Chemical Constituents of Curculigo orchioides
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CHEMICAL CONSTITUENTS OF Curculigo orchioides
Chao Niu, Zhen-Zhen Zhang, Lan-Ping Yang, Yang-Yang Zhai, Sheng-Nan Li, Shuang-Ying Hao, Xing-Ying Chen, Jun-Hua Wang, and Zhen-Hui Wang*
Curculigo orchioides Gaertn., belonging to the Hypoxidaceae family in the Pharmacopoeia of China, is widely distributed in Japan, China, Australia, Malaya, and India. Phytochemical and pharmacological studies on the species of the genus have previously been reported [1–4]. Its rhizomes, named “Xian-Mao” in traditional Chinese medicine, have been used for treatment of bone metabolism disorder, osteoporosis, cold sperm, impotence, jaundice, numbness of the limbs, enuresis, decline in physical strength, asthma, and cold pain of back and knee [5]. In our continuous efforts to explore potential active ingredients from this plant, 12 compounds were isolated from the Curculigo genus. Among them, compounds 9–12 were obtained from the Amaryllidaceae family for the first time. The structures of compounds 1–12 were identified by comparison of the experimental and reported physicochemical data. Extraction and Isolation. The air-dried and powdered rhizomes of Curculigo orchioides Gaertn. (10 kg) were extracted thrice each with 100 L 95% EtOH under reflux conditions for 3 h. The extracts were combined and evaporated, and the aqueous residue (310 g) was suspended in H2O (3.0 L) and partitioned with petroleum ether (PE, 60–90°C, 3 × 3.0 L), CHCl3 (3 × 3.0 L), and EtOAc (3 × 3.0 L) successively to yield a PE-soluble fraction (20.5 g), a CHCl3-soluble fraction (32.1g), and an EtOAc-soluble fraction (46.6 g). The EtOAc-soluble fraction (40 g) was subjected to column chromatography (CC) on silica gel (7.0 × 120 cm, 280 g) using stepwise gradient elution by CHCl3–MeOH (100:0, 1 L), (95:5, 7 L), (90:10, 7 L), (80:20, 15 L), (70:30, 15 L), (50:50, 10 L), and (0:100, 3 L) to give 35 fractions (Frs. 1–35). Fraction 12 (4.7 g) was resubjected to CC (silica gel, gradient of CHCl3–EtOAc, 80:20–0:100) to give Fr. D. Fraction D was separated by CC (ODS, MeOH–H2O, 1:5, MeOH–H2O, 1:1) to give compounds 1–3 and 6–9. Fraction D was further subjected to preparative reversed-phase HPLC (MeOH–H2O, 10:1 to 1:1, flow rate 2.5 mL/min, wavelength 203 nm) to obtain compounds 4, 5, and 10–12. Compounds 1–12 were identified as orcinol glucoside B (1), orcinol-1-O-β-D-apiofuranosyl-(1→6)-β -Dglucopyranoside (2), anacardoside (3), curculigoside (4), curculigoside B (5), curculigoside C (6), curculigoside G (7), glucosyringic acid (8), benzyl-O-β-D-glucopyranoside (9), p-hydroxycinnamic acid (10), 3,5-dihydroxy-4-methoxybenzoic acid (11), and levoglucosan (12) by comparison of their 1H and 13C NMR data with the spectroscopic data reported in the literature. Orcinol Glucoside B (1). White needle crystals, C15H20O8. 1H NMR (600 MHz, CD3OD, δ, ppm, J/Hz): 2.06 (3H, s, CH3-5), 2.22 (3H, s, CH3-8′), 3.35–3.63 (4H, m, H-2′, 3′, 4′, 5′), 4.81 (1H, d, J = 7.4, H-1′), 6.30 (1H, s, H-6), 6.33 (1H, s, H-2), 6.39 (1H, s, H-4). 13C NMR (150 MHz, CD3OD, δ, ppm): 141.1 (C-1), 109.7 (C-2), 159.
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