CN103524463A - Method for rapidly preparing great burdock achene aglycone from great burdock achene - Google Patents
Method for rapidly preparing great burdock achene aglycone from great burdock achene Download PDFInfo
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- CN103524463A CN103524463A CN201310447928.XA CN201310447928A CN103524463A CN 103524463 A CN103524463 A CN 103524463A CN 201310447928 A CN201310447928 A CN 201310447928A CN 103524463 A CN103524463 A CN 103524463A
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
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Abstract
The invention relates to a method for rapidly preparing great burdock achene aglycone from great burdock achene. The method comprises the steps as follows: (1), smashed great burdock achene powder is extracted and filtered by tap water, an aqueous solution is removed, and great burdock achene dregs are obtained through draining; (2), ethyl alcohol is added into the great burdock achene dregs for extraction, and an extracting solution is obtained after filtering; (3), the extracting solution is subjected to pressure reduction and evaporation to dryness until the extracting solution is in constant weight, and a great burdock achene aglycone extract is obtained; (4),100-300 meshes of silicagel columns are formed by the great burdock achene aglycone extract with a dry method; (5), the silicagel columns are eluted by petroleum ether, acetone with 20% of mass concentration and an acetone solution with 40% of mass concentration, and 40% of acetone eluent is collected; and (6), a refined great burdock achene aglycone extract after the eluent is subjected to pressure reduction and evaporation to dryness until the eluent is in constant weight is obtained; absolute ethyl alcohol-petroleum ether-acetone is added into the refined great burdock achene aglycone extract for recrystallization, the still standing is performed for 2-96 hours, and great burdock achene aglycone prism crystals are obtained in a ventilated cabinet. The method has a simple technology, good safety performance and good repeatability.
Description
Technical field
The present invention relates to a kind of method of extracting l-arctigenin, relate in particular to a kind of method of preparing fast l-arctigenin from Great Burdock Achene.
Background technology
Great Burdock Achene be feverfew burdock (
arctium lappa L) dry mature fruit, belong to pungent and cold medicine for relieving the exterior syndrome, the effect of tool dispelling wind and heat pathogens, a surname's lung promoting eruption, subduing swelling and detoxicating, is used for the treatment of that common cold due to wind-heat, expectoration are many, swelling and pain in the throat, macula is saturating, rubella is had an itch, carbuncle sore tumefacting virus Deng Zheng， China is widely distributed.Research data shows, in Great Burdock Achene, main chemical compositions has arctinin, l-arctigenin, diisobutyl phthalate, 9-12,15-punicic acid, hexacosanoic acid, ethyl linoleate, octadecanoic acid glyceryl ester [Qi Yanming, Bai Ling, Zhang Wenzhi, Qiqihar University's journal, 2012,28 (2): 19-21].Arctinin and l-arctigenin all have good retarding effect to the skin carcinoma being produced by DMBA (7,12-dimethylbenzanthracene) and TPA (12-O-mnyristoyl-13-acetate) induction.Compare with control group, 10 weeks, l5 week, 20 weeks after medication, the carcinogenic rate of mouse all declines to some extent.After medication 20 weeks, the carcinogenic rate of mouse reduces 50%.L-arctigenin also has obvious restraining effect [Midori Takasaki, Takao Konoshima, et al. Cancer letters.2000,158:23-29] to lung tumor.L-arctigenin can suppress the multiplication capacity of colon cancer cell SW 480 cells, and induction p21 genetic expression rise [peace, Wang Jingmin, western Chinese materia medica, 2012,25(6): 17-20].
At present, the method for extraction l-arctigenin mainly contains microwave extraction, refluxing extraction, supersound extraction, cold soaking extraction, the liquid extraction of ultra-high voltage assisting ion, supercritical CO
2the methods such as extraction, extracting solvent has methyl alcohol and ethanol water etc.Microwave extraction, ultrasonic extraction and solvent methanol are used in l-arctigenin content analysis aspect more, are not suitable for a large amount of preparations of l-arctigenin.Aspect separation and purification, substantially utilize traditional silica gel separated, eluting solvent has chloroform methanol etc., obtains the l-arctigenin monomer time used longer.
Summary of the invention
Technical problem to be solved by this invention is to provide that a kind of technique is simple, security is good prepares fast the method for l-arctigenin from Great Burdock Achene.
For addressing the above problem, a kind of method of preparing fast l-arctigenin from Great Burdock Achene of the present invention, comprises the following steps:
(1) the Great Burdock Achene of pulverizing is extracted 1 ~ 3 time by the solid-liquid mass ratio of 1:5 ~ 20 with tap water at 20 ~ 55 ℃, each 1 ~ 3 hour, after filtering, abandon the aqueous solution, drain, obtain Great Burdock Achene slag;
(2) in described Great Burdock Achene slag, adding mass concentration is 50 ~ 98% alcohol, by the solid-liquid mass ratio of 1:5 ~ 20, extracts 1 ~ 4 time at 75 ~ 85 ℃, each 1 ~ 3 hour, after filtering, merges and obtains extracting solution;
(3) by described extracting solution, in temperature, be that under 40 ~ 80 ℃, the pressure condition that is 0.05 ~ 0.08MPa, evaporated under reduced pressure, to constant weight, obtains l-arctigenin extract;
(4) by (3) l-arctigenin extract dry method loading 100 ~ 300 order silicagel columns of gained of described step;
By described step (4) the silicagel column of gained by sherwood oil, mass concentration, be that 20% acetone, mass concentration are 40% acetone soln wash-out successively, collect 40% acetone elutriant;
By described elutriant through evaporated under reduced pressure to constant weight, obtain l-arctigenin extract medicinal extract; In described l-arctigenin extract medicinal extract, by the solid-to-liquid ratio of 1 g:10 mL ~ 50 mL, add dehydrated alcohol-sherwood oil-acetone to carry out recrystallization, standing 2 ~ 96 hours, be put in ventilating kitchen, obtain l-arctigenin prism-shaped crystal.
The Great Burdock Achene of described step in (1) refers to that granularity 10 ~ 100 objects are dried Great Burdock Achene.
Described step (3) in the condition of evaporated under reduced pressure refer to that temperature is that 40 ~ 80 ℃, pressure are 0.05 ~ 0.08MPa.
Described step (4) in the condition of dry method loading be that the consumption of packing material in silicagel column is 4 ~ 30 times of quality of sample l-arctigenin extract.
The described step (5) flow velocity of middle wash-out is 30 ~ 200mL/min.
Described step (6) in the condition of evaporated under reduced pressure refer to that temperature is that 40 ~ 60 ℃, pressure are 0.05 ~ 0.08MPa.
Described step (6) middle dehydrated alcohol-sherwood oil-acetone three's volume ratio is 1 ~ 3:0 ~ 2:0 ~ 1.
The application of the l-arctigenin that a kind of method of preparing fast l-arctigenin from Great Burdock Achene as above makes in the bulk drug as antitumor and treatment diabetes.
The present invention compared with prior art has the following advantages:
1, the present invention adopts vacuum reactor refluxing extraction, 100 ~ 200 order silica gel separation, sherwood oil acetone as eluting solvent, utilizes crystallization process rapid, high volume to prepare l-arctigenin.
2, the present invention adopts silica gel column chromatography and crystallization recrystallization isolation technique, compares with isolation technique such as high speed adverse current chromatograms (HSCCC), can access a large amount of l-arctigenin monomers, has effectively shortened preparation time (referring to table 1).
Table 1
3, the l-arctigenin stable in properties of the separated preparation of the present invention, purity high (can reach more than 98.5%), can be applicable to medicine, reference material, protective foods and health medicine etc.
(1) outward appearance:
Method: get three batch samples and reference substance visual observation, the results are shown in Table 2
Table 2 visual inspection result
Result: 3 batch samples are white prism-shaped crystallization; Odorless, tasteless, transparent, twist into pieces as white powder.
(2) solubleness:
Method: press Chinese Pharmacopoeia two notes on the use of version (five) lower regulation in 2005.Precision takes that to be ground into the sample of fine powder appropriate, under the condition of 25 ℃, adds a certain amount of solvent, every powerful jolting in approximately 5 minutes 30 seconds, observes the dissolving situation in 30 minutes.The results are shown in Table 3(a, b, c).
Table 3a solubleness is investigated result (lot number 081124)
Table 3b solubleness is investigated result (lot number 081101)
Table 3c solubleness is investigated result (lot number 081220)
Result: l-arctigenin three batch samples, be dissolved in methyl alcohol, ethanol, acetone, is slightly dissolved in trichloromethane, is slightly soluble in water, is dissolved in hardly sherwood oil.
(3) specific rotation:
Method: it is appropriate, accurately weighed to get 3 batch samples, puts in 50mL volumetric flask, adds dissolve with methanol and is diluted to the need testing solution that every 1mL contains 10mg.Pouring length into is in 1dm test tube, measures the specific rotation (two appendix VI E of Chinese Pharmacopoeia version in 2005) of l-arctigenin in accordance with the law.
According to specific optical rotation formula: [α]=α/l*C, wherein l is test tube length, the dm of unit, C is sample concentration, the g mL of unit
-1, α is specific rotation, calculates specific optical rotation, the results are shown in Table 4
Table 4 specific rotation detected result
As a result, the specific rotation of l-arctigenin is in-0.41 ~-0.43 scope.Specific optical rotation is within the scope of-41 ~-43 °.
(4) pH value:
Method: it is appropriate, accurately weighed to get 3 batch samples, is placed in 25mL volumetric flask, adds ultrapure water and makes the solution that 1mL contains 2mg l-arctigenin, measures pH value (two appendix VI H of Chinese Pharmacopoeia version in 2005) in accordance with the law.
Instrument: pHS-3C pH meter (the accurate Science and Technology Ltd. in Shanghai).
Proofread and correct: press pHS-3C pH meter operation instruction, the mixed phosphate salt buffer of PH6.86 and the borax of pH9.18 are proofreaied and correct pH meter, the preci-sion and accuracy of pH meter meets the requirements.The results are shown in Table 5.
Table 5pH value detected result
Conclusion: l-arctigenin pH value is between 6.4 ~ 6.7.
In sum, l-arctigenin is stable in nature.
4, the inventive method technique is simple, security good, repeatability good (repeat four times and prepare l-arctigenin in experimentation, l-arctigenin rate of recovery RSD 0.89%, has good repeatability).
5, present device investment is little, easy to operate, and with low cost.
Embodiment
embodiment 1from Great Burdock Achene, prepare fast a method for l-arctigenin, comprise the following steps:
(1) with tap water, by the solid-liquid mass ratio (g/g) of 1:5, adopt vacuum reactor and oil bath pan (Shaanxi Ao Xin Electronic Science and Technology Co., Ltd.) at 38 ℃, to extract 2 times the Great Burdock Achene of pulverizing, each 1 hour, after filtering, abandon the aqueous solution, drain, obtain Great Burdock Achene slag.
Wherein: Great Burdock Achene refers to that granularity 10 objects are dried Great Burdock Achene.
(2) in Great Burdock Achene slag, adding mass concentration is 50% alcohol, by the solid-liquid mass ratio (g/g) of 1:5, extracts 2 times at 75 ℃, each 1 hour, after filtering, merges and obtains extracting solution.
(3) by extracting solution, in temperature, be that under 40 ℃, the pressure condition that is 0.05MPa, evaporated under reduced pressure, to constant weight, obtains l-arctigenin extract.
(4) by the (3) l-arctigenin extract dry method loading 100 order silicagel columns of gained of step.
Wherein: the device of dry method loading is pneumatic pump, the glass column of diameter 2 ~ 15cm, 24 ~ 64 mouthfuls of ears liquid storage balls of 500 ~ 1000mL, 24 ~ 64 mouthfuls of ears polishing heads, its condition is that the consumption of packing material in silicagel column is 4 times of quality of sample l-arctigenin extract.
By step (4) the silicagel column of gained by sherwood oil, mass concentration, be that 20% acetone, mass concentration are 40% acetone soln wash-out successively, the flow velocity of wash-out is 30mL/min, collects 40% acetone elutriant.
By elutriant through N-1000D Rotary Evaporators temperature be under 40 ℃, the pressure condition that is 0.05MPa through evaporated under reduced pressure to constant weight, obtain l-arctigenin extract medicinal extract; In l-arctigenin extract medicinal extract, by the solid-to-liquid ratio of 1 g:10 mL, add dehydrated alcohol-sherwood oil-acetone to carry out recrystallization, standing 2 hours, be put in ventilating kitchen, obtain l-arctigenin prism-shaped crystal.
Wherein: dehydrated alcohol-sherwood oil-acetone three's volume ratio (mL/ mL) is 3:2:1.
This l-arctigenin is through high effective liquid chromatography for measuring, content 99.5%.
embodiment 2from Great Burdock Achene, prepare fast a method for l-arctigenin, comprise the following steps:
(1) with tap water, by the solid-liquid mass ratio (g/g) of 1:10, adopt vacuum reactor and oil bath pan (Shaanxi Ao Xin Electronic Science and Technology Co., Ltd.) at 35 ℃, to extract 1 time the Great Burdock Achene of pulverizing, each 2 hours, after filtering, abandon the aqueous solution, drain, obtain Great Burdock Achene slag.
Wherein: Great Burdock Achene refers to that granularity 100 objects are dried Great Burdock Achene.
(2) in Great Burdock Achene slag, adding mass concentration is 85% alcohol, by the solid-liquid mass ratio (g/g) of 1:10, extracts 2 times at 80 ℃, each 2 hours, after filtering, merges and obtains extracting solution.
(3) by extracting solution, in temperature, be that under 70 ℃, the pressure condition that is 0.07MPa, evaporated under reduced pressure, to constant weight, obtains l-arctigenin extract.
(4) by the (3) l-arctigenin extract dry method loading 200 order silicagel columns of gained of step.
Wherein: the device of dry method loading is pneumatic pump, the glass column of diameter 2 ~ 15cm, 24 ~ 64 mouthfuls of ears liquid storage balls of 500 ~ 1000mL, 24 ~ 64 mouthfuls of ears polishing heads, its condition is that the consumption of packing material in silicagel column is 10 times of quality of sample l-arctigenin extract.
By step (4) the silicagel column of gained by sherwood oil, mass concentration, be that 20% acetone, mass concentration are 40% acetone soln wash-out successively, the flow velocity of wash-out is 50mL/min, collects 40% acetone elutriant.
By elutriant through N-1000D rotary evaporation temperature be under 60 ℃, the pressure condition that is 0.08MPa through evaporated under reduced pressure to constant weight, obtain l-arctigenin extract medicinal extract; In l-arctigenin extract medicinal extract, by the solid-to-liquid ratio of 1 g:50 mL, add dehydrated alcohol-sherwood oil-acetone to carry out recrystallization, standing 24 hours, be put in ventilating kitchen, obtain l-arctigenin prism-shaped crystal.
Wherein: dehydrated alcohol-sherwood oil-acetone three's volume ratio (mL/ mL) is 2:2:1.
This l-arctigenin is through high effective liquid chromatography for measuring, content 99.2%.
embodiment 3from Great Burdock Achene, prepare fast a method for l-arctigenin, comprise the following steps:
(1) with tap water, by the solid-liquid mass ratio (g/g) of 1:15, adopt vacuum reactor and oil bath pan (Shaanxi Ao Xin Electronic Science and Technology Co., Ltd.) at 38 ℃, to extract 2 times the Great Burdock Achene of pulverizing, each 2 hours, after filtering, abandon the aqueous solution, drain, obtain Great Burdock Achene slag.
Wherein: Great Burdock Achene refers to that granularity 50 objects are dried Great Burdock Achene.
(2) in Great Burdock Achene slag, adding mass concentration is 90% alcohol, by the solid-liquid mass ratio (g/g) of 1:15, extracts 2 times at 85 ℃, each 2 hours, after filtering, merges and obtains extracting solution.
(3) by extracting solution, in temperature, be that under 55 ℃, the pressure condition that is 0.08MPa, evaporated under reduced pressure, to constant weight, obtains l-arctigenin extract.
(4) by the (3) l-arctigenin extract dry method loading 300 order silicagel columns of gained of step.
Wherein: the device of dry method loading is pneumatic pump, the glass column of diameter 2 ~ 15cm, 24 ~ 64 mouthfuls of ears liquid storage balls of 500 ~ 1000mL, 24 ~ 64 mouthfuls of ears polishing heads, its condition is that the consumption of packing material in silicagel column is 20 times of quality of sample l-arctigenin extract.
By step (4) the silicagel column of gained by sherwood oil, mass concentration, be that 20% acetone, mass concentration are 40% acetone soln wash-out successively, the flow velocity of wash-out is 100mL/min, collects 40% acetone elutriant.
By elutriant through N-1000D Rotary Evaporators temperature be under 50 ℃, the pressure condition that is 0.07MPa through evaporated under reduced pressure to constant weight, obtain l-arctigenin extract medicinal extract; In l-arctigenin extract medicinal extract, by the solid-to-liquid ratio of 1 g:40 mL, add dehydrated alcohol-sherwood oil-acetone to carry out recrystallization, standing 2 hours, be put in ventilating kitchen, obtain l-arctigenin prism-shaped crystal.
Wherein: dehydrated alcohol-sherwood oil-acetone three's volume ratio (mL/ mL) is 3:0:0.
This l-arctigenin is through high effective liquid chromatography for measuring, content 99.6%.
embodiment 4from Great Burdock Achene, prepare fast a method for l-arctigenin, comprise the following steps:
(1) with tap water, by the solid-liquid mass ratio (g/g) of 1:20, adopt vacuum reactor and oil bath pan (Shaanxi Ao Xin Electronic Science and Technology Co., Ltd.) at 38 ℃, to extract 1 time the Great Burdock Achene of pulverizing, each 3 hours, after filtering, abandon the aqueous solution, drain, obtain Great Burdock Achene slag.
Wherein: Great Burdock Achene refers to that granularity 80 objects are dried Great Burdock Achene.
(2) in Great Burdock Achene slag, adding mass concentration is 95% alcohol, by the solid-liquid mass ratio (g/g) of 1:5, extracts 2 times at 85 ℃, each 3 hours, after filtering, merges and obtains extracting solution.
(3) by extracting solution, in temperature, be that under 60 ℃, the pressure condition that is 0.08MPa, evaporated under reduced pressure, to constant weight, obtains l-arctigenin extract.
(4) by the (3) l-arctigenin extract dry method loading 150 order silicagel columns of gained of step.
Wherein: the device of dry method loading is pneumatic pump, the glass column of diameter 2 ~ 15cm, 24 ~ 64 mouthfuls of ears liquid storage balls of 500 ~ 1000mL, 24 ~ 64 mouthfuls of ears polishing heads, its condition is that the consumption of packing material in silicagel column is 30 times of quality of sample l-arctigenin extract.
By step (4) the silicagel column of gained by sherwood oil, mass concentration, be that 20% acetone, mass concentration are 40% acetone soln wash-out successively, the flow velocity of wash-out is 200mL/min, collects 40% acetone elutriant.
By elutriant through N-1000D Rotary Evaporators temperature be under 55 ℃, the pressure condition that is 0.06MPa through evaporated under reduced pressure to constant weight, obtain l-arctigenin extract medicinal extract; In l-arctigenin extract medicinal extract, by the solid-to-liquid ratio of 1 g:30 mL, add dehydrated alcohol-sherwood oil-acetone to carry out recrystallization, standing 36 hours, be put in ventilating kitchen, obtain l-arctigenin prism-shaped crystal.
Wherein: dehydrated alcohol-sherwood oil-acetone three's volume ratio (mL/ mL) is 2:2:1.
This l-arctigenin is through high effective liquid chromatography for measuring, content 99.8%.
embodiment 5from Great Burdock Achene, prepare fast a method for l-arctigenin, comprise the following steps:
(1) with tap water, by the solid-liquid mass ratio (g/g) of 1:8, adopt vacuum reactor and oil bath pan (Shaanxi Ao Xin Electronic Science and Technology Co., Ltd.) at 55 ℃, to extract 3 times the Great Burdock Achene of pulverizing, each 3 hours, after filtering, abandon the aqueous solution, drain, obtain Great Burdock Achene slag.
Wherein: Great Burdock Achene refers to that granularity 75 objects are dried Great Burdock Achene.
(2) in Great Burdock Achene slag, adding mass concentration is 98% alcohol, by the solid-liquid mass ratio (g/g) of 1:8, extracts 4 times at 80 ℃, each 1 hour, after filtering, merges and obtains extracting solution.
(3) by extracting solution, in temperature, be that under 80 ℃, the pressure condition that is 0.07MPa, evaporated under reduced pressure, to constant weight, obtains l-arctigenin extract.
(4) by the (3) l-arctigenin extract dry method loading 250 order silicagel columns of gained of step.
Wherein: the device of dry method loading is pneumatic pump, the glass column of diameter 2 ~ 15cm, 24 ~ 64 mouthfuls of ears liquid storage balls of 500 ~ 1000mL, 24 ~ 64 mouthfuls of ears polishing heads, its condition is that the consumption of packing material in silicagel column is 25 times of quality of sample l-arctigenin extract.
By step (4) the silicagel column of gained by sherwood oil, mass concentration, be that 20% acetone, mass concentration are 40% acetone soln wash-out successively, the flow velocity of wash-out is 150mL/min, collects 40% acetone elutriant.
By elutriant through N-1000D Rotary Evaporators temperature be under 60 ℃, the pressure condition that is 0.08MPa through evaporated under reduced pressure to constant weight, obtain l-arctigenin extract medicinal extract; In l-arctigenin extract medicinal extract, by the solid-to-liquid ratio of 1 g:40 mL, add dehydrated alcohol-sherwood oil-acetone to carry out recrystallization, standing 96 hours, be put in ventilating kitchen, obtain l-arctigenin prism-shaped crystal.
Wherein: dehydrated alcohol-sherwood oil-acetone three's volume ratio (mL/ mL) is 1:1:1.
This l-arctigenin is through high effective liquid chromatography for measuring, content 99.5%.
embodiment 6from Great Burdock Achene, prepare fast a method for l-arctigenin, comprise the following steps:
(1) with tap water, by the solid-liquid mass ratio (g/g) of 1:12, adopt vacuum reactor and oil bath pan (Shaanxi Ao Xin Electronic Science and Technology Co., Ltd.) at 20 ℃, to extract 2 times the Great Burdock Achene of pulverizing, each 3 hours, after filtering, abandon the aqueous solution, drain, obtain Great Burdock Achene slag.
Wherein: Great Burdock Achene refers to that granularity 60 objects are dried Great Burdock Achene.
(2) in Great Burdock Achene slag, adding mass concentration is 90% alcohol, by the solid-liquid mass ratio (g/g) of 1:20, extracts 1 time at 80 ℃, each 3 hours, after filtering, merges and obtains extracting solution.
(3) by extracting solution, in temperature, be that under 40 ℃, the pressure condition that is 0.05MPa, evaporated under reduced pressure, to constant weight, obtains l-arctigenin extract.
(4) by the (3) l-arctigenin extract dry method loading 150 order silicagel columns of gained of step.
Wherein: the device of dry method loading is pneumatic pump, the glass column of diameter 2 ~ 15cm, 24 ~ 64 mouthfuls of ears liquid storage balls of 500 ~ 1000mL, 24 ~ 64 mouthfuls of ears polishing heads, its condition is that the consumption of packing material in silicagel column is 25 times of quality of sample l-arctigenin extract.
By step (4) the silicagel column of gained by sherwood oil, mass concentration, be that 20% acetone, mass concentration are 40% acetone soln wash-out successively, the flow velocity of wash-out is 80mL/min, collects 40% acetone elutriant.
By elutriant through N-1000D Rotary Evaporators temperature be under 45 ℃, the pressure condition that is 0.07MPa through evaporated under reduced pressure to constant weight, obtain l-arctigenin extract medicinal extract; In l-arctigenin extract medicinal extract, by the solid-to-liquid ratio of 1 g:30 mL, add dehydrated alcohol-sherwood oil-acetone to carry out recrystallization, standing 60 hours, be put in ventilating kitchen, obtain l-arctigenin prism-shaped crystal.
Wherein: dehydrated alcohol-sherwood oil-acetone three's volume ratio (mL/ mL) is 2:1:0.5.
This l-arctigenin is through high effective liquid chromatography for measuring, content 99.7%.
Above-mentioned
embodimentthe l-arctigenin making in 1 ~ 6 can be applicable to that in the bulk drug as antitumor and treatment diabetes, (treatment diabetes relevant experimental data has been published in Diabetologia magazine, and specifying information is as follows.S.-L.?Huang?,R.-T.?Yu?,J.?Gong,Y.?Feng?,?Y.-L.?Dai?,F.?Hu?,?Y.-H.?Hu?,?Y.-D.?Tao?,Y.?Leng.Arctigenin,?a?natural?compound,?activates?AMP-activated?protein?kinase?via?inhibition?of?mitochondria?complex?I?and?ameliorates?metabolic?disorders?in?ob/ob?mice.?Diabetologia?(2012)?55:1469–1481.DOI?10.1007/s00125-011-2366-3?（IF?6.814））。
Claims (8)
1. from Great Burdock Achene, prepare fast a method for l-arctigenin, comprise the following steps:
(1) the Great Burdock Achene of pulverizing is extracted 1 ~ 3 time by the solid-liquid mass ratio of 1:5 ~ 20 with tap water at 20 ~ 55 ℃, each 1 ~ 3 hour, after filtering, abandon the aqueous solution, drain, obtain Great Burdock Achene slag;
(2) in described Great Burdock Achene slag, adding mass concentration is 50 ~ 98% alcohol, by the solid-liquid mass ratio of 1:5 ~ 20, extracts 1 ~ 4 time at 75 ~ 85 ℃, each 1 ~ 3 hour, after filtering, merges and obtains extracting solution;
By described extracting solution through evaporated under reduced pressure to constant weight, obtain l-arctigenin extract;
(4) by (3) l-arctigenin extract dry method loading 100 ~ 300 order silicagel columns of gained of described step;
By described step (4) the silicagel column of gained by sherwood oil, mass concentration, be that 20% acetone, mass concentration are 40% acetone soln wash-out successively, collect 40% acetone elutriant;
By described elutriant through evaporated under reduced pressure to constant weight, obtain l-arctigenin extract medicinal extract; In described l-arctigenin extract medicinal extract, by the solid-to-liquid ratio of 1 g:10 mL ~ 50 mL, add dehydrated alcohol-sherwood oil-acetone to carry out recrystallization, standing 2 ~ 96 hours, be put in ventilating kitchen, obtain l-arctigenin prism-shaped crystal.
2. a kind of method of preparing fast l-arctigenin from Great Burdock Achene as claimed in claim 1, is characterized in that: the Great Burdock Achene of described step in (1) refers to that granularity 10 ~ 100 objects are dried Great Burdock Achene.
3. a kind of method of preparing fast l-arctigenin from Great Burdock Achene as claimed in claim 1, is characterized in that: described step (3) in the condition of evaporated under reduced pressure refer to that temperature is that 40 ~ 80 ℃, pressure are 0.05 ~ 0.08MPa.
4. a kind of method of preparing fast l-arctigenin from Great Burdock Achene as claimed in claim 1, is characterized in that: described step (4) in the condition of dry method loading be that the consumption of packing material in silicagel column is 4 ~ 30 times of quality of sample l-arctigenin extract.
5. a kind of method of preparing fast l-arctigenin from Great Burdock Achene as claimed in claim 1, is characterized in that: the described step (5) flow velocity of middle wash-out is 30 ~ 200mL/min.
6. a kind of method of preparing fast l-arctigenin from Great Burdock Achene as claimed in claim 1, is characterized in that: described step (6) in the condition of evaporated under reduced pressure refer to that temperature is that 40 ~ 60 ℃, pressure are 0.05 ~ 0.08MPa.
7. a kind of method of preparing fast l-arctigenin from Great Burdock Achene as claimed in claim 1, is characterized in that: described step (6) middle dehydrated alcohol-sherwood oil-acetone three's volume ratio is 1 ~ 3:0 ~ 2:0 ~ 1.
8. the application of the l-arctigenin that a kind of method of preparing fast l-arctigenin from Great Burdock Achene as claimed in claim 1 makes in the bulk drug as antitumor and treatment diabetes.
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| CN201310447928.XA CN103524463A (en) | 2013-09-27 | 2013-09-27 | Method for rapidly preparing great burdock achene aglycone from great burdock achene |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105503785A (en) * | 2014-09-26 | 2016-04-20 | 山东新时代药业有限公司 | Industrial scale preparation method for high-purity arctigenin |
| CN106491682A (en) * | 2016-12-23 | 2017-03-15 | 庆阳敦博科技发展有限公司 | A kind of concocting method of Chinese medicine great burdock achene |
| CN109053829A (en) * | 2018-08-08 | 2018-12-21 | 安徽省美极调味食品有限公司 | A kind of technique of decompression method separation and Extraction arctiin from great burdock achene |
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| CN101736050A (en) * | 2009-12-08 | 2010-06-16 | 辽宁中医药大学 | Preparation method of arctigenin |
| CN103156842A (en) * | 2013-03-08 | 2013-06-19 | 南开大学 | Novel application of Arctigenin in preparation of anti-arrhythmia medicine |
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| CN101736050A (en) * | 2009-12-08 | 2010-06-16 | 辽宁中医药大学 | Preparation method of arctigenin |
| CN103156842A (en) * | 2013-03-08 | 2013-06-19 | 南开大学 | Novel application of Arctigenin in preparation of anti-arrhythmia medicine |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105503785A (en) * | 2014-09-26 | 2016-04-20 | 山东新时代药业有限公司 | Industrial scale preparation method for high-purity arctigenin |
| CN105503785B (en) * | 2014-09-26 | 2019-05-10 | 山东新时代药业有限公司 | A kind of method of industrially scalable preparation high-purity arctigenin |
| CN106491682A (en) * | 2016-12-23 | 2017-03-15 | 庆阳敦博科技发展有限公司 | A kind of concocting method of Chinese medicine great burdock achene |
| CN109053829A (en) * | 2018-08-08 | 2018-12-21 | 安徽省美极调味食品有限公司 | A kind of technique of decompression method separation and Extraction arctiin from great burdock achene |
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