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Molecules 2017, 22(12), 2107; doi:10.3390/molecules22122107

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

1
Key Laboratory of Bio-Pesticide and Chemistry-Biology, Ministry of Education, Fujian Agriculture and Forestry University, Fuzhou 350002, China
2
Key Laboratory of Plant Virology of Fujian Province, Institute of Plant Virology, Fujian Agriculture and Forestry University, Fuzhou 350002, China
*
Authors to whom correspondence should be addressed.
Received: 2 November 2017 / Revised: 21 November 2017 / Accepted: 29 November 2017 / Published: 4 December 2017
(This article belongs to the Section Natural Products)
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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-β-d-glucopyranosyl)phenyl]propionamide (1), 2-hydroxy-N-[(2-O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl)phenyl]propionamide (2), 2β-carboxyl-piperidine-4β-acetic acid methyl ester (4), and 4-hydroxyphenyl-1-O-[6-(hydrogen-3-hydroxy-3-methylpentanedioate)]-β-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), β-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. View Full-Text
Keywords: Ailanthus altissima; Simaroubaceae; phenylpropionamide; piperidine; phenols; flavonoid; Tobacco mosaic virus (TMV) Ailanthus altissima; Simaroubaceae; phenylpropionamide; piperidine; phenols; flavonoid; Tobacco mosaic virus (TMV)
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Ni, J.-C.; Shi, J.-T.; Tan, Q.-W.; Chen, Q.-J. Phenylpropionamides, Piperidine, and Phenolic Derivatives from the Fruit of Ailanthus altissima. Molecules 2017, 22, 2107.

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