Abstract
A negative correlation has been found between the amounts of pterosins A and B and ptaquiloside per biomass unit, and the growth stage of the blade of bracken. Their concentration decreased progressively from the crozierto the mature frond, where it attained less than 5% of the initial value. The growth was measured following the total blade length, its height, moisture content, and time of emergence from the soil surface. Quantitation of these compounds was achieved by HPLC using a water extraction, methylene chloride treatment, and silica gel microcolumn cleanup sequence. Pterosins were unevenly distributed in the blade, whereas ptaquiloside maintained a constant concentration throughout. Rhizomes contained only minor amounts of these compounds. Their possible role as semiochemicals in bracken is discussed.
Similar content being viewed by others
Explore related subjects
Discover the latest articles and news from researchers in related subjects, suggested using machine learning.References
Agnew, M.P., andLauren, D.R. 1991. Determination of ptaquiloside in bracken fern (Pteridium esculentum).J. Chromatogr. 538:462–468.
Baruch, Z., Hernández-R., A.B., andMontilla, M.G. 1989. Dinámica del crecimiento, fenología y repartición de biomasa en gramíneas nativas e inducidas en una sabana neotropical.Ecotropicos 2:1–13.
Cooper-Driver, G.A. 1976. Chemotaxonomy and phytochemical ecology of bracken.Bot. J. Linn. Soc. 73:35–46.
Cooper-Driver, G.A. 1990. Defense strategies in bracken,Pteridium aquilinum (L.) Kuhn.Ann. Mo. Bot. Gard. 77:281–286.
Cooper-Driver, G.A., andSwain, T. 1976. Cyanogenic polymorphism in bracken in relation to herbivore predation.Nature 26:604.
Evans, I.A. 1979. Bracken carcinogenicity.Res. Vet. Sci. 26:339–348.
Evans, W.C. 1986. The acute diseases caused by bracken in animals, pp. 121–132,in R.T. Smith and J.A. Taylor (eds.). Bracken, Ecology, Land Use and Control Technology. Parthenon Publishing, Carnforth, Lancashire, U.K.
Evans, W.C., Evans, E.T.R., andRoberts, H.E. 1951. Studies on bracken poisoning in the horse.Br. Vet. J. 107:364–371.
Evans, W.C., Evans, I.A., Humphreys, D.J., Lewin, B., Davies, W.E.J., andAxford, R.F.E. 1973. Induction of thiamine deficiency in sheep with lesions similar to those of cerebrocortical necrosis.J. Comp. Pathol. 85:253–267.
Feeny, P.P. 1976. Plant apparency and chemical defense.Recent Adv. Phytochem. 10:1–40.
Fenwick, G.R. 1988. Bracken (Pteridium aquilinum). Toxic effects and toxic constituents.J. Sci. Food Agric. 46:147–173.
Galpin, O., andWhitaker, C. Stomach Cancer and Bracken. Is there a connection? p. 52,in J.A. Taylor (ed.). Bracken Toxicity and Carcinogenicity as Related to Animal and Human Health. Special publication of International Bracken Group. Geography Department, University College of North Wales, Aberystwyth, Wales.
Harper, J.L. 1977. The Population Biology of Plants. Academic Press, London.
Hirono, I. 1986. Carcinogenic principles isolated from bracken fern.CRC Crit. Rev. Toxicol. 17:1–22.
Hirono, I., Aiso, S., Yamaji, T., Mori, H., Yamada, K., Niwa, H., Ojika, M., Wakamatsu, K., Kigoshi, H., Niiyama, K., andUosaki, Y. 1984a. Carcinogenicity in rats of ptaquiloside isolated from bracken.Gann 75:833–836.
Hirono, I., Aiso, S., Yamaji, T., Niwa, H., Ojika, M., Wakamatsu, K., andYamada, K. 1984b. Hyperplastic nodules of the liver induced in rats fed bracken diet.Cancer Lett. 22:151–155.
Hirono, I., Ogino, H., Fujimoto, M., Yamada, K., Yoshida, Y., Ikagawa, M., andOkumura, M. 1987. Induction of tumors in ACI rats given a diet containing ptaquiloside, a bracken carcinogen.J. Natl. Cancer Res. Inst. 79:1143–1149.
Jones, C.G. 1983. Phytochemical variation, colonization and insect communities: The case of bracken fernPteridium aquilinum), pp. 513–558,in R.F. Denno and M.S. McLure (eds.). Variable Plants and Herbivores in Natural and Managed Systems. Academic Press, New York.
Jones, C.G. andFirn, R.D. 1979. Resistance ofPteridium aquilinum to attack by non adapted phytophagous insects.Biochem. Syst. Ecol. 7:95–101.
Koyama, K., Takatsuki, S., andNatori, S. 1991. Dennstoside A, an analogue of ptaquiloside, fromDennstaedtia scahraPhytochem. 30:2080–2082.
LeRoy, M.L., andGoerlitz, D.F. 1970. Microcolumn chromatographic cleanup for the analysis of pesticides in water.J. A. O. A. C. 35:1276–1285.
Matoba, M., Saito, E., Saito, M.K., Koyama, K., Natori, S., Matsushima, T., andNakimoto, M. 1987. Assay of ptaquiloside, the carcinogenic principle of bracken,Pteridium aquilinum, by mutagenicity testing inSalmonella typhimurium.Mutagenesis 2:419–423.
McKey, D. 1979. The distribution of secondary compounds within plants, pp. 56–133,in G.A. Rosenthal and D.H. Janzen (eds.). Herbivores, Their Interaction with Secondary Plant Metabolites. Academic Press, New York.
Murakami, T., andSaiki, Y. 1989. Chemosystematics of di- and sesquiterpenoids in polypodiaceous ferns.Biochem. Syst. Ecol. 17:131–140.
Niwa, H., Ojika, M., Wakamatsu, K., Yamada, K., Hirono, I., andMatsushita, K. 1983. Ptaquiloside, a novel norsesquiterpene glucoside from bracken,Pteridium aquilinum var.Latiusculum. Tetrahedron Lett. 24:4117–4120.
Ojika, M., Kigoshi, H., Kuyama, H., Niwa, H., andYamada, K., 1985. Studies onPteridium aquilinum var.Latiusculum IV. Isolation of three p-hydroxystyrene glucosides and an efficient method for the isolation of ptaquiloside, an unstable bracken carcinogen.J. Nat. Prod. 48:634–637.
Ojika, M., Wakamatsu, K., Niwa, H., andYamada, K. 1987. Ptaquiloside. A potent carcinogen isolated from bracken fern,Pteridium aquilinum var.Latiusculum: Structure elucidation based on chemical and spectral evidence, and reactions with aminoacids, nucleotides, and nucleosides.Tetrahedron 43:5261–5274.
Ojika, M., Sugimoto, K., Okazaki, T., andYamada, K. 1989. Modification and cleavage of DNA by ptaquiloside. A new potent carcinogen isolated from bracken fern.J. Chem. Soc. Chem. Commun. 1989:1775–1777.
Ortega, F. 1990. El géneroPteridium en Venezuela: Taxonomiay distribution geográfica.Biollania 7:47–56.
Page, C.N. 1976. The taxonomy and phytogeography of bracken-a review.Bot. J. Linn. Soc. 73:1–34.
Page, C.N. 1982. The history and the spread of bracken in Britain.Proc. R. Soc. Edinburgh 81B:3–10.
Pamukcu, A.M., andPrice, J.M. 1969. Induction of intestinal and urinary bladder cancer in rats by feeding bracken fern (Pteris aquilina).J. Natl. Cancer Res. Inst. 43:275–281.
Pelletier, S.W., Chokshi, H.P., andDesai, H.K. 1986. Separation of diterpenoid alkaloid mixtures using vacuum liquid chromatography.J. Nat. Prods. 49:892–900.
Penberthy, J. 1893. Vegetable poisoning simulating anthrax in cattle.J. Comp. Pathol. 6:266–275.
Rosenberger, G. 1971. Nature, manifestations, cause and control of chronic enzootic hematuria in cattle.Vet. Med. Rev. 00:189–206.
Saito, K., Nagao, T., Matoba, M., Koyama, K., Natori, S., Murakami, T., andSaiki, Y. 1989. Chemical assay of ptaquiloside, the carcinogen ofPteridium aquilinum, and the distribution of related compounds in the pteridaceae.Phytochemistry 28:1605–1611.
Saito, M., Umeda, M., Enomoto, M., Hatanaka, Y., Natori, S., Yoshihira, K., Fukuoka, M., andKuroyanagi, M. 1975. Cytotoxicity and carcinogenicity of pterosins and pterosides, 1-indanone derivatives from bracken fern (Pteridium aquilinum)Experientia 31:824–831.
Santos, R.C.,Brasileiro-Fihlo, andSilva, M.E. 1989. Oncogenicity of bracken fern (Pteridium aquilinum) from Ouro Preto, Brazil, for rats fed low animal protein diets, p. 253,in J.A. Thompson and R.T. Smith (eds.). Bracken, Biology and Management. Institute of Agriculture and Science Occasional Publication 40. Sydney.
Shefield, E., Wolf, P.G., andHaufler, C.H. 1989. How big is a bracken plant.Weed Sci. 29:455–460.
Smith, B.L.,Lauren, D.R.,Embling, P.P., andAgnew, M.P. 1989. Ptaquiloside in Australian and New Zealand ferns as a cause of neoplasma, p. 241,in J.A. Thompson and R.T. Smith (eds.). Bracken, Biology and Management.Institute of Agriculture and Science Occasional Publication 40. Sydney.
Storrar, D.N. 1893. Cases of vegetable poisoning in cattle.J. Comp. Pathol. 6:276–279.
Targett, N.M., Kilcoyne, J.P., andGreen, B. 1979. Vacuum liquid chromatography. An alternative to common Chromatographic methods.J. Org. Chem. 44:4962–4964.
Tryon, R.M. 1941. A revision of the genusPteridium.Rhodora 43:1–31.
Van Der Hoeven, J.C.M., Lagerweij, W.J., Posthumus, M.A., van Veldhuizen, A., andHolterman, H.A.J. 1983. Aquilide A. A new mutagenic compound isolated from bracken fern (Pteridium aquilinum (L.) Kuhn).Carcinogenesis 4:1587–1590.
Villalobos-Salazar, J. 1985. Carcinogenicidad delPteridium aquilinum y alta incidencia de cáncer gástrico en Costa Rica.Rev. Cost. Cienc. Med. 6:131.
Villalobos-Salazar, J. 1987.Pteridium aquilinum and gastric cancer. Abstract, XXIII World Veterinary Congress, p. 90, August 15, Montreal Canada.
Villalobos-Salazar, J.,Hasbun, C.,Meneses, A.,Roias, J.L., andSingaran, M. 1988. Carcinogenicity ofPteridium aquilinum var.Caudatum in mice. Abstract of the 9th World Congress on animal, plant and microbial toxins, p. 92, July 31, Stillwater, Oklahoma.
Villalobos-Salazar, J., Meneses, A., Rojas, J.L., Mora, J., Porras, R.E., andHerrero, M.V. 1989a. Bracken-derived carcinogens as affecting animal and human health in Costa Rica, p. 40,in J.A. Taylor (ed.). Bracken Toxicity and Carcinogenicity as Related to Animal and Human Health. Special publication of International Bracken Group. Geography Department, University College of North Wales, Aberystwyth, Wales.
Villalobos-Salazar, J.,Meneses, A., andSalas, J. 1989b. Carcinogenic effects in mice of milk from cows fed on bracken fernPteridium aquilinum, p. 247,in J.A. Thompson and R.T. Smith (eds.). Bracken, Biology and Management. Institute of Agriculture and Science Occasional Publication 40. Sydney.
Yoshihira, K., Fukuoka, M., Kuroyanagi, M., andNatori, S. 1971. 1-Indanone derivatives from bracken,Pteridium aquilinum var.Latiusculum Chem. Pharm. Bull. 19:1491–1495.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Alonso-amelot, M.E., Pérez-mena, M., Calcagno, M.P. et al. Ontogenic variation of biologically active metabolites ofPteridium aquilinum (L. Kuhn) pterosins A and B, and ptaquiloside in a bracken population of the tropical andes. J Chem Ecol 18, 1405–1420 (1992). https://doi.org/10.1007/BF00994365
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00994365
