Toxic Phenols in Various Anacardiaceae Species

Economic Botany

Volumn 57, Issue 3, 2003, Pages 354-364

  Aguilar Ortigoza, Carlos J ^a,b   Sosa, Victoria ^a   Aguilar Ortigoza, Marcial ^c  

^a INSTITUTO DE ECOLOGÍA   (Mexico)

^b UNIVERSIDAD AUTÓNOMA DEL ESTADO DE MÉXICO   (Mexico)

^c INSTITUTO MEXICANO DEL SEGURO SOCIAL   (Mexico)

Author keywords

Anacardiaceae; Biflavonoid; Catechol; Dermatitis; Phenols; Resorcinol; Toxic allergens; Urushiol

Indexed keywords

ANACARDIACEAE; SPONDIAS;

EID: 0242287084     PISSN: 00130001     EISSN: None     Source Type: Journal    
DOI: 10.1663/0013-0001(2003)057[0354:TPIVAS]2.0.CO;2     Document Type: Article

References (73)

1. Adawadkar, P. D., and M. A. ElSohly. 1983. An urushiol derivative from poison sumac. Phytochemistry 22:1280-1281.
2. Aguilar C., A., and C. Zolla. 1982. Rhus radicans. Pages 180-181 in A. Aguilar C and C. Zolla, eds. Plantas tóxicas de México. Instituto Mexicano del Seguro Social, México, D.F., Mexico.
3. Backer, H. J., and N. H. Haack. 1938. Le principle toxique des fruits de Renghas (Semecarpus heterophylla Bl.). Recueil des Travaux Chimiques des Pays-Bas 57:225-232.
4. _. 1941. Le principle toxique du Gluta renghas Linn. Recueil des Travaux Chimiques des Pays-Bas 60:656-660.
5. Baer, H. 1979. The poisonous Anacardiaceae. Pages 161-170 in A. D. Kinghorn, ed., Toxic plants. Columbia University Press, New York, NY.
6. Baer, H., R. C. Watkins, A. P. Kurtz, J. S. Byck, and C. R. Dawson. 1967. Delayed contact sensitivity to catechols II. Cutaneous toxicity of catechols chemically related to the active principles of poison ivy. Journal of Immunology 99:365-369.
7. _, M. Hooton, H. Fales, A. Wu, and F. Schaub. 1980. Catecholic and other constituents of the leaves of Toxicodendron radicans and variation of urushiol concentrations within one plant. Phytochemistry 19:799-802.
8. Bate-Smith, E. C. 1962. The phenolic constituents of plants and their taxonomic significance. I. Dicotyledons. Journal of the Linnean Society (Botany) 58: 95-173.
9. Bestman, H., B. Classen, U. Kobold, O. Vostrowsky, F. Klingauf, and U. Stein. 1988. Steam volatile constituents from leaves of Rhus typhina. Phytochemistry 27:85-90.
10. Carpenter, R. C., S. Sotheeswaran, M. U. Sultanbawa, and S. Balasubramaniam. 1980. (-)-5-methylmellein and catechol derivatives from four Semecarpus species. Phytochemistry 19:445-447.
11. Chen, F. A., Y. M. Lin, and C. M. Liang. 1974. Biflavonyls from drupes of Rhus succedanea. Phytochemistry 12:276-278.
12. Cojocaru, M., S. Droby, E. Glotter, A. Goldman, H. E. Gottlieb, B. Jacoby, and D. Prusky. 1986. 5-(12-Heptadecenyl)-resorcinol, the major component of the antifungal activity in the peel of mango fruit. Phytochemistry 25:1093-1095.
13. Corbett, M., and S. Billets. 1975. Characterization of poison oak urushiol. Journal of Pharmaceutical Sciences 64:1715-1718.
14. Corthout, J., J. Jaanssens, L. Pieters, D. Vandenberghe, and A. J. Vlietninck. 1989. The isolation of a long chain phenol from Spondias mombin. Planta Medica 55:112-113.
15. _, L. Pieters, M. Claeys, D. Vandenberghe, and A. Vlietinck. 1992. Antiviral caffeoyl esters from Spondias mombin. Phytochemistry 31:1979-1981.
16. _, L. Pieters, M. Claeys, S. Geerts, D. Vandenberghe, and A. Vlietinck. 1994. Antibacterial and molluscicidal phenolic acids from Spondias mombin. Planta Medica 60:460-463.
17. Di Lullo, O. 1934. "El Paaj" une nouvelle dermatite vénéneuse. Revue Sud-American Médicine 5:513.
18. Du, Y., R. Oshima, and J. Kumanotani. 1984. Reversed-phase liquid Chromatographic separation and identification of constituents of urushiol in the sap of the lac tree, Rhus vernicifera. Journal of Chromatography 284:463-467.
19. Dunn, I. S., D. J. Liberato, N. Castognoli, and V. S. Byers. 1986. Influence of chemical reactivity of urushiol-type haptens on sensitization and induction of tolerance. Cellular Immunology 97:189-196.
20. Edwards, E. K. Jr., and E. K. Edwards Sr. 1995. Spontaneous repigmentation of vitiligo following generalized acute allergic contact dermatitis. Contact Dermatitis 33:123-141.
21. Eggers, S. H. 1974. Vesicant principles of Smodingium argutum (Anacardiaceae). Journal of South Africa Chemical Institute 27:99-104.
22. Engler, A. 1883. Anacardiaceae. Pages 171-546 in A. P. & A. C. De Candolle, eds., Monographie Phanerogamarum Vol. 4. G. Masson, Paris, France.
23. Evans, F. J., and R. J. Schmidt. 1980. Plants and plant products that induce contact dermatitis. Planta Medica 38:289-316.
24. Findlay, G. H., D. A. Whiting, S. H. Eggers, and R. P. Ellis. 1974. Smodingium (African poison ivy) dermatitis: history, comparative plant chemistry and anatomy, clinical and histological features. British Journal of Dermatology 90:535-541.
25. Funes, E., J. M. Milán, J. A. Pagán, J. D. López, F. J. García, J. M. Negro, J. Hernández, F. Polo, and P. Rico. 1999. Allergy to Anarcadiaceae. Identification of allergens. Alergología e Inmunología Clínica 14:82-89.
26. Gadek, P. A., E. S. Fernando, C. J. Quinn, S. Hoot, T. Terrazas, M. Sheahan, and M. W. Chase. 1996. Sapindales: molecular delimitation and infraordinal groups. American Journal of Botany 83: 802-811.
27. Gambaro, V., M. C. Chamy, E. von Brand, and J. A. Gambarino. 1986. 3-(pentadec-10-enyl)-catechol, a new allergenic compound from Lithraea caustica (Anacardiaceae). Planta Medica 44:20-22.
28. Gedam, P. H., P. S. Sampathkumaran, and M. A. Sivasamban. 1974. Composition of bhilawanol from Semecarpus anacardium. Phytochemistry 13: 513-515.
29. Gross, M., H. Baer, and H. M. Fales. 1975. Urushiols of poisonous Anacardiaceae. Phytochemistry 14:2263-2266.
30. Halim, H., H. D. Locksley, and J. J. Memon. 1980. Vesicant principles of poison ivy and related plants: synthesis of the urushiols, 1,2-dihydroxy-3-((Z)- pentadec-8-enyl)benzene and 1,2-dihydroxy-3-pen-tadecylbenzene. Journal of the Chemical Society, Perkin Transactions 1:2331-2337.
31. Harborne, J. B. 2000. Arsenal for survival: secondary plant products. Taxon 49:435-449.
32. _. 1973. Phenolic compounds. Pages 33-88 in J. B. Harborne, Phytochemical methods. Chapman and Hall, London.
33. _. 1989. General procedures and measurement of total phenolics. Pages 10-11 in J. B. Harborne, ed., Methods in plant biochemistry. Vol. I. Academic Press, London, England.
34. _. 1999. Classes and function of secondary products from plants. Pages 17-19 in N. J. Walton and D. E. Brown, eds., Chemicals from plants. Imperial College Press, London, England.
35. Hersch-Martínez, P. 1995. Commercialization of wild medicinal plants from southwest Puebla, Mexico. Economic Botany 49:197-206.
36. Hill, G. A., V. Mattacotti, and W. D. Graham. 1934. The toxic principle of the poison ivy. Journal of the American Chemical Society 56:2736-2738.
37. Joel, D. M. 1980. Resin ducts in the mango fruit: a defense system. Journal of Experimental Botany 31:1707-1718.
38. Johnson, R. A., H. Baer, C. H. Kirkpatrick, C. R. Dawson, and R. G. Khurana. 1972. Comparison of the contact allergenicity of the four pentadecyl-catechols derived from poison ivy urushiol in human subjects. Journal of Allergy and Clinical Immunology 49:27-35.
39. Lamberton, J. A. 1959a. Studies on the optically active compounds of Anacardiaceae exudates. V. Further investigation of the exudate from Campnosperma auriculata Hook. f. Australian Journal of Chemistry 12:224-233.
40. _. 1959b. Studies on the optically active compounds of Anacardiaceae exudates. VI. The exudate from Pentaspadon officinalis Holmes. Australian Journal of Chemistry 12:234-239.
41. Lloyd, H. A., C. Denny, and G. Krishna. 1980. A simple liquid chromatographic method for analysis and isolation of the unsaturated components of anacardic acid. Journal of Liquid Chromatography 3: 1497-1504.
42. Majima, R. 1922a. Über den Hauptbestandteil des Japan-Lacks, VIII. Mitteilung: Stellung der Doppelbindungen in der Seitenkette des Urushiols und Beweisführung, das Urushiol eine Mischung ist. Berichte der Deutschen Chemischen Gesellschaft 55, Abteilung B(1):172-191.
43. _. 1922b. Über den Hauptbestandteil des Japan-Lacks, IX. Mitteilung: Chemische Untersuchung der verschiedenen natürlichen Lackarten, die dem Japan-Lack nahe verwandt sind. Berichte der Deutschen Chemischen Gesellschaft 55, Abteilung B(1):191-214.
44. Mata, R., F. Calzada, A. Navarette, F. del Rio, and G. Delgado. 1991. Long-chain phenols from the bark of Amphypterygium adstringens. Journal of Ethnopharmacology 34:147-154.
45. Mitchell, J. D. 1990. The poisonous Anacardiaceae genera of the world. Advances in Economic Botany 8:103-129.
46. Mitchell, J. D., and A. Rook. 1979. Botanical dermatology: plants and plant products injurious to the skin. Greengrass Ltd., Vancouver, British Columbia, Canada.
47. Morton, J. F. 1978. Brazilian pepper - its impact on people, animals and the environment. Economic Botany 32:353-359.
48. _. 1981. Anacardiaceae. Pages 469-479 in J. F. Morton, ed. Atlas of medicinal plants of Middle America, Bahamas to Yucatan. Charles C. Thomas Publisher, Springfield, IL.
49. Nair, G. V., A. N. Poti, and P. P. Pillay. 1952a. The constituents of lacquer-bearing trees of Travancore-Cochin: Part I - chemical examination of the constituents of Holigarna arnottiana Hook. f. Journal of Scientific and Industrial Research IIB:294-297.
50. _. 1952b. The constituents of lacquer-bearing trees of Travancore-Cochin: Part II - chemical examination of the latex of Semecarpus travancorica Bed. Journal of Scientific and Industrial Research IIB:298-299.
51. Nakano, T., J. D. Medina, and I. Hurtado. 1970. The chemistry of Rhus striata ("Manzanillo"). Planta Medica 18(3):260-265.
52. Oelrichs, P. B., J. K. McLeod, A. A. Seawright, and J. C. Ng. 1997. Isolation and characterization of urushiol components from the Australian native cashew (Semecarpus australiensis). Natural Toxins 5:96-98.
53. Pell, S. K., and L. Urbatsch. 2001. Evaluation of evolutionary relationships in Anacardiaceae using matK sequence data. Botany 2001. Plants and People. August 12-16, Albuquerque, New Mexico. Abstract 142.
54. Puntambekar, S. V., and R. M. Beri. 1954. Resinol from the nuts of Semecarpus travancoricus. Proceedings of Indian Academy of Sciences 39:137-143. [Cited from Biological Abstracts. 28:29690].
55. Rao, N. S. P., L. R. Row, and R. T. Brown. 1973. Phenolic constituents of Semecarpus anacardium. Phytochemistry 12:671-681.
56. Ribéreau-Gayon, P. 1972. Plant phenolics. Hafner, New York, NY.
57. Rivero-Cruz, J. F., D. Chávez, B. Hernández, A. L. Anaya, and R. Mata. 1997. Separation and characterization of Metopium brownei urushiol components. Phytochemistry 45:1003-1008.
58. Rzedowski, J., and G. Calderón de Rzedowski. 1999. Anacardiaceae: flora del Bajío y regiones adyacente 28:1-50. Instituto de Ecología A.C., Pátzcuaro, Mexico.
59. Smith, P. M. 1976. The chemotaxonomy of plants. Edward Arnold, London, England.
60. Stahl, E., K. Keller, and C. Blinn. 1983. Cardanol, a skin irritant in Pink Pepper. Planta Medica 48:5-9.
61. Stampf, J. L., N. Castagnoli, and W. Epstein. 1990. Suppression of urushiol-induced delayed-type hypersensitivity responses in mice with serum IgG immunoglobulin from human hyposensitized donors. Journal of Investigative Dermatology 95:363-365.
62. Terrazas, T. 1994. Wood anatomy of the Anacardiaceae: ecological and phylogenetic interpretation. Ph.D. thesis, University of North Carolina, Chapel Hill, North Carolina.
63. _, and M. W. Chase. 1996. A phylogenetic analysis of Anacardiaceae based on morphology, anatomy and rbcL sequence data. American Journal of Botany 83:197-198. Suppl. (Abstracts).
64. Tyman, J. H., and L. J. Morris. 1967. The composition of cashew nut-shell liquid (CNSL) and the detection of a novel phenolic ingredient. Journal of Chromatography 27:287-288.
65. Wannan, B. S., and C. J. Quinn. 1988. Biflavonoids in the Julianaceae. Phytochemistry 27:31-62.
66. Wannan, B. S., and C. J. Quinn. 1990. Pericarp structure and generic affinities in the Anacardiaceae. Botanical Journal of the Linnean Society 102: 225-252.
67. _. 1991. Floral structure and evolution in Anacardiaceae. Botanical Journal of the Linnean Society 107:349-385.
68. Wannan, B. S., J. T. Waterhouse, P. A. Gadek, and C. J. Quinn. 1985. Biflavonyls and the affinities of Blepharocarya. Biochemical Systematics and Ecology 13:105-108.
69. Whalley, W. B. 1959. The toxicity of plant phenolics. Pages 27-37 in J. W. Fairbairn, ed., The pharmacology of plant phenolics. Academic Press, London, England.
70. Williams, C. A., and J. B. Harborne. 1989. Biflavonoids. Pages 357-387 in J. Harborne, ed., Methods in plant biochemistry. Vol. 1. Academic Press, London, England.
71. Yalpani, M., and J. H. P. Tyman. 1983. The phenolic acids of Pistacia vera. Phytochemistry 22:2263-2266.
72. Young, D. A. 1976. Heartwood flavonoids and the infrageneric relationships of Rhus (Anacardiaceae). American Journal of Botany 66:502-510.
73. _, and S. J. Aist. 1987. Biflavonoids and the taxonomy of the Anacardiaceae. American Journal of Botany 74:705. (Abstract).