Abstract
Background: Natural anthocyanins present a low solubility in lipophilic media, which compromises their effective application in lipophilic systems. In this work, cyanidin-3-O-glucoside (Cy3glc) was esterified by the addition of fatty acids with increasing chain-lengths and a structure-activity relationship was performed towards the description of the best analog for skin-care applications. Methods: By enzymatic hemi-synthesis, it was possible to obtain 5 structurally related derivatives of cyanidin-3-O-glucoside with successive C2 increments in the aliphatic chain. The stability in hanks buffer and DMEM with or without FBS was followed by HPLC. The cytotoxicity against keratinocytes was evaluated by MTT assay. The antioxidant capacity was determined by using the fluorescent probe DCF-DA. The effect on enzyme activity was evaluated towards tyrosinase, collagenase, and elastase enzymes by colorimetric assays. MIC and MBC values were obtained against reference strains and against multidrug-resistant isolates. Results: In physiological conditions, cy3glc−fatty acid derivatives are more stable and may be converted to the native anthocyanin. The 5 conjugates showed lower antioxidant capacity and enzymatic inhibitory activities in comparison to the anthocyanin precursor. However, concerning the antibacterial activity, the insertion of a fatty acid chain sprouted the antibacterial activity, showing a clear biphasic effect and a more effective effect on Gram-positive bacteria. Conclusions: Cy3glc-C10 was the most effective compound considering the antimicrobial activity, although a general reduction was observed among the other activities evaluated. This work prompt further assays with a different panoply of derivatives ranging other features including saturation vs. unsaturation, even vs. odd carbon content and linear vs. branched.
Highlights
The cosmetics industry is continuously eager for new natural-based options, as a more informed and aware audience grows by the day
In order to understand the stability of the lipophilic derivatives under physiological conditions, Cy3glc-C4 was incubated in Hank’s Balanced Salt Solution (HBSS) or Dulbecco’s Modified Eagle Medium (DMEM) in the presence or absence of
Had no significant differences, upon the addition of Fetal Bovine Serum (FBS) there is a significant degradation 5 h after incubation (Figure 1). Such evidence strongly suggest that the presence of enzymatic machinery in FBS may be responsible for a readily transformation of the lipophilic derivatives into degradation products that may include the original anthocyanin (Figure 2c,d)
Summary
The cosmetics industry is continuously eager for new natural-based options, as a more informed and aware audience grows by the day. Despite the highly complex network of effective communication systems that skin comprises to prevent prejudicial imbalances, this organ is subjected to such a tremendous number of different external aggressions (UV radiation, pollution, microorganisms, chemicals, and toxins) that nowadays, if one does not take serious measures, early skin aging (and the abnormal alterations rising from this) is almost inevitable [1] This phenomenon leads to alterations in the different skin layers at both physiological and structural levels, which can lead to severe skin diseases [2,3]. The ability to prevent oxidative damages has led to the incorporation of natural bioactives in lotions and facial creams to prevent skin diseases and premature ageing [4] Amongst these phytoactives, the well reported health-promoting properties of anthocyanins make them an appealing alternative for several technological applications, including the cosmetic industry.
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