CN101029071B - Method for preparing high-purity Momordia grosvenori aglycone from Momordia grosvenori - Google Patents

Method for preparing high-purity Momordia grosvenori aglycone from Momordia grosvenori Download PDF

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CN101029071B
CN101029071B CN200710039130A CN200710039130A CN101029071B CN 101029071 B CN101029071 B CN 101029071B CN 200710039130 A CN200710039130 A CN 200710039130A CN 200710039130 A CN200710039130 A CN 200710039130A CN 101029071 B CN101029071 B CN 101029071B
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purity
momordica
water
medicinal extract
momordia grosvenori
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CN101029071A (en
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李晓波
王梦月
屠鹏飞
周兢
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Shanghai Jiaotong University
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Abstract

A process for preparing high-purity momordicoside from fructus momordicae includes such steps as pulverizing, reflux extracting in alcohol, filtering to obtain extract A, suspending it in water, extracting in ethyl acetate 1-3 times, recovering ethyl acetate mother liquid, extracting in n-butanol 1-3 times, recovering n-butanol to obtain extract B, passing it through polyamide column, water washing, concentrating to obtain coarse saponin, chromatography by silica gel column, eluting with chloroform-methanol-water, collecting coarse momordicoside V, chromatography, water washing, eluting with alcohol, and collecting product.

Description

The method that from Grosvenor Momordica, prepares high-purity Momordia grosvenori aglycone V
Technical field
What the present invention relates to is a kind of extracting method of biological technical field, is a kind of method for preparing high-purity Momordia grosvenori aglycone V from Grosvenor Momordica specifically.
Technical background
Grosvenor Momordica, the dry mature fruit that belongs to herbaceous perennial vine plant Grosvenor Momordica Momordicagrosvenori Swingle for the cucurbitaceous plant Grosvenor Momordica, it is a conventional Chinese medicine, have clearing away summer heat, the moistening lung effect of quenching the thirst, can be used for treating multiple diseases such as hypertension, pulmonary tuberculosis, asthma, gastritis, Whooping cough, acute/chronic bronchitis and acute and chronic tonsillitis clinically.Grosvenor Momordica also is a beverage dry fruit commonly used simultaneously, and extract is a sweeting agent commonly used, and ground such as South East Asia, Canada, the U.S. are found a good sale in a large amount of outlets.
Main component in Grosvenor Momordica and the Fructus Monordicae extract is a cucurbitane type triterpenoid saponin, comprises Momordia grosvenori aglycone IV (mogroside IV), momordica grosvenori glycoside V (mogroside V), Simon glycosides I (siamenoside I), 11-oxygen-momordica grosvenori glycoside V (11-oxo-mogroside V), Momordia grosvenori aglycone II E(mogroside II E), Momordia grosvenori aglycone III E(mogroside III F) wait multiple saponin(e, wherein momordica grosvenori glycoside V is main saponin component.Momordica grosvenori glycoside V also is the main active ingredient composition of Grosvenor Momordica, has multiple pharmacological effect such as antitumor, hypoglycemic.Momordica grosvenori glycoside V also is the main sweet ingredient of Grosvenor Momordica, and its sugariness height is more than 400 times of sucrose.Because the development of pharmaceutical industry and foodstuffs industry is very big to the demand of highly purified Grosvenor Momordica V both at home and abroad at present, produces and sells but had not yet to see highly purified momordica grosvenori glycoside V.Though have multinomial patent application to relate to the extraction of mogroside, method is simple, products therefrom is the total glycosides of Grosvenor Momordica, and the purity of momordica grosvenori glycoside V is all lower in the extract, is no more than 80%, has limited its range of application.Though the purity of momordica grosvenori glycoside V is not high in the product that obtains, be not suitable for preparation highly purified momordica grosvenori glycoside V more than 95%.
Find by prior art documents, publication number is the Chinese invention patent of CN1706861A, in 2005.12.14 disclosed " preparation method of high-purity Momordia grosvenori aglycone V and purposes ", pure medicinal extract separates back employing purification on normal-phase silica gel column chromatography with D101 type macroporous resin in its preparation process, further adopt the C18 column chromatography then, elutriant is checked through HPLC.This method adopts the macroporous resin removal of impurities, operates more loaded down with trivial details; Adopt the acetone-water wash-out during reversed phase chromatography, certain toxicity is arranged; Purity and yield all have certain limitation.
Summary of the invention
The objective of the invention is to overcome deficiency of the prior art, a kind of method for preparing high-purity Momordia grosvenori aglycone V from Grosvenor Momordica is provided, simplified technology, have advantages such as purity height, yield height, production cost be low.
The present invention is achieved through the following technical solutions, and specifically comprises the steps:
(1) earlier mangosteen powder is broken into meal, adds the alcohol reflux 2h-6h of 5-10 71%-95% doubly, filter, reclaim ethanol and get pure medicinal extract.Aforesaid operations can repeat 1 time-2 times.
(2) pure medicinal extract is suspended in water (water consumption be pure medicinal extract weight 5-10 doubly), with water saturated ethyl acetate extraction 1 time-3 times, the 0.5-1.0 that each ethyl acetate volume is an aqueous solution volume doubly, recovery ethyl acetate mother liquor, ethyl acetate medicinal extract discards.
(3) continue with 1 time-3 times last step mother liquors of water saturated n-butanol extraction, the 0.5-1.0 that each propyl carbinol volume is an aqueous solution volume doubly reclaims propyl carbinol and gets propyl carbinol medicinal extract.
(4) with propyl carbinol medicinal extract by polyamide column (consumption of polymeric amide be propyl carbinol medicinal extract weight 20-60 doubly), be washed to no momordica grosvenori glycoside V and wash out (detection method: the detection of silica gel G thin layer, developping agent CHCl 3-MeOH-H 2O 65: 30: 5, the Rf of momordica grosvenori glycoside V are 0.4).Water lotion concentrate thick saponin(e.
(5) thick saponin(e carries out silica gel column chromatography (the silica gel consumption is 30-100 a times of thick saponin(e weight), chloroform-methanol-water elution (65: 30: 1~65: 30: 5), collection contains momordica grosvenori glycoside V, and (detection method: the high-efficient liquid phase chromatogram HPLC method is a weighting agent with the octadecyl silane in the component more than 40%; With acetonitrile-water (24: 76) is moving phase; The detection wavelength is 210nm, flow velocity 1.0ml/min), merge, reclaim solvent, get Momordia grosvenori aglycone v crude product.
(6) get Momordia grosvenori aglycone v crude product and carry out C18 reversed-phase silica gel column chromatography (the reverse phase silica gel consumption is 50-200 a times of the thick glycosides v of Grosvenor Momordica weight), washing, discard water lotion, 20%~50% ethanol elution is collected purity in the flow point more than 95% (the same step of detection method (5)).Merge the identical component of retention time, reclaim solvent, promptly get purity greater than the momordica grosvenori glycoside V more than 95%.Through IR, MS, 1H-NMR, 13The C-NMR data are consistent with momordica grosvenori glycoside V, and its structural formula is as follows:
Figure G2007100391306D00031
Beneficial effect of the present invention: separate the Grosvenor Momordica soap V for preparing by aforesaid method, the purity height, all more than 95%, and production cost is low.Adopt ethyl acetate to remove most of fat-soluble component in the extract (as lipid acid, grease, flavones, plant sterol), simplified the purifying process of Grosvenor Momordica soap V.Adopt propyl carbinol from the total glycosides of Grosvenor Momordica extracting Grosvenor Momordica, avoided the interference of a large amount of sugars in the extract, also avoided shortcoming simultaneously with the macroporous resin column chromatography troublesome poeration; For impurity such as the remaining water-soluble flavone of extract, water colo(u)r and tannins, remove by the polyamide column chromatography method, further simplified technology.Reversed phase column chromatography adopts dilute alcohol solution to take off agent as stream, has simplified technology, and it is low to have a purity height, yield height, production cost.Medium by different separation principles such as integrated use polymeric amide, silica gel, reverse phase silica gels carries out purifying,
Embodiment
Below embodiments of the invention are elaborated: present embodiment has provided detailed embodiment and process being to implement under the prerequisite with the technical solution of the present invention, but protection scope of the present invention is not limited to following embodiment.
Embodiment 1
Present embodiment 1 is implemented under following implementation condition and technical requirements condition:
1. Grosvenor Momordica dry fruit 1Kg adds the industrial alcohol refluxing extraction 2h of 5L 71%, filter, filtrate recycling ethanol (can be used for medicinal material extract once more), pure medicinal extract 94g.
2. get pure medicinal extract, add the aqueous suspension of 470mL, use the water saturated ethyl acetate extraction of 235mL volume of water then, the separating ethyl acetate layer, reclaim under reduced pressure ethyl acetate (can be used for extraction once more) gets ethyl acetate medicinal extract 13g.
3. to continue to use water saturated n-butanol extraction, consumption be 235mL to the aqueous solution behind the ethyl acetate extraction.Isolate propyl carbinol, reclaim under reduced pressure propyl carbinol (can be used for extraction once more) gets propyl carbinol medicinal extract 15g.
With propyl carbinol medicinal extract with water dissolution after, by 300g 100-200 purpose polyamide column (column diameter 4.5cm, dry column-packing, sample on the wet method) is housed, is washed to no momordica grosvenori glycoside V and flows out that (detection method: the silica gel G thin layer detects, developping agent CHCl 3-MeOH-H 2O 65: 30: 5, the Rf of momordica grosvenori glycoside V are 0.4), collect effluent liquid and water lotion.Solvent is to the greatest extent received in decompression, gets thick saponin(e 12.5g.
5. thick saponin(e is carried out silica gel column chromatography (silica gel consumption 375g, 300-400 order; Column diameter 4.5cm, dry column-packing, sample on the dry method), chloroform-methanol-water (65: 30: 1) wash-out, flow velocity 5ml/min collects 50ml for every part, collection contains momordica grosvenori glycoside V, and (detection method: the high-efficient liquid phase chromatogram HPLC method is a weighting agent with the octadecyl silane in the component more than 40%; With acetonitrile-water is moving phase at 24: 76; The detection wavelength is 210nm, flow velocity 1.0ml/min), merge, decompression and solvent recovery gets Momordia grosvenori aglycone v crude product 2.2g.
6. get Momordia grosvenori aglycone v crude product and carry out reversed phase column chromatography, reverse phase silica gel consumption 110g (silica gel particle diameter: 400-600 order; Column diameter 4.5cm, wet method dress post, sample on the wet method), washing discards water lotion; 20% alcohol is washed, flow velocity 2ml/min, collect 10ml for every part, each flow point is carried out high performance liquid chromatography (HPLC) detect (detection method is with 5), merge the identical and purity of retention time greater than 95% component, concentrating under reduced pressure promptly gets purity greater than the momordica grosvenori glycoside V 464mg more than 95%, is 96.7% through checking its purity.
Embodiment 2
Present embodiment 2 is implemented under following implementation condition and technical requirements condition:
1. Grosvenor Momordica dry fruit 1Kg adds the industrial alcohol refluxing extraction 6h of 10L 95%, filter, filtrate recycling ethanol (can be used for medicinal material extract once more), medicinal extract.Repeat aforesaid operations 2 times, get pure medicinal extract 168g.
2. get pure medicinal extract, add the aqueous suspension of 1680mL, use the water saturated ethyl acetate extraction of 1680mL then, the separating ethyl acetate layer, reclaim under reduced pressure ethyl acetate (can be used for extraction once more) gets medicinal extract.Repeat aforesaid operations 2 times, merge medicinal extract, get ethyl acetate medicinal extract 21g.
3. to continue to use water saturated n-butanol extraction, consumption be 1680mL to the aqueous solution behind the ethyl acetate extraction.Isolate propyl carbinol, reclaim under reduced pressure propyl carbinol (can be used for extraction once more) gets medicinal extract.Repeat aforesaid operations 2 times, merge medicinal extract, get propyl carbinol medicinal extract 29g.
With propyl carbinol medicinal extract with water dissolution after, the 60-100 order polyamide column by 1740g is housed (column diameter 8.0cm, wet method dress post, sample on the wet method) is washed to no momordica grosvenori glycoside V and flows out (detection method: the detection of silica gel G thin layer, developping agent CHCl 3-MeOH-H 2O 65: 30: 5, the Rf of momordica grosvenori glycoside V are 0.4), collect effluent liquid and water lotion.Solvent is to the greatest extent received in decompression, gets thick saponin(e 21g.
5. thick saponin(e is carried out silica gel column chromatography, the silica gel consumption is 2100g (column diameter 8.0cm, a 100-200 order; Wet method dress post, sample on the wet method), chloroform-methanol-water (65: 30: 5) wash-out, flow velocity 10ml/min, every 100ml collects 1 part, and collection contains momordica grosvenori glycoside V, and (detection method: high performance liquid chromatography (HPLC) method is a weighting agent with the octadecyl silane in the component more than 40%; With acetonitrile-water is moving phase at 24: 76; The detection wavelength is 210nm, flow velocity 1.0ml/min), merge, decompression and solvent recovery gets Momordia grosvenori aglycone v crude product 3.4g.
6. get Momordia grosvenori aglycone v crude product and carry out reversed phase column chromatography, the reverse phase silica gel consumption is a 680g (silica gel particle diameter: 300-400 order; Column diameter 6.5cm, wet method dress post, sample on the wet method), washing discards water lotion; 50% alcohol is washed, flow velocity 5ml/min, every 30ml collects 1 part, each flow point is carried out high performance liquid chromatography (HPLC) detect (detection method is with 5), merge the identical and purity of retention time greater than 95% component, concentrating under reduced pressure promptly gets highly purified momordica grosvenori glycoside V 623mg, is 95.3% through checking its purity.
Embodiment 3
Present embodiment 3 is implemented under following implementation condition and technical requirements condition:
1. Grosvenor Momordica dry fruit 1Kg adds the industrial alcohol refluxing extraction 4h of 7.5L 80%, filter, filtrate recycling ethanol (can be used for medicinal material extract once more), medicinal extract.Repeat aforesaid operations 1 time, get pure medicinal extract 133g.
2. get pure medicinal extract, add the aqueous suspension of 998mL, use the water saturated ethyl acetate extraction of 749mL volume then, the separating ethyl acetate layer, reclaim under reduced pressure ethyl acetate (can be used for extraction once more) gets medicinal extract.Repeat aforesaid operations 1 time, get ethyl acetate medicinal extract 18g.
3. to continue to use water saturated n-butanol extraction, consumption be 749mL to the aqueous solution behind the ethyl acetate extraction.Isolate propyl carbinol, reclaim propyl carbinol (can be used for extraction once more), repeat aforesaid operations 1 time, merge medicinal extract and get propyl carbinol medicinal extract 21g.
With propyl carbinol medicinal extract with water dissolution after, by 840g 60-100 order polyamide column (column diameter 6.5cm, dry column-packing, sample on the wet method) is housed, is washed to no momordica grosvenori glycoside V and flows out that (the detection method thin layer detects the silica gel G thin layer and detects, developping agent CHCl 3-MeOH-H 2O (65: 30: 5, the Rf of momordica grosvenori glycoside V is 0.4) collects effluent liquid and water lotion.Solvent is to the greatest extent received in decompression, gets thick saponin(e 17g.
5. thick saponin(e is carried out silica gel column chromatography, silica gel 200-300 order, consumption is 1105g (column diameter 6.5cm, wet method dress post, the dry method upper prop), chloroform-methanol-water (65: 30: 3) wash-out, flow velocity 5ml/min, every 50ml collects 1 part, and collection contains momordica grosvenori glycoside V, and (detection method: high performance liquid chromatography (HPLC) method is a weighting agent with the octadecyl silane in the component more than 40%; With acetonitrile-water is moving phase at 24: 76; The detection wavelength is 210nm, flow velocity 1.0ml/min), merge, decompression and solvent recovery gets Momordia grosvenori aglycone v crude product 2.9g.
6. get Momordia grosvenori aglycone v crude product and carry out reversed phase column chromatography, the reverse phase silica gel consumption is a 362.5g (silica gel particle diameter: 200-300 order; Column diameter 6.0cm, wet method dress post, sample on the wet method), washing discards water lotion; 35% alcohol is washed, flow velocity 3ml/min, every 20ml collects 1 part, each flow point is carried out high performance liquid chromatography (HPLC) detect (detection method is with 5), merge the identical and purity of retention time greater than 95% component, concentrating under reduced pressure promptly gets highly purified momordica grosvenori glycoside V 561mg, is 96.1% through checking its purity.
Embodiment 4
Present embodiment 4 is implemented under following implementation condition and technical requirements condition:
1. Grosvenor Momordica dry fruit 1Kg adds the industrial alcohol refluxing extraction 3h of 5L 95%, filter, filtrate recycling ethanol (can be used for medicinal material extract once more), medicinal extract.Repeat aforesaid operations 1 time, get pure medicinal extract 86g.
2. get pure medicinal extract, add the aqueous suspension of 860mL, use the water saturated ethyl acetate extraction of 860mL volume then, the separating ethyl acetate layer, reclaim under reduced pressure ethyl acetate (can be used for extraction once more) gets medicinal extract.Repeat aforesaid operations 1 time, get ethyl acetate medicinal extract 15g.
3. to continue to use water saturated n-butanol extraction, consumption be 430mL to the aqueous solution behind the ethyl acetate extraction.Isolate propyl carbinol, reclaim propyl carbinol (can be used for extraction once more), repeat aforesaid operations 1 time, merge medicinal extract and get propyl carbinol medicinal extract 20g.
With propyl carbinol medicinal extract with water dissolution after, by 960g 60-100 order polyamide column (column diameter 6.5cm, dry column-packing, sample on the wet method) is housed, is washed to no momordica grosvenori glycoside V and flows out that (the detection method thin layer detects the silica gel G thin layer and detects, developping agent CHCl 3-MeOH-H 2O (65: 30: 5, the Rf of momordica grosvenori glycoside V is 0.4) collects effluent liquid and water lotion.Solvent is to the greatest extent received in decompression, gets thick saponin(e 14.5g.
5. thick saponin(e is carried out silica gel column chromatography, silica gel 200-300 order, consumption is 1150g (column diameter 6.5cm, wet method dress post, the dry method upper prop), chloroform-methanol-water (65: 30: 3) wash-out, flow velocity 5ml/min, every 50ml collects 1 part, and collection contains momordica grosvenori glycoside V, and (detection method: high performance liquid chromatography (HPLC) method is a weighting agent with the octadecyl silane in the component more than 40%; With acetonitrile-water is moving phase at 24: 76; The detection wavelength is 210nm, flow velocity 1.0ml/min), merge, decompression and solvent recovery gets Momordia grosvenori aglycone v crude product 2.5g.
6. get Momordia grosvenori aglycone v crude product and carry out reversed phase column chromatography, the reverse phase silica gel consumption is a 300g (silica gel particle diameter: 200-300 order; Column diameter 6.0cm, wet method dress post, sample on the wet method), washing discards water lotion; 40% alcohol is washed, flow velocity 3ml/min, every 20ml collects 1 part, each flow point is carried out high performance liquid chromatography (HPLC) detect (detection method is with 5), merge the identical and purity of retention time greater than 95% component, concentrating under reduced pressure promptly gets highly purified momordica grosvenori glycoside V 525mg, is 97.1% through checking its purity.

Claims (9)

1. a method for preparing high-purity Momordia grosvenori aglycone V from Grosvenor Momordica is characterized in that, specifically comprises the steps:
(1) earlier mangosteen powder is broken into meal, adds the alcohol reflux 2h-6h of 5-10 70%-95% doubly, filter, reclaim ethanol and get pure medicinal extract;
(2) pure medicinal extract is suspended in water, with water saturated ethyl acetate extraction 1 time-3 times, the 0.5-1.0 that each ethyl acetate volume is an aqueous solution volume doubly reclaims the ethyl acetate mother liquor;
(3) continue with 1 time-3 times last step mother liquors of water saturated n-butanol extraction, the 0.5-1.0 that each propyl carbinol volume is an aqueous solution volume doubly reclaims propyl carbinol and gets propyl carbinol medicinal extract;
(4) with propyl carbinol medicinal extract by polyamide column, be washed to no momordica grosvenori glycoside V and wash out, water lotion concentrate saponin(e slightly;
(5) thick saponin(e carries out silica gel column chromatography, chloroform-methanol-water elution, and collection contains momordica grosvenori glycoside V in the component more than 40%, merges, and reclaims solvent, gets Momordia grosvenori aglycone v crude product;
(6) get Momordia grosvenori aglycone v crude product and carry out the C18 reversed-phase silica gel column chromatography, washing, ethanol elution is collected purity at the flow point 95% or more, merges the identical component of retention time, and the recovery solvent promptly gets purity greater than 95% momordica grosvenori glycoside V.
2. the method for preparing high-purity Momordia grosvenori aglycone V from Grosvenor Momordica as claimed in claim 1 is characterized in that, the pure medicinal extract described in the step (2) is suspended in water, and water consumption is 5-10 a times of pure medicinal extract weight.
3. the method for preparing high-purity Momordia grosvenori aglycone V from Grosvenor Momordica as claimed in claim 1 is characterized in that, propyl carbinol medicinal extract described in the step (4) is by polyamide column, and the consumption of polymeric amide is 20-60 a times of propyl carbinol medicinal extract weight.
4. the method for preparing high-purity Momordia grosvenori aglycone V from Grosvenor Momordica as claimed in claim 1 is characterized in that, in the step (4), detect and describedly be washed to the testing conditions that no momordica grosvenori glycoside V washes out and be: detect with the silica gel G thin layer, developping agent is selected CHCl for use 3-MeOH-H 2O, proportioning is 65: 30: 5, the Rf of momordica grosvenori glycoside V is 0.4.
5. the method for preparing high-purity Momordia grosvenori aglycone V from Grosvenor Momordica as claimed in claim 1 is characterized in that, in the described silicagel column of step (5), the silica gel consumption is 30-100 a times of thick saponin(e weight; Each ratio of chloroform-methanol-water elution is 65: 30: 1-65: 30: 5.
6. the method for preparing high-purity Momordia grosvenori aglycone V from Grosvenor Momordica as claimed in claim 1 is characterized in that, collects in the step (5) to contain momordica grosvenori glycoside V in the component more than 40%, and it is collected detection method and selects high performance liquid chromatography for use.
7. the method that from Grosvenor Momordica, prepares high-purity Momordia grosvenori aglycone V as claimed in claim 6, it is characterized in that, the testing conditions of described high performance liquid chromatography is: be weighting agent with the octadecyl silane, acetonitrile-water with 24: 76 ratios is a moving phase, the detection wavelength is 210nm, flow velocity 1.0ml/min.
8. the method for preparing high-purity Momordia grosvenori aglycone V from Grosvenor Momordica as claimed in claim 1 is characterized in that, alcohol concn is 20%-50% in the step (6).
9. as each described method that from Grosvenor Momordica, prepares high-purity Momordia grosvenori aglycone V of claim 1 to 8, it is characterized in that, step (1) but repetitive operation 1 time-2 times.
CN200710039130A 2007-04-05 2007-04-05 Method for preparing high-purity Momordia grosvenori aglycone from Momordia grosvenori Expired - Fee Related CN101029071B (en)

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