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Molecules. 2015 Apr 20;20(4):7143-55. doi: 10.3390/molecules20047143.

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

Author information

1
Chemistry Department, University of Western Cape, Private Bag X17, Bellville 7535, South Africa. 3318925@myuwc.ac.za.
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. MarnewickJ@cput.ac.za.
3
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. rautenbachf@cput.ac.za.
4
Chemistry Department, University of Western Cape, Private Bag X17, Bellville 7535, South Africa. Fameer@uwc.ac.za.
5
Chemistry Department, University of Western Cape, Private Bag X17, Bellville 7535, South Africa. eiwuoha@uwc.ac.za.
6
Chemistry Department, University of Western Cape, Private Bag X17, Bellville 7535, South Africa. ahmohammed@uwc.ac.za.

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, 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 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.

PMID:
25903365
PMCID:
PMC6272301
DOI:
10.3390/molecules20047143
[Indexed for MEDLINE]
Free PMC Article

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