Phytochemical investigation of bioactive constituents from Angelica sinensis.

摘要

The dried root of Angelica sinensis (Oliv.) Diels (Dong Quai or Dang Gui) has been used for centuries as a women's tonic for alleviating PMS, menstrual cramps, and symptoms related to menopause. In this project, a series of analytical techniques involving the examination of macroscopic, microscopic features, as well as HPTLC and HPLC fingerprint profiles were established and validated for botanical identification of Angelica sinensis. In the four different plant materials, sample 1 (BC 165) and sample 2 (BC 167) were verified as Angelica sinensis.; 5-HT7 receptor binding assay-directed fractionation of a methanol extract of Angelica sinensis led to the isolation of 23 compounds. By using spectroscopic approaches such as UV, IR, HRMS, MS-MS, 1D and 2D NMR, as well as X-ray experiments, six new compounds of gelispirolide (5 ), 10-angeloylbutylphthalide (6), sinaspirolide ( 7), ansaspirolide (8), angediligustilide (9), angeliferulate (11), together with 17 known compounds including five phthalides (1-4, 13), a coumarin (14), five polyynes (19-23), and others (10, 12, 15-18) were identified. Compounds 12, 14, 20-23 were isolated for the first time from A. sinensis.; All of the isolates (1-23) were evaluated for competitive binding activity in the 5-HT7 receptor and GABAa assays. In the 5-HT 7 assay, Z-butylidenephthalide (2), p-hydroxyphenethyl trans-ferulate (10), falcarindiol (19), 9Z,17-octadecadiene-12,14-diyne-1,11,16-triol, 1-acetate (20), and 8-hydroxy-1-methoxy-, Z-9-heptadecene-4,6-diyn-3-one (23) exhibited weak inhibitory effects on [3H) LSD binding to the 5-HT7 receptor with IC50 values of 126.7 muM, 47.6 muM, 117.5 muM, 118.1 muM, and 44.3 muM, respectively. In the GABAa assay, riligustilide (4), gelispirolide ( 5), and imperatorin (14) exhibited an inhibitory effect on the binding of [3H] diazepam to the GABAa receptor with IC50 values of 24 muM, 29 muM, and 21 muM, respectively. In addition, in an in vitro anti-TB assay, falcarindiol ( 19), 9Z,17-octadecadiene-12,14-diyne-1,11,16-triol, 1-acetate (20) exhibited potent activities with MIC values of 6.0 mug/ml and 1.4 mug/ml vs Erdman strain, 26.7 mug/ml and 25.3 mug/ml vs H37Rv strain, respectively.; The findings will be helpful for quality control of crude extracts and products of A. sinensis.