Chemical Constituents of the Flowers of Sophora davidii
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CHEMICAL CONSTITUENTS OF THE FLOWERS OF Sophora davidii
Pengfei Yang, Jing Yang, Shen Huang, Tao Wei, and Duobin Mao*
Sophora davidii (France.) Pavol., also known as Sophora viciifolia Hance, is a deciduous shrub that occurs on hill slopes and sandy places at an altitude of 2000–3500 m high. In China, it is mainly distributed in Hubei, Sichuan, Henan, and Yunnan Provinces. Its flowers, roots, leaves, and fruits are widely used as folk medicine to cure fever, pharyngitis, cystitis, hypertension, dysentery, etc. [1]. Modern pharmacological research has demonstrated that it possesses antitumor [2], anti-inflammatory [3], antiallergic [3], and antioxidant [4] activities. In our investigation of the bioactive compounds from Sophora davidii, we report the isolation and structural identification of eight molecules from its flowers, and all the compounds were isolated from the genus Sophora for the first time. The flowers of S. davidii were collected from Yiliang City, Yunnan Province, P. R. China in October 2018 and authenticated by Assoc. Prof. Shen Huang. A voucher specimen was deposited at the Department of Plant Resources, School of Food and Bioengineering, Zhengzhou University of Light Industry, P. R. China. Dried flowers of S. davidii (10 kg) were extracted three times with 80% EtOH, and all of the EtOH solution was evaporated under reduced pressure. The dark brown residue was fractionated sequentially by petroleum ether, EtOAc, and n-BuOH. The obtained n-BuOH-soluble extract was subjected to column chromatography with HP-20 macroporous absorption resins, Sephadex LH-20, and ODS-C18 to generate 10 fractions (Frs. C3-1–C3-10), of which Fr. C3-8 was purified by reverse semipreparative HPLC to afford compounds 1 (7 mg), 2 (12 mg), 3 (5 mg), 4 (8 mg), and 5 (10 mg). Compound 6 (3 mg) was obtained from Fr. C3-6 using MeOH–H2O–AcOH (65:35:0.1) as the mobile phase at 3 mL/min. Compounds 7 (6 mg) and 8 (6 mg) were purified by semipreparative RP-HPLC from Fr. C3-4. The structures of all compounds were elucidated by spectroscopic analyses and comparison with the reported literature values. (7R,7′R,8S,8′S)-Neoolivil-9-O-β -D-glucopyranoside (1), amorphous yellow powder. 1 H NMR (600 MHz, DMSO-d6, δ, ppm, J/Hz): 6.99 (1H, d, J = 2.4, H-2), 6.96 (1H, d, J = 2.4, H-2′), 6.85 (1H, dd, J = 8.4, 2.4, H-6), 6.80 (1H, dd, J = 8.4, 2.4, H-6′), 6.76 (1H, d, J = 8.4, H-5′), 6.76 (1H, d, J = 8.4, H-5), 4.94 (1H, m, H-7), 4.86 (1H, m, H-7′), 4.18 (1H, m, H-1′′), 3.91 (1H, m, H-9), 3.80 (6H, s, 3, 3′-OCH3), 3.67 (1H, m, H-9′), 3.55 (1H, m, H-9), 3.45 (1H, m, H-9′), 2.33 (1H, m, H-8), 2.14 (1H, m, H-8′). 13C NMR (150 MHz, DMSO-d6, δ, ppm): 134.3 (C-1), 110.4 (C-2), 147.5 (C-3), 145.8 (C-4), 115.3 (C-5), 118.9 (C-6), 82.0 (C-7), 50.5 (C-8), 69.0 (C-9), 134.4 (C-1′), 110.5 (C-2′), 147.5 (C-3′), 145.7 (C-4′), 115.2 (C-5′), 118.7 (C-6′), 81.9 (C-7′), 53.5 (C-8′), 60.1 (C-9′), 55.8 (2, 2′-OCH3) 103.4 (C-1′′), 73.8 (C-2′′), 77.0 (C-3′′), 70.2 (C-4′′), 77.1 (C-5′′), 61.1 (C-6′′) [5]. (7R,7′R,8S,8′S)-Neoolivil-4-O-β -D-glucopyranoside (2), amorpho
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