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Bisbenzylisoquinoline compounds, preparation method and applications

A technology of bisbenzylisoquinoline and compounds, applied in the field of medicine, can solve problems such as no reports of anti-tumor cytotoxic activity

Inactive Publication Date: 2008-10-15
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, no bisbenzylisoquinoline alkaloids have been found in black medicine, let alone the anti-tumor cytotoxic activity of such alkaloids in black medicine

Method used

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  • Bisbenzylisoquinoline compounds, preparation method and applications
  • Bisbenzylisoquinoline compounds, preparation method and applications
  • Bisbenzylisoquinoline compounds, preparation method and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] The physicochemical and UV, IR, MS spectral data of embodiment 1 compound I are as follows:

[0015] Compound I is a pale yellow solid, [α] D 20 -16°(c 1.0, MeOH); electrospray mass spectrometry (ESIMS) (positive ion type positive) m / z 595[M+H] + (100); (negative ion negative) m / z 593(100); UV(MeOH)λ max nm(logε): 207(5.30), 288(4.87); IR(KBr)v max cm -1 3405, 2937, 2842, 1664, 1588, 1510, 1450, 1371, 1276, 1228, 1135, 1028, 756.

[0016] Compound I 1 H NMR, 13 C NMR data and their assignments are shown in Table 1. The assignments of each hydrogen and carbon signal were obtained by testing two-dimensional NMR spectra (carbon-hydrogen correlation spectrum, carbon-hydrogen long-range correlation spectrum, nuclear Overhauser effect two-dimensional correlation spectrum).

[0017] Table 1. Compound I 1 H(400MHz) and 13 C (100MHz) NMR data and signal attribution (CD 3 OD solvent)

[0018] no

[0019] 14′

Embodiment 2

[0021] Cut 5kg of dried root tubers of black medicine into thin slices, add 50L ethanol after crushing, and extract twice by percolation. After combining the two extracts, concentrate under reduced pressure to obtain the extract, suspend and dissolve the extract with 10L of water, and dissolve the extract with 2N HNO 3 After acidification, it was extracted three times with an equal volume of ethyl acetate, and the ethyl acetate layer was discarded after recovering the solvent. 5% Na for the aqueous phase 2 CO 3 Adjust the pH to 10, extract twice with an equal volume of ethyl acetate, combine the ethyl acetate extracts, wash with distilled water until neutral, and recover ethyl acetate under reduced pressure to obtain 32.3 g of crude total alkaloids. Dissolve the crude product in 3L of ethanol, add water to make the ethanol content 60%, let it stand for complete precipitation, filter and dry to obtain 12.8g of refined total alkaloids.

[0022] Take the above-mentioned refine...

Embodiment 3

[0024] Cut 3kg of dried root tubers of black medicine into thin slices, add 30L methanol after crushing, and reflux extraction twice, the first time is 2 hours, after the extract is filtered, add 24L methanol to continue reflux extraction for 1 hour. The two extracts were combined and then concentrated under reduced pressure to obtain an extract, which was suspended and dissolved in 6 L of water, acidified with 3N HCl, extracted three times with an equal volume of chloroform, and the chloroform layer was discarded after recovering the solvent. The pH of the aqueous phase was adjusted to 10 with ammonia water, extracted twice with an equal volume of chloroform, the combined chloroform extracts were washed with distilled water until neutral, and 21.7 g of crude total alkaloids were obtained after recovering the chloroform under reduced pressure. Dissolve the crude product in 3L of methanol, add water to make the methanol content 50%, let it stand for complete precipitation, filte...

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Abstract

The invention provides a bisbenzylisoquinoline compound in lindera aggregate and the preparation method thereof. The lindera aggregate dried root is used as the raw material and is extracted by using an alcoholic solvent, the extractant is produced into extracturm through decompressing concentration, after the extracturm is dissolved and suspended by water and acidified by dilute acid, the neutral component of the extracturm is removed by extraction with an organic solvent, the water phase is adjusted to the pH value of 10 by weak base, extraction is performed by the organic solvent after solvent recovery, the total alkaloid crude product is obtained, fine alkaloid crude is prepared after the crude product is resolved in alcohol and sedimentation process is performed by adding an amount of water, eluting parts are colleted after the chloroform-carbinol system elution and the water-carbinol gradient elution, and the compound can be prepared after removing the solvent by condensation. The compound is used for performing activity inhibition experiments to L1210 and K562 tumor cell strains, results show that both L1210 and K562 tumor cell strains have strong cell-toxicant activity and present dose-effect relationships. The compound can be applied to the preparation of anticancer drugs, and has the above structural formula.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a method for preparing a new bisbenzylisoquinoline alkaloid from traditional Chinese medicine wuyao and its application in the preparation of antitumor drugs. Background technique [0002] Wuyao is a commonly used traditional Chinese medicine. It is one of the important medicines for warming the stomach, regulating qi and relieving pain. Modern research has found that the chemical composition of black medicine is complex, rich in furosesquiterpenes and their lactones, flavonoids, volatile oils, isoquinoline alkaloids, etc. Improve central nervous system function, anti-inflammatory and analgesic, prevent and treat diabetic nephropathy, protect liver, regulate blood coagulation function and other pharmacological effects. The alkaloids contained in black medicine are mostly isoquinoline alkaloids, among which laureolistine, boldine and reticuline are the main three iso...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/12A61K36/54A61K31/4725A61P35/00
Inventor 甘礼社吴理茂周长新
Owner ZHEJIANG UNIV
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