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

Biochemical Systematics and Ecology

Volumn 37, Issue 4, 2009, Pages 245-253

  Ponce, María A ^a   Bompadre, María J ^b   Scervino, José M ^b   Ocampo, Juan A ^c   Chaneton, Enrique J ^b   Godeas, Alicia M ^b  

^a DEPARTAMENTO DE QUÍMICA ORGÁNICA   (Argentina)

^b UNIVERSIDAD DE BUENOS AIRES   (Argentina)

^c CSIC   (Spain)

Author keywords

Flavonoids; Glomus intraradices; Italian rye grass; Lolium multiflorum Lam; Neotyphodium sp; Phenolic acids; Poaceae

Indexed keywords

ARBUSCULAR MYCORRHIZA; BIOCHEMISTRY; ENDOPHYTE; FUNGUS; GRASS; ORGANIC ACID; PHENOLIC COMPOUND; ROOT; SHOOT;

ARBUSCULAR; FUNGI; GLOMUS INTRARADICES; LOLIUM; LOLIUM MULTIFLORUM; NEOTYPHODIUM; POACEAE; SECALE CEREALE;

EID: 69649088656     PISSN: 03051978     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bse.2009.03.010     Document Type: Article

References (36)

1. van Acker F.A.A., Hageman J.A., Haenen G.R.M.M., van der Vijgh W.J.F., Bast A., and Menge W.M.P.B. Synthesis of novel 3,7-substituted-2-(3′,4′-dihydroxyphenyl) flavones with improved antioxidant activity. J. Med. Chem. 43 (2000) 3752-3760
2. 2 and flavonols. Appl. Environ. Microbiol. 58 (1992) 821-825
3. Bel Rhlid R., Chabot S., Piché Y., and Chénevert R. Isolation and identification of flavonoids from Ri T-DNA-transformed rots (Daucus carota) and their significance in vesicular-arbuscular mycorrhiza. Phytochemistry 33 (1993) 1369-1371
4. 2-enriched conditions. New Phytol 122 (1992) 461-467
5. Devi M.C., and Reddy M.N. Phenolic acid metabolism of groundnut (Arachis hypogea L.) plants inoculated with fungus and Rhizobium. Plant Growth Regul 37 (2002) 151-156
6. Friend J. Phenolic substances and plant disease. Annu. Proc. Phytochem. Soc. Eur. 25 (1985) 367-392
7. Grael C.F.F., Albuquerque S., and Lopes L.C. Chemical constituents of Lychnophra pohlii and trypanocidal activity of crude plant extracts and of isolated compounds. Fitoterapia 76 (2005) 73-82
8. Guo B.J., Hendrix J.W., An Z.-Q., and Ferriss R.S. Role of Acremonium endophyte of fescue on inhibition of colonization and reproduction of mycorrhizal fungi. Mycologia 84 (1992) 882-885
9. Hammerschmidt R. Phytoalexins: what have we learned after 60 years?. Annu. Rev. Phytopathol 37 (1999) 285-306
10. Harper J.K., Arif A.M., Ford E.J., Strobel G.A., Porco Jr. J.A., Tomer D.P., Oneill K.L., Heider E.M., and Grant D.M. Pestacin: a 1,3-dihydro isobenzofuran from Pestalotiopsis microspora possessing antioxidant and antimycotic activities. Tetrahedron 59 (2003) 2471-2476
11. Jiang H., Yang X., Zhang D., Xu L., Yang S., and Zou Z. Chemical constituents of Siphonostegia chinensis. Zhongguo Yaoxue Zazhi 38 (2003) 97-99
12. Krishnamachari V., Levine L.H., Zhou C., and Pare P.W. In vitro flavon-3-ol oxidation mediated by a B ring hydroxylation pattern. Chem. Res. Toxicol 17 (2004) 795-804
13. Ling Lee M., Chilvers G.A., and Ash Ford A.E. A histochemical study of phenolic materials in mycorrhizae and uninfected roots of Eucalyptus fastigata Deana and Maiden. New Phytol 78 (1977) 313-328
14. Lynn D.J., and Chang M. Phenolic signals in cohabitation: implication for plant development. Annu. Rev. Plant Physiol. Plant Mol. Biol. 41 (1990) 497-526
15. Martin F., and Gonzalez Vila F.J. Fulvic acids from particulate matter of a water-logged peatland. Chem. Geol. 67 (1988) 353-358
16. 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. Plant Sci. 52 (2004) 279-292
17. Müller J. Artificial infection by endophytes affects growth and mycorrhizal colonization of Lolium perenne. Funct. Plant Biol. 30 (2003) 419-424
18. Negoro T., Tanaka T., Taketomo H., Fujita Y., and Yano K. Oxidation of benzyl alcohols with tetraalkylammonium dichlorobromate (1). Wakayama Daigaku Kyoikugakubu Kiyo. Shizen Kagaku 53 (2003) 7-18
19. Novas M.V., Cabral D., and Godeas A. Interaction between mycophyllas and mycorrhizas in Bromus setifolius from Patagonia, Argentina. Symbiosis 42 (2005) 23-30
20. Omacini M., Chaneton E.J., and Ghersa C.M. Neotyphodium in cool-season grasses. In: Roberts C., West C., and Spiers D. (Eds). A Hierarchical Framework for Understanding the Ecosystem Consequences of Endophyte-Grass Symbiosis (2005), Blackwell Publishing, UK 141-161
21. 13C-NMR data of hydroxyflavone derivatives. Magn. Reson. Chem. 45 (2007) 674-679
22. Ponce M.A., Scervino J.M., Erra-Balsells R., Ocampo J.A., and 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 (2004) 1925-1930
23. Rigano D., Apostolides A.N., Bruno M., Formisano C., Grassia A., Piacente S., Piozzi F., and Senatore F. Phenolic compounds of Marrubium globosum ssp. libanoticum from Lebanon. Biochem. Syst. Ecol 34 (2006) 256-258
24. Sargenti S.R., and Vichnewski W. Sonication and liquid chromatography as a rapid technique for extraction and fractionation of plant material. Phytochem. Anal 11 (2000) 69-73
25. Scervino J.M., Ponce M.A., Erra-Bassells R., Bompadre M.J., Vierheilig H., Ocampo J.A., and 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. Soil Biol. Biochem 38 (2006) 2919-2922
26. Shaw L.J., Morris P., and Hooker J.E. Perception and modification of plant flavonoid signals by rhizosphere microorganisms. Environ. Microbiol. 8 11 (2006) 1867-1880
27. Siqueira J.O., Nair M.G., Hammerschmidt R., and Safir G.R. Significance of phenolic compounds in plant-soil-microbial systems. Crit. Rev. Plant Sci. 10 (1991) 63-121
28. Siqueira J., Safir G., and Nair M. Stimulation of vesicular-arbuscular mycorrhiza formation and growth of white clover by flavonoid compounds. New Phytol 118 (1991) 87-93
29. Smith, S.E., Read, D.J., 1997. Mycorrhizal Symbiosis. In: Elsevier (Eds.), The role of mycorrhizas in ecosystems. Academic Press, San Diego, CA. pp. 433.
30. Souleman A.A.M., Barakat H.H., Hussein S.A.M., El-Mousallamy A.M.D., and Nawwar M.A.M. Unique phenolic sulphate conjugates from the flowers of Tamarix amplexicaulis. Nat. Prod. Sci. 4 (1998) 245-252
31. Strobel G., Ford E., Worapong J., Harper J.K., Arif A.M., Grant D.M., Fung P.C.W., and Ming Wah Chau R. Isopestacin, an isobenzofuranone from Pestalotiopsis microspora, possessing antifungal and antioxidant activities. Phytochemistry 60 (2002) 179-183
32. Suemori A., Nakajima K., Kurane R., and Nakamura Y. Production of 3,4-dihydroxyphthalate from phthalate by a membrane-bound two enzyme system from Rhodococcus erythropolis. Appl. Microbiol. Biot 43 (1995) 470-472
33. Tachibana S., and Sumimoto M. Studies on pitch troubles caused by pulping and bleaching of tropical woods. XI. Chemical conversion of butin during bleaching processes. Mokuzai Gakkaishi 28 (1982) 45-58
34. Van Etten H., Mansfield J.W., Bailey J.A., and Farmer E.E. Two classes of plant antibiotics: phytoalexins versus "phytoanticipins". Plant Cell 6 (1994) 1191-1192
35. Vila-Aiub M.M., Ghersa C.M., and Carceller M. Effect of herbicide diclofop-methyl on proton extrusion from Lolium multiflorum seedlings differing in resistance and in fungal endophyte (Neotyphodium sp.) infection. Physiol. Plant 119 (2003) 429-439
36. Zhang H.W., Song Y.C., and Tan R.H. Biology and chemistry of endophytes. Nat. Prod. Rep 23 (2006) 753-771