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Myristicin, safrole, and fagaramide as phytosynergists of xanthotoxin

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Abstract

The methylenedioxyphenyl-containing (MDP) inhibitors of mixed-function oxidase detoxification enzymes, myristicin, safrole, fagaramide, and isosafrole, occur with xanthotoxin or other toxic furanocoumarins in plants of the families Umbelliferae and Rutaceae. All four MDP compounds have a synergistic effect on the toxicity of xanthotoxin toHeliothis zea. Myristicin also increased the phototoxicity of xanthotoxin in the presence of UV light. The term phytosynergist is used to describe plant compounds that are present at concentrations producing no toxic effect by themselves but have a synergistic effect on cooccurring toxins.

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References

  • Berenbaum, M. 1978. Toxicity of a furanocoumarin to armyworms: A case of biosynthetic escape from herbivores.Science 201:532–534.

    CAS  PubMed  Google Scholar 

  • Berenbaum, M., andNeal, J.J. 1985. Synergism between myristicin and xanthotoxin, a naturally cooccurring plant toxicant.J. Chem. Ecol. 11:1349–1358.

    Article  CAS  Google Scholar 

  • Berenbaum, M., andNeal, J.J. 1986. Interactions among allelochemicals and insect resistance in crop plants, pp. 416–430,in G.R. Waller (ed.). Allelochemicals: Role in Agriculture and Forestry. American Chemical Society Symposium Series No. 330 Washington, D.C.

  • Bull, D.L., Ivie, G.W., Beier, R.C., Pryor, N.W., andOertli, E.H. 1984. Fate of photosensitizing furanocoumarins in tolerant and sensitive insects.J. Chem. Ecol. 10:893–911.

    Article  CAS  Google Scholar 

  • Bull, D.L., Ivie, G.W., Beier, R.C., andPryor, N.W., 1986. In vitro metabolism of a linear furanocoumarin (8-methoxypsoralen, xanthotoxin) by mixed-function oxidases of larvae of the black swallowtail butterfly and the fall armyworm.J. Chem. Ecol. 12:885–892.

    Article  CAS  Google Scholar 

  • Ceska, O., Chaudhary, S.K., Warrington, P.J., andAshwood-Smith, M.J. 1987. Photoactive furanocoumarins in fruits of some umbellifers.Phytochemistry 26:165–169.

    Article  Google Scholar 

  • Chang, P.T.O. 1976. Phytochemical studies onHelietta parvifolia. Doctoral dissertation. University of Illinois Medical Center, Chicago, Illinois.

    Google Scholar 

  • Harborne, J.B. 1971. Flavonoid and phenylpropanoid pattern in the Umbelliferae, pp. 293–314,in V.H. Heywood (ed.). Biology and Chemistry of the Umbelliferae. Academic Press, London.

    Google Scholar 

  • Hegnauer, R. 1973. Chemotaxonomie der Pflanzen, Band 6. Birkhauser-Verlag. Basel. Pages 174–239; 554–629.

    Google Scholar 

  • Hodgson, E. 1985. Microsomal mono-oxygenases, pp. 225–321,in G.A. Kerkut and L.I. Gilbert (eds.). Comprehensive Insect Physiology, Biochemistry and Pharmacology. Pergammon Press, New York.

    Google Scholar 

  • Hodgson, E., andPhilpot, R.M. 1974. Interaction of methylenedioxyphenyl (1,3-benzodioxole) compounds with enzymes and their effect on mammals.Drug Metab. Rev. 3:231–301.

    PubMed  CAS  Google Scholar 

  • Hodisan, V., Popescu H., andFagarasan, E. 1980. Studies onAnethum graveolens. II. Chemical composition of essential oil from fruits. Contrib. Bot., Univ. Babes-Bolyai Cluj, Gradina Bot. pp. 263–266;Chem. Abstr. 94:136149d (1981).

  • Krieger, R.I., Feeny, P.P., andWilkinson, C.F. 1971. Detoxication enzymes in the guts of caterpillars: An evolutionary answer to plant defenses?Science 172:579–581.

    PubMed  CAS  Google Scholar 

  • LaForge, F.B., andBarthel, W.F. 1944. A new constituent isolated from southern prickly-ash bark.J. Org. Chem. 9:250–253.

    Article  CAS  Google Scholar 

  • Lichtenstein, E.P., andCasida, J.E. 1963. Myristicin, an insecticide and synergist occurring naturally in the edible parts of parsnip.J. Agric. Food Chem. 11:410–415.

    Article  CAS  Google Scholar 

  • Murray, R.D.H., Mendez, J., andBrown, S.A. 1982. The Natural Coumarins. John Wiley & Sons, New York.

    Google Scholar 

  • SAS Institute Inc. 1982. SAS User's Guide: Statistics. SAS Institute Inc., Cary, North Carolina. Pages 287–292.

    Google Scholar 

  • Shulgin, A.T. 1966. Possible implication of myristicin as a psychotropic substance.Nature 210:380–384.

    PubMed  CAS  Google Scholar 

  • Thoms, H. 1911. Über die Konstitution des Xanthotoxins und seine Beziehungen zum Bergapten.Chem. Ber. 44:3325–3336.

    Google Scholar 

  • Thomas, H., andThümen, F. 1911. Über das Fagaramide, einen neuen stickstoffhaltingen Stoff aus der Wurzelrinde vonFagara xanthoxyloides Lam.Chem. Ber. 44:3717–3730.

    Article  Google Scholar 

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Taken in part from a thesis submitted to the Graduate College of the University of Illinois at Urbana-Champaign in partial fulfillment of the requirements for the degree of Doctor of Philosophy, June 1987.

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Neal, J.J. Myristicin, safrole, and fagaramide as phytosynergists of xanthotoxin. J Chem Ecol 15, 309–315 (1989). https://doi.org/10.1007/BF02027792

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