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Bioactive thionic compounds and aromatic glycosides from Ligusticum chuanxiong.

ABSTRACT: Three new thionic compounds, (S)-2-(2-carboxyl-2-hydroxyethylthio)-ferulic acid (1), (E)-2-methoxy-4-(3-(methylsulfonyl)prop-1-en-1-yl)phenol (2), and thiosenkyunolide C (3), together with two new aromatic glycosides (4 and 5) were isolated from the rhizome of Ligusticum chuanxiong Hort. Two known compounds (6 and 7) were also obtained. Their structures were elucidated based on extensive spectroscopic data (UV, IR, 1D and 2D NMR, and HR-ESI-MS). Furthermore the absolute configurations were established by comparison of their calculated and experimental circular dichroism spectra and by a dimolybdenum tetraacetate [Mo2(AcO)4]-induced circular dichroism procedure. All compounds were evaluated against lipopolysaccharide (LPS)-induced NO production in BV2 cells, and compounds 4 and 5 showed strong inhibitory activities with IC50 values of 2.03 and 3.09 µmol/L, respectively (positive control curcumin, IC50 = 6.17 µmol/L). In addition, compound 1 showed weak proteintyrosine phosphatase-1B (PTP1B) inhibitory activity.

SUBMITTER: Zhang X 

PROVIDER: S-EPMC6147803 | biostudies-other | 2018 Sep

REPOSITORIES: biostudies-other

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Bioactive thionic compounds and aromatic glycosides from <i>Ligusticum chuanxiong</i>.

Zhang Xu X   Han Bing B   Feng Ziming Z   Jiang Jianshuang J   Yang Yanan Y   Zhang Peicheng P  

Acta pharmaceutica Sinica. B 20180411 5

Three new thionic compounds, (<i>S</i>)-2-(2-carboxyl-2-hydroxyethylthio)-ferulic acid (<b>1</b>), (<i>E</i>)-2-methoxy-4-(3-(methylsulfonyl)prop-1-en-1-yl)phenol (<b>2</b>), and thiosenkyunolide C (<b>3</b>), together with two new aromatic glycosides (<b>4</b> and <b>5</b>) were isolated from the rhizome of <i>Ligusticum chuanxiong</i> Hort. Two known compounds (<b>6</b> and <b>7</b>) were also obtained. Their structures were elucidated based on extensive spectroscopic data (UV, IR, 1D and 2D N  ...[more]

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