Chemical constituents from rhizomes of Cimicifuga dahurica / 中草药

To isolate and identify the chemical constituents from the rhizome of Cimicifuga dahurica. Methods The isolation and purification of 60% EtOH extract of the rhizomes of C. dahurica were carried out through various modern chromatographic separation techniques: HP-20, silica gel, ODS, Sephadex LH-20 column and semi-preparative HPLC. And the structures of the compounds were identified based on spectroscopic data and physicochemical properties. Results Twenty compounds were isolated and identified as cimicifugaside F (1), (+) (2S,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-[(β-D-glucopyranosyloxy) methyl]-7-methoxybenzofuran-5-propenoic acid (2), 5-hydroxy-2-methoxybenzoic acid (3), benzoic acid 4-O-β-D-glucoside (4), isoferulic acid (5), ferulic acid (6), trans-ferulic acid 4-O-β-D-allopyranoside (7), trans-ferulic acid 4-O-β-D-glucoside (8), (E)-sinapic acid 4-O-β-D-glucoside (9), 6,6’-di-O-sinapoylsurcose (10), piscidic acid (11), fukinolic acid (12), N-trans-feruloyltyramine 4-O-β-D-allopyranoside (13), N-trans-3’-methoxy-4’-feruloyltyramine-4-O-β-D-allopyranoside (14), N-trans-3’-methoxy-4’- feruloyltyramine-4-O-β-D-glucoside (15), grevilloside G (16), (-)-syringaresinol (17), (-)-syringaresinol 4,4’-di-O-β-D- allopyranoside (18), (+)-isolarisiresinol 3a-O-β-D-glucoside (19), (-)-5’-methoxyisolariciresinol 3a-O-β-D-glucoside (20). Conclusion Compound 1 was identified as a new lignan, and compounds 2-4, 8-10, 15-17 and 20 were isolated from Cimicifuga genus for the first time.

Isolation and Identification of Chemical Constituents of Phenolic Acid from Cimicifuga dahurica / 中国实验方剂学杂志

Objective: Cimicifuga dahurica (Ranunculaceae) has many bioactivities. Although there have been intensive studies for saponin constituents at present, only a few studies have focused on for chemical constituents of phenolic acid. To define the phenolic acid constituents,C. dahurica was separated, and the structures of the compounds were identified,in the expectation of providing a basis for its further development,utilization and quality control. Method: A total of 16 kg rhizome of C. dahurica was extracted with 70%ethanol for three times by heating reflux. These 3 extracts were decompressed and concentrated,and then dissolved in water. Then the solvent was successively extracted with petroleum ether,ethyl acetate(EtOAc) and n-butanol(BuOH). The components of EtOAc and water extract were isolated and purified by macroporous,silica gel,ODS,Sephadex LH-20 column chromatography,preparative HPLC and recrystallization,and the structures were identified by nuclear magnetic resonance(NMR) and physicochemical analysis etc. Result: Fifteen compounds were isolated from the ethyl acetate and water fractions,and identified as cimicifugic G (1),2-caffeoyl piscidic acid (2),cimicifugic A (3),cimicifugic B (4),caffeic acid 3-O-β-D-glucopyranoside (5),cimicifugic E (6),cimicifugic F (7),trans-ferulic acid 4-O-β-D-glucopyranoside (8),carboxymethyl isoferulate (9),3,4-dimethoxycinnamic acid (10),ethyl ferulate (11),caffeic ester glucoside (12),shomaside A (13),isoferulic acid (14),caffeic acid (15). Conclusion: Compounds 1-7,9-10,13 were isolated from the plant for the first time.

Chemical constituents from rhizomes of Cimicifuga dahurica / 中草药

Objective To study the chemical constituents from the rhizomes of Cimicifuga dahurica. Methods The chemical constituents from the rhizomes of C. dahurica in ethyl acetate extraction phase and H2O fraction were isolated and purified by chromatographic methods, such as silica gel, opening ODS column, Sephadex LH-20, ODS and semi-preparative HPLC. Which stucture were identified by NMR and physicochemical analysis. Results Fifteen compounds were isolated and identified as 20(R),23 (R),24(R),25(S),26(S)-16β:23; 23:26; 24:25-triepoxy-12β-acetoxy-3β,26-dihydroxy-9,19-cyclolanost-7-ene-3-O-β- D-xylopyranoside (1), cimiaceroside B (2), 23-O-acetylshengmanol-3-O-β-D-xylopyranoside (3), 7,8-didehydro-24-O-acetylhydroshengmanol-3-O-β-D- xylopyranoside (4), 24-epi-cimigenol-3-O-β-D-xylopyranoside (5), 24-O-acetyldahurinol-3-O-β-D-xylopyranoside (6), 24-epi-24-O- acetylhydroshengmanol-3-O-β-D-xylopyranoside (7), 12β-O-acetylcimigenol-3-O-β-D-xylopyranoside (8), 23-O-acetyl-7,8- didehydroshengmanol-3-O-β-D-xylopyranoside (9), 7,8-didehydro-25-dehydrocimigenol-3-O-β-D-xylopyranoside (10), 25-O- ethylcimigenol-3-O-β-D-xylopyranoside (11), 3,4-dihydroxybenzoic acid (12), 24-O-acetylisodahurinol-3-O-α-L-arabinopyranoside (13), 2,3-dihydroxy-2-[(4-hydroxyphenyl) methyl]-1-ethyl ester (14), and 2,3-dihydroxy-2-[(4-hudroxyphenyl) methyl]-4-ethyl ester (15). Conclusion Compounds 6, 11-12, and 14-15 are isolated from Cimicifuga genus for the first time. Compounds 1, 4-5, 8-10, and 13 are isolated from C. dahurica for the first time.

Chemicals from Cimicifuga dahurica and Their Inhibitory Effects on Pro-inflammatory Cytokine Production by LPS-stimulated Bone Marrow-derived Dendritic Cells

Inflammation is a biological response caused by overactivation of the immune system and is controlled by immune cells via a variety of cytokines. The overproduction of pro-inflammatory cytokines enhances abnormal host immunity, resulting in diseases such as rheumatoid arthritis, cardiovascular disease, Alzheimer's disease, and cancer. Inhibiting the production of pro-inflammatory cytokines such as interleukin (IL)-12p40, IL-6, and tumor necrosis factor (TNF)-α might be one way to treat these conditions. Here, we investigated the anti-inflammatory activity of compounds isolated from Cimicifuga dahurica (Turcz.) Maxim., which is traditionally used as an antipyretic and analgesic in Korea. In primary cell culture assays, 12 compounds were found to inhibit the production of pro-inflammatory cytokines (IL-12p40, IL-6, and TNF-α) in vitro in bone marrow-derived dendritic cells stimulated with LPS.

Experimental Study on Antitumor Effects of Total Glycoside of Cimicifuga dahurica Maxim / 中国中医药信息杂志

Objective To investigate the antitumor effects of total glycoside of Cimicifuga dahurica (TGCD) in vivo and in vitro, and further explore its mechanisms. Methods The anti-tumor activity in vitro was determined by MTT assay and the anti-tumor activity in vivo was evaluated using experimental mouse tumor (S180) model and human tumor (A549) xenografts in nude mice. After treatment, A549 cell apoptosis and morphologic change were evaluated by Annexin V/PI flow cytometry and HE staining. Results Inhibitory concentration 50% (IC50) of TGCD on A549, HepG2, HL60, Eca-109 and MDA-MB231 cells were 20.3, 27.1, 21.2, 23.4 and 32.7 ?g/mL respectively. Administration of TGCD (100 or 200 mg/kg) inhibited S180 solid tumor development in mice, the inhibition rates were 42.8% and 54.6% respectively. Administration of TGCD (100 or 200 mg/kg) inhibited A549 tumor growth with a T/C (mean value of treated group/mean value of control group) value of 58.1% and 52.2% respectively. In addition, increased percentage of apoptotic cells induced by TGCD in human A549 nude mice xenografts and the histopathological changes including cell shrinkage and condensation of chromosomes were observed. Conclusion TGCD has demonstrated antitumor bioactivity both in vitro and in vivo, which may be related to its effects of inducing apoptosis activity.

Studies on chemical constituents of Cimicifuga dahurica / 中草药

Object To isolate and identify the chemical constituents from the rhizome of Cimicifuga dahurica (Turcz ) Maxim Methods The different chromatographic techniques were used to isolate ten constituents, and the spectral methods, such as IR, MS, 1HNMR, 13 CNMR and 2DNMR, were used to identify the structures Results Their structures were identified as cimigenol (Ⅰ), 24 epi 7, 8 didehydrocimigenol 3 O ? D xylopyranoside (Ⅱ), 7, 8 didehydrocimigenol 3 O ? D xylopyranoside (Ⅲ), 25 O acetyl 7, 8 didehydrocimigenol 3 O ? D xylopyranoside (Ⅳ), 3 arabinosyl 24 O acetylhydroshengmanol 15 glucoside (Ⅴ), isoferulic acid (Ⅵ), (E) 3 (3′ methyl 2′ butenylidene) 2 indolinone (Ⅶ), sucrose (Ⅷ), ? sitosterol (Ⅸ) and stigmastenol 3 O ? D glucopyranoside (Ⅹ), respectively Conclusion Compounds Ⅱ Ⅳ, Ⅹ are isolated for the first time from the title plant