Chemical Constituents of Sophora tonkinensis
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CHEMICAL CONSTITUENTS OF Sophora tonkinensis
Wei Zhang,1,2 Xin Wei,1* Li-Yan Zhang,1 Xin-Yue Hu,1,2 Yong-Qiang Zhou,1 and Ying Zhou1*
The roots of Sophora tonkinensis Gagnep., named “Shan Dou Gen” in Traditional Chinese Medicine, historically have been applied as a treatment for respiratory diseases by the Miao people of Guizhou Province, China [1]. Previous studies on S. tonkinensis showed flavonoids and isoflavones as their main components with anti-inflammatory, antioxidant, and antiviral activities [2–4]. In our ongoing search for novel and bioactive compounds from folk medicinal plants [5, 6], a detail chemical investigation of the dried roots of S. tonkinensis was carried out. As a result, eight compounds were isolated and identified on the basis of extensive spectral methods, among which compounds 1, 2, and 3 were isolated from S. tonkinensis for the first time. S. tonkinensis was purchased from Guizhou Sanli Pharmaceutical Co., Ltd., Guizhou Province, China, on March 2019 and identified by Prof. Sheng-Hua Wei from Guizhou University of Traditional Chinese Medicine. A voucher specimen (No. WX_20190301) was deposited in Guizhou University of Traditional Chinese Medicine. The air-dried and powdered roots of S. tonkinensis (5 kg) were extracted with MeOH (50 L × 3) under reflux conditions at 70°C, two hours each time. After removing the organic solvent, the extract (649.1 g) was subjected to silica gel column chromatography (CHCl3–MeOH, 1:0–0:1) to afford nine fractions (Frs. A–I). Fraction B (19.28 g) was subjected to column chromatography on silica gel (petroleum ether–EtOAc, 8:1–0:1), Sephadex LH-20 (MeOH), and MCI (MeOH–H2O, 3:7–1:0) and then purified by semi-preparative HPLC using a C18 column (MeOH–H2O, 3:7–1:0) to afford compounds 1 (7.0 mg), 2 (2.0 mg), 3 (19.8 mg), 4 (10.2 mg), 5 (1.9 mg), 6 (11.6 mg), 7 (4.01 mg), and 8 (2.3 mg). 3,4-Dimethoxybenzeneacrylic acid methyl ester (1), white amorphous powder. (+)-ESI-MS m/z 245 [M + Na]+. 1H NMR (600 MHz, CD OD, δ, ppm, J/Hz): 7.66 (1H, d, J = 16.0, H-γ), 7.24 (1H, d, J = 2.0, H-2), 7.20 (1H, dd, J = 2.0, 8.3, 3 H-6), 7.01 (1H, d, J = 8.3, H-5), 6.44 (1H, d, J = 16.0, H-β), 3.89 (6H, s, 3, 4-OCH3), 3.80 (3H, s, COOCH3). 13C NMR (150 MHz, CD3OD, δ, ppm): 127.4 (C-1), 110.1 (C-2), 151.4 (C-3), 149.3 (C-4), 111.2 (C-5), 122.7 (C-6), 114.8 (C-β), 145.1 (C-γ), 50.8 (COOCH3), 55.1 (3-OCH3), 55.2 (4-OCH3), 168.3 (COOCH3) [7]. Pisatin (2), white amorphous powder. (+)-ESI-MS m/z 337 [M + Na]+. 1H NMR (600 MHz, CD3OD, δ, ppm, J/Hz): 7.37 (1H, d, J = 8.6, H-5), 6.86 (1H, s, H-6′), 6.66 (1H, dd, J = 8.6, 2.5, H-6), 6.46 (1H, d, J = 2.5, H-8), 6.39 (1H, s, H-3′), 5.94, 5.91 (each 1H, d, J = 1.0, H-2′′), 5.25 (1H, s, H-4), 4.15, 4.00 (each 1H, d, J = 11.5, H-2), 3.79 (3H, s, OCH 3). 13C NMR (150 MHz, CD3 OD, δ, ppm): 54.5 (OCH3 ), 69.3 (C-2), 76.3 (C-3), 84.6 (C-4), 131.8 (C-5), 108.8 (C-6), 161.1 (C-7), 101.0 (C-8), 156.0 (C-9), 112.6 (C-10), 119.3 (C-1′), 154.4 (C-2′), 93.2 (C-3′), 149.7 (C-4′), 142.3 (C-5′), 103.0 (C-6′), 101.4 (C-2′′) [8]. Medicarpin (3), yellow po
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