title: Synthesis, characterisation and antioxidant features of procyanidin B4 and malvidin-3-glucoside stearic acid derivatives.
abstract: The acylation of procyanidin B4 with a saturated fatty acid chloride containing 18 carbon atoms was studied in order to obtain procyanidin B4 3-O-di-stearic acid conjugate. This compound was structurally characterised by mass spectrometry and 1D and 2D NMR techniques. Derivatization of malvidin-3-glucoside using stearoyl chloride in acetonitrile was also performed yielding mono-, di- and tri-stearic ester derivatives. The novel derivatives obtained revealed significant antioxidant activity, although lower than the respective precursors. However, the chemical modification of anthocyanins and procyanidins (water soluble pigments) to more lipophilic compounds has the advantage of increased bioavailability in biological matrices, and to potentiate their application in food matrices and cosmetic products.
authors.affiliation: Centro de Investigação em Química, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre, 687, 4169-007 Porto, Portugal. Electronic address: luis.cruz@fc.up.pt.
authors.forename: Luis
authors.initials: L
authors.lastname: Cruz
authors.affiliation: Centro de Investigação em Química, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre, 687, 4169-007 Porto, Portugal.
authors.forename: Virgínia C
authors.initials: VC
authors.lastname: Fernandes
authors.affiliation: Centro de Investigação em Química, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre, 687, 4169-007 Porto, Portugal.
authors.forename: Paula
authors.initials: P
authors.lastname: Araújo
authors.affiliation: Centro de Investigação em Química, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre, 687, 4169-007 Porto, Portugal.
authors.forename: Nuno
authors.initials: N
authors.lastname: Mateus
authors.affiliation: Centro de Investigação em Química, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre, 687, 4169-007 Porto, Portugal.
authors.forename: Victor
authors.initials: V
authors.lastname: de Freitas
mesh_terms: D000872:Anthocyanins / Q000138:chemical synthesis / Q000737:chemistry*; D000975:Antioxidants / Q000737:chemistry*; D044946:Biflavonoids / Q000138:chemical synthesis / Q000737:chemistry*; D002392:Catechin / Q000138:chemical synthesis / Q000737:chemistry*; D005960:Glucosides / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D013058:Mass Spectrometry / Q000379:methods; D044945:Proanthocyanidins / Q000138:chemical synthesis / Q000737:chemistry*; D013229:Stearic Acids / Q000737:chemistry*
chemical_list: D000872:Anthocyanins; D000975:Antioxidants; D044946:Biflavonoids; D005960:Glucosides; D044945:Proanthocyanidins; D013229:Stearic Acids; C479578:procyanidin B; C458419:malvidin-3-glucoside; D002392:Catechin
keywords: Lipophilization; Malvidin-3-glucoside; Mass spectrometry; NMR; Procyanidin B4; Stearic acid