101. Anti-inflammatory coumarins with short- and long-chain hydrophobic groups from roots of Angelica dahurica cv. Hangbaizhi.
- Author
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Wei, Wei, Wu, Xiu-Wen, Deng, Gai-Gai, and Yang, Xiu-Wei
- Subjects
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ANTI-inflammatory agents , *COUMARINS , *HYDROPHOBIC interactions , *PLANT roots , *ANGELICA (Plants) - Abstract
The 1 H NMR-guided fractionation of a cyclohexane soluble portion of the 75% ethanolic extract of the roots of Angelica dahurica cv. Hangbaizhi led to the isolation of two coumarins, namely, 5-(3″-hydroxy-3″-methylbutyl)-8-hydroxyfuranocoumarin, and isobyakangelicin hydrate-3″-ethyl ether, and ten coumarins with short- or long-chain hydrophobic groups, namely, andafocoumarins A–J. Their structures were elucidated by extensive spectroscopic analyses. The absolute configurations of the C-2″ secondary alcohols in ten of these compounds were deduced via the circular dichroism data of the in situ formed [Rh 2 (OCOCF 3 ) 4 ] complex, and oxidation reactions were utilized to determine location of the double bonds in the lipid chain of andafocoumarins H and I, respectively. The long-chain hydrophobic group of andafocoumarin J was determined by the method of chemical degradation and GC–MS analysis. It was the first time that coumarins with short- or long-chain hydrophobic groups in this plant had been comprehensively investigated. All isolates were assayed for their inhibitory effect against nitric oxide (NO) production in a lipopolysaccharide (LPS)-activated RAW264.7 macrophage cell line, among which andafocoumarins A and B exhibited a potent inhibition on LPS-activated NO production with IC 50 values of 19.7 and 13.9 μM, respectively, indicating their stronger inhibitory activity than l -N 6 -(1-iminoethyl)-lysine (IC 50 = 23.7 μM), a selective inhibitor of inducible nitric oxide synthase. [ABSTRACT FROM AUTHOR]
- Published
- 2016
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