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

摘要

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) andmosloflavone (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, whilecompounds 6, 8–10 were isolated for the first time from the genus Helichrysum. The totalextract of H. teretifolium showed potent antioxidant activity. When tested for total antioxidantcapacity compound 3 possesses moderate biological activity compared to 2, which displayedsome 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 Fe2+-induced lipidperoxidation (IC50 = 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)× 106 and peroxyl radical (17.836 ± 2.90; 12.545 ± 5.07) × 103 µM TE/g were alsoobserved for compounds 7 and 8, respectively. In conclusion, H. teretifolium total extract represents a rich source of bioactive constituents with potent antioxidant and moderateanti-tyrosinase and anti-elastase activities that can help to avert accumulation of freeradicals in the body, and could therefore be good candidates for the prevention and/ortreatment of skin-related conditions, such as aging. This is the first scientific report on thechemical and biological profile of H. teretifolium.