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.
Highlights
Caulophyllum robustum is a perennial herb in the family Berberidaceae, whichis well known as Hong Mao Qi in Chinese [1]
As part of our effort to search for novel triterpene from C. robustum Maxim, we report here the isolation and structure determination of the three new terpenoids: (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 (Figure 1)
We report seven known other compounds: (4) collinsonin; (5) hederagenin; (6) echinocystic acid 3-O-α-L-arabinopyranoside; (7) saponin PE; (8) 3-O-α-L-arabinopyranosylgypsogenin-28-O-α-L-rhamnopyranosyl-(1-4)-β-D-glucopyranosyl-(1-6)β-D-glucopyranosyl ester; (9) 3-O-β-D-glucopyranosylgypsogenin-28-O-α-L-arabinopyranosyl-(1-6)β-D-glucopyranosyl ester, (10) 3-O-α-L-arabinopyransylgypsogenin-28-O-α-L-rhamnopyranosyl-(1-4)β-D-glucopyranosyl-(1-6)-β-D-glucopyranosylester
Summary
Caulophyllum robustum is a perennial herb in the family Berberidaceae, whichis well known as Hong Mao Qi in Chinese [1]. It is distributed in the northeast Tibet, Hubei provinces of China, native communities of North America, Its root and rhizome have beenused to induce childbirth, ease the pain of labor, rectify delayed or irregular menstruation, alleviate heavy bleeding and pain during menstruation [2]. As part of our effort to search for novel triterpene from C. robustum Maxim, we report here the isolation and structure determination of the three new terpenoids: (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 (Figure 1). (8) 3-O-α-L-arabinopyranosylgypsogenin-28-O-α-L-rhamnopyranosyl-(1-4)-β-D-glucopyranosyl-(1-6)β-D-glucopyranosyl ester; (9) 3-O-β-D-glucopyranosylgypsogenin-28-O-α-L-arabinopyranosyl-(1-6)β-D-glucopyranosyl ester, (10) 3-O-α-L-arabinopyransylgypsogenin-28-O-α-L-rhamnopyranosyl-(1-4)β-D-glucopyranosyl-(1-6)-β-D-glucopyranosylester.
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