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Cimicifugoside

目录号 : GC25251

Cimicifugoside is a triterpenoid originating from the rhizomes of Cimicifuga simplex, and acts to inhibit the subcellular transport of nucleosides.

Cimicifugoside Chemical Structure

Cas No.:66176-93-0

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1mg
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产品描述

Cimicifugoside is a triterpenoid originating from the rhizomes of Cimicifuga simplex, and acts to inhibit the subcellular transport of nucleosides.

Chemical Properties

Cas No. 66176-93-0 SDF Download SDF
分子式 C37H54O11 分子量 674.82
溶解度 DMSO: 100 mg/mL (148.19 mM);Water: 100 mg/mL (148.19 mM);Ethanol: 100 mg/mL (148.19 mM) 储存条件 Store at -20°C
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1 mM 1.4819 mL 7.4094 mL 14.8188 mL
5 mM 0.2964 mL 1.4819 mL 2.9638 mL
10 mM 0.1482 mL 0.7409 mL 1.4819 mL
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Research Update

Phytoestrogen cimicifugoside-mediated inhibition of catecholamine secretion by blocking nicotinic acetylcholine receptor in bovine adrenal chromaffin cells

J Pharmacol Exp Ther 2004 May;309(2):641-9.PMID:14757852DOI:10.1124/jpet.103.062331.

We investigated the effect of the phytoestrogen Cimicifugoside, one of the pharmacologically active ingredients of the medicinal plant Cimicifuga racemosa (black cohosh) that has been used to treat many kinds of neuronal and menopausal symptoms, such as arthritis, menopausal depression, and nerve pain. Cimicifugoside inhibited calcium increase induced by 1,1-dimethyl-4-phenylpiperazinium iodide (DMPP), a nicotinic acetylcholine receptor (nAChR) agonist in bovine adrenal chromaffin cells with a half-maximal inhibitory concentration (IC(50)) of 18 +/- 2 microM. In contrast, Cimicifugoside did not affect the calcium increases evoked by high K(+), veratridine, and bradykinin. The DMPP-induced sodium increase was also inhibited by Cimicifugoside with an IC(50) of 2 +/- 0.3 microM, suggesting that the activity of nAChRs is inhibited by Cimicifugoside. Cimicifugoside did not affect the KCl-induced secretion but markedly inhibited the DMPP-induced catecholamine secretion that was monitored by carbon-fiber amperometry in real time and high-performance liquid chromatography through electrochemical detection. The results suggest that Cimicifugoside selectively inhibits nAChR-mediated response in bovine chromaffin cells.

Simultaneous determination of Cimicifugoside H-2, Cimicifugoside H-1, 23-epi-26-deoxyactein, cimigenol xyloside and 25-O-acetylcimigenoside in beagle dog plasma by LC-MS/MS

J Pharm Biomed Anal 2012 Mar 25;62:87-95.PMID:22285707DOI:10.1016/j.jpba.2011.11.029.

A selective and sensitive LC-MS/MS method was developed and validated for the simultaneous determination of five constituents (Cimicifugoside H-2, Cimicifugoside H-1, 23-epi-26-deoxyactein, cimigenol xyloside and 25-O-acetylcimigenoside) of Cimicifuga foetida L. in beagle dog plasma. The quantitation was performed on a LC-MS/MS with negative electrospray ionization in selected reaction monitoring (SRM) mode. A gradient mobile phase composed of methanol and water was used at a flow rate of 0.4 ml/min. All the analytes and internal standard (20 (S)-ginsenoside Rg3) were isolated from plasma samples by a liquid-liquid extraction method. The average extraction recoveries were 73-74% for Cimicifugoside H-2, 89-94% for Cimicifugoside H-1, 73-80% for 23-epi-26-deoxyactein, 89-91% for cimigenol xyloside, 87-96% for 25-O-acetylcimigenoside, respectively. The method showed good linearity and no endogenous material interfered with all the five compounds and I.S. peaks. The lower limit of quantification (LLOQ) of all analytes was 0.5 ng/ml. The intra- and inter-day precision of analysis was less than 15% for each analyte at concentrations of 2.0, 50, 500 ng/ml, and the accuracy ranged from 85.8% to 107%. This method was successfully applied to reveal the pharmacokinetic properties of Cimicifugoside H-2, Cimicifugoside H-1, 23-epi-26-deoxyactein, cimigenol xyloside and 25-O-acetylcimigenoside after oral administration.

The immune response of splenic lymphocytes after Cimicifugoside treatment in vitro and pretreatment in vivo

J Pharmacobiodyn 1980 Dec;3(12):643-8.PMID:7277179DOI:10.1248/bpb1978.3.643.

Pretreatment of mouse splenocytes with Shigella lipopolysaccharide and concanavalin A followed by 50 ng/ml of Cimicifugoside resulted in a 69% and 31% inhibition of blastogenesis compared to controls. The plaque forming colony assay using sheep erythrocytes (SRBC) showed a decreased number of plaque forming colonies after exposure of the splenic cells to 1 microgram/ml of Cimicifugoside. Cimicifugoside, 0.1 mg/mouse i.p. suppressed the anti-SRBC response in the plaque forming assay. The major inhibition of the antibody response occurred when Cimicifugoside was administered 1 day before the primary immunization with SRBC. The delayed type hypersensitivity to picryl chloride was suppressed after i.v. administration of Cimicifugoside, 1.0-2.0 mg/mouse. The immunosuppressive activity of Cimicifugoside is preferentially directed toward B-cell function with larger doses being required for suppression of T-cell function.

Inhibition of nucleoside transport and synergistic potentiation of methotrexate cytotoxicity by Cimicifugoside, a triterpenoid from Cimicifuga simplex

Eur J Pharm Sci 2009 Nov 5;38(4):355-61.PMID:19748575DOI:10.1016/j.ejps.2009.08.011.

Cimicifugoside, a triterpenoid isolated from Cimicifuga simplex, which has been used as a traditional Chinese medicine due to its anti-inflammatory, analgesic or anti-pyretic action, was examined for inhibition of nucleoside transport and synergistic potentiation of methotrexate cytotoxicity. Cimicifugoside inhibited uptake of uridine, thymidine and adenosine in human leukemia U937 cells with the low nanomolar IC(50) values, but did not affect that of uracil, leucine or 2-deoxyglucose at Cimicifugoside analogs differentially inhibited uridine uptake in the order Cimicifugoside>cimicifugenin (aglycon of Cimicifugoside)>bugbanoside B>cimicifugenin A, O-methyl cimicifugenin and bugbanoside A. Cimicifugoside had less affinity for the binding site of nitrobenzylthioinosine (typical high-affinity inhibitor of equilibrative nucleoside transporter-1) in U937 cells, K562 cells and human erythrocyte membranes compared with the prototype nucleoside transport inhibitor dipyridamole. Cimicifugoside markedly potentiated methotrexate cytotoxicity in a culture of U937 cells and human carcinoma KB cells. Potentiation of methotrexate cytotoxicity by Cimicifugoside analogs in U937 cells was in proportion to their inhibitory activity against uridine uptake. The present study demonstrates that Cimicifugoside is a novel specific nucleoside transport inhibitor that displays synergistic potentiation of methotrexate cytotoxicity.

Black cohosh: coming full circle?

J Ethnopharmacol 2012 Jun 14;141(3):775-9.PMID:22504147DOI:10.1016/j.jep.2012.03.050.

Ethnopharmacological relevance: Black cohosh (Actaea racemosa L.), Ranunculaceae, thrives in temperate climates east of the Mississippi River in the USA. It is economically important to the Appalachian region where it is wild harvested, but it has resisted most efforts at deliberate cultivation. Black cohosh has been used for many centuries both in Europe and in the US (by indigenous people and subsequent Caucasian medical practitioners), most notably for indications of premenstrual syndrome (PMS), menstrual pain and cramping. Aim of the study: To highlight black cohosh as an example in which disregard for the ethnobotanical and ethnopharmacologic usages of a plant has perhaps hindered modern scientific attempts to understand the mechanism of action of its bioactive phytochemicals, and ascribe cause to effect. Results: Research on its mode of action has historically focused on its presumed hormonal (phytoestrogenic) activity, but very recent work suggests that it may in fact be acting as an antinociceptive agent. Re-examination of some of the writings of 19th and 20th century physicians and folk literature suggests that this mode of action may have been overlooked in modern experimentalists' in vitro and animal studies and in the very few well conducted human trials to date. Conclusions: The common folk perception of this plant as a "remedy for female problems" may thus require revision, as it may possess more general analgesic properties. In the broader context, ethnopharmacologic indications for other herbal remedies must be revisited in light of the explosion in understanding of mechanisms of action of small molecule effectors of which actein and Cimicifugoside (from black cohosh) are only two examples.