Skip to main content
Log in

Isolation and characterization of glucocapparin inIsomeris arborea nutt

  • Published:
Journal of Chemical Ecology Aims and scope Submit manuscript

Abstract

Isomeris arborea (Capparaceae), is the only woody caper endemic to southern California and northern Baja. Methylglucosinolate, also known as glucocapparin, was the only glucosinolate found inI. arborea organs by paper chromatography of the thiourea derivatives and was quantitatively determined by gas chromatography by hydrolytic products. The concentration of glucocapparin ranged from an average of 4.6 mg/g wet weight in mature leaves to 5.2 mg/g wet weight in immature leaves. Buds averaged 6.2 mg/g wet weight and capsule walls 1.8 mg/g wet weight. Seeds contained an average of 14.3 mg/g wet weight of glucocapparin. Glucocapparin concentration was found to vary significantly among the mature leaves of individuals within a single population. This compound is known to be deleterious to nonadapted herbivores and may be implicated in the chemical defense mechanism ofI. arborea.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Cole, R.A. 1976. Isothiocyanates, nitriles, and thiocyanates as products of autolysis of glucosinolates in Cruciferae,Phytochemistry 15:759–762.

    Google Scholar 

  • Daxenbichler, M.E., andVan Etten, C.H. 1977. Glucosinolates and derived products in cruciferous vegetables: Gas-liquid chromatographic determination of the aglucon derivatives from cabbage.J. Assoc. Off. Agric. Chem. 60:950–953.

    Google Scholar 

  • English, K.J. 1983. Development and mortality ofMurgantia histrionica in relation to food quality. MS thesis. San Diego State University, p. 84.

  • Erickson, J.M., andFeeny, P. 1974. Sinigrin: A chemical barrier to the black swallowtail butterfly,Papilio polyxenes.Ecology 55:103–111.

    Google Scholar 

  • Feeny, P. 1976. Plant apparency and chemical defense.Recent Adv. Phytochem. 10:1–39.

    Google Scholar 

  • Feeny, P. 1977. Defensive ecology of the Cruciferae.Ann. Mo. Bot. Gard. 64:221–234.

    Google Scholar 

  • Feeny, P., Paauwee, K.L., andDemong, J.J. 1970. Flea beetles and mustard oils: Host plant specificity ofPhyllotreta cruciferae andP. striolata adults (Coleoptera: Chrysomelidae).Annu. Rev. Entomol. Soc. Am. 63:832–841.

    Google Scholar 

  • Freeman, G.G., andMossadeghi, N. 1972. Studies on sulfur nutrition and flavor production in watercress (Rorippa nasturtium-aquaticum (L) Hayek)J. Honic. Sci. 47:375–387.

    Google Scholar 

  • Freeman, G.G., andMossadeghi, N. 1973. Studies on relationship between water regime and flavour stength in watercress (Rorippa nasturtium-aquaticum (L) Hayek), cabbage (Brassica oleracea capitata) and onion (Allium opa).J. Hortic. Sci. 48:365–378.

    Google Scholar 

  • Gil, V., andMacLeod, A.J. 1980. Benzylglucosinolate degradationinLepidium sativum: Effects of plant age and time of autolysis.Phytochemistry 19:1365–1368.

    Google Scholar 

  • Gmelin, R., andKjaer, A. 1970. Glucosinolates of nine Cruciferae and two Capparaceae species.Phytochemistry 10:2355–2358.

    Google Scholar 

  • Iltis, H.H. 1957. Studies in the Capparidaceae. III. Evolution and phylogeny of the west American Cleomoidae.Ann. Mo. Bot. Gard. 44:77–119.

    Google Scholar 

  • Josefsson, E. 1970. Glucosinolate content and amino acid composition of rapeseed (Brassica napus) meal as affected by sulfur and nitrogen nutrition.J. Sci. Food Agric. 21:98–103.

    Google Scholar 

  • Ju, H.C., Chong, C., Bible, B., andMullin, W. 1980. Seasonal variation in glucosinolate composition of rutabaga and turnip.Can. J. Plant Sci. 60:1295–1302.

    Google Scholar 

  • Kjaer, A., andSchuster, A. 1971. Glucosinolates inCapparis flexuosa of Jamaican origin.Phytochemistry 10:3155–3160.

    Google Scholar 

  • Kjaer, A., andThomson, H. 1963. Isothiocyanate-producing glucosides in species of Capparidaceae.Phytochemistry 2:29–32.

    Google Scholar 

  • Louda, S.M.,Farris, M., andBlua, M.J. 1985. Glucocapparin variation and insect damage toCleome serrulata (Capparaceae) along a soil moisture gradient.J. Chem. Ecol. In press.

  • MacLeod, A.J. 1976. Volatile flavour compounds of the Cruciferae, pp. 307–330,in J.G. Vaughen, A.J. MacLeod, and B.M.G. Jones (eds.). The Biology and Chemistry of the Cruciferae. Academic Press, London.

    Google Scholar 

  • MacLeod, A.J., andMacLeod, G. 1977. Synthesis and natural occurance of 8-methylthiooctanonitrile and 9-methylthiononanonitrile.Phytochemistry 16:907–909.

    Google Scholar 

  • McKey, D. 1974. Adaptive patterns in alkaloid physiology.Am. Nat. 108:305–320.

    Google Scholar 

  • Nuss, C. 1983. Feeding behavior and within-host feeding preferences of the harlequin bug,Margantia histrionica, on the bladderpod plant,Isomeris arborea. MS thesis. San Diego State University. 65 pp.

  • Olsen, O., andSorensen, H. 1979. Isolation of glucosinolates and the identification ofO-(α-L-rhamnopyranosyloxy) benzylglucosinolate fromReseda odorata.Phytochemistry 18:1547–1552.

    Google Scholar 

  • Rhoades, D.F. 1979. Evolution of plant chemical defense against herbivores, pp. 3–54,in G.A. Rosenthal and D.H. Janzen (eds.). Herbivores, Their Interaction with Secondary Plant Metabolites. Academic Press, New York.

    Google Scholar 

  • Rhoades, D.F., andCates, R.G. 1976. Towards a general theory of plant antiherbivore chemistry.Recent Adv. Phytochem. 10:168–213.

    Google Scholar 

  • Rodman, J.E. 1978. Glucosinolates, methods of analysis and some chemo-systematic problems.Phytochem. Bull. 11:6–31.

    Google Scholar 

  • Schoonhaven, L.M. 1972. Secondary plant substances and insects.Recent Adv. Phytochem. 5:197–224.

    Google Scholar 

  • Stoessl, A. 1970. Antifungal compounds produced by higher plants.Recent. Adv. Phytochem. 3:143–171.

    Google Scholar 

  • Van Etten, C.H., andDaxenbichler, M.E. 1977. Natural poisons. Glucosinolates and derived products in cruciferous vegetables: Total glucosinolate by retention on anion exchange resin and enzymatic hydrolysis to measure released glucose.J. Assoc. Off. Agric. Chem. 60:946–949.

    Google Scholar 

  • Van Etten, C.H., andTookey, H.L. 1979. Chemistry and the biological effects of glucosinolates, pp. 471–500,in G.A. Rosenthal and D.H. Janzen (eds.). Herbivores: Their Interaction with Secondary Plant Metabolites. Academic Press, New York.

    Google Scholar 

  • Van Etten, C.H., Daxenbichler, M.E., Williams, P.H. andKwolek, W.F. 1976. Glucosinolates and derived products in cruciferous vegetables. Analysis of the edible part from twenty-two varieties of cabbage.J. Agric. Food Chem. 24:452–455.

    Google Scholar 

  • Van Etten, C.H., Daxenbichler, M.E., Keudek, W.F., andWilliams, P.H. 1979. Distribution of glucosinolates in the pith, cambrialcortex, and leaves of the head in cabbage,Brassicae oleraceae L. J. Agric. Food Chem. 27:648–650.

    Google Scholar 

  • Youngs, C.G., andWetter, L.R. 1967. Microdetermination of the major individual isothiocya-nates and oxazolidinethiones in rapeseed.J. Am. Oil Chem. Soc. 44:551–554.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Blua, M.J., Hanscom, Z. Isolation and characterization of glucocapparin inIsomeris arborea nutt. J Chem Ecol 12, 1449–1458 (1986). https://doi.org/10.1007/BF01012363

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01012363

Key Words

Navigation