Abstract:
White clover (Trifolium repens) plants were grown in the presence or absence of the arbuscular mycorrhizal fungus Glomus intraradices. Flavones, 4′,5,6,7,8-pentahydroxy-3-methoxyflavone and 5,6,7,8-tetrahydroxy-3-methoxyflavone, as well as two flavones 3,7-dihydroxy-4′-methoxyflavone and 5,6,7,8-tetrahydroxy-4 ′-methoxyflavone never previously reported in plants, were isolated. The known 3,5,6,7,8-pentahydroxy-4′-methoxyflavone, 2′,3′,4′,5 ′,6′-pentahydroxy-chalcone, 6-hydroxykaempferol, 4′,5,6,7,8-pentahydroxyflavone and 3,4′-dimethoxykaempferol were also obtained. Analysis of extracts obtained from roots and shoots revealed that the compositions of the flavonoid mixtures varied with growing conditions. Quercetin, acacetin and rhamnetin accumulated in roots of inoculated plants, whereas they were not detected in non-inoculated plants. © 2004 Published by Elsevier Ltd.
Registro:
Documento: |
Artículo
|
Título: | Flavonoids from shoots and roots of Trifolium repens (white clover) grown in presence or absence of the arbuscular mycorrhizal fungus Glomus intraradices |
Autor: | Ponce, M.A.; Scervino, J.M.; Erra-Balsells, R.; Ocampo, J.A.; Godeas, A.M. |
Filiación: | Depto. de Quím. Orgán., Fac. de Ciencias Exactas Y Naturales, CIHIDECAR-CONICET, Univ. Buenos A., Buenos Aires, Argentina Depto. de Biodiversidad Y Biol. Exp., Fac. de Ciencias Exactas Y Naturales, Univ. Buenos Aires, Pabellon I., Buenos Aires, Argentina Estac. Experimental de Zaidin, CSIC, (18008) Granada, Spain
|
Palabras clave: | 3,7-Dihydroxy-4 ′-methoxyflavone; 4′,5,6,7,8-Pentahydroxy-3- methoxyflavone; 5,6,7,8-Tetrahydroxy-3-methoxyflavone; Chalcone; Flavones; Flavonoids; Glomus intraradices; Leguminosae; Roots; Shoots; Trifolium repens; White clover; 2',3',4',5',6' pentahydroxychalcone; 3,4' dimethoxykaempferol; 3,5,6,7,8 pentahydroxy 4' methoxyflavone; 3,7 dihydroxy 2 (4 methoxyphenyl) 4h 1 benzopyran 4 one; 4',5,6,7,8 pentahydroxyflavone; 5,6,7,8 tetrahydroxy 2 (4 hydroxyphenyl) 3 methoxy 4h 1 benzopyran 4 one; 5,6,7,8 tetrahydroxy 2 (4 methoxyphenyl) 4h 1 benzopyran 4 one; 5,6,7,8 tetrahydroxy 3 methoxy 2 phenyl 4h 1 benzopyran 4 one; 6 hydroxykaempferol; acacetin; flavonoid; plant extract; quercetin; rhamnetin; unclassified drug; white clover extract; arbuscular mycorrhiza; article; Glomus intraradices; plant root; white clover; Flavones; Fungi; Magnetic Resonance Spectroscopy; Molecular Structure; Mycorrhizae; Plant Roots; Plant Shoots; Quercetin; Trifolium; Fabaceae; Fungi; Glomus; Glomus intraradices; Trifolium; Trifolium repens |
Año: | 2004
|
Volumen: | 65
|
Número: | 13
|
Página de inicio: | 1925
|
Página de fin: | 1930
|
DOI: |
http://dx.doi.org/10.1016/j.phytochem.2004.06.005 |
Título revista: | Phytochemistry
|
Título revista abreviado: | Phytochemistry
|
ISSN: | 00319422
|
CODEN: | PYTCA
|
CAS: | acacetin, 480-44-4; quercetin, 117-39-5; rhamnetin, 90-19-7; 4',5,6,7,8-pentahydroxy-3-methoxyflavone; 5,6,7,8-tetrahydroxy-3-methoxyflavone; acacetin, 480-44-4; Flavones; Quercetin, 117-39-5; rhamnetin, 90-19-7
|
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00319422_v65_n13_p1925_Ponce |
Referencias:
- Agrawal, P.K., (1989) Carbon-13 NMR of Flavonoids, , Amsterdam: Elsevier
- Banskota, A.H., Tezuka, Y., Adnyana, I.K., Ishii, E., Midorikawa, K., Matsushige, K., Kadota, S., Hepatoprotective and anti-Helicobacter pylori activities of constituents from Brazilian propolis (2001) Phytomedicine, 8, pp. 16-23
- Bellini, A., Venturella, P., The synthesis of hydroxychalcone and hydroxyflavone derivatives. IV. Condensation of 2-hydroxy-4-methoxymethoxyacetophenone with aromatic aldehydes. Synthesis of 7-hydroxyflavone, pratol, resocamphoride, resogalangin (1958) Annales de Chimie (Rome), 48, pp. 111-124
- Bellini, A., Venturella, P., Cusmano, S., Flavonoids components of citrus. II. 5,6,7,8,4′- Pentamethoxyflavone (ponkanetin) from Citrus deliciosa (1962) Annales de Chimie (Rome), 52, pp. 795-801
- Boege, F., Straub, T., Kehr, A., Boesenberg, Ch., Christiansen, K., Andresen, A., Jakob, F., Köhrle, J., Select novel flavones inhibit the DNA binding or DNA religation step of the eukaryotic topoisomerase I (1996) Journal of Biological Chemistry, 271, pp. 2262-2270
- Chaliha, B.P., Sastry, G.P., Rao, P.R., Citrus jambhiri peel. Isolation of a new flavone (1965) Tetrahedron, 21, pp. 1441-1443
- Edwards, J.M., Raffauf, R.F., Le Quesne, P.W., Antitumor plants. Part VII. Antineoplastic activity and cytotoxicity of flavones, isoflavones, and flavanones (1979) Journal of Natural Products, 42, pp. 85-91
- Fawe, A., Abou-Zais, M., Menzies, J.G., Belanger, R.R., Silicon-mediated accumulation of flavonoid phytoalexins in cucumber (1998) Phytopathology, 88, pp. 396-401
- Fracchia, S., Garcia-Romera, I., Godeas, A., Ocampo, J.A., Effect of the saprophytic fungus Fusarium oxysporum on arbuscular mycorrhizal colonization and growth of plants greenhouse and field trials (2000) Plant and Soil, 223, pp. 175-184
- Fracchia, S., Sampedro, I., Godeas, A., Ocampo, J.A., Garcia-Romera, I., Interaction between soil yeast Rhodotorula mucilaginosa and the arbuscular mycorrhizal fungi Glomus mosseae and Gigaspora rosea (2003) Soil Biology and Biochemistry, 35, pp. 701-707
- Fracchia, S., Sampedro, I., Scervino, J.M., Garcia-Romera, I., Godeas, A.M., Ocampo, J.A., Influence of saprobe fungi and its exudates on arbuscular mycorrhizal symbiosis (2004) Plant and Soil Symbiosis, 36, pp. 169-182
- Hattori, M., Huang, X.L., Che, Q.M., Kawata, Y., Tezuka, Y., Kikuchi, T., Namba, T., 6-Hydroxykaempferol and its glycosides from Carthamus tinctorius petals (1992) Phytochemistry, 31, pp. 4001-4004
- Horie, T., Kobayashi, T., Kawamura, Y., Yoshida, I., Tominaga, H., Yamashita, K., Studies of the selective O-alkylation and dealkylation of flavonoids XVIII. A convenient method for synthesizing 3,5,6,7-tetrahydroxyflavones (1995) Bulletin of the Chemical Society of Japan, 68, pp. 2033-2041
- Jerzmanowska, Z.I., Michalska, M., Preparation of some polyhydroxy flavones (1961) Roczniki Chemii, 35, pp. 353-357
- Ma, Y.L., Van Den Heuvel, H., Claeys, M., Characterization of 3-methoxyflavones using fast-atom bombardment and collision-induced dissociation tandem mass spectrometry (1999) Rapid Communication in Mass Spectrometry, 13, pp. 1932-1942
- Mabry, T.J., Markham, K.R., Thomas, M.B., (1970) The Systematic Identification of Flavonoids, , New York: Springer
- Miyahara, M., Ohtaka, H., Katayama, H., Tatsumi, Y., Miyaichi, Y., Tomimori, T., Structure-activity relationship of flavonoids in suppressing rat liver lipid peroxidation (1993) Yakugaku Zasshi, 113, pp. 133-154
- Nagao, M., Morita, N., Yahagi, T., Shimizu, M., Kuroyanagi, M., Fukuoka, M., Yoshihara, K., Sugimura, T., Mutagenicities of 61 flavonoids and 11 related compounds (1981) Environmental Mutagenesis, 3, pp. 401-419
- Ponce, M.A., Scervino, J.M., Erra-Balsells, R., Ocampo, J.A., Godeas, A.M., Flavonoids isolated from shoots, roots and roots exudates of Brassica alba (2004) Phytochemistry, , (submitted)
- Poulin, M.J., Bel-Rhlid, R., Piche, Y., Chenevert, R., Flavonoids released by carrot (Daucus carota) seedlings stimulate hyphal development of vesicular-arbuscular mycorrhizal fungi in the presence of optimal CO2 enrichment (1993) Journal of Chemical Ecology, 19, pp. 2317-2327
- Robin, V., Irurzun, A., Amoros, M., Boustie, J., Carrasco, L., Antipoliovirus flavonoids from Psiadia dentata (2001) Antiviral Chemistry and Chemotherapy, 12, pp. 283-291
- Serra-Bonvehi, J., Ventura-Coll, F., Escola-Jorda, R., The composition, active components and bacteriostatic activity of propolis in diets (1994) Journal of the American Oil Chemists Society, 71, pp. 529-532
- Stevens, J.F., Wollenweber, E., Ivancic, M., Hsu, V.L., Sundberg, S., Deinzer, M.L., Leaf surface flavonoids of Chrysothamnus (1999) Phytochemistry, 51, pp. 771-780
- (1996) The Wiley Registry of Mass Spectral Data, 1996, Sixth Ed., , Wiley, New York
- Valant-Vetschera, K.M., Wollenweber, E., Comparative analysis of leaf exudate flavonoids in Achillea subsect. Filipendulinae (1996) Biochemical Systematics and Ecology, 24, pp. 435-446
- Wagner, H., Hoerhammer, L., Hitzler, G., Farkas, L., Total synthesis of vogeletin, a flavonol from Tephrosia vogeli (1965) Tetrahedron Letters, (43), pp. 3849-3850
- Wollenweber, E., Schober, I., Dostal, P., Hradetzky, D., Arriaga-Giner, F.J., Yatskievych, G., Flavonoids and terpenoids from the exudates of some Baccharis species (1986) Zeitschrift fur Naturforschung C-A Journal of Biosciences, 41, pp. 87-93
- Wollenweber, E., Doerr, M., Exudate flavonoids in some Solanaceae (1995) Biochemical Systematics and Ecology, 23, pp. 457-458
- Wollenweber, E., Dorr, M., Fritz, H., Papendieck, S., Yatskievych, G., Roitman, J.N., Exudate flavonoids in Asteraceae from Arizona, California, and Mexico (1997) Zeitschrift fur Naturforschung C-A Journal of Biosciences, 52, pp. 301-307
- Wollenweber, E., Doerr, M., Fritz, H., Valant-Vetschera, K.M., Exudate flavonoids in several Asteroideae and Cichorioideae (1998) Zeitschrift fur Naturforschung C-A Journal of Biosciences, 53, p. 937
- Zhu, H.-Y., Zhang, C.-M., Liu, F.-C., Synthesis of 3,4′-dimethoxykaempferol (2000) Hecheng Huaxue Bianjibu, 8, pp. 284-286
Citas:
---------- APA ----------
Ponce, M.A., Scervino, J.M., Erra-Balsells, R., Ocampo, J.A. & Godeas, A.M.
(2004)
. Flavonoids from shoots and roots of Trifolium repens (white clover) grown in presence or absence of the arbuscular mycorrhizal fungus Glomus intraradices. Phytochemistry, 65(13), 1925-1930.
http://dx.doi.org/10.1016/j.phytochem.2004.06.005---------- CHICAGO ----------
Ponce, M.A., Scervino, J.M., Erra-Balsells, R., Ocampo, J.A., Godeas, A.M.
"Flavonoids from shoots and roots of Trifolium repens (white clover) grown in presence or absence of the arbuscular mycorrhizal fungus Glomus intraradices"
. Phytochemistry 65, no. 13
(2004) : 1925-1930.
http://dx.doi.org/10.1016/j.phytochem.2004.06.005---------- MLA ----------
Ponce, M.A., Scervino, J.M., Erra-Balsells, R., Ocampo, J.A., Godeas, A.M.
"Flavonoids from shoots and roots of Trifolium repens (white clover) grown in presence or absence of the arbuscular mycorrhizal fungus Glomus intraradices"
. Phytochemistry, vol. 65, no. 13, 2004, pp. 1925-1930.
http://dx.doi.org/10.1016/j.phytochem.2004.06.005---------- VANCOUVER ----------
Ponce, M.A., Scervino, J.M., Erra-Balsells, R., Ocampo, J.A., Godeas, A.M. Flavonoids from shoots and roots of Trifolium repens (white clover) grown in presence or absence of the arbuscular mycorrhizal fungus Glomus intraradices. Phytochemistry. 2004;65(13):1925-1930.
http://dx.doi.org/10.1016/j.phytochem.2004.06.005