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Toad sterene compounds and application thereof in pharmaceutical preparation

A technology of bufastene and compound, applied in the field of medicinal chemistry and its preparation, can solve the problems of low anti-tumor cell activity, low water solubility and the like

Active Publication Date: 2007-08-15
ANHUI CHINA RESOURCES JINCHAN PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The technical problem to be solved by the present invention is to provide a class of bufasterene compounds and their application in drug preparation, so as to overcome the defects of low water solubility and low anti-tumor cell activity of existing bufasterene compounds in in vitro experiments

Method used

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  • Toad sterene compounds and application thereof in pharmaceutical preparation
  • Toad sterene compounds and application thereof in pharmaceutical preparation
  • Toad sterene compounds and application thereof in pharmaceutical preparation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Extraction and separation of the toad poison substrate: the toad venom extract is dissolved in water to form 10 liters of homogenized samples, extracted with chloroform (10 L x 4 times), the chloroform extract is dissolved in a small amount of chloroform acetone, mixed with 3 times the amount of silica gel, and removed The solvent, after being completely dried, was loaded into a silica gel column. The silica gel column has a diameter of 4.5 cm and a length of 60 cm. The silica gel pH 5.3 has a particle size of 100-200 mesh. For elution, the eluent is acetone-cyclohexane (1:5) eluent with different gradients. Collected in sections, fractions 5-10 were obtained to obtain Cinobufagin, fractions 11-13 to obtain Cinobufagin, fractions 14-15 to obtain Cinobufen essence and bufalin, fractions 16-20 to obtain toad Toad spirit, fraction 33-35 get toad toad spirit. Fractions 36-42 Deyuan Cinobufina Toxin. A small amount of cinobufagin and bufafolin in fractions 14-15 were fur...

Embodiment 2

[0062] Obtaining of bufasterene compounds:

[0063] Pre-experiment: add bufafolin, bufabugenin, cinobufagin, bufabufalin and bufafolin to the suspension culture medium of periwinkle cells, at 25°C for 12 hours Co-cultured under light conditions, extracted with ethyl acetate, concentrated, dissolved in a small amount of acetone. Petroleum ether: Acetone is used as a developing solvent, 10% sulfuric acid alcohol is used for color development at 120° C., and the results are analyzed by TLC (silica gel G, 0.3% CMC-Na binder).

[0064] Transformation product amplification: 15 mg / mL of mixed bufotoxin substrate containing bufalin, bufabugenin, cinobufagin, bufabufalin and bufafetoxin was put into the suspension cell liquid of Changchun flower, and the culture medium It is MS+NAA0.5mg / L+6-BA0.5mg / L+sucrose 3%, pH5.8. Co-cultivate at 25°C for 12 hours under light or dark conditions, extract with ethyl acetate, concentrate, combine and recover.

Embodiment 3

[0068] MTT method was used to measure the cytotoxic activity of 3-epi-bufalin 3-O-β-D-glucoside: HL-60 cell line was cultured in 20% RPMI 1640 medium, and the cell density was adjusted to 0.5×10 5 / mL, planted in a 96-well plate, bufalin and the transformation product were dissolved in methanol, according to the blank, methanol control, bufalin (10mg / L, 1mg / L, 0.5mg / L, 0.1mg / L, 0.05 mg / L), 3-epi-bufalin 3-O-β-D-glucoside (10mg / L, 1mg / L, 0.5mg / L, 0.1mg / L, 0.05mg / L) design concentration added to HL The -60 cell line was cultured in a CO2 incubator for 44 hours and MTT was added, and SDS was added for 48 hours to terminate the reaction.

[0069] Bufalin and 3-table-bufalin 3-O-β-D-glucoside inhibit the leukemia HL-60 cell line results are shown in Table 1, and the analysis of variance in Table 2 shows that 3-table-bufalin Compared with bufalin, 3-O-β-D-glucoside has significantly improved cytostatic activity.

[0070] Table 1 The colorimetric results of the inhibition of bufali...

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Abstract

The invention discloses a 3-epi-bufalin 3-O-beta-D-glucoside and derivant, which inhibits cancer cell from growing rather than bufalin to make cardiotonic, local anesthesia, combat shock and tumour-resistant drug.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry and its preparation, and specifically relates to a class of steroid compounds. Background technique [0002] Bufasterene is a class of steroidal compounds in which the C-17 position is linked to a six-membered unsaturated lactone ring (α-pyrone ring). Natural bufasterene A / B rings are cis or trans fused, and B / C rings are all trans, but unlike general steroids, its C / D rings are cis fused. In addition to most of the hydroxyl groups at the C-3 position, bufasterene often has oxygen-containing substitutions at the 5β-, 6β-, 11α-, 12α- / β-, 14β-, 16β- and 19-positions (mostly hydroxyl or acetoxy group), and some form a three-membered oxygen ring at the 14β, 15β-position. Some 19-positions are oxidized to aldehyde groups, and some C-19 is absent. Δ4,5 is the most common double bond in the molecule, and there are also Δ14,15, Δ3,4 and Δ6,7, etc. Some of C-12 are substituted by carbonyl, ...

Claims

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Application Information

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IPC IPC(8): C07J19/00C07J71/00A61P31/12A61P35/00A61K9/08A61K9/20A61K9/48
Inventor 赵军果德安李孔敏
Owner ANHUI CHINA RESOURCES JINCHAN PHARMA CO LTD
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