Acylphloroglucinol Derivatives from the South African Helichrysum niveum and Their Biological Activities
AbstractPhytochemical investigation of aerial parts of Helichrysum niveum (H. niveum) using different chromatographic methods including semi-preparative HPLC afforded three new (1–3) and six known (4–10) acylphloroglucinols alongside a known dialcohol triterpene (11). The structures of the isolated compounds were characterized accordingly as 1-benzoyl-3 (3-methylbut-2-enylacetate)-phloroglucinol (helinivene A, 1), 1-benzoyl-3 (2S-hydroxyl-3-methylbut-3-enyl)-phloroglucinol (helinivene B, 2), 8-(2-methylpropanone)-3S,5,7-trihydroxyl-2,2-dimethoxychromane (helinivene C, 3), 1-(2-methylbutanone)-4-O-prenyl-phloroglucinol (4), 1-(2-methylpropanone)-4-O-prennyl-phloroglucinol (5), 1-(butanone)-3-prenyl-phloroglucinol (6), 1-(2-methylbutanone)-3-prenyl-phloroglucinol (7), 1-butanone-3-(3-methylbut-2-enylacetate)-phloroglucinol (8), 1-(2-methylpropanone)-3-prenylphloroglucinol (9), caespitate (10), and 3β-24-dihydroxyterexer-14-ene (11). Excellent total antioxidant capacities were demonstrated by helinivenes A and B (1 and 2) when measured as oxygen radicals absorbance capacity (ORAC), ferric-ion reducing antioxidant power (FRAP), trolox equivalent absorbance capacity (TEAC) and including the inhibition of Fe2+-induced lipid peroxidation (IC50 = 5.12 ± 0.90; 3.55 ± 1.92) µg/mL, while anti-tyrosinase activity at IC50 = 35.63 ± 4.67 and 26.72 ± 5.05 µg/mL were also observed for 1 and 2, respectively. This is the first chemical and in vitro biological study on H. niveum. These findings underpin new perspectives for the exploitation of these natural phenolic compounds in applications such as in the natural cosmeceutical and pharmaceutical sectors. View Full-Text
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Popoola, O.K.; Marnewick, J.L.; Rautenbach, F.; Iwuoha, E.I.; Hussein, A.A. Acylphloroglucinol Derivatives from the South African Helichrysum niveum and Their Biological Activities. Molecules 2015, 20, 17309-17324.
Popoola OK, Marnewick JL, Rautenbach F, Iwuoha EI, Hussein AA. Acylphloroglucinol Derivatives from the South African Helichrysum niveum and Their Biological Activities. Molecules. 2015; 20(9):17309-17324.Chicago/Turabian Style
Popoola, Olugbenga K.; Marnewick, Jeanine L.; Rautenbach, Fanie; Iwuoha, Emmanuel I.; Hussein, Ahmed A. 2015. "Acylphloroglucinol Derivatives from the South African Helichrysum niveum and Their Biological Activities." Molecules 20, no. 9: 17309-17324.