Skip to main content
SpringerLink
Log in

Enzymatic Processing of Bioactive Glycosides from Natural Sources

  • Chapter
  • First Online:
Carbohydrates in Sustainable Development II

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 295))

Abstract

A number of biologically active natural products are glycosides. Often, the glycosidic residue is crucial for their activity. In other cases, glycosylation only improves their pharmacokinetic parameters. Enzymatic modification of these glycosides – both extension of the glycoside moiety and its selective trimming – is advantageous due to their selectivity and mildness of the reaction conditions in the presence of reactive and sensitive complex aglycones. Enzymatic reactions enable the resulting products to be used as “natural products”, e.g., in nutraceuticals. This chapter concentrates on naturally occurring glycosides used in medicine but also in the food and flavor industry (e.g., sweeteners). Both “classical” and modern methods will be discussed.

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

Access this chapter

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

Institutional subscriptions

References

  1. Kim NC, Kinghorn AD (2002) Arch Pharmacol Res 25:725–746

    Article  CAS  Google Scholar 

  2. Křen V, Martínková L (2001) Curr Med Chem Rev 8:1313–1338

    Google Scholar 

  3. Křen V, Řezanka T (2008) FEMS Microbiol Rev 32(5):858–889

    Article  Google Scholar 

  4. Grynkiewicz G, Szeja W, Boryski J (2008) Drug Res 65:655–676

    CAS  Google Scholar 

  5. Křen V, Thiem J (1997) Chem Soc Rev 26(6):463–474

    Article  Google Scholar 

  6. Bojarová P, Křen V (2009) Trends Biotechnol 27:199–209

    Article  Google Scholar 

  7. Monti D, Candido A, Silva MC, Křen V, Riva S, Danieli B (2005) Adv Synth Cat 347:1168–1174

    Article  CAS  Google Scholar 

  8. Riva S (2001) Curr Chem Biol 5:106–111

    Article  CAS  Google Scholar 

  9. Fulder S (1980) The root of being. Ginseng and the pharmacology of harmony. Hutchinson and Co., London

    Google Scholar 

  10. Takagi K, Saito H, Nabata H (1972) Jpn J Pharmacol 22:245–459

    Article  CAS  Google Scholar 

  11. Nabata H, Saito H, Takagi K (1973) Jpn J Pharmacol 23:29–41

    Article  CAS  Google Scholar 

  12. Saito H, Suda K, Schwab M, Thoenen H (1977) Jpn J Pharmacol 27:445–451

    Article  CAS  Google Scholar 

  13. Hiai S, Yokoyawa H, Oura H, Yano S (1979) Endocrinol Jpn 26:661–665

    Article  CAS  Google Scholar 

  14. Fuchs H, Bachran D, Panjideh H, Schellmann N, Weng A, Melzig MF, Sutherland M, Bachran C (2009) Curr Drug Targets 10:140–151

    Article  CAS  Google Scholar 

  15. Bachran C, Bachran S, Sutherland M, Bachran D, Fuchs H (2008) Med Chem 8:576–584

    Google Scholar 

  16. Kohda H, Tanaka O (1975) Yakugaku Zasshi 95:246–249

    CAS  Google Scholar 

  17. Ko SR, Suzuki Y, Choi KJ, Kim YH (2000) Biosci Biotechnol Biochem 64:2739–2743

    Article  CAS  Google Scholar 

  18. Ko SR, Choi KJ, Suzuki K, Suzuki Y (2003) Chem Pharm Bull 51(4):404–408

    Article  CAS  Google Scholar 

  19. Ko SR, Choi KJ, Uchida K, Suzuki Y (2003) Planta Med 69:285–286

    Article  CAS  Google Scholar 

  20. Ko SR, Suzuki Y, Suzuki K, Choi KJ, Cho BG (2007) Chem Pharm Bull 55:1522–1527

    Article  CAS  Google Scholar 

  21. Yu H, Zhang C, Lu M, Sun F, Fu Y, Jin F (2007) Chem Pharm Bull 55:231–235

    Article  CAS  Google Scholar 

  22. Danieli B, Falcone L, Monti D, Riva S, Gebhardt S, Schubert-Zsilavecz M (2001) J Org Chem 66:262–269

    Article  CAS  Google Scholar 

  23. Mizutani K (1994) Food phytochemicals for cancer prevention II. In: Ho C, Osawa M, Huangand M, Rosen RT (eds) ACS symposium series, vol 547. American Chemical Society, Washington, DC, pp 322–328

    Google Scholar 

  24. Mizutani K, Kuramoto K, Tamura Y, Ohtake N, Doi S, Nakamura M, Tanaka O (1994) Biosci Biotech Biochem 58:554–555

    Article  CAS  Google Scholar 

  25. Kuramoto T, Ito Y, Oda M (1994) Biosci Biotech Biochem 58:455–458

    Article  CAS  Google Scholar 

  26. Kauffman FC (1994) Conjugation-deconjugation reactions in drug metabolism and toxicity. Springer, Berlin

    Book  Google Scholar 

  27. Mulder GJ (1992) Trends Pharmacol Sci 13:302–304

    Article  CAS  Google Scholar 

  28. Carrupt PA, Testa B, Bechalany A, Tayar N, Descas P, Perrissoud DJ (1991) J Med Chem 34:1272–1275

    Article  CAS  Google Scholar 

  29. Brown TE, Carter NE, Scheinmann F, Turner NJ (1995) Tetrahedron Lett 36:1117–1120

    Article  CAS  Google Scholar 

  30. Bors W, Heller W, Michel C, Saran M (1990) Methods Enzymol 186:343–355

    Article  CAS  Google Scholar 

  31. Manach C, Regerat F, Texier O, Agullo G, Demigne C, Remesy C (1996) Nutr Res 16:517–544

    Article  CAS  Google Scholar 

  32. Webb MR, Ebeler SE (2004) Biochem J 384:527–541

    Article  CAS  Google Scholar 

  33. Monti D, Pišvejcová A, Křen V, Lama M, Riva S (2004) Biotechnol Bioeng 87:763–771

    Article  CAS  Google Scholar 

  34. Suzuki Y, Suzuki K (1991) Agric Biol Chem 55:181–187

    Article  CAS  Google Scholar 

  35. Křen V, Cvak L (eds) (1999) Ergot – genus Claviceps, medicinal and aromatic plants – industrial profiles. Harwood Publ Ltd, Amsterdam, London, pp 1–515

    Google Scholar 

  36. Eich E, Pertz H (1994) Pharmazie 42:867–877

    Google Scholar 

  37. Markstein R, Seiler MP, Jaton A, Briner U (1992) Neurochem Int 20:211S–214S

    Article  CAS  Google Scholar 

  38. Eich E, Eichberg D, Schwarz G, Clas F, Loos M (1985) Arznei-Forsch/Drug Res 35(II):1760

    Google Scholar 

  39. Cincotta AH, Meier AH (1989) Life Sci 45:2247–2254

    Article  CAS  Google Scholar 

  40. Floss HG, Günther H, Mothes U, Becker I (1967) Z Naturforschg 22b:399–402

    Google Scholar 

  41. Křen V (1997) Topics Curr Chem 186:45–65

    Article  Google Scholar 

  42. Křen V, Flieger M, Sajdl P (1990) Appl Microbiol Biotechnol 32:645–650

    Article  Google Scholar 

  43. Havlíček V, Flieger M, Křen V, Ryska M (1994) Biol Mass Spectrom 23:57–60

    Article  Google Scholar 

  44. Křen V, Sedmera P, Havlíček V, Fišerová A (1992) Tetrahedron Lett 33:7233–7236

    Article  Google Scholar 

  45. Křen V, Ščigelová M, Přikrylová V, Havlíček V, Sedmera P (1994) Biocatalysis 10:181–193

    Article  Google Scholar 

  46. Ščigelová M, Křen V, Nilsson KGI (1994) Biotechnol Lett 16:683–688

    Article  Google Scholar 

  47. Křen V, Fišerová A, Augé C, Sedmera P, Havlíček V, Šíma P (1996) Bioorg Med Chem 4:869–876

    Article  Google Scholar 

  48. Křen V, Augé C, Sedmera P, Havlíček V (1994) J Chem Soc Perkin Trans 1:2481–2484

    Google Scholar 

  49. Yamamoto I, Muto N, Nagata E, Nakamura T, Suzuki Y (1990) Biochim Biophys Acta 1035:44–55

    Article  CAS  Google Scholar 

  50. Aga H, Yoneyama M, Sakai S, Yamamoto I (1991) Agric Biol Chem 55:1751–1756

    Article  CAS  Google Scholar 

  51. Yamamoto I, Suga S, Mitoh Y, Tanaka M (1990) J Pharmacobio-Dyn 13:688–695

    Article  CAS  Google Scholar 

  52. Yamamoto I, Muto N, Murakami K, Akyiama J (1992) J Nutr 122:871877

    Google Scholar 

  53. Muto N, Terasawa K, Yamamoto I (1992) Int J Vit Nutr Res 62:318–323

    CAS  Google Scholar 

  54. Kumano Y, Sakamoto T, Egawa M, Iwai I, Tanaka M, Yamamoto I (1998) J Nutr Sci Vitaminol 44:345–359

    Article  CAS  Google Scholar 

  55. Weignerová L, Suzuki Y, Huňková Z, Sedmera P, Havlíček V, Marek R, Křen V (1999) Collect Czech Chem Commun 64:1325–1334

    Article  Google Scholar 

  56. Tramice A, Giordano A, Andreotti G, Mollo E, Trincone A (2006) Mar Biotechnol 8:448–452

    Article  CAS  Google Scholar 

  57. Charles RE, Divakar S (2009) Biosci Biotechnol Biochem 73:233–236

    Article  CAS  Google Scholar 

  58. Charles RE, Ponrasu T, Sankar KU, Divakar S (2009) Appl Biochem Biotechnol 159:199–207

    Article  CAS  Google Scholar 

  59. Suzuki Y, Uchida K (1994) Biosci Biotechnol Biochem 58:1273–1276

    Article  Google Scholar 

  60. Křen V, Huňková Z, Halada P, Suzuki Y (1998) Biosci Biotechnol Biochem 62:2415–2417

    Article  Google Scholar 

  61. Tanaka O (1997) Pure Appl Chem 69:675–683

    Article  CAS  Google Scholar 

  62. Fukunaga Y, Miyata T, Nakayasu N, Mizutani K, Kasai R, Tanaka O (1991) Agric Biol Chem 53:1603–1607

    Article  Google Scholar 

  63. Ohtani K, Aikawa Y, Ishikawa H, Kasai R, Kitahata S, Mizutani K, Doi S, Nakamura M, Tanaka O (1991) Agric Biol Chem 55:449–453

    Article  CAS  Google Scholar 

  64. Kasai R, Kaneda N, Tanaka O, Yamasaki K, Sakamoto I, Morimoto K, Okada S, Kitahata S, Furukawa H (1981) Nippon Kagakukaishi 1981:726–735

    Article  Google Scholar 

  65. Esaki S, Tanaka R, Kamiya S (1984) Agric Biol Chem 48:1831

    Article  CAS  Google Scholar 

  66. Ishikawa H, Kitahata S, Ohtami K, Tanaka O (1991) Chem Pharm Bull 39:2043–2045

    Article  CAS  Google Scholar 

  67. Shibata H, Sawa Y, Oka T, Sonoke S, Kim KK, Yoshioka M (1995) Arch Biochem Biophys 2:390–396

    Article  Google Scholar 

  68. Milagre HMS, Martins LR, Takahashi JA (2009) Braz J Microb 40:367–372

    Article  CAS  Google Scholar 

  69. Nakano H, Okamoto K, Yatake T, Kiso T, Kitahata S (1998) J Ferment Bioeng 85:162–168

    Article  CAS  Google Scholar 

  70. Veitch NC, Grayer RJ (2007) Nat Prod Rep 25:555–561

    Article  Google Scholar 

  71. McGhie TK, Walton MC (2007) Mol Nutr Food Res 51:702–713

    Article  CAS  Google Scholar 

  72. Castañeda-Ovando A, Pacheco-Hernandez MD, Paez-Hernandez ME, Rodriguez JA, Galan-Vidal CA (2009) Food Chem 113:859–871

    Article  Google Scholar 

  73. Winterhalter P, Skouroumounis GK (1997) Glycoconjugated aroma compounds: occurrence, role and biotechnological transformation. In: Scheper T (ed) Advances in biochemical engineering/biotechnology. Springer, Heidelberg, pp 74–105

    Google Scholar 

  74. Sarry JE, Günata Z (2004) Food Chem 87:509–521

    Article  CAS  Google Scholar 

  75. Pogorzelski E, Wilkowska A (2007) Flavour Fragrance J 22:251–254

    Article  CAS  Google Scholar 

  76. Palomo ES, Hidalgo DM, Vinas MAG, Coello MSP (2005) Food Chem 92:627–635

    Article  Google Scholar 

  77. Günata Z, Blondeel C, Vallier MJ, Lepoutre JP, Sapis JC, Watanabe N (1998) J Agric Food Chem 46:2748–2753

    Article  Google Scholar 

  78. Ogawa K, Yasuyuki I, Guo W, Wanatabe N, Usui T, Dong S, Tong Q, Sakata K (1997) J Agric Food Chem 45:877–882

    Article  CAS  Google Scholar 

  79. Villena MA, Iranzo JU, Pérez AB (2007) Food Biotechnol 21:181–194

    Article  Google Scholar 

  80. Belancic A, Gunata Z, Vallier MJ, Agosin E (2003) Agric Food Chem 51:1453–1459

    Article  CAS  Google Scholar 

  81. Cabaroglu T, Selli S, Canbas A, Lepoutre JP, Günata Z (2003) Enzyme Microb Technol 33:581–587

    Article  CAS  Google Scholar 

  82. Shoseyov O, Bravdo BA, Ikan R, Chet I (1990) J Agric Food Chem 27:1973–1976

    Google Scholar 

  83. Gueguen Y, Chemardin P, Pien S, Arnaud A, Galzy P (1997) J Biotechnol 55:151–156

    Article  CAS  Google Scholar 

  84. Caldini C, Bonomi F, Pifferi PG, Lanzarini G, Galante YM (1994) Enzyme Microb Technol 16:286–291

    Article  CAS  Google Scholar 

  85. Williams DH (1996) Nat Prod Rep 13:469–477

    Article  CAS  Google Scholar 

  86. Mayville P, Novick RP, Ji G, Beavis R, Yang H, Goger M, Muir TW (1999) Proc Natl Acad Sci USA 96:1218–1223

    Article  CAS  Google Scholar 

  87. Sieradzki K, Roberts RB, Haber SW, Tomasz A (1999) N Engl J Med 340:517–523

    Article  CAS  Google Scholar 

  88. Perkins HR (1969) Biochem J 111:195–205

    CAS  Google Scholar 

  89. Nagarajan R (1993) J Antibiot 46:1181–1195

    Article  CAS  Google Scholar 

  90. Boger D, Colletti SL, Teramoto S, Ramsey TM, Zhou J (1995) Bioorg Med Chem 3:1281–1295

    Article  CAS  Google Scholar 

  91. Nicas TI, Mullen DL, Flokowitsch JE, Preston DA, Snyder NJ, Zweifel MJ, Wilkie SC, Rodriquez MJ, Thompson RC, Cooper RDG (1996) Antimicrob Agents Chemother 40:2194–2199

    CAS  Google Scholar 

  92. Ge M, Chen Z, Onishi HR, Kohler J, Silver LL, Kerns R, Fukuzawa S, Thompson C, Kahne D (1999) Science 284:507–511

    Article  CAS  Google Scholar 

  93. Fu X, Albermann C, Jiang J, Liao J, Zhang C, Thorson JS (2003) Nat Biotechnol 21:1467–1469

    Article  CAS  Google Scholar 

  94. Mendez C, Salas JA (2001) Trends Biotech 19:449–456

    Article  CAS  Google Scholar 

  95. Langenhan JM, Griffith BR, Thorson JS (2005) J Nat Prod 68:1696–1711

    Article  CAS  Google Scholar 

  96. Chisolm JD, Van Vranken DL (2000) J Org Chem 65:7541–7553

    Article  Google Scholar 

  97. Peri F, Nicotra F (2004) Chem Commun 623–627

    Google Scholar 

  98. Griffith BR, Langenhan JM, Thorson JS (2005) Curr Opin Biotechnol 16:622–630

    Article  CAS  Google Scholar 

  99. Daines AM, Maltman BA, Flitsch SL (2004) Curr Opin Chem Biol 8:106–113

    Article  CAS  Google Scholar 

  100. Zhang C, Griffith BR, Fu Q, Albermann C, Fu X, Lee I-K, Li L, Thorson JS (2006) Science 313:1291–1294

    Article  CAS  Google Scholar 

  101. Yang M, Proctor MR, Bolam DN, Errey JC, Field RA, Gilbert HJ, Davis BG (2005) J Am Chem Soc 127:9336–9337

    Article  CAS  Google Scholar 

  102. Thibodeaux CJ, Liu HW (2007) Pure Appl Chem 79:785–799

    Article  CAS  Google Scholar 

  103. Jahn M, Withers S (2003) Biocat Biotrans 21:159–166

    CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the project OC 09045 of the Ministry of Education of the Czech Republic.

Author information

Authors and Affiliations

  1. Institute of Microbiology, Centre for Biocatalysis and Biotransformation, Academy of Sciences of the Czech Republic, Vídeňská 1083, CZ 142 20, Praha 4, Czech Republic

    Lenka Weignerová & Vladimír Křen

Authors
  1. Lenka Weignerová
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Vladimír Křen
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Vladimír Křen .

Editor information

Editors and Affiliations

  1. Fac. Ciências, Depto. Química e Bioquímica, Universidade de Lisboa, Campo Grande, Lisboa, 1749-016, Portugal

    Amélia P. Rauter

  2. , EPFL ICMB LGSA, Swiss Federal Inst. of Technology, Bat BCH, Lausanne, 1015, Switzerland

    Pierre Vogel

  3. Labo. Chimie Organique (LCO), INSA Lyon, av. Albert Einstein 20, Villeurbanne CX, 69621, France

    Yves Queneau

Rights and permissions

Reprints and permissions

Copyright information

© 2010 Springer

About this chapter

Cite this chapter

Weignerová, L., Křen, V. (2010). Enzymatic Processing of Bioactive Glycosides from Natural Sources. In: Rauter, A., Vogel, P., Queneau, Y. (eds) Carbohydrates in Sustainable Development II. Topics in Current Chemistry, vol 295. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2010_51

Download citation

Publish with us

Policies and ethics

Search

Navigation