Two new phenanthrene glucosides, named 2'-hydroxy-4,4',7'-trimethoxy-1,1'-biphenanthrene-2,7-di-O-β-D-glucoside (1) and 1-(4-hydroxybenzyl)-4-methoxy-2,7-dihydroxy-phenanthrene-8-O-β-D-glucoside (2), together with three known compounds were isolated from the tubers of Cremastra appendiculata (D.Don) Makino. Their structures were elucidated on the basis of spectral data. Compounds 1-4 showed moderate cytotoxic activity and compound 5 showed weak cytotoxic activity against the two cell lines tested. This is the first reported occurrence of an unusual biphenanthrene glucoside in this plant.
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.
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