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

A steroidal saponin and furan ring technology, applied in the field of medicinal chemistry, 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: 2006-02-01
CHENGDU DIAO JIUHONG PHARMA FACTORY
View PDF0 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Dioscin generally has the disadvantages of po

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 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

[0018] 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).

[0019] Take 500g of total dioscin saponins, disperse it in 5000ml of water, and sequentially extract with ethyl acetate (3500ml×4) and n-butanol (3500ml×5) to obtain ethyl acetate extract (45g) and n-butanol extract (230g). The fraction of n-butanol was subjected to silica gel column chromatography with chloroform-methanol-water (9:1:0.1-0:1:0.1) gradient elution, and was divided into 20 fractions. Take the 17th component (40g) and divide it into 5 sections with resin MCI, take the 4th section (2.8g) and separate it with silica gel column chromatography, elute with chloroform-methanol / 4:1, and finally pass through a reversed-phase silica gel column Purification by chromatography afforded compound 1 (15 mg).

[0020] m.p.186-188°C.

[0021] [α] D 22 ...

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 -D-Glucopyranoside (compound 1) mixed with dilute hydrochloric acid to prepare 26-O-β-D-glucopyranosyl-3β, 20α, 26-triol-25(R)-Δ 5，22(23) -diene-furosta-3-O-α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl (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. 1 H NMR (400MHz, C 5 D. 5 N): δ H 6.40 (1H, br s, l-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, l-H-glc'), 3.93 (1H, m, 26-H), 3.65 (1H, m, 26-H), 1.75 (3H, d, J = 6.4Hz, rha-CH 3...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

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 application. 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 sapo...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
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 JIUHONG PHARMA FACTORY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap