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Phenylpropionamides, Piperidine, and Phenolic Derivatives from the Fruit of Ailanthus altissima.

ABSTRACT: Four novel compounds-two phenylpropionamides, one piperidine, and one phenolic derivatives-were isolated and identified from the fruit of a medicinal plant, Ailanthus altissima (Mill.) Swingle (Simaroubaceae), together with one known phenylpropionamide, 13 known phenols, and 10 flavonoids. The structures of the new compounds were elucidated as 2-hydroxy-N-[(2-O-?-d-glucopyranosyl)phenyl]propionamide (1), 2-hydroxy-N-[(2-O-?-d-glucopyranosyl-(1?6)-?-d-glucopyranosyl)phenyl]propionamide (2), 2?-carboxyl-piperidine-4?-acetic acid methyl ester (4), and 4-hydroxyphenyl-1-O-[6-(hydrogen-3-hydroxy-3-methylpentanedioate)]-?-d-glucopyranoside (5) based on spectroscopic analysis. All the isolated compounds were evaluated for their inhibitory activity against Tobacco mosaic virus (TMV) using the leaf-disc method. Among the compounds isolated, arbutin (6), ?-d-glucopyranosyl-(1?6)-arbutin (7), 4-methoxyphenylacetic acid (10), and corilagin (18) showed moderate inhibition against TMV with IC50 values of 0.49, 0.51, 0.27, and 0.45 mM, respectively.

SUBMITTER: Ni JC 

PROVIDER: S-EPMC6149757 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature

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Phenylpropionamides, Piperidine, and Phenolic Derivatives from the Fruit of Ailanthus altissima.

Ni Jian-Cheng JC   Shi Jian-Ting JT   Tan Qing-Wei QW   Chen Qi-Jian QJ  

Molecules (Basel, Switzerland) 20171204 12

Four novel compounds-two phenylpropionamides, one piperidine, and one phenolic derivatives-were isolated and identified from the fruit of a medicinal plant, <i>Ailanthus altissima</i> (Mill.) Swingle (Simaroubaceae), together with one known phenylpropionamide, 13 known phenols, and 10 flavonoids. The structures of the new compounds were elucidated as 2-hydroxy-<i>N</i>-[(2-<i>O</i>-β-d-glucopyranosyl)phenyl]propionamide (<b>1</b>), 2-hydroxy-<i>N</i>-[(2-<i>O</i>-β-d-glucopyranosyl-(1→6)-β-d-glu  ...[more]

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