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(Synonyms: 葳岩仙皂苷 C) 目录号 : GC35616

A triterpenoid saponin with diverse biological activities

Cauloside C Chemical Structure

Cas No.:20853-58-1

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产品描述

Hederoside D2 is a triterpenoid saponin originally isolated from C. robustum rhizome and roots and has diverse biological activities.1,2 It induces potassium release and hemolysis in mouse erythrocytes in a pH-dependent manner when used at a concentration of 10 μg/ml.2 Hederoside D2 is cytotoxic to N1E-115 neuroblastoma cells at low pH. It induces proliferation of human embryonic fibroblasts in acidic medium, an effect that can be blocked by the calcium channel blockers verapamil , diltiazem, and nitrendipine .

1.Murakami, T., Nagasawa, M., Urayama, S., et al.New triterpenoid saponins in the rhizome and roots of Caulophyllum robustumYakugaku Zasshi88(3)321-324(1968) 2.Likhatskaya, G.N., Aminin, D.L., Agafonova, I.G., et al.The pH-dependent channels formed by cauloside CAdvances in Experimental Medicine and Biology404239-249(1996)

Chemical Properties

Cas No. 20853-58-1 SDF
别名 葳岩仙皂苷 C
Canonical SMILES CC1(C)CC[C@@]2(CC[C@]3(C)C([C@@H]2C1)=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6OC[C@H](O)[C@H](O)[C@H]6O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@@]([C@@H]5CC[C@@]34C)(C)CO)C(O)=O
分子式 C41H66O13 分子量 766.95
溶解度 DMF: 20 mg/ml,DMF:PBS(pH 7.2)(1:1): 0.5 mg/ml,DMSO: 15 mg/ml,Ethanol: 5 mg/ml 储存条件 Store at -20°C
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1 mM 1.3039 mL 6.5193 mL 13.0387 mL
5 mM 0.2608 mL 1.3039 mL 2.6077 mL
10 mM 0.1304 mL 0.6519 mL 1.3039 mL
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Research Update

The effect of pH on biological activity of plant cytotoxin Cauloside C

Comp Biochem Physiol A Mol Integr Physiol 1999 Jan;122(1):45-51.PMID:10216931DOI:10.1016/s1095-6433(98)10138-1.

The effect of plant carboxyl-containing glycoside Cauloside C upon eucaryotic cells has been studied. The glycoside interacts with cells as a pH-dependent cytotoxin and increases K+ leakage and Ca2+ uptake with strong action in acidic media Cell viability after glycoside action at acidic pH may be recovered by the shift of medium pH from 5.6 to 7.4. Directed transport of low molecular weight effectors such as cAMP and Ca2+ to human embryo fibroblasts under the action of Cauloside C has been demonstrated. Calcium uptake is accompanied by about a twofold stimulation of fibroblast proliferation in serum-free medium. The manifestation of the effect depends on the strictly determined time of the 'open' state of the membrane permeability (2 min) and upon concentration of glycoside in the medium (1 ng/ml) Cauloside C-stimulated Ca-transport is not blocked by Ca-channel blockers such as verapamil, diltiasem, and nitrendipine (all at a concentration of 1 x 10(-6) M) but these blockers inhibit cauloside C-stimulated proliferation of fibroblasts. We conclude that stimulation of fibroblast proliferation is caused by activation of membrane associated Ca-channels at the expense of calcium, incorporated into cells with Cauloside C. The use of Cauloside C as a new biochemical tool for cell permeabilisation is suggested.

Spectrum-Effect Relationships between Fingerprints of Caulophyllum robustum Maxim and Inhabited Pro-Inflammation Cytokine Effects

Molecules 2017 Oct 26;22(11):1826.PMID:29072610DOI:10.3390/molecules22111826.

Caulophyllum robustum Maxim (CRM) is a Chinese folk medicine with significant effect on treatment of rheumatoid arthritis (RA). This study was designed to explore the spectrum-effect relationships between high-performance liquid chromatography (HPLC) fingerprints and the anti-inflammatory effects of CRM. Seventeen common peaks were detected by fingerprint similarity evaluation software. Among them, 15 peaks were identified by Liquid Chromatography-Mass Spectrometry (LC-MS). Pharmacodynamics experiments were conducted in collagen-induced arthritis (CIA) mice to obtain the anti-inflammatory effects of different batches of CRM with four pro-inflammation cytokines (TNF-α, IL-β, IL-6, and IL-17) as indicators. These cytokines were suppressed at different levels according to the different batches of CRM treatment. The spectrum-effect relationships between chemical fingerprints and the pro-inflammation effects of CRM were established by multiple linear regression (MLR) and gray relational analysis (GRA). The spectrum-effect relationships revealed that the alkaloids (N-methylcytisine, magnoflorine), saponins (leiyemudanoside C, leiyemudanoside D, leiyemudanoside G, leiyemudanoside B, cauloside H, leonticin D, cauloside G, cauloside D, cauloside B, Cauloside C, and cauloside A), sapogenins (oleanolic acid), β-sitosterols, and unknown compounds (X3, X17) together showed anti-inflammatory efficacy. The results also showed that the correlation between saponins and inflammatory factors was significantly closer than that of alkaloids, and saponins linked with less sugar may have higher inhibition effect on pro-inflammatory cytokines in CIA mice. This work provided a general model of the combination of HPLC and anti-inflammatory effects to study the spectrum-effect relationships of CRM, which can be used to discover the active substance and to control the quality of this treatment.

[The structure of sulfated Cauloside C]

Bioorg Khim 2000 May;26(5):387-91.PMID:10900510doi

The structure of the sulfated analogue of Cauloside C, a biologically active triterpenoid glycoside, was elucidated to be 3-O-[beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinopyranosyl]-he deragenin 23,4',4",6"-tetrasulfate pentasodium salt by the comparison of its 13C NMR spectrum with that of Cauloside C potassium salt.

[The mechanism of the interaction of the pH-dependent cytostatic Cauloside C with the membranes of tumor cells and liposomes]

Izv Akad Nauk SSSR Biol 1990 May-Jun;(3):338-42.PMID:2401767doi

The effect of the medium pH on accumulation of [3H]-cauloside C by tumor cells, its intracellular localization, and interaction of the glicoside with membranes of tumor cells and liposomes has been studied. The shift towards weakly acids pH leads to the increase in the amount of Cauloside C accumulated by tumor cells and changes the pattern of interaction of Cauloside C with the membranes.

Analytical methods for determination of magnoflorine and saponins from roots of Caulophyllum thalictroides (L.) Michx. using UPLC, HPLC and HPTLC

J Pharm Biomed Anal 2011 Dec 15;56(5):895-903.PMID:21872415DOI:10.1016/j.jpba.2011.07.028.

Analytical methods including HPLC, UPLC and HPTLC are presented for the determination of major alkaloid and triterpene saponins from the roots of Caulophyllum thalictroides (L.) Michx. (blue cohosh) and dietary supplements claiming to contain blue cohosh. A separation by LC was achieved using a reversed phase column, PDA with ELS detection, and ammonium acetate/acetonitrile gradient as the mobile phase. Owing to their low UV absorption, the triterpene saponins were detected by evaporative light scattering. The eight triterpene saponins (cauloside H, leonticin D, cauloside G, cauloside D, cauloside B, Cauloside C, cauloside A and saponin PE) and the alkaloid magnoflorine could be separated within 35 min using HPLC method and within 8.0 min using UPLC method with detection limits of 10 μg/mL for saponins and 1 μg/mL for magnoflorine. The detection wavelength was 320 nm for magnoflorine and ELS detection was used for the eight saponins. The methods were also successfully applied to analyze different dietary supplements. For the products claiming to contain blue cohosh, there was a significant variability in the amounts of triterpene saponins detected. Calculations based on the analysis results for dietary supplements showed that maximum daily intake of alkaloid and saponins vary with the form (solids/liquids) and recommended doses according to the products label. Intakes varied from 0.57 to 15.8 mg/day for magnoflorine and from 5.97 to 302.4 mg/day for total saponins. LC-mass spectrometry coupled with electrospray ionization (ESI) method is described for the identification and confirmation of nine compounds in plant samples and dietary products. A HPTLC method was also developed for the fast chemical fingerprint analysis of C. thalictroides samples.