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Aromatic compounds from an aqueous extract of "ban lan gen" and their antiviral activities.

ABSTRACT: A pair of new diphenyl glycerol ether enantiomers (-)-1 and (+)-1 and two new methyl benzamidobenzoates 2 and 3, named (-)-(R)- and (+)-(S)-isatindigotrioic acid [(-)-1 and (+)-1] and isatindigoticamides A (2) and B (3), respectively, were isolated from an aqueous decoction of the roots of Isatis indigotica (ban lan gen). Their structures were elucidated by spectroscopic data analysis including 2D NMR experiments. The absolute configurations of (-)-1 and (+)-1 were assigned based on the CD exciton chirality method. Compounds 2 and 3 exhibited antiviral activities against HSV-1 with IC50 values of 4.87 and 25.87 ?mol/L, respectively. Compound 2 was also found active against Coxsackie virus B3 and LPS-induced NO production.

SUBMITTER: Liu Y

PROVIDER: S-EPMC5343108 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature

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Aromatic compounds from an aqueous extract of "ban lan gen" and their antiviral activities.

Liu Yufeng Y Chen Minghua M Guo Qinglan Q Li Yuhuan Y Jiang Jiandong J Shi Jiangong J

Acta pharmaceutica Sinica. B 20161108 2

A pair of new diphenyl glycerol ether enantiomers (-)-1 and (+)-1 and two new methyl benzamidobenzoates 2 and 3, named (-)-(R)- and (+)-(S)-isatindigotrioic acid [(-)-1 and (+)-1] and isatindigoticamides A (2) and B (3), respectively, were isolated from an aqueous decoction of the roots of Isatis indigotica (ban lan gen). Their structures were elucidated by spectroscopic data analysis including 2D NMR experiments. The a ...[more]

PMID: 28303224

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Project description:Our group previously demonstrated that Caesalpinia mimosoides Lamk exhibits many profound biological properties, including anticancer, antibacterial, and antioxidant activities. However, its antiviral activity has not yet been investigated. Here, the aqueous extract of C. mimosoides was prepared from the aerial parts (leaves, stalks, and trunks) to see whether it exerts anti-influenza (H1N1) effects and to reduce the organic solvents consumed during extraction, making it a desirable approach for the large-scale production for medical uses. Our plant extract was quantified to contain 7 g of gallic acid (GA) per 100 g of a dry sample, as determined using HPLC analysis. It also exerts potent antioxidant activities comparable to those of authentic GA. According to untargeted metabolomics (UPLC-ESI(-)-QTOF-MS/MS) with the aid of cheminformatics tools (MetFrag (version 2.1), SIRIUS (version 5.8.3), CSI:FingerID (version 4.8), and CANOPUS), the major metabolite was best annotated as "gallic acid", phenolics (e.g., quinic acid, shikimic acid, and protocatechuic acid), sugar derivatives, and dicarboxylic acids were deduced from this plant species for the first time. The aqueous plant extract efficiently inhibited an influenza A (H1N1) virus infection of MDCK cells with an IC50 of 5.14 µg/mL. Of equal importance, hemolytic activity was absent for this plant extract, signifying its applicability as a safe antiviral agent. Molecular docking suggested that GA interacts with conserved residues (e.g., Arg152 and Asp151) located in the catalytic inner shell of the viral neuraminidase (NA), sharing the same pocket as those of anti-neuraminidase drugs, such as laninamivir and oseltamivir. Additionally, other metabolites were also found to potentially interact with the active site and the hydrophobic 430-cavity of the viral surface protein, suggesting a possibly synergistic effect of various phytochemicals. Therefore, the C. mimosoides aqueous extract may be a good candidate for coping with increasing influenza virus resistance to existing antivirals.

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Aromatic compounds from an aqueous extract of "ban lan gen" and their antiviral activities.

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Aromatic compounds from an aqueous extract of "ban lan gen" and their antiviral activities.

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