Purification of cinnamoyl-C-glycoside chromone

a technology of cinnamoyl cglycoside and chromone, which is applied in the field of purification of cinnamoyl cglycoside chromone, can solve the problems of process failure to yield compound 540 of sufficient purity, and conventional methods fail to take into accoun

Inactive Publication Date: 2002-06-25
UNIGEN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention includes a process for isolating and purifying the cinnamoyl-C-glycoside, .[.8-C-.beta.-D-[2-O-(E)-cinnamoyl]glycopyranosyl-2-[(R)-2-hydroxy]propyl- 7-methoxy-5-methyl-chromone.]. .Iadd. 8-C-.beta.-D-[2'-O-(E)-cinnamoyl]glycopyranosyl-2-[(S)-2-hydroxy]propyl-7- methoxy-5-methylchromone .Iaddend.from the aloe plant. In one embodiment of the present invention, the method comprises: contacting a decolorizing agent, which has been obtained from the processing of a slurry of an aloe leaf extract, with an organic solvent to extract the absorbed 540 compound from the decolorizing agent into the organic solvent, thereby forming a mixture of decolorizing agent and organic solvent containing the 540 compound; separating the decolorizing agent from the organic solvent to yield a solution highly enriched in compound 540. Optionally, the 540 compound is further purified using reversed phase high pressure liquid chromatography (HPLC) or by conventional chromatographic methods, such as column chromatography.

Problems solved by technology

As explained by McAnnalley, conventional methods fail to take into account that the three separate segments of the aloe leaf--the gel fillet, leaf rind and yellow fluid or latex--have varied compositions containing compounds which may be inconsistent with the intended use of the final composition.
Use of this process indicated retained activity, however, the process failed to yield compound 540 of sufficient purity.

Method used

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  • Purification of cinnamoyl-C-glycoside chromone
  • Purification of cinnamoyl-C-glycoside chromone
  • Purification of cinnamoyl-C-glycoside chromone

Examples

Experimental program
Comparison scheme
Effect test

first embodiment

Several commercial processes employed in the processing of slurries from aloe leaf extracts utilize activated carbon (also referred to as activated charcoal) to improve the color of the extracts. Treatment with activated carbon is particularly common with so-called "whole-leaf processing", wherein the entire leaf is ground and processed. A series of experiments on aloe extracts, which had been isolated from the Aloe barbadensis plant, followed by treatment with activated carbon led to the discovery that certain activity associated with the 540 compound was not present in the extracts after treatment with the activated carbon. This led to the discovery that the 540 compound is absorbed by activated carbon. (See, U.S. application Ser. No. 08 / 391,139, entitled Cinnamoyl-C-Glycoside Chromone Isolated from Aloe barbadensis, filed Feb. 21, 1995). A key feature in the method of the present invention is the extraction of compound 540 from decolorizing agents, such as activated charcoal, usi...

second embodiment

In the present invention crude aloe extract, isolated from the leaf rind of the aloe plant is purified by column chromatography without first being treated with a decolorizing agent. This method cuts out a step in the processing of the extracts and provides a fast and simple method of purification, which is ideally suited for large scale production.

In the first embodiment of the present invention, described in Example 1, a decolorizing agent, isolated from the processing of a slurry prepared from aloe leaf extracts, is treated with an organic solvent to extract the absorbed 540 compound. In a preferred embodiment the slurry from which the decolorizing agent is isolated is prepared from the whole leaf or the leaf rind of the Aloe barbadensis plant. Because the majority of the 540 compound is present in the leaf rind or latex, in the most preferred embodiment the slurry is prepared from the leaf rind or latex. In the preferred embodiment the decolorizing agent is activated charcoal, h...

example 1

Extraction of the 540 Compound from Activated Carbon using Methanol and Acetone (room temperature).

Five hundred grams of freeze-dried, spent activated carbon from whole leaf production was placed in a 2 liter beaker. One and one half liters of methanol was added and the slurry was stored at room temperature for 2 hours. After 2 hours, the slurry was filtered through 0.5 micron cellulose filter paper. The filtrate was stripped of methanol under vacuum and the residue subjected to HPLC analysis. The procedure was then repeated using acetone as the solvent.

Analytical HPLC Analysis

Column: ODS-1, 4 mm.times.250 mm, 5 .mu. particle size

Temperature: Ambient

Mobile Phase: 55% methanol / 45% water

Flow Rate: 0.70 ml / min

Detector Wavelength: 205 nm

Injection Volume: 10-20 .mu.l

Sensitivity: 0.20 AUFS

Retention Time: Approximately 16-17 min.

HPLC analysis shows that methanol is more effective at extracting the 540 compound from the decolorizing agent than acetone. An illustrative HFLC spectrum of the 5...

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Abstract

The present invention provides a process for purifying the cinnamoyl-C-glycoside, <DEL-S DATE="20020625" ID="DEL-S-00001"/>8-C-beta-D-[2-O-(E)-cinnamoyl]glycopyranosyl-2- [(R)-2-hydroxy]propyl-7-methoxy-5-methyl-chromone.<DEL-E ID="DEL-S-00001"/> <INS-S DATE="20020625" ID="INS-S-00001"/>8-C-beta-D-[2'-O- (E)-cinnamoyl]glycopyranosyl-2-[(S) -2-hydroxy]propyl-7-methoxy-5-methylchromone, <INS-E ID="INS-S-00001"/>referred to herein as the "540 compound." In one embodiment of the present invention the 540 compound is purified by extraction from a decolorizing agent with an organic solvent. The extracted product can be purified by high pressure liquid chromatography. In a second embodiment crude 540 compound, which has not been treated with a decolorizing agent, is purified by passage over neutral alumina or sephadex.

Description

FIELD OF INVENTIONThe present invention relates generally to the purification of an anti-inflammatory and epithelial growth factor-inhibiting compound isolated from the Aloe barbadensis plant. Specifically, this invention describes the purification of the cinnamoyl-C-glycoside, .[.8-C-.beta.-D-[2-O-(E)-cinnamoyl]glycopyranosyl-2-[(R)-2-hydroxy]propyl- 7-methoxy-5-methyl-chromone..]. .Iadd. 8-C-.beta.-D-[2'-O-(E)-cinnamoyl]glycopyranosyl-2-[(S)-2-hydroxy]propyl-7- methoxy-5-methylchromone, .Iaddend.which has a molecular weight of 541 Daltons, and is referred to herein as the "540 compound."BACKGROUND OF THE INVENTIONThe aloe plant is an intricate plant which contains many biologically active substances. (Cohen et al. in Wound Healing / Biochemical and Clinical Aspects, 1st ed. W B Saunders, Philadelphia (1992)). Studies have shown that these biologically active substances are located in three separate sections of the aloe leaf--a clear gel fillet located in the center of the leaf, in t...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C07H1/00C07H1/08
CPCC07H1/08
Inventor WALLER, TODDJIA, QIPADMAPRIYA, ABEYSINGHE
Owner UNIGEN
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