CN1271053C - Method for extracting and preparing N-methyl-1-deoxy noijirimycin - Google Patents
Method for extracting and preparing N-methyl-1-deoxy noijirimycin Download PDFInfo
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- CN1271053C CN1271053C CN 200410048393 CN200410048393A CN1271053C CN 1271053 C CN1271053 C CN 1271053C CN 200410048393 CN200410048393 CN 200410048393 CN 200410048393 A CN200410048393 A CN 200410048393A CN 1271053 C CN1271053 C CN 1271053C
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- methyl isophthalic
- isophthalic acid
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- solution
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Abstract
The present invention discloses a method for extracting and preparing N-methyl-1-deoxynojirimycin. The method comprises the following steps: step a, morus plants are cut up, water is added for soaking the morus plants, and the filtration of the morus plants is carried out. A filter solution is concentrated, and a concentrated solution is obtained; step b, the concentrated solution is precipitated by ethanol, a clear solution is separated by cation exchange resin, and after washed by water, the clear solution is added with 0.2 to 0.5M of ammonia for being eluted; step c, ammonia eluent is collected and is concentrated; step d, formaldehyde and acetic acids (or formic acids) are added to the clear solution of step c, and after warmed for 1 to 10 hours at 40 to 90 DEG C, the concentrated solution, the formaldehyde and the acetic acids (or formic acids) are separated by anion exchange resin. The N-methyl-1-deoxynojirimycin (N-Me-DNJ) is obtained. The method has simple technology and high yield, and simultaneously the method can realize industrialized production.
Description
Technical field
The present invention relates to from plant, extract the method for compound.Specifically, be the method for from the Morus plant, extracting N-methyl isophthalic acid-S-GI.
Background technology
N-methyl isophthalic acid-S-GI (hereinafter to be referred as N-Me-DNJ) is present in the Morus plant, all contains this compound in White Mulberry Root-bark, mulberry leaf, ramulus mori, the mulberry fruit.There is report to confirm that this compound has the effect of obvious suppression blood sugar increasing, also has the effect of AIDS virus resisting (HIV) simultaneously concurrently.Therefore, can use it for the medicine of preparation treatment and prevent diabetes and acquired immune deficiency syndrome (AIDS).
But, since still unmanned at present from the Morus plant with its a large amount of extraction separation, so its application in pharmacy field is restricted.For example Naoki Asano provides a kind of method, and this method is to extract with the methanol aqueous solution that adopts 50% earlier, and its extracting solution separates to obtain this compound with different anion and cation exchange resin repeatedly.This method obtains obtaining in 6.4mgN-Me-DNJ, the per kilogram mulberry fruit N-Me-DNJ of 5mg from the per kilogram White Mulberry Root-bark, from mulberry leaf, fail to obtain N-Me-DNJ (J.of Agricultural and FoodChemistry, Vol.49, No.9, (2001), pp.4208-4213).This method complex process, yield is low, and can't realize suitability for industrialized production.This shows that a large amount of separation preparation N-Me-DNJ are difficult problems from the Morus plant.
Summary of the invention
The purpose of this invention is to provide and a kind ofly can extract the method for preparing N-methyl isophthalic acid-S-GI in a large number, and its technology is simple, the yield height can be realized suitability for industrialized production.
The chemical structure of N-methyl isophthalic acid-S-GI (N-Me-DNJ) is as follows:
The object of the present invention is achieved like this:
The inventive method may further comprise the steps:
A) with the chopping of Morus plant, soak, filter, filtrate is concentrated, get concentrated extracting solution; When its water is carried, can adopt normal temperature dipping to extract, also can adopt heating to extract.But preferably soaked 1-2 days, and, heated after 1-2 hour, refilter, concentrated filtrate at 80-100 ℃; Filtrate preferably is concentrated into the 1/10-1/15 of stoste volume, so more helps the abundant extraction separation of effective constituent.
B) concentrated solution is precipitated with alcohol, supernatant liquor separates through Zeo-karb, after the washing, adds the ammoniacal liquor wash-out of 0.2-0.5M; Used alcohol can be methyl alcohol, ethanol, propyl alcohol, Virahol, propyl carbinol or its arbitrary proportion mixture.The consumption of alcohol is preferably O.5-3 times (by volume) of concentrated solution.
C) collection, concentrated liquor elutriant;
D) in the concentrated solution of c step, add formaldehyde and formic acid or formaldehyde and acetate,, obtain N-methyl isophthalic acid-S-GI (N-Me-DNJ) through the anionite-exchange resin separation 40-90 ℃ of insulation 1-10 hour.
Said Morus plant can be a White Mulberry Root-bark in this method, also can be mulberry leaf, mulberry fruit or ramulus mori.
Embodiment
Further specify characteristics of the present invention below by specific embodiment.
Embodiment 1
Produce N-methyl isophthalic acid-S-GI with mulberry leaf.
Concrete preparation process:
One kilogram on mulberry leaf, add 15 times of water, soak, secondary is extracted in heating, each 2 hours, filter, be concentrated into about 1 liter, add 1 liter of ethanol, supernatant liquor separates with the strongly acidic cation-exchange post, earlier with 8 premium on currency wash-outs, uses 0.3M ammoniacal liquor wash-out again, collect the ammoniacal liquor elutriant, concentrate the back and add formaldehyde and each 10ml of acetate, after 3 hours, separate with strong acid type anionite-exchange resin 80 ℃ of insulations, water elution, with every 300ml is that portion is collected, and detects PrOH-AcOH-H with thin-layer chromatography (TLC method)
2O (4: 1: 1) is a developping agent.Merging the Rf value is 0.23, is the red-purple part after the triketohydrindene hydrate colour developing, obtains N-methyl isophthalic acid-S-GI (1510mg) after concentrating.
Embodiment 2
Extract N-methyl isophthalic acid-S-GI with White Mulberry Root-bark.
Concrete preparation process:
One kilogram of White Mulberry Root-bark, the water that adds 10 times of amounts, heat 95 ℃ and extract secondary, each 2 hours, filter, be concentrated into 1 liter after, add 1 liter of ethanol, supernatant liquor separates with the strongly acidic cation-exchange post, earlier with 5 premium on currency wash-outs, uses 0.5M ammoniacal liquor wash-out again, collect the ammoniacal liquor elutriant, concentrate the back and add formaldehyde and each 15ml of formic acid, 60 ℃ of heating separated with strong acid type anionite-exchange resin after 5 hours, water elution, with every 300ml is that portion is collected, and detects PrOH-AcOH-H with thin-layer chromatography (TLC method)
2O (4: 1: 1) is a developping agent.Merging the Rf value is 0.23, is the red-purple part after the triketohydrindene hydrate colour developing, obtains N-methyl isophthalic acid-S-GI (1780mg) after concentrating.
Embodiment 3
Extract N-methyl isophthalic acid-S-GI with the normal temperature dipping method.
Concrete preparation process:
One kilogram on mulberry leaf, 15 times of water extract at room temperature secondaries, each 24 hours, filter, be concentrated into about 1 liter, add 1 liter of methyl alcohol, supernatant liquor separates with the strongly acidic cation-exchange post, earlier with 5 premium on currency wash-outs, uses 0.2M ammoniacal liquor wash-out again, collect the ammoniacal liquor elutriant, concentrate the back and add formaldehyde and each 10ml of acetate, 70 ℃ were heated 5 hours, concentrate the back and separate with strong acid type anionite-exchange resin, water elution is that portion is collected with every 300ml, detect PrOH-AcOH-H with thin-layer chromatography (TLC method)
2O (4: 1: 1) is a developping agent.Merging the Rf value is 0.23, is the red-purple part after the triketohydrindene hydrate colour developing, obtains N-methyl isophthalic acid-S-GI (950mg) after concentrating.
Embodiment 4
Extract N-methyl isophthalic acid-S-GI with mulberry fruit.
Concrete preparation process:
One kilogram in mulberry fruit, 12 times of water heating are extracted secondary, each 2 hours for 95 ℃, filter, be concentrated into 1 liter after, add 1 liter of ethanol, supernatant liquor separates with the strongly acidic cation-exchange post, earlier with 8 premium on currency wash-outs, uses 0.5M ammoniacal liquor wash-out again, collect the ammoniacal liquor elutriant, concentrate the back and add formaldehyde 10ml, acetate 15ml, 80 ℃ of heating separated water elution after 3 hours with strong acid type anionite-exchange resin, with every 300ml is that portion is collected, and detects PrOH-AcOH-H with thin-layer chromatography (TLC method)
2O (4: 1: 1) is a developping agent.Merging the Rf value is 0.23, is the red-purple part after the triketohydrindene hydrate colour developing, obtains N-methyl isophthalic acid-S-GI (1660mg) after concentrating.
Embodiment 5
Extract N-methyl isophthalic acid-S-GI with ramulus mori.
Concrete preparation process:
One kilogram of ramulus mori, 10 times of water heating are extracted secondary, each 2 hours for 95 ℃, filter, be concentrated into 1 liter after, add 1 liter of ethanol, supernatant liquor separates with the strongly acidic cation-exchange post, earlier with 5 premium on currency wash-outs, uses 0.4M ammoniacal liquor wash-out again, collect the ammoniacal liquor elutriant, concentrate the back and add formaldehyde and each 5ml of formic acid, 70 ℃ of heating are after 4 hours, separate with strong acid type anionite-exchange resin, water elution is that portion is collected with every 300ml, detect PrOH-AcOH-H with thin-layer chromatography (TLC method)
2O (4: 1: 1) is a developping agent.Merging the Rf value is 0.23, is the red-purple part after the triketohydrindene hydrate colour developing, obtains N-methyl isophthalic acid-S-GI (370mg) after concentrating.
Embodiment 6
N-methyl isophthalic acid-S-GI that embodiment 1-5 is obtained carries out structural analysis:
FAB-MS:m/z 178 (M+1)
+, prove that its molecular weight is 177;
1HNMR (D20): 1.95 (1H, H-5), 2.20 (1H, H-lax), 2.33 (3H, N-CH3), 2.99 (1H, H-leq), 3.29 (1H, H-3), 3.39 (1H, H-4), 3.55 (1H, H-2), 3.85 (1H, H-6a), 3.92 (1H, H-6b);
13C-NMR (D20): 79.8 (C-3), 71.0 (C-2), 70.7 (C-4), 70.0 (C-5), 60.7 (C-6), 58.1 (C-7), 43.8 (N-CH3).
Silica gel thin-layer chromatography, PrOH-AcOH-H
2O (4: 1: 1) is a developping agent, Rf value 0.23, and the triketohydrindene hydrate colour developing is red-purple.These data and document (Carbohydrate Research, 253,1994, pp.235-245) Bao Dao N-methyl isophthalic acid-S-GI data consistent proves that the material that obtains is N-methyl isophthalic acid-S-GI in embodiment 1-5.
Use method of the present invention, can from per kilogram White Mulberry Root-bark, mulberry fruit and mulberry leaf, obtain N-methyl isophthalic acid-S-GI of 1780mg, 1660mg and 950mg respectively, and literature method (J.of Agriculturaland Food Chemistry, Vol.49, No.9, (2001), pp.4208-4213), from per kilogram White Mulberry Root-bark, mulberry fruit, can only obtain N-methyl isophthalic acid-S-GI of 6.4mg, 5mg, and from mulberry leaf, fail to obtain N-methyl isophthalic acid-S-GI.
In sum, the inventor has finished the method research that a large amount of extractions prepare N-Me-DNJ from the Morus plant on a large amount of scientific experimentation bases.This method technology is simple, and the yield height makes it can realize suitability for industrialized production simultaneously.
Claims (7)
1, a kind of method for preparing N-methyl isophthalic acid-S-GI of extracting is characterized in that it may further comprise the steps:
A, with Morus plant chopping, soak, filter, filtrate is concentrated, concentrated extracting solution;
B, with concentrated solution with alcohol precipitation, supernatant liquor separates through Zeo-karb, after the washing, adds the ammoniacal liquor wash-out of 0.2-0.5M;
C, collection, concentrated liquor elutriant;
D, in the concentrated solution of c step, add formaldehyde and acetate or formaldehyde and formic acid, 40-90 ℃ of insulation after 1-10 hour, separate to obtain N-methyl isophthalic acid-S-GI through anionite-exchange resin.
2, according to the described method for preparing N-methyl isophthalic acid-S-GI of claim 1, it is characterized in that soaking 1-2 days in the said a step, at 80-100 ℃, heat after 1-2 hour, refilter, concentrate.
3, according to the described method for preparing N-methyl isophthalic acid-S-GI of claim 1,, the consumption that it is characterized in that said alcohol is 0.5-3 a times of concentrated solution.
4, the method for preparing N-methyl isophthalic acid-S-GI according to claim 1 is characterized in that said Morus plant is a White Mulberry Root-bark.
5, the method for preparing N-methyl isophthalic acid-S-GI according to claim 1 is characterized in that said Morus plant is mulberry leaf.
6, the method for preparing N-methyl isophthalic acid-S-GI according to claim 1 is characterized in that said Morus plant is a mulberry fruit.
7, the described method for preparing N-methyl isophthalic acid-S-GI of claim 1 is characterized in that said Morus plant is a ramulus mori.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN 200410048393 CN1271053C (en) | 2004-06-30 | 2004-06-30 | Method for extracting and preparing N-methyl-1-deoxy noijirimycin |
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| CN 200410048393 CN1271053C (en) | 2004-06-30 | 2004-06-30 | Method for extracting and preparing N-methyl-1-deoxy noijirimycin |
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| CN1271053C true CN1271053C (en) | 2006-08-23 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102018766B (en) * | 2009-09-16 | 2013-03-06 | 博仲盛景医药技术（北京）有限公司 | Plant extractive, extraction method and application thereof as well as composite comprising same |
| CN102204671A (en) * | 2010-03-30 | 2011-10-05 | 雀巢公司 | Composition containing morus berry |
| CN103417634B (en) * | 2013-07-16 | 2015-08-26 | 暨南大学 | A kind of Ramulus Mori active site and its preparation method and application |
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