Chemical Constituents of the Ginseng Cordyceps Medicinal Fungal Substance (II)
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CHEMICAL CONSTITUENTS OF THE GINSENG CORDYCEPS MEDICINAL FUNGAL SUBSTANCE (II)
Lin Wang, Han Gao, Ying Xin Gao, Xue Qing Yang, Zhi Dong Qiu,* and Wei Xu*
Ginseng is one of the most widely used traditional Chinese medicines. With related reports, ginseng has a wide range of therapeutic and pharmacological effects [1, 2]. Saponins are the main active ingredient of ginseng [3]. Findings from previous studies reveal that, compared with nonfermented ginseng, the composition of fermented ginseng changes greatly [4]. Our research group has studied the fermentation of ginseng of Cordyceps sinensis; 14 triterpenoid saponins were isolated [5]. In further research we continued to use ginseng as raw material for the preparation of ginseng cordyceps fungal substance (GCFS) by solid state fermentation. During the exploration of the biologically active components of GCFS, six triterpenoid saponins were isolated. All the chemical components were isolated from GCFS for the first time. The dried GCFS (4.0 kg) was powdered and extracted with 70% EtOH (40 L × 4, 2 h for each time) at 80°C. After removal of EtOH under reduced pressure, the extract was suspended in H2O (4 L), and then successively partitioned with petroleum ether, EtOAc, and n-BuOH. The n-BuOH fraction (303 g) was subjected to D101 macroporous resin column chromatography, eluting with a step gradient solvent system H2O–EtOH; 50% the EtOH fraction was loaded onto an MCI-gel column eluting with a step gradient solvent system H2O–EtOH and open ODS using a step gradient of MeOH–H2O, then purified by semi-prep. HPLC to afford compounds 1 (94.2 mg), 2 (6.2 mg), 3 (8.5 mg), 4 (23.7 mg), 5 (3.8 mg), and 6 (3.8 mg). Notoginsenoside R2 (1). C41H72O13, white amorphous powder. ESI-MS m/z 793.50 [M + Na]+. 1H NMR (600 MHz, C5 D5N, δ, ppm, J/Hz): 0.82 (3H, s, Me-30), 0.98 (3H, s, Me-19), 1.18 (3H, s, Me-18), 1.41 (3H, s, Me-21), 1.48 (3H, s, Me-29), 1.65 (3H, s, Me-27), 1.68 (3H, s, Me-26), 2.10 (3H, s, Me-28), 4.34 (1H, d, J = 7.8, H-6), 4.96 (1H, d, J = 7.2, H-1′), 5.78 (1H, d, J = 6.6, H-1′′), 5.35 (1H, t, J = 6.6, H-24). 13C NMR (150 MHz, C5D5N, δ, ppm) data were identical to those reported in the literature [6]. 20-(S)-Ginsenoside Rf (2). C42H72O14, white amorphous powder. ESI-MS m/z 822.51 [M + Na]+. 1H NMR (600 MHz, C5D5N, δ, ppm, J/Hz): 0.82 (3H, s, Me-30), 0.97 (3H, s, Me-19), 1.17 (3H, s, Me-18), 1.41 (3H, s, Me-21), 1.48 (3H, s, Me-29), 1.65 (3H, s, Me-27), 1.68 (3H, s, Me-26), 2.10 (3H, s, Me-28), 4.30–4.33 (1H, m, H-6), 4.93 (1H, d, J = 7.2, H-1′), 5.93 (1H, d, J = 7.8, H-1′). 13C NMR (150 MHz, C5D5N, δ, ppm) data were identical to those reported in the literature [7, 8]. Gypenoside-XVII (3). C48H82O18, white amorphous powder. ESI-MS m/z 969.60 [M + Na]+. 1H NMR (600 MHz, C5 D5N, δ, ppm, J/Hz): 0.83 (3H, s, Me-19), 0.98 (3H, s, Me-30), 0.98 (3H, s, Me-18), 1.12 (3H, s, Me-29), 1.30 (3H, s, Me-28), 1.62 (3H, s, Me-26), 1.67 (3H, s, Me-21), 1.67 (3H, s, Me-27), 3.27 (1H, dd, J = 4.2, 12.0, H-3), 4.93 (1H, d, J = 7.8, H-1′), 5.11 (1H, d, J = 7.8, H-1′′), 5.14 (1H, d, J =
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