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      Acylphloroglucinol Derivatives from the South African Helichrysum niveum and Their Biological Activities

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          Abstract

          Phytochemical investigation of aerial parts of Helichrysum niveum ( H. niveum) using different chromatographic methods including semi-preparative HPLC afforded three new ( 13) and six known ( 410) 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 (2 S-hydroxyl-3-methylbut-3-enyl)-phloroglucinol (helinivene B, 2), 8-(2-methylpropanone)-3 S,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 Fe 2+-induced lipid peroxidation (IC 50 = 5.12 ± 0.90; 3.55 ± 1.92) µg/mL, while anti-tyrosinase activity at IC 50 = 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.

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          An Updated Review of Tyrosinase Inhibitors

          Tyrosinase is a multifunctional, glycosylated, and copper-containing oxidase, which catalyzes the first two steps in mammalian melanogenesis and is responsible for enzymatic browning reactions in damaged fruits during post-harvest handling and processing. Neither hyperpigmentation in human skin nor enzymatic browning in fruits are desirable. These phenomena have encouraged researchers to seek new potent tyrosinase inhibitors for use in foods and cosmetics. This article surveys tyrosinase inhibitors newly discovered from natural and synthetic sources. The inhibitory strength is compared with that of a standard inhibitor, kojic acid, and their inhibitory mechanisms are discussed.
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            Damage to skin extracellular matrix induced by UV exposure.

            Chronic exposure to environmental ultraviolet radiation (UVR) plays a key role in both photocarcinogenesis and induction of accelerated skin aging. Although the spatiotemporal consequences of UVR exposure for the composition and architecture of the dermal extracellular matrix (ECM) are well characterized, the pathogenesis of photoaging remains poorly defined. Given the compelling evidence for the role of reactive oxygen species (ROS) as mediators of photoaging, UVR-exposed human skin may be an accessible model system in which to characterize the role of oxidative damage in both internal and external tissues.
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              Anti-Aging Effect of Adipose-Derived Stem Cells in a Mouse Model of Skin Aging Induced by D-Galactose

              Introduction Glycation products accumulate during aging of slowly renewing tissue, including skin, and are suggested as an important mechanism underlying the skin aging process. Adipose-derived cells are widely used in the clinic to treat ischemic diseases and enhance wound healing. Interestingly, adipose-derived stem cells (ASCs) are also effective in anti-aging therapy, although the mechanism underlying their effects remains unknown. The purpose of the present study was to examine the anti-aging effect of ASCs in a D-galactose-induced aging animal model and to clarify the underlying mechanism. Materials and Methods Six-week-old nude mice were subcutaneously injected with D-gal daily for 8 weeks. Two weeks after completion of treatment, mice were randomized to receive subcutaneous injections of 106 green fluorescent protein (GFP)-expressing ASCs, aminoguanidine (AG) or phosphate-buffered saline (PBS). Control mice received no treatment. We examined tissue histology and determined the activity of senescence-associated molecular markers such as superoxide dismutase (SOD) and malondialdehyde (MDA). Results Transplanted ASCs were detectable for 14 days and their GFP signal disappeared at day 28 after injection. ASCs inhibited advanced glycation end product (AGE) levels in our animal model as well as increased the SOD level and decreased the MDA level, all of which act to reverse the aging phenotype in a similar way to AG, an inhibitor of AGE formation. Furthermore, ASCs released angiogenic factors in vivo such as vascular endothelial growth factor, suggesting a skin trophic effect. Conclusions These results demonstrate that ASCs may contribute to the regeneration of skin during aging. In addition, the data shows that ASCs provide a functional benefit by glycation suppression, antioxidation, and trophic effects in a mouse model of aging.
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                Author and article information

                Contributors
                Role: Academic Editor
                Journal
                Molecules
                Molecules
                molecules
                Molecules
                MDPI
                1420-3049
                18 September 2015
                September 2015
                : 20
                : 9
                : 17309-17324
                Affiliations
                [1 ]Chemistry Department, University of Western Cape, Private Bag X17, Bellville 7535, South Africa; E-Mails: 3318925@ 123456myuwc.ac.za (O.K.P.); eiwuoha@ 123456uwc.ac.za (E.I.I.)
                [2 ]Oxidative Stress Research Centre, Faculty of Health and Wellness Sciences, Cape Peninsula University of Technology, P. O. BOX 1906, Bellville 7535, South Africa; E-Mails: MarnewickJ@ 123456cput.ac.za (J.L.M.); rautenbachf@ 123456cput.ac.za (F.R.)
                Author notes
                [* ]Author to whom correspondence should be addressed; E-Mail: ahmohammed@ 123456uwc.ac.za ; Tel.: +27-21-959-2262; Fax: 27-21-959-3055.
                Article
                molecules-20-17309
                10.3390/molecules200917309
                6332446
                26393563
                b2a15a50-fd7a-4325-a3b0-e383dd3ce1fb
                © 2015 by the authors.

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license ( http://creativecommons.org/licenses/by/4.0/).

                History
                : 23 July 2015
                : 10 September 2015
                Categories
                Article

                helichrysum niveum,asteraceae,phloroglucinols,antioxidant,anti-aging

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