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Phosphate ester derivative of herba epimedii as well as preparation method and application of phosphate ester derivative

A technology of phosphates and epimedium, applied in the field of phosphate derivatives of epimedium and its preparation, can solve the problems of obvious side effects and restriction of drug use, and achieve simple preparation process, low cost, and enhanced cytotoxicity Effect

Active Publication Date: 2021-06-25
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, modern medicine mainly uses bisphosphonates, calcitonin, fluoride and hormone replacement therapy for the treatment of osteoporosis, but the curative effect is controversial, and the side effects are obvious, which limits the use of drugs

Method used

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  • Phosphate ester derivative of herba epimedii as well as preparation method and application of phosphate ester derivative
  • Phosphate ester derivative of herba epimedii as well as preparation method and application of phosphate ester derivative
  • Phosphate ester derivative of herba epimedii as well as preparation method and application of phosphate ester derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] 3,5,7-Trihydroxy-8-(3-methyl-2-butenyl)-2-(4-methoxyphenyl)-7-(4H-benzopyran-4-one) (Icariin), the structure of icariin is shown below:

[0035]

[0036] Since icariin is less present in Epimedium, icariin is extracted and isolated from the traditional Chinese medicine Epimedium, mainly obtained by hydrolyzing icariin. Icariin uses icariin as raw material, and is hydrolyzed by immobilized α-L-rhamnosidase and glucosidase. Take 5 g of icariin and add 50 mL of deionized water to a 250-mL round-bottomed flask, place it in a constant temperature water bath shaker at 60 °C, adjust the pH to 9-10, and add immobilized α-L-rhamnosus after the substrate is dissolved. 1 g of glycosidase and 1 g of glucosidase were reacted for 3 hours at an oscillation frequency of 120 r / min, monitored by TLC, after the reaction of the raw materials was completed, the pH was adjusted to 3-4, the filtrate was placed in a refrigerator until it was precipitated, and the epimedium was obtained by ...

Embodiment 2

[0040] 3,5-Dihydroxy-8-(3-methyl-2-butenyl)-2-(4-methoxyphenyl)-7-(4H-benzopyran-4-one)phosphoric acid bis The structural formula of methyl ester is:

[0041]

[0042]3,5,7-trihydroxy-8-(3-methyl-2-butenyl)-2-(4-methoxyphenyl)-7-(4H-benzopyridine) synthesized in Example 1 Furan-4-one) (icariin) (193 mg, 0.5 mmol) was dissolved in 20 mL of tetrahydrofuran, and the catalysts were added diisopropylethylamine (DIPEA, 0.348 mL, 2 mmol) and 4-dimethylaminopyridine (DMAP, 6 mg) , 0.05mmol), cooled to 0°C in an ice-water bath, slowly added CCl of dimethyl phosphite (46uL, 0.5mmol) 4 (2 mL), slowly raised to 20°C, and the reaction was monitored by thin layer chromatography (methanol:dichloromethane=1:10). After the reaction was completed, it was concentrated under reduced pressure, and purified by column chromatography (silica gel column purification) to obtain the target compound 3,5-dihydroxy-8-(3-methyl-2-butenyl)-2-(4-methyl) Oxyphenyl)-7-(4H-benzopyran-4-one) dimethyl phosph...

Embodiment 3

[0046] 3,5-Dihydroxy-8-(3-methyl-2-butenyl)-2-(4-methoxyphenyl)-7-(4H-benzopyran-4-one)phosphoric acid bis The structural formula of ethyl ester is:

[0047]

[0048] 3,5,7-trihydroxy-8-(3-methyl-2-butenyl)-2-(4-methoxyphenyl)-7-(4H-benzopyridine) synthesized in Example 1 Furan-4-one) (icariin) (193 mg, 0.5 mmol) was dissolved in tetrahydrofuran (20 mL), and the catalysts were added diisopropylethylamine (DIPEA, 0.348 mL, 2 mmol) and 4-dimethylaminopyridine (DMAP). , 6 mg, 0.05 mmol), cooled to 0 °C in an ice-water bath, and slowly added diethyl phosphite (64 uL, 0.5 mmol) in CCl 4 (2 mL), slowly warmed to 20°C, and the reaction was monitored by thin layer chromatography (methanol:dichloromethane=1:10). After the reaction was completed, the reaction was concentrated under reduced pressure, and purified by column chromatography (silica gel column purification) to obtain the target compound 3,5-dihydroxy-8-(3-methyl-2-butenyl)-2-(4-methoxy phenyl)-7-(4H-benzopyran-4-one) d...

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Abstract

The invention belongs to the technical field of medicines, and discloses a phosphate ester derivative of herba epimedii as well as a preparation method and application of the phosphate ester derivative. The chemical structural formula of the phosphate ester derivative of the herba epimedii is represented by the formula (1), wherein R1 is selected from groups defined in the specification, or R2 is selected from H or R1, and R3 is selected from H or a group defined in the specification. According to the phosphate ester derivative of the herba epimedii, the cytotoxicity of the partially modified derivative is remarkably enhanced compared with that of an unmodified derivative, and meanwhile the phosphate ester derivative of the herba epimedii has the anti-osteoporosis effect. The phosphate ester derivative of the herba epimedii can be applied to the field of preparation of drugs for prostate cancer cells, anti-osteoporosis health-care products, pharmaceutical excipients or drugs.

Description

technical field [0001] The invention belongs to the technical field of medicine, and more particularly relates to a phosphate derivative of Epimedium, a preparation method and application thereof. Background technique [0002] Epimedium is a traditional Chinese herbal medicine, also known as Xianlingpi, and Epimedium of Berberiaceae. Epimedium has the functions of invigorating kidney and strengthening yang, strengthening muscles and bones, expelling wind and removing dampness, etc. It is a traditional Chinese herbal medicine used in traditional Chinese medicine to treat osteoporosis. Wine, boiled paste, and pill-making powder, etc. At present, the treatment of osteoporosis in modern medicine mainly uses bisphosphonates, calcitonin, fluoride and hormone replacement therapy, etc., but the efficacy is controversial, and the side effects are obvious, which limits the use of drugs. Traditional Chinese medicine has a long history in the treatment of osteoporosis in my country, a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/655A61P35/00A61P19/10A23L33/105
CPCC07F9/65522A61P35/00A61P19/10A23L33/105A23V2002/00A23V2200/306A23V2200/308A23V2250/21
Inventor 郭成龙黄宝华卢宇靖黎志豪刘傲璐黄嘉丽左珊珊
Owner GUANGDONG UNIV OF TECH
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