Flavonoids, benzoic acids and cinnamic acids isolated from shoots and roots of Italian ryegrass (Lolium multiflorum Lam.) with and without endophyte association and arbuscular mycorrhizal fungus

PONCE, MA; BOMPADRE, M.J.; SCERVINO, JM; OCAMPO, JA; CHANETON, E.J.; GODEAS, A.M.

BIOCHEMICAL SYSTEMATICS AND ECOLOGY

Elsevier

Lugar: Amsterdam; Año: 2009 vol. 37 p. 245 - 253

0305-1978

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 (Lmþ) and without (Lm_) endophyte association, grown with (Micþ) 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), 20,7-dihydroxyflavone (12), 20,3,50,7,8-pentahydroxyflavone (13), 30,40-dihydroxy-3-methoxyflavone (14), 3,40-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.