Chemical Constituents from the Aerial Parts of Agastache rugosa and Their Inhibitory Activities on Prostaglandin E-2 Production in Lipopolysaccharide-Treated RAW 264.7 Macrophages

Abstract

A new flavone glucoside, acacetin-7-O-(3 ''-O-acety1-6 ''-O-malonyl)-beta-D-glucopyranoside (1), two new phenolic glucosides, (3R,7R)-tuberonic acid-12-O-[6'-O-(E)feruloyl]-beta-D-glucopyranoside (14) and salicylic acid-2-O-[6'-O-(E)-feruloyl]-beta-D-n-glucopyranoside (15), and two new phenylpropanoid glucosides, chavicol-1-O-(6'-O-methylmalonyl)-beta-D-glucopyranoside (17) and chavicol-1-O-(6'-O-acetyl)-beta-D-glucopyranoside(18), as well as 26 known compounds, 2-13, 16, and 19-31, were isolated from the aerial parts of Agastache rugose. The structures of the new compounds were established by spectroscopic/spectrometric methods such as HRESIMS, NMR, and ECD. The anti-inflammatory effect of the isolated compounds was evaluated by measuring their inhibitory activities on prostaglandin E-2 (PGE(2)) in lipopolysaccharide (LPS)-treated RAW 264.7 macrophages. New compounds 1, 15, 17, and 18 inhibited LPS-induced PGE2 production with IC50 values of 16.8 +/- 0.8, 33.9 +/- 4.8, 14.3 +/- 2.1, and 48.8 +/- 4.4 mu M, respectively. Compounds 5, 7, 9-11, 13, 19, 20, 22, and 27-30 showed potent inhibitory activities with IC50 values of 1.7-8.4 mu M.