Abstract
Seedlings ofAgeratina adenophora accumulate the chromenes demethoxyencecalin, encecalin and demethylencecalin. More than 80% of the total chromenes within the seedling are confined to the leaves where they are stored within the mesophyll. Metabolism of the chromenes during development of the seedlings was subjected to analysis by high-performance liquid chromatography. The accumulation kinetics obtained, as well as feeding experiments with non-radioactive chromenes, showed the bioconversion of these compounds to proceed from demethoxyencecalin via hydroxylation yielding demethylencecalin, followed by methylation yielding encecalin. Inhibitor studies with glyphosate indicate that the chromenes arise from precursors derived from the shikimic-acid pathway.
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Abbreviations
- HPLC:
-
high-performance liquid chromatography
References
Bohlmann, F., Gupta, R.K. (1981) Six cadinene derivatives fromAgeratina adenophora. Phytochemistry20, 1432–1433
Bowers, W.S., Ohta, T., Cleere, J.S., Marsella, P.A. (1976) Discovery of insect antijuvenile hormones in plants. Science193, 542–547
Holländer, H., Amrhein, N. (1980) The site of the inhibition of the shikimate pathway by glyphosate. Plant Physiol.66, 823–829
Isman, M.B., Proksch, P. (1985) Deterrent and insecticidal chromenes and benzofurans fromEncelia (Asteraceae). Phytochemistry24, 1949–1951
Proksch, P. (1985) Vorkommen und biologische Bedeutung von Benzopyranen (Chromenen) und Benzofuranen in den Asteraceae. Plant Syst. Evol.150, 89–100
Proksch, P., Proksch, M., Towers, G.H.N., Rodriguez, E. (1983) Phototoxic and insecticidal activities of chromenes and benzofurans fromEncelia. J. Nat. Prod.46, 331–334
Proksch, P., Rodriguez, E. (1982) High-performance liquid chromatography of chromenes and benzofurans from the genusEncelia (Asteraceae). J. Chromatogr.240, 543–546
Proksch, P., Rodriguez, E. (1983) Chromenes and benzofurans of the Asteraceae, their chemistry and biological significance. Phytochemistry22, 2335–2348
Rosenthal, G.A., Janzen, D.H. (eds.) (1979) Herbivores, their interaction with secondary plant metabolites. Academic Press, New York London
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Proksch, P., Palmer, J. & Hartmann, T. Metabolism and bioconversion of chromene derivatives inAgeratina adenophora (Asteraceae). Planta 169, 130–134 (1986). https://doi.org/10.1007/BF01369784
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DOI: https://doi.org/10.1007/BF01369784