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QSAR studies of the antioxidant activity of anthocyanins

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Abstract

Through experimental information available from antioxidant assays of seventeen anthocyanins, and six common anthocyanidins, quantitative structure–activity relationships (QSAR) have been established in the present work. The antioxidant bioactivity has been predicted in three different lipid environments: emulsified and bulk oil (methyl linoleate) (in vitro tests) at concentrations of 50 and 250 μM, and 50 μM of the inhibitor, respectively, and in human LDL (low-density lipoprotein; “bad cholesterol”) (ex vivo test) at concentrations of 2.5, 10, and 25 μM of the inhibitor. Radical scavenging activity was predicted in the assay with the 1,1-diphenyl-2-picrylhydrazyl radical (DPPH·). The QSAR models developed for each test and concentration used allowed to obtain prospective information on the constitutional and topological molecular characteristics for anthocyanin/anthocyanidin compounds. Therefore, the antioxidant activity was predicted for twenty-one compounds with unknown experimental values, leading for some of them to a favorable predicted bioactivity.

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Acknowledgements

We thank the National Scientific and Technical Research Council of Argentina [Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET), Argentina] (PIP0311) and Universidad de Buenos Aires (Argentina) for financial support; and Secretaría de Ciencia, Tecnología e Innovación Productiva (formerly Ministerio de Ciencia, Tecnología e Innovación Productiva) for electronic library facilities. N.A.S. thanks the Scientific Research Comission [Comisión de InvestigacionesCientíficas (CIC), La Plata city, Argentina] for a fellowship. A.B.P. and P.R.D. are Research Members of CONICET.

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  1. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas (INIFTA), CONICET, Universidad Nacional de La Plata (UNLP), Diag. 113 y 64, C.C. 16, Sucursal 4, 1900, La Plata, Argentina

    Pablo R. Duchowicz & Nicolás A. Szewczuk

  2. Laboratorio de Química y Bioquímica Estructural, Departamento de Bioquímica Clínica, Hospital de Clínicas “José de San Martín”, Universidad de Buenos Aires, Av. Córdoba 2351, C1120AAF, Buenos Aires, Argentina

    Alicia B. Pomilio

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  1. Pablo R. Duchowicz
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Correspondence to Pablo R. Duchowicz.

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Duchowicz, P.R., Szewczuk, N.A. & Pomilio, A.B. QSAR studies of the antioxidant activity of anthocyanins. J Food Sci Technol 56, 5518–5530 (2019). https://doi.org/10.1007/s13197-019-04024-w

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