CN100425620C - Technology of extracting adenosin phosphoric acid from date - Google Patents

Technology of extracting adenosin phosphoric acid from date Download PDF

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CN100425620C
CN100425620C CNB2006101021443A CN200610102144A CN100425620C CN 100425620 C CN100425620 C CN 100425620C CN B2006101021443 A CNB2006101021443 A CN B2006101021443A CN 200610102144 A CN200610102144 A CN 200610102144A CN 100425620 C CN100425620 C CN 100425620C
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jujube
cyclic monophosphate
jujube juice
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extraction
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CN1948329A (en
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常月梅
杜俊杰
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Abstract

The present invention relates to a technological process for extracting cyclophosphoadenosine from jujube. Said technological process includes the following steps: breaking, soaking, filtering soaking liquor, using ultrasonic technique to extract filter residue, combining extracts to obtain clear jujube juice; making the clear jujube juice be passed through ion exchange column, then making the eluent be again passed through ion exchange column, making the obtained secondary eluent be passed through chromatographic column, collecting solution containing cyclophosphoadenosine concentrating and crystallizing in ethyl alcohol so as to obtain high-purity cyclophosphoadenosine.

Description

A kind of technology of from jujube, extracting cyclic monophosphate
Technical field
The present invention relates to the effective ingredients in plant extraction process, specifically is a kind of technology of extracting cyclic monophosphate from jujube.
Background technology
Date is the mature fruit of Rhamnaceae (Rhamnacene) jujube jujube tree, originates in China.Traditional Chinese medical theory and modern study show that date has the effect of invigorating the spleen and replenishing QI, nourishing blood to tranquillize the mind.Chinese date nutrient is very abundant, except that containing a large amount of sugar, also contains medicinal ingredientss such as cyclic monophosphate and jujube flavones essence, and wherein cyclic monophosphate is the highest in the content in the known plants.Cyclic monophosphate (cAMP) is intracellular second messenger, depend on the protein kinase of cAMP by activation, various adjusting information are taken to specific target site in the cell, the important physical effects such as activity, genetic expression, cell fission and differentiation of performance regulatory enzyme can be anticancer and treatment cardiovascular disorder etc.Current molecular biology further investigation shows, as protein kinase activator, by amplifying the effect of functions of hormones signal and control of heredity information, cyclic monophosphate can be at diastole unstriated muscle, vasodilation, improve liver function, activator and the curative effect of disease of myocardial infarction, coronary heart disease, cardiogenic shock, psoriasis etc. is demonstrated significant effect, so it demonstrates great application prospect in fields such as medical treatment and healthcare products.
At present cyclic monophosphate mainly obtains by chemical synthesis, and there are problems such as the high and security of cost is low in the cyclic monophosphate that chemical synthesis is produced, and the extraction cyclic monophosphate can this type of problem of fine solution from the natural phant date.Though compare other plant, date contains more cyclic monophosphate, and from wherein cyclic monophosphate being extracted the thing that remains a difficulty, this mainly is because the cyclic monophosphate content denier (content is about 5/10000ths) in the date.There have been some to occur about reports such as AG mensuration and small-scale chromatography extractions, but because factor existence such as technical requirements harshness and cost height, its large-scale industrial production still is difficult to carry out.
Technology from jujube extraction purity ring adenosine phosphate all is to have adopted solvent lixiviate and column chromatography technology basically at present.K Hanabusa etc. has reported the method for extracting cAMP from Chinese date, is with 5 ℃ of water-soluble stirring 1h of jujube powder, homogenizing, centrifugal, precipitate water-solublely, centrifugal, supernatant liquor merges back last twice Dowex 1x4 type formic acid salt plug continuously, 0.05N formic acid wash-out, on the elutriant behind the alumina column, last again Dowex 1x4 type formate-type post, obtained component freeze-drying, obtain purity at last and be 34% cAMP, can get high purity cyclic monophosphate product behind the TLC thin layer purifying.Li Mingrun etc. apply for a patent report in " technology of extracting cyclic monophosphate (cAMP) from jujube " in China, by soaking, and homogenate, centrifugal, concentrate and three anion exchange chromatographies and once oxidation aluminium column chromatography method, obtain lyophilized powder.It seems that comprehensively aforesaid method is to have the advantage that cost is low and have no side effect than chemical synthesis, but still some shortcomings are arranged: the firstth, to the break process inappropriate technology of jujube raw material.Extracting a kind of active substance need carry out fully broken to raw material, but owing to contain a large amount of sugars in the jujube, gelatinization especially easily after the suction, if before most of sugar extracts raw material crushing is not too carefully got juice such as process meanses such as adopting homogenizing, homogenate, will increase the weight of to extract the muddiness of juice, make water get the juice complex process, the industrialization difficulty, therefore select water to make digestion agent, the jujube raw material can not be broken too thin, a suitable degree of crushing must be arranged, could guarantee not only to have extracted cyclic monophosphate effectively but also can not cause follow-up exchange column to stop up; If require jujube is carried out the stoning fragmentation, this point also can make the industrialization difficulty strengthen in addition.The second, the jujube raw material too thin to fragmentation, water when cyclic monophosphate is extracted, also can extract too much impurity (as sugar) etc. as digestion agent, causes follow-up column chromatography and purification process numerous and diverse, and efficient is not high, and product purity is low.If flooding agent or jujube raw material crushing treatment process are suitably improved, then can improve the quality of product greatly.The 3rd, harsh in the existing processes to temperature requirement, require about 4 ℃ as service temperature, this can increase the refrigeration investment of extraction equipment.The 4th, in chromatography, all used alumina column, and elutriant selects to contain strong acid liquid.Because aluminum oxide is easy and particularly strong acid (example hydrochloric acid) reaction of acid, sneaks in the elutriant, can increase the difficulty of later separation purifying equally.The 5th, freeze-drier is expensive big, the production cost height.The 6th, do not carry out the comprehensive utilization of product in the production, to the human body beneficial be that the jujube essence of feature does not have extraction and application with the jujube flavones, cause product single, the production cost height.Therefore from aspects such as extraction efficiency and quality and suitability for industrialized production, existing processes all is badly in need of improving energetically raising.
Summary of the invention
The present invention provides a kind of extraction efficiency height, purity height, simple, the suitable industrialized technology of extracting cyclic monophosphate from jujube of production cost low energy of processing requirement in order to solve problems such as existing cyclic monophosphate extraction process industrialization difficulty is big, leaching process is numerous and diverse, efficient is not high, product purity is low.
The present invention adopts following technical scheme to realize: a kind of technology of from jujube, extracting cyclic monophosphate, and concrete steps are as follows:
(1), get the red date fragmentation, add extraction solvent and soak and extract at least once, filter to such an extent that soak and extract jujube juice and filter residue, filter residue making beating adds distilled water and carries out supersound extraction, filter supersound extraction jujube juice and jujube slag, merge all and extract jujube juice, concentrate, leave standstill clarification jujube juice;
(2), clarification jujube juice is by anion-exchange column, the aqueous formic acid wash-out is collected to such an extent that contain the solution of cyclic monophosphate;
(3), the solution that contains cyclic monophosphate is by chromatography column, adds the elutriant wash-out, collects the solution that contains cyclic monophosphate, concentrates the back and adds dehydrated alcohol, leaves standstill, crystallization is filtered, pulverize after the vacuum-drying high purity cyclic monophosphate powder.
Red date is broken into the 2-10 order in the described step (1), and the weight that adds extraction solvent is 1-3 times of red date weight, soaks number of times 3-6 time, and soak extraction time is 4-8 hour at every turn, and it is 6-21 ℃ that temperature is extracted in immersion.
Extraction solvent in the described step (1) is distilled water or alcohol solution, and alcohol solution is a methanol aqueous solution, perhaps aqueous ethanolic solution, and its pure content is 0.5-10% (wt/wt).
The supersound extraction time is 10-40min in the described step (1), and the weight that adds distilled water is 1-2 times of filter residue weight.
In the described step (1) united extraction jujube juice being concentrated to soluble solid content is 6-15%.
The solution that contains cyclic monophosphate in the described step (2) can use the ammonia soln of 2-10% (wt/wt) to regulate PH to neutral, by anion-exchange column, uses the formic acid solution wash-out once more, must contain the solution of cyclic monophosphate once more.Wash-out is 3-10% (wt/wt) with aqueous formic acid concentration.
Chromatography column in the described step (3) is a silica gel type, perhaps macroporous resin type, perhaps polymeric amide type; The vacuum-drying temperature is 25-85 ℃; Elutriant in the described step (3) is a distilled water, or ethanol content is the aqueous ethanolic solution of 0.1-5% (wt/wt).
The natural cAMP sample and the cAMP standard model that adopt liquid chromatograph that this technology is extracted are measured, and measurement result is seen accompanying drawing 1,2 and table 1,2:
Table 1cAMP standard model measurement result data sheet
Accumulative total peak number: 3 cumulative area summations: 2820265 cumulative area per-cent summations: 100.000%
Sequence number Retention time Peak area Analytical results (%)
1 1.735 3542 0.1256
2 2.082 3527 0.1251
3 3.745 2813196 99.7494
This technology of table 2 extract the measurement result data sheet of natural cAMP sample
Accumulative total peak number: 7 cumulative area summations: 2137960 cumulative area per-cent summations: 100.000%
Sequence number Retention time Peak area Analytical results (%)
1 0.802 103 0.0048
2 1.607 365 0.0171
3 1.722 605 0.0283
4 2.150 1685 0.0788
5 2.540 4224 0.1976
6 3.358 951 0.0445
7 3.743 2130026 99.6289
In addition, in the step 2 by the jujube juice behind the exchange column can concentrate concentrated jujube juice; Extract the jujube slag that produces after cyclic monophosphate filters in the step 1 and can extract the jujube essence, extract the jujube essence and can adopt following steps:
Adding ethanol content in the jujube slag is the aqueous ethanolic solution of 60-95% (wt/wt), its add-on is 1-3 a times of jujube filter residue weight, reflux 1-2 hour, filter to get filtrate, filter residue repeats as preceding heating and refluxing extraction once again, merge front and back extracted twice liquid, be concentrated to the 5-30% (wt/wt) of stoste, collect the medicinal extract that is rich in the jujube flavones and get the jujube essence.
The present invention compares with existing cyclic monophosphate extraction process has following advantage:
1, extraction efficiency height, cyclic monophosphate content is greater than 90% (wt/wt), and it is residual not contain any chemical catalyst, and stable in properties is pure natural, free of contamination quality products;
2, service temperature gentleness, technology is simple, and this technology need not harsh low temperature (as about 4 ℃) lixiviate;
3, the present invention adopts the suitable broken distilled water of jujube raw material or alcohol solution to soak to extract, and need not making beating before the most of jujube juice that contains the cyclic monophosphate composition extracts, and has improved the selectivity of extracting widely and has helped slag liquid and separated;
4, the present invention adopts the supersound extraction means, and the extraction efficiency that remains in cyclic monophosphate in the jujube slag is improved;
5, later stage chromatography of the present invention uses non-oxide aluminium post, has reduced because post dissociates and has waited the new pollution that brings, and the while has further been adopted the solvent crystallization processing, and this all helps improving cyclic monophosphate purity;
6, at drying stage, the present invention adopts vacuum-drying, and is lower than lyophilize cost, helps suitability for industrialized production;
7, this technology by-product jujube essence and concentrated jujube juice had both carried out the deep processing comprehensive utilization, had improved productivity effect, had reduced the exhaust emission in producing again.
Description of drawings
Fig. 1 is the liquid chromatogram of standard substance cAMP;
Fig. 2 is the liquid chromatogram of the natural cAMP sample of employing technology extraction of the present invention.
Embodiment
Embodiment 1:
After the selected cleaning removal of impurities of red date 1000g, go jujube nuclear to be broken into 2 orders, add 3000g distilled water, 16 ℃ are soaked extraction 6 hours, press filtration must be soaked and be extracted jujube juice, and the distilled water that filter residue adds identical weight again repeats to soak extraction, carries out altogether 3 times, last gained jujube slag making beating back adds 1 times of distilled water supersound extraction 30min, filter supersound extraction jujube juice; Merging all extraction jujube juice and being concentrated to soluble solid content is 8%, leaves standstill clarification and must clarify jujube juice 6300ml after 1 hour.
Clarification jujube juice is by anion-exchange column, cross behind the post jujube juice concentrate concentrated jujube juice; Ion exchange column is with 8% (wt/wt) aqueous formic acid wash-out, and time elutriant 2400ml that wins passes through this ion exchange column after being adjusted to neutrality with 5% ammoniacal liquor again, as above method again wash-out get elute soln 1100ml, this liquid is used the distilled water wash-out by silicagel column, obtains containing cyclic monophosphate solution 500ml, concentrate the back and add dehydrated alcohol, leave standstill, crystallization is filtered, pulverize after 55 ℃ of 0.1pa vacuum-dryings high-purity cyclic monophosphate powder 55mg, content 93%.
Adding ethanol content in the 500g jujube filter residue is the aqueous ethanolic solution 1000g of 80% (wt/wt), reflux 1 hour, filter to get filtrate, filter residue is preceding for another example to repeat heating and refluxing extraction once, before and after merging extracted twice liquid altogether 1500g, be concentrated to 10% (wt/wt) of stoste, collect medicinal extract, get by-product jujube essence.
Embodiment 2:
After the selected cleaning removal of impurities of red date 1000g, go jujube nuclear to be broken into 10 orders, adding the 2000g ethanol content is 5% (wt/wt) aqueous ethanolic solution, 6 ℃ are soaked extraction 6 hours, press filtration must be soaked and be extracted jujube juice, and the alcohol solution that filter residue adds same concentrations again repeats to soak extraction, carries out altogether 5 times, last gained jujube slag making beating back adds 1 times of distilled water supersound extraction 30min, filter supersound extraction jujube juice; Merging all extraction jujube juice and being concentrated to soluble solid content is 6%, leaves standstill clarification and must clarify jujube juice 6000ml after 1 hour.
Clarification jujube juice is by anion-exchange column, cross behind the post jujube juice concentrate concentrated jujube juice; Ion exchange column is with 8% (wt/wt) aqueous formic acid wash-out, and time elutriant 2200ml that wins passes through this ion exchange column after being adjusted to neutrality with 5% ammoniacal liquor again, as above method again wash-out get elute soln 1000ml, this liquid is 5% aqueous ethanolic solution wash-out by silicagel column with ethanol content, obtains containing cyclic monophosphate solution 500ml, concentrate the back and add dehydrated alcohol, leave standstill, crystallization is filtered, pulverize after 25 ℃ of 0.1pa vacuum-dryings high-purity cyclic monophosphate powder 50mg, content 92%.
Adding ethanol content in the 500g jujube filter residue is the aqueous ethanolic solution 1000g of 60% (wt/wt), reflux 1 hour, filter to get filtrate, filter residue is preceding for another example to repeat heating and refluxing extraction once, before and after merging extracted twice liquid altogether 1600g, be concentrated to 5% (wt/wt) of stoste, collect medicinal extract, get the jujube essence.
Embodiment 3:
After the selected cleaning removal of impurities of red date 1000g, do not go jujube nuclear to be broken into 2 orders, adding the 1000g ethanol content is 5% (wt/wt) aqueous ethanolic solution, 15 ℃ are soaked extraction 4 hours, suction filtration must soak and extract jujube juice, and filter residue as above repeats to soak and extracts, and carries out altogether 3 times, last gained jujube slag making beating back adds 1.5 times of distilled water supersound extraction 40min, filter supersound extraction jujube juice; Merging all extraction jujube juice and being concentrated to soluble solid content is 12%, leaves standstill clarification and must clarify jujube juice 2800ml after 1 hour.
Clarification jujube juice is by anion-exchange column, cross behind the post jujube juice concentrate concentrated jujube juice; Ion exchange column is with 5% (wt/wt) aqueous formic acid wash-out, and time elutriant 2100ml that wins passes through this ion exchange column after being adjusted to neutrality with 10% ammoniacal liquor again, as above method again wash-out get elute soln 1000ml, this liquid is 0.1% aqueous ethanolic solution wash-out by polyamide column with ethanol content, obtains containing cyclic monophosphate solution 500ml, concentrate the back and add dehydrated alcohol, leave standstill, crystallization is filtered, pulverize after 45 ℃ of 0.1pa vacuum-dryings high-purity cyclic monophosphate powder 20mg, content 95%.
Adding ethanol content in the 500g jujube filter residue is the aqueous ethanolic solution 1500g of 95% (wt/wt), reflux 2 hours, filter to get filtrate, filter residue is preceding for another example to repeat heating and refluxing extraction once, before and after merging extracted twice liquid altogether 2300g, be concentrated to 10% (wt/wt) of stoste, collect medicinal extract and get jujube flavones essence.
Embodiment 4:
After the selected cleaning removal of impurities of red date 1000g, stoning is broken into 8 orders, adding the 1500g ethanol content is 0.5% (wt/wt) aqueous ethanolic solution, 21 ℃ are soaked extraction 8 hours, seepage is filtered to such an extent that soak extraction jujube juice, and filter residue as above repeats to soak and extracts, and carries out altogether 4 times, last gained jujube slag making beating back adds 2 times of distilled water supersound extraction 40min, filter supersound extraction jujube juice; Merging all extraction jujube juice and being concentrated to soluble solid content is 10%, leaves standstill clarification and must clarify jujube juice 5000ml after 1 hour.
Clarification jujube juice is by anion-exchange column, cross behind the post jujube juice concentrate concentrated jujube juice; Ion exchange column is with 10% (wt/wt) aqueous formic acid wash-out, and time elutriant 2100ml that wins passes through this ion exchange column after being adjusted to neutrality with 2% ammoniacal liquor again, as above method again wash-out get elute soln 1100ml, this liquid is 0.5% aqueous ethanolic solution wash-out by macroporous resin column with ethanol content, obtains containing cyclic monophosphate solution 600ml, concentrate the back and add dehydrated alcohol, leave standstill, crystallization is filtered, pulverize after 85 ℃ of 0.1pa vacuum-dryings high-purity cyclic monophosphate powder 30mg, content 95%.
Adding ethanol content in the 500g jujube filter residue is the aqueous ethanolic solution 500g of 75% (wt/wt), reflux 1.5 hours, filter to get filtrate, filter residue is preceding for another example to repeat heating and refluxing extraction once, before and after merging extracted twice liquid altogether 700g, be concentrated to 15% (wt/wt) of stoste, collect the jujube essence that medicinal extract must contain the jujube flavones.
Embodiment 5:
After the selected cleaning removal of impurities of red date 1000g, have jujube nuclear and be broken into 5 orders, adding the 1500g ethanol content is 10% (wt/wt) aqueous ethanolic solution, 15 ℃ are soaked extraction 5 hours, filter to such an extent that soak extraction jujube juice, filter residue as above repeats to soak and extracts, and carries out altogether 5 times, last gained jujube slag making beating back adds 1.5 times of distilled water supersound extraction 10min, filter supersound extraction jujube juice; Merging all extraction jujube juice and being concentrated to soluble solid content is 11%, leaves standstill clarification and must clarify jujube juice 5000ml after 1 hour.
Clarification jujube juice is by anion-exchange column, cross behind the post jujube juice concentrate concentrated jujube juice; Ion exchange column is with 10% (wt/wt) aqueous formic acid wash-out, and time elutriant 2000ml that wins passes through this ion exchange column after being adjusted to neutrality with 5% ammoniacal liquor again, as above method again wash-out get elute soln 900ml, this liquid is 1% aqueous ethanolic solution wash-out by polyamide column with ethanol content, obtains containing cyclic monophosphate solution 500ml, concentrate the back and add dehydrated alcohol, leave standstill, crystallization is filtered, pulverize after 65 ℃ of 0.1pa vacuum-dryings high-purity cyclic monophosphate powder 30mg, content 97%.
Adding ethanol content in the 500g jujube filter residue is the aqueous ethanolic solution 1000g of 95% (wt/wt), reflux 1.5 hours, filter to get filtrate, filter residue is preceding for another example to repeat heating and refluxing extraction once, before and after merging extracted twice liquid altogether 1500g, be concentrated to 30% (wt/wt) of stoste, collect medicinal extract and get jujube flavones essence.
Embodiment 6:
After the selected cleaning removal of impurities of red date 1000g, be broken into 2 orders after the stoning, adding the 1000g methanol content is 1% (wt/wt) methanol aqueous solution, 20 ℃ are soaked extraction 6 hours, suction filtration must soak and extract jujube juice, and filter residue as above repeats to soak and extracts, and carries out altogether 6 times, last gained jujube slag making beating back adds 1.5 times of distilled water supersound extraction 20min, filter supersound extraction jujube juice; Merging all extraction jujube juice and being concentrated to soluble solid content is 15%, leaves standstill clarification and must clarify jujube juice 4200ml after 1 hour.
Clarification jujube juice is by anion-exchange column, cross behind the post jujube juice concentrate concentrated jujube juice; Ion exchange column is with 3% (wt/wt) aqueous formic acid wash-out, and time elutriant 2000ml that wins passes through this ion exchange column after being adjusted to neutrality with 5% ammoniacal liquor again, as above method again wash-out get elute soln 1000ml, this liquid is 0.5% aqueous ethanolic solution wash-out by macroporous resin column with ethanol content, obtains containing cyclic monophosphate solution 500ml, concentrate the back and add dehydrated alcohol, leave standstill, crystallization is filtered, pulverize after 45 ℃ of 0.1pa vacuum-dryings high-purity cyclic monophosphate powder 20mg, content 95%.
Adding ethanol content in the 500g jujube filter residue is the aqueous ethanolic solution 750g of 70% (wt/wt), reflux 2 hours, filter to get filtrate, filter residue is preceding for another example to repeat heating and refluxing extraction once, before and after merging extracted twice liquid altogether 900g, be concentrated to stoste 20% (wt/wt), collect the jujube essence that medicinal extract must contain the jujube flavones.

Claims (1)

1, a kind of technology of extracting cyclic monophosphate from jujube is characterized in that concrete steps are as follows:
Get red date and be broken into the 2-10 order; Adding weight is that the 1-3 distilled water or the weight percent doubly of red date weight is the alcohol solution of 0.5-10%, soaks number of times 3-6 time, and soak extraction time is 4-8 hour at every turn, and soaking the extraction temperature is 6-21 ℃; Filter to such an extent that jujube juice and filter residue are extracted in immersion, the filter residue making beating adds distilled water and carries out supersound extraction, and the weight that adds distilled water is 1-2 times of filter residue weight, and the supersound extraction time is 10-40min; Filter supersound extraction jujube juice and jujube slag, merge all and extract jujube juice, concentrate, it is 6-15% that united extraction jujube juice is concentrated to soluble solid content, leave standstill clarification jujube juice; Clarification jujube juice is by anion-exchange column, and aqueous formic acid wash-out, wash-out weight percent are the aqueous formic acid concentration of 3-10%, collects to such an extent that contain the solution of cyclic monophosphate; The solution weight percent that contains cyclic monophosphate is that the ammonia soln of 2-10% is regulated PH to neutral, by anion-exchange column, is the aqueous formic acid wash-out of 3-10% with weight percent once more, must contain the solution of cyclic monophosphate once more; The solution that contains cyclic monophosphate is by chromatography column, and chromatography column is a silica gel type, perhaps macroporous resin type, perhaps polymeric amide type; Add the elutriant wash-out, elutriant is that distilled water or weight percent are the aqueous ethanolic solution of 0.1-5%; Collection contains the solution of cyclic monophosphate, concentrates the back and adds dehydrated alcohol, leaves standstill, and crystallization is filtered; Pulverize after the vacuum-drying high purity cyclic monophosphate powder, the vacuum-drying temperature is 25-85 ℃.
CNB2006101021443A 2006-11-09 2006-11-09 Technology of extracting adenosin phosphoric acid from date Expired - Fee Related CN100425620C (en)

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BRPI0722181A2 (en) * 2007-11-30 2014-04-08 Yu Fen Chi "ANTIMELANCOLIC MEDICINAL PRODUCT PREPARED WITH JUJUBA CAMP-BASED MATERIALS"
RU2452505C2 (en) * 2007-11-30 2012-06-10 Цзогуан ЧЖАН Pharmaceutical compositions with multipurpose receptor reaction mechanism for treating depression
RU2456014C2 (en) * 2007-11-30 2012-07-20 Цзогуан ЧЖАН ANTIMELANCHOLIC MEDICINE PREPARED WITH JUJUBA cAMP MATERIALS
CN101288468B (en) * 2008-05-23 2011-07-20 山西省农业科学院农产品综合利用研究所 Method of sequential extraction of biological activity component from jujube
CN101781348A (en) * 2010-01-18 2010-07-21 刘力 Stable protein kinase activator, preparation method thereof and use
CN102268055B (en) * 2010-06-04 2014-09-24 南京工业大学 Method for separating cyclic adenosine monophosphate
CN102382161A (en) * 2011-08-26 2012-03-21 食品行业生产力促进中心 Method for extracting red date cyclic adenosine monophosphate through ultrasonic composite membrane technology
CN103374053A (en) * 2012-04-12 2013-10-30 新疆农业大学 Method for extracting cyclic adenosine monophosphate from red dates by ultrasonic waves
CN102875625B (en) * 2012-10-29 2015-07-08 北京林业大学 Extraction method of cyclic adenosine monophosphate (cAMP) with antiallergic activity from Chinese date
CN104761606A (en) * 2014-01-07 2015-07-08 中国科学院兰州化学物理研究所 Method for extracting cyclic adenosine monophosphate from jujube
CN105249086B (en) * 2015-11-13 2018-09-07 侯彦国 A kind of preparation process of the red date concentrated juice of high cAMP contents
CN116262772A (en) * 2021-12-14 2023-06-16 无棣县华龙食品有限公司 Method for extracting cAMP in red jujube residues by water-alcohol double phase

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CN1702076A (en) * 2004-01-15 2005-11-30 静海县科学技术委员会 Process for extracting cyclic adenosine monophosphate (cAMP) from Chinese date

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