Cyclogalegigenin

CAS# 84605-18-5

Cyclogalegigenin

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Chemical structure

Cyclogalegigenin

3D structure

Chemical Properties of Cyclogalegigenin

Cas No. 84605-18-5 SDF Download SDF
PubChem ID 134801 Appearance Powder
Formula C30H50O5 M.Wt 490.71
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility DMSO : ≥ 100 mg/mL (203.78 mM)
H2O : < 0.1 mg/mL (insoluble)
*"≥" means soluble, but saturation unknown.
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-NGPKLKSDSA-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.

Source of Cyclogalegigenin

The root of Astragalus membranaceus (Fisch.) Bunge

Biological Activity of Cyclogalegigenin

Description1. Cycloastragenol and astragaloside IV can suppress ROS-associated ER stress and then inhibit TXNIP/NLRP3 inflammasome activation with regulation of AMPK activity, and thereby ameliorate endothelial dysfunction by inhibiting inflammation and reducing cell apoptosis. 2. Cycloastragenol stimulates telomerase activity in human neonatal keratinocytes and rat neuronal cells, and induces CREB activation followed by tert and bcl2 expression, cycloastragenol may have a novel therapeutic role in depression. 3. Cycloastragenol can suppress the accumulation of cytoplasmic lipid droplet in 3T3-L1 adipocytes. 4. Cycloastragenol and astragaloside IV have been shown to improve the proliferative response of CD8+ T lymphocytes from HIV-infected patients by upregulating telomerase activity, they also may exert their cellular effects through the activation of the Src/MEK/ERK pathway. 5. Cycloastragenol can remarkably inhibit CYP3A4 and activate CYP2E1 in rats. 6. Cycloastragenol has been shown to extend T cell proliferation by increasing telomarase activity showing that it may also help delay the onset of cellular aging; it is an extraordinary wound healing agent; it inhibits the apoptosis of PC12 induced by 6-OHDA, may be as potential neuroprotective agents in the treatment of Parkinson's disease.
TargetsROS | AMPK | IL Receptor | ERK | MEK | Src | cAMP | Bcl-2/Bax | Telomerase

Cyclogalegigenin Dilution Calculator

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Cyclogalegigenin Molarity Calculator

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Preparing Stock Solutions of Cyclogalegigenin

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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Background on Cyclogalegigenin

Cycloastragenol, a natural tetracyclic triterpenoid, was first identified when screening Astragalus membranaceus extracts for active ingredients with antiaging properties. IC50 value: Target: In vitro: In the study of Cycloastragenolon the treatment of degenerative diseases, the result showed that first-pass intestinal metabolism of cycloastragenol might occur upon passage through the intestinal epithelium. Cycloastragenol underwent extensive metabolism in rat and human liver microsomes with only 17.4% and 8.2%, respectively, of the starting amount of Cycloastragenol remaining after 30 min of incubation [1]. The present study demonstrates that cycloastragenol stimulates telomerase activity and cell proliferation in human neonatal keratinocytes. In particular, cycloastragenol promotes scratch wound closure of human neonatal keratinocyte monolayers in vitro [3]. In vivo: Rats were treated with Cycloastragenol (40 mg·kg- 1·d- 1) for 7 days to induce hepatic microsomal enzyme. The result showed that compared with the control, cycloastragenol obviously activated CYP2E1, and remarkably inhibited CYP3A4 [2].

References:
[1]. Jing Zhu, et al. In vitro Intestinal Absorption and First-pass Intestinal and Hepatic Metabolism of Cycloastragenol, a Potent Small Molecule Telomerase Activator. Drug Metabolism and Pharmacokinetics Volume 25, Issue 5, 2010, Pages 477-486 [2]. WEI Bao-hong, et al. Effect of continuous oral cycloastragenol on the activity of cytochrome P450 enzymes in rats. Chinese New Drugs Journal, 2014 -04 [3]. Ip FC, et al. Cycloastragenol is a potent telomerase activator in neuronal cells: implications for depression management. Neurosignals. 2014;22(1):52-63.

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References on Cyclogalegigenin

Astragaloside IV and cycloastragenol are equally effective in inhibition of endoplasmic reticulum stress-associated TXNIP/NLRP3 inflammasome activation in the endothelium.[Pubmed:25922268]

J Ethnopharmacol. 2015 Jul 1;169:210-8.

ETHNOPHARMACOLOGICAL RELEVANCE: Astragaloside IV and cycloastragenol are present together in Astragalus membranaceus Moench (Fabaceae) and this study aims to simultaneously investigate their regulation of endothelial homeostasis in the setting of endoplasmic reticulum stress (ER stress). MATERIAL AND METHODS: We stimulated endothelial cells with palmitate (PA 100muM) to evoked ROS-associated ER stress and observed the effects of astragaloside IV and cycloastragenol on thioredoxin-interacting protein (TXNIP) expression, NLRP3 inflammasome activation and mitochondrion-dependent apoptosis. RESULTS: Astragaloside IV and cycloastragenol inhibited ROS generation and attenuated ER stress inducer IRE1alpha phosphorylation, indicating the inhibition of ROS-associated ER stress. In response to ER stress, TXNIP expression increased, accompanied with NLRP3 induction and increased IL-1beta and IL-6 production, but these alternations were reversed by treatment with astragaloside IV and cycloastragenol, demonstrating the inhibitory effects of astragaloside IV and cycloastragenol on TXNIP/NLRP3 inflammasome activation. Inflammasome activation led to mitochondrial cell death in endothelial cells, whereas astragaloside IV and cycloastragenol restored the loss of the mitochondrial membrane potential with inhibition of caspase-3 activity, and thereby protected cells from ER stress-induced apoptosis. Astragaloside IV and cycloastragenol enhanced AMPK phosphorylation and AMPK inhibitor compound C diminished their beneficial effects, indicative of the potential role of AMPK in their regulation. CONCLUSIONS: Astragaloside IV and cycloastragenol suppressed ROS-associated ER stress and then inhibited TXNIP/NLRP3 inflammasome activation with regulation of AMPK activity, and thereby ameliorated endothelial dysfunction by inhibiting inflammation and reducing cell apoptosis. Simultaneous investigations further showed that astragaloside IV and cycloastragenol were equally effective in regulation of endothelial homeostasis.

Astragaloside IV and cycloastragenol stimulate the phosphorylation of extracellular signal-regulated protein kinase in multiple cell types.[Pubmed:22083896]

Planta Med. 2012 Jan;78(2):115-21.

Two Chinese herb-derived small molecule telomerase activators, astragaloside IV (AG-IV) and cycloastragenol (CAG), have recently been shown to improve the proliferative response of CD8+ T lymphocytes from HIV-infected patients by upregulating telomerase activity. Here, we examined the signaling mechanism of AG-IV and CAG. Telomerase activity in human embryonic kidney HEK293 fibroblasts was increased upon treatment with increasing concentrations of AG-IV or CAG. Both compounds induced the phosphorylation of extracellular signal-regulated protein kinase (ERK) in a time- and dose-dependent manner in HEK293 cells and HEK-neo keratinocytes. AG-IV and CAG also stimulated ERK phosphorylation in other cell lines of lung, brain, mammary, endothelial, and hematopoietic origins. Use of selective inhibitors and dominant negative mutants revealed the involvement of c-Src, MEK (ERK kinase), and epidermal growth factor receptor in CAG-induced ERK phosphorylation. Our data indicate that AG-IV and CAG may exert their cellular effects through the activation of the Src/MEK/ERK pathway.

Cycloastragenol, a triterpene aglycone derived from Radix astragali, suppresses the accumulation of cytoplasmic lipid droplet in 3T3-L1 adipocytes.[Pubmed:24942874]

Biochem Biophys Res Commun. 2014 Jul 18;450(1):306-11.

Cycloastragenol (CAG), a bioactive triterpenoid sapogenin isolated from the Chinese herbal medicine Radix astragali, was reported to promote the phosphorylation of extracellular signal-regulated protein kinase (ERK). Here we investigated the effect of CAG on adipogenesis. The image-based Nile red staining analyses revealed that CAG dose dependently reduced cytoplasmic lipid droplet in 3T3-L1 adipocytes with the IC50 value of 13.0 muM. Meanwhile, cytotoxicity assay provided evidence that CAG was free of injury on HepG2 cells up to 60 muM. In addition, using calcium mobilization assay, we observed that CAG stimulated calcium influx in 3T3-L1 preadipocytes with a dose dependent trend, the EC50 value was determined as 21.9 muM. There were proofs that elevated intracellular calcium played a vital role in suppressing adipocyte differentiation. The current findings demonstrated that CAG was a potential therapeutic candidate for alleviating obesity and hyperlipidemia.

Cycloastragenol is a potent telomerase activator in neuronal cells: implications for depression management.[Pubmed:25095809]

Neurosignals. 2014;22(1):52-63.

Cycloastragenol (CAG) is an aglycone of astragaloside IV. It was first identified when screening Astragalus membranaceus extracts for active ingredients with antiaging properties. The present study demonstrates that CAG stimulates telomerase activity and cell proliferation in human neonatal keratinocytes. In particular, CAG promotes scratch wound closure of human neonatal keratinocyte monolayers in vitro. The distinct telomerase-activating property of CAG prompted evaluation of its potential application in the treatment of neurological disorders. Accordingly, CAG induced telomerase activity and cAMP response element binding (CREB) activation in PC12 cells and primary neurons. Blockade of CREB expression in neuronal cells by RNA interference reduced basal telomerase activity, and CAG was no longer efficacious in increasing telomerase activity. CAG treatment not only induced the expression of bcl2, a CREB-regulated gene, but also the expression of telomerase reverse transcriptase in primary cortical neurons. Interestingly, oral administration of CAG for 7 days attenuated depression-like behavior in experimental mice. In conclusion, CAG stimulates telomerase activity in human neonatal keratinocytes and rat neuronal cells, and induces CREB activation followed by tert and bcl2 expression. Furthermore, CAG may have a novel therapeutic role in depression.

Description

Cycloastragenol, a natural tetracyclic triterpenoid, was first identified when screening Astragalus membranaceus extracts for active ingredients with antiaging properties.

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