Abstract
Metopium brownei is a tree that grows in coastal tropical forests along the Gulf of Mexico and in the Yucatan Peninsula. This medicinal species produces a strongly irritant exudate, and sometimes forms pure populations favored by fire. The bioactivity of the aqueous leachates, organic extracts (leaves, bark, and wood), and mixtures of urushiols and flavonoids from M. brownei were evaluated on the growth of two plants: Amaranthus hypochondriacus and Echinochloa crusgalli, and four phytopathogenic fungi: Fusarium oxysporum, Helminthosporium sp., Alternaria sp., and Pythium sp. Alkylcatechols (urushiols) were isolated from an acetone extract of the bark. Dihydroquercetin and eriodictyol were isolated from the chloroform–methanol extract of the wood. In addition, masticadienoic acid was isolated from the leaves. The aqueous leachates, organic extracts, and the mixtures of flavonoids and urushiols were inhibitory to the growth of test plants and phytopathogenic fungi. The allelochemical role of the bioactive compounds from M. brownei is discussed in relation with other results reported in some studies on Anacardiaceae family and M. brownei.
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REFERENCES
Amo, S. del. 1979. Plantas Medicinales del Estado de Veracruz. Instituto Nacional de Investigaciones sobre Recursos Bióticos (INIREB), Xalapa, México.
Anaya, A. L., and Rovalo, M. 1976. Alelopatía en plantas superiores: Diferencias entre el efecto de la presión osmótica y los alelopáticos sobre la germinación y el creimiento de algunas especies de la vegetación secundaria de una zona cálido-húmeda de México, pp. 388–427, in A. Gómez Pompa, C. Vázquez, S. del Amo, and A. Butanda (eds.). Investigaciones sobre la Regeneración de Selvas en Veracruz, México. Compañía Editorial Continental, S.A. México.
Anaya, A. L., Calera, M. R., Mata, R., and Pereda-Miranda, R. 1990. Allelopathic potential of compounds isolated from Ipomoea tricolor Cav. (Convolvulaceae). J. Chem. Ecol. 16:2145–2152.
Anderson, J. E., Goetz, C. M., MacLaughlin, J., and Suffness, M. 1991. A blind comparison of simple bench-top bioassays and human tumor cell cytoxicities as tumor prescreens. Phytochem. Anal. 2:107–111.
Bancroft, G. T., and Bowman, R. 1994. Temporal patterns in diet of nestling white-crowned pigeons: Implications for conservation of frugivorous columbids. Auk 111:844–852.
Brown, R. J., Kupper, J. L., Hixson, W. C., Bowman, J., and Baker, R. O. 1973. Animal disease survey on Navassa Island, West Indies. US National Technical Information Service. AD Rep. 767964/OGA.
Cabrera-Cano, E., Sousa-Sanchez, M., and Tellez-Valdes, O. 1982. Imágenes de la Flora Quintanarroense. Centro de Investigaciones de Quintana Roo e Instituto de Biología de la UNAM. México.
CastaÑeda, P., GarcÍa, M. R., HernÁndez-Bautista, B. E., Toress, B. A., Anaya, A. L., and Mata, R. 1992. Effects of some compounds isolated from Celaenodendron mexicanum Standl (Euphorboaceae) on seeds and phytopathogenic fungi. J. Chem. Ecol. 7:1025–1037.
Chakrabarty, D. K., and Ghosal, S. 1985. Effect of Fusarium moniliforme var. subglutinans infection on mangiferin production in the twigs of Mangifera indica. Phytopath. Z. 113:47–50.
Coley, P. D., and Barone, J. A. 1996. Herbivory and plant defenses in tropical forests. Annu. Rev. Ecol. Syst. 27:305–335.
Droby, S., Prusky, D., and Jacoby, B. 1985. Possible involvement of an antifungal compound in latent infection of the fungus Alternaria alternata in unripe mango fruits. Phytoparasitology 13:159.
Droby, S., Prusky, D., Jacoby, B., and Goodman, A. 1986. Resorcinol 5-heptodecenyl, an antifungal compound possibly involved in the latency of Alternaria alternata in unripe mango fruits. Phytopathology 75:1302.
Duke, J. A. 1985. Handbook of Medicinal Herbs. CRC Press, Boca Raton, Florida.
Fernandez, C., Fiandor, A., Martinez-Garate, A., and Quesada, J. M. 1995. Allery to pistachio: Crossreactivity between pistachio nut and other Anacardiaceae. Clin. Exp. Allergy 25(12):1254–1259.
Furth, D. G., and Young, D. A. 1988. Relationships of herbivore feeding and plant flavonoids (Coleoptera: Chrysomelidae and Anacardiaceae: Rhus). Oecologia 74:496–500.
Geller, M. 1989. Poison ivy, mangoes, cashews, and dermatitis. Ann. Intern. Med. 110:1036–1037.
GÓmez-Pompa, A., Whitmore, T. C., and Hadley, M. (eds.). 1991. Rain Forest Regeneration and Management. Man and the Biosphere Series, Vol. 6, The Parthenon Publishing Group, Park Ridge, New Jersey.
Gonzalez-Gaona, O. J., and Lagunes-Tejeda, A. 1986. Evaluation of synthetic and nonsynthetic methods for combating Spodoptera frugiperda and Sitophilus zeamais in La Chontalpa, Tabasco, Mexico. Folia Entomol. Mex. 70:65–74.
Gorst-Allman, C. P., Steyn, P. S., Heyl, T., Wells, M. J., and Fourie, D. M. C. 1987. Plant dermatitis: Isolation and chemical investigation of the major vesicant principle of Smodingium argutum. S. Afr. J. Chem. S. Afr. Tydskr. Chem. 40(1):82–86.
Gross, M., Baer, H., and Fales, H. M. 1975. Urushiols of poisonous Anacardiaceae. Phytochemistry 14:2263–2266.
Hamburger, M. O., and Cordell, G. A. 1978. A direct bioautographic TLC assay for compounds possessing antibacterial activity. J. Nat. Prod. 50:19–22.
Harborne, J. B. 1991. The chemical basis of plant defense, pp. 45–59, in R. T. Palo and C. T. Robbins (eds.). Plant Defenses Against Mammalian Herbivory. CRC Press, Boca Raton, Florida.
Harborne, J. B., and Baxter, H. (eds.). 1993. Phytochemical Dictionary. Taylor & Francis, London.
Marques, M. R., Albuquer, L. M., and Xavier, J. 1992. Antimicrobial and insecticidal activities of cashew tree gum exudate. Ann. AP Biol. 12:371–377.
Marques-Souza, A. C., Absy, M. L., Kerr, W. E., and Aguilera-Peralta, F. J. 1995. Polen coletado por duas especies de meliponineos (Hymenoptera: Apidae) da Amazonia. Rev. Bras. Biol. 55:855–864.
Martinez, M. 1979. Catálogo de Nombres Vulgares y Científicos de Plantas Mexicanas. Fondo de Cultura Económica, México.
McCutcheon, A. R., Ellis, S. M., Hancock, R. E. W., and Towers, G. H. N. 1994. Antifungal screening of medicinal plants of British Columbian native peoples. J. Ethnopharmacol. 44:157–169.
Mendieta, R. M., and Amo, S. del. 1981. Plantas Medicinales del Estado de Yucatán. Instituto Nacional de Investigaciones sobre Recursos Bióticos. Xalapa, Veracruz. Compañía Editorial Continental, S.A. de C.V., México.
Navarrete, A. 1986. Estudio químico de plantas mexicanas usadas en medicina tradicional. Constituyentes bioactivos de Chenopodium graveolens, Chenopodium ambrosioides y Amphipterygium adstringens. Tesis de Maestría. Facultad de Química, UNAM.
Qin, M. F., Mitchell, J. D., and Vogl, O. 1996. Oriental lacquer. 10. The South East Asian lacquer. J. Macromol. Sci. Pure Appl. Chem. 33:1791–1803.
Ramamoorthy, T. P., Bye, R., Lot, A., and Fa, J. 1993. Biological Diversity of Mexico: Origins and Distribution. Oxford University Press, New York.
Reyes-Chilpa, R., Perez-Morales, V., and del Angel Blanco, S. 1987. Influencia de los extractivos en la resistencia natural de seis maderas tropicales al hongo de pudrición morena Lenzites trabea. Biotica (Mexico) 12:7–19.
Rivero-Cruz, J. F., Chavez, D., Hernandez-Bautista, B. E., Anaya, A. L., and Mata, R. 1997. Separation and characterization of Metopium brownei urushiol components. Phytochemistry 45:1003–1008.
Rzedowsky, J. 1978. Vegetación de México. Editorial Limusa, S.A. México.
Shen, C.-C., and Chang, Y.-S. 1993. Nuclear magnetic resonance studies of 5,7-dihydroxy-flavonoids. Phytochemistry 34:843–845.
Smith, I. K., and Vankat, J. L. 1992. Dry evergreen forest (Coppice) communities of North Andros Island, Bahamas. Bull. Torrey Bot. Club 119:181–191.
Villanueva, G. R. 1994. Nectar sources of European and Africanized honey bee (Apis mellifera L.) in the Yucatan Peninsula, Mexico. J. Apicult. Res. 33:44–58.
Vogl, O., and Mitchell, J. D. 1996. Oriental lacquer. 11. Botany and chemistry of the active components of poisonous Anacardiaceae. J. Macromol. Sci. Pure Appl. Chem. 33:1581–1599.
Vogl, O., Qin, M. F., and Mitchell, J. D. 1995. Oriental lacquers. 7. Botany and chemistry of Japanese lacquer and the beauty of the final art objects. Cellul. Chem. Technol. 29:273–286.
Wagner, H., Mohar-Chari, V., and Sonnenbichler, J. 1976. 13C-NMR-spektren natürlich vorkommen der flavonoide. Tetrahedron Lett. 21:1799–1802.
Wahlberg, J. E., and Lovell, C. R. 1996. Poison wood dermatitis in a future prime minister. Contact Dermatitis 34:363.
Watson, E. S., Murphy, J. C., Wirth, P. W., Eisohly, M. A., and Skierkowski, P. 1981. Immunological studies of poisonous Anacardiaceae: Production of tolerance in guinea pigs using 3-n-pentadecylcatechol-“modified” autologous blood cells. J. Pharmacol. Sci. 70(7):785–789.
Watson, E. S., Murphy, J. C., and El-Sohly, M. A. 1983. Immunologic studies of poisonous Anacardiaceae: Oral desensitization to poison ivy and oak urushiols in guinea pigs. J. Invest. Dermatol. 80:149–155.
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Anaya, A.L., Mata, R., Rivero-Cruz, F. et al. Allelochemical Potential of Metopium brownei . J Chem Ecol 25, 141–156 (1999). https://doi.org/10.1023/A:1020845318284
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DOI: https://doi.org/10.1023/A:1020845318284