS  Google Scholar 

  • AOAC Official Methods of Analysis (1995) Chapter 46. 16th edn, vol II, p 12

    Google Scholar 

  • Asano Y, Wada K (2003) Regioselective glucosylation of pyridoxine by microorganisms. Biosci Biotechnol Biochem 67:499–507

    Article  PubMed  CAS  Google Scholar 

  • Audus KL, Chikhale PJ, Miller WD, Thompson SE, Borchardt RT (1992) Brain uptake of drugs. The influence of chemicals and biological factors. Adv Drug Res 23:1–64

    CAS  Google Scholar 

  • Bacher A, Eberhardt S, Fischer M, Kis K, Richter G (2000) Biosynthesis of vitamin B2 (riboflavin). Annu Rev Nutr 20:153–167

    Article  PubMed  CAS  Google Scholar 

  • Bates C (1993) Riboflavin. Int J Vitam Nutr Res 63:274–277

    PubMed  CAS  Google Scholar 

  • Berger M, Gray JA, Roth C (2009) The expanded biology of serotonin. Ann Rev Med 60:355–366

    Article  PubMed  CAS  Google Scholar 

  • Bhabadesh C, Somnath M, Dehdas B, De Amit K (1996) Capsaicin a unique antioxidant, antifungal, anti-inflammatory analgesic compound with antifungal activity against dermatophytes. Med Sci Res 24:669–670

    Google Scholar 

  • Burri J, Graf M, Lambelet P, Loliger J (1999) Vanillin more than a flavoring agent – a potential antioxidant. J Sci Food Agric 48:49–56

    Article  Google Scholar 

  • Burton GW, Joyce A, Ingold KU (1983) Is vitamin E the only lipid soluble, chain-breaking antioxidant in human blood plasma and erythrocyte membrane. Arch Biochem Biophys 221:281–290

    Article  PubMed  CAS  Google Scholar 

  • Chahid Z, Montet D, Pina M, Graille J (1992) Effect of water activity on enzymatic synthesis of alkylglycosides. Biotechnol Lett 14(4):281–284

    Article  CAS  Google Scholar 

  • Chen CW, Ou-Yang C-C, Yeh C-W (2003) Synthesis of galactooligosaccharides and transgalactosylation modeling in reverse micelles. Enzyme Microb Technol 33:497–507

    Article  CAS  Google Scholar 

  • Chen IJ, Yang JM, Yeh JL, Wu BN, Lo YC, Chen SJ (1992) Hypotensive and antinociceptive effects of ether linked and relatively non pungent analogs of N-nonanoyl-vanillylamide. Eur J Med Chem 27:187–192

    Article  CAS  Google Scholar 

  • Chiba S (1997) Molecular mechanism in α-glucosidase and glucoamylase. Biosci Biotech Biochem 61:1233–1239

    Article  CAS  Google Scholar 

  • Clark AM (1996) Natural products as a resource for new drugs. Pharm Res 13:1133–1141

    Article  PubMed  CAS  Google Scholar 

  • Dalpiaz A, Filosa R, de Caprariis P, Conte G, Bortolotti F, Biondi C, Scatturin A, Prasad PD, Pavanc B (2007) Molecular mechanism involved in the transport of a prodrug dopamine glycosyl conjugate. Int J Pharm 336:133–139

    Article  PubMed  CAS  Google Scholar 

  • Dickerson TJ, Yamamoto N, Janda Kim D (2004) Antibody-catalysed oxidative degradation of nicotine using riboflavin. Bio Org Med Chem 12:4981–4987

    Article  CAS  Google Scholar 

  • Du Y, Wei G, Linhardt RJ (2004) Total synthesis of quercetin 3-sophorotrioside. J Org Chem 69:2206–2209

    Article  PubMed  CAS  Google Scholar 

  • Einstein Charles R, Divakar S (2009) β-Glucosidase catalyzed syntheses of pyridoxine glycosides. Biosci Biotech Biochem 73:233–236

    Article  CAS  Google Scholar 

  • Einstein Charles R, Ponrasu T, Udaya Sankar K, Divakar S (2009a) Syntheses of retinol glycosides using β-glucosidase in SCCO2 media. Appl Biochem Biotech 159:199–207

    Article  CAS  Google Scholar 

  • Einstein Charles R, Ponrasu T, Sivakumar R, Divakar S (2009b) Angiotensin converting enzyme inhibitory and antioxidant activities of enzymatically synthesized phenolic and vitamin glycosides. Biotech Appl Biochem 52:177–184

    Article  CAS  Google Scholar 

  • Feldman D, Xiao-Yan Z, Krishnan AV (2000) Vitamin D and prostate cancer. Endocrinology 141:5–9

    Article  PubMed  CAS  Google Scholar 

  • Fernandez C, Nieto O, Fontenla JA, Rivas E, de Ceballos ML, Fernandez-Mayoralas A (2003) Synthesis of glycosyl derivatives as dopamine prodrugs Interaction with glucose carrier GLUT-1. Org Biomol Chem 1:767–771

    Article  PubMed  CAS  Google Scholar 

  • Fitzgerald DJ, Stratford M, Gasson MJ, Narbad A (2005) Structure function analysis of the vanillin molecule and its antifungal properties. J Agric Food Chem 53:1769–1775

    Article  PubMed  CAS  Google Scholar 

  • Frandsen TP, Dupont C, Lehmbeck J, Stoffer B, Sierks MR, Honzatko RB, Svensson B (1994) Site-directed mutagenesis of the catalytic base Glutamic acid 400 in glucoamylase from Aspergillus niger and of Tyrosine 48 and Glutamine 401, both hydrogen bonded to the gamma-carboxylate group of Glutamic acid 400. Biochemistry 33:13808–13816

    Article  PubMed  CAS  Google Scholar 

  • Gannett PM, Nagel DL, Reilly PJ, Lawson T, Sharpe J, Toth B (1988) The capsaicinoids their separation, synthesis and mutagenicity. J Org Chem 53:1064–1071

    Article  CAS  Google Scholar 

  • Geng X, Song L, Pu X, Tu P (2004) Neuroprotective effects of phenylethanoid glycosides from Cistanches salsa against 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced dopaminergic toxicity in C57 Mice. Biol Pharm Bull 27(6):797–801

    Article  PubMed  CAS  Google Scholar 

  • Geng X, Tian X, Tu P, Pu X (2007) Neuroprotective effects of echinacoside in the mouse MPTP model of Parkinson’s disease. Eur J Pharmacol 564:66–74

    Article  PubMed  CAS  Google Scholar 

  • Giri A, Dhingra V, Giri CC, Singh A, Ward OP, Narasu ML (2001) Biotransformations using plant cells, organ cultures and enzyme systems current trends and future prospects. Biotechnol Adv 19:175–199

    Article  PubMed  CAS  Google Scholar 

  • Gomes DCF, Alegrio LV, Leon LL, de Lima MEF (2002) Total synthesis and anti-leishmanial activity of some curcumin analogues. Arzneim-Forsch 52:695–698

    Google Scholar 

  • Guggenheim M (1913) Dioxyphenylalanine neue Aminosaureaus Vicia faba. Hoppe-Seylers’s Zeitschr Physiol Chem 88:276–284

    Article  Google Scholar 

  • Hamada H, Tomi R, Asada Y, Furuya T (2001) Phytoremediation of bisphenol A by cultured suspension cells of Eucalyptus perriniana regioselective hydroxylation and glycosylation. Tetrahedron Lett 43:4087–4089

    Article  Google Scholar 

  • Hamada H, Nishida K, Furuya T, Ishihara K, Nakajima N (2002) Preparation of a new pepper chemoenzymatic synthesis of capsaicin oligosaccharide and 8-nordihydrocapsaicin. J Mol Catal B: Enzym 16:115–119

    Article  Google Scholar 

  • Hamada H, Ohiwa S, Nishida T, Katssuragi H, Takeda T, Hamada H, Nakajima N, Ishihara K (2003) One step glucosylation of capsaicinoids by cultured cells of Phytolacca americana. Plant Biotechnol 20:253–255

    Article  CAS  Google Scholar 

  • Hausslera MR, Wasserman RH, McCaina TA, Peterlik M, Bursaca KM, Hughesa MR (1976) 1,25-Dihydroxyvitamin D3-glycosides Identification of a calcinogenic principle of Solanum malacoxylon. Life Sci 18(10):1049–1056

    Article  Google Scholar 

  • Heyes Z, Szabo A, Nemeth J, Jakab B, Pinter E, Banvolgyl A, Kereskai L, Keri G, Szolcsanyl J (2004) Antiiflammatory and analgesic effects of somatostatin released from chronic arthritis model in the rat. Arthritis Rheum 50:1677–1685

    Article  CAS  Google Scholar 

  • Holick MF (2004) Sunlight and vitamin D for bone health and prevention of autoimmune diseases, cancers, and cardiovascular disease. Am J Clin Nutr 6:1678S–1688S

    Google Scholar 

  • Houghton LA, Vieth R (2006) The care against ergocalciferol (vitamin D2) as a vitamin supplement. Am J Clin Nutr 84:694–697

    PubMed  CAS  Google Scholar 

  • Hoyer D, Martin G (1997) 5-HT receptor classification and nomenclature towards a harmonization with the human genome. Neuropharmacology 36(4–5):419–428

    Article  PubMed  CAS  Google Scholar 

  • Ichikawa H, Yoshida N, Takano H, Ishikawa T, Handa O, Takagi T, Nito Y, Murase H, Yoshikawa T (2003) A novel water-soluble vitamin E derivative (TMG) protects against gastric mucosal damage induced by ischemic and reperfusion in rats. Dig Sci 48(1):54–58

    Article  CAS  Google Scholar 

  • Iorizzi M, Lanzotti V, De Marino S, Zollo F, Blanco-Molina M, Macho A, Munoz E (2001) New glycosides from Capsicum annum L. Var. accuminatum. Isolation, structure determination and biological activity. J Agric Food Chem 49:2022–2029

    Article  PubMed  CAS  Google Scholar 

  • Isozaki Y, Yoshida N, Ichikawa H, Kuroda M, Kokura S, Naito Y, Okanoue T, Yoshikawa T (2005) A novel water-soluble vitamin E derivative protect against aspirin-induced gastric mucosal injury in rats. Int J Mol Med 16(6):1035–1040

    PubMed  CAS  Google Scholar 

  • James SY, Williams MA, Newland AC, Colston KW (1999) Leukemia cell differentiation cellular and molecular interactions of retinoids and vitamin D. Gen Pharmacol 32:143–154

    Article  PubMed  CAS  Google Scholar 

  • Jones BJ, Blackburn TP (2002) The medical benefit of 5-HT research. Pharmcol Biochem Behav 71(4):555–681

    Article  CAS  Google Scholar 

  • Kaljuzhin OV, Shkalev MV (2000) Immunomodulator and pharmaceutical compositions with antitumor properties, and a food additive. Patent EP1038532 (CA 129 335732)

    Google Scholar 

  • Kaminaga Y, Nagatsu A, Akiyama T, Sugimoto N, Yamazaki T, Maitani T, Mizukami H (2003) Production of unnatural glucosides of curcumin with drastically enhanced water solubility by cell suspension cultures of Catharanthus roseus. FEBS Lett 555:311–316

    Article  PubMed  CAS  Google Scholar 

  • Kang K, Park S, Kim YS, Lee S, Back K (2009) Biosynthesis and biotechnological production of serotonin derivatives. Appl Micorb Biotechnol 83(1):27–34

    Article  CAS  Google Scholar 

  • Katrien T, Miloslav P, Sophie S, Guy E, Yvette M (1997) New antioxidant mixture for long term stability of serotonin, dopamine and their metabolites in automated microbore liquid chromatography with dual electrochemical detection. J Chromatograph B Biomed Sci Appl 694(2):297–303

    Article  Google Scholar 

  • Kawada T, Watanabae T, Takahashi T, Tanaka T, Iwai K (1986) Effects of capsaicin on lipid metabolism in rats fed a high fat diet. J Nutr 116:1272–1278

    PubMed  CAS  Google Scholar 

  • Kawai F, Yamada H, Ogata K (1971a) Properties of pyridoxine glucoside. J Vitaminol 17:121–124

    Article  CAS  Google Scholar 

  • Kawai F, Yamada H, Ogata K (1971b) Studies on transglycosidation to vitamin B6 by microorganisms Part IV. Purification of a bacterial enzyme catalyzing pyridoxine glucoside synthesis. Agric Biol Chem 35:184–190

    Article  CAS  Google Scholar 

  • Kempster PA, Bogetic Z, Secombei JW, Martin HD, Balazs NDH, Wahlquist MC (1993) Motor effect ofbroad beans Vicia faba in Parkinson’s disease Single dose studies. Asia Pacific J Clin Nutr 2:85–89

    Google Scholar 

  • Kometani T, Tanimoto H, Nishimura T, Kanbara I, Okada S (1993a) Glucosylation of capsaicin by cell suspension cultures of Coffea arabica. Biosci Biotech Biochem 57:2192–2193

    Article  CAS  Google Scholar 

  • Kometani T, Tanimoto H, Nishimura T, Okada S (1993b) Glucosylation of vanillin by cultured plant cells. Biosci Biotech Biochem 57:1290–1293

    Article  CAS  Google Scholar 

  • Kondo Y, Shimoda K, Takimura J, Hamada H, Hamada H (2006) Glycosylation of vitamin E homologue by cultured plant cells. Chem Lett 35:324–326

    Article  CAS  Google Scholar 

  • Kren V (2001) Chemical biology and biomedicine of glycosylated natural compounds. In: Fraser-Reid B, Tatsuta K, Thiem J (eds) Glycoscience chemistry and chemical biology. Springer, Berlin, 3: 2471-2529

    Google Scholar 

  • Kren V, Martinkova L (2001) Glycosides in medicine: the role of glycosidic residue in biological activity. Curr Med Chem 8:1303–1328

    Article  PubMed  CAS  Google Scholar 

  • Kren V, Hunkova Z, Halada P, Suzuki Y (1998) Transglycosylation of thiamine by fungal β-N-Acetylhexosaminidases. Biosci Biotechnol Biochem 62(12):2415–2417

    Article  CAS  Google Scholar 

  • Lahmann M, Thiem J (1997) Synthesis of α-tocopheryl oligosaccharides. Carbohydr Res 299:23–31

    Article  PubMed  CAS  Google Scholar 

  • Lan T, Dalip R, Errol MY (2004) Isolation and purification of the hypoglycemic principle present in Cap. frutescens. Phytotherap Res 18:95–96

    Article  CAS  Google Scholar 

  • LeBlane JG, Burgees C, Sesma F, de Giori GS, Van Sinderen D (2005) Lactococcus lactis is capable of improving the riboflavin status in deficient rats. British J Nutr 94:262–267

    Article  CAS  Google Scholar 

  • Lee Y, Howard LR, Villalon B (1995) Flavonoids and antioxidant activity of fresh pepper (C. annum) cultivars. J Food Sci 60:473–476

    Article  CAS  Google Scholar 

  • Lehninger LA (1977) Biochemistry, 3rd edn. Worth Publishers Inc., New York, pp 355–357

    Google Scholar 

  • Lopez-Malo A, Alzamora SM, Argaiz A (1998) Vanillin and pH synergistic effects on mold growth. J Food Sci 63:143–146

    Article  CAS  Google Scholar 

  • Madrid Y, Langer LF, Brem H, Langer R (1991) New directions in the delivery of drugs and other substances to the central nervous system. Adv Pharmacol 22:299–324

    Article  PubMed  CAS  Google Scholar 

  • Manohar B, Divakar S (2010) Enzymatic synthesis of cholecalciferol glycosides. J Food Sci Technol 46(5):469–475

    Article  CAS  Google Scholar 

  • Marieb EN (2009) Essentials of human anatomy and physiology, 8th edn. Pearson/Benjamin Cummings, San Fransisco, p 336. ISBN 321-51342-8

    Google Scholar 

  • Marty A, Chulalaksananukul W, Condoret JS, Willemont RM, Durand G (1990) Comparison of lipase-catalyzed esterification in supercritical carbon dioxide and n-hexane. Biotechnol Lett 12(1):11–16

    Article  CAS  Google Scholar 

  • Matondo RB, Punt C, Homberg J, Toussaint MJ, Kisjes R, Korporaal SJ, Akkerman JW, Cuppen E, de Bruin A (2009) Deletion of the serotonin transporter in rats disturbs serotonin homeostasis without impairing liver regeneration. Am J Physiol Gastrointest Liver Physiol 296(4):G963–G968

    Article  PubMed  CAS  Google Scholar 

  • Maurizio C, Kati O, Maria O, Sabrina P, Bruno S (2007) Vitamin D in rheumatoid arthritis. Autoimmun Rev 7:59–64

    Article  CAS  Google Scholar 

  • Mello JRB (2003) Calcinosis-calcinogenic plants. Toxicon 41:1–12

    Article  PubMed  CAS  Google Scholar 

  • Mohri K, Watanabe Y, Yoshida Y, Satoh M, Isobe K, Sugimoto N, Tsuda Y (2003) Synthesis of glycosylcurcuminoids. Chem Pharm Bull 51:1268–1272

    Article  PubMed  CAS  Google Scholar 

  • Moon JH, Terao J (1998) Antioxidant activity of caffeic acid and dihydrocaffeic acid in Lard and human low-density lipoprotein. J Agri Food Chem 46: 5062–5065

    Article  CAS  Google Scholar 

  • Morre DJ, Chueh PJ, Morre DM (1995) Capsaicin inhibits preferentially the NADH oxidase and growth of transformed cells in culture. Proc Natl Acad Sci USA 92:1831–1835

    Article  PubMed  CAS  Google Scholar 

  • Murase H, Yamauchi R, Kato K, Kunieda T, Terao J (1997) Synthesis of a novel vitamin E derivative, 2-(α-D-glucopyranosyl) methyl-2,5,7,8-tetramethyl chroma- 6-ol transglycosylation. Lipids 32:73–78

    Article  PubMed  CAS  Google Scholar 

  • Nagasawa T, Takagi H, Kawakami K, Suzuki T, Shahaghi Y (1961) The browning compounds of bean III isolation of dopa-O-β-D-glucoside and the enzymic mechanism for the color change of broad bean. Agric Biol Chem 25:441–447

    CAS  Google Scholar 

  • Nsoukpoe-Kossi CN, Sedaghat-Herati R, Ragi C, Hotchandani S, Tajmir-Riahi HA (2007) Retinol and retinoic acid bind human serum albumin: stability and structural features. Int J Biol Macromol 40:484–490

    Article  CAS  Google Scholar 

  • Ochiai J, Takano H, Ichikawa H, Naito Y, Yoshida N, Yanagisawa R, Yoshino S, Murase H, Yoshikawa T (2002) A novel water-soluble vitamin E derivative, 2-(α-D-glucopyranosyl)methyl-2,5,7,8-tetramethylchroman-6-ol, protects against acute lung injury and mortality in endotoxemic rats. Int J Mol Med 18(6):580–584

    Google Scholar 

  • Ohnuki K, Haramizu S, Oki K, Watanabe T, Yazawa S, Fushiki T (2001) Administration of capsiate, a non-pungent capsaicin analog, promotes energy metabolism and suppresses body fat accumulation in mice. Biosci Biotechnol Biochem 65:2735–2740

    Article  PubMed  CAS  Google Scholar 

  • Ong DE, Newcomer ME, Chytil F (1994) Biology chemistry and medicine. In: Sporn MB, Roberts AB, Goodman DS (eds) The retinoids. Raven Press Ltd., New York, pp 283–318

    Google Scholar 

  • Ooi Y, Hashimoto T, Mitsuo N, Satoh T (1985) Enzymatic formation of β-galactosidase from Aspergillus oryzae and its application to the synthesis of chemically unstable cardiac glycosides. Chem Pharm Bull 33:1808–1814

    Article  CAS  Google Scholar 

  • Orihara Y, Furuya T, Hashimoto N, Deguchi Y, Tokoro K, Kanisawa T (1992) Biotransformation of isoeugenol and eugenol by cultured cells of Eucalyptus perriniana. Phytochemistry 31:827–831

    PubMed  CAS  Google Scholar 

  • Pardridge WM (2002) Targeting neurotherapeutic agents through the blood–brain barrier. Arch Neurol 59:35–40

    Article  PubMed  Google Scholar 

  • Peehl DM, Krishnan AV, Feldman D (2003) Pathways mediating the growth-inhibitory actions of vitamin D in prostate cancer. J Nutr 133:2461–2469

    Google Scholar 

  • Ponrasu T, Charles RE, Sivakumar R, Divakar S (2008) Syntheses of α-tocopheryl glycosides by glucosidases. Biotechnol Lett 30:1431–1439

    Article  PubMed  CAS  Google Scholar 

  • Ponrasu T, Manohar B, Divakar S (2009) A response ­surface methodological study on prediction of glucosylation yields of thiamin using immobilized β- glucosidase. Process Biochem 44:251–255

    Article  CAS  Google Scholar 

  • Powers HJ (2003) Riboflavin and health. Am J Clin Nutr 77:1352–1360

    PubMed  CAS  Google Scholar 

  • Pras N, Woerdenbag J, Van Uden W (1995) Bioconversion potential of plant enzymes for the production of pharmaceuticals. Plant Cell Tissue Org Cult 43:117–121

    Article  CAS  Google Scholar 

  • Rashid MH, Inoue M, Kondo S, Kawashima T, Bakoshi S, Ueda H (2003) Novel expression of vanilloid receptor I on capsaicin-insensitive fibres accounts for the analgesic effect of capsaicin in neuropathic pain. J Pharmacol Exp Ther 304:940–948

    Article  PubMed  CAS  Google Scholar 

  • Reichel L, Sckickle R (1943) Synthesen neuer methoxylierter Chalkon-Flavanon-glucoside unter physiologischen Bedingungen. Chemie und Biochemie der Pflanzenstoffe, XII. Mitteilung Plant Chem 76B:1134–1137

    CAS  Google Scholar 

  • Robyt JF (1998) Essentials of carbohydrate chemistry. Springer, New York, pp 64–68

    Book  Google Scholar 

  • Roode BM, Franssen MCR, van der Padt A, Boom RM (2003) Perspective for the industrial enzymatic production of glycosides. Biotechnol Prog 19:1391–1402

    Article  PubMed  CAS  Google Scholar 

  • Russell AJ, Beckman EJ (1991) Should the high diffusivity of a supercritical fluid increase the rate of an enzyme-catalyzed reaction? Enzyme Microbiol Technol 13(12):1007–1007

    Article  CAS  Google Scholar 

  • Sasaki N, Adachi T, Koda T, Ozeki Y (2004) Detection of UDP-glucose Cyclo-dopa 5-O-glucosyltransferase activity in four O’ clocks (Mirabilis jalapa L.). FEBS Lett 568:159–162

    Article  PubMed  CAS  Google Scholar 

  • Sato T, Takeuchi H, Takahashi K, Kurosu J, Yoshida K, Tsugane T, Shimura S, Kino K, Kirimura K (2003) Selective α-glucosylation of eugenol by α-glucosyl transfer enzyme of Xanthomonas campestris WU-9701. J Biosci Bioeng 96:199–202

    PubMed  CAS  Google Scholar 

  • Satoh T, Miyataka H, Yamamoto K, Hirano K (2001) Synthesis and physiological activity of novel tocopheryl glycosides. Chem Pharm Bull 49(8):948–953

    Article  PubMed  CAS  Google Scholar 

  • Schmid B, Kotter I, Heide L (2001) Pharmacokinetics of salicin after oral administration of a standard willow bark extract. Eur J Clinic Pharmacol 57:387–391

    Article  CAS  Google Scholar 

  • Scholz D, Mebel M, Topelmann J, Grossmann I, Scholze J, Mrochen H (1983) Prevention of osteonecrosis following renal transplantation by using vitamin D2 (ergocalciferol). Proc Eur Dial Transplant Assoc 20:331–337

    PubMed  CAS  Google Scholar 

  • Sengodan S, Palanivel S, Panchanadham S (2003) Curative effect of riboflavin, niacin and ascorbic acid on tamoxifen mediated endometrial carcinoma bearing Sprage-Dawley rats with reference to lipid peroxidation and antioxidant status. J Clin Biochem Nutr 33:39–45

    Article  Google Scholar 

  • Shetty P, Atallah MT, Shetty K (2002) Effects of UV treatment on the proline-linked pentose phosphate pathway for phenolics and L-DOPA synthesis in dark germinated Vicia faba. Process Biochem 37:1285–1295

    Article  CAS  Google Scholar 

  • Shimoda K, Konda Y, Abe K, Hamada H, Hamada H (2006) Formation of water-soluble vitamin derivatives from lipophilic vitamins by cultured plant cells. Tetrahedron Lett 47:2695–2698

    Article  CAS  Google Scholar 

  • Sierks MR, Ford C, Reilly PJ, Svensson B (1990) Catalytic mechanism of fungal glucoamylases as defined by mutagenesis of Asp 176, Glu179, and Glu180 in the enzyme from Aspergillus awamori. Protein Eng 3:193–198

    Article  PubMed  CAS  Google Scholar 

  • Sircar S (2007) Medical physiology. Thieme Publishing Group, Stuttgart, p 536. ISBN 3-13-144061-9

    Google Scholar 

  • Sivakumar R, Divakar S (2006) Glycosylation of vanillin by amyloglucosidase in organic media. Tetrahedron Lett 47:695–699

    Article  CAS  Google Scholar 

  • Sivakumar R, Divakar S (2007) Syntheses of N-vanillyl-nonanamide glycosides using amyloglucosidase from Rhizopus mold and β-glucosidase from sweet almond. Biotechnol Lett 29:1537–1548

    Article  PubMed  CAS  Google Scholar 

  • Sivakumar R, Divakar S (2009a) Enzymatic syntheses of dopamine glycosides. Enzyme Microb Technol 44:33–39

    Article  CAS  Google Scholar 

  • Sivakumar R, Divakar S (2009b) Amyloglucosidase from Rhizopus mold and β- glucosidase from sweet almond catalysed syntheses of riboflavinyl glycosides. Indian J Biotechnol 8:400–407

    CAS  Google Scholar 

  • Sivakumar R, Manohar B, Divakar S (2006a) Synthesis of vanillyl-maltoside using glucosidases by response surface methodology. Eur Food Res Technol 226:255–263

    Article  CAS  Google Scholar 

  • Sivakumar R, Vijayakumar GR, Manohar B, Divakar S (2006b) Competitive substrate inhibition of amyloglucosidase from Rhizopus mold by vanillin and curcumin in respective glucosylation reactions. Biocatal Biotrans 24:299–305

    Article  CAS  Google Scholar 

  • Sivakumar R, Ponrasu T, Divakar S (2009) Syntheses of DL-dopa glycosides using glucosidases. Glycoconj J 26:199–209

    Article  PubMed  CAS  Google Scholar 

  • Smith DC, Johnson CS, Freeman CC, Muindi J, Wilson JW, Trump DL (1999) A phase I trial of calcitriol (1,25-dihydroxycholecalciferol) in patients with advanced malignancy. Clin Cancer Res 5:1339–1345

    PubMed  CAS  Google Scholar 

  • Sommer J, Schroeder C, Stockigt J (1997) In vivo formation of vanillin glucoside. Plant Cell Tiss Org Cult 50:119–123

    Article  CAS  Google Scholar 

  • Sophie L, Robert G, Pierre K (2004) A new method of solvent free O – and N – glycosilation using activated carbon fibers (ACF) as a promoter. Applications to the synthesis of saponin and nucleoside analogues. Chem Commun 5:586–587

    Google Scholar 

  • Stephan D, Peter K (2003) Vanillins – a novel family of DNA-PK inhibitors. Nucleic Acid Res 31:5501–5512

    Article  CAS  Google Scholar 

  • Studart MT, Raschle T, Forster G, Amrhein N, Fitzpatrick TB (2005) Vitmin B6 biosynthesis in higher plants. Proc Natl Acad Sci USA 102:13687–13692

    Article  CAS  Google Scholar 

  • Suzuki Y, Uchida K (1969) Biosynthesis of riboflavin-α-glucoside by plant grains. Arch Biochem Biophys 130(1):683–684

    Article  PubMed  CAS  Google Scholar 

  • Suzuki Y, Uchida K (1983) Formation of glucosyl riboflavin in germinating barley seeds. Nogaku Kenkyu 9:285–292

    Google Scholar 

  • Suzuki Y, Uchida K (1994) Enzymatic formation of a new derivative of thiamin, β-galactosylthiamin. Biosci Biotech Biochem 58:1273–1276

    Article  Google Scholar 

  • Suzuki Y, Ki YH, Uchida K, Takami M (1996) Enzymatic synthesis of glucosylated and phosphatidylated biologically active compounds. J Appl Glycosci 43:273–282

    CAS  Google Scholar 

  • Tachibana S (1955) Sugar compounds of riboflavin II Biosynthesis of riboflavinyl galactoside by Aspergillus oryzae. Vitamins 9:119–124

    CAS  Google Scholar 

  • Tachibana S (1971) Isolation of riboflavin glycosides. In: Vitamin and coenzymes. McCormick CDB, Wright LD (eds) Methods in enzymology. Academic Press, New York, 18B: 413–416

    Google Scholar 

  • Tai CY, Huang SC, Huang MS, Liu HS (2001) Hydrolysis of amylopectin by isoamylase under supercritical carbon dioxide. J Chin Inst Chem Eng 32(3):269–275

    CAS  Google Scholar 

  • Tapavicza SV, Bell D, Kopp-Holtwiesche B (2000) Plant growth enhancement against phytopathogenic fungi and/or soil borne pests. Patent WO 0002451 (CA 132)

    Google Scholar 

  • The Merck Index (2006) In: Neil MJO (ed) An encyclopedia of chemicals, drugs and biologicals, 14th edn. Merck and Co., Whitehouse Station

    Google Scholar 

  • Tietze LF, Griesbach U, Schuberth I, Bothe U, Marra A, Dondoni A (2003) Novel carboranyl C-glycosides for the treatment of cancer by boron neutron capture therapy. Chem Eur J 9:1296–1302

    Article  PubMed  CAS  Google Scholar 

  • Uchida K, Suzuki Y (1968) Production of riboflavin glucoside in growing cultures of Ashbya gossypii and Eremothecium ashbyii. Denpon Nogei Kagaku Kaishi 42(4):233–237

    Article  CAS  Google Scholar 

  • Vadivelan G, Divakar S (2011a) Enzymatic synthesis of L-Dopa glycosides. Indian J Chem Sect B 50B:1779–1785

    CAS  Google Scholar 

  • Vadivelan G, Divakar S (2011b) Enzymatic Synthesis of serotonyl and epinephryl glycosides. Int J Fund Appl Life Sci 1(2):15–21

    Google Scholar 

  • Vered Y, Rabey JM, Paleveitch D, Grosskopf I, Harsat A, Yanowski A, Shabtai H, Graff E (1994) Bioavailability of levodopa after consumption of Vicia faba seedlings by Parkinsonian patients and control subjects. Clin Neuropharmacol 17:138–146

    Article  Google Scholar 

  • Vic G, Thomas D (1992) Enzyme-catalyzed synthesis of alkyl-β-D-glucosides in organic media. Tetrahedron Lett 33:4567–4570

    Article  CAS  Google Scholar 

  • Vic G, Thomas D, Crout DHG (1997) Solvent effect on enzyme-catalyzed synthesis of β-D-glucosides using the reverse hydrolysis method application to the preparative-scale synthesis of 2-hydroxybenzyl and octyl β-D-glucopyronosides. Enzyme Microb Technol 20:597–603

    Article  CAS  Google Scholar 

  • Vijayakumar GR, Divakar S (2005) Synthesis of guaiacol-α-D-glucoside and curcumin- bis-α-D-glucoside by an amyloglucosidase from Rhizopus. Biotechnol Lett 27:1411–1415

    Article  CAS  Google Scholar 

  • Vijayakumar GR, Divakar S (2007) Amyloglucosidase catalyzed synthesis of eugenyl and curcuminyl glycosides. Biotechnol Lett 29:575–584

    Article  PubMed  CAS  Google Scholar 

  • Vijayakumar GR, Manohar B, Divakar S (2006) Amyloglucosidase catalyzed synthesis of curcumin-bis-α-D-glucoside-A response surface methodological study. Eur Food Res Technol 223:725–730

    Article  CAS  Google Scholar 

  • Vijayakumar GR, George C, Divakar S (2007) Synthesis of n-alkyl glucosides by amyloglucosidase. Ind J Chem B 46B:314–319

    CAS  Google Scholar 

  • Walker J, Alshafie G, Abou-Issa H, Curley R Jr (2002) An improved synthesis of the C-linked glucuronide of N-(4-hydroxyphenyl) retinamide. Bioorg Med Chem Lett 12:2447–2450

    Article  PubMed  CAS  Google Scholar 

  • Watanabae T, Kawada T, Kato T, Harada T, Iwai K (1994) Effects of capsaicin analogs on adrenalin catecholamine secretion in rats. Life Sci 54:369–374

    Article  Google Scholar 

  • Werner R, Manthey KC, Griffin JB, Zempleni J (2005) HepG2 cells develop signs of riboflavin deficiency within 4 days of culture in riboflavin-deficient medium. J Nutr Biochem 16:617–624

    Article  PubMed  CAS  Google Scholar 

  • Whitby LG (1971)Glycosides or riboflavin. In: Vitamin and coenzymes. McCormick CDB, Wright LD (eds) Methods in enzymology. Academic Press, New York, 18B:404–413

    Google Scholar 

  • Wieder R, Novick SC, Hollis BW, Bryan M, Chanel SM, Owusu K, Camastra D, Saunders T, Pliner L, Harrison J, Bonate P, Williams T, Soignet S (2003) Pharmacokinetics and safety of ILX23-7553, a non-calcemic-vitamin D3 analogue, in a phase I study of patients with advanced malignancies. Invest New Drugs 21:445–452

    Article  PubMed  CAS  Google Scholar 

  • Wyler H, Meuer U, Bauer J, Stravs-Mombelli L (2004) Cyclodopa glucoside ((2S)-5-(β-D-glucopyranosyloxy)-6-hydroxyindoline-2-carboxylicacid) and its occurrence in red beet (beta Vulgaris Varnn rubra L.). Helvetica Chim Acta 67(5)):1348–1355

    Google Scholar 

  • Yamada H, Aimi Y, Nagatsu I, Taki K, Kudo M, Arai R (2007) Immunohistochemical detection of L-dopa derived dopamine within serotonergic fibres in the striatum and the substantia nigra pars reticulata in Parkinsonian model rats. Neurosci Res 59:1–7

    Article  PubMed  CAS  Google Scholar 

  • Yar MD (1993) Parkinson’s disease, the L-dopa era. Adv Neurobiol 60:11–17

    Google Scholar 

  • Zhou JH (2000) Herbal sweetening and preservative composition comprising licorice extract and mogrosides obtained from plants belonging to cucurbitaceae and/or momordica. Patent US 6103240 (CA 133 168393)

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Central Food Technological Research Institute, Mysore, Karnataka, India

    Soundar Divakar

Authors
  1. Soundar Divakar
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Soundar Divakar .

Rights and permissions

Reprints and permissions

Copyright information

© 2013 Springer India

About this chapter

Cite this chapter

Divakar, S. (2013). Glycosylation of Some Selected Phenols and Vitamins. In: Enzymatic Transformation. Springer, India. https://doi.org/10.1007/978-81-322-0873-0_8

Download citation

Publish with us

Policies and ethics

Search

Navigation