Abstract
A new butenolide, isosiphonodin [3-hydroxymethyl-2(5H)-furanone], along with a trace of siphonodin [4-hydroxymethyl-2(5H)-furanone], was isolated from fifth-instar larvae of the small ermine mothYponomeuta cagnagellus. Leaves of its host plant spindle-tree,Euonymus europaeus, were found to contain the same two butenolides with siphonodin being present as the major compound. TLC showed that isosiphonodin was also present in larvae or pupae of six other small ermine moths which did not feed on spindle-tree. InY. cagnagellus butenolides might be plant derived, while isosiphonodin in the other investigated small ermine moths is probably synthesized by the insect. The possible role of butenolides in the chemical defense of small ermine moths is discussed.
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Bergman, B.H.H., Beijersbergen, J.C.M., Overeem, J.C., andKaars Supesteijn, A., 1967. Isolation and identification of α-methylene-butyrolactone, a fungitoxic substance from tulips.Red. Trav. Chim. Pays-Bas 86:709–714.
Brongersma-Oosterhoff, U.W. 1967. Structure determination of the allergenic agent, isolated form tulip bulbs.Recl. Trav. Chim. Pays-Bas 86:705–708.
Brower, L.P. 1984. Chemical defence in butterflies, pp. 109–134,in R.I. Vane-Wright and P.R. Ackery (eds.). The Biology of Butterflies. Symposium of the Royal Entomological Society, London, Vol. 11. Academic Press, London.
Camps, P., Cardellach, J., Font, J., Ortuno, R.M., andPonsati, O. 1982. Studies on structurally simple α, β-butenolides. II. (−)-(S)-γ-hydroxymethyl-α, β-butenolide and derivatives fromd-ribonolactone; efficient synthesis of (−)-ranunculin.Tetrahedron 38:2395–2402.
Doelker, E., Kapétandis, I., andMirimanoff, A. 1969. Application de la remission et de la fluorescence au dosage direct sur chromatoplaque des digitaloides.Pharm. Acta Helv. 44:647–651.
Fung, S.Y. 1986. Alkaloids and cardenolides in sixteenEuonymus taxa.Biochem. Syst. Ecol. 14:371–373.
Nahrstedt, A., andDavis, R.H. 1986. Uptake of linamarin and lotaustralin from their foodplant by-larvae ofZygaena trifolii.Phytochemistry 25:2299–2302.
Pasteels, J.M., andDaloze, D. 1977. Cardiac glycosides in the defensive secretion of chrysomelid beetles: Evidence for their production by the insects.Science 197:70–72.
Pelletier, S.W., Joshi, B.S., andDesai, H.K. 1985. Techniques for isolation of alkaloids, pp. 181–185,in A.J. Vlietinck andR.A. Dominisse (eds.). Advances in Medicinal Plant Research. Wissenschaftliche Verlagsgesellschaft, Stuttgart.
Roeske, C.N., Seiber, J.N., Brower, L.P., andMoffitt, C.M. 1976. Milkweed cardenolides and their comparative processing by monarch butterflies (Danaus plexippus L.).Recent Adv. Phytochem. 10:93–167.
Rothschild, M. 1973. Secondary plant substances and warning colouration in insects, pp. 59–83,in H.F. van Emden (ed.). Insect/plant Relationships. Symposium of the Royal Entomological Society, London, Vol. 6. Blackwell Press, Oxford.
Rothschild, M., andReichstein, T. 1976. Some problems associated with the storage of cardiac glycosides by insects.Nova Acta Leopol. Suppl. 7:507–550.
Rothschild, M., Mummery, R., andFarrell, C. 1986. Carotenoids of butterfly models and their mimics (Lep: Papilionidae and Nymphalidae).Biol. J. Linn. Soc. 28:359–372.
Rowson, J.M. 1952. Studies in the genusDigitalis, Part I. The colorimetric estimation of digitoxin and preparations ofDigitalis purpurea.J. Pharm. Pharmacol. 4:814–830.
Ruijgrok, H.W.L. 1967. Over de verspreiding van ranunculine en cyanogene verbindingen bij de Ranunculaceae. Een bijdrage tot de chemotaxonomie van de familie. Thesis, University of Leiden.
Tori, K., Ishii, H., Wolkowski, Z.W., Chachaty, C., Sangare, M., Piriou, F., andLukacs, G. 1973. Carbon-13 nuclear magnetic resonance spectra of cardenolides.Tetrahedron Lett. 13:1077–1080.
Tschesche, R., andHoppe, H.-J. 1971. Über Narthesid A und B, zwei diastereomere Lacton-Glucoside und ihr antibiotisch wirksames Aglykon aus Beinbrech (Narthecium ossifragum Hud.)Chem. Ber. 104:3573–3581.
Wagner, H., andFlitsch, K. 1981. Neue monocyclische Lactone ausSiphonodon australe.Planta Med. 43:245–248.
Wagner, H., Flitsch, K., andJurcic, K. 1981. Cytotoxizät von Siphonosid und aliphatischen Estern des Siphonodins.Planta Med. 43:249–251.
Wagner, H., Bladt, S., andZgainski, E.M. 1983. Drogenanalyse: Dünnschichtchromatographische Analyse von Arzneidrogen, pp. 195–223. Springer Verlag, Berlin.
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Fung, S.Y., Herrebout, W.M., Verpoorte, R. et al. Butenolides in small ermine moths,Yponomeuta spp. (Lepidoptera: Yponomeutidae), and spindle-tree,Euonymus europaeus (Celastraceae). J Chem Ecol 14, 1099–1111 (1988). https://doi.org/10.1007/BF01019338
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DOI: https://doi.org/10.1007/BF01019338