Cycloastragenol

CAS# 78574-94-4

Cycloastragenol

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Chemical structure

Cycloastragenol

3D structure

Chemical Properties of Cycloastragenol

Cas No. 78574-94-4 SDF Download SDF
PubChem ID 13943286 Appearance White powder
Formula C30H50O5 M.Wt 490.71
Type of Compound Isoprenoids Storage Desiccate at -20°C
Synonyms Astramembrangenin; Cyclosieversigenin
Solubility Soluble in methan
SMILES CC1(C(CCC23C1C(CC4C2(C3)CCC5(C4(CC(C5C6(CCC(O6)C(C)(C)O)C)O)C)C)O)O)C
Standard InChIKey WENNXORDXYGDTP-UOUCMYEWSA-N
Standard InChI InChI=1S/C30H50O5/c1-24(2)20(33)8-11-30-16-29(30)13-12-26(5)23(28(7)10-9-21(35-28)25(3,4)34)18(32)15-27(26,6)19(29)14-17(31)22(24)30/h17-23,31-34H,8-16H2,1-7H3/t17-,18-,19-,20-,21-,22-,23-,26+,27-,28+,29-,30+/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Cycloastragenol Dilution Calculator

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Cycloastragenol Molarity Calculator

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Preparing Stock Solutions of Cycloastragenol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.0379 mL 10.1893 mL 20.3786 mL 40.7573 mL 50.9466 mL
5 mM 0.4076 mL 2.0379 mL 4.0757 mL 8.1515 mL 10.1893 mL
10 mM 0.2038 mL 1.0189 mL 2.0379 mL 4.0757 mL 5.0947 mL
50 mM 0.0408 mL 0.2038 mL 0.4076 mL 0.8151 mL 1.0189 mL
100 mM 0.0204 mL 0.1019 mL 0.2038 mL 0.4076 mL 0.5095 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Cycloastragenol

Cycloartane-type sapogenol derivatives inhibit NFkappaB activation as chemopreventive strategy for inflammation-induced prostate carcinogenesis.[Pubmed:29678446]

Steroids. 2018 Jul;135:9-20.

Chronic inflammation is associated to 25% of cancer cases according to epidemiological data. Therefore, inhibition of inflammation-induced carcinogenesis can be an efficient therapeutic approach for cancer chemoprevention in drug development studies. It is also determined that anti-inflammatory drugs reduce cancer incidence. Cell culture-based in vitro screening methods are used as a fast and efficient method to investigate the biological activities of the biomolecules. In addition, saponins are molecules that are isolated from natural sources and are known to have potential for tumor inhibition. Studies on the preparation of analogues of cycloartane-type sapogenols (9,19-cyclolanostanes) have so far been limited. Therefore we have decided to direct our efforts toward the exploration of new anti-tumor agents prepared from Cycloastragenol and its production artifact astragenol. The semi-synthetic derivatives were prepared mainly by oxidation, condensation, alkylation, acylation, and elimination reactions. After preliminary studies, five sapogenol analogues, two of which were new compounds (2 and 3), were selected and screened for their inhibitory activity on cell viability and NFkappaB signaling pathway activity in LNCaP prostate cancer cells. We found that the astragenol derivatives 1 and 2 as well as Cycloastragenol derivatives 3, 4, and 5 exhibited strong inhibitory activity on NFkappaB signaling leading the repression of NFkappaB transcriptional activation and suppressed cell proliferation. The results suggested that these molecules might have significant potential for chemoprevention of prostate carcinogenesis induced by inflammatory NFkappaB signaling pathway.

Astragaloside IV attenuates penicillin-induced epilepsy via inhibiting activation of the MAPK signaling pathway.[Pubmed:29115438]

Mol Med Rep. 2018 Jan;17(1):643-647.

Astrocytes perform several functions in the brain and spinal cord. Penicillin is commonly used for establishment of experimental epilepsy models. Previous studies have demonstrated that astragaloside IV (3-o-beta-d-xylopyranosyl-6-o-beta-d-glucopyranosyl-Cycloastragenol; ASIV) has comprehensive pharmacological functions on the attenuation of inflammation. In the present study, primary astrocyte cell cultures were divided into three groups: Control group, penicillin (2,500 microM) treatment group (epilepsy model), and penicillin+ASIV (20, 40, 80 and 160 micromol/l) treatment group. The expression levels of inflammatory factors, including interleukin1beta and tumor necrosis factoralpha, were determined in the groups using western blot and reverse transcriptionquantitative polymerase chain reaction analyses. The levels of members of the phosphorylatedmitogenactivated protein kinase (pMAPK) family, including pcJun Nterminal kinase 1/2, pextracellular signalregulated protein kinase 1/2 and pp38, were determined using western blot analysis. Cell viability of the astrocytes was detected using a 3(4,5dimethyl2thiazolyl)2,5diphenyl2Htetrazolium bromide assay and cell proliferation was evaluated using a Cell Counting Kit8 assay. The results revealed that ASIV significantly suppressed the expression of penicillininduced inflammatory factors in the astrocytes at the transcriptional and translational levels, and occurred in a dosedependent manner. The penicillininduced increase in the protein levels of the the pMAPK family were notably decreased by ASIV. In addition, the penicillininduced downregulation of primary astrocyte viability/cell proliferation was significantly reversed by the administration of ASIV. From these results, it was concluded that ASIV suppressed the penicillininduced upregulation of inflammatory factors and pMAPK in astrocytes, ultimately attenuating epilepsy.

A rapid method for sensitive profiling of bioactive triterpene and flavonoid from Astragalus mongholicus and Astragalus membranaceus by ultra-pressure liquid chromatography with tandem mass spectrometry.[Pubmed:29649754]

J Chromatogr B Analyt Technol Biomed Life Sci. 2018 May 15;1085:110-118.

Astragalus is one of the most popular Chinese herbal. Control of Astragalus quantity is most important, since that various varieties and ages largely affect bioactive metabolites and different pharmacological effects. Astragalus mongholicus and Astragalus membranaceus are both major sources of Astragalus according to the provisions in the Chinese Pharmacopoeia. Thus, a sensitive and rapid UPLC-MS/MS method for the simultaneous determination of l-Phenylalanine, Isoliquiritigenin, Liquiritigenin, Daidzein, Formononetin, Ononin, Calycosin, Calycosin-7-glucoside, Cycloastragenol, Astragaloside I, Astragaloside II, Astragaloside III and Astragaloside IV was established in this study. The detection was accomplished by MRM scanning in the positive ionization mode. Calibration curves offered linear ranges with r(2)>0.999. The method was successfully validated for the linearity, intra-day and inter day precisions, accuracy, recovery, matrix effect and stability. Then this method was successfully applied to detect the contents of 13 target flavonoids and triterpenoids metabolites in different organs and ages of A. mongholicus and A. membranaceus. Significant organs-, ages- and varieties- specificity of the 13 target metabolites were observed and discussed. The results provided basis and support for further exploration of the distribution of bioactive metabolites, namely flavonoids and triterpenoids, in different organs and ages of two Astragalus varieties. This method should be applicable to various Astragalus matrices for the quantitative analysis of the target flavonoids and triterpenoids.

Protective effects of astragaloside IV against ovalbumin-induced allergic rhinitis are mediated by T-box protein expressed in T cells/GATA-3 and forkhead box protein 3/retinoic acid-related orphan nuclear receptor gammat.[Pubmed:28586019]

Mol Med Rep. 2017 Aug;16(2):1207-1215.

3-O-beta-D-xylopyranosyl-6-O-beta-D-glucopyranosyl-Cycloastragenol, or Astragaloside IV (AST), is one of the major active ingredients isolated from Astragalus membranaceous with distinct pharmacological effects, and possesses anti-inflammatory, immunoregulatory and antifibrotic properties. However, the effects of AST on allergic rhinitis remain to be elucidated. The present study aimed to examine the effects of AST on immunoglobulin (Ig) Emediated allergic reactions in vivo, by using a mouse model of allergic rhinitis established via repetitive sensitization and intranasal challenge with ovalbumin (OVA). Intragastric administration of AST (25 mg/kg or 50 mg/kg) or dexamethasone (DEX; 3 mg/kg) significantly alleviated the inflammatory response, nasal symptoms and mucosa remodeling, and decreased the serum levels of OVAspecific IgE in allergic mice. Furthermore, treatment with AST or DEX significantly suppressed the mRNA and protein expression levels of the transcription factor GATA3 and retinoic acid receptorrelated orphan nuclear receptor (ROR)gammat in tissue samples isolated from the spleen and nasal mucosa of mice with allergic rhinitis. Conversely, mRNA and protein expression levels of Tbox protein expressed in T cells (Tbet) and forkhead box protein 3 (Foxp3) were upregulated in the spleen and nasal mucosa of mice with allergic rhinitis following treatment with AST or DEX, and spleen protein levels of signal transducer and activator of transcription 3 followed a similar trend. In addition, treatment with AST was associated with fewer adverse events compared with treatment with DEX. The present results suggested that treatment with AST may attenuate OVAinduced allergic rhinitis via regulating the expression of the transcription factors GATA3, RORgammat, Tbet and Foxp3, which commit T helper cells to the Th1 phenotype. Therefore, AST may represent an alternative therapeutic approach for the treatment of patients with allergic rhinitis.

Simultaneous quantification of multiple components in rat plasma by UPLC-MS/MS and pharmacokinetic study after oral administration of Huangqi decoction.[Pubmed:29243282]

Biomed Chromatogr. 2018 May;32(5):e4178.

A rapid, sensitive and accurate UPLC-MS/MS method was developed for the simultaneous quantification of components of Huangqi decoction (HQD), such as calycosin-7-O-beta-d-glucoside, calycosin-glucuronide, liquiritin, formononetin-glucuronide, isoliquiritin, liquiritigenin, ononin, calycosin, isoliquiritigenin, formononetin, glycyrrhizic acid, astragaloside IV, Cycloastragenol, and glycyrrhetinic acid, in rat plasma. After plasma samples were extracted by protein precipitation, chromatographic separation was performed with a C18 column, using a gradient of methanol and 0.05% acetic acid containing 4mm ammonium acetate as the mobile phase. Multiple reaction monitoring scanning was performed to quantify the analytes, and the electrospray ion source polarity was switched between positive and negative modes in a single run of 10 min. Method validation showed that specificity, linearity, accuracy, precision, extraction recovery, matrix effect and stability for 14 components met the requirements for their quantitation in biological samples. The established method was successfully applied to the pharmacokinetic study of multiple components in rats after intragastric administration of HQD. The results clarified the pharmacokinetic characteristics of multiple components found in HQD. This research provides useful information for understanding the relation between the chemical components of HQD and their therapeutic effects.

Description

Astramembrangenin (Cycloastragenol) is a triterpenoid saponin compound and a hydrolysis product of the main active ingredient in Astragalus membranaceus (Fisch.) Bunge. Astramembrangenin is orally safe and has broad Extensive pharmacological effects, including telomerase activation, telomere elongation, anti-inflammatory and anti-oxidative properties. Astramembrangenin has antiaging properties, CAG stimulates telomerase activity in human neonatal keratinocytes and rat neuronal cells, and induces CREB activation followed by tert and bcl2 expression. Cycloastragenol (CAG) may have a novel therapeutic role in depression.

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