The present invention relates to a process for purifying dimeric to pentameric proanthocyanidin oligomers which comprises extracting the proanthocyanidin oligomers from raw materials containing the proanthocyanidin oligomers or crude purification products therefrom by solid-liquid extraction using m
The present invention relates to a process for purifying dimeric to pentameric proanthocyanidin oligomers which comprises extracting the proanthocyanidin oligomers from raw materials containing the proanthocyanidin oligomers or crude purification products therefrom by solid-liquid extraction using methyl acetate as a liquid phase; a process for purifying dimeric to pentameric proanthocyanidin oligomers which comprises pretreating with an enzyme for hydrolysis raw materials containing the proanthocyanidin oligomers, crude purification products therefrom, or a solution containing one of these; and a process for purifying dimeric to pentameric proanthocyanidin oligomers with a uniform polymerization degree which comprises separating and purifying the proanthocyanidin oligomers by polymerization degree from raw materials containing the proanthocyanidin oligomers or crude purification products there from by normal phase silica gel liquid chromatography using as a mobile phase a single solvent or a mixed solvent of two or more solvents selected from the group consisting of an ester solvent, a ketone solvent, a hydrocarbon solvent, an ether solvent and an alcohol solvent.
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1. A process for purification of dimeric to pentameric proanthocyanidin oligomers, which comprises extracting the proanthocyanidin oligomers from raw materials, which contain the proanthocyanidin oligomers or crude purification products therefrom, by a solid-liquid extraction method using methyl ace
1. A process for purification of dimeric to pentameric proanthocyanidin oligomers, which comprises extracting the proanthocyanidin oligomers from raw materials, which contain the proanthocyanidin oligomers or crude purification products therefrom, by a solid-liquid extraction method using methyl acetate as a liquid phase. 2. The process for purification of claim 1, wherein the raw materials are derived from a plant. 3. The process for purification of claim 1, wherein the liquid phase comprises an organic solvent miscible with methyl acetate. 4. The process for purification of claim 3, wherein the organic solvent miscible with methyl acetate is selected from the group consisting of an alcohol solvent, an ester solvent, a ketone solvent, a nitrile solvent, an ether solvent, a hydrocarbon solvent and a carboxylic acid solvent. 5. The process for purification of claim 3, wherein the organic solvent miscible with methyl acetate is selected from the group consisting of methanol, ethanol, propanol, butanol, methyl formate, ethyl formate, ethyl acetate, acetone, acetonitrile, tetrahydrofuran, hexane and acetic acid. 6. A process for purification of dimeric to pentameric proanthocyanidin oligomers which comprises pretreating with an enzyme for hydrolysis raw materials which contain the proanthocyanidin oligomers, crude purification products therefrom, or a solution containing one of these. 7. The process for purification of claim 6, wherein the raw materials are derived from a plant. 8. The process for purification of claim 6, wherein the solution is an aqueous solution containing a 10% or less organic solvent. 9. The process for purification of claim 8, wherein the organic solvent is an alcohol, ester, or ketone organic solvent. 10. The process for purification of claim 6, wherein the enzyme for hydrolysis is glycosidase or esterase. 11. The process for purification of claim 10, wherein the glycosidase is a single substance or a mixture of two or more substances selected from the group consisting of amylase, cellulase, glucanase, xylanase, glucosidase, dextranase, chitinase, galacturonase, lysozyme, galactosidase, mannosidase, fructofuranosidase, trehalase, glucosaminidase, pullulanase, ceramidase, fucosidase and agarase. 12. The process for purification of claim 10, wherein the esterase is a single substance or a mixture of two or more substances selected from the group consisting of carboxyesterase, arylesterase, lipase, acetylesterase, cholinesterase, pectinesterase, cholesterol esterase, chlorophyllase, lactonase, tannase and hydrolase. 13. A process for purification of dimeric to pentameric proanthocyanidin oligomers with a uniform polymerization degree which comprises:selecting raw materials containing dimeric to pentameric proanthocyanidin oligomers or crude purification products therefrom;separating and purifying said raw materials by normal phase silica gel liquid chromatography using as a mobile phase at least one solvent selected from the group consisting of an ester solvent, a ketone solvent, a hydrocarbon solvent, an ether solvent and an alcohol solvent. 14. The process for purification of claim 13, wherein the raw materials are derived from a plant. 15. The process for purification of claim 13, wherein mobile phase is a mixture of at least two of said solvents. 16. The process for purification of claim 13, wherein the ester solvent is selected from the group consisting of methyl formate, ethyl formate, propyl formate, isopropyl formate, butyl formate, isobutyl formate, methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, isobutyl acetate, methyl propionate, ethyl propionate, propyl propionate, isopropyl propionate, butyl propionate, isobutyl propionate, methyl butyrate, ethyl butyrate, propyl butyrate, isopropyl butyrate, butyl butyrate and isobutyl butyrate. 17. The process for purification of claim 13, wherein the ketone solvent is selected from the group consisting of acetone, methyl ethyl ketone, methyl propyl ketone, methyl isopropyl ketone, methyl butyl ketone, methyl isobutyl ketone, methyl tert-butyl ketone, diethyl ketone, diisopropyl ketone, methyl vinyl ketone, cyclobutanone, cyclopentanone and cyclohexanone. 18. The process for purification of claim 13, wherein the hydrocarbon solvent is selected from the group consisting of pentane, hexane, heptane, octane, nonane, decane, nonadecane, cyclohexane, xylene and toluene. 19 .The process for purification of claim 13, wherein the ether solvent is tetrahydrofuran or 1, 2-dimethoxyethane. 20. The process for purification of claim 13, wherein the alcohol solvent is selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, sec-butanol and tert-butanol. 21. A process for purification of dimeric to pentameric proanthocyanidin oligomers comprising at least two processes for purification selected from claims 1 , 6 and 13 . 22. A purified dimeric to pentameric proanthocyanidin oligomer with a purity of 90 (w/w)% or more obtained by the process for purification of claim 1. 23. A purified dimeric to pentameric proanthocyanidin oligomer with a purity of 90 (w/w)% or more obtained by the process for purification of claim 6. 24. A purified dimeric to pentameric proanthocyanidin oligomer with a purity of 90 (w/w)% or more obtained by the process for purification of claim 21. 25. A purified dimeric proanthocyanidin with a purity of 90 (w/w)% or more obtained by the process for purification of claim 13. 26. A purified trimeric proanthocyanidin with a purity of 90 (w/w)% or more obtained by the process for purification of claim 13. 27. A process for purification of dimeric to pentameric proanthocyanidin oligomers with a uniform polymerization degree comprising a combination of the process for purification of claim 13, andat least one process selected from the group consisting of (i) a process for purification of dimeric to pentameric proanthocyanidin oligomers which comprises extracting the proanthocyanidin oligomers from raw materials, which contain the proanthocyanidin oligomers or crude purification products therefrom, by a solid-liquid extraction method using methyl acetate as a liquid phase, and (ii) a process for purification of dimeric to pentameric proanthocyanidin oligomers which comprises pretreating with an enzyme for hydrolysis raw materials which contain the proanthocyanidin oligomers, crude purification products therefrom, or a solution containing one of these. 28. A purified dimeric proanthocyanidin with a purity of 90 (w/w)% or more obtainable by the process for purification of claim 27. 29. A purified trimeric proanthocyanidin with a purity of 90 (w/w)% or more obtainable by the process for purification of claim 27. 30. A purified dimeric to pentameric proanthocyanidin oligomer with a purity of 90 (w/w)% or more. 31. A purified dimeric proanthocyanidin oligomer with a purity of 90 (w/w)% or more. 32. A purified trimeric proanthocyanidin oligomer with a purity of 90 (w/w)% or more.
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