Abstract
Three quinones (2,3-dimethyl-1,4-benzoquinone; 2,5-dimethyl 1,4-benzoquinone; and 2,3,5-trimethyl-1,4-benzoquinone) and two phenols (2,3-dimethylphenol and 2-methyl-5-ethylphenol) were isolated from the defensive secretions of four species of opilionids (suborder Laniatores) from the Canal Zone. Phenols had not previously been reported from opilionids, and 2-methyl-5-ethylphenol was not known as a natural product. The secretions, which are mixed with regurgitated enteric fluid upon discharge, are administered by the animals by leg dabbing.
Similar content being viewed by others
References
Altman, P.L., andDittmer, D.S. (eds.). 1973. Biology Data Book, 2nd Ed., Vol. II, Sect. 80, Part I. Federation of the American Society of Experimental Biologists, Bethesda, Maryland.
Bishop, S.C. 1950. The life of a harvestman.Nature Mag. 276:264–267.
Blum, M.S., andEdgar, A.L. 1971. 4-Methyl-3-heptanone: Identification and role in opilionid exocrine secretions.Insect Biochem. 1:181–188.
Eisner, T., Hurst, J.J., andMeinwald, J. 1963. Defense mechanisms of arthropods. XI. The structure, function, and phenolic secretions of the glands of a chordeumoid millipede and a carabid beetle.Psyche 70:94–116.
Eisner, T., Kluge, A.F., Carrel, J.C., andMeinwald, J. 1971. Defense of a phalangid: Liquid repellent administered by leg dabbing.Science 173:650–652.
Eisner, T., Aneshansley, D., Eisner, M., Rutowski, R., Chong, B., andMeinwald, J. 1974. Chemical defense and sound production in Australian tenebrionid beetles(Adelium spp.).Psyche 81:189–208.
Estable, C., Ardao, M.I., Brasil, N.P., andFieser, L.F. 1955. Gonyleptidine.J. Am. Chem. Soc. 77:4942.
Fieser, L.F., andArdao, M.I. 1956. Investigation of the chemical nature of gonyleptidine.J. Am. Chem. Soc. 78:774–781.
Irvine, W.J., andSaxby, M.J. 1968. The constituents of certain tobacco types. I. Steam volatile phenols of Latakia.Phytochemistry 7:277–281.
Jones, T.H., Conner, W.E., Kluge, A.F., Eisner, T., andMeinwald, J. 1976. Defensive substances of opilionids.Experientia. 32:1234–1235.
Juberthie, C. 1961a. Structure des glandes odorantes et modalités d'utilisation de leur sécretion chez deux opiliones cyphophthalmes.Bull. Soc. Zool. France 86:106–116.
Juberthie, C. 1961b. Structure et fonction des glandes odorantes chez quelques opilions (Arachnida).Verh. Dtsch. Zool. Ges. 1961:533–537.
Lawrence, R.F., 1938. The odoriferous glands of some South African harvestspiders.Trans. R. Soc. S. Afr. 25:333–342.
Meinwald, J., Kluge, A.F., Carrel, J.E., andEisner, T. 1971. Acyclic ketones in the defensive secretion of a “daddy longlegs”(Leiobunum vittatum).Proc. Natl. Acad. Sci. U.S.A. 68:1467–1468.
Morgan, G.T., andPettet, A.E.G. 1934. Homologues of phenol.J. Chem. Soc. 1934:418–422.
Shrewsbury, D.D. 1960. The infrared spectra of alkyl phenols.Spectrochim. Acta 16:1294–1311.
Stenhagen, E., Abrahamsson, S., andMcLafferty, F.W. 1974. Registry of Mass Spectral Data, Vol. 1. Wiley, New York, pp. 186, 283, 391.
Author information
Authors and Affiliations
Additional information
Paper no. 53 of the seriesDefense Mechanisms of Arthropods.
Rights and permissions
About this article
Cite this article
Eisner, T., Jones, T.H., Hicks, K. et al. Quinones and phenols in the defensive secretions of neotropical opilionids. J Chem Ecol 3, 321–329 (1977). https://doi.org/10.1007/BF00988447
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00988447