ABSTRACT
Two new quinones, 4-(5-hydroxy-1,4-dioxo-1,4-dihydronaphtha-len-3-ylamino)-butyric acid methyl ester (compound 1) and 1,3-dimethoxycarbonyl-8-hydroxy-9,10-anthraquinone (2), and six known compounds (3-8) were isolated from the roots of Juglans mandshurica Maxim., a member of the Juglandaceae family. The chemical structures of the compounds were elucidated by nuclear magnetic resonance spectroscopy and compared with data from the literature. The isolated compounds were evaluated for their ability to inhibit the production of nitric oxide, tumour necrosis factor-α, and interleukin-6 by the mouse macrophage RAW 264.7 cell line after lipopolysaccharide stimulation in vitro. We found that compounds 1-4 exhibited potent anti-inflammatory effects, as indicated by suppression of lipopolysaccharide-stimulated nitric oxide and cytokine production with 50% inhibitory concentrations between 20.09 µM and 27.63 µM. These results identify two novel quinones from J. mandshurica with potential utility as anti-inflammatory compounds.
Subject(s)
Juglans , Animals , Anti-Inflammatory Agents/pharmacology , Juglans/chemistry , Lipopolysaccharides/pharmacology , Mice , Molecular Structure , Nitric Oxide , Plant Extracts/chemistry , Quinones/pharmacologyABSTRACT
Sanguisorba officinalis L. is a traditional herbal plant that belongs to the genus Sanguisorba and the family Rosaceae. A new ursane-type triterpenoid, 3-oxo-urs-11, 13(18)-dien-19, 28-olide (1), two known ursane-type triterpenoids (3 - 4) and three known oleanane-type triterpenoids (2, 5 - 6) were isolated from the roots of S. officinalis by silica gel column and MPLC. Their structures were identified by interpretation of spectroscopic data (1 D NMR, 2 D NMR, HR-ESI-MS) and comparison with those reported in the literature. Compound 2 was isolated from the Rosaceae family, compounds 3-5 were obtained from the genus Sanguisorba, and compound 6 was obtained from the S. officinalis for the first time. Additionally, all of the isolated compounds were evaluated for their cytotoxic activity against three human cancer cells. Compound 3 showed better cytotoxic activity against A549, HeLa, SK-Hep1 cells than the other compounds with IC50 values of 48.58 ± 1.88, 47.84 ± 2.01, 42.31 ± 2.43 µM, respectively.