CN1844095A - Method for extracting dihydro-quercetin from larch - Google Patents
Method for extracting dihydro-quercetin from larch Download PDFInfo
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- CN1844095A CN1844095A CN 200610035280 CN200610035280A CN1844095A CN 1844095 A CN1844095 A CN 1844095A CN 200610035280 CN200610035280 CN 200610035280 CN 200610035280 A CN200610035280 A CN 200610035280A CN 1844095 A CN1844095 A CN 1844095A
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Abstract
The invention provides a method of extracting dihydroquercetin from eastern larch, this method using water as extractant, extracting xingan eastern larch contains dihydroquercetin, liquid-liquid extracting the produced aquosity extract, adsorption decolouring methyl tert-butyl ether tobacco extract by activated char or active clay, stripping the dissolvant of decolourized methyl tert-butyl ether tobacco extract in vaccum, the grease thing of water stripped is crystallization purified by water and getting rude product of dihydroquercetin. According to need, the getted rude product of dihydroquercetin can be recrystallization purified by water and getting elaboration product of dihydroquercetin. The method of this invention has prominant technique effect, not only the yield is as high as 1.69%-2.0%, but also the getted rude product of dihydroquercetin's purity is as high as 95%-96%, the purified elaboration product of dihydroquercetin can reach the purity of 99%.
Description
Technical field
The present invention relates to from plant, extract dihydroquercetin, be specifically related to from tamarack, extract dihydroquercetin.
Background technology
Dihydroquercetin (Dihydroquercetin; 2-(3,4-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-4H-benzopyran-4-one), chemical molecular formula: C
15H
12O
7, structural formula is as follows:
Dihydroquercetin is one of Vitamin P complex, be a kind of potent antioxidant, can also can be widely used as the sanitas of food at industrial knock-compound and the stablizer thereof that is used for engine raw material and jet raw material, also can be pharmaceutically being used to improve erythrocytic activity, to delay the aging of human body.Russia introduced dihydroquercetin in 2003 in people's circulation system disease, ischemic heart disease, ischemia arteriosclerosis, liver moving obstacle, ophthalmology disease, diabetes and prevention and the treatment tumour better curative effect being arranged all in the pharmacopeia.
2004, people such as Jin Jianzhong disclose a kind of method of dihydroquercetin of extracting (referring to " extraction of dihydroquercetin and evaluation in the tamarack " from tamarack, Jin Jianzhong etc., " Zhejiang forestry science and technology ", Vol.24, No.5, Sep.2004) basic step of this method is: at 80 ℃ of following waters tamarack is carried out extracted twice, united extraction liquid 1.; 2. with precipitation agent dihydroquercetin is extracted; 3. add dissolving with hydrochloric acid, use ethyl acetate extraction, concentrate; 4. use the hot water dissolving, crystallisation by cooling.Although the purity of dihydroquercetin can be big by 97% in this method products obtained therefrom, because its precipitation agent usage quantity too big (be product volume 1000 times), so had a strong impact on the productive rate of product, only can obtain 0.29% productive rate; In addition, the technology contents of key in the technical process, promptly employed precipitation agent are not open.
Summary of the invention
Technical problem to be solved by this invention is to improve the extraction yield that extracts dihydroquercetin from tamarack.
The technical solution that the present invention addresses the above problem is:
A kind of method of extracting dihydroquercetin from tamarack may further comprise the steps:
(1) larch in Xinanlin area of getting the above 0.0m～1.5m in ground is set section, is broken into chip;
Under (2) 70～90 ℃, extract twice continuously, each 0.5～1.5 hour, obtain extracting solution I and secondary raffinate II successively with the secondary raffinate of 6～10 times water or last technical process;
Under (3) 40～50 ℃, by the mixed solution of 10: 1～2 volume ratio methylate tertbutyl ethers extraction extracting solution I or extracting solution I and extracting solution II, the phase of anhydrating gets extraction liquid;
(4) the gained extraction liquid adds sorbent material by the proportioning of 0.5～1.0kg/100L, and adsorption bleaching under the room temperature filters;
(5) the extraction liquid filtrate behind the decolorization filtering is 35 ℃ in initial temperature, and outlet temperature is 85 ℃ of condition and ranges, deviates from solvent under the vacuum of 0.015MPa, is concentrated into paste;
(6) the gained paste adds entry in the ratio of 10～30L/g, 70～90 ℃ of dissolvings down, is cooled to 3～8 ℃ of crystallizations again, filters, and drying at room temperature gets the dihydroquercetin raw product.
The raw product of technique scheme gained of the present invention is cooled to 3～8 ℃ of recrystallizations with 70～90 ℃ of dissolvings down of 10～20 times of water, filters the dry dihydroquercetin highly finished product that get then.
Method of the present invention, the mixed solution of the described extracting solution I of step (3) or extracting solution I and extracting solution II and the volume ratio of methyl tertiary butyl ether be preferably 10: 1.4～and 2.
Method of the present invention, the described sorbent material of step (4) is activated carbon or carclazyte, is preferably activated carbon.The consumption of described sorbent material is preferably 0.7～1.0kg/100L.
Of the present invention is that fragmentation obtains in the usual way with the tamarack chip, also tamarack sawdust or wood shavings.
The tamarack of the present invention place of production can be Daxing'an Mountainrange, the Xiaoxinanlin Mountains, is good with the larch in Xinanlin area in Daxing'an Mountainrange.The described tamarack age of tree is got the above 0.0m in ground～1.5m and is set section more than 40 years, and the time that distance is cut down trees is also to be no more than 2 years for good.
The secondary raffinate that last technical process of the present invention produces is meant the extracting solution II of gained in a last process flow steps (2).The conserve water of first advantage of doing like this, second advantage is to extract the most degree of carrying that improves raw material repeatedly.
Dihydroquercetin raw product of the present invention can be used as food " functional additive ", and described dihydroquercetin highly finished product can be used as " medicine material with nourishing function ".
The method of the invention has following outstanding advantage and significant technique effect than prior art:
1, product stability is good, purity is high, and raw product purity can reach 95%～96%, and highly finished product purity can reach 99%;
2, because the tree section that the present invention chooses the above 0.0m～1.5m in larch in Xinanlin area ground is a raw material, and adopted liquid-liquid low-temperature extraction technology, dissolved dihydroquercetin in the water is extracted in the methyl tertiary butyl ether to greatest extent, thereby the yield that makes product is up to 1.69%～2.0%;
3, extraction agent methyl tertiary butyl ether, not only its price is relatively cheap, and is nontoxic, is insoluble in water, and boiling point low (only being 52 ℃), and making production process is to carry out at low temperatures, and resulting dihydroquercetin has natural structure;
4, extraction agent methyl tertiary butyl ether, the ethyl acetate used with respect to prior art, acetone equal solvent flash-point height are so security is good.
Description of drawings:
Fig. 1 is the high-efficient liquid phase chromatogram spectrum of the standard model of Russia's purchase;
Fig. 2 is the high-efficient liquid phase chromatogram spectrum of following embodiment 1 gained dihydroquercetin raw product.
Embodiment
Below describe the present invention by specific embodiment, make those skilled in the art understand the present invention more comprehensively, but the present invention do not done any type of restriction.
Embodiment 1
It is the stainless steel vessel of 40L that the Xiaoxinanlin Mountains tamarack sawdust 1kg that gets the above 0.0m in ground～1.5m tree paragraph places volume, add entry 10L (10 times of water), soaked 40 minutes down at 85 ℃, centrifugation must contain extracting solution of 0.21% dihydroquercetin (extracting solution I) 8.4L, among the extracting solution I; Add in the residue again and enter 8.5L water, 87 ℃ soak 30 minutes down after, centrifugation must contain secondary raffinate (extracting solution II) 9.0L of 0.045% dihydroquercetin, as the soak solution of new next time tamarack chip.Under 45 ℃, in extracting solution, add methyl tertiary butyl ether 1.2L, stirred 30 minutes, static 30 minutes, separate organic phase methyl tertiary butyl ether extraction liquid 1.13L.Add the 10g gac then and stir decolouring 30 minutes in organic phase, insert after the filtration in the rotatory evaporator, (0.015MPa) initial temperature is 40 ℃ under vacuum state, and outlet temperature is to deviate from solvent under 80 ℃ the condition, paste 45.5g.Add 85 ℃ of water of 1000mL at last again, stirred 15 minutes, be cooled to 5 ℃, treat that lurid dihydroquercetin crystallization separates out, filter to such an extent that filter cake at room temperature carries out drying and obtains yellow powder powder dihydroquercetin raw product 17.8g.
The yellow powder powder dihydroquercetin raw product of gained is detected with FTIR-8300 type Fu Li leaf infrared spectrometer (Japan) earlier, obtain IR (KBr) cm
-1: 3430,1639,1613,1514,1475,972,778; The WRS-1 type melting point detector mensuration product fusing point of using marine products again is 228 ℃.Resulting these two groups of data and document " extraction of dihydroquercetin and evaluation in the tamarack " (Jin Jianzhong etc., " Zhejiang forestry science and technology ", Vol.24, No.5, Sep.2004) middle dihydroquercetin data consistent is so be defined as dihydroquercetin.
Be standard specimen (content is 95%) with resulting dihydroquercetin raw product with " the intend vitamin b6 usp biological products company limited " standard model in Russian cloth city again, adopt C
8Column liquid chromatographic, under the room temperature condition, with methyl alcohol: water=85: 15 is moving phase, detect wavelength 254nm and compare detection, the high-efficient liquid phase chromatogram that obtains the standard model of Russia's purchase is composed as shown in Figure 1, and the high-efficient liquid phase chromatogram that obtains present embodiment gained dihydroquercetin raw product is composed as shown in Figure 2.Fig. 1 is that the 3.744min place has absorption peak in retention time, and its relative peak area is 93.89%, and Fig. 2 is that the 3.745min place has absorption peak in retention time, and its relative peak area is 94.35%, is 95% so demarcate present embodiment gained dihydroquercetin raw product purity.Further calculating the dihydroquercetin productive rate with input raw material tamarack sawdust weight again is 1.69%.
Embodiment 2
The Daxing'an Mountainrange fallen leaves pine tree section of getting the above 0.0m in ground～1.5m tree paragraph is broken into median size for being of a size of the chip of 3 * 3 * 3mm, getting the 1kg chip, to place volume be the stainless steel vessel of 40L, add the secondary raffinate 9.0L among the embodiment 1, soaked 30 minutes down at 82 ℃, separate an extracting solution 7.8L; Add 9.0L water in the filter residue and carry out second extraction, filter the 9.0L secondary raffinate, as the soak solution of new next time tamarack chip.
42 ℃ of following adding methyl tertiary butyl ether 1.5L in the above-mentioned extracting solution stirred 20 minutes, left standstill 20 minutes, separate organic phase methyl tertiary butyl ether extraction liquid 1.41L.Add the 10g gac and stir decolouring 30 minutes in organic phase, the organic phase filtrate after the filtration adds in the rotatory evaporator, and (0.015MPa) initial temperature is 40 ℃ under vacuum state, and outlet temperature is to deviate from solvent under 85 ℃ the condition, paste 63.7g; Add 85 ℃ of water of 800mL, stir after 15 minutes, be cooled to 3 ℃, treat that light yellow dihydroquercetin crystallization separates out, filter to such an extent that filter cake at room temperature carries out drying, obtain yellow powder powder dihydroquercetin raw product 21.2g.It is 96% that resulting dihydroquercetin raw product adopts embodiment 1 described method to record its purity, and productive rate is 2.04%, and the product fusing point is 227 ℃.
Above-mentioned dihydroquercetin raw product joined in 300mL85 ℃ the water, stirred 15 minutes, be cooled to 3 ℃, get dihydroquercetin highly finished product 20.1g behind the filtration drying, adopting embodiment 1 described method to record purity is 99%, and the product fusing point is 225 ℃, and productive rate is 2.0%.
Embodiment 3
Get the Daxing'an Mountainrange tamarack wood shavings 1kg of the above 0.0m in ground～1.5m tree paragraph, add the secondary raffinate 6.0L among the embodiment 2, soaked 60 minutes down at 90 ℃, centrifugation gets extracting solution 5.3L No. one time; Add 6.0L water in the filter residue and carry out second extraction, get the 5.9L secondary raffinate, the secondary raffinate conduct of gained is the soak solution of new tamarack chip next time.
In an extracting solution of 40 ℃, add methyl tertiary butyl ether 0.6L, stirred 15 minutes, left standstill 20 minutes, separate methyl tertiary butyl ether ether extraction liquid 0.56L; Add the 30g gac and stir decolouring 30 minutes, filter.
With filtrate (0.015MPa) under vacuum state, initial temperature is 50 ℃, outlet temperature is to deviate from solvent under 70 ℃ the condition, get paste 58.5g, add the water of 70 ℃ of 1.5L in the paste, stirred 10 minutes, be cooled to 8 ℃, filter filter cake at room temperature carry out drying, yellow powder powder dihydroquercetin 22.1g.It is 95% that resulting dihydroquercetin raw product adopts embodiment 1 described method to record its purity, and productive rate is 2.1%, and the product fusing point is 228 ℃.
Above-mentioned dihydroquercetin raw product is joined in the water of 70 ℃ of 225mL, stirred 10 minutes, be cooled to 8 ℃, get dihydroquercetin highly finished product 21.3g behind the filtration drying, adopting embodiment 1 described method to record purity is 99%, and the product fusing point is 225 ℃, and productive rate is 2.11%.
Embodiment 4
Get the Daxing'an Mountainrange tamarack sawdust 1kg of the above 0.0m in ground～1.5m tree paragraph, add the secondary raffinate 7.0L among the embodiment 3, soaked 100 minutes down at 70 ℃, centrifugation gets extracting solution 6.3L No. one time; Add 7.0L water and carry out second extraction in filter residue, get the 7.1L secondary raffinate, the secondary raffinate conduct of gained is the soak solution of new tamarack chip next time.
In extracting solution, adding methyl tertiary butyl ether 0.9L under 43 ℃, stir, standing demix, separate organic phase methyl tertiary butyl ether ether extraction liquid 0.83L;
In above-mentioned organic phase, add the 31g gac, stir decolouring 30 minutes, filter; Filtrate is (0.015MPa) under vacuum state, and initial temperature is 40 ℃, and outlet temperature is that 80 ℃ condition is deviate from solvent, gets paste 60.5g.In paste, add in 80 ℃ of water of 0.9L, stirred 10 minutes, be cooled to 6 ℃, filter filter cake, under the room temperature filter cake is carried out drying, get yellow powder powder dihydroquercetin raw product 22.4g, adopting embodiment 1 described method to record purity is 95.5%, the product fusing point is 227 ℃, and productive rate is 2.14%.
Above-mentioned dihydroquercetin raw product is joined in the water of 80 ℃ of 0.4L, stirred 10 minutes, be cooled to 6 ℃, get dihydroquercetin highly finished product 21.0g behind the filtration drying, adopting embodiment 1 described method to record purity is 99%, and the product fusing point is 225 ℃.Productive rate is 2.08%.
Embodiment 5
It is the stainless steel vessel of 40L that the Daxing'an Mountainrange tamarack wood shavings 1kg that gets the above 0.0m in ground～1.5m tree paragraph places volume, adds the secondary raffinate 7.0L among the embodiment 4, soaks 60 minutes down at 85 ℃, and filtering separation gets extracting solution 6.3L No. one time; Add 10L water in the filter residue and carry out second extraction, filter the soak solution that the 9.7L secondary raffinate that obtains can be used as fresh tamarack chip.
Add methyl tertiary butyl ether 1.0L down in an above-mentioned extracting solution at 42 ℃, stirred 30 minutes, left standstill 30 minutes, layering gets methyl tertiary butyl ether extraction liquid 0.7L.Add the 5g atlapulgite in the methyl tertiary butyl ether extraction liquid, stir 35 minutes after-filtration of decolouring, filtrate adds in the rotatory evaporator, under vacuum state (0.015MPa), initial temperature is 45 ℃, and outlet temperature is to deviate from solvent under 80 ℃ the condition, paste 65.1g; Add 80 ℃ of water of 0.8L, stirs after 20 minutes, be cooled to 5 ℃, treat that light yellow dihydroquercetin crystallization separates out, the filter cake that filtration obtains at room temperature carries out drying, and drying obtains yellow powder powder dihydroquercetin raw product 19.8g.It is 95% that resulting dihydroquercetin raw product adopts embodiment 1 described method to record its purity, and productive rate is 1.81%, and the product fusing point is 228 ℃.
Embodiment 6
It is the stainless steel vessel of 40L that the Xiaoxinanlin Mountains tamarack sawdust 1kg that gets the above 0.0m in ground～1.5m tree paragraph places volume, adds 10L water, soaks 40 minutes down at 90 ℃, filters to such an extent that contain extracting solution of 0.20% dihydroquercetin (extracting solution I) 8.6L; Add in the residue again and enter 10L water, after soaking 40 minutes under 85 ℃, filter to such an extent that contain secondary raffinate (extracting solution II) 10L of 0.036% dihydroquercetin, the extracting solution of above-mentioned secondary is merged, must contain the mixed extract 18.6L of 0.112% dihydroquercetin.
Under 45 ℃, add methyl tertiary butyl ether 3.5L in the above-mentioned 18.6L extracting solution, stirred 30 minutes, static 50 minutes, separate organic phase methyl tertiary butyl ether extraction liquid 2.7L.Add the 20g gac then and stir decolouring 30 minutes in organic phase, insert after the filtration in the rotatory evaporator, (0.015MPa) initial temperature is 40 ℃ under vacuum state, and outlet temperature is to deviate from solvent under 80 ℃ the condition, paste 53.7g.Add 80 ℃ of water of 1.5L at last again, stirred 15 minutes, be cooled to 5 ℃, treat that lurid dihydroquercetin crystallization separates out, filter to such an extent that filter cake at room temperature carries out drying and obtains yellow powder powder dihydroquercetin raw product 22.3g.It is 95.3% that resulting dihydroquercetin raw product adopts embodiment 1 described method to record its purity, and the product fusing point is 226 ℃, and product yield is 2.13%.
Above-mentioned dihydroquercetin raw product is joined in the water of 80 ℃ of 0.44L, stirred 15 minutes, be cooled to 5 ℃, get dihydroquercetin highly finished product 21.2g behind the filtration drying, adopting embodiment 1 described method to record purity is 99%, and the product fusing point is 225 ℃.Productive rate is 2.1%.
Claims (6)
1. method of extracting dihydroquercetin from tamarack may further comprise the steps:
(1) larch in Xinanlin area of getting the above 0.0m～1.5m in ground is set section, is broken into chip;
Under (2) 70～90 ℃, extract twice continuously, each 0.5～1.5 hour, obtain extracting solution I and secondary raffinate II successively with the secondary raffinate of 6～10 times water or last technical process;
Under (3) 40～50 ℃, by the mixed solution of 10: 1～2 volume ratio methylate tertbutyl ethers extraction extracting solution I or extracting solution I and extracting solution II, the phase of anhydrating gets extraction liquid;
(4) the gained extraction liquid adds sorbent material by the proportioning of 0.5～1.0kg/100L, and adsorption bleaching under the room temperature filters;
(5) the extraction liquid filtrate behind the decolorization filtering is 35 ℃ in initial temperature, and outlet temperature is 85 ℃ of condition and ranges, deviates from solvent under the vacuum of 0.015MPa, is concentrated into paste;
(6) the gained paste adds entry in the ratio of 10～30L/g, 70～90 ℃ of dissolvings down, is cooled to 3～8 ℃ of crystallizations again, filters, and drying at room temperature gets the dihydroquercetin raw product.
2. according to the described a kind of method of extracting dihydroquercetin from tamarack of claim 1, the raw product that it is characterized in that gained is cooled to 3～8 ℃ of recrystallizations again with 70～90 ℃ of dissolvings down of 10～20 times of water, filters the dry dihydroquercetin highly finished product that get then.
3. according to the described method of claim 1, it is characterized in that the mixed solution of the described extracting solution I of step (3) or extracting solution I and extracting solution II and the volume ratio of methyl tertiary butyl ether are 10: 1.4～2.
4. according to the described a kind of method of from tamarack, extracting dihydroquercetin of claim 1, it is characterized in that the described sorbent material of step (4) is activated carbon or carclazyte.
5. according to the described a kind of method of from tamarack, extracting dihydroquercetin of claim 4, it is characterized in that described sorbent material is an activated carbon.
6. according to claim 1,4 or 5 described a kind of methods of from tamarack, extracting dihydroquercetin, it is characterized in that the usefulness of described sorbent material. amount is 0.7～1.0kg/100L.
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| CN101157733B (en) * | 2007-11-21 | 2010-04-21 | 林琳 | Method for abstracting dihydroquercetin and arabinogalactan from larch and processing residual thereof |
| CN101851221A (en) * | 2010-05-27 | 2010-10-06 | 东北林业大学 | Method for preparing dihydroquercetin from larches |
| CN101863869A (en) * | 2010-06-03 | 2010-10-20 | 东北林业大学 | Method for extracting dihydroquercetin from larch sheets |
| CN101333204B (en) * | 2007-06-29 | 2011-05-11 | 黑龙江花旗科技发展有限公司 | Method for extracting dihydroquercetin form larch |
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| CN102924420A (en) * | 2012-10-25 | 2013-02-13 | 沈立乾 | Method for extracting dihydroquercetin from root of dahurian larch |
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| KR100523562B1 (en) * | 2001-10-29 | 2005-10-25 | 한국과학기술연구원 | Neuroprotective composition comprising an extract from opuntia ficus-indica and compounds isolated therefrom |
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| CN101333204B (en) * | 2007-06-29 | 2011-05-11 | 黑龙江花旗科技发展有限公司 | Method for extracting dihydroquercetin form larch |
| CN101157733B (en) * | 2007-11-21 | 2010-04-21 | 林琳 | Method for abstracting dihydroquercetin and arabinogalactan from larch and processing residual thereof |
| CN101851221A (en) * | 2010-05-27 | 2010-10-06 | 东北林业大学 | Method for preparing dihydroquercetin from larches |
| CN101851221B (en) * | 2010-05-27 | 2012-09-05 | 东北林业大学 | Method for preparing dihydroquercetin from larches |
| CN101863869A (en) * | 2010-06-03 | 2010-10-20 | 东北林业大学 | Method for extracting dihydroquercetin from larch sheets |
| CN102746263B (en) * | 2012-06-04 | 2015-04-01 | 陈秀海 | Preparation method for taxifolin |
| CN102746263A (en) * | 2012-06-04 | 2012-10-24 | 陈秀海 | Preparation method for taxifolin |
| CN102924420A (en) * | 2012-10-25 | 2013-02-13 | 沈立乾 | Method for extracting dihydroquercetin from root of dahurian larch |
| CN102924420B (en) * | 2012-10-25 | 2013-09-04 | 沈立乾 | Method for extracting dihydroquercetin from root of dahurian larch |
| WO2014063504A1 (en) * | 2012-10-25 | 2014-05-01 | Shen Liqian | Method for extracting dihydroquercetin from the root of larch trees |
| US9206152B2 (en) | 2012-10-25 | 2015-12-08 | Liqian Shen | Method for extracting dihydroquercetin from the root of larch trees |
| CN105409972A (en) * | 2015-11-16 | 2016-03-23 | 湖南广播电视大学 | Compositions for promoting accumulation of anthocyanin in roselle calyx |
| CN111205169A (en) * | 2019-10-25 | 2020-05-29 | 绍兴文理学院元培学院 | Refining process of natural borneol |
| CN111205169B (en) * | 2019-10-25 | 2022-11-29 | 绍兴文理学院元培学院 | Refining process of natural borneol |
| CN116987056A (en) * | 2023-07-17 | 2023-11-03 | 黑龙江儒泰科技发展有限责任公司 | Method for extracting dihydroquercetin from larch |
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