Flavonoids, benzoic acids and cinnamic acids isolated from shoots and roots of Italian rye grass (Lolium multiflorum Lam.) with and without endophyte association and arbuscular mycorrhizal fungus
Phenolic compounds present in Lolium multiflorum Lam. were isolated and characterized. Significant differences in their distribution were found, in shoots and roots of plants with (Lm+) and without (Lm-) endophyte association, grown with (Mic+) and without (Mic-) mycorrhizal fungi Glomus intraradice...
Guardado en:
| Autor principal: | |
|---|---|
| Otros Autores: | , , , , |
| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
2009
|
| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
| Aporte de: | Registro referencial: Solicitar el recurso aquí |
| LEADER | 13009caa a22011537a 4500 | ||
|---|---|---|---|
| 001 | PAPER-8461 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203816.0 | ||
| 008 | 190411s2009 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-69649088656 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a BSECB | ||
| 100 | 1 | |a Ponce, M.A. | |
| 245 | 1 | 0 | |a Flavonoids, benzoic acids and cinnamic acids isolated from shoots and roots of Italian rye grass (Lolium multiflorum Lam.) with and without endophyte association and arbuscular mycorrhizal fungus |
| 260 | |c 2009 | ||
| 270 | 1 | 0 | |m Ponce, M.A.; CIHIDECAR-CONICET, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Pabellon II, 3P Ciudad Universitaria, 1428 Buenos Aires, Argentina; email: henryh@qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a van Acker, F.A.A., Hageman, J.A., Haenen, G.R.M.M., van der Vijgh, W.J.F., Bast, A., Menge, W.M.P.B., Synthesis of novel 3,7-substituted-2-(3′,4′-dihydroxyphenyl) flavones with improved antioxidant activity (2000) J. Med. Chem., 43, pp. 3752-3760 | ||
| 504 | |a Bécard, G., Douds, D.D., Pfeffer, P.E., Extensive in vitro hyphal growth of vesicular-arbuscular mycorrhizal fungi in presence of CO2 and flavonols (1992) Appl. Environ. Microbiol., 58, pp. 821-825 | ||
| 504 | |a Bel Rhlid, R., Chabot, S., Piché, Y., Chénevert, R., Isolation and identification of flavonoids from Ri T-DNA-transformed rots (Daucus carota) and their significance in vesicular-arbuscular mycorrhiza (1993) Phytochemistry, 33, pp. 1369-1371 | ||
| 504 | |a Chabot, S., Bel-Rhlid, T., Chenevert, R., Piche, Y., Hyphae growth promotion in vitro of the VA mycorrhizal fungus, Gigaspora margarita Becker & Hall, by the activity of structurally specific flavonoid compounds under CO2-enriched conditions (1992) New Phytol, 122, pp. 461-467 | ||
| 504 | |a Devi, M.C., Reddy, M.N., Phenolic acid metabolism of groundnut (Arachis hypogea L.) plants inoculated with fungus and Rhizobium (2002) Plant Growth Regul, 37, pp. 151-156 | ||
| 504 | |a Friend, J., Phenolic substances and plant disease (1985) Annu. Proc. Phytochem. Soc. Eur., 25, pp. 367-392 | ||
| 504 | |a Grael, C.F.F., Albuquerque, S., Lopes, L.C., Chemical constituents of Lychnophra pohlii and trypanocidal activity of crude plant extracts and of isolated compounds (2005) Fitoterapia, 76, pp. 73-82 | ||
| 504 | |a Guo, B.J., Hendrix, J.W., An, Z.-Q., Ferriss, R.S., Role of Acremonium endophyte of fescue on inhibition of colonization and reproduction of mycorrhizal fungi (1992) Mycologia, 84, pp. 882-885 | ||
| 504 | |a Hammerschmidt, R., Phytoalexins: what have we learned after 60 years? (1999) Annu. Rev. Phytopathol, 37, pp. 285-306 | ||
| 504 | |a Harper, J.K., Arif, A.M., Ford, E.J., Strobel, G.A., Porco Jr., J.A., Tomer, D.P., Oneill, K.L., Grant, D.M., Pestacin: a 1,3-dihydro isobenzofuran from Pestalotiopsis microspora possessing antioxidant and antimycotic activities (2003) Tetrahedron, 59, pp. 2471-2476 | ||
| 504 | |a Jiang, H., Yang, X., Zhang, D., Xu, L., Yang, S., Zou, Z., Chemical constituents of Siphonostegia chinensis (2003) Zhongguo Yaoxue Zazhi, 38, pp. 97-99 | ||
| 504 | |a Krishnamachari, V., Levine, L.H., Zhou, C., Pare, P.W., In vitro flavon-3-ol oxidation mediated by a B ring hydroxylation pattern (2004) Chem. Res. Toxicol, 17, pp. 795-804 | ||
| 504 | |a Ling Lee, M., Chilvers, G.A., Ash Ford, A.E., A histochemical study of phenolic materials in mycorrhizae and uninfected roots of Eucalyptus fastigata Deana and Maiden (1977) New Phytol, 78, pp. 313-328 | ||
| 504 | |a Lynn, D.J., Chang, M., Phenolic signals in cohabitation: implication for plant development. Annu. Rev. Plant Physiol (1990) Plant Mol. Biol., 41, pp. 497-526 | ||
| 504 | |a Martin, F., Gonzalez Vila, F.J., Fulvic acids from particulate matter of a water-logged peatland (1988) Chem. Geol., 67, pp. 353-358 | ||
| 504 | |a Mayer, A.M., Resistance to herbivores and fungal pathogens: variations on a common theme? A review comparing the effect of secondary metabolites, induced and constitutive, on herbivores and fungal pathogens. Israel J (2004) Plant Sci., 52, pp. 279-292 | ||
| 504 | |a Müller, J., Artificial infection by endophytes affects growth and mycorrhizal colonization of Lolium perenne (2003) Funct. Plant Biol., 30, pp. 419-424 | ||
| 504 | |a Negoro, T., Tanaka, T., Taketomo, H., Fujita, Y., Yano, K., Oxidation of benzyl alcohols with tetraalkylammonium dichlorobromate (1). Wakayama Daigaku Kyoikugakubu Kiyo (2003) Shizen Kagaku, 53, pp. 7-18 | ||
| 504 | |a Novas, M.V., Cabral, D., Godeas, A., Interaction between mycophyllas and mycorrhizas in Bromus setifolius from Patagonia, Argentina (2005) Symbiosis, 42, pp. 23-30 | ||
| 504 | |a Omacini, M., Chaneton, E.J., Ghersa, C.M., Neotyphodium in cool-season grasses (2005) A Hierarchical Framework for Understanding the Ecosystem Consequences of Endophyte-Grass Symbiosis, pp. 141-161. , Roberts C., West C., and Spiers D. (Eds), Blackwell Publishing, UK | ||
| 504 | |a Park, Y., Moon, B., Lee, E., Lee, Y., Yoon, Y., Ahn, J., Lim, Y., Spectral assignments and reference data: 1H- and 13C-NMR data of hydroxyflavone derivatives (2007) Magn. Reson. Chem., 45, pp. 674-679 | ||
| 504 | |a 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 (2004) Phytochemistry, 65, pp. 1925-1930 | ||
| 504 | |a Rigano, D., Apostolides, A.N., Bruno, M., Formisano, C., Grassia, A., Piacente, S., Piozzi, F., Senatore, F., Phenolic compounds of Marrubium globosum ssp. libanoticum from Lebanon (2006) Biochem. Syst. Ecol, 34, pp. 256-258 | ||
| 504 | |a Sargenti, S.R., Vichnewski, W., Sonication and liquid chromatography as a rapid technique for extraction and fractionation of plant material (2000) Phytochem. Anal, 11, pp. 69-73 | ||
| 504 | |a Scervino, J.M., Ponce, M.A., Erra-Bassells, R., Bompadre, M.J., Vierheilig, H., Ocampo, J.A., Godeas, A.M., Glycosidation of apigenin results in a loss of its activity on different growth parameters of arbuscular mycorrhizal fungi from the genus Glomus and Gigaspora (2006) Soil Biol. Biochem, 38, pp. 2919-2922 | ||
| 504 | |a Shaw, L.J., Morris, P., Hooker, J.E., Perception and modification of plant flavonoid signals by rhizosphere microorganisms (2006) Environ. Microbiol., 8 (11), pp. 1867-1880 | ||
| 504 | |a Siqueira, J.O., Nair, M.G., Hammerschmidt, R., Safir, G.R., Significance of phenolic compounds in plant-soil-microbial systems (1991) Crit. Rev. Plant Sci., 10, pp. 63-121 | ||
| 504 | |a Siqueira, J., Safir, G., Nair, M., Stimulation of vesicular-arbuscular mycorrhiza formation and growth of white clover by flavonoid compounds (1991) New Phytol, 118, pp. 87-93 | ||
| 504 | |a Smith, S.E., Read, D.J., Mycorrhizal Symbiosis (1997) The role of mycorrhizas in ecosystems, p. 433. , Elsevier Eds, Academic Press, San Diego, CA. pp | ||
| 504 | |a Souleman, A.A.M., Barakat, H.H., Hussein, S.A.M., El-Mousallamy, A.M.D., Nawwar, M.A.M., Unique phenolic sulphate conjugates from the flowers of Tamarix amplexicaulis (1998) Nat. Prod. Sci., 4, pp. 245-252 | ||
| 504 | |a Strobel, G., Ford, E., Worapong, J., Harper, J.K., Arif, A.M., Grant, D.M., Fung, P.C.W., Ming Wah Chau, R., Isopestacin, an isobenzofuranone from Pestalotiopsis microspora, possessing antifungal and antioxidant activities (2002) Phytochemistry, 60, pp. 179-183 | ||
| 504 | |a Suemori, A., Nakajima, K., Kurane, R., Nakamura, Y., Production of 3,4-dihydroxyphthalate from phthalate by a membrane-bound two enzyme system from Rhodococcus erythropolis (1995) Appl. Microbiol. Biot, 43, pp. 470-472 | ||
| 504 | |a Tachibana, S., Sumimoto, M., Studies on pitch troubles caused by pulping and bleaching of tropical woods. XI. Chemical conversion of butin during bleaching processes (1982) Mokuzai Gakkaishi, 28, pp. 45-58 | ||
| 504 | |a Van Etten, H., Mansfield, J.W., Bailey, J.A., Farmer, E.E., Two classes of plant antibiotics: phytoalexins versus "phytoanticipins" (1994) Plant Cell, 6, pp. 1191-1192 | ||
| 504 | |a Vila-Aiub, M.M., Ghersa, C.M., Carceller, M., Effect of herbicide diclofop-methyl on proton extrusion from Lolium multiflorum seedlings differing in resistance and in fungal endophyte (Neotyphodium sp.) infection (2003) Physiol. Plant, 119, pp. 429-439 | ||
| 504 | |a Zhang, H.W., Song, Y.C., Tan, R.H., Biology and chemistry of endophytes (2006) Nat. Prod. Rep, 23, pp. 753-771 | ||
| 520 | 3 | |a Phenolic compounds present in Lolium multiflorum Lam. were isolated and characterized. Significant differences in their distribution were found, in shoots and roots of plants with (Lm+) and without (Lm-) endophyte association, grown with (Mic+) and without (Mic-) mycorrhizal fungi Glomus intraradices, indicating a systemic effect of these microorganisms on the phenolics metabolism of L. multiflorum. We report the isolation of eight new flavonoids 7,8-dihydroxy-2-(4-hydroxyphenyl)-5-methoxy-4H-1-benzopyran-4-one (1), 3,7-dihydroxy-8-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one (2), 7,8-dihydroxy-2-(2,4-dihydroxyphenyl)-4H-1-benzopyran-4-one (3), 3,7-dihydroxy-2-(4,5-dihydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one (4), 5,6-dihydroxy-2-(4-hydroxyphenyl)-3-methoxy-4H-1-benzopyran-4-one (5), 7-hydroxy-8-methoxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (6), 3,7,8-trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (7) and 7,8-dihydroxy-2-(2,3-dihydroxyphenyl)-4H-1-benzopyran-4-one (8), and two new benzoic acids 2-hydroxy-4-methoxy-1,3-benzenedicarboxylic acid (9) and 3,6-dimethoxy-2-hydroxy-benzoic acid (10), found with the known deoxykaempferol (11), 2′,7-dihydroxyflavone (12), 2′,3,5′,7,8-pentahydroxyflavone (13), 3′,4′-dihydroxy-3-methoxyflavone (14), 3,4′-dihydroxy-3-methoxyflavone (15), galangin (16), gentisic acid (17), isoferulic acid (18), 4-hydroxy-1,2,3-benzenetricarboxylic acid (19), 3,4-dihydroxyphthalic acid (20), 2,5-dimethoxy-benzoic acid (21), p-methoxicinnamic acid (22) and 2,4-dimethoxyisophthalic acid (23). Compounds 11, 12, 13, 14, 15, 18, 20, 21 and 23, have not been isolated from plants before. © 2009 Elsevier Ltd. All rights reserved. |l eng | |
| 536 | |a Detalles de la financiación: PICT 13404 | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas, PIP5003 | ||
| 536 | |a Detalles de la financiación: This work was supported partially by UBA (UBACyT X028), CONICET (PIP5003) and ANCYPT (PICT 13404). J.M. Scervino, E.J. Chaneton and A.M. Godeas are research members of CIC (CONICET). We are grateful to E.A. Hughes for the proofreading of this manuscript. | ||
| 593 | |a CIHIDECAR-CONICET, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Pabellon II, 3P Ciudad Universitaria, 1428 Buenos Aires, Argentina | ||
| 593 | |a Departamento de Biodiversidad y Biología Experimental, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellon II, 4P Ciudad Universitaria, 1428 Buenos Aires, Argentina | ||
| 593 | |a Estación Experimental de Zaidin, CSIC, 18008 Granada, Spain | ||
| 593 | |a IFEVA, Facultad de Agronomía, Universidad de Buenos Aires, 1417 Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a FLAVONOIDS |
| 690 | 1 | 0 | |a GLOMUS INTRARADICES |
| 690 | 1 | 0 | |a ITALIAN RYE GRASS |
| 690 | 1 | 0 | |a LOLIUM MULTIFLORUM LAM |
| 690 | 1 | 0 | |a NEOTYPHODIUM SP |
| 690 | 1 | 0 | |a PHENOLIC ACIDS |
| 690 | 1 | 0 | |a POACEAE |
| 690 | 1 | 0 | |a ARBUSCULAR MYCORRHIZA |
| 690 | 1 | 0 | |a BIOCHEMISTRY |
| 690 | 1 | 0 | |a ENDOPHYTE |
| 690 | 1 | 0 | |a FUNGUS |
| 690 | 1 | 0 | |a GRASS |
| 690 | 1 | 0 | |a ORGANIC ACID |
| 690 | 1 | 0 | |a PHENOLIC COMPOUND |
| 690 | 1 | 0 | |a ROOT |
| 690 | 1 | 0 | |a SHOOT |
| 690 | 1 | 0 | |a ARBUSCULAR |
| 690 | 1 | 0 | |a FUNGI |
| 690 | 1 | 0 | |a GLOMUS INTRARADICES |
| 690 | 1 | 0 | |a LOLIUM |
| 690 | 1 | 0 | |a LOLIUM MULTIFLORUM |
| 690 | 1 | 0 | |a NEOTYPHODIUM |
| 690 | 1 | 0 | |a POACEAE |
| 690 | 1 | 0 | |a SECALE CEREALE |
| 700 | 1 | |a Bompadre, M.J. | |
| 700 | 1 | |a Scervino, J.M. | |
| 700 | 1 | |a Ocampo, J.A. | |
| 700 | 1 | |a Chaneton, E.J. | |
| 700 | 1 | |a Godeas, A.M. | |
| 773 | 0 | |d 2009 |g v. 37 |h pp. 245-253 |k n. 4 |p Biochem. Syst. Ecol. |x 03051978 |w (AR-BaUEN)CENRE-813 |t Biochemical Systematics and Ecology | |
| 856 | 4 | 1 | |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-69649088656&doi=10.1016%2fj.bse.2009.03.010&partnerID=40&md5=bccf999d295a6258d2a655c76bf961f8 |y Registro en Scopus |
| 856 | 4 | 0 | |u https://doi.org/10.1016/j.bse.2009.03.010 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_03051978_v37_n4_p245_Ponce |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03051978_v37_n4_p245_Ponce |y Registro en la Biblioteca Digital |
| 961 | |a paper_03051978_v37_n4_p245_Ponce |b paper |c PE | ||
| 962 | |a info:eu-repo/semantics/article |a info:ar-repo/semantics/artículo |b info:eu-repo/semantics/publishedVersion | ||
| 963 | |a VARI | ||
| 999 | |c 69414 | ||