Neoflavonoids and the cinnamylphenol kuhlmannistyrene from Machaerium kuhlmannii and M. Nictitans |
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Authors: | W.David Ollis Brian T. Redman Richard J. Roberts Ian O. Sutherland Otto R. Gottlieb Mauro T. Magalhaães |
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Affiliation: | 1. Department of Chemistry, The University, Sheffield S3 7HF, England;2. Instituto de Química, Universidade de São Paulo, c.p. 20780, São Paulo, Brazil;3. Centro de Tecnologia Agrícola e Alimentar, EMBRAPA, Rio de Janeiro, Brasil |
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Abstract: | The trunkwood of Machaerium kuhlmannii contains methyl palmitate, 3-O-acetyloleanolic acid and sitosterol; the benzene derivatives 2,3-dimethoxyphenol, 2,6-dimethoxyphenol, 2-hydroxy-3-methoxyphenol, 2,3-dimethoxybenzaldehyde and methyl 3-(2-hydroxy-4-methoxyphenyl)-propionate; the isoflavonoids formononetin and (6aS,11aS)-medicarpin; the neoflavonoids (R)-3,4-dimethoxydalbergione, (R)-3,4-dimethoxydalbergiquinol, kuhlmanniquinol [(R)-3-(4-hydroxyphenyl)-3-(5-hydroxy-2,3,4-trimethoxyphenyl)-propene], dalbergin, kuhlmannin (6-hydroxy-7,8-dimethoxy-4-phenylcoumarin) and kuhlmannene (6-hydroxy-7,8-dimethoxy-4-phenylchrom-3-ene), as well as the cinnamylphenol kuhlmannistyrene [Z-1-(5-hydroxy-2,3,4-trimethoxybenzyl)-2-(2-hydroxyphenyl)-ethylene]. Five of these compounds, in addition to (R)-4′-hydroxy-3,4-dimethoxydalbergione, were also isolated from a trunkwood extract of M. nictitans. Structural assignments were confirmed by chemical interconversion and by the synthesis of (±)-kuhlmanniquinol. |
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Keywords: | Leguminosae-Lotoideae cinnamylphenol neoflavonoids isoflavonoids methyl dihydrocinnamate phenols. |
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