Protection of Antioxidants, Vitamins E and C, from Ultraviolet Degradation using Feruloylated Vegetable Oil

Abstract

Natural antioxidants are often used in topical personal care formulations to protect the skin from oxidative stresses but are susceptible to degradation due to ultraviolet (UV) radiation. Feruloyl soy glycerols (FSG) are UV absorbers synthesized from the biocatalytic conversion of soybean oil and ferulic acid ethyl ester that have a total UV absorbance and photostability comparable to the commercial UV absorber, 2-ethylhexyl-4-methoxycinnamate (octinoxate, ONX). We examined the ability of FSG and ONX to photoprotect the antioxidant capacity of Vitamin E (VE), Vitamin C (VC), Vitamin E, and their derivatives, 6-hydroxy-2,-5,7,8-tetramethylchroman-2-carboxylic acid (Trolox, TLX) and L-ascorbic acid 6-palmitate (Vitamin C palmitate, VCP), from UV degradation. VE, VC, TLX, and VCP (100 μM solutions) acted as rapid antioxidants, scavenging >50% of the spontaneously formed free radical, 2,2-diphenyl-1-picrylhydrazyl (DPPH*, 200 μM), within 5 min in acetonitrile solutions. The vitamins and TLX were rendered slow antioxidants in the DDPH* assays, scavenging <50% of DPPH* within 30 min, after exposure of the acetonitrile solutions to UV radiation for 4 hours. VCP solutions were rendered moderate antioxidants, scavenging >50% of DPPH* within 30 min, after 4 hours exposure to UV radiation. FSG (100-1000 μM) was added to acetonitrile solutions of the vitamins and their derivatives to determine if FSG could photoprotect VE, TLX, VC, and VCP, allowing them to retain their antioxidant activities after 4 hours of UV irradiation. The addition of FSG, 500 and 1000 μM, allowed TLX and VE to retain rapid antioxidant activity after 4-hour UV exposure. VC retained rapid antioxidant capacity with 100 μM FSG after 4 hours of UV exposure. FSG performed comparably to slightly better than the commercial UV absorber, ONX, in protecting the antioxidant activities of vitamins and their derivatives from UV degradation. FSG also possessed intrinsic antioxidant capacity that ONX did not, which may have contributed to its better performance when mixed with the vitamins and their derivatives in the DPPH* assays. Keywords Antioxidant Á Feruloyl soy glycerols Á Vitamin C Á Vitamin E Á Ultraviolet degradation J Am Oil Chem Soc (2019) 96: 999-1009.Abbreviations AAPH 2,2 0 -azobis(2-amindinoprpoahe) dihydrochloride AVO avobenzone, 4-tert-butyl-4 0 -methoxydibenzoyl methane Supporting information Additional supporting information may be found online in the Supporting Information section at the end of the article.

Enzymatic Synthesis and Flash Chromatography Separation of 1,3-Diferuloyl-sn-Glycerol and 1-Feruloyl-sn-Glycerol

“…F 2 G and FG did not strongly absorb in the UVA I region. The UV absorbance spectra and λ max of F 2 G and FG were very similar to that of feruloylated soybean oil reported in ethanol and acetonitrile solutions [45]. The extinction coefficient, ε, of F 2 G (10-50 µM) and FG (10-100 µM) were determined in ethanol (Figure S6) and acetonitrile solutions (Figure S7) as the slope of the linear regression of absorbances at λ max , n = 3 trials.…”

“…F 2 G and FG possessed extinction coefficients higher than those reported for feruloylated soybean oil, 11,200 ± 58 and 13,400 ± 69 M −1 cm −1 , in ethanol and acetonitrile solutions, respectively [45]. Although FG did not absorb as strongly as the commercial UV absorbers, the F 2 G extinction coefficients were much higher than both Octinoxate, 24,000-25,400 M −1 cm −1 , reported in ethanol and acetonitrile solutions and Avobenzone, 34,000-30,800 M −1 cm −1 , reported in ethanol and acetonitrile solutions [45][46][47]. Retail formulations often contain multiple UV-absorbing ingredients, such as Octinoxate and Avobenzone, to protect against exposure to the full 240-400 nm UV absorbance spectrum.…”

“…The UV-absorbing characteristics of F 2 G and FG suggest that they could function as fungible replacements for commercial UVB-absorbing ingredients or be used in conjunction with commercial UV absorbers to enhance the UVA II absorbance of formulations. and Avobenzone, 34,000-30,800 M −1 cm −1 , reported in ethanol and acetonitrile solutions [45][46][47]. Retail formulations often contain multiple UV-absorbing ingredients, such as Octinoxate and Avobenzone, to protect against exposure to the full 240-400 nm UV absorbance spectrum.…”

Safe-Shields: Basal and Anti-UV Protection of Human Keratinocytes by Redox-Active Cerium Oxide Nanoparticles Prevents UVB-Induced Mutagenesis

“…To prevent this health hazard, the inclusion of antioxidants into nanoparticle-based sunscreens was often attempted, using carotenoids, vitamins (C and E), and plant extracts; however, these organic compounds have the main limitation of short-term duration due to lack of recycling ability in an abiotic environment such as outer skin. The consequence is that their topical use requires too frequent re-application, being, in fact, a non-sensible option [ 55 , 56 , 57 ]. To overcome this problem, in a recent work, it has been proposed to add biodegradable nanoparticles presenting both durable superoxide dismutase and catalase enzyme activity [ 58 ].…”

Exploring microbiome engineering as a strategy for improved thermal tolerance inExaiptasia diaphana

“…The cumulative results from these studies suggest that increased biologically available antioxidants could potentially mitigate bleaching and prolong the life of corals during climate change induced summer heat waves. Nevertheless, applying antioxidants directly onto corals may not be practical due to their short lifespan when exposed to seawater (King et al 2016 ) and ultraviolet radiation (Compton et al 2019 ), or desirable due to their potential impact on non‐target organisms. Instead, increasing natural antioxidant generation within the coral holobiont may be more effective and feasible.…”