Abstract
Cell-suspension cultures of Centaurium erythraea and Centaurium littorale (Gentianaceae) respond to methyl jasmonate and yeast extract with a differential accumulation of xanthones. Methyl jasmonate induced the formation of 1-hydroxy-3,5,6,7-tetramethoxyxanthone, the amount of which increased in both cell cultures around 10 h after addition. A substantial increase in the activity of phenylalanine ammonia-lyase (PAL) was not observed. When challenged with yeast extract the cell cultures accumulated l,5-dihydroxy-3-methoxyxanthone. This appeared rapidly after addition of yeast extract in C. erythraea but its amount in C. littorale increased only after a lag phase of 25 h. While PAL activity in C. erythraea was strongly suppressed a fourfold increase in its activity was found in C. littorale. Both elicited xanthones accumulated intracellularly. A scheme for xanthone biosynthesis in the two cell cultures is proposed.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
Abbreviations
- TLC:
-
thin-layer chromatography
- NMR:
-
nuclear magnetic resonance
- PAL:
-
phenylalanine ammonia-lyase
References
Abou-Shoer M, Boettner FE, Chang CJ, Cassady JM (1988) Antitumour and cytotoxic xanthones of Psorospermum febrifugum. Phytochemistry 27: 2795–2800
Anderson JA (1986) Conversion of emodin to chrysophanol in a cell-free system from Pyrenochaeta terrestris. Phytochemistry 25: 103–106
Ayers AR, Ebel J, Valent B, Albersheim P (1976) Host-pathogen interactions.X. Fractionation and biological activity of an elicitor isolated from the mycelial walls of Phytophthora megasperma var. soyae. Plant Physiol 57: 760–765
Beerhues L, Berger U (1994) Xanthones in cell suspension cultures of two Centawium species. Phytochemistry 35: 1227–1231
Bennett GJ, Lee HH (1988) The biosynthesis of mangostin: The origin of the xanthone skeleton. J Chem Soc Chem Commun: 619–620
Bennett GJ, Lee HH (1989) Xanthones from Guttiferae. Phytochemistry 28: 967–998
Brackmann R, Fuchs G (1993) Enzymes of anaerobic metabolism of phenolic compounds.4-Hydroxybenzoyl-CoA reductase (dehydroxylating) from a denitrifying Pseudomonas species. Eur J Biochem 213: 563–571
Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72: 248–254
Delle Monache F, Marquina Mac-Quhae M, Delle Monache G, Marini Bettolo GB, Alves de Lima R (1983) Xanthones, xanthonolignoids and other constituents of the roots of Vismia guaramirangae. Phytochemistry 22: 227–232
Edwards R, Blount JW, Dixon RA (1991) Glutathione and elicitation of the phytoalexin response in legume cell cultures. Planta 184:403–409
Eilert U, Kurz WGW, Constabel F (1985) Stimulation of sanguinarine accumulation in Papaver somniferum cell cultures by fungal elicitors. J Plant Physiol 119:65–76
Fujita M, Inoue T (1977) Biosynthesis of mangiferin in Anemarrhena asphodeloides: Intact incorporation of C6-C3 precursor into xanthone. Tetrahedron Lett 51: 4503–4506
Fujita M, Inoue T (1981) Further studies on the biosynthesis of mangiferin in Anemarrhena asphodeloides: Hydroxylation of the shikimate-derived ring. Phytochemistry 20: 2183–2185
Fukamiya N, Okano M, Kondo K, Tagahara K (1990) Xanthones from Swertia punicea. J Nat Prod 53: 1543–1547
Gundlach H, Müller MJ, Kutchan TM, Zenk MH (1992) Jasmonic acid is a signal transducer in elicitor-induced plant cell cultures. Proc Natl Acad Sci USA 89: 2389–2393
Gupta P, Lewis JR (1971) Biogenesis of xanthones in Gentiana lutea. J Chem Soc (C): 629–631
Hauffe KD, Hahlbrock K, Scheel D (1986) Elicitor-stimulated furanocoumarin biosynthesis in cultured parsley cells: S-Adenosyl-L-methionine:bergaptol and S-adenosyl-L-methionine:xanthotoxol O-methyltransferases. Z Naturforsch 41c: 228–239
Hostettmann K, Hostettmann M (1989) Xanthones. In: Harborne JB (ed) Methods in plant biochemistry, vol 1: Plant phenolics. Academic Press, London, pp 493–508
Jinsart W, Ternal B, Buddhasukh D, Polya GM (1992) Inhibition of wheat embryo calcium-dependent protein kinase and other kinases by mangostin and γ-mangostin. Phytochemistry 31: 3711–3713
Keβmann H, Barz W (1987) Accumulation of isoflavones and pterocarpane phytoalexins in cell suspension cultures of different cultivars of chickpea (Cicer arietinum). Plant Cell Rep 6: 55–59
Lin CN, Liou SS, Ko FN, Teng CM (1993) γ-Pyrone compounds.IV.Synthesis and antiplatelet effects of mono- and dioxygenated xanthones and xanthoneoxypropanolamine. J Pharm Sci 82: 11–16
Linsmaier EM, Skoog F (1965) Organic growth factor requirements of tobacco tissue cultures. Physiol Plant 18: 100–127
Liswidowati FM, Hohmann F, Schwer B, Kindl H (1991) Induction of stilbene synthase by Botrytis cinerea in cultured grapevine cells. Planta 183: 307–314
Minami H, Kinoshita M, Fukuyama Y, Kodama M, Yoshizawa T, Sugiura M, Nakagawa K, Tago H (1994) Antioxidant xanthones from Garcinia subelliptica. Phytochemistry 36: 501–506
Mizukami H, Tabira Y, Ellis BE (1993) Methyl jasmonate-induced rosmarinic acid biosynthesis in Lithospermum erythrorhizon cell suspension cultures. Plant Cell Rep 12: 706–709
Mueller MJ, Brodschelm W, Spannagl E, Zenk MH (1993) Signaling in the elicitation process is mediated through the octadecanoid pathway leading to jasmonic acid. Proc Natl Acad Sci USA 90: 7490–7494
Quillinan AJ, Scheinmann F (1973) Studies in the xanthone series. Part XII. A general synthesis of polyoxygenated xanthones from benzophenone precursors. J Chem Soc Perkin Trans l: 1329–1337
Rocha L, Marston A, Kaplan MAC, Stoeckli-Evans H, Thull U, Testa B, Hostettmann K (1994) An antifungal γ-pyrone and xanthones with monoamine oxidase inhibitory activity from Hypericum brasiliense. Phytochemistry 36: 1381–1385
Schimmer O, Mauthner H (1994) Centaurium erythraea Rafn.Tausen-dgüldenkraut. Portrait einer Arzneipflanze. Z Phytother 15: 297–304
Schumacher HM, Gundlach H, Fiedler F, Zenk MH (1987) Elicitation of benzophenanthridine alkaloid synthesis in Eschscholtzia cell cultures. Plant Cell Rep 6: 410–413
Seitz HU, Seitz U, Alfermann W (1985) Pflanzliche Gewebekultur. Ein Praktikum. Fischer, Stuttgart
Sembdner G, Parthier B (1993) The biochemistry and the physiological and molecular actions of jasmonates. Annu Rev Plant Physiol Plant Mol Biol 44: 569–589
Sparenberg B, Demisch L, Hölzl J (1993) Untersuchungen über antidepressive Wirkstoffe von Johanniskraut. Pharm Ztg Wiss 138: 50–54
Sumaryono W, Proksch P, Hartmann T, Nimtz M, Wray V (1991) Induction of rosmarinic acid accumulation in cell suspension cultures of Orthosiphon aristatus after treatment with yeast extract. Phytochemistry 30: 3267–3271
Takagi S, Yamaki M (1982) Studies on the constituents of Erythraea centaurium (Linné) Persoon.III. Isolation and structure of xanthones. Yakugaku Zasshi 102: 546–548
Threlfall DR, Whitehead IM (1989) The use of metal ions to induce the formation of secondary products in plant tissue culture. In: Robins RJ, Rhodes MJC (eds) Manipulating secondary metabolism in culture. Cambridge University Press, Cambridge, pp 51–56
Author information
Authors and Affiliations
Additional information
Dedicated to Professor R. Wiermann on the occasion of his 60th birthday
We thank Drs. Delle Monache (Istituto di Chimica e Chimica Clinica, Roma, Italy), Okano (Faculty of Integrated Arts and Sciences, Higashihiroshima, Japan), and Takagi (Faculty of Pharmaceutical Sciences, Nishinomiya, Japan) for samples of authentic reference compounds. Methyl jasmonate and Pmg elicitor were kind gifts from Drs. Gröger (Institut für Biochemie der Pflanzen, Halle, Germany), and Scheel (Max-Planck-Institut für Züchtungsforschung, Köln, Germany), respectively. We are grateful to Drs. Eckhardt (Institut für Organische Chemie und Biochemie, Bonn, Germany), and Hartmann and Tomberg (Institut für Physiologische Chemie, Bonn, Germany) for mass and NMR spectra and to the Deutsche Forschungsgemeinschaft for financial support. We thank Dr. Leistner (Institut für Pharmazeutische Biologie, Bonn, Germany) for critical comments on the manuscript.
Rights and permissions
About this article
Cite this article
Beerhues, L., Berger, U. Differential accumulation of xanthones in methyl-jasmonate- and yeast-extract-treated cell cultures of Centaurium erythraea and Centaurium littorale . Planta 197, 608–612 (1995). https://doi.org/10.1007/BF00191567
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00191567