Alquilresorcinoles: Compuestos Naturales con Importancia Biológica

  • Eleana R. Suaza-García Universidad Militar Nueva Granada
  • Ericsson Coy-Barrera Universidad Militar Nueva Granada
Palabras clave: Alquilresorcinoles, Lípidos resorcinólicos, fuentes de alquilresorcinoles, identificación de alquilresorcinoles

Resumen

Los alquilresorcinoles (AR) son un grupo de metabolitos secundarios no isoprenoides, pertenecientes a la familia de los fenoles, a los que se les confieren propiedades biológicamente importantes tales como: antifúngica, antibacterial, citotóxica, antitumoral, antioxidante y como biomarcadores. Estos metabolitos han sido encontrados en diferentes organismos tales como: plantas, hongos, metazoos y bacterias; siendo las rizobacterias una fuente importante de AR. En la presente revisión se presentan algunas de las características más importantes de estos metabolitos con un enfoque descriptivo con el propósito de reseñar la importancia biológica de estos compuestos naturales.

Descargas

Los datos de descargas todavía no están disponibles.

Lenguajes:

es

Referencias bibliográficas

Adawadkar P. y El Sohly M. 1981. Isolation, purification and antimicrobial activity of anacadic acids from Ginkgo biloba fruits. Fitoterapia. 52: 129-135.

Alonso E., Ramón E. y Yus M. 1997. Simple synthesis of 5-substituted resorcinols: a revised family of interesting bioactive molecules. The Journal of Organic Chemistry. 62: 417-421.

Amico V. y Biondi D. 1990. Citado en: Kozubek A. y Tyman J. 1999. Resorcinolic lipids, the natural non-isoprenoid phenolic amphiphiles and their biologycal activity. Chemical Reviews. 99: 1-31.

Anderson H., David N. y Leake C. 1931. Oral toxicity of certain alkylresorcinols in guinea pigs and rabbits. Proc. Soc. Exp. Biol. Med. 28: 609-612. En: Zarnowski R., Suzuki Y.,Yamaguichi I. y Stanislaw P. 2002. Alkylresorcinols in Barley (Hordeumvulgare L. distichon) Grains. Zeitschrift für Naturforschung. 57c: 57-62.

Asahina Y. y Yasue M. 1937. Citado en: Kozubek A. y Tyman J. 1999. Resorcinolic lipids, the natural non-isoprenoid phenolic amphiphiles and their biologycal activity.Chemical Reviews. 99: 1-31.

Avsejs L., Nott C., Xie S., Maddy D., Chambers F. y Evershed R. 2002. 5-n-Alkylresorcinols as biomarkers of sedges in anombrotrophic peat section. Organic Geochemistry. 33: 861–867.

Barakat K., Gajewski M. y Tuszynski J. 2012. DNA polymerase beta (pol b) inhibitors: A comprehensive overview. Drug Discovery Today. 17: 913-920.

Barrow R. y Capon R. 1991. Alkyl and alkenyl resorcinols from an Australian marinesponge, Haliclona sp. (Haplosclerida: Haliclonidae). Australian Journal of Chemistry. 44: 1393-1405.

Bitkov V., Nenashev V., Pridachina N. y Batrakov S. 1992. Membrane-structuring properties of bacterial long-chain alkylresorcinols. Biochimica et Biophysica Acta (BBA)–Biomembranes. 1108: 224-232.

Briggs D.1974. Citado en: Ross A., Åman P., Andersson R. y Kamal-Eldin A. 2004. Chromatographic analysis of alkylresorcinols and their metabolites. Journal of Chromatography. 1054: 157-164.

Cazorla F., Duckett S., Bergström E., Noreen S., Odijk R., Lugtenberg B., Thomas-Oates J. y Bloemberg G. 2006. Biocontrol of Avocado Dematophora Root Rot by Antagonistic Pseudomonas fluorescens PCL1606 correlates with the Production of 2-Hexyl 5-Propyl Resorcinol. Molecular Plant-Microbe Interactions Journal. 19: 418-428.

Chang H., Lin Y., Lee S., Yang C., Lin W., Tsai I. y Chen I. 2009. Cytotoxic alkyl benzoquinones and alkyl phenols from Ardisia virens. Phytochemistry. 70: 2064-2071.

Chopra T. y Gokhale R. 2009. Polyketide versatility in the biosynthesis of complex mycobacterial cell wall lipids. Methods in Enzymology. 459: 259-294.

Ciesik K., Koll A. y Grdadolnik J. 2006. Structural characterization of phenolic lipid and its derivative using vibrational spectroscopy. Vibrational Spectroscopy. 41: 14-20.

Diogenes M., DeMorais S., Ferreira F. 1996. Citado en: Ji X. y Jetter R. 2008. Very long chain

alkylresorcinols accumulate in the intracuticular wax of rye (Secale cereale L.) leaves near the tissue surface. Phytochemistry. 69: 1197–1207.

Droby S. y Prusky D. 1987. Citado en: Ji X. y Jetter R. 2008. Very long chain alkylresorcinols accumulate in the intracuticular wax of rye (Secale cereale L.) leaves near the tissue surface. Phytochemistry. 69: 1197–1207.

Evans L., Dedio W., y Hill R. 1973. Variability in the alkylresorcinol content of rye grains. Canadian Journal of plant science. 53: 485-488.

Gajda A., Kulawinek M. y Kozubek A. 2008. An improved colorimetric method for the determination of alkylresorcinols in cereals and whole-grain cereal products. Journal of Food Composition and Analysis. 21: 428– 434.

Garcia S., García C., Heinzen H., Moyna P. 1997. Citado por: Zarnowski R., Kozubek A. y Pietr S. 1999. Effect of rye 5-n-alkylresorcinols on in vitro growth of phytopathogenic Fusarium and Rhizoctonia fungi. Bulletin of the Polish Academy of Sciences. 47: 231-235.

Gembeh S., Brown R., Grimm C. y Cleveland T. 2001. Identification of chemical components of corn kernel pericarp wax associated with resistance to Aspergillus flavus infection and aflatoxin production. Journal of Agricultural and Food Chemistry. 49: 4635–4641.

Gliwa J., Gunenc A., Ames N., Willmore w. y Hosseinian F. 2011. Antioxidant activity of alkylresorcinols from rye bran and their protective effects

on cell viability of PC-12 AC cells. Journal of Agricultural and Food Chemistry. 59: 11473–11482.

Goyal A., Saxena P., Rahman A., Singh P., Kasbekar D., Gokhale R. y Sankaranarayanan R. 2008. Structural insights into biosynthesis of resorcinolic lipids by a type III polyketide synthase in Neurospora crassa. Journal of Structural Biology. 162: 411–421.

Gasiorowski K., Szyba K., Brokos B. y Kozubek A. 1996. Antimutagenic activity of alkylresorcinols from cereal grains. Cancer Letters. 106: 109-115.

Gubernator J., Stasiuk M. y Kozubek A. 1999. Dual effect of alkylresorcinols, natural amphiphilic compounds, upon liposomal permeability. Biochimica et Biophysica Acta. 1418: 253–260.

Gunenc A., HadiNezhad M., Tamburic-Ilincic L., Mayer P. y Hosseinian F. 2013. Effects of region and cultivar on alkylresorcinols content and composition in wheat bran and their antioxidant activity. Journal of Cereal Science. 57: 405–410

Hassan M.K., Dann E.K., Irving D.E., Coates, L.M. 2007. Concentrations of constitutive alk(en)ylresorcinols in peel of commercial mango varieties and resistance to postharvest anthracnose. Physiological and Molecular Plant Pathology. 71:158-165

Hengtrakul P., Lorenz K. y Mathias M. 1990. Alkylresorcinols in U.S. and Canadian Wheats and Flours. Cereal Chemistry. 67 (5): 413-417.

Hoffmann F. y Wenzel G. 1981. Self-compatibility in Microspore-derived Double-haploid Rye lines

and Single Grain selection for Alkylresorcinol content. Theoric applied Genetics. 60: 129-133.

Ji X. y Jetter R. 2008. Very long chain alkylresorcinols accumulate in the intracuticularwax of rye (Secale cereale L.) leaves near the tissue surface. Phytochemistry. 69: 1197–1207.

Jin W. y Zjawiony J. 2006. 5-Alkylresorcinols from Merulius incarnatus. Journal of Natural products. 69: 704-706.

Kieleczawa J., Szalewicz A., Kozubek A. y Kulig E. 1987. Citado en: Zarnowski R., Suzuki Y., Yamaguichi I. y Stanislaw P. 2002. Alkylresorcinols in Barley (Hordeum vulgare L. distichon) Grains. Zeitschrift für Naturforschung. 50 -57.

Keyes W.J., O'Malley R.C., Kim D., Lynn D.G. 2000. Signaling organogenesis in parasitic angiosperms: xenognosin generation, perception, and response. Journal of Plant Growth Regulation, 19:217-231.

Korycinska M., Czelna K., Jaromin A. y Kozubek A. 2009. Antioxidant activity of rye bran alkylresorcinols and extracts from whole-grain cereal products. Food Chemistry. 116: 1013–1018.

Kozubek A. y Demel R. 1980. Citado en: Siwko M., de Vries A., Mark a., Kozubek A. y Marrink S. 2009. Disturb or Stabilize? A Molecular Dynamics Study of the Effects of Resorcinolic Lipids on Phospholipid Bilayers. Biophysical Journal 96: 3140–3153.

Kozubek A. y Tyman J. 1999. Resorcinolic lipids, the natural non-isoprenoid phenolic amphiphiles and their biologycal activity. Chemical Reviews. 99: 1-31.

Kozubek A. 1984. Citado en: Ross A., Åman P., Andersson R. y Kamal-Eldin A. 2004. Chromatogra-phic analysis of alkylresorcinols and their metabolites. Journal of Chromatography. 1054: 157 – 164.

Kozubek A. 1985. Citado en: Siwko M., de Vries A., Mark a., Kozubek A. y Marrink S. 2009. Disturb or Stabilize? A Molecular Dynamics Study of the Effects of Resorcinolic Lipids on Phospholipid Bilayers. Biophysical Journal 96: 3140–3153.

Kozubek A., Pietr S. y Czerwonka A. 1996. Alkylresorcinols Are Abundant Lipid Components in Different Strains of Azotobacter chroococcum and Pseudomonas spp. Journal of Bacteriology. 178: 4027-4030.

Kulawinek M. y Kozubek A. 2008. Quantitative determination of alkylresorcinols in cereal grains: independence of the length of the aliphatic side chain. Journal of Food Lipids. 15: 251–262.

Liu L., Winter K., Stevenson L., Morris C. y Leach D. 2012. Wheat bran lipophilic compounds with in vitro anticancer effects. Food Chemistry. 130: 156–164.

Lytollis W., Scannell R., Murty H., Sambi K., Barr J. y Hecht S. 1995. 5-Alkylresorcinols from Hakea trifurcate that cleave DNA. Journal of American Chemical society. 117: 12683-12690.

Magnucka E., Suzuki Y., Pietr S., Kozubek A. y Zarnowski R. 2007. Action of benzimidazole fungicides on resorcinolic lipid metabolism in rye seedlings depends on thermal and light growth conditions. Pesticide Biochemistry and Physiology. 88: 219–225.

Masaki M., Hiro S., Usuki Y., Harumoto T., Terazima M., Buonanno F., Miyake A. y Iio H. 2004. Climacostol, a defense toxin of Climacostomum virens (protozoa, ciliata), and its congeners. Tetrahedron. 60: 7041–7048.

Metzger P. y Largeau C. 1994. A new type of ether lipid comprising phenolic moieties in Botryococcus braunii. Chemical structure and abundance, and geochemical implications. Organic Geochemistry. 22: 801-814.

Metzger P. 1994. Phenolic ether lipids with an n-alkenylresorcinol moiety from a bolivian strain of Botryococcus braunii (A race). Phytochemistry. 36: 195-212.

Musehold J. 1974. Methods of selection of rye plants low in 5-n-alkylresorcinol. Zeitschrift für Pflanzenzüchtung. 71: 124-129.

Chaturvedula VS, Schilling JK, Miller JS, Andriantsiferana R, Rasamison VE, Kingston DG. D. 2002. New cytotoxic bis-5-alkylresorcinol derivatives from the leaves of Oncostemon bojerianumfrom the Madagascar rainforest. Journal of Natural Products. 65: 1627–1632.

Przeworska E., Gubernator J. y Kozubek A. 2001. Formation of liposomes by resorcinolic lipids, single-chain phenolic amphiphiles from Anacardium occidentale L. Biochimica et Biophysica Acta. 1513: 75-81.

Reiss J. 1989. Citado por: Zarnowski R., Kozubek A. y Pietr S. 1999. Effect of rye 5-n-alkylresorcinols on in vitro growth of phytopathogenic Fusarium and Rhizoctonia fungi. Bulletin of the polish academy of sciences. 47: 231-235.

Rejman J. y Kozubek A. 2004. The Effect of Alkylresorcinol on Lipid Metabolism in Azotobacter chroococcum. Zeitschrift für Naturforschung. 59c: 393-398.

Ross A., Åman P., Andersson R. y Kamal-Eldin A. 2004a. Chromatographic analysis of alkyl-resorcinols and their metabolites. Journal of Chromatography A. 1054: 157-164.

Ross A., Åman P. y Kamal-Eldin A. 2004b. Identification of cereal alkylresorcinol metabolites in human urine potential biomarkers of whole grain wheat and rye intake. Chromatography B Analytical Technology Biomedical Life Science. 809: 125–130.

Sampietro D., Vattuone M. y Catalán C. 2008. A new colorimetric method for determination of alkylresorcinols in ground and whole-cereal grains using the diazonium salt Fast Blue RR. Food Chemistry. 115: 1170–1174.

Stasiuk M. y Kozubek A. 2010. Biological activity of phenolic lipids. Cellular and Molecular Life Sciences. 67: 841-860.

Stasiuk M., Bartosiewicz D., Gubernator J., Cieslik-Boczula K., Hof M. y Kozubek A. 2007. A semisynthetic 5-n-alkylresorcinolderivative and its effect upon biomembrane properties. Zeitschrift für Naturforschung. 62c: 881-888.

Stasiuk M., Jaromin A. y Kozubek A. 2004. The effect of merulinic acid on biomembranes. Bio-chimica et Biophysica Acta. 1667: 215 – 221.

Stodola F., Weisleder D. y Vesonder R. 1973. Citado en: Kozubek A. y Tyman J. 1999. Resorcinolic lipids, the natural non-isoprenoid

phenolic amphiphiles and their biologycal activity. Chemical Reviews. 99: 1-31.

Tluscik F., Kozubek A. y Mejbaum-Katzenellenbogen W. 1981. Citado en: Sampietro D., Vattuone M. y Catalán C. 2009. A new colorimetric method for determination of alkylresorcinols in ground and whole-cereal grains using the diazonium salt Fast Blue RR. Food Chemistry. 115: 1170-1174.

Verdeal K. y Lorenz K. 1977. Alkylresorcinols in wheat, rye and triticale. Cereal chemistry. 54: 475-483.

Wasserman D. y Dawson R. 1948. Citado en: Zarnowski R., Suzuki Y., Yamaguichi I. y Stanislaw P. 2002. Alkylresorcinols in Barley (Hordeum vulgare L. distichon) Grains. Zeitschrift für Naturforschung. 57c: 57-62.

Wieringa G. 1967. On the Occurrence of Growth Inhibiting Stubtances in Rye. Veenman H. Wageningen. The Netherlands. En: Kozubek A. y Tyman J.1999. Resorcinolic lipids, the natural non-isoprenoid phenolic amphiphiles and their biologycal activity. Chemical Reviews. 99: 1-31.

Yamashita Y., Matsunami K., Otsuka H., Shinzato T. y Takeda Y. 2008. Grevillosides A–F: Glucosides of 5-alkylresorcinol derivatives from leaves of Grevillea robusta. Phytochemistry. 69: 2749–2752

Yang S., Chan T., Terracciano J., Loebenberg D., Patel M., Gullo V. y Chu M. 2006. A New 5-Alkenylresorcinol Sch 725681 from Aspergillus sp. Journal of Antibiotics. 59: 190-192.

Zarnowska E., Zarnowski R. y Kozubek A. 2000. Alkylresorcinols in Fruit Pulp and Leaves of Ginkgo biloba L. Zeitschrift für Naturforschung C. 55c: 881-885.

Zarnowski R., Kozubek A. y Pietr S. 1999. Effect of rye 5-n-alkylresorcinols on in vitro growth of phytopathogenic Fusarium and Rhizoctonia fungi. Bulletin of the Polish Academy of Sciences. 47: 231-235.

Zarnowski R., Lewicka T. y Pietr S. 2000a. Production and secretion of 5-n-alkylresorcinols by Fusarium culmorum. Zeitschrift für Naturforschung C. 55c: 846-848.

Zarnowski R., Suzuki Y., Esumi I. yPietr S. 2000b. 5-n- Alkylresorcinols from the green microalga Apatococcus constipates. Phytochemistry. 55: 975-977.

Zarnowski R., Suzuki Y., Yamaguch I. y Pietr S. 2002. Alkylresorcinols in Barley (Hordeum vulgare L. distichon) Grains. Zeitschrift für Naturforschung C. 57c: 57-62.

Zarnowski R., Suzuki Y., Zarnowska E., Esumi Y., Kozubek A. y Pietr S. 2004. 5-n-Alkylresorcinols from the Nitrogen-fixing Soil Bacterium Azotobacter chroococcum Az12. Zeitschrift für Naturforschung C. 59: 318-320.

Zhu Y., Conklin D., Chen H., Wang L., Sang S. 2011. 5-Alk(en)ylresorcinols as the major active components in wheat bran inhibit human colon cancer cell growth. Bioorganic and Medicinal Chemistry. 19: 3973–3982.

Cómo citar
Suaza-García, E. R., & Coy-Barrera, E. (2014). Alquilresorcinoles: Compuestos Naturales con Importancia Biológica. Revista Facultad De Ciencias Básicas, 10(2), 210–222. https://doi.org/10.18359/rfcb.332
Publicado
2014-12-10
Sección
Artículos

Métricas

QR Code