[A new secoiridoid from Cornus officinalis].

Abstract

The chemical constituents from Cornus officinalis were isolated and purified by various techniques such as macroporous adsorption resin, silica gel, octadecylsilyl(ODS), Sephadex LH-20 column chromatography and preparative high-performance liquid chromatography(HPLC). The structures of the isolates were determined by a combination of spectroscopic techniques such as high-resolution electrospray ionization mass spectrometry(HR-ESI-MS), one-dimensional(1D) and two-dimensional(2D) nuclear magnetic resonance(NMR) spectroscopy. Ten compounds were isolated from the aqueous extract of C. officinalis and identified as(±)-cornuscone(1),(-)-(Z)-4-hydroxy-3-methoxyphenylpropene 4-O-β-L-xylopyranosyl-(1→6)-β-D-glucopyranoside(2), kaempferol 3-O-β-D-glucopyranoside(3), kampferol(4), myricetin(5), trifolin(6), quercetin 3-O-β-D-glucopyranoside(7), quercetin 3-O-β-D-glucuronide-6″-methyl ester(8), quercetin 3-O-β-D-glucuronide-6″-ethyl ester(9) and pyrogallol(10). Compound 1 is a new secoiridoid, named(±)-cornuscone with a rare methyl substitution at the C-1 position. The anti-inflammatory activity of 1 was evaluated in lipopolysaccharide(LPS)-induced RAW264.7 cells in mice. The results showed the median inhibition concentration(IC_(50)) of 1 was(31.15±1.29)μmol·L~(-1), which demonstrated that the anti-inflammatory activity of 1 was significantly superior to that of indomethacin [IC_(50) value of(48.32±1.66)μmol·L~(-1)].