| Identification | Back Directory | [Name]
CYCLOASTRAGENOL | [CAS]
78574-94-4 | [Synonyms]
Cyclogalegenol
Astramembrangenin
Cyclosieversigenin
CYCLOASTRAGENOL(SH)
Cycloastragenol, 98%, from Astragalus membranaceus Bunge
Cycloastragenol（Cyclosiversigenin,Astramembrangenin,Cyclosieversigenin）
9,19-Cyclolanostane-3,6,16,25-tetrol, 20,24-epoxy-, (3β,6α,16β,20R,24S)-
(3beta,6alpha,16beta,20R,24S) 20,24-Epoxy-9,19-cyclolanostane-3,6,16,25-tetrol
(2aR,3R,4S,5aS,5bS,7S,7aR,9S,11aR,12aS)-3-((2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl)-2a,5a,8,8-tetramethylhexadecahydrocyclopenta[a]cyclopropa[e]phenanthrene-4,7,9-triol | [Molecular Formula]
C30H50O5 | [MDL Number]
MFCD11618124 | [MOL File]
78574-94-4.mol | [Molecular Weight]
490.72 |
| Chemical Properties | Back Directory | [Melting point ]
241.0 to 245.0 °C | [Boiling point ]
617.2±55.0 °C(Predicted) | [density ]
1.20±0.1 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Sparingly soluble in aqueous buffers. For maximum solubility in aqueous buffers, first dissolve in DMF and then dilute with the aqueous buffer of choice. Cycloastragenol has a solubility of approximately 0.25 mg/ml in a 1:8 solution of DMF:PBS (pH 7.2) using this method.Solubility in DMSO is 98 mg/mL (199.7 mM) | [form ]
powder to crystal | [pka]
14.57±0.29(Predicted) | [color ]
White to Almost white | [Optical Rotation]
[α]/D +45 to +60°, c =1 in methanol | [InChIKey]
WENNXORDXYGDTP-XWIGRFCYNA-N |
| Hazard Information | Back Directory | [Description]
Cycloastragenol(78574-94-4) is the genuine sapogenin of astragaloside IV, a major bioactive constituent of the Chineseherbal medicine Astragali Radix (Huang-Qi). Astragaloside IV exhibits various pharmacological properties, suchas anti-viral, anti-inflammatory, anti-aging,and antioxidant activities.Cycloastragenol is a telomerase activator,which delays the onset of cellularaging. Thus, cycloastragenol is considered as a newgeneration of anti-aging agent.
| [Uses]
Cycloastragenol(78574-94-4), a saponin and aglycone found in Astragalus, is a natural triterpenoid. It has anti-aging properties and can also act as an adjuvant therapy for cancer by enhancing the effectiveness of anti-cancer drugs, reducing their toxicity, and preventing/treating leukopenia caused by these treatments.
| [Application]
Cycloastragenol can be used for anti-aging, and it also has anti-cancer adjuvant therapeutic effects of enhancing the curative effect of anti-cancer drugs, reducing the toxicity of anti-cancer drugs, preventing and treating leukopenia caused by anti-cancer drug treatment. | [Definition]
ChEBI: Cycloastragenol is a sapogenin that is the aglycone derivative of astragaloside IV, a major saponin extracted from the root of Astragalus membranaceus. It has a role as a metabolite. It is a sapogenin, a pentacyclic triterpenoid, a tetrol and a member of oxolanes. It derives from a hydride of a 5alpha-gonane. | [Preparation]
The cycloastragenol was prepared by acid hydrolysis, and the oxidation reaction was carried out before the hydrolysis. The technological process is: oxidation-reduction-hydrolysis-extraction. | [benefits]
Cycloastragenol has a steroidal skeleton of tetracyclic triterpene and possess diverse pharmacological activities such as anti-aging, anti-inflammatory, anti-fibrosis, pro-wound healing, liver protection and endothelial protection.
A comprehensive review of cycloastragenol: Biological activity, mechanism of action and structural modifications | [Biological Activity]
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]. | [Biochem/physiol Actions]
Cycloastragenol is used as a nutraceutical (e.g. TAT2) and seems to moderately increase the telomerase activity and proliferative capacity of both CD4 and CD8 T-cells. Cycloastragenol possesses antiviral, antimicrobial, anti-inflammatory, anti-hepatotoxic, anti-leukemia, antitumor and antinociceptive activity. It also acts as an immunomodulator. | [Side effects]
Cycloastragenol is a telomerase activator. Fortunately, the experimental results did not show an increased risk of cancer and other adverse effects. | [Synthesis]
GENERAL STEPS: Astragaloside IV (1) (5.00 g, mmol) was dissolved in 10% HCl-MeOH solution (TCI America) (500 mL) and the reaction was stirred at room temperature for 7 days. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure at 20 °C to half of the original volume (avoid heating). The concentrate was extracted by partitioning with aqueous sodium bicarbonate and ethyl acetate. The aqueous phase was extracted once more with ethyl acetate. The organic phases were combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (chloroform/methanol, 20:1 to 14:1 gradient elution). To displace the residual solvent, the purified product was dissolved in ethanol and the solvent was removed under reduced pressure to afford the target compound 2 (2.1 g, 64% yield).1H NMR (CDCl3) δ (ppm): 0.34 (d, J = 4.7 Hz, 1H), 0.48 (d, J = 4.3 Hz, 1H), 0.92 (s, 3H), 0.93 (s, 3H). 1.0-1.8 (m, 13H), 1.11 (s, 3H), 1.19 (s, 3H), 1.22 (s, 6H), 1.27 (s, 3H), 1.9-2.0 (m, 4H), 2.30 (d, J = 7.8 Hz, 1H), 2.54 (q, J = 11.8 Hz, 1H), 3.27 (m, 1H), 3.50 (m, 1H), 3.72 (t, J = 7.4 Hz, 1H), 4.65 (q, J = 7.4 Hz, 1H).ESI-MS m/z: Positive 491 (M + H)+, Negative 549 (M + AcO)-.TLC (Merck, Kieselgel 60) Rf = 0.33 (Chloroform/methanol, 6:1). | [Source]
Cycloastragenol is isolated from Astragalus species. | [storage]
4°C, protect from light | [Dosage]
As a dietary supplement, take one 100mg capsule of Cycloastragenol daily. | [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 PharmacokineticsVolume 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. |
|
|