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Steroid saponin of alpha, beta double bond structure outside furan nucleus, preparation method and application

A steroidal saponin and carrier technology, which is applied in the preparation of drugs for the treatment of cardiovascular diseases. In the field of compounds, it can solve the problems of poor solubility and low bioavailability, and achieve the effects of reducing weight, reducing infarct size, and inhibiting platelet aggregation.

Active Publication Date: 2010-05-12
CHENGDU DIAO JIU HONG PHARMACEUTICAL FACTORY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Dioscin generally has the disadvantages of poor solubility and low bioavailability in vivo

Method used

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  • Steroid saponin of alpha, beta double bond structure outside furan nucleus, preparation method and application
  • Steroid saponin of alpha, beta double bond structure outside furan nucleus, preparation method and application
  • Steroid saponin of alpha, beta double bond structure outside furan nucleus, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1 26-O-β-D-glucopyranosyl-3β, 20α, 26-triol-25(R)-Δ 5，22 -Diene-furostan-3-O-{[α-L-rhamnopyranosyl(1→2)]-[α-L-rhamnopyranosyl(1→4)]-β- Isolation and structure identification of D-glucopyranoside (compound 1).

[0018] Take 500g of total dioscin saponins, disperse in 5000ml of water, and extract with ethyl acetate (3500ml×4) and n-butanol (3500ml×5) in sequence to obtain ethyl acetate extract (45g) and n-butanol extract (230g). The n-butanol fraction was subjected to silica gel column chromatography, chloroform-methanol-water (9:1:0.1-0:1:0.1) gradient elution, and was divided into 20 components. The 17th component (40g) was taken , divided into 5 sections by resin MCI, and the fourth section (2.8g) was separated by silica gel column chromatography, eluted with chloroform-methanol / 4:1, and finally purified by reverse phase silica gel column chromatography to obtain compound 1 (15mg) .

[0019] m.p.186-188°C.

[0020] [α] D 22 -twenty three 0 (0.06, methano...

Embodiment 2

[0041] Example 2 3β, 20α, 26-triol-25(R)-Δ 5，22(23) Preparation of -diene-furostan-26-O-β-D-glucopyranoside

[0042] 26-O-β-D-glucopyranosyl-3β, 20α, 26-triol-25(R)-Δ 5，22 -Diene-furostan-3-O-{[α-L-rhamnopyranosyl(1→2)]-[α-L-rhamnopyranosyl(1→4)]-β- D-Glucopyranoside (compound 1) was mixed with dilute hydrochloric acid, reacted at 60°C for 40 hours, the reaction pH was 6.2, and then extracted with ethyl acetate, evaporated to dryness under reduced pressure to obtain 3β, 20α, 26-tri Alcohol-25(R)-Δ 5，22(23) -diene-furosta-26-O-β-D-glucopyranoside (compound 3).

[0043] ESI-MS:

[0044] 615[M+Na] +

[0045] 591[M-H] -

[0046] 429[M-H-glc] -

[0047] IR(KBr): 3432 (broad, associative multi-OH), 2926 (CH 2 ), 1634 (CH 3 ), 1450, 1386, 1040-1055, 913, 889. 1 H NMR (400MHz, C 5 D. 5 N): δ H 4.81 (1H, d, J=7.9Hz, 1-H-glc'), 3.96 (1H, m, 26-H), 3.64 (1H, m, 26-H), 1.72 (3H, s, 21-CH 3 ), 1.02 (3H, d, J=10.8Hz, 27-CH 3 ), 1.00 (3H, s, 19-CH 3 ), 0.85 (3H, s, 18-CH ...

Embodiment 3

[0049] Example 3 26-O-β-D-glucopyranosyl-3β, 20α, 26-triol-25(R)-Δ 5，22(23) Preparation of -diene-furosta-3-O-α-L-rhamnopyranosyl (1→2)-β-D-glucopyranosyl

[0050] According to the method similar to Example 2, 26-O-β-D-glucopyranosyl-3β, 20α, 26-triol-25(R)-Δ 5，22 -Diene-furostan-3-O-{[α-L-rhamnopyranosyl(1→2)]-[α-L-rhamnopyranosyl(1→4)]-β- Mixed reaction of D-glucopyranoside (compound 1) and dilute hydrochloric acid to prepare 26-O-β-D-glucopyranosyl-3β, 20α, 26-triol-25(R)-Δ 5，22(23) En-furosta-3-O-α-L-rhamnopyranosyl(1 → 2)-β-D-glucopyranoside (Compound 4).

[0051] ESI-MS:

[0052] 901[M+H] +

[0053] 899[M-H] -

[0054] 753 [M-H-rha] -

[0055] IR (KBr): 3436 (broad, associative multi-OH), 2926 (CH 2 ), 1632 (CH 3 ), 1385, 1039-1054, 910, 886.

[0056] 1 H NMR (400MHz, C 5 D. 5 N): δ H 6.40 (1H, br s, 1-H-rha″’), 5.28 (1H, br s, 6-H), 5.05 (1H, d, J=6.8Hz, 1-H-glc″), 4.83 (1H , d, J = 7.7Hz, 1-H-glc'), 3.93 (1H, m, 26-H), 3.65 (1H, m, 26-H), 1.75 (3H, d,...

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Abstract

A steroid saponin with alpha and beta double-bond structure outside furan ring, its preparing process and its application for preparing medicines to treat cardiovascular disease are disclosed.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry. The present invention relates to a novel compound, its preparation method and use. Specifically, it relates to a steroidal saponin with a double bond structure outside the furan ring, its preparation method and the application of the compound in the preparation of drugs for treating cardiovascular diseases. Background technique [0002] Steroidal saponins (steroidal saponins) are a class of important chemical components in natural products, most of which have certain physiological activities, and their aglycones are the main raw materials for the synthesis of steroidal contraceptives and hormone drugs. According to incomplete statistics, more than 90 families of plants contain steroidal saponins. (Dai Zhong. Research progress of steroidal saponins. Chinese Pharmacist, 2003, 6 (10): 615-616) According to Peng Junpeng's report, as of 1990, more than 400 kinds of steroidal saponins hav...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J71/00A61K31/7048A61P9/00
Inventor 付铁军陈洪超刘忠荣廖循丁立生彭树林李伯刚
Owner CHENGDU DIAO JIU HONG PHARMACEUTICAL FACTORY