메뉴 건너뛰기




Volumn 58, Issue 2, 2010, Pages 807-813

Regioselective lipase-catalyzed synthesis of 3-o-acyl derivatives of resveratrol and study of their antioxidant properties

Author keywords

Acylation; Antioxidants; Lipases; Polyphenols; Regloselectivity; TEAC; Trolox equivalent antioxidant activity; Vinyl esters

Indexed keywords

ANTIOXIDANT; BACTERIAL PROTEIN; IMMOBILIZED ENZYME; LIPASE B, CANDIDA ANTARCTICA; RESVERATROL; STILBENE DERIVATIVE; TRIACYLGLYCEROL LIPASE;

EID: 74849140959     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf903210q     Document Type: Article
Times cited : (74)

References (45)
  • 2
    • 0036804710 scopus 로고    scopus 로고
    • Free radicals, antioxidants, and nutrition
    • Fang, Y. Z.; Yang, S.; Wu, G. Y. Free radicals, antioxidants, and nutrition. Nutrition 2002, 18, 872-879.
    • (2002) Nutrition , vol.18 , pp. 872-879
    • Fang, Y.Z.1    Yang, S.2    Wu, G.Y.3
  • 3
    • 12244299440 scopus 로고    scopus 로고
    • The impact of different antioxidant agents alone or in combination on reactive oxygen species, antioxidant enyzmes and cytokines in a series of advanced cancer patients at different sites: Correlation with disease progression
    • DOI 10.1080/10715760303849
    • Mantovani, G.; Maccio, A.; Madeddu, C.; Mura, L.; Gramignano, G.; Lusso, M. R.; Murgia, V.; Camboni, P.; Ferreli, L.; Mocci, M.; Massa, E. The impact of different antioxidant agents alone or in combination on reactive oxygen species, antioxidant enzymes and cytokines in a series of advanced cancer patients at different sites: Correlation with disease progression. Free Radical Res. 2003, 37, 213-223. (Pubitemid 36124348)
    • (2003) Free Radical Research , vol.37 , Issue.2 , pp. 213-223
    • Mantovani, G.1    Maccio, A.2    Madeddu, C.3    Mura, L.4    Gramignano, G.5    Lusso, M.R.6    Murgia, V.7    Camboni, P.8    Ferreli, L.9    Mocci, M.10    Massa, E.11
  • 5
    • 0033873673 scopus 로고    scopus 로고
    • Selfassembly and antioxidant properties of octanoyl-6-O-ascorbic acid
    • Lo Nostro, P.; Capuzzi, G.; Romani, A.; Mulinacci, N. Selfassembly and antioxidant properties of octanoyl-6-O-ascorbic acid. Langgmuir 2000, 16, 1744-1750.
    • (2000) Langgmuir , vol.16 , pp. 1744-1750
    • Lo Nostro, P.1    Capuzzi, G.2    Romani, A.3    Mulinacci, N.4
  • 6
    • 33846510561 scopus 로고    scopus 로고
    • Protection of lipids from oxidation by epicatechin, trans-resveratrol, and gallic and caffeic acids in intestinal model systems
    • DOI 10.1021/jf0621828
    • Kerem, Z.; Chetrit, D.; Shoseyov, O.; Regev-Shoshani, G. Protection of lipids from oxidation by epicatechin, trans-resveratrol, and gallic and caffeic acids in intestinal model systems. J. Agric. Food Chem. 2006, 54, 10288-10293. (Pubitemid 46159040)
    • (2006) Journal of Agricultural and Food Chemistry , vol.54 , Issue.26 , pp. 10288-10293
    • Kerem, Z.1    Chetrit, D.2    Shoseyov, O.3    Regev-Shoshani, G.4
  • 7
    • 70349966418 scopus 로고    scopus 로고
    • Effect of phenolic acids on manganese peroxidase-dependent peroxidation of linoleic acid and degradation of a non-phenolic lignin model compound
    • Kapich, A. N.; Galkin, S.; Hatakka, A. Effect of phenolic acids on manganese peroxidase-dependent peroxidation of linoleic acid and degradation of a non-phenolic lignin model compound. Biocatal. Biotransform. 2007, 25, 350-358.
    • (2007) Biocatal. Biotransform. , vol.25 , pp. 350-358
    • Kapich, A.N.1    Galkin, S.2    Hatakka, A.3
  • 8
    • 74849137796 scopus 로고    scopus 로고
    • Enzymatic modification for ascorbic acid and alpha-tocopherol to enhance their stability in food and nutritional applications
    • Torres, P.; Kunamneni, A.; Ballesteros, A.; Plou, F. J. Enzymatic modification for ascorbic acid and alpha-tocopherol to enhance their stability in food and nutritional applications. Open Food Sci. J. 2008, 2, 1-9.
    • (2008) Open Food Sci. J. , vol.2 , pp. 1-9
    • Torres, P.1    Kunamneni, A.2    Ballesteros, A.3    Plou, F.J.4
  • 9
    • 59449102069 scopus 로고    scopus 로고
    • Lipasecatalyzed synthesis of phenolic lipids from, fish liver oil and dihydrocaffeic acid
    • Sabally, K.; Karboune, S.; St Louis, R.; Kermasha, S. Lipasecatalyzed synthesis of phenolic lipids from, fish liver oil and dihydrocaffeic acid. Biocatal. Biotransform. 2007, 25, 211-218.
    • (2007) Biocatal. Biotransform. , vol.25 , pp. 211-218
    • Sabally, K.1    Karboune, S.2    St Louis, R.3    Kermasha, S.4
  • 10
    • 33745754351 scopus 로고    scopus 로고
    • Comparison of ozone and UV-C treatments on the postharvest stilbenoid monomer, dimer, and trimer induction in var. 'Superior' white table grapes
    • Gonzalez-Barrio, R.; Beltran, D.; Cantos, E.; Gil, M, I.; Espin, J. C.; Tomas-Barberan, F. A. Comparison of ozone and UV-C treatments on the postharvest stilbenoid monomer, dimer, and trimer induction in var. 'Superior' white table grapes. J. Agric. Food Chem. 2006, 54, 4222-4228.
    • (2006) J. Agric. Food Chem. , vol.54 , pp. 4222-4228
    • Gonzalez-Barrio, R.1    Beltran, D.2    Cantos, E.3    Gil, M.I.4    Espin, J.C.5    Tomas-Barberan, F.A.6
  • 11
    • 33745787930 scopus 로고    scopus 로고
    • Antioxidants and inflammatory disease: Synthetic and natural antioxidants with anti-inflammatory activity
    • Geronikaki, A. A.; Gavalas, A. M. Antioxidants and inflammatory disease: Synthetic and natural antioxidants with anti-inflammatory activity, Comb. Chem. High Throughput Screening 2006, 9, 425-442.
    • (2006) Comb. Chem. High Throughput Screening , vol.9 , pp. 425-442
    • Geronikaki, A.A.1    Gavalas, A.M.2
  • 12
    • 20344407841 scopus 로고    scopus 로고
    • Resveratrol as an anti-inflammatory and anti-aging agent: Mechanisms and clinical implications
    • DOI 10.1002/mnfr.200500022
    • de la Lastra, C. A.; Villegas, I. Resveratrol as an anti-inflammatory and anti-aging agent: Mechanisms and clinical implications. Mol. Nutr. Food Res. 2005, 49, 405-430. (Pubitemid 40780389)
    • (2005) Molecular Nutrition and Food Research , vol.49 , Issue.5 , pp. 405-430
    • De La Lastra, C.A.1    Villegas, I.2
  • 14
    • 5744234431 scopus 로고    scopus 로고
    • The grape and wine polyphenol piceatannol is a potent inducer of apoptosis in human SK-Mel-28 melanoma cells
    • Larrosa, M.; Tomas-Barberan, F. A.; Espin, J. C. The grape and wine polyphenol piceatannol is a potent inducer of apoptosis in human SK-Mel-28 melanoma cells. Eur. J. Nutr. 2004, 43, 275-284.
    • (2004) Eur. J. Nutr. , vol.43 , pp. 275-284
    • Larrosa, M.1    Tomas-Barberan, F.A.2    Espin, J.C.3
  • 15
    • 0035405365 scopus 로고    scopus 로고
    • Mechanism of cardioprotection by resveratrol, a phenolic antioxidant present in red wine (review)
    • Wu, J. M.; Wang, Z. R.; Hsieh, T. C.; Bruder, J. L.; Zou, J. G.; Huang, Y. Z. Mechanism of cardioprotection by resveratrol, a phenolic antioxidant present in red wine (review). Int. J. Mol. Med. 2001, 8, 3-17.
    • (2001) Int. J. Mol. Med. , vol.8 , pp. 3-17
    • Wu, J.M.1    Wang, Z.R.2    Hsieh, T.C.3    Bruder, J.L.4    Zou, J.G.5    Huang, Y.Z.6
  • 16
    • 67349183313 scopus 로고    scopus 로고
    • Synthesis of novel trans-stilbene derivatives and evaluation of their potent antioxidant and neuroprotective effects
    • Jung, J. C.; Lim, E.; Lee, Y.; Kang, J. M.; Kim, H.; Jang, S.; Oh, S.; Jung, M. Synthesis of novel trans-stilbene derivatives and evaluation of their potent antioxidant and neuroprotective effects. Eur. J. Med. Chem. 2009, 44, 3166-3174.
    • (2009) Eur. J. Med. Chem. , vol.44 , pp. 3166-3174
    • Jung, J.C.1    Lim, E.2    Lee, Y.3    Kang, J.M.4    Kim, H.5    Jang, S.6    Oh, S.7    Jung, M.8
  • 19
    • 0034645693 scopus 로고    scopus 로고
    • Minireview: Biological effects of resveratrol
    • Fremont, L. Minireview: Biological effects of resveratrol. Life Sci. 2000, 66, 663-673.
    • (2000) Life Sci. , vol.66 , pp. 663-673
    • Fremont, L.1
  • 20
    • 12844261092 scopus 로고    scopus 로고
    • Chemo-enzymatic synthesis and cell-growth inhibition activity of resveratrol analogues
    • DOI 10.1016/j.bioorg.2004.08.003, PII S0045206804000653
    • Cardile, V.; Lombardo, L.; Spatafora, C.; Tringali, C. Chemoenzymatic synthesis and cell-growth inhibition activity of resveratrol analogues, Bioorg. Chem. 2005, 33, 22-33. (Pubitemid 40164184)
    • (2005) Bioorganic Chemistry , vol.33 , Issue.1 , pp. 22-33
    • Cardile, V.1    Lombardo, L.2    Spatafora, C.3    Tringali, C.4
  • 21
    • 84864983865 scopus 로고    scopus 로고
    • Anti-tumor properties of stilbene-based resveratrol analogues: Recent results. Nat
    • Chiliemi, R.; Sciuto, S.; Spatafora, C.; Tringali, C. Anti-tumor properties of stilbene-based resveratrol analogues: Recent results. Nat. Prod. Commun. 2007, 2, 499-513.
    • (2007) Prod. Commun. , vol.2 , pp. 499-513
    • Chiliemi, R.1    Sciuto, S.2    Spatafora, C.3    Tringali, C.4
  • 24
    • 58949095218 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of a library of resveratrol analogues as inhibitors of COX-1, COX-2 and NFkappa B
    • Kang, S. S.; Cuendet, M.; Endringer, D. C.; Croy, V. L.; Pezzuto, J. M.; Lipton, M. A. Synthesis and biological evaluation of a library of resveratrol analogues as inhibitors of COX-1, COX-2 and NFkappa B. Bioorg. Med. Chem. 2009, 17, 1044-1054.
    • (2009) Bioorg. Med. Chem. , vol.17 , pp. 1044-1054
    • Kang, S.S.1    Cuendet, M.2    Endringer, D.C.3    Croy, V.L.4    Pezzuto, J.M.5    Lipton, M.A.6
  • 26
    • 33744933430 scopus 로고    scopus 로고
    • Environmental biocatalysis: From remediation with enzymes to novel green processes
    • DOI 10.1016/j.tibtech.2006.04.002, PII S0167779906000990
    • Alcalde, M.; Ferrer, M.; Plou, F. J.; Ballesteros, A. Environmental biocatalysis: from remediation with enzymes to novel green processes. Trends Biotechnol. 2006, 24, 281-287. (Pubitemid 43841912)
    • (2006) Trends in Biotechnology , vol.24 , Issue.6 , pp. 281-287
    • Alcalde, M.1    Ferrer, M.2    Plou, F.J.3    Ballesteros, A.4
  • 27
    • 0346964455 scopus 로고    scopus 로고
    • Biotransformation of resveratrol: Synthesis of trans-dehydrodimers catalyzed by laccases from Myceliophtora thermophyla and from Trametes pubescens
    • DOI 10.1016/j.tet.2003.10.117
    • Nicotra, S.; Cramarossa, M. R.; Mucci, A.; Pagnoni, U. M.; Riva, S.; Forti, L. Biotransformation of resveratrol: Synthesis of trans-dehydrodimers catalyzed by laceases from Myceliophtora thermophyla and from Trametes pubescens. Tetrahedron 2004, 60, 595-600. (Pubitemid 38045368)
    • (2004) Tetrahedron , vol.60 , Issue.3 , pp. 595-600
    • Nicotra, S.1    Cramarossa, M.R.2    Mucci, A.3    Pagnoni, U.M.4    Riva, S.5    Forti, L.6
  • 28
    • 0345743644 scopus 로고    scopus 로고
    • Enzymatic preparation of phenolic glucosides by Streptococcus mutans
    • Shim, H.; Hong, W.; Ahn, Y. Enzymatic preparation of phenolic glucosides by Streptococcus mutans. Bull. Korean Chem. Soc. 2003, 24, 1680-1682.
    • (2003) Bull. Korean Chem. Soc. , vol.24 , pp. 1680-1682
    • Shim, H.1    Hong, W.2    Ahn, Y.3
  • 29
    • 21844434923 scopus 로고    scopus 로고
    • Regioselective acylation of several polyhydroxylated natural compounds by Candida antarctica lipase B
    • DOI 10.1080/1024220500132508
    • Teng, R. W.; Bui, T. K. A.; McManus, D.; Armstrong, D.; Mau, S. L.; Bacic, A. Regioselective acylation of several polyhydroxylated natural compounds by Candida antarctica lipase B. Biocatal. Biotransform. 2005, 23, 109-116. (Pubitemid 40959704)
    • (2005) Biocatalysis and Biotransformation , vol.23 , Issue.2 , pp. 109-116
    • Teng, R.-W.1    Bui, T.-K.-A.2    McManus, D.3    Armstrong, D.4    Mau, S.-L.5    Bacic, A.6
  • 34
    • 74849116670 scopus 로고    scopus 로고
    • Environmental biocatalysis: From remediation with enzymes to novel green processes
    • Alcalde, M.; Ferrer, M.; Plou, F. J. Environmental biocatalysis: From remediation with enzymes to novel green processes. Biocatal. transform. 2007, 25, 113.
    • (2007) Biocatal. Transform. , vol.25 , pp. 113
    • Alcalde, M.1    Ferrer, M.2    Plou, F.J.3
  • 36
    • 38049007776 scopus 로고    scopus 로고
    • Immobilization of pycnoporus coccineus lacease on eupergit C: Stabilization and treatment of oil mill wastewaters
    • Berrio, J.; Plou, F. J.; Ballesteros, A.; Martin, A. T.; Martinez, M. J. Immobilization of Pycnoporus coccineus lacease on Eupergit C: Stabilization and treatment of oil mill wastewaters. Biocatal. Biotransform. 2007, 25, 130-134.
    • (2007) Biocatal. Biotransform. , vol.25 , pp. 130-134
    • Berrio, J.1    Plou, F.J.2    Ballesteros, A.3    Martin, A.T.4    Martinez, M.J.5
  • 38
    • 0032982508 scopus 로고    scopus 로고
    • Antioxidant activity applying an improved ABTS radical cation decolorization assay
    • DOI 10.1016/S0891-5849(98)00315-3, PII S0891584998003153
    • Re, R.; Pellegrini, N.; Proteggente, A.; Pannala, A.; Yang, M.; Rice-Evans, C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biol Med. 1999, 26, 1231-1237. (Pubitemid 29262709)
    • (1999) Free Radical Biology and Medicine , vol.26 , Issue.9-10 , pp. 1231-1237
    • Re, R.1    Pellegrini, N.2    Proteggente, A.3    Pannala, A.4    Yang, M.5    Rice-Evans, C.6
  • 39
    • 42049119702 scopus 로고    scopus 로고
    • Reaction design for evaluation of the substrate range of hydrolases
    • Antoniotti, S.; Fernandez, X.; Dunach, E. Reaction design for evaluation of the substrate range of hydrolases. Biocatal. Biotransform. 2008, 26, 228-234.
    • (2008) Biocatal. Biotransform. , vol.26 , pp. 228-234
    • Antoniotti, S.1    Fernandez, X.2    Dunach, E.3
  • 40
    • 44649124301 scopus 로고    scopus 로고
    • The effect of ionic liquid media on activity, selectivity and stability of Candida antarctica lipase B in transesterification reactions
    • Los Rios, A. P.; Hernandez-Fernandez, F. J.; Martinez, F. A.; Rubio, M.; Villora, G. The effect of ionic liquid media on activity, selectivity and stability of Candida antarctica lipase B in transesterification reactions. Biocatal. Biotransform. 2007, 25, 151-156.
    • (2007) Biocatal. Biotransform. , vol.25 , pp. 151-156
    • Los Rios, A.P.1    Hernandez-Fernandez, F.J.2    Martinez, F.A.3    Rubio, M.4    Villora, G.5
  • 41
    • 13244295854 scopus 로고    scopus 로고
    • Synthesis of sugar esters in solvent mixtures by lipases from Thermomyces lanuginosus and Candida antarctica B, and their antimicrobial properties
    • DOI 10.1016/j.enzmictec.2004.02.009, PII S0141022904003266
    • Ferrer, M.; Soliveri, J.; Plou, F. J.; Lopez-Cortes, N.; Reyes-Duarte, D.; Christensen, M.; Copa-Patino, J. L.; Ballesteros, A. Synthesis of sugar esters in solvent mixtures by lipases from Thermomyces lanuginosus and Candida antarctica B, and their antimicrobial properties. Enzyme Microb. Technol. 2005, 36, 391-398. (Pubitemid 40186832)
    • (2005) Enzyme and Microbial Technology , vol.36 , Issue.4 , pp. 391-398
    • Ferrer, M.1    Soliveri, J.2    Plou, F.J.3    Lopez-Cortes, N.4    Reyes-Duarte, D.5    Christensen, M.6    Copa-Patino, J.L.7    Ballesteros, A.8
  • 42
    • 20544434206 scopus 로고    scopus 로고
    • Comparison of the phytoestrogen trans-resveratrol (3,4′,5- Trihydroxystilbene) structures from x-ray diffraction and solution NMR
    • DOI 10.1002/mrc.1583
    • Commodari, F.; Khiat, A.; Ibrahimi, S.; Brizius, A. R.; Kalkstein, N. Comparison of the phytoestrogen trans-resveratrol (3,4′, 5trihydroxystilbene) structures from X-ray diffraction and solution NMR. Magn. Reson. Chem. 2005, 43, 567-572. (Pubitemid 40840290)
    • (2005) Magnetic Resonance in Chemistry , vol.43 , Issue.7 , pp. 567-572
    • Commodari, F.1    Khiat, A.2    Ibrahimi, S.3    Brizius, A.R.4    Kalkstein, N.5
  • 43
    • 85040146771 scopus 로고    scopus 로고
    • Sources and chemistry of resveratrol
    • Aggarwal, B. B., Shishodia, S., Eds.; CRC Press: Boca Raton, FL
    • Seeram, N. P.; Kulkarni, V. V.; Padhye, S. Sources and Chemistry of Resveratrol. In Resveratrol in Health and Disease; Aggarwal, B. B., Shishodia, S., Eds.; CRC Press: Boca Raton, FL, 2007; pp 17-32.
    • (2007) Resveratrol in Health and Disease , pp. 17-32
    • Seeram, N.P.1    Kulkarni, V.V.2    Padhye, S.3
  • 44
    • 34250693715 scopus 로고    scopus 로고
    • Stereoselective and enantioselective syntheses of the four stereoisomers of muscol from (3RS)muscone
    • Yuasa, Y.; Fukaya, H.; Yuasa, Y. Stereoselective and enantioselective syntheses of the four stereoisomers of muscol from (3RS)muscone. Helv. Chim. Acta 2007, 90, 977-982.
    • (2007) Helv. Chim. Acta , vol.90 , pp. 977-982
    • Yuasa, Y.1    Fukaya, H.2    Yuasa, Y.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.