Abstract
The production of labdanum exudate byCistus ladanifer L. is highly seasonal, reaching a maximum concentration during summer and a minimum concentration in winter. Because this exudate strongly absorbs in the wavelength range of 260–400 nm (the near-UV-visible range), it may be important biologically as an UV-visible filter. Separation of exudate components has been achieved by reverse-phase high-performance liquid chromatography (HPLC).The retention times of HPLC chromatograms and the spectral characteristics (absorption and fluorescence) of the exudate identify flavonoids as the most relevant chromophores regarding the potency of the exudate as a UV-visible filter. HPLC studies show that kaempferol-3-(O)methyl, kaempferol-3,7-di(O)methyl, and apigenin-4′-(O)methyl are the most enriched flavonoids in the exudate.Other flavonoids [apigenin, apigenin-7-(O)methyl, apigenin-7,4′-di(O)methyl, kaempferol-3,4′-di(O)methyl and kaempferol-3,7,4′-tri(O)methyl] are present in the exudate as minor components, e.g., each contributes by less than 10% to total flavonoids.The ratio of kaempferols to apigenins of the exudate also shows seasonal variation (maximum value in summer and minimum in spring). However, due to the similar absorption spectra of both groups of flavonoids, this has a minor influence on the exudate's ability to filter near-UV-visible radiation.
Similar content being viewed by others
References
Bohm, B.A. 1987. Intraespecific flavonoids variation.Bot. Rev. 53:197–279.
Bola¯nos, M.M., andGuinea, E. 1949. Jarales y jara, Ares, Madrid, Spain.
Cabezas, J., andEscudero, J.C. 1989. Estudio termométrico de la provincia de Badajoz. Directión General de Investigación, Extensión y Capacitación Agraria, Badajoz, Spain.
Cabezas, J.,Nu¯nez, E.,Escudero, J.C., andMarroquín, A. 1983. Estudio pluviométrico de la provincia de Badajoz. Consejería de Agricultura y Comercio, Badajoz, Spain.
Caldwell, M.M. 1971. Solar UV irradiation and the growth and development of higher plants, pp.n 131–171,in A.C. Giese (ed.). Photophysiology. Academic Press, New York.
Chaves, N. 1991. Estudio sobre la variación estacional de la composición del ládano enCistus ladanifer L. Masters thesis. Facultad de Ciencias, Universidad de Extremadura, Badajoz, Spain.
Fimin, J.L., Wilson, K.E., Rossen, L., andJohnston, A.W.B. 1986. Flavonoid activation of nodulation genes inRhizobium reversed by other compounds present in plants.Nature 32:34–43.
Font-Tullot, I. 1984. Atlas de la radiación solar en España.Annual Report of the National Institute of Meterology, Madrid, Spain.
Hahlbrock, K., Krenzaler, F., Ragg, H., Fautz, E., andFuhn, D.N. 1982. Biochemistry of Differentiation and Morphogenesis, pp. 34–43,in L. Jaenicke (ed.). Springer, Berlin.
Harborne, J.B. 1986. Nature, Distribution and function of plant flavonoids, pp. 15–24,in V. Cody, J.R. Middleton, and J.B. Harborne (eds.). Plant Flavonoids in Biology and Medicine: Biochemical, Pharmacological and Structure-Activity Relationships. Alan R. Liss, New York.
Hedin, P.A., Jenkins, J.N., Collum, D.H., White, W.H., andParrott, W.L. 1983. Multiple factors in cotton contributing to resistance to the tobacco budworm,Heliothis virescens, pp. 347–370,in P.A. Hedin (ed.). Plant Resistance to Insects. American Chemical Society, Washington, D.C.
Herrera, C.M. 1984. Tipos morfológicos y funcionales en plantas del matorral mediterráneo del sur de España.Stud. Oecol. 5:7–34.
Hrazdina, G., andParsons, G.F. 1982. Induction of flavonoid synthesizing enzymes by light in etiolated pea (Pisum sativum c.v Hidfreezen) seedlings.Plant Physiol. 70:506–510.
J. De Pascual, Pascual, T., Urones, J.G., andBasabe, M.P. 1974. Flavonoides deCistus ladanifer L.An. Quím. 70:155–157.
Knogge, W., andWessenböck, G. 1986. Tissuedistribution of secondary phenolic biosynthesis in developing primary leaves ofAvena sativa.Planta 167:196–205.
Les, H., andSheridan, J. 1990. Biochemical heterophylly and flavonoid evolution in North AmericanPotamogeton (Potamogetonaceae).Am. J. Bot. 77:453–465.
Lim, C.K. 1986, HPLC of small molecules, IRL Press, Practical Approach Series, Oxford, U.K.
Markham, K.R. 1982. Techniques of Flavonoids Identification. Academic Press, London.
Matern, V., Heller, W., andHimmelspach, K. 1983. Conformational changes of apigenin 7-O-6-O malonyl glucoside, a vacuolar pigment from parsley with solvent composition and proton concentration.Eur. J. Biochem. 133:439–448.
Matias, M.D. 1990. Análisis de la estructura espacio-temporal de comunidades vegetales en campos abandonados de los Arribes del Duero. PhD thesis. Facultad de Biologiía, Universidad de Salamanca, Spain.
McClure, J.W. 1975. Physiology and functions of Flavonoids, pp. 970–1055, in J.B. Harborne, T.J. Mabry, and H. Mabry (eds.). The Flavonoids. Academic Press, New York.
McClure, J.W. 1986. Physiology of flavonoids. pp. 77–85,in V. Cody, J.R. Middleton, and J.B. Harborne (eds.). Plants Flavonoids in Biology and Medicine: Biochemical, Pharmacological and Structure-Activity Relationships. Alan R. Liss, New York.
Nu¯nez, E. 1989. Ecología del jaral deCistus ladanifer L. PhD thesis. Facultad de Ciencias, Universidad de Extremadura, Badajoz, Spain.
Ohno, Y. 1981. Gas Chromatographic characterization of ladanum resinoid and detection of adulterants.Kauzei Chuo Bunsekisho Ho 22:15–21.
Peters, N.K., Frost, J.W., andLong, S.R. 1986. A plant flavone luteolin induces expression ofRhizobium meliloti nodulation genes.Science 233:977–980.
Proksch, P., andGülz, P.-G. 1984. Methylated flavonoids fromCistus ladanifer L. andCistus palhinhae and their taxonomic implications.Phytochemistry 23:470–472.
Rawn, J.D. 1989. Biochemistry. McGraw-Hill, New York.
Roberts, M.L., andHaynes, R.R. 1986. Flavonoids systematics ofPotamogeton subsectionsPerfoliati andPraelongi (Potamogetonaceae).Nord. J. Bot. 6:291–294.
Schmelzer, E., Jahnen, W., andHahlbrock, K. 1988. In situ localization of light-induced chalcone synthase mRNA, chalcone synthase and flavonoid end products in epidermal cells of parsley leaves.Proc. Natl. Acad. Sci. U.S.A. 85:2989–2993.
Schnabl, H., Weissenböck, G., andScherf, H. 1986. In vivo microspectrophotometric characterization of flavonol glycosides inVicia faba guard and epidermal cells.J. Exp. Bot. 174:61–72.
Swain, T. 1970. Biochemical Evolution and the Origin of Life. North-Holland, Amsterdam.
Swain, T. 1975. Evolution of flavonoid compounds, pp. 1096–1129,in J.B. Harbone, T.J. Mabry, and H. Mabry (eds.). The Flavonoids. Academic Press, New York.
Tomás-Llorente, F., García-Grau, M., andTomás-Barberán, F. 1990. Flavonoids fromVicia faba seed exudates.Z Naturforsch. 45:1070–1072.
Vogt, T., Proksch, P., andGülz, P.-G. 1987a. Epicuticular flavonoid aglycones in the genusCistus, Cistaceae.J. Plant Physiol. 131:25–36.
Vogt, T., Proksch, P., Gülz, P.-G., andWollenweber, E. 1987b. Rare 6- and 8-O-methylated epicuticular flavonols from twoCistus species.Phytochemistry 26:1027–1030.
Wollenweber, E., andDietz, V.H. 1981. Occurrence and distribution of tree flavomoid aglycones in plants.Phytochemistry 20:869–932.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Chaves, N., Escudero, J.C. & Gutiérrez-Merino, C. Seasonal variation of exudate ofCistus ladanifer . J Chem Ecol 19, 2577–2591 (1993). https://doi.org/10.1007/BF00980692
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00980692