CN102516332A - Preparation method of 10-vanilloyl catalpol - Google Patents

Preparation method of 10-vanilloyl catalpol Download PDF

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Publication number
CN102516332A
CN102516332A CN2011104006836A CN201110400683A CN102516332A CN 102516332 A CN102516332 A CN 102516332A CN 2011104006836 A CN2011104006836 A CN 2011104006836A CN 201110400683 A CN201110400683 A CN 201110400683A CN 102516332 A CN102516332 A CN 102516332A
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ethanol
catalpol
silica gel
medicinal material
acyl
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CN102516332B (en
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孙士青
李春艳
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JINAN DONGYUAN BIOMEDICAL TECHNOLOGY CO., LTD.
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JINAN YUTUOJIN MEDICAL TECHNOLOGY Co Ltd
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Abstract

The invention discloses a preparation method of a 10-vanilloyl catalpol. The preparation method of the 10-vanilloyl catalpol comprises the following steps of 1, preparing figwortflower picrorhiza rhizome powder and putting it aside for next use, 2, preparing gauze bags and putting then aside for next use, 3, putting the figwortflower picrorhiza rhizome powder into the gauze bags to obtain drug bags with the figwortflower picrorhiza rhizome powder, 4, putting the drug bags with the figwortflower picrorhiza rhizome powder into an extraction container, carrying out extraction, and merging filtrate to obtain an ethanol extracted liquid of figwortflower picrorhiza rhizome, 5, standing the ethanol extracted liquid of figwortflower picrorhiza rhizome, 6, feeding the ethanol extracted liquid of figwortflower picrorhiza rhizome into a plate-frame-type filter press by a pump and carrying out filter pressing to obtain ethanol filtrate, 7, putting the ethanol filtrate into a distiller and carrying out distillation to obtain ethanol extract, 8, adding the ethanol extract into chromatography silica gel to obtain mixed silica gel powder for next use, 9, adding eluants into chromatography silica gel, 10, adding the mixed silica gel powder obtained by the step 8 into a chromatography column and carrying out immersion, 11, carrying out chromatography elution, 12 preparing eluants of ethyl acetate and ethanol and carrying out treatment to obtain a discolored liquid, and 13, carrying out distillation of the discolored liquid to recover a solvent and to obtain ethanol extract, mixing the ethanol extract and silica gel, and cooling to obtain the precipitated 10-vanilloyl catalpol. The preparation method provided by the invention realizes extraction of 10-vanilloyl catalpol of figwortflower picrorhiza rhizome and improves an extraction rate.

Description

The preparation method of the fragrant pod acyl of 10-Catalpol
Technical field
The present invention relates to Chinese medicine, is a kind of preparation method who in Chinese medicine material, extracts the fragrant pod acyl of 10-Catalpol.
Background technology
The fragrant pod acyl of 10-Catalpol is present in the Chinese medicine material Rhizoma Picrorhizae medicinal material, mainly is present in the phloem fiber cell of Rhizoma Picrorhizae rhizome.Because Rhizoma Picrorhizae rhizome phloem fiber cell flintiness, toughness and degree of compactness are far above the phloem fiber cell of general Chinese medicinal plant rhizome, so the difficulty of in Rhizoma Picrorhizae, extracting the fragrant pod acyl of 10-Catalpol is than higher.The method of in Rhizoma Picrorhizae, extracting the fragrant pod acyl of 10-Catalpol disclosed best, that no hazardous solvent is residual; Can only extract and contain 30% of the fragrant pod acyl of 10-Catalpol total amount in the Rhizoma Picrorhizae medicinal material; Extraction yield is lower; Cause a large amount of wastes of Rhizoma Picrorhizae effective ingredient and Rhizoma Picrorhizae medicinal material, cause using the medicine cost up of the fragrant pod acyl of 10-Catalpol as feedstock production.
Summary of the invention
The objective of the invention is, the preparation method of the fragrant pod acyl of a kind of 10-Catalpol is provided, it extracts the fragrant pod acyl of 10-Catalpol in Rhizoma Picrorhizae, improve extraction yield.
The present invention realizes through following technical scheme for realizing above-mentioned purpose: the preparation method of the fragrant pod acyl of 10-Catalpol comprises the steps:
1. get Rhizoma Picrorhizae pulverizing medicinal materials to 60 order, it is subsequent use to obtain the medicinal material meal;
2. adopt former cotton gauze, process the double-ply bag shape, the capacity of cotton yarn bag is a splendid attire 5kg step medicinal material meal 1., and it is subsequent use to obtain double-deck cotton yarn bag;
3. step medicinal material meal is 1. packed in the step double-deck cotton yarn bag 2., every packed 3kg medicinal material meal of going into double-deck cotton yarn bag sealing, obtains the medicinal material flour bag;
4. the medicinal material meal bag of step in 3. inserted in the extraction vessel; 95% edible ethanol that divides 20 times of amounts that add medicinal material flour bag Chinese medicinal materials meal weight for three times; Add for the first time 8 times of amounts, the second time of medicinal material meal weight and add 6 times of amounts of medicinal material meal weight for the third time respectively; Be heated to boiling reflux and extracted respectively 2 hours, 1.5 hours, 1 hour, filter, merging filtrate obtains ethanol extract;
5. the ethanol extract of step in 4. pumped in the jacketed kettle through liquor pump, feed the circulation of terepthaloyl moietie refrigeration agent in the interlayer and be cooled to 0 ℃-4 ℃, left standstill 20-28 hour;
6. the ethanol extract after step being left standstill in 5. pumps in the plate-and-frame filter press, make ethanol extract under 19-22MPa pressure through the sheet frame filtering layer, obtain clear and bright ethanol filtrating;
7. ethanol filtrating is inserted and adds thermal distillation in the distiller, to distillment be the medicinal extract shape, obtain pure medicinal extract 300L;
8. pure medicinal extract is added the chromatographic silica gel of 1/3 amount of medicinal material meal total amount, stir, be dried to moisturely, be ground into 80 orders and obtain powdery to mix kind silica gel subsequent use with to separate silica gel moisture identical;
9. get 3.5kg100 order-200 order chromatographic silica gel; Add ETHYLE ACETATE and ethanol blended eluent, stir down and get rid of bubble, pour in the chromatography column; ETHYLE ACETATE and alcoholic acid eluent are eluted to repeatedly that bed surface no longer descends, cylinder is closely knit, ETHYLE ACETATE and alcoholic acid volume ratio are 6:1 again;
10. the powdery of step in 8. being mixed kind silica gel slowly adds on the chromatography column and soaked 9-11 hour;
Figure 2011104006836100002DEST_PATH_IMAGE002
carries out the chromatography wash-out: with ETHYLE ACETATE and ethanol blended eluent wash-out; Collect elutriant; Distillating recovering solvent; It is yellow that distillment is, and pick distillment when " extension flag " phenomenon is arranged with sampling rod, is that 50% the fragrant pod acyl of 10-Catalpol is collected starting point; For collecting terminal point, ETHYLE ACETATE and alcoholic acid volume ratio are not 6:1 when distillment has " extension flag " phenomenon;
processes elutriant in the ratio of ETHYLE ACETATE and alcoholic acid volume ratio 6:1; Again with behind the gac ebuillition of heated that adds the fragrant pod acyl of 10-Catalpol 30% amount of collecting in the step
Figure 289220DEST_PATH_IMAGE002
in the elutriant; Keep boiling 28-35 minute; Filter, obtain the liquid that decolours;
Figure 2011104006836100002DEST_PATH_IMAGE006
will decolour the liquid distillating recovering solvent to pure medicinal extract; Admix silica gel again; Repeating step 8., 9., 10.,
Figure 310528DEST_PATH_IMAGE002
described content carries out the secondary chromatography; Obtain elutriant and reclaim solvent, put and promptly separate out the fragrant pod acyl of 10-Catalpol after cold to hypersaturated state.
The circulation of step of the present invention described in 5. is cooled to 3 ℃, and time of repose is 24 hours.The pressure of step described in 6. is 20MPa.
Method of the present invention is in Rhizoma Picrorhizae, to extract the fragrant pod acyl of 10-Catalpol; This method is packed 60 order Rhizoma Picrorhizae medicinal powders in the cotton yarn cloth bag of two bed thickness; Difficult problems such as bumping, sticking pot and the sad filter of extracting solution in heat-processed have been solved; Simultaneously, the size of double-deck cotton yarn cloth bag and explosive load have increased the flow of solvent property between medical material bag, make composition be easy to diffusion; This method also adopts the stand at low temperature precipitation process with Rhizoma Picrorhizae powder ethanol extract, and handles through pressure filter, can remove most of cold alcohol insoluble matter macromolecular substance, has kept the fragrant pod acyl of 10-Catalpol to greatest extent, has improved the separation efficiency of column chromatography; The inventive method has also adopted ETHYLE ACETATE to carry out depickling; Remove ethanol wherein again with 5% sodium hydrogen carbonate solution equal-volume extraction ETHYLE ACETATE then; Be combined into the column chromatography eluent with ethanol again, solved the deficiency that exists in the available technology adopting chloroform-methanol technology.Simultaneously, adopt in the method for the present invention ethanol be solvent and with the fragrant pod acyl of 10-Catalpol equivalent be that 30% gac adds decolouring, thereby can save mass energy, and avoided the fragrant pod acyl of 10-Catalpol because of overheated destructive is not enough, further improved extraction yield.Adopt method of the present invention in Rhizoma Picrorhizae, to extract the fragrant pod acyl of 10-Catalpol, obtain the fragrant pod acyl of 10-Catalpol extraction yield according to [assay] method detection under Rhizoma Picrorhizae item of Pharmacopoeia of the People's Republic of China version in 2010 and can reach 95%, purity reaches 92%.Method of the present invention also is easy to the production of industriallization flow line; Can adopt " extension flag " phenomenon to judge that the fragrant pod acyl of 10-catalpol content surpasses 50%; The content range of judging the fragrant pod acyl of 10-Catalpol aborning fast only needs 2 seconds kinds; Thoroughly having solved the content that prior art detects the fragrant pod acyl of 10-Catalpol aborning needs several hrs, instructs the deficiency of producing though the result accurately can't feed back fast.
Embodiment
The preparation method of the fragrant pod acyl of 10-of the present invention Catalpol prepares according to following step:
1. get Rhizoma Picrorhizae pulverizing medicinal materials to 60 order, it is subsequent use to obtain the medicinal material meal;
2. adopt former cotton gauze, process the double-ply bag shape, the capacity of cotton yarn bag is a splendid attire 5kg step medicinal material meal 1., and it is subsequent use to obtain double-deck cotton yarn bag;
3. step medicinal material meal is 1. packed in the step double-deck cotton yarn bag 2., every packed 3kg medicinal material meal of going into double-deck cotton yarn bag sealing, obtains the medicinal material flour bag;
4. the medicinal material meal bag of step in 3. inserted in the extraction vessel; 95% edible ethanol that divides 20 times of amounts that add medicinal material flour bag Chinese medicinal materials meal weight for three times; Add for the first time 8 times of amounts, the second time of medicinal material meal weight and add 6 times of amounts of medicinal material meal weight for the third time respectively; Be heated to boiling reflux and extracted respectively 2 hours, 1.5 hours, 1 hour, filter, merging filtrate obtains ethanol extract;
5. the ethanol extract of step in 4. pumped in the jacketed kettle through liquor pump, feed the circulation of terepthaloyl moietie refrigeration agent in the interlayer and be cooled to 0 ℃-4 ℃, left standstill 20-28 hour;
6. the ethanol extract after step being left standstill in 5. pumps in the plate-and-frame filter press, make ethanol extract under 19-22MPa pressure through the sheet frame filtering layer, obtain clear and bright ethanol filtrating;
7. ethanol filtrating is inserted and adds thermal distillation in the distiller, to distillment be the medicinal extract shape, obtain pure medicinal extract 300L;
8. pure medicinal extract is added the chromatographic silica gel of 1/3 amount of medicinal material meal total amount, stir, be dried to moisturely, be ground into 80 orders and obtain powdery to mix kind silica gel subsequent use with to separate silica gel moisture identical;
9. get 3.5kg100 order-200 order chromatographic silica gel; Add ETHYLE ACETATE and ethanol blended eluent, stir down and get rid of bubble, pour in the chromatography column; ETHYLE ACETATE and alcoholic acid eluent are eluted to repeatedly that bed surface no longer descends, cylinder is closely knit, ETHYLE ACETATE and alcoholic acid volume ratio are 6:1 again;
10. the powdery of step in 8. being mixed kind silica gel slowly adds on the chromatography column and soaked 9-11 hour;
Figure 187217DEST_PATH_IMAGE002
carries out the chromatography wash-out: with ETHYLE ACETATE and ethanol blended eluent wash-out; Collect elutriant; Distillating recovering solvent; It is yellow that distillment is, and pick distillment when " extension flag " phenomenon is arranged with sampling rod, is that 50% the fragrant pod acyl of 10-Catalpol is collected starting point; For collecting terminal point, ETHYLE ACETATE and alcoholic acid volume ratio are not 6:1 when distillment has " extension flag " phenomenon;
processes elutriant in the ratio of ETHYLE ACETATE and alcoholic acid volume ratio 6:1; Again with behind the gac ebuillition of heated that adds the fragrant pod acyl of 10-Catalpol 30% amount of collecting in the step in the elutriant; Keep boiling 28-35 minute; Filter, obtain the liquid that decolours;
Figure 164029DEST_PATH_IMAGE006
will decolour the liquid distillating recovering solvent to pure medicinal extract; Admix silica gel again; Repeating step 8., 9., 10.,
Figure 895224DEST_PATH_IMAGE002
described content carries out the secondary chromatography; Obtain elutriant and reclaim solvent, put and promptly separate out the fragrant pod acyl of 10-Catalpol after cold to hypersaturated state.
The further scheme of the method for the invention is: the circulation of step described in 5. is cooled to 3 ℃, and time of repose is 24 hours.
The preferred version of the method for the invention is: the pressure of step described in 6. is 20MPa.
The preparation method of the fragrant pod acyl of 10-of the present invention Catalpol, the employing Tibet picrorhiza rhizome is a raw material, its concrete steps are following:
1. get exsiccant Tibet picrorhiza rhizome 150kg, be crushed to 60 orders;
2. adopt former cotton gauze, process the double-ply bag shape, the capacity of cotton yarn bag is a splendid attire 5kg step meal 1., and it is subsequent use to obtain double-deck cotton yarn bag;
3. step medicinal material meal is 1. packed in the step double-deck cotton yarn bag 2., every packed 3kg medicinal material meal of going into double-deck cotton yarn bag sealing, obtains the medicinal material flour bag;
4. the medicinal material flour bag of step in 3. inserted in the extraction vessel; 95% edible ethanol that divides 20 times of amounts that add raw material medicine bag Chinese medicinal materials meal weight for three times; Add for the first time 8 times of amounts, the second time of medicinal material meal weight and add 6 times of amounts of medicinal material meal weight for the third time respectively; Be heated to boiling reflux and extracted respectively 2 hours, 1.5 hours, 1 hour, filter, merging filtrate obtains ethanol extract;
5. the ethanol extract of step in 4. pumped in the jacketed kettle through liquor pump, feed the circulation of terepthaloyl moietie refrigeration agent in the interlayer and be cooled to 3 ℃, left standstill 24 hours;
6. the ethanol extract after step being left standstill in 5. pumps in the plate-and-frame filter press, make ethanol extract under 20MPa pressure through the sheet frame filtering layer, obtain clear and bright ethanol filtrating;
7. ethanol filtrating is inserted and adds thermal distillation in the distiller, to distillment be the medicinal extract shape, obtain pure medicinal extract 300L;
8. get 3000ml alcohol medicinal extract, add 500g silica gel and mix thoroughly, dry to water cut 2% with to separate the silica gel water cut identical, be crushed to 80 orders, obtain pulverizing that to mix kind silica gel subsequent use;
9. get 3.5kg200 order chromatographic silica gel; Add ETHYLE ACETATE and ethanol blended eluent, stir down and get rid of bubble, pour in the chromatography column; ETHYLE ACETATE and alcoholic acid eluent are eluted to repeatedly that bed surface no longer descends, cylinder is closely knit, ETHYLE ACETATE and alcoholic acid volume ratio are 6:1 again;
10. the powdery of step in 8. being mixed kind silica gel slowly adds on the chromatography column and soaked 10 hours;
Figure 950905DEST_PATH_IMAGE002
carries out the chromatography wash-out: with ETHYLE ACETATE and ethanol blended eluent wash-out; Collect elutriant; Distillating recovering solvent; It is yellow that distillment is, and pick distillment when " extension flag " phenomenon is arranged with sampling rod, is that 50% the fragrant pod acyl of 10-Catalpol is collected starting point; For collecting terminal point, ETHYLE ACETATE and alcoholic acid volume ratio are not 6:1 when distillment has " extension flag " phenomenon;
Figure 767551DEST_PATH_IMAGE004
processes elutriant in the ratio of ETHYLE ACETATE and alcoholic acid volume ratio 6:1; Again with behind the gac 40g ebuillition of heated that adds the fragrant pod acyl of 10-Catalpol 30% amount of collecting in the step
Figure 80064DEST_PATH_IMAGE002
in the elutriant; Keep boiling 30 minutes; Filter, obtain the liquid that decolours;
Figure 665766DEST_PATH_IMAGE006
will decolour the liquid distillating recovering solvent to pure medicinal extract; Admix silica gel again; The weight step 8., 9., 10., described content carries out the secondary chromatography; Obtain elutriant and reclaim solvent to hypersaturated state; Put and promptly separate out the fragrant pod acyl of 10-Catalpol 50-60g after cold; The purity of the fragrant pod acyl of 10-Catalpol is 92%, and the extraction yield of the fragrant pod acyl of 10-Catalpol is 95%.
The preparing method's of the fragrant pod acyl of 10-of the present invention Catalpol step Described in " extension flag " be meant that the distillment that the sampling rod head picks reaches 6.5 * 10 11When mooring/80 ℃ viscosity factor value, attached to sampling rod head and the distillment volume that picked greater than 2 times on sampling rod head more than the volume, likeness in form flag shape.

Claims (3)

1.10-the preparation method of fragrant pod acyl Catalpol is characterized in that: comprise the steps:
1. get Rhizoma Picrorhizae pulverizing medicinal materials to 60 order, it is subsequent use to obtain the medicinal material meal;
2. adopt former cotton gauze, process the double-ply bag shape, the capacity of cotton yarn bag is a splendid attire 5kg step medicinal material meal 1., and it is subsequent use to obtain double-deck cotton yarn bag;
3. step medicinal material meal is 1. packed in the step double-deck cotton yarn bag 2., every packed 3kg medicinal material meal of going into double-deck cotton yarn bag sealing, obtains the medicinal material flour bag;
4. the medicinal material meal bag of step in 3. inserted in the extraction vessel; 95% edible ethanol that divides 20 times of amounts that add medicinal material flour bag Chinese medicinal materials meal weight for three times; Add for the first time 8 times of amounts, the second time of medicinal material meal weight and add 6 times of amounts of medicinal material meal weight for the third time respectively; Be heated to boiling reflux and extracted respectively 2 hours, 1.5 hours, 1 hour, filter, merging filtrate obtains ethanol extract;
5. the ethanol extract of step in 4. pumped in the jacketed kettle through liquor pump, feed the circulation of terepthaloyl moietie refrigeration agent in the interlayer and be cooled to 0 ℃-4 ℃, left standstill 20-28 hour;
6. the ethanol extract after step being left standstill in 5. pumps in the plate-and-frame filter press, make ethanol extract under 19-22MPa pressure through the sheet frame filtering layer, obtain clear and bright ethanol filtrating;
7. ethanol filtrating is inserted and adds thermal distillation in the distiller, to distillment be the medicinal extract shape, obtain pure medicinal extract 300L;
8. pure medicinal extract is added the chromatographic silica gel of 1/3 amount of medicinal material meal total amount, stir, be dried to moisturely, be ground into 80 orders and obtain powdery to mix kind silica gel subsequent use with to separate silica gel moisture identical;
9. get 3.5kg100 order-200 order chromatographic silica gel; Add ETHYLE ACETATE and ethanol blended eluent, stir down and get rid of bubble, pour in the chromatography column; ETHYLE ACETATE and alcoholic acid eluent are eluted to repeatedly that bed surface no longer descends, cylinder is closely knit, ETHYLE ACETATE and alcoholic acid volume ratio are 6:1 again;
10. the powdery of step in 8. being mixed kind silica gel slowly adds on the chromatography column and soaked 9-11 hour;
Figure 2011104006836100001DEST_PATH_IMAGE002
carries out the chromatography wash-out: with ETHYLE ACETATE and ethanol blended eluent wash-out; Collect elutriant; Distillating recovering solvent; It is yellow that distillment is, and pick distillment when " extension flag " phenomenon is arranged with sampling rod, is that 50% the fragrant pod acyl of 10-Catalpol is collected starting point; For collecting terminal point, ETHYLE ACETATE and alcoholic acid volume ratio are not 6:1 when distillment has " extension flag " phenomenon;
processes elutriant in the ratio of ETHYLE ACETATE and alcoholic acid volume ratio 6:1; Again with behind the gac ebuillition of heated that adds the fragrant pod acyl of 10-Catalpol 30% amount of collecting in the step
Figure 777813DEST_PATH_IMAGE002
in the elutriant; Keep boiling 28-35 minute; Filter, obtain the liquid that decolours;
Figure 2011104006836100001DEST_PATH_IMAGE006
will decolour the liquid distillating recovering solvent to pure medicinal extract; Admix silica gel again; Repeating step 8., 9., 10.,
Figure 819587DEST_PATH_IMAGE002
described content carries out the secondary chromatography; Obtain elutriant and reclaim solvent, put and promptly separate out the fragrant pod acyl of 10-Catalpol after cold to hypersaturated state.
2. the preparation method of the fragrant pod acyl of 10-according to claim 1 Catalpol is characterized in that: the circulation of step described in 5. is cooled to 3 ℃, and time of repose is 24 hours.
3. the preparation method of the fragrant pod acyl of 10-according to claim 1 Catalpol is characterized in that: the pressure of step described in 6. is 20MPa.
CN201110400683.6A 2011-12-06 2011-12-06 Preparation method of 10-vanilloyl catalpol Active CN102516332B (en)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102920831A (en) * 2012-11-20 2013-02-13 济南康众医药科技开发有限公司 Preparation method of rhizoma picrorhizae total saponins
CN104892699A (en) * 2015-05-05 2015-09-09 济南东源生物医药技术有限公司 Method for preparing high-purity 6'-O-trans-cinnamylcatalpol
CN105017355A (en) * 2015-07-21 2015-11-04 济南同生生物医药科技有限公司 6'-O-trans-cinnamoylcatalpol normal phase pressured column chromatography preparation method
CN105111257A (en) * 2015-09-19 2015-12-02 济南同生生物医药科技有限公司 Technological method for simultaneously preparing androsin, picroside II and picroside I
CN105198941A (en) * 2015-09-21 2015-12-30 济南同生生物医药科技有限公司 Aluminum oxide pressurized column chromatography preparation of 6'-O-trans cinnamyl catalpa alcohol

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
尹立子 等: "西藏胡黄连化学成分的分离和鉴定", 《高等学校化学学报》 *
胡红侠 等: "西藏胡黄连的化学成分研究", 《中国医药工业杂志》 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102920831A (en) * 2012-11-20 2013-02-13 济南康众医药科技开发有限公司 Preparation method of rhizoma picrorhizae total saponins
CN102920831B (en) * 2012-11-20 2014-07-23 济南康众医药科技开发有限公司 Preparation method of rhizoma picrorhizae total saponins
CN104892699A (en) * 2015-05-05 2015-09-09 济南东源生物医药技术有限公司 Method for preparing high-purity 6'-O-trans-cinnamylcatalpol
CN105017355A (en) * 2015-07-21 2015-11-04 济南同生生物医药科技有限公司 6'-O-trans-cinnamoylcatalpol normal phase pressured column chromatography preparation method
CN105017355B (en) * 2015-07-21 2017-10-24 济南同生生物医药科技有限公司 The positive pressurized column chromatography preparation method of the trans cinnamyl Catalpols of 6 ' O
CN105111257A (en) * 2015-09-19 2015-12-02 济南同生生物医药科技有限公司 Technological method for simultaneously preparing androsin, picroside II and picroside I
CN105111257B (en) * 2015-09-19 2017-10-10 济南同生生物医药科技有限公司 It is a kind of to prepare glucose acetyl vanilla glycosides, the process of 10 fragrant pod acyl Catalpols and the trans cinnamyl Catalpols of 6 ' O simultaneously
CN105198941A (en) * 2015-09-21 2015-12-30 济南同生生物医药科技有限公司 Aluminum oxide pressurized column chromatography preparation of 6'-O-trans cinnamyl catalpa alcohol

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