Application of triterpenoid saponin compound in preparation of medicaments for treating autoimmune diseases
A technology of triterpene saponins and autoimmunity, which is applied in bone diseases, drug combinations, allergic diseases, etc., and can solve the problems of non-specific immunosuppression of the body, large side effects, and no specific treatment methods.
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[0051] The synthetic method of the triterpene saponin compound shown in the above general chemical formula I specifically comprises the following steps:
[0052] Step 1: protecting the hydroxyl group of the five- or six-membered sugar or its derivative; reacting trichloroacetonitrile or mercaptan with the hemiacetal hydroxyl group of the hydroxyl-protected sugar or its derivative to obtain at least one compound A standby;
[0053] Step 2: reacting triphenylchloromethane with oleanolic acid or ursolic acid to obtain compound B for later use;
[0054] Step 3: reacting at least one compound A with compound B and deprotecting with sodium alkoxide to give R 5 A compound of general chemical formula I which is a hydrogen atom; or
[0055] reacting at least one compound A with compound B, and deprotecting with acetic acid, then reacting with at least one compound A prepared in step 1, and then deprotecting with sodium methoxide, wherein the at least one compound A can be same or ...
Embodiment 1
[0079] Example 1 Synthesis of oleanolic acid 3-O-α-L-rhamnopyranose
[0080] The natural products α-L-rhamnopyranose (compound 1, purchased from Kebosi Biotechnology Co., Ltd.) and oleanolic acid (compound 5, purchased from Xi'an Guanyu Biotechnology Co., Ltd.) were used as starting materials. The synthesis is carried out according to the reaction scheme shown below.
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[0083] Specifically, 20 g of compound 1 (α-L-rhamnopyranose) was stirred under an ice bath, 75 ml of benzoyl chloride (BzCl) was dissolved in 150 ml of pyridine (Pyr) as solvent I, and slowly dropped into the above solution , stirred overnight at room temperature, and after the completion of the reaction was detected by thin-layer chromatography, it was concentrated under reduced pressure and purified and separated by column chromatography (petroleum ether / ethyl acetate=5 / 1) to obtain compound 2 (33.8 g). Compound 2 was dissolved in a mixed solvent of tetrahydrofuran (THF) and methanol (...
Embodiment 2
[0091] Example 2 Synthesis of oleanolic acid 3-O-α-L-rhamnopyranose 28-O-α-L-rhamnopyranoside
[0092] Compound 7 and Compound 4 obtained in Example 1 were used as starting materials. The synthesis is carried out according to the reaction scheme shown below.
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[0094] Compound 8 (8 g) obtained in Example 1 was added with 20 ml of 80% acetic acid, and stirred at 70° C. for 2 hours. After the reaction was complete after detection by thin layer chromatography, it was concentrated under reduced pressure and analyzed by column chromatography (petroleum ether / ethyl acetate). Ester=7 / 1) was purified and separated to obtain compound 9 (6.4 g).
[0095] Under nitrogen protection, compound 9 (4g) and compound 4 (2.3g) were dissolved in 100ml of dichloromethane as solvent II, 1.1g of N-iodosuccinimide was added with stirring at room temperature, and the temperature was lowered to -40°C~ -50°C, add 100 μl of trimethylsilyl trifluoromethanesulfonate, stir at -35°C to -45°C for...
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