Malvidin 3-Glucoside-Fatty Acid Conjugates: From Hydrophilic toward Novel Lipophilic Derivatives.
Luís M CruzMarta GuimarãesPaula AraújoAna ÉvoraVictor de FreitasNuno MateusPublished in: Journal of agricultural and food chemistry (2017)
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.
Keyphrases
- fatty acid
- liquid chromatography
- mass spectrometry
- tandem mass spectrometry
- oxidative stress
- high performance liquid chromatography
- anti inflammatory
- solid phase extraction
- physical activity
- high resolution
- high throughput
- hydrogen peroxide
- gas chromatography
- photodynamic therapy
- simultaneous determination
- capillary electrophoresis
- cancer therapy
- risk assessment
- high speed
- metabolic syndrome
- nitric oxide