Abstract
Free radicals and reactive oxygen species (ROS) caused by UV exposure or other environmental factors are critical players in cellular damage and aging. In order to develop a new antiphotoaging agent, this work focused on the antioxidant effects of the extract of tinged autumnal leaves ofAcer palmatum. One compound was isolated from an ethyl acetate soluble fraction of theA. palmatum extract using silica gel column chromatography. The chemical structure was identified as apigenin-8-C-beta-D-glucopyranoside, more commonly known as vitexin, by spectral analysis including LC-MS, FT-IR, UV,1H-, and13C-NMR. The biological activities of vitexin were investigated for the potential application of its anti-aging effects in the cosmetic field. Vitexin inhibited superoxide radicals by about 70% at a concentration of 100 μg/mL and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals by about 60% at a concentration of 100 μg/mL Intracellular ROS scavenging activity was indicated by increases in dichlorofluorescein (DCF) fluorescence upon exposure to UVB 20 mJ/cm2 in cultured human dermal fibroblasts (HDFs) after the treatment of vitexin. The results show that oxidation of 5-(6-)chloromethyl-2′,7′-dichlorodihydrofluorescein diacetate (CM-H2DCFDA) is inhibited by vitexin effectively and that vitexin has a potent free radical scavenging activity in UVB-irradiated HDFs. In ROS imaging using a confocal microscope we visualized DCF fluorescence in HDFs directly. In conclusion, our findings suggest that vitexin can be effectively used for the prevention of UV-induced adverse skin reactions such as free radical production and skin cell damage.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Afitlhile, M. M., Dent, R. M., and Cowan, A. K., Changes in carotenoid composition in senescing leaves ofHordeum vulgare L. cv. Dyan.J. Plant Physiol., 142, 4349 (1993).
Aritomi, M., Chemical constituents in Aceraceous plants. 1. Flavonoid constituents in the leaves ofAcer palmatum Thunberg.Yakugaku Zasshi, 83, 737–740 (1963).
Aritomi, M., Chemical constituents in Aceraceous plants. 3. Flavonoid constituents in leaves ofAcer cissifolium K. Koch.Chem. Pharm. Bull., 12, 841–843 (1964).
Bandoniene, D. and Murkovic, M., On-line HPLC-DPPH screening method for evaluation of radical scavenging phenols extracted from apples (Malus domestica L.).J. Agric. Food Chem., 50, 2482–2487 (2002).
Bestwick, C. S. and Milne, L., Quercetin modifies reactive oxygen levels but exerts only partial protection against oxidative stress within HL-60 cells.Biochim. Biophys. Acta, 1528, 48–59 (2001).
Blois, M. S., Antioxidant determinations by the use of a stable free radical.Nature, 181, 1199–1200 (1958).
Bonina, F., Puglia, C., Ventura, D., Aquino, R., Tortora, S., Sacchi, A., Saija, A., Tomaino, A., Pellegrino, M. L., and de Capariis P.,In vitro antioxidant andin vivo photoprotective effects of a lyophilized extract ofCapparis spinosa L. buds.J. Cosmet. Sci., 53, 321–335 (2002).
Bors, W. and Michel, C., Chemistry of the antioxidant effect of polyphenols.Ann. N. Y. Acad. Sci., 957, 57–69 (2002).
Cathcart, R., Schwiers, E., and Ames, B. N., Detection of picomole levels of hydroperoxides using a fluorescent dichlorofluorescein assay.Anal. Biochem., 134, 111–116 (1983).
Dauborn, B. and Brueggemann, W., A spontaneous point mutation in rubisco large subunit gene impairing holoenzyme assemblyrenders the IV beta plastome mutant of Oenothera extremely light and chilling sensitive.Physiol. Plant, 104, 116–124(1998).
Feild, T. S., Lee, D. W., and Holbrook, N. M., Why leaves turn red in autumn. The role of anthocyanins in senescing leaves of red-osier dogwood,Plant Physiol., 127, 566–574 (2001).
Furuno, K., Akasako, T., and Sugihara, N., The contribution of the pyrogallol moiety to the superoxide radical scavenging activity of flavonoids.Biol. Pharm. Bull., 25, 19–23 (2002).
Gaitan, E., Cooksey, R. C, Legan, J., and Lindsay, R. H., Antithyroid effectsin vivo andin vitro of vitexin: a C-glycosylflavone in millet.J. Clin. Endocrinol. Metab., 80, 1144–1147 (1995).
Greenham, J., Harbome, J. B., and Williams, C. A., Identification of lipophilic flavones and flavonols by comparative HPLC, TLC, and UV spectral analysis.Phytochem. Anal., 14, 100–118 (2003).
Ham, I. H., Oh, I. S., Whang, W. K., and Kim I. H., Pharmaco-constituents of Korean cultivated Rhubarb leaves-the flavonoids from leaves.Yakhak Hoeji, 38, 469–475 (1994).
Harborne, J. B., Nature, Distribution and function of plant flavonoids.Prog. Clin. Biol. Res., 213, 15–24 (1986).
Harman, D., Role of free radical reactions in aging and disease.J. Geriat. Dermatol., 5, 114–127 (1997).
Katiyar, S. K., Afaq, F., Perex, A., and Mukhtar, H., Green tea polyphenol (-)-epigallocatechin-3-gallate treatment of human skin inhibits ultraviolet radiation-induced oxidative stress.Carcinogenesis, 22, 287–294 (2001).
Khettab, N., Amory, M. C., Brigand, G., Bousquet, B., and Combre, A., Photoprotective effect of vitamins A and E on polyamine and oxygenated free radical metabolism in hairless mouse epidermis.Biochimie, 70, 1709–1713 (1988).
LeBel, C. P., Ischiropoulos, H., and Bondy, S. C, Evaluation of the probe 2,7-dichlorofluorescein as an indicator of reactive oxygen species formation and oxidative stress.Chem. Res. Toxicol., 5, 227–231 (1992).
Lee, B. C., Bae, J. T., Pyo, H. B., Choe, T. B., Kim, S. W., Hwang, H. J., and Yun, J. W., Biological activities of the polysaccharides produced from submerged culture of the edible BasidiomyceteGrifola Frondosa.Enzyme Microb. Technol., 6274, 1–8 (2003).
Mathews-Roth, M. M., Carotenoid pigment administration and the delay in development of UVB-induced tumors.Photochem. Photobiol., 42, 35–38 (1983).
Middleton, E. Jr., Kandaswami, C., and Theoharides, T. C., The effects of plant flavonoids on mammalian cells: Implications for inflammation, heart disease, and cancer. Pharmacol. Rev., 52, 673–751 (2000).
Nijveldt, R. J., Nood, E., Hoorn, D. EC, Boelens, P. G., Norren, K., and Leeuwen, P.AM, Flavonoids: a review of probable mechanisms of action and potential applications.Am. J. Clin. Nutr., 74, 418–425 (2001).
Norins, A. L, Free radical formation in the skin following exposure to ultraviolet light.J. Invest. Dermatol., 39, 445–448 (1962).
Oh, I. S., Whang, W. K., and Kim, I. H., Constituents ofCrataegus pinnatifida val. psilosa Leaves (II) Flavonoids from BuOH fraction.Arch. Pharm. Res., 17, 314–317 (1994).
Prabhakar, M. C., Bano, H., Kumar, I., Shamsi, M. A., and Khan, M. S. Y, Pharmacological investigations on vitexin.Planta medica, 43, 396–403 (1981).
Riipi, M., Ossipov V., Lempa, K., Haukioja, E., Koricheva, J., Ossipova, S., and Pihlaja, K., Seasonal changes in birch leaf chemistry: are there trade-offs between leaf growth and accumulation of phenolics?Oecologia, 130, 380–390 (2002).
Ryoo, Y. W., Suh, S. I., Mun, K. C., Kim, B. C., and Lee, K. S., The effects of the melatonin on ultraviolet-B irradiated cultured dermal fibroblasts.J. Dermatol. Sci., 27, 162–169 (2001).
Savini, I., DAngelo, I., Ranalli, M., Melino, G., and Avigliano, L, Ascorbic acid maintenance in HaCaT cells prevents radical formation and apoptosis by UVB.Free Radio. Biol. Med., 26, 1172–1180 (1999).
Seo, S. Y., Kim, E. Y., Kim, H., and Gwang, B. J, Neuroprotective effect of high glucose agains NMDA, free radical and oxygen-glucose deprivation through enhanced mitochondrial potentials.J. Neurosci., 19, 8849–8855 (1999).
Shibamoto, T., Sulfur-containing heterocyclic compounds with antioxidative activity.Am. Chem. Soc, 564, 247–256 (1994).
Tampo, Y., Kotamraju, S., Chitambar, C. R., Kalivendi, S. V., Keszler, A., Joseph, J., and Kalyanaraman, B., Oxidative stress-induced iron signaling is responsible for peroxide-dependent oxidation of dichlorodihydrofluorescein in endothelial cells.Circ. Res., 92, 56–63 (2003).
Tobi, S. E., Gilbert, M., Paul, N., and McMillan, T. J., The green tea polyphenol, epigallocatechin-3-gallate, protects against the oxidative cellular and genotoxic damage of UVA radiation.Int. J. Cancer, 102, 439–444 (2002).
Trayner, I. D., Rayner, A. P., Freeamn, G. E., and Farzaneh, F., Quantitative multiwell myeloid differentiation assay using dichlorodihydrofluorescein diacetate (H2DCFDA) or dihydrorhodamine 123 (H2R123).J. Immunol. Methods, 186, 275–284 (1995).
Yoo, S. W., Kim, J. S., Kang, S. S., Son, K. H., Chang, H. W., Kim, H. P., Bae, K. H., and Lee, C. O., Constituents of the fruits and leaves ofEuodia danielli.Arch. Pharm. Res., 25, 824–830 (2002).
Young, A. J., Wellings R., and Britton G., The fate of chloroplast pigments during senescence of primary leaves ofHordeum vulgare andAvena sativum.J. Plant Physiol., 137, 701–705 (1991).
Zhang, H., Joseph, J., Felix, C., and Kalyanaraman, B., Bicarbonate enhances the hydroxylation, nitration, and peroxidation reactions catalyzed by copper, zinc superoxide dismutase: intermediacy of carbomate anion radical.J. Biol. Chem., 275, 14038–14045 (2000).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kim, J.H., Lee, B.C., Kim, J.H. et al. The isolation and antioxidative effects of vitexin fromAcer palmatum . Arch Pharm Res 28, 195–202 (2005). https://doi.org/10.1007/BF02977715
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02977715