Inhibition of oxidative stress and skin aging-related enzymes by prenylated chalcones and other flavonoids from Helichrysum teretifolium

Abstract

Ten flavonoid-related structures viz. heliteretifolin (1), isoxanthohumol (2), 2′,4′,6′-trihydroxy-3′-prenylchalcone (3), isoglabranin (4), glabranin (5), 7-methoxyisoglabranin (6), quercetin (7), 4′-methoxyquercetin (8), 4′-methoxykaempferol (9) and mosloflavone (10) were isolated from a H. teretifolium methanolic extract and identified. One of them (compound 1) is reported for the first time from a natural source, while compounds 6, 8-10 were isolated for the first time from the genus Helichrysum. The total extract of H. teretifolium showed potent antioxidant activity. When tested for total antioxidant capacity compound 3 possesses moderate biological activity compared to 2, which displayed some of the highest TEAC values (4529.01 ± 2.44; 4170.66 ± 6.72) μM TE/g, respectively. Compounds 7 and 8 demonstrated the highest inhibitory activities on Fe 2+ -induced lipid peroxidation (IC 50 = 2.931; 6.449 μg/mL); tyrosinase (8.092; 27.573) and elastase (43.342; 86.548). Additionally, the total antioxidant capacities measured as FRAP (4816.31 ± 7.42; 3584.17 ± 0.54) μM AAE/g, and ORAC for hydroxyl radical (7.265 ± 0.71; 6.779 ± 3.40) × 10 6 and peroxyl radical (17.836 ± 2.90; 12.545 ± 5.07) × 103 μM TE/g were also observed for compounds 7 and 8, respectively. In conclusion, H. teretifolium total extract represents a rich source of bioactive constituents with potent antioxidant and moderate anti-tyrosinase and anti-elastase activities that can help to avert accumulation of free radicals in the body, and could therefore be good candidates for the prevention and/or treatment of skin-related conditions, such as aging. This is the first scientific report on the chemical and biological profile of H. teretifolium.