Anti-Inflammatory Triterpenoids from the Caulophyllum robustum Maximin LPS-Stimulated RAW264.7 Cells

Abstract

Caulophyllum robustum Maxim is widely distributed in China and used as a traditional herbal medicine to induce childbirth, ease the pain of labor, rectify delayed or irregular menstruation, alleviate heavy bleeding and pain during menstruation, and treat external injuries and irregular menses. According to our detailed chemical investigation, three new triterpene derivatives (1–3), together with seven known compounds, were isolated from the root and rhizome of C. robustum Maxim. Their structures were elucidated by 1D- and 2D-NMR spectroscopic analysis and physio-chemical methods. They were identified as (1) 23-hydroxy-3,19-dioxo-olean-12-en-28-oic-acid; (2) 23-hydroxy-3,11-dioxo-olean-12-en-28-oic acid; and (3) 16α,23-dihydroxy-3-oxo-olean-12-en-28-oic acid. Compounds (1–10) inhibited the LPS-activated NO production in RAW264.7 cells. Furthermore, the anti-inflammatory characteristics of these compounds were confirmed on the basis of decreases in iNOS and NF-κB protein expression in RAW264.7 cells.

Chemical Constituents from the Roots of Polygala arillata and Their Anti-Inflammatory Activities

“…. It is white powder; for 1 H-NMR, 13 C-NMR, and DEPT-135 spectroscopic data, see Table 1 and Figures Figure S7 (Supplementary Materials).…”

“…As a result, a new compound, named arillatanoside E, which was elucidated as 3-O-β-D-glucopyranosyl presenegenin 28-O-β-D-xylopyranosyl-(1 ⟶ 3)-β-D-xylopyranosyl-(1 ⟶ 4)-α-L-rhamnopyranosyl-(1 ⟶ 2)-(4-O-acetyl)-β-D-fucopyranosyl ester, along with 11 known compounds was isolated from the ethanolic extract of the roots of P. arillata. e other 11 known compounds were identified as oleanolic acid (2) [3], 3′-E-3,4,5-trimethoxy cinnamoyl-6-benzoyl sucrose (3) [4], trans-ferulic acid (4) [5], trans-feruloyl-glucoside (5) [6], feruloyl-glucoside (6) [6], 2,4,6-trimethoxy-1-O-β-D-glycoside (7) [7], 3-methoxy-4hydroxybenzoic acid (8) [8], monopentadecanoin (9) [9], sinapic acid (10) [10], p-hydroxybenzaldehyde (11) [11], and palmitic acid (12) [12] by means of mass spectrometry (MS), ultraviolet spectrophotometry (UV), and nuclear magnetic resonance (NMR) spectroscopy, including 1D-NMR and 2D-NMR, such as 1 H-NMR, 13 C-NMR, HSQC, HMBC, and 1 H-1 H COSY.…”

“…NO is a short-lived free radical and is synthesized by NO synthase (NOS). ree different isoforms of NOS exist and are referred to as neuronal NOS (nNOS), inducible NOS (iNOS), and endothelial NOS (eNOS) [13]. Lipopolysaccharides (LPS) are constituents of the cell walls of Gram-negative bacteria and act as the activator of the immune system.…”

“…Lipopolysaccharides (LPS) are constituents of the cell walls of Gram-negative bacteria and act as the activator of the immune system. LPS-stimulated macrophages induce the expression of iNOS, which stimulates NO production [13].…”

“…NO plays a key role in the regulation of cytokines especially related to inflammation and has anti-inflammatory with cytotoxic effects in inflammatory reaction [13,14]. In this case, by measuring the amount of NO produced by mouse macrophages, we can screen out the compounds with anti-inflammatory activity in P. arillata [15].…”