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Phytochemical 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.

Stoebe gnaphaloides Linnaeus, Systema Vegetabilium, ed. 13: 664. 1774, nom. illeg. RCN: 6728. Replaced synonym: Gnaphalium niveum L. (1753). Type not designated. Original material: as replaced synonym. Current name: Helichrysum niveum (L.) Less. (Asteraceae). Note: Although Hilliard & Burtt (in Bot. J. Linn. Soc. 82: 244, 259. 262. 1981) indicated Plukenet material in Herb. Sloane 100: 24 (BM-SL) as the lectotype of Gnaphalium niveum L. (the replaced synonym of S. gnaphaloides), this material was never seen by Linnaeus, is not associated with any Plukenet illustration, and is not original material for the earlier name., Published as part of Jarvis, Charlie, 2007, Chapter 7: Linnaean Plant Names and their Types (part S), pp. 806-877 in Order out of Chaos. Linnaean Plant Types and their Types, London :Linnaean Society of London in association with the Natural History Museum on page 876, DOI: 10.5281/zenodo.291971