Cycloastragenol - CAS 84605-18-5
Catalog number:
84605-18-5
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C30H50O5
Molecular Weight:
490.71
COA:
Inquire
Targets:
Others
Description:
Cycloastragenol is a natural tetracyclic triterpenoid. It is an aglycone derivative of astragaloside IV found in the root of Korean Astragalus membranaceus. It has antiaging properties. lt may activate telomerase and stimulates telomerase activity and cell proliferation in human neonatal keratinocytes. It promotes scratch wound closure of human neonatal keratinocyte monolayers in vitro. lt obviously activated CYP2E1, and remarkably inhibited CYP3A4. lt is used as a nutraceutical. It stimulates the repair of DNA damage by activating telomerase,a nucleoprotein enzyme which catalyses synthesis and growth of telomeric DNA.
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Purity:
>98%
Appearance:
White Solid
Synonyms:
Cyclogalegigenin;(3β,6α,16β,20R,24S)-20,24-Epoxy-9,19-cyclolanostane-3,6,16,25-tetrol;(3b,6a,16b,24R)-20,24-Epoxy-9,19-cyclolanostane-3,6,16,25-tetrol
Solubility:
10 mM in DMSO
Storage:
-20°C Freezer
MSDS:
Inquire
Application:
Cycloastragenol has antiaging properties. lt may activate telomerase and stimulates telomerase activity and cell proliferation in human neonatal keratinocytes. lt is used as a nutraceutical. It stimulates the repair of DNA damage by activating telomerase,a nucleoprotein enzyme.
Quality Standard:
In-house standard
Shelf Life:
2 month in rt, long time
Quantity:
Grams-Kilos
Boiling Point:
617.2±55.0 °C | Condition: Press: 760 Torr
Melting Point:
>230°C (dec.)
Density:
1.20±0.1 g/cm3 | Condition: Temp: 20 °C Press: 760 Torr
InChIKey:
WENNXORDXYGDTP-ODAITAILSA-N
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
Canonical SMILES:
CC1(C(CCC23C1C(CC4C2(C3)CCC5(C4(CC(C5C6(CCC(O6)C(C)(C)O)C)O)C)C)O)O)C
1.Smith degradation, an efficient method for the preparation of cycloastragenol from astragaloside IV.
Feng LM1, Lin XH1, Huang FX1, Cao J1, Qiao X1, Guo DA1, Ye M2. Fitoterapia. 2014 Jun;95:42-50. doi: 10.1016/j.fitote.2014.02.014. Epub 2014 Mar 5.
Cycloastragenol (CA) is the genuine sapogenin of astragaloside IV (ASI). This study focuses on the preparation of CA from ASI. Five hydrolysis methods were compared including H2SO4 hydrolysis, HCl hydrolysis, two-phase acid hydrolysis, mild acid hydrolysis, and Smith degradation. Seven hydrolysis products were purified, and five of them were identified as new compounds. The results indicated that Smith degradation was the most effective approach to prepare CA. In contrast, mild acid hydrolysis produced CA at a low yield, accompanied with the artificial sapogenin astragenol. The other three acid hydrolysis methods mainly produced astragenol. Furthermore, the reaction conditions for Smith degradation were optimized as follows: ASI was dissolved in 60% MeOH-H2O solution, oxidized with 5 equiv. NaIO4 for 12h, followed by reduction with 3 equiv. NaBH4 for 4h, and finally acidified with 1M H2SO4 at pH2 for 24h. Under the optimal conditions, CA could be prepared from ASI at a yield of 84.
2.Evaluation of a novel anti-aging topical formulation containing cycloastragenol, growth factors, peptides, and antioxidants.
Weiss RA, Weiss MA. J Drugs Dermatol. 2014 Sep;13(9):1135-9.
BACKGROUND/OBJECTIVE: This study investigates the efficacy, tolerance, and usability of a single product containing cycloastragenol, growth factors, peptides, and antioxidants to decrease the visible signs of aging, including fine lines, and wrinkles, texture, pore size, elasticity, skin color/clarity, redness, hydration, and overall skin quality.
3.Astragaloside IV and cycloastragenol are equally effective in inhibition of endoplasmic reticulum stress-associated TXNIP/NLRP3 inflammasome activation in the endothelium.
Zhao Y1, Li Q2, Zhao W1, Li J3, Sun Y3, Liu K3, Liu B3, Zhang N4. J Ethnopharmacol. 2015 Jul 1;169:210-8. doi: 10.1016/j.jep.2015.04.030. Epub 2015 Apr 25.
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).
4.Cycloastragenol is a potent telomerase activator in neuronal cells: implications for depression management.
Ip FC1, Ng YP, An HJ, Dai Y, Pang HH, Hu YQ, Chin AC, Harley CB, Wong YH, Ip NY. Neurosignals. 2014;22(1):52-63. doi: 10.1159/000365290. Epub 2014 Jul 31.
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.
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Chemical Structure

CAS 84605-18-5 Cycloastragenol

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