84605-18-5

Basic information

• Product Name: cycloastragenol
• Synonyms: cycloastragenol;(3b,6a,16b,24R)-20,24-Epoxy-9,19-cyclolanostane-3,6,16,25-tetrol;Cyclogalagenin;Cyclogalegenin;Cyclogalegigenin;Cyclogalgeginin;(3b,5ξ,6a,9ξ,10ξ,16b,17ξ,24R)-20,24-Epoxy-9,19-cyclolanostane-3,6,16,25-tetrol;(3beta,6alpha,16beta,24R)-20,24-Epoxy-9,19-cyclolanostane-3,6,16,25-tetrol
• CAS NO: 84605-18-5
• Molecular Formula: C₃₀H₅₀O₅
• Molecular Weight: 490.715
• Product Categories: palnt extract;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 84605-18-5.mol
• Article Data: 37

Chemical Properties

• Boiling Point: 617.2 °C at 760 mmHg
• Flash Point: 327.1 °C
• Appearance: Colorless needle crystal
• Density: 1.20
• Vapor Pressure: 8.17E-18mmHg at 25°C
• Refractive Index: 1.582
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly), Pyridine (Slightly)
• PKA: 14.57±0.29(Predicted)
• CAS DataBase Reference: cycloastragenol(CAS DataBase Reference)
• NIST Chemistry Reference: cycloastragenol(84605-18-5)
• EPA Substance Registry System: cycloastragenol(84605-18-5)

Safety Data

• Hazardous Substances Data: 84605-18-5(Hazardous Substances Data)

Usage

Description

Cycloastragenol (TA-65), a small-triterpenoid purified from the root of an Asian medicinal herb, has currently received particular attention for its potential to regulate transcription of telomerase. TA-65 is capable to increase average telomere length and to decrease the percentage of critically short telomeres and DNA damage in MEFs that harbor critically short telomeres. The effects on telomerase appear to be in common with other triterpenoid saponins (ie, ginsenosides RG1 and Rg3). These compounds at concentrations from 1 to 20 μM were reported to protect against IL-1β-, H2O2-, and tert-butylhydroperoxide-induced senescence in human chondrocytes, endothelial progenitor cells and fibroblasts, respectively.

Biological Activity

Cycloastragenol, the aglycone derivative of astragaloside A, can be found in various species of Astragalus and is reported to activate telomerase. It has been shown to slow telomere loss, increase replicative capacity, and improve immune function in CD8+ T lymphocytes from HIV-1-infected patients.

Laboratory Procedures

Cycloastragenol is supplied as a crystalline solid. A stock solution may be made by dissolving the cycloastragenol in the solvent of choice. Cycloastragenol is soluble in organic solvents such as ethanol, DMSO, and dimethyl formamide (DMF), which should be purged with an inert gas. The solubility of cycloastragenol in these solvents is approximately 10, 3, and 25 mg/ml, respectively. Cycloastragenol is sparingly soluble in aqueous buffers. For maximum solubility in aqueous buffers, cycloastragenol should first be dissolved in DMF and then diluted 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. We do not recommend storing the aqueous solution for more than one day.

Uses

Cycloastragenol is an aglycone derivative of astragaloside IV found in the root of Korean Astragalus membranaceus.

Definition

ChEBI: A sapogenin that is the aglycone derivative of astragaloside IV, a major saponin extracted from the root of Astragalus membranaceus.

InChI:InChI=1/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

Upstream product

• 84687-42-3 astragaloside III 
• 134563-28-3 cycloaraloside E 
• 135101-62-1 cyclocarposide 
• 84883-00-1 20S,24R-epoxycycloartan-3,6,16,25-tetraol-3-O-β-D-(2'-O-acetyl)xylopyranosyl-6-O-β-D-xylopyranoside 
• 1000992-24-4 cyclogalegigenin-3-O-β-D-rutinoside 
• 101858-42-8 cyclosieversioside E 
• 83207-58-3 cyclosieversioside F 
• 86408-19-7 Cyclosiversigenin 3-O-2)-β-D-xylopyranoside> 
• 88192-83-0 cyclosiversioside H 
• 88192-84-1 askenoside B 
• 86408-17-5 askendoside D 
• 86850-51-3 Cyclosiversioside G 
• 148297-88-5 cycloaraloside D 
• 83207-58-3 astragaloside IV 

Downstream Products

• 84687-42-3 astragaloside III 
• 1255151-96-2 2-(L)-amino-3-phenyl-propionic acid 6α,16β-dihydroxy-17-[5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydrofuran-2-yl]-4,4,13,14-tetramethyl-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3α-yl ester hydrochloride 
• 1255152-17-0 2-(L)-amino-3-phenyl-propionic acid 3β,16β-dihydroxy-17-[5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-4,4,13,14-tetramethyl-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-6α-yl ester hydrochloride 
• 1255152-16-9 C₄₄H₆₇NO₈ 
• 1255151-95-1 C₄₄H₆₇NO₈ 
• 1255151-99-5 C₃₇H₅₄O₆ 
• 11026-01-0 20(S),24(R)-epoxylanost-9(11)-ene-3β,6α,16β,25-tetraol 
• 86541-79-9 astragenol 

Relevant articles and documents

Structure of cyclochivinoside C from Astragalus chivensis

The new cycloartane glycoside cyclochivinoside C, 24S-cycloartan-3β, 6α,16β,24,25-pentaol 3,16-di-O-β-D-glucopyranoside, was isolated from the aerial part of Astragalus chivensis. The structures of the isolated compounds were established by chemical transformations and PMR and 13C NMR spectra.

The use of two-phase acid hydrolysis method of preparing ring [...] (by machine translation)

The invention belongs to the field of pharmaceutical chemicals, in particular to the use of double-phase acid hydrolysis method of preparing ring [...], including astragaloside as raw materials, and the organic phase and the acid solution of the two-phase acid aqueous solution mixing, reaction, after-treatment, to obtain the ring [...]; wherein organic phase immiscible with water or slightly soluble, ring [...] in the organic phase is greater than the solubility of the aqueous phase. This invention utilizes the double-phase acid hydrolysis method for preparing ring [...], making acid is hydrolyzed to generate ring [...] distribution in the organic phase, thereby avoiding the ring [...] in violent acid aqueous phase into the shortcoming of the [...], effectively protect the stability of the ring [...], [...] greatly improves the yield of the ring, and the step is simple, low cost, and is suitable for industrial production; through the standstill, layered, extraction, silica gel column chromatography separation to obtain high-purity [...]. (by machine translation)

Flavonoid and cycloartane glycosides from seeds of Koelreuteria paniculata

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Biocatalysis of cycloastragenol by filamentous fungi to produce unexpected triterpenes

The biocatalysis of cycloastragenol, a natural tetracyclic triterpenoid with anti-aging activity, by cultured whole cells of three strains of filamentous fungi, namely Cunninghamella elegans AS 3.1207, Syncephalastrum racemosum AS 3.264 and Doratomyces stemonitis AS 3.1411 produced 15 metabolites. Thirteen of them are new compounds. The structures of these metabolites were fully characterized on the basis of HR-ESI-MS analyses together with 1D and 2D NMR spectroscopy. The three fungal strains exhibited significant biocatalytic preferences: C. elegans enabled hydroxylation reactions, particularly on the 28- and 29-CH3 groups; S. racemosum efficiently catalyzed a complicated rearrangement reaction to form the unusual ranunculane skeleton, which was further substituted with diverse side chains at C-19; D. stemonitis mainly led to carbonylation reactions, especially on 3-OH. It is particularly noteworthy that S. racemosum also catalyzed an unexpected ring expansion reaction to generate the rare 9(10)a-homo-19-nor-cycloartane skeleton. Biocatalysis was proved powerful in the structural diversification of cycloastragenol for future structure-activity relationship studies. Copyright