Introduction:
Cycloastraganol was patented by Geron Corporation and sold in early 2013 to Telomerase Activation Sciences, which is developing a product called TA-65.
Cycloastragenol is derived from the dried roots of the leguminous plant Astragalus membranaceus (Fisch.) Bge. var. mongholicus (Bge.) Hsiao. It is a natural tetracyclic triterpenoid compound that was identified as having anti-aging properties when screening Astragalus extracts. active. Cycloastragenl is an effective telomerase activator. Cycloastragenol also has other pharmacological effects, including anti-inflammatory and antioxidant properties.
Cycloastraganol is also a food-grade product. It is mainly a brown or light yellow and pure white powder. The color will change depending on the purity. Generally, the highest purity can reach 98%. The lightest color is pure white. The color of cycloastraganol is pure white powder. If you choose brownish-yellow purity, the purity can reach 5% and 10%. If the purity is between 50%6-90%6, the color will be light yellow powder, so the overall The color or purity will be different.
CAS No:84605-18-5
Molecular formula: C30H50O5
Molecular weight: 490.71
Boiling point:617.2±55.0°C(Predicted)
Density:1.20
Shipping conditions: ice pack shipping
Specific rotation: 49° (C=1.37, MeOH)
Solubility: Soluble in ethanol, dimethyl sulfoxide and dimethylformamide, but insoluble in water.
Storage conditions: should be stored in a dry, cool place, away from fire and high temperature.
Acidity coefficient (pKa) 14.57±0.29 (Predicted)
effect:
Cycloastraganol (CAG) is the aglycone of astragaloside IV and is the only reported telomerase activator among natural products. It can effectively combat telomere shortening and has anti-aging, anti-apoptosis, anti-fibrosis, and immune functions. It has pharmacological effects such as regulating and promoting cell proliferation and wound healing, thus having potential therapeutic effects on diseases related to telomere dysfunction.
Cycloastragenol is very good for diuresis or detoxification, muscle growth and sore healing. In addition, it can regulate the body's immune ability and has anti-inflammatory, anti-oxidative or anti-ischemic brain damage and anti-aging effects. It has a very good effect. Cycloastragenol has certain auxiliary treatment effects on chronic renal failure or secondary kidney disease, and it can also prolong life. There are also many derivatives of astragalus on the market, and they have many uses. In addition, they are helpful in anti-virus or protecting lung damage and anti-depression, so clinical research or use are becoming more and more widespread.
market outlook:
At present, the source of cycloastragalin monomer is expensive, and it has problems such as poor water solubility, short metabolism time, and low oral bioavailability, which limits its clinical application. In the future, based on its good pharmacological effects and research value, its chemical structure modification, total synthesis, biosynthesis and other research will have important development value.
Production Process:
Preparation process method 1: Use acid hydrolysis method to prepare cycloastraganol. An oxidation reaction is performed before hydrolysis. Through the oxidation reaction, the sugar in astragaloside IV can be partially oxidized to open the chain, which facilitates subsequent hydrolysis reaction removal without affecting the glycosides. element part, thereby increasing the yield of cycloastragalinol. The process flow is: oxidation-reduction-hydrolysis-extraction. The specific operations are as follows: Oxidation and reduction: Take 800 mg of astragaloside IV as raw material, add water to prepare a 0.01mol/L astragaloside IV suspension, and add HCl to adjust the suspension. The pH reaches 4. Add KIO4 to the suspension and react in the dark at 20°C for 48 hours. Then add ethylene glycol to terminate the oxidation. Then add Na2CO3 to pH 7. Concentrate under reduced pressure until there is no alcohol smell. Add an equal volume of n-butanol for extraction. 3 times, combine the n-butanol extraction part, wash with water 2 times, take the n-butanol part, evaporate the n-butanol, and obtain the oxidation product. Add 30% methanol aqueous solution to the oxidation product to disperse into a suspension, in which 30% The mass ratio of the methanol aqueous solution to astragaloside IV is 1:1; then add BH4Na as the reducing agent. After the reduction reaction for 24 hours, add 50% acetic acid to the pH of the reaction solution to 5 to terminate the reaction, and the reduction product is obtained.
Hydrolysis and extraction: Add an appropriate amount of H2SO4 to the reduction reaction solution, and let the reaction stand for 24 hours at 50°C. Add K2CO3 to the hydrolyzed reaction solution, adjust the pH to 7, and then extract three times with ethyl acetate of the same volume as the reaction solution, and combine The ethyl acetate extract was concentrated under reduced pressure to dryness to obtain crude cycloastragalin. Refining: Dissolve the crude cycloastraganol with an appropriate amount of CH2Cl2-acetone, then place it at 10°C for 24 hours, crystallize, filter and dry to obtain the fine product. Method 2: A method for preparing cycloastragalinol, including the following steps: oxidation: adding astragaloside IV to a solvent to prepare a suspension with an astragaloside IV content of 0.001-0.05 mol/L; adding acid to adjust the pH of the suspension to 3-6, add oxidant to the suspension, react in the dark at 5-35°C for 12-96 hours, then add ethylene glycol to terminate the oxidation, where the molar ratio of astragaloside IV to oxidant is 1:2-1 :15; then add alkali to adjust the pH to 7-10, concentrate under reduced pressure until there is no alcohol smell, and then filter or extract to obtain the oxidation product; reduction: add the obtained oxidation product to a solvent to disperse it into a solution or suspension; the added solvent The mass ratio to astragaloside IV in step A is 1:0.7-1:40; then add sodium borohydride or potassium borohydride as a reducing agent. After the reduction reaction for 12-48 hours, add acetic acid or acetic acid aqueous solution to adjust the pH of the reaction solution. to 4-6 acidity to terminate the reduction reaction; wherein the molar ratio of the reducing agent to astragaloside IV in step A is 1:2-1:8;
Hydrolysis: Add strong acid to the reaction solution, and let it stand or stir for 6-96 hours at 10-60°C; the mass ratio of the added strong acid to the reaction solution is 0.5-3:100; extraction; add alkali, Adjust the pH to neutral, and then extract 3-5 times with an equal volume of ethyl acetate as the reaction solution. Combine the ethyl acetate extracts and concentrate to dryness under reduced pressure to obtain crude cycloastragalinol. Purification: Purify the obtained crude cycloastragalinol using one or more methods of normal phase silica gel column chromatography, reversed phase silica gel column chromatography, and recrystallization to obtain cycloastragalinol.
application
1. Anti-aging: A telomerase activator, which delays the shortening of telomeres by increasing telomerase and plays an anti-aging effect.
2. Application in the preparation of anti-cancer auxiliary treatment drugs: anti-cancer auxiliary treatment drugs prepared with it as the active ingredient of the drug can enhance the efficacy of anti-cancer drugs, reduce the toxicity of anti-cancer drugs, and prevent and treat diseases caused by anti-cancer drug treatment. The anticancer adjuvant therapeutic effect of leukopenia.
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