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Molecules 2015, 20(4), 7143-7155; doi:10.3390/molecules20047143

Inhibition of Oxidative Stress and Skin Aging-Related Enzymes by Prenylated Chalcones and Other Flavonoids from Helichrysum teretifolium

1
Chemistry Department, University of Western Cape, Private Bag X17, Bellville 7535, South Africa
2
Oxidative Stress Research Centre, Institute of Biomedical and Microbial Biotechnology, Faculty of Health and Wellness Sciences, Cape Peninsula University of Technology, P O BOX 1906, Bellville 7535, South Africa
*
Author to whom correspondence should be addressed.
Academic Editor: Isabel C. F. R. Ferreira
Received: 8 March 2015 / Revised: 9 April 2015 / Accepted: 14 April 2015 / Published: 20 April 2015
(This article belongs to the Collection Bioactive Compounds)
View Full-Text   |   Download PDF [736 KB, uploaded 20 April 2015]   |  

Abstract

Ten flavonoid-related structures viz. heliteretifolin (1), isoxanthohumol (2), 2',4',6'-trihydroxy-3'-prenylchalcone (3), isoglabranin (4), glabranin (5), 7-methoxy-isoglabranin (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, 810 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 Fe2+-induced lipid peroxidation (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 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. View Full-Text
Keywords: Helichrysum teretifolium; anti-tyrosinase; anti-elastase; oxidative stress; anti-aging; flavonoids Helichrysum teretifolium; anti-tyrosinase; anti-elastase; oxidative stress; anti-aging; flavonoids
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Popoola, O.K.; Marnewick, J.L.; Rautenbach, F.; Ameer, F.; Iwuoha, E.I.; Hussein, A.A. Inhibition of Oxidative Stress and Skin Aging-Related Enzymes by Prenylated Chalcones and Other Flavonoids from Helichrysum teretifolium. Molecules 2015, 20, 7143-7155.

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