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Anti-Inflammatory Phenolic Acid Esters from the Roots and Rhizomes of Notopterygium incisium and Their Permeability in the Human Caco-2 Monolayer Cell Model

Authors :
Shi-Lin Yang
Hong-Ning Liu
Yan-Fang Yang
You-Bo Zhang
Guoyue Zhong
Wei Wei
Xiu-Wen Wu
Wei Xu
Xiu-Wei Yang
Source :
Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry, Molecules; Volume 22; Issue 6; Pages: 935, Molecules, Vol 22, Iss 6, p 935 (2017)
Publication Year :
2017
Publisher :
MDPI, 2017.

Abstract

A new ferulic acid ester named 4-methyl-3-trans-hexenylferulate (1), together with eight known phenolic acid esters (2-9), was isolated from the methanolic extract of the roots and rhizomes of Notopterygium incisium. Their structures were elucidated by extensive spectroscopic techniques, including 2D NMR spectroscopy and mass spectrometry. 4-Methoxyphenethyl ferulate (8) NMR data is reported here for the first time. The uptake and transepithelial transport of the isolated compounds 1-9 were investigated in the human intestinal Caco-2 cell monolayer model. Compounds 2 and 6 were assigned for the well-absorbed compounds, compound 8 was assigned for the moderately absorbed compound, and compounds 1, 3, 4, 5, 7, and 9 were assigned for the poorly absorbed compounds. Moreover, all of the isolated compounds were assayed for the inhibitory effects against nitric oxide (NO) production in the lipopolysaccharide-activated RAW264.7 macrophages model and L-N⁶-(1-iminoethyl)-lysine (L-NIL) was used as a positive control. Compounds 1, 5, 8, and 9 exhibited potent inhibitory activity on NO production with the half maximal inhibitory concentration (IC50) values of 1.01, 4.63, 2.47, and 2.73 μM, respectively, which were more effective than L-NIL with IC50 values of 9.37 μM. These findings not only enriched the types of anti-inflammatory compounds in N. incisum but also provided some useful information for predicting their oral bioavailability and their suitability as drug leads or promising anti-inflammatory agents.

Details

Language :
English
ISSN :
14203049
Volume :
22
Issue :
6
Database :
OpenAIRE
Journal :
Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry
Accession number :
edsair.doi.dedup.....5705b74c433c1a2047a483bcf0e3c87e