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Volumn 20, Issue 2, 2015, Pages 3290-3308

Study of coumarin-resveratrol hybrids as potent antioxidant compounds

Author keywords

ADME properties; Antioxidant assays; Electrochemical study; ESR; Hydroxylated 3 phenylcoumarins; Inhibition of ROS

Indexed keywords

ANTIOXIDANT; COUMARIN DERIVATIVE; RESVERATROL; STILBENE DERIVATIVE;

EID: 84923383631     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules20023290     Document Type: Article
Times cited : (43)

References (49)
  • 1
    • 84873398819 scopus 로고    scopus 로고
    • Antioxidant and pro-oxidant effects of polyphenolic compounds and structure-activity relationship evidence
    • Bouayed, J., Bohn, T., Eds.; InTech: Rijeka, Croatia Chapter 2
    • Guardado-Yordi, E.; Pérez-Molina, E.; Matos, M.J.; Uriarte, E. Antioxidant and pro-oxidant effects of polyphenolic compounds and structure-activity relationship evidence. In Nutrition, Well-Being and Health; Bouayed, J., Bohn, T., Eds.; InTech: Rijeka, Croatia, 2012; Chapter 2, pp. 23-48.
    • (2012) Nutrition, Well-Being and Health , pp. 23-48
    • Guardado-Yordi, E.1    Pérez-Molina, E.2    Matos, M.J.3    Uriarte, E.4
  • 2
    • 16244362735 scopus 로고    scopus 로고
    • Synthesis of novel amino and acetyl amino-4-methylcoumarins and evaluation of their antioxidant activity
    • Tyagi, Y.K.; Kumar, A.; Raj, H.G.; Vohra, P.; Gupta, G.; Kumari, R.; Kumar, P.; Gupta, R.K. Synthesis of novel amino and acetyl amino-4-methylcoumarins and evaluation of their antioxidant activity. Eur. J. Med. Chem. 2005, 40, 413-420.
    • (2005) Eur. J. Med. Chem. , vol.40 , pp. 413-420
    • Tyagi, Y.K.1    Kumar, A.2    Raj, H.G.3    Vohra, P.4    Gupta, G.5    Kumari, R.6    Kumar, P.7    Gupta, R.K.8
  • 3
    • 54049100375 scopus 로고    scopus 로고
    • Synthesis, structure, antimicrobial and antioxidant investigations of dicoumarol and related compounds
    • Hamdi, N.; Puerta, C.; Valerga, P. Synthesis, structure, antimicrobial and antioxidant investigations of dicoumarol and related compounds. Eur. J. Med. Chem. 2008, 43, 2541-2548.
    • (2008) Eur. J. Med. Chem. , vol.43 , pp. 2541-2548
    • Hamdi, N.1    Puerta, C.2    Valerga, P.3
  • 7
    • 33646557284 scopus 로고    scopus 로고
    • Synthetic and natural coumarins as antioxidants
    • Kostova, I. Synthetic and natural coumarins as antioxidants. Mini Rev. Med. Chem. 2006, 6, 365-374.
    • (2006) Mini Rev. Med. Chem. , vol.6 , pp. 365-374
    • Kostova, I.1
  • 8
    • 56149107352 scopus 로고    scopus 로고
    • Comparative antioxidant capacities of phenolic compounds measured by various tests
    • Tabart, J.; Kevers, C.; Pincelmail, J.; Defraigne, J.-O.; Dommes, J. Comparative antioxidant capacities of phenolic compounds measured by various tests. Food Chem. 2009, 113, 1226-1233.
    • (2009) Food Chem. , vol.113 , pp. 1226-1233
    • Tabart, J.1    Kevers, C.2    Pincelmail, J.3    Defraigne, J.-O.4    Dommes, J.5
  • 9
    • 15944389028 scopus 로고    scopus 로고
    • Simple coumarins and analogues in medicinal chemistry: Occurrence, synthesis and biological activity
    • Borges, F.; Roleira, F.; Milhazes, N.; Santana, L.; Uriarte, E. Simple coumarins and analogues in medicinal chemistry: Occurrence, synthesis and biological activity. Curr. Med. Chem. 2005, 12, 887-916.
    • (2005) Curr. Med. Chem. , vol.12 , pp. 887-916
    • Borges, F.1    Roleira, F.2    Milhazes, N.3    Santana, L.4    Uriarte, E.5
  • 11
    • 80054908624 scopus 로고    scopus 로고
    • Synthesis and study of a series of 3-arylcoumarins as potent and selective monoamine oxidase B inhibitors
    • Matos, M.J.; Terán, C.; Pérez-Castillo, Y.; Uriarte, E.; Santana, L.; Viña, D. Synthesis and study of a series of 3-arylcoumarins as potent and selective monoamine oxidase B inhibitors. J. Med. Chem. 2011, 54, 7127-7137.
    • (2011) J. Med. Chem. , vol.54 , pp. 7127-7137
    • Matos, M.J.1    Terán, C.2    Pérez-Castillo, Y.3    Uriarte, E.4    Santana, L.5    Viña, D.6
  • 12
    • 84874893498 scopus 로고    scopus 로고
    • Focusing on new monoamine oxidase inhibitors: Differently substituted coumarins as an interesting scaffold
    • Matos, M.J.; Viña, D.; Vázquez-Rodríguez, S.; Uriarte, E.; Santana, L. Focusing on new monoamine oxidase inhibitors: Differently substituted coumarins as an interesting scaffold. Curr. Top. Med. Chem. 2012, 12, 2210-2239.
    • (2012) Curr. Top. Med. Chem. , vol.12 , pp. 2210-2239
    • Matos, M.J.1    Viña, D.2    Vázquez-Rodríguez, S.3    Uriarte, E.4    Santana, L.5
  • 18
    • 53249156531 scopus 로고    scopus 로고
    • trans-Resveratrol: A magical elixir of eternal youth?
    • Orallo, F. trans-Resveratrol: A magical elixir of eternal youth? Curr. Med. Chem. 2008, 15, 1887-1898.
    • (2008) Curr. Med. Chem. , vol.15 , pp. 1887-1898
    • Orallo, F.1
  • 19
    • 1542544147 scopus 로고
    • Study of partial demethylation of some polymethoxy-3-phenylcoumarins and preparation of some new members
    • Krishnaswamy, N.R.; Seshadri, T.R.; Sharma, B.R. Study of partial demethylation of some polymethoxy-3-phenylcoumarins and preparation of some new members. Indian J. Chem. 1966, 4, 120-126.
    • (1966) Indian J. Chem. , vol.4 , pp. 120-126
    • Krishnaswamy, N.R.1    Seshadri, T.R.2    Sharma, B.R.3
  • 20
    • 33645345793 scopus 로고
    • The reactivity of the methylene group in coumarin-4-acetic acids and their esters. Condensation with salicylaldehyde to 4:3′-dicoumaryls
    • Dey, B.B.; Row, K.K. The reactivity of the methylene group in coumarin-4-acetic acids and their esters. Condensation with salicylaldehyde to 4:3′-dicoumaryls. J. Indian Chem. Soc. 1924, 1, 107-124.
    • (1924) J. Indian Chem. Soc. , vol.1 , pp. 107-124
    • Dey, B.B.1    Row, K.K.2
  • 21
    • 37049167859 scopus 로고
    • 7-Hydroxy-3-phenylcoumarin
    • Baker, W. 7-Hydroxy-3-phenylcoumarin. J. Chem. Soc. 1927, 2898-2899.
    • (1927) J. Chem. Soc. , pp. 2898-2899
    • Baker, W.1
  • 22
    • 84923350679 scopus 로고
    • cis - and trans-2,3-Dimethoxy-α-phenylcinnamic acid
    • Richtzenhain, H.; Alfredsson, B. cis - and trans-2,3-Dimethoxy-α-phenylcinnamic acid. Acta Chem. Scand. 1953, 7, 1173-1175.
    • (1953) Acta Chem. Scand. , vol.7 , pp. 1173-1175
    • Richtzenhain, H.1    Alfredsson, B.2
  • 23
    • 33947460201 scopus 로고
    • Reduction of phenols. New synthesis of oxyhexahydro-3-oxophenanthrenes by cyclodehydration of 4-(β-arylethyl)-1,3-cyclohexanediones
    • Walker, G.N. Reduction of phenols. New synthesis of oxyhexahydro-3-oxophenanthrenes by cyclodehydration of 4-(β-arylethyl)-1,3-cyclohexanediones. J. Am. Chem. Soc. 1958, 80, 645-652.
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 645-652
    • Walker, G.N.1
  • 24
    • 0037260793 scopus 로고    scopus 로고
    • Synthesis and binding affinity of 3-aryl-7-hydroxycoumarins to human alpha and beta estrogen receptors
    • Kirkiacharian, S.; Lormier, A.T.; Resche-Rigon, M.; Bouchoux, F.; Cerede, E. Synthesis and binding affinity of 3-aryl-7-hydroxycoumarins to human alpha and beta estrogen receptors. Ann. Pharm. Francaises 2003, 61, 51-56.
    • (2003) Ann. Pharm. Francaises , vol.61 , pp. 51-56
    • Kirkiacharian, S.1    Lormier, A.T.2    Resche-Rigon, M.3    Bouchoux, F.4    Cerede, E.5
  • 25
    • 33845933196 scopus 로고    scopus 로고
    • Inhibition of horseradish peroxidase catalytic activity by new 3-phenylcoumarin derivatives: Synthesis and structure-activity relationships
    • Kabeya, L.M.; Marchi, A.A.; Kanashiro, A.; Lopes, N.P.; Silva, C.H.T.P.; Pupo, M.T.; Lucisano-Valima, Y.M. Inhibition of horseradish peroxidase catalytic activity by new 3-phenylcoumarin derivatives: Synthesis and structure-activity relationships. Bioorg. Med. Chem. 2007, 15, 1516-1524.
    • (2007) Bioorg. Med. Chem. , vol.15 , pp. 1516-1524
    • Kabeya, L.M.1    Marchi, A.A.2    Kanashiro, A.3    Lopes, N.P.4    Silva, C.H.T.P.5    Pupo, M.T.6    Lucisano-Valima, Y.M.7
  • 26
    • 0035799725 scopus 로고    scopus 로고
    • Unusually large numbers of electrons for the oxidation of polyphenolic antioxidants
    • Hotta, H.; Sakamoto, H.; Nagano, S.; Osakai, T.; Tsujino, Y. Unusually large numbers of electrons for the oxidation of polyphenolic antioxidants. Biochim. Biophys. Acta 2001, 1526, 159-167.
    • (2001) Biochim. Biophys. Acta , vol.1526 , pp. 159-167
    • Hotta, H.1    Sakamoto, H.2    Nagano, S.3    Osakai, T.4    Tsujino, Y.5
  • 27
    • 0034773950 scopus 로고    scopus 로고
    • Development and validation of an improved oxygen radical absorbance capacity assay using fluorescein as the fluorescent probe
    • Ou, B.; Hampsch-Woodill, M.; Prior, R.L. Development and validation of an improved oxygen radical absorbance capacity assay using fluorescein as the fluorescent probe. J. Agric. Food Chem. 2001, 49, 4619-4626.
    • (2001) J. Agric. Food Chem. , vol.49 , pp. 4619-4626
    • Ou, B.1    Hampsch-Woodill, M.2    Prior, R.L.3
  • 28
    • 77954536067 scopus 로고    scopus 로고
    • Assessment of antioxidant capacity in vitro and in vivo
    • Niki, E. Assessment of antioxidant capacity in vitro and in vivo. Free Radic. Biol. Med. 2010, 49, 503-515.
    • (2010) Free Radic. Biol. Med. , vol.49 , pp. 503-515
    • Niki, E.1
  • 29
    • 84892434889 scopus 로고    scopus 로고
    • Protective effect of synthetic hydroxycoumarin derivatives on bovine aortic endothelial cells against oxidative stress induced by 3-morpholinosydnonimine and hydrogen peroxide
    • Perez-Cruz, F.; Montecinos, R.; Villamena, F.A.; Das, A.; Uriarte, E.; Lopez-Alarcón, C.; Olea-Azar, C. Protective effect of synthetic hydroxycoumarin derivatives on bovine aortic endothelial cells against oxidative stress induced by 3-morpholinosydnonimine and hydrogen peroxide. Free Radic. Biol. Med. 2012, 53, S115.
    • (2012) Free Radic. Biol. Med. , vol.53 , pp. S115
    • Perez-Cruz, F.1    Montecinos, R.2    Villamena, F.A.3    Das, A.4    Uriarte, E.5    Lopez-Alarcón, C.6    Olea-Azar, C.7
  • 30
    • 39049173445 scopus 로고    scopus 로고
    • Effect of antioxidant oxidation potential in the oxygen radical absorption capacity (ORAC) assay
    • Bisby, R.H.; Brooke, R.; Navaratnam, S. Effect of antioxidant oxidation potential in the oxygen radical absorption capacity (ORAC) assay. Food Chem. 2008, 108, 1002-1007.
    • (2008) Food Chem. , vol.108 , pp. 1002-1007
    • Bisby, R.H.1    Brooke, R.2    Navaratnam, S.3
  • 32
  • 33
    • 84863780324 scopus 로고    scopus 로고
    • Characteristics of the spin-trapping reaction of a free radical derived from AAPH: Further development of the ORAC-ESR assay
    • Nakajima, A.; Matsuda, E.; Masuda, Y.; Sameshima, H.; Ikenoue, T. Characteristics of the spin-trapping reaction of a free radical derived from AAPH: Further development of the ORAC-ESR assay. Anal. Bioanal. Chem. 2012, 403, 1961-1970.
    • (2012) Anal. Bioanal. Chem. , vol.403 , pp. 1961-1970
    • Nakajima, A.1    Matsuda, E.2    Masuda, Y.3    Sameshima, H.4    Ikenoue, T.5
  • 34
    • 84857851492 scopus 로고    scopus 로고
    • Oxygen radical absorbance capacity (ORAC) of cyclodextrin-solubilized flavonoids, resveratrol and astaxanthin as measured with the ORAC-EPR method
    • Sueishi, Y.; Ishikawa, M.; Yoshioka, D.; Endoh, N.; Oowada, S.; Shimmei, M.; Fujii, H.; Kotake, Y. Oxygen radical absorbance capacity (ORAC) of cyclodextrin-solubilized flavonoids, resveratrol and astaxanthin as measured with the ORAC-EPR method. J. Clin. Biochem. Nutr. 2012, 50, 127-132.
    • (2012) J. Clin. Biochem. Nutr. , vol.50 , pp. 127-132
    • Sueishi, Y.1    Ishikawa, M.2    Yoshioka, D.3    Endoh, N.4    Oowada, S.5    Shimmei, M.6    Fujii, H.7    Kotake, Y.8
  • 35
    • 59749083932 scopus 로고    scopus 로고
    • An oxygen radical absorbance capacity-like assay that directly quantifies the antioxidant's scavenging capacity against AAPH-derived free radicals
    • Kohri, S.; Fujii, H.; Oowada, S.; Endoh, N.; Sueishi, Y.; Kusakabe, M.; Shimmei, M.; Kotake, Y. An oxygen radical absorbance capacity-like assay that directly quantifies the antioxidant's scavenging capacity against AAPH-derived free radicals. Anal. Biochem. 2009, 386, 167-171.
    • (2009) Anal. Biochem. , vol.386 , pp. 167-171
    • Kohri, S.1    Fujii, H.2    Oowada, S.3    Endoh, N.4    Sueishi, Y.5    Kusakabe, M.6    Shimmei, M.7    Kotake, Y.8
  • 37
    • 84858684696 scopus 로고    scopus 로고
    • Antioxidant activity coefficient, mechanism, and kinetics of different derivatives of flavones and flavanones towards superoxide radical
    • Ahmed, S.; Shakeel, F. Antioxidant activity coefficient, mechanism, and kinetics of different derivatives of flavones and flavanones towards superoxide radical. Czech J. Food Sci. 2012, 30, 153-163.
    • (2012) Czech J. Food Sci. , vol.30 , pp. 153-163
    • Ahmed, S.1    Shakeel, F.2
  • 38
    • 42649094135 scopus 로고    scopus 로고
    • Validation of a new method using the reactivity of electrogenerated superoxide radical in the antioxidant capacity determination of flavonoids
    • Le Bourvellec, C.; Hauchard, D.; Darchen, A.; Burgota, J.L.; Abasqa, M.L. Validation of a new method using the reactivity of electrogenerated superoxide radical in the antioxidant capacity determination of flavonoids. Talanta 2008, 75, 1098-1103.
    • (2008) Talanta , vol.75 , pp. 1098-1103
    • Le Bourvellec, C.1    Hauchard, D.2    Darchen, A.3    Burgota, J.L.4    Abasqa, M.L.5
  • 39
    • 0037059356 scopus 로고    scopus 로고
    • Antioxidant activity coefficients for plant aquatic-alcohol extracts
    • Korotkova, E.I.; Karbainov, Y.A.; Shevchuk, A.V. Antioxidant activity coefficients for plant aquatic-alcohol extracts. J. Electroanal. Chem. 2002, 518, 56-60.
    • (2002) J. Electroanal. Chem. , vol.518 , pp. 56-60
    • Korotkova, E.I.1    Karbainov, Y.A.2    Shevchuk, A.V.3
  • 40
    • 0037526182 scopus 로고    scopus 로고
    • Investigation of antioxidant and catalytic properties of some biologically active substances by voltammetry
    • Korotkova, E.I.; Karbainov, Y.A.; Avramchik, O.A. Investigation of antioxidant and catalytic properties of some biologically active substances by voltammetry. Anal. Bioanal. Chem. 2003, 375, 465-468.
    • (2003) Anal. Bioanal. Chem. , vol.375 , pp. 465-468
    • Korotkova, E.I.1    Karbainov, Y.A.2    Avramchik, O.A.3
  • 42
    • 84857192927 scopus 로고    scopus 로고
    • Available online: accessed on 15 December 2014
    • Molinspiration Cheminformatics. Available online: http://www.molinspiration.com/services/properties.html (accessed on 15 December 2014).
    • Molinspiration Cheminformatics
  • 44
    • 34548126843 scopus 로고    scopus 로고
    • Fluorescent and luminescent probes for measurement of oxidative and nitrosative species in cells and tissues: Progress, pitfalls, and prospects
    • Wardman, P. Fluorescent and luminescent probes for measurement of oxidative and nitrosative species in cells and tissues: Progress, pitfalls, and prospects. Free Rad. Bio. Med. 2007, 43, 995-1022.
    • (2007) Free Rad. Bio. Med. , vol.43 , pp. 995-1022
    • Wardman, P.1
  • 45
    • 15244352099 scopus 로고    scopus 로고
    • Review of methods to determine chain-breaking antioxidant activity in food
    • Roginsky, V.; Lissi, E. Review of methods to determine chain-breaking antioxidant activity in food. Food Chem. 2005, 92, 235-254.
    • (2005) Food Chem. , vol.92 , pp. 235-254
    • Roginsky, V.1    Lissi, E.2
  • 46
    • 0037157037 scopus 로고    scopus 로고
    • Analysis of antioxidant activities of common vegetables employing oxygen radical absorbance capacity (ORAC) and ferric reducing antioxidant power (FRAP) assays: A comparative study
    • Ou, B.; Huang, D.; Hampsch-Woodill, M.; Flanagan, J.A.; Deemer, E.K. Analysis of antioxidant activities of common vegetables employing oxygen radical absorbance capacity (ORAC) and ferric reducing antioxidant power (FRAP) assays: A comparative study. J. Agric. Food Chem. 2002, 50, 3122-3128.
    • (2002) J. Agric. Food Chem. , vol.50 , pp. 3122-3128
    • Ou, B.1    Huang, D.2    Hampsch-Woodill, M.3    Flanagan, J.A.4    Deemer, E.K.5
  • 47
    • 0001214604 scopus 로고
    • Use of hydrodynamic chronocoulometry for simultaneous determination of diffusion coefficients and concentrations of dioxygen in various media
    • Tsushima, M.; Tokuda, K.; Ohsaka, T. Use of hydrodynamic chronocoulometry for simultaneous determination of diffusion coefficients and concentrations of dioxygen in various media. Anal. Chem. 1994, 66, 4551-4556.
    • (1994) Anal. Chem. , vol.66 , pp. 4551-4556
    • Tsushima, M.1    Tokuda, K.2    Ohsaka, T.3
  • 48
    • 84863490064 scopus 로고    scopus 로고
    • Voltammetric determination of antioxidant character in Berberis lycium Royel, Zanthoxylum armatum and Morus nigra Linn plants
    • Ahmed, S.; Shakeel, F. Voltammetric determination of antioxidant character in Berberis lycium Royel, Zanthoxylum armatum and Morus nigra Linn plants. Pak. J. Pharm. Sci. 2012, 25, 501-507.
    • (2012) Pak. J. Pharm. Sci. , vol.25 , pp. 501-507
    • Ahmed, S.1    Shakeel, F.2
  • 49
    • 78650531600 scopus 로고    scopus 로고
    • Métodos para determinac¸ão de atividade antioxidante in vitro em substratos orgânicos
    • Alves, C.Q.; David, J.M. Métodos para determinac¸ão de atividade antioxidante in vitro em substratos orgânicos. Quim. Nova 2010, 33, 2202-2210.
    • (2010) Quim. Nova , vol.33 , pp. 2202-2210
    • Alves, C.Q.1    David, J.M.2


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