PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
2011 | nr 217 | 119--132
Tytuł artykułu

Long-Chain Esters of Phenolic Acids as Multifuntional Components of Cosmetic Products

Warianty tytułu
Długołańcuchowe estry kwasów fenolowych jako wielofunkcyjne składniki produktów kosmetycznych
Języki publikacji
EN
Abstrakty
EN
Phenolic acids are widely spread throughout the plant kingdom. Therefore, one vast area of interest for phenolic acids has been in food quality. Phenolic acids and their derivatives exhibit strong antioxidant activity against wide spectrum of reactive oxygen species. This property can be used to inhibit the oxidation processes that have place in cosmetic emulsions containing unsaturated fatty acids. Moreover, phenolic acids and their alkyl esters have anti-allergic, anti-inflammatory, anti-microbial properties. In the structure of long-chain phenolic acids esters both the hydrophilic and the hydrophobic regions can by distinguished what suggests possible surface activity of these compounds. In this study we present the first results of our study on long-chain ferulic acid esters as novel components for cosmetic industry. Its derivatives with the tetradecyl, hexadecyl and octadecyl chains were synthesised and their structure was confirmed by IR spectroscopy. The HLB values, calculated according to the IOB system, suggest that newly synthesised long-chain ferulic acid esters could be used as multifunctional ingredients in cosmetic formulations: with antioxidant, anti-foaming and W/O emulgating functions. (original abstract)
Kwasy fenolowe są związkami szeroko rozpowszechnionymi w świecie roślinnym, co powoduje, że cieszą się one szczególnym zainteresowaniem w kontekście kształtowania jakości żywności. Zarówno kwasy fenolowe, jak i ich pochodne wykazują silną aktywność przeciwutleniającą, polegającą na dezaktywacji reaktywnych form tlenu. Właściwości te mogą być wykorzystywane do hamowania procesów oksydacyjnych występujących w emulsjach zawierających nienasycone kwasy tłuszczowe. Ponadto kwasy fenolowe i ich alkilowe estry wykazują działanie przeciwalergiczne, przeciwzapalne i przeciwdrobnoustrojowe. Budowa cząsteczkowa długołańcuchowych estrów kwasów fenolowych, charakteryzująca się występowaniem dwóch wyraźnych części: hydrofilowej i hydrofobowej, wskazuje na występowanie właściwości powierzchniowo czynnych tych związków. W artykule prezentujemy wstępne wyniki badań dotyczących długołańcuchowych estrów kwasów fenolowych, które mogą znaleźć zastosowania jako nowe składniki wyrobów kosmetycznych. Wykonano syntezę tetradecylowych, heksadecylowych oraz oktadecylowych pochodnych kwasu ferulowego, a następnie potwierdzono ich strukturę na podstawie analizy widm w podczerwieni. Wartości HLBG wyznaczone na podstawie systemu IOB sugerują, że otrzymane długołańcuchowe estry kwasu ferulowego mogą być wykorzystywane w recepturach kosmetycznych jako składniki pełniące również funkcje środków przeciwpieniących oraz emulgatorów typu W/O. (abstrakt oryginalny)
Rocznik
Numer
Strony
119--132
Opis fizyczny
Twórcy
  • Poznań University of Economics, Poland
  • Poznań University of Economics, Poland
Bibliografia
  • Andjelkovic, M., Camp, J. van, Meulenaer, B. de, Depaemelaere, G., Socaciu, C., Verloo, M., Verhe, R., 2006, Iron-chelation Properties of Phenolic Acids Bearing Catechol and Galloyl Groups, Food Chemistry, vol. 98, iss. 1, pp. 23-31.
  • Anselmi, C., Centini, M., Andreassi, M., Buonocore, A., La Rosa, C., Facino, R.M., Sega, A., Tsuno, F., 2004, Conformational Analysis: A Tool for the Elucidation of the Antioxidant Properties of Ferulic Acid Derivatives in Membrane Models, Journal of Pharmaceutical and Biomedical Analysis, vol. 35, no. 5, pp. 1241-1249.
  • Chalas, J., Claise, C., Edeas, M., Messaoudi, C., Vergnes, L., Abella, A., Lindenbaum, A., 2001, Effect of Ethyl Esterification of Phenolic Acids on Low-density Lipoprotein Oxidation, Biomedicine & Pharmacotherapy, vol. 55, iss. 1, pp. 54-60.
  • Clifford, M.N., 1999a, Appendix I. A Nomenclature for Phenols with Special Reference to Tea, Washington, DC, 11/1999, CRC Press LLC: Boca Raton, Florida, vol. 41, S5, pp. 393-397.
  • Clifford, M.N., 1999b, Chlorogenic Acids and Other Cinnamates - Nature, Occurrence, and Dietary Burden, Journal of the Science Food and Agriculture, vol. 79, iss. 3, pp. 362-372.
  • Commision Decision (2006/257/EC) of 9 February 2006 amending Decision 96/335/EC establishing an inventory and a common nomenclature of ingredients employed in cosmetic products.
  • Croteau, R., Kutchan, T.M., Lewis, N.G., 2000, Natural Products (Secondary Metabolites), in: Buchanan, B., Gruissem, W., Jones, R. (eds.), Biochemistry & Molecular Biology of Plants, American Society of Plant Physiologists, Rockville, MD, pp. 1250-1318.
  • Cuvelier, M.E., Richard, H., Berst, C., 1992, Comparison of the Antioxidative Activity of Some Acid Phenols: Structure-activity Relationship, Bioscience, Biotechnology & Biochemistry, vol. 56, iss. 2, pp. 324-325.
  • Ellnain-Wojtaszek, M., Kurczynski, Z., Kasprzak, J., 2001, Analysis of the Content of Flavonoids, Phenolic Acids as well as Free Radicals from Ginkgo Biloba L. Leaves During the Vegetative Cycle, Acta Poloniae Pharmaceutica, vol. 58, no. 3, pp. 205-209.
  • Fernandez-Zurbano, P., Ferreira, V., Escudero, A., Cacho, J., 1998, Role of Hydroxycinamic Acids and Flavanols in the Oxidation and Browning of White Wines, Journal of Agricultural and Food Chemistry, vol. 46, iss. 12, pp. 4937-4944.
  • Fiuza, S.M., Gomes, C., Teixeira, L.J., Girao da Cruz, M.T.,. Cordeiro, M.N.D., Milhazes, S.N., Borges, F., Marques, M.P.M., 2004, Phenolic Acid Derivatives with Potential Anticancer Properties - a Structure-activity Relationship Study. Part 1: Methyl, Propyl and Octyl Esters of Caffeic and Gallic Acids, Bioorganic & Medicinal Chemistry, vol. 12, iss. 13, pp. 3581-3589.
  • Grunberger, D., Banerjee, R., Eisinger, K., Oltz, E.M., Efros, L., Caldwell, M., Estevez, V., Nakanishi, K., 1988, Preferential Cytotoxicity on Tumor Cells by Caffeic Acid Phenethyl Ester Isolated from Propolis, Experientia, vol. 44, pp. 230-232.
  • Herrmann, K., 1989, Occurrence and Content of Hydroxycinnamic and Hydroxybenzoic Acid Compounds in Foods, Critical Reviews in Food Science and Nutrition, vol. 28, iss. 4, pp. 315-347.
  • Jayaprakasam, B., Vanisree, M., Zhang, Y., Dewitt, D.L., Nair, M.G., 2006, Impact of Alkyl Esters of Caffeic and Ferulic Acids on Tumor Cell Proliferation, Cyclooxygenase Enzyme, and Lipid Peroxidation, Journal of Agriculture and Food Chemistry, vol. 54, iss. 15, pp. 5375-5381.
  • Koshihara, Y., Neichi, T., Murota, S.I., Lao, A.N., Fujimoto, Y., Tatsuno, T., 1984, Caffeic Acid Is a Selective Inhibitor for Leukotriene Biosynthesis, Biochimica et Biophysica Acta, vol. 792, iss. 1, pp. 92-97.
  • Kubo, I., Fujita, K., Nihei, K., Masuoka, N., 2003, Non-antibiotic Antibacterial Activity of Dodecyl Gallate, Bioorganic & Medicinal Chemistry, vol. 11, no. 4, pp. 573-580.
  • Kubo, I., Xiao, P., Fujita, K., 2001, Antifungal Activity of Octyl Gallate: Structural Criteria and Mode of Action, Bioorganic & Medicinal Chemistry Letters, vol. 11, no. 3, pp. 347-350.
  • Kubo, I., Xiao, P., Fujita, K., 2002, Anti-MRSA Activity of Alkyl Gallates, Bioorganic & Medicinal Chemistry Letters, vol. 12, no. 2, pp. 113-116.
  • Lam, T.B.T., Kadoya, K., Iiyama, K., 2001, Bonding of Hydroxycinnamic Acids to Lignin: Ferulic and p-Coumaric Acids Are Predominantly Linked at the Benzyl Position of Lignin, Not the a-Position, in Grass Cell Walls, Phytochemistry vol. 57, iss. 6, pp. 987-992.
  • Laranjinha, J., 2002, Caffeic Acid and Related Antioxidant Compounds: Biochemical and Cellular Effects, in: Packer, L., Cadenas, E. (eds.), Handbook of Antioxidants, Marcel Dekker, Inc., New York, pp. 279-302.
  • Leal-Calderon, F., Thivilliers, F., Schmitt, V., 2007, Structured Emulsions, Current Opinion in Colloid & Interface Science, vol. 12, iss. 4-5, pp. 206-212.
  • Lodovici, M., Guglielmi, F., Meoni, M., Dolara, P., 2001, Effect of Natural Phenolic Acids on DNA Oxidation in Vitro, Food Chemistry and Toxicology, vol. 39, iss. 12, pp. 1205-1210.
  • Maggi-Capeyron, M.F., Ceballos, P., Cristol, J.P., Delbosc, S., Le Doucen, C., Pons, M., Leger, C.L., Descomps, B., 2001, Wine Phenolic Antioxidants Inhibit ap-1 Transcriptional Activity, Journal of Agricultural and Food Chemistry, vol. 49, iss. 11, pp. 5646-5652.
  • Mason, T.G., 1999, New Fundamental Concepts in Emulsion Rheology, Current Opinion in Colloid & Interface Science, vol. 4, iss. 3, pp. 231-238.
  • Merkl, R., Hradkova, I., Filip, V., Smidrkal, J., 2010, Antimicrobial and Antioxidant Properties of Phenolic Acids Alkyl Esters, Czech Journal of Food Sciences, vol. 28, no. 4, pp. 275-279.
  • Mysiak, B., Tendaj, M., 2008, Content of Phenolic Acids in Edible Parts of Some Alliums Species Grown for the Green Bunching, Acta Scientiarum Polonorum, Hortorum Cultus, vol. 7, no. 4, pp. 7-62.
  • Nardini, M., Ghiselli, A., 2004, Determination of Free and Bound Phenolic Acids in Beer, Food Chemistry, vol. 84, iss. 1, pp. 137-143.
  • Olthof, M.R., Hollman, P.C.H., Katan, M., 2001, Chlorogenic Acid and Caffeic Acid Are Absorbed in Humans, Human Nutrition and Metabolism, vol. 131, pp. 66-71.
  • Rice-Evans, C.A., Miller, N.J., Paganga, G., 1996, Structure - Antioxidant Activity Relationships of Flavonoids and Phenolic Acids, Free Radicals in Biology and Medicine, vol. 20, iss. 7, pp. 933-956.
  • Robbins, R.J., 2003, Phenolic Acids in Foods: An Overview of Analytical Methodology, Journal of Agricultural and Food Chemistry, vol. 51, iss. 10, pp. 2866-2887.
  • Sasaki, K., Alamed, J., Weiss, J., Villeneuve, P., Lopez Giraldo, L.J., Lecomte, J., Figueroa-Espinoza, M.C., Decker, E.A., 2010, Relationship Between the Physical Properties of Chlorogenic Acid Esters and Their Ability to Inhibit Lipid Oxidation in Oil-in-Water Emulsions, Food Chemistry, vol. 118, iss. 3, pp. 830-835.
  • Scalbert, A., Williamson, G., 2000, Dietary Intake and Bioavailablity of Polyphenols, Journal of Nutrition, vol. 130, no. 8, pp. 2073S-2085S.
  • Shahidi, F., Nacsk, M., 1995, Food Phenolics: Sources, Chemistry, Effects, and Application, Technomic Publishing Company, Inc., Lancaster, PA.
  • Sikorska, M., Matlawska, I., Glowniak, K., Zgorka, G., 2000, Qualitative and Quantitative Analysis of Phenolic Acids in Asclepias Syriaca L, Acta Poloniae Pharmaceutica, vol. 57, no. 1, pp. 69-72.
  • Soni, M.G., Carabin, I.G., Burdock, G.A., 2005, Safety Assessment of Esters of p-Hydroxybenzoic Acid (Parabens), Food and Chemical Toxicology, vol. 43, iss. 7, pp. 985-1015.
  • Soto, A.M., Justicia, H., Wray, J.W., Sonnenschein, C., 1991, p-Nonyl-phenol: an Estrogenic Xenobiotic Released from "Modified" Polystyrene, Environmental Health Perspectives, vol. 92, pp. 167-173.
  • Stalikas, C.D., 2007, Extraction, Separation, and Detection Methods for Phenolic Acids and Flavonoids, Journal of Separation Science, vol. 30, no. 18, pp. 3268-3295.
  • Stuart, M., 1995, Modern Infrared Spectroscopy, John Wiley & Sons Ltd., New York.
  • Szwajgier, D., Jakubczyk, A., 2011, Production of Extracellular Ferulic Acid Esterases by Lactobacillus Strains Using Natural and Synthetic Carbon Sources, Acta Scientiarum Polonorum. Technologia Alimentaria, vol. 10, no. 3, pp. 287-302.
  • Tan, S.C., 2000, Determinants of Eating Quality in Fruits and Vegetables, Proceedings of the Nutrition Society of Australia, vol. 24, pp. 183-190.
  • Tomas-Barberan, F.A., Espin, J.C., 2001, Phenolic Compounds and Related Enzymes as Determinants of Quality in Fruits and Vegetables, Journal of the Science of Food and Agriculture, vol. 81, no. 9, pp. 853-876.
  • Trombino, S., Cassano, R., Muzzalupo, R., Pingitore, A., Cione, E., Picci, N., 2009, Stearyl Ferulate-based Solid Lipid Nanoparticles for the Encapsulation and Stabilization of β-Carotene and α-Tocopherol, Colloids and Surfaces B: Biointerfaces, vol. 72, iss. 2, pp. 181-187.
  • Tsuno Food Industrial Co., Ferulid Acid [online] http://www.tsuno.co.jp/e/04/05/index.htm [access: 21.05.2011].
  • Uozaki, M., Yamasaki, H., Katsuyama, Y., Higuchi, M., Higuti, T.A., Koyamaa, H., 2007, Antiviral Effect of Octyl Gallate Against DNA and RNA Viruses, Antiviral Research, vol. 73, iss. 2, pp. 85-91.
  • Williamson, G., Plumb, G.W., Garcia-Conesa, M.T., 1999, Glycosylation, Esterification and Polymerization of Flavonoids and Hydroxycinnamates: Effects on Antioxidant Properties, Basic Life Sciences, vol. 66, pp. 483-494.
  • Zheng, W., Wang, S.Y., 2001, Effect of Plant Growth Temperature on Antioxidant Capacity in Strawberry, Journal of Agriculture and Food Chemistry, vol. 49, iss. 10, pp. 4977-4982.
  • Zieliński, R., 2009, Surfaktanty. Budowa, właściwości, zastosowania, Wydawnictwo Uniwersytetu Ekonomicznego w Poznaniu, Poznań.
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.ekon-element-000171215521

Zgłoszenie zostało wysłane

Zgłoszenie zostało wysłane

Musisz być zalogowany aby pisać komentarze.
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.