Malvidin 3-Glucoside-Fatty Acid Conjugates: From Hydrophilic toward Novel Lipophilic Derivatives.
This work describes the lipophilization reactions of malvidin 3-glucoside with different saturated fatty acid chain lengths using an enzymatic synthesis and the study of their physical-chemical and antioxidant properties. The lipophilic anthocyanins were obtained with satisfactory yields (22-40%) after column chromatography purifications, and they revealed the same appealing chromatic features of the parent anthocyanin. All of the compounds were characterized by mass spectrometry, confirming the regioselective acylation on the glucose moiety. The octanol-water partition coefficients and the hydrophobicity index of the different derivatives were determined, confirming a lipophilicity increase concomitant with the fatty acid chain length. The antioxidant profile was also evaluated by using two in vitro methods (β-carotene-lineolate method and oxygen consumption assay). Overall, a maximum of antioxidant activity was achieved when malvidin 3-glucoside was conjugated with caprylic acid (C8). Altogether, the results obtained provide a good perspective for the technological application of these functionalized anthocyanins in the cosmetics and food industries.
REQUIMTE/LAQV, Departamento de Quı́mica e Bioquı́mica, Faculdade de Ciências, Universidade do Porto , Rua do Campo Alegre 687, 4169-007 Porto, Portugal.
Luís
http://orcid.org/0000-0003-2226-0404
L
Cruz
REQUIMTE/LAQV, Departamento de Quı́mica e Bioquı́mica, Faculdade de Ciências, Universidade do Porto , Rua do Campo Alegre 687, 4169-007 Porto, Portugal.
Marta
M
Guimarães
REQUIMTE/LAQV, Departamento de Quı́mica e Bioquı́mica, Faculdade de Ciências, Universidade do Porto , Rua do Campo Alegre 687, 4169-007 Porto, Portugal.
Paula
P
Araújo
REQUIMTE/LAQV, Departamento de Quı́mica e Bioquı́mica, Faculdade de Ciências, Universidade do Porto , Rua do Campo Alegre 687, 4169-007 Porto, Portugal.
Ana
A
Évora
REQUIMTE/LAQV, Departamento de Quı́mica e Bioquı́mica, Faculdade de Ciências, Universidade do Porto , Rua do Campo Alegre 687, 4169-007 Porto, Portugal.
Victor
V
de Freitas
REQUIMTE/LAQV, Departamento de Quı́mica e Bioquı́mica, Faculdade de Ciências, Universidade do Porto , Rua do Campo Alegre 687, 4169-007 Porto, Portugal.
Nuno
N
Mateus
D000872:Anthocyanins / Q000737:chemistry*; D000975:Antioxidants / Q000737:chemistry; D005227:Fatty Acids / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D013058:Mass Spectrometry; D010084:Oxidation-Reduction
D000872:Anthocyanins; D000975:Antioxidants; D005227:Fatty Acids; D005960:Glucosides; C458419:malvidin-3-glucoside
antioxidant features; enzymatic catalysts; fatty acids; lipophilicity; malvidin 3-glucoside