Journal
BIOCHEMICAL SYSTEMATICS AND ECOLOGY
Volume 37, Issue 4, Pages 245-253Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bse.2009.03.010
Keywords
Lolium multiflorum Lam; Poaceae; Italian rye grass; Neotyphodium sp; Glomus intraradices; Flavonoids; Phenolic acids
Funding
- UBA [UBACyTX028]
- CONICET [PIP5003]
- ANCYPT [PICT 13404]
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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-hydroxy8-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-dimetlioxy-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. (C) 2009 Elsevier Ltd. All rights reserved.
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