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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen


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Volume 82, Issue 1

Issues

Enzymatic transformation of flavonoids and terpenoids: Structural and functional diversity of the novel derivatives

Epameinondas Xanthakis
  • Corresponding author
  • School of Chemical Engineering, Laboratory of Biotechnology, National Technical University of Athens, Athens, Greece
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/ Eleni Theodosiou
  • Corresponding author
  • School of Chemical Engineering, Laboratory of Biotechnology, National Technical University of Athens, Athens, Greece
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/ Sophia Magkouta
  • Corresponding author
  • “G.P. Livanos and M. Simou Laboratories”, Evangelismos Hospital, Department of Critical Care and Pulmonary Services, Medical School, University of Athens, Athens, Greece
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/ Haralambos Stamatis
  • Corresponding author
  • Department of Biological Applications and Technology, Laboratory of Biotechnology, University of Ioannina, Ioannina, Greece
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/ Heleni Loutrari
  • Corresponding author
  • “G.P. Livanos and M. Simou Laboratories”, Evangelismos Hospital, Department of Critical Care and Pulmonary Services, Medical School, University of Athens, Athens, Greece
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/ Charis Roussos
  • Corresponding author
  • “G.P. Livanos and M. Simou Laboratories”, Evangelismos Hospital, Department of Critical Care and Pulmonary Services, Medical School, University of Athens, Athens, Greece
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/ Fragiskos Kolisis
  • Corresponding author
  • School of Chemical Engineering, Laboratory of Biotechnology, National Technical University of Athens, Athens, Greece
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Published Online: 2010-01-03 | DOI: https://doi.org/10.1351/PAC-CON-09-01-19

Flavonoids and terpenoids are promising candidates for use as functional foods and novel therapeutics due to their prominent biological activities. However, the use of several bioactive plant compounds is limited by low stability and solubility problems. This review underlines the feasibility of enzymatic synthesis of novel bioactive analogs of selected flavonoids (silybin, rutin) and terpenoids (perillyl alcohol, POH) in nonconventional reaction systems. The effect of various parameters on the enzymatic acylation and/or glucosylation of these phytochemicals was studied. Also, the role of the structure of the novel molecules in relation to their biological function was investigated in various cancer cell lines.

Keywords: anti-tumor activity; biocatalysis; flavonoids; phytochemicals; terpenoids

Conference

International Biotechnology Symposium (IBS 2008): "Biotechnology for the Sustainability of Human Society", 13th, Dalian, China, 2008-10-12–2008-10-17

References

  • 1

    , Y. J. Surh. Nat. Rev. Cancer3, 768 (2003).CrossrefGoogle Scholar

  • 2

    , P. M. Kris-Etherton, K. D. Hecker, A. Bonanome, S. M. Coval, A. E. Binkoski, K. F. Hilpert, A. E. Griel, T. D. Etherton. Am. J. Med.113, 71 (2002).CrossrefGoogle Scholar

  • 3

    , R. Gažák, D. Walterová, V. Křen. Curr. Med. Chem.14, 315 (2007).CrossrefGoogle Scholar

  • 4

    H. Mo, C. E. Elson. Exp. Biol. Med.229, 567 (2004).Google Scholar

  • 5

    , L. Le Marchand. Biomed. Pharmacother.56, 296 (2002).CrossrefGoogle Scholar

  • 6

    , C. S. Yang, J. M. Landau, M. T. Huang, H. L. Newmark. Annu. Rev. Nutr.21, 381 (2001).CrossrefGoogle Scholar

  • 7

    , H. Loutrari, M. Hatziapostolou, V. Skouridou, E. Papadimitriou, C. Roussos, F. N. Kolisis, A. Papapetropoulos. J. Pharmacol. Exp. Ther.311, 568 (2004).CrossrefGoogle Scholar

  • 8

    P. C. H. Hollman, M. B. Katan. Food Chem. Toxicol.37, 937 (1999).Google Scholar

  • 9

    , A. Scalbert, C. Morand, C. Manach, C. Rémésy. Biomed. Pharmacother.56, 276 (2002).CrossrefGoogle Scholar

  • 10

    , L. Chebil, C. Humeau, A. Falcimaigne, J. M. Engasser, M. Ghoulet. Process Biochem.41, 2237 (2006).CrossrefGoogle Scholar

  • 11

    , V. Křen, J. Kubisch, P. Sedmera, P. Halada, V. Přikrylová, A. Jegorov, L. Cvak, R. Gebhardt, J. Ulrichová, V. Šimánek. J. Chem. Soc., Perkin Trans. 1 2467 (1997).CrossrefGoogle Scholar

  • 12

    V. Křen, J. Ulrichová, P. Kosina, D. Stevenson, P. Sedmera, V. Přikrylová, P. Halada, V. Šimánek. Drug Metab. Dispos.28, 1513 (2000).Google Scholar

  • 13

    , K. Ishihara, N. Nakajima. J. Mol. Catal. B: Enzym.23, 411 (2003).CrossrefGoogle Scholar

  • 14

    , M. H. Katsoura, A. C. Polydera, P. Katapodis, F. N. Kolisis, H. Stamatis. Process Biochem.42, 1326 (2007).CrossrefGoogle Scholar

  • 15

    , E. Theodosiou, M. H. Katsoura, H. Loutrari, K. Purchartova, V. Kren, F. N. Kolisis, H. Stamatis. Biocatal. Biotransform.27, 161 (2009).CrossrefGoogle Scholar

  • 16

    , F. Mellou, H. Loutrari, H. Stamatis, C. Roussos, F. N. Kolisis. Process Biochem.41, 2029 (2006).CrossrefGoogle Scholar

  • 17

    , V. Skouridou, H. Stamatis, F. N. Kolisis. Eur. J. Lipid Sci. Technol.105, 115 (2003).CrossrefGoogle Scholar

  • 18

    , E. Xanthakis, S. Magkouta, H. Loutrari, H. Stamatis, C. Roussos, F. N. Kolisis. Biocatal. Biotransform.27, 170 (2009).CrossrefGoogle Scholar

  • 19

    , T. Mosmann. J. Immunol. Methods65, 55 (1983).CrossrefGoogle Scholar

  • 20

    , C. A. Rice-Evans, N. J. Miller, G. Paganga. Free Radical Biol. Med.20, 933 (1996).CrossrefGoogle Scholar

  • 21

    , B. H. Havsteen. Pharmacol. Therapeutics96, 67 (2002).CrossrefGoogle Scholar

  • 22

    , X. Han, T. Shen, H. Lou. Int. J. Mol. Sci.8, 950 (2007).CrossrefGoogle Scholar

  • 23

    , S. K. Karmee. Appl. Microbiol. Biotechnol.81, 1013 (2009).CrossrefGoogle Scholar

  • 24

    , M. C. Figueroa-Espinoza, P. J. Villeneuve. Agric. Food Chem.53, 2779 (2005).CrossrefGoogle Scholar

  • 25

    , B. Danieli, L. Falcone, D. Monti, S. Riva, S. Gebhardt, M. Schubert-Zsilavecz. J. Org. Chem.66, 262 (2001).CrossrefGoogle Scholar

  • 26

    , S. Riva. Curr. Opin. Chem. Biol.5, 106 (2001).CrossrefGoogle Scholar

  • S. Riva, G. Roda. “Sugar transformations using enzymes in non-aqueous media”, in Methods in Non-aqueous Enzymology, M. N. Gupta (Ed.), p. 146, Birkhäuser, Basel (2000).Google Scholar

  • 28

    , S. Hari Krishna, N. G. Karanth. Catal. Rev.44, 499 (2002).CrossrefGoogle Scholar

  • 29

    , J. S. Dordick. Biotechnol. Prog.8, 259 (1992).CrossrefGoogle Scholar

  • 30

    , M. H. Vermue, J. Tramper. Pure Appl. Chem.67, 345 (1995).CrossrefGoogle Scholar

  • 31

    , M. J. Kim, M. Y. Choi, J. K. Lee, Y. Ahn. J. Mol. Catal. B: Enzym.26, 115 (2003).CrossrefGoogle Scholar

  • 32

    , S. Park, F. Viklund, K. Hult, R. J. Kazlauskas. Green Chem.5, 715 (2003).CrossrefGoogle Scholar

  • 33

    , P. Lozano, T. De Diego, D. Carrié, M. Vaultier, J. L. Iborr. J. Mol. Catal. A: Chem.214, 113 (2004).CrossrefGoogle Scholar

  • 34

    , M. H. Katsoura, A. C. Polydera, L. Tsironis, A. D. Tselepis, H. Stamatis. J. Biotechnol.123, 491 (2006).CrossrefGoogle Scholar

  • 35

    , M. H. Katsoura, A. C. Polydera, L. D. Tsironis, M. P. Petraki, S. Kostić Rajačić, A. D. Tselepis, H. Stamatis. New Biotechnol.26, 83 (2009).CrossrefGoogle Scholar

  • 36

    , B. Danieli, P. De Bellis, G. Carrea, S. Riva. Helv. Chim. Acta73, 1837 (1990).CrossrefGoogle Scholar

  • 37

    , B. Danieli, M. Luisetti, G. Sampognaro, G. Carrea, S. Riva. J. Mol. Catal. B: Enzym.3, 193 (1997).CrossrefGoogle Scholar

  • 38

    , N. Nakajima, K. Ishihara, T. Itoh, T. Furuya, H. Hamada. J. Biosci. Bioeng.87, 105 (1999).CrossrefGoogle Scholar

  • 39

    N. Nakajima, K. Ishihara, H. Hamada, S. I. Kawabe, T. Furuya. J. Biosci. Bioeng.90, 347 (2000).CrossrefGoogle Scholar

  • 40

    , B. Danieli, A. Bertario, G. Carrea, B. Redigolo, F. Secundo, S. Riva. Helv. Chim. Acta76, 2981 (1993).CrossrefGoogle Scholar

  • 41

    , S. Riva, B. Danieli, M. Luisetti. J. Nat. Prod.59, 618 (1996).CrossrefGoogle Scholar

  • 42

    , A. Patti, M. Piattelli, G. Nicolosi. J. Mol. Catal. B: Enzym.10, 577 (2000).CrossrefGoogle Scholar

  • 43

    , C. Gao, P. Mayon, D. A. MacManus, E. N. Vulfson. Biotechnol. Bioeng.71, 235 (2000).CrossrefGoogle Scholar

  • 44

    , A. Kontogianni, V. Skouridou, V. Sereti, H. Stamatis, F. N. Kolisis. Eur. J. Lipid Sci. Technol.103, 655 (2001).CrossrefGoogle Scholar

  • 45

    , A. Kontogianni, V. Skouridou, V. Sereti, H. Stamatis, F. N. Kolisis. J. Mol. Catal. B: Enzym.21, 59 (2003).CrossrefGoogle Scholar

  • 46

    , D. Lambusta, G. Nicolosi, A. Patti, C. Sanfilippo. J. Mol. Catal. B: Enzym.22, 271 (2003).CrossrefGoogle Scholar

  • 47

    , S. Gayot, X. Santarelli, D. Coulon. J. Biotechnol.101, 29 (2003).CrossrefGoogle Scholar

  • 48

    , M. Ardhaoui, A. Falcimaigne, J. M. Engasser, P. Moussou, G. Pauly, M. Ghoul. J. Mol. Catal. B: Enzym.29, 63 (2004).CrossrefGoogle Scholar

  • 49

    , M. Ardhaoui, A. Falcimaigne, S. Ognier, J. M. Engasser, P. Moussou, G. Pauly, M. Ghoul. J. Biotechnol.110, 265 (2004).CrossrefGoogle Scholar

  • 50

    , M. Ardhaoui, A. Falcimaigne, J. M. Engasser, P. Moussou, G. Pauly, M. Ghoul. Biocatal. Biotransform.22, 253 (2004).CrossrefGoogle Scholar

  • 51

    , E. Enaud, C. Humeau, B. Piffaut, M. Girardin. J. Mol. Catal. B: Enzym.27, 1 (2004).CrossrefGoogle Scholar

  • 52

    , E. Passicos, X. Santarelli, D. Coulon. Biotechnol. Lett.26, 1073 (2004).CrossrefGoogle Scholar

  • 53

    , F. Mellou, D. Lazari, H. Skaltsa, A. D. Tselepis, F. N. Kolisis, H. Stamatis. J. Biotechnol.116, 295 (2005).CrossrefGoogle Scholar

  • 54

    , R. W. Teng, T. K. A. Bui, D. McManus, D. Armstrong, S. L. Mau, A. Bacic. Biocatal. Biotransform.23, 109 (2005).CrossrefGoogle Scholar

  • 55

    , D. E. Stevenson, R. Wibisono, D. J. Jensen, R. A. Stanley, J. M. Cooney. Enzyme Microb. Technol.39, 1236 (2006).CrossrefGoogle Scholar

  • 56

    , L. Chebil, J. Anthoni, C. Humeau, C. Gerardin, J. M. Engasser, M. Ghoul. J. Agric. Food Chem.55, 9496 (2007).CrossrefGoogle Scholar

  • 57

    , E. B. De Oliveira, C. Humeau, L. Chebil, E. R. Maia, F. Dehez, B. Maigret, M. Ghoul, J. M. Engasser. J. Mol. Catal. B: Enzym.59, 96 (2009).CrossrefGoogle Scholar

  • 58

    U. T. Bornscheuer, R. J. Kazlauskas. Hydrolases in Organic Synthesis, p. 72, Wiley-VCH, Weinheim (1999).Google Scholar

  • 59

    K. Faber. Biotransformations in Organic Chemistry, 4th ed., p. 94, Springer, Berlin (2000).Google Scholar

  • 60

    , M. Lundh, O. Nordin, E. Hedenström, H. E. Högberg. Tetrahedron: Asymmetry6, 2237 (1995).CrossrefGoogle Scholar

  • 61

    , F. Mellou, D. Lazari, H. Skaltsa, A. D. Tselepis, F. N. Kolisis, H. Stamatis. J. Biotechnol.116, 295 (2005).CrossrefGoogle Scholar

  • 62

    , A. Kontogianni, V. Skouridou, V. Sereti, H. Stamatis, F. N. Kolisis. Eur. J. Lipid Sci. Technol.103, 655 (2001).CrossrefGoogle Scholar

  • 63

    J. Folkman. Semin. Oncol.29, 15 (2002).Google Scholar

  • 64

    , K. Matsubara, K. Ishihara, Y. Mizushina, M. Mori, N. Nakajima. Lett. Drug Des. Discov.1, 329 (2004).CrossrefGoogle Scholar

  • 65

    , H. Nakagawa, Y. Kiyozuka, Y. Uemura, H. Senzaki, N. Shikata, K. Hioki, A. Tsubura. J. Cancer Res. Clin. Oncol.127, 258 (2001).CrossrefGoogle Scholar

  • 66

    , J. Cai, W. G. Jiang, R. E. Mansel. Prostaglandins, Leukotrienes Essent. Fatty Acids60, 21 (1999).CrossrefGoogle Scholar

  • 67

    , H. Loutrari, S. Magkouta, A. Pyriochou, V. Koika, F. N. Kolisis, A. Papapetropoulos, C. Roussos. Nutr. Cancer55, 86 (2006).CrossrefGoogle Scholar

About the article

Published Online: 2010-01-03

Published in Print: 2010-01-03


Citation Information: Pure and Applied Chemistry, Volume 82, Issue 1, Pages 1–16, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/PAC-CON-09-01-19.

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