CN102432577A - Method for separating and purifying epicatechin gallate (ECG) monomer - Google Patents
Method for separating and purifying epicatechin gallate (ECG) monomer Download PDFInfo
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Abstract
The invention discloses a method for separating and purifying an epicatechin gallate (ECG) monomer, which comprises the following steps of: with Yunnan broad-leaf green tea as a raw material, directly extracting by using ethyl acetate; chromatographically adsorbing and eluting a crude extract by two different adsorbent resin columns respectively; collecting desorption fractions containing ECG; concentrating and recovering ethanol in a high-efficiency external-circulation way and concentrating by a reverse osmosis membrane at low temperature; refrigerating and crystallizing 95% ethanol at low temperature; at last, freezing and drying to obtain 98% ECG monomer. The method disclosed by the invention is simple and convenient, short in preparation cycle and low in cost, complies with environment friendliness and safety requirements and is suitable for large-scale industrial production.
Description
Technical field
The present invention relates to a kind of from the green tea raw material separation and purification L-Epicatechin gallate (ECG) monomer methods, belong to food technology field.
Background technology
That catechins has is significantly anti-ageing, anti-cancer mutation, fat-reducing slimming, lowering blood glucose, blood fat and pharmacological functions such as SUV, preventing cardiovascular disease, has been widely used in fields such as food-processing, medicines and health protection and daily-use chemical industry
[1-3]In October, 2006; Food and drug administration (FDA) approval tea-polyphenol is as new prescription drugs; Be used for the Genital warts that part (outside) treatment is caused by the human papillomavirus, this is plant (draft) medicine of FDA according to the first approval listing of medicine amendment regulations in 1962
[4]In 20 years of past; Because the breakthrough of the health care of relevant tea-polyphenol/catechin and pharmacological function research; Not only enlarged green tea share in the international market, and greatly advanced the development of tea leaf extract industry, for good industry and market value basis have been established in the research and development of tealeaves functional component; At present, China has formed the industry size of producing about 5000 tons of tea-polyphenol/catechins per year.The traditional extraction and separation process of catechin bullion mainly comprises ion precipitation method, organic solvent extractionprocess and adsorpting column chromatogram method
[5-7]The most compelling in research of catechin pharmacology nourishing function and the application in industry is NVP-XAA 723 (EGCG), hin (EGC) and L-Epicatechin gallate (ECG), thereby becomes the focus of catechin monomers separation, purifying and clinical application research.But because the complicated component of tealeaves is produced highly purified catechin monomers and is had suitable difficulty from tealeaves.Its technological difficulties are fine separation, and what should prevent also simultaneously that working substance and tealeaves from possessing natural flavour mountaineously is not destroyed and loses, and the course of processing adopts low temperature as far as possible.The relatively more successful both at home and abroad at present technology that is applied to the preparation of EGCG monomer separation mainly comprises technology such as high speed adverse current chromatogram extraction, SMBC separation
[8,9]Both at home and abroad achievement in research shows, ECG anti-oxidant, remove the lipid radical, suppress the human virus infect aspect effect remarkable; Have extremely strong bacteriostatic activity, being expected to develop becomes a kind of natural class antibiotic substance; Also can obviously improve traumatic wounds healing and cicatrization effect; Simultaneously, ECG also has tangible neuroprotective to astrocyte injury
[10 ~ 13]Zhang Ying etc. are with homemade preparation type counter current chromatograph, and (0.2:1:2 v/v) obtains the ECG monomer for solvent systems separation and purification from catechin, and purity reaches 98% with petroleum ether-ethyl acetate-water
[8]Huang Yongdong etc. use B type three band simulated moving bed technologies, with C
18Bonded silica gel is a stationary phase, and (20:80 v/v) is moving phase, and adopting Varicol technology can obtain purity is 91.33% ECG, and the recovery is 91.41% for ethanol and water
[9], but there is C respectively in above-mentioned two kinds of methods
18Shortcomings such as bonded silica gel costs an arm and a leg, and consumption of organic solvent is big, and separation platform (counter current chromatograph, moving-bed) tonburden is little, unsuitable scale is amplified.So far, there is not the industrialization of EGC monomer to prepare the report of aspect as yet both at home and abroad.
Reference is following:
[1] Wang Jing, high Yutang. the epidemiological study [J] that tea-polyphenol is anticancer. tumour, 2011,31 (6): 553-556
[2] Liu Xueming, Liang Shizhong. the health care of tea-polyphenol and pharmacological action and application prospect [J]. food and fermentation industries, 1998,24 (5): 47-51,71
[3] Yokozawa?Tx,?Dong?Ex,?Nakagawa?Tx,?el?al.?In?vitro?and?in?vivo?studies?on?the?radical?scavenging?activity?of?tea?[J].?J?Agric?Food?Chem,?1998,46(6):2143-2150
[4] Huang Fanghua. inquire into Chinese medicine pharmacokinetic and Evaluation Strategy [J] from the first plant amedica that goes through of the U.S.. CHINA JOURNAL OF CHINESE MATERIA MEDICA, 2010,35 (7): 932-935
[5] Huang Siyong, Jin Xianping, Kang Zhenxing does state and puts down. the extraction and purification process of tea-polyphenol research [J] in the tealeaves tankage. Hubei university of TCM journal, 2011,13 (4): 30-32
[6] Zhang Sheng, Liu Zhonghua, Huang Jianan, Liu Ailing, Shi Zhaopeng. adsorption resin method prepares the research [J] of high-purity catechin. tea science, 2002,22 (2): 125-130
[7] Hu Lijuan. the Study on extraction of tea-polyphenol [J] in the green tea. Yunnan Prov Agriculture University's journal, 2011,26 (3): 426-429
[8] Zhang?Ying,?Shi?Zhao-peng,?Nie?Hong-yong,?
et?al.?Preparative?Isolation?and?Purification?of?Catechins?from?Green?Tea?Extract?by?Preparative?Counter-current?Chromatography?[J].?Journal?of?Hunan?Agricultural?University?(Natural?Science),?2003,?29(5):?408-411,?417
[9] Huang Yongdong, Jiang Heyuan, literary composition is used in the river, etc. the comparative studies [J] of traditional SMB, Varicol and Partial-discard technology separation and purification ECG and EGCG. tea science, 2011,31 (3): 201-210
[10]?Guo?Q,?Zhao?BL,?Li?MF,?et?al.?Studies?on?protective?mechanisms?of?four?components?of?green?tea?polyphenols?against?lipid?peroxidation?in?synaptosomes?biochim[J].?Biophys Acta,1996,13?(3):210-222.
[11]?Yoko?Yanagawa,?Yoshimasa?Yamamoto,?Yukihiko?Hara,?Tadakatsu?Shimamura.?A?Combination?Effect?of?Epigallocatechin?Gallate,?a?Major?Compound?of?Green?Tea?Catechins,?with?Antibiotics?on?
Helicobacter?pylori?Growth?In?Vitro?[J].?Current?Microbiology,?2003,?47:244-249.
[12] Renata?T.?Abib,?Andre′?Quincozes-Santos,?Patricia?Nardin,?et?al.?Epicatechin?gallate?increases?glutamate?uptake?and?S100B?secretion?in?C6?cell?lineage?[J].?Mol?Cell?Biochem,?2008,?310:153-158.
[13] Kapoor?M,?Howard?R,?Hall?I?et?al.?Effects?of?epicatechin?gallate?on?wound?healing?and?scar?formation?in?a?full?thickness?incisional?wound?healing?model?in?rats?[J].?Am?J?Pathol,?2004,?165:299-307。
Summary of the invention
Technical problem to be solved by this invention provides separation and purification L-Epicatechin gallate monomer methods from green tea; This method method is easy, the organic solvent of strong toxicity useless, and preparation cycle is short; Cost is low; Meet environmental protection and safe requirement, monomeric extraction yield of L-Epicatechin gallate and product purity are high, suitable scale suitability for industrialized production.
Technical scheme provided by the invention is: a kind of from green tea separation and purification L-Epicatechin gallate monomer methods, comprise the steps:
(1) extract total catechin in the green tea raw material: take by weighing the green tea raw material, add 4 ~ 7 BV ETHYLE ACETATE post-heating, intermittently stir, reclaim ETHYLE ACETATE, concentrated extracting solution, spraying drying obtains total catechin goods then;
(2) separate ester catechin and non-ester catechin: add pure water and dissolve total catechin article configurations to become concentration be the upper prop feed liquid of 3% (w/v); Use the polymeric adsorbent column separating purification; Desorption solvent is an ethanol, collects the alcohol desorption cut, concentrates with efficient outer circulation and reclaims ethanol; With centrifugal, the spraying drying of spissated desorb cut, obtain drying prods;
(3) drying prods in above-mentioned (2) step is used the polymeric adsorbent column separating purification: the adding pure water dissolves said drying prods and is configured to the upper prop feed liquid that concentration is 3% (w/v); Use the polymeric adsorbent column separating purification; Desorption solvent is an ethanol; Collect the alcohol desorption cut, with efficient outer circulation concentrate earlier reclaim ethanol to alcoholic strength 5, centrifugal spray drying after further concentrating with reverse osmosis membrane again;
(4) go on foot the dry product that obtains with 3 ~ 4 times of amounts (w/v), 95% dissolve with ethanol with above-mentioned (3), place, crystallization is filtered, and the product that the crystal lyophilize is obtained is the L-Epicatechin gallate monomer.
Described method, the green tea raw material described in (1) step is a big-leaf species in yunnan green tea, 45 ℃～50 ℃ of the bath temperatures of heating, intermittently 30min stirs 5min; After taking by weighing the green tea raw material, with ethyl acetate extraction three times, each extraction time is 1h; The ETHYLE ACETATE of first, second and third time adding is divided into other 7 BV, 6BV, 4BV, merges all and extracts solution, reclaim under reduced pressure ETHYLE ACETATE; Use the centrifugal spray tower spraying drying after being concentrated into 6～7 mother-in-law U.S. degree, 160 ℃～180 ℃ of control EATs, 70 ℃～80 ℃ of temperature of outgoing airs; Primary cyclone is every to take out spraying dry powder at a distance from 30min, and product is the total catechin goods of large leaf.
Described method is used the polymeric adsorbent column separating purification described in (2), and polymeric adsorbent is D101, one of HP20, polymeric amide (Polyamide) or DM130; Resin demand is: the weight of 40 times of total catechin goods; Last column flow rate: 1.0 BV/h; Desorb: be rich in the non-ester catechin cut with 2BV 25% alcohol desorption earlier, be rich in the ester catechin cut with 2BV 60% alcohol desorption again, the desorb flow velocity is 1.0BV/h.
Described method is used the polymeric adsorbent column separating purification described in (3), and polymeric adsorbent is HP
2One of MGL, NKA-9, AB-8 or S-8, resin demand: 40 times of drying prods weight; Last column flow rate: 3.0 BV/h; Absorption finishes, with the zero(ppm) water of 3BV with same flow velocity drip washing removal of impurities, desorption solvent: 2BV 80% ethanol; Desorb flow velocity: 1.0BV/h.
Catechin in the tealeaves is divided into ester catechin (mainly being EGCG and ECG) and non-ester catechin (mainly being EGC) two big classes; (2) step at first separated ester type/non-ester-type two big acacatechins through adsorbent resin column chromatography in the inventive method, and the resin that in this step, adopts has stronger adsorptive power for gallic acid ester group; (3) step separated ECG through the resin of another type again with EGCG, the resin that the present invention adopts in this step has selection adsorptivity
to ECG and EGCG molecular weight, polarity difference.
Described method; Temperature is controlled at below 45 ℃ when reclaiming ethanol in (2) step and (3) step; Vacuum degree control-below the 0.08Mpa, service temperature was controlled at below 40 ℃ when reverse osmosis membrane concentrated in (3) step, advanced film pressure and was controlled at below 15 Bar.
The present invention has following beneficial effect:
The inventive method coupling ethyl acetate extraction; Two kinds of different adsorbent resin column chromatography fractionation by adsorption, reverse osmosis membranes concentrate and Freeze Drying Technique; Separation and purification L-Epicatechin gallate from big-leaf species in yunnan green tea raw material (ECG purity>98%) monomer; Optimized the separation and purification of products technical process, monomer extraction yield and product purity are high.Effects such as product has antibacterial, and is antiviral, and can significantly improve traumatic wounds healing and cicatrization effect.Also be the important source material of many development of functional food, can be separately or with vitamins, the composite a plurality of fields such as protective foods, makeup and medicine that are applied to of natural plant composition.The inventive method is easy, and preparation cycle is short, and cost is low, meets environmental protection and safe requirement, suitable scale suitability for industrialized production.
Embodiment
Come further to illustrate the present invention through the detailed description of embodiment below, but be not limitation of the present invention, only make example description.
Separation and purification L-Epicatechin gallate (ECG) monomer methods comprises the steps: from big-leaf species in yunnan green tea raw material
1, total catechin in the ethyl acetate extraction green tea raw material:
Take by weighing big-leaf species in yunnan green tea raw material (available from Yunnan Shuan Jiangxian, ECG content is 4.10%), add 7 BV/6BV/4BV ETHYLE ACETATE heating and extracting respectively three times (1h/ time; Keep 45 ℃～50 ℃ of bath temperatures, intermittently 30min stirs 5min), merge all and extract solution; Reclaim under reduced pressure ETHYLE ACETATE, the later stage adds pure water fully replaces and catches up with most ETHYLE ACETATE, uses the centrifugal spray tower spraying drying after being concentrated into 6～7 mother-in-law U.S. degree; 160 ℃～180 ℃ of control EATs; 70 ℃～80 ℃ of temperature of outgoing airs, primary cyclone is every to take out spraying dry powder at a distance from 30min, and product is the total catechin goods of large leaf (it is 21.08% that HPLC detects ECG content).HPLC detects the method for ECG content can reference: Liu Ailing, and Zhang Sheng, Yang Wei is beautiful. green tea lixiviate dynamic studies pre-test [J]. tealeaves communication, 1999, (3): 32-35; What spring thunder, Luo Xueping, Chen Qiang, etc. influence the research [J] of ETHYLE ACETATE to tea-polyphenol and catechin effect of extracting. food research and development, 2007,28 (1): 29-33; Deng Yanli, Gong Zhihua, Hu Yabei, etc. the dose-effect relationship research [J] of ethyl acetate extraction tea-polyphenol. analytical test journal, 2009,28 (10): 1115-1120.
2, through the Type-A adsorbent resin column chromatography separate ester catechin (ECG, EGCG) with non-ester catechin (EGC):
It is the upper prop feed liquid of 3% (w/v) that the total catechin article configurations of adding pure water dissolving large leaf becomes concentration, polymeric adsorbent column separating purification (resin demand: the weight of 40 times of total catechin goods; Last column flow rate: 1.0 BV/h; Desorb: be rich in non-ester catechin cut (mainly containing EGC) with 2BV 25% alcohol desorption earlier, be rich in ester catechin cut (mainly containing ECG and EGCG) with 2BV 60% alcohol desorption again, the desorb flow velocity is 1.0BV/h).Collect 60% alcohol desorption cut, with efficient outer circulation concentrate to reclaim ethanol (temperature is controlled at below 45 ℃, vacuum degree control-below the 0.08Mpa); Being concentrated into behind 6～7 mother-in-law U.S. degree centrifugal spray drying obtains the L-Epicatechin gallate bullion (it is 40.52% that HPLC detects ECG content, and detection method can reference: Gong Yushun, Liu Zhonghua; Huang Jianan; Deng. macroporous adsorbent resin separates the research [J] of tea catechin and theine. Agricultural University Of Hunan's journal, 2005,31 (1): 50-52; Zhang Sheng, Liu Zhonghua, Huang Jianan, etc. adsorption resin method prepares the research [J] of high-purity catechin. tea science, 2002,22 (2): 125-130).
The Type-A polymeric adsorbent is D101, one of HP20, polymeric amide (Polyamide) or DM130.
3, with above-mentioned L-Epicatechin gallate (ECG) bullion through the separation and purification of Type-B adsorbent resin column chromatography:
Add pure water dissolving ECG bullion and be configured to the upper prop feed liquid that concentration is 3% (w/v), polymeric adsorbent column separating purification (resin demand: 40 times of ECG bullion weight; Last column flow rate: 3.0 BV/h; Absorption finishes, with the zero(ppm) water of 3BV with same flow velocity drip washing removal of impurities.Desorption solvent: 2BV 80% ethanol; Desorb flow velocity: 1.0BV/h).Collect 80% alcohol desorption cut, with efficient outer circulation concentrate earlier reclaim ethanol to alcoholic strength 5 (temperature is controlled at below 45 ℃, vacuum degree control-below the 0.08Mpa); Further be concentrated into 6～7 mother-in-law U.S. degree (service temperature is controlled at below 40 ℃, advances film pressure and is controlled at below 15 Bar) with reverse osmosis membrane again, centrifugal spray drying obtains high-content L-Epicatechin gallate (it is 80.25% that HPLC detects ECG content) product; Detection method can reference: Zhang Sheng; Liu Zhonghua, Huang Jianan, etc. high ECG type catechin purifying process research [J]. Agricultural University Of Hunan's journal; 2003,29 (2): 144-146; Sun Yanjuan, Zhu Yuejin, Li Dawei, etc. the applied research [J] of membrane separation technique in the exploitation of mushroom instant tea. Chinese tea processing, 2010, (4): 42-45.
The Type-B polymeric adsorbent is HP
2One of MGL, NKA-9, AB-8 or S-8.
4, with above-mentioned high-content L-Epicatechin gallate (ECG>80%) product with 3 ~ 4 times of amounts (w/v), 95% dissolve with ethanol; Place crystallization treatment for 4 ℃, with the crystal lyophilize, product at first was cooled to-40 ℃ of prefreezings after the filter paper normal pressure filtered; Begin then to vacuumize; Vacuum tightness begins the heating sublimation drying during to 30Pa, and the control product temperature is no more than 20 ℃, and dry duration 12 ~ 16h (concrete operations can reference: Zhu Chuanjiang. freeze drying process principle and relevant device device [J]. and Shandong medicine thing; 2006,25 (8): 503-504; Xu Chenghai, Zhang Shiwei, close Kui it, etc. the lyophilize experiment [J] of several kinds of materials. vacuum and low temperature, 1998,4 (3): 161-164; Shen Shanming. the drying of thermo-sensitivity medicine [J]. pharmaceutical engineering design, 2010,31 (6): 1-4), get pale yellow powder shape solid.
With above-mentioned pale yellow powder shape product, do not have catechin and gallate (ECG) standard substance [available from U.S. Sigma-Aldrich company, C with table
22H
18O
10, M.W. 442.37, numbering: E3893; Purity>=98% (HPLC)] contrast identify and through high-efficient liquid phase chromatogram technique analysis detect (specifically identify, detection method can reference: fourth is average; Li Yanfang, Song Hang, etc. the analytical procedure of catechin monomers is [J] relatively. the Sichuan chemical industry; 2005,8 (4): 38-41; Wu Di, Yang Lizhu, Chou Peihong, etc. the method for separating and analyzing progress [J] of catechin in the tea. Journal of Analytical Science, 2008,24 (4): 468-472; Liu Ting, Yang Hongmei, Guo Qilei, etc. catechin in the high effective liquid chromatography for measuring tea drink [J]. assay laboratory, 2009,28:277-280; Gu Xungang, Cai Jibao, Zhang Zhengzhu; Deng. HPLC-DAD analyzes the method research [J] of black tea catechins and theine. Agricultural University Of Anhui's journal, 2010,37 (1): 5-10); The result shows: pale yellow powder shape solid molecular weight 442, (-) ESI-MS
M/z: 441 [M-H]
-, EGC>=98%, molecular formula is C
22H
18O
10
Claims (8)
1. a separation and purification L-Epicatechin gallate monomer methods from green tea is characterized in that comprising the steps:
(1) extract total catechin in the green tea raw material: take by weighing the green tea raw material, add 4 ~ 7 BV ETHYLE ACETATE post-heating, intermittently stir, reclaim ETHYLE ACETATE, concentrated extracting solution, spraying drying obtains total catechin goods then;
(2) separate ester catechin and non-ester catechin: add pure water and dissolve total catechin article configurations to become concentration be the upper prop feed liquid of 3% (w/v); Use the polymeric adsorbent column separating purification; Desorption solvent is an ethanol, collects the alcohol desorption cut, concentrates with efficient outer circulation and reclaims ethanol; With centrifugal, the spraying drying of spissated desorb cut, obtain drying prods;
(3) drying prods in above-mentioned (2) step is used the polymeric adsorbent column separating purification: the adding pure water dissolves said drying prods and is configured to the upper prop feed liquid that concentration is 3% (w/v); Use the polymeric adsorbent column separating purification; Desorption solvent is an ethanol; Collect the alcohol desorption cut, with efficient outer circulation concentrate earlier reclaim ethanol to alcoholic strength 5, centrifugal spray drying after further concentrating with reverse osmosis membrane again;
(4) go on foot the dry product that obtains with 3 ~ 4 times of amounts (w/v), 95% dissolve with ethanol with above-mentioned (3), place, crystallization is filtered, and the product that the crystal lyophilize is obtained is the L-Epicatechin gallate monomer.
2. according to the described method of claim 1, it is characterized in that: the green tea raw material described in (1) step is a big-leaf species in yunnan green tea, 45 ℃～50 ℃ of the bath temperatures of heating, and intermittently 30min stirs 5min.
3. according to the described method of claim 1, it is characterized in that: (1) step in, take by weighing the green tea raw material after; With ethyl acetate extraction three times, each extraction time is 1h, and the ETHYLE ACETATE of first, second and third time adding is divided into other 7 BV, 6BV, 4BV; Merge all and extract solution, reclaim under reduced pressure ETHYLE ACETATE is used the centrifugal spray tower spraying drying after being concentrated into 6～7 mother-in-law U.S. degree; 160 ℃～180 ℃ of control EATs; 70 ℃～80 ℃ of temperature of outgoing airs, primary cyclone is every to take out spraying dry powder at a distance from 30min, and product is the total catechin goods of large leaf.
4. according to the described method of claim 1, it is characterized in that: use the polymeric adsorbent column separating purification described in (2), resin demand is: the weight of 40 times of total catechin goods; Last column flow rate: 1.0 BV/h; Desorb: be rich in the non-ester catechin cut with 2BV 25% alcohol desorption earlier, be rich in the ester catechin cut with 2BV 60% alcohol desorption again, the desorb flow velocity is 1.0BV/h.
5. according to the described method of claim 4, it is characterized in that: use the polymeric adsorbent column separating purification described in (2), polymeric adsorbent is D101, one of HP20, polymeric amide or DM130.
6. according to the described method of claim 1, it is characterized in that: use polymeric adsorbent column separating purification, resin demand: 40 times of drying prods weight described in (3); Last column flow rate: 3.0 BV/h; Absorption finishes, with the zero(ppm) water of 3BV with same flow velocity drip washing removal of impurities, desorption solvent: 2BV 80% ethanol; Desorb flow velocity: 1.0BV/h.
7. according to the described method of claim 1, it is characterized in that: use the polymeric adsorbent column separating purification described in (3), polymeric adsorbent is HP
2One of MGL, NKA-9, AB-8 or S-8.
8. according to the described method of claim 1; It is characterized in that: temperature is controlled at below 45 ℃ when reclaiming ethanol in (2) step and (3) step; Vacuum degree control-below the 0.08Mpa; Service temperature was controlled at below 40 ℃ when reverse osmosis membrane concentrated in (3) step, advanced film pressure and was controlled at below 15 Bar.
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| CN106279091A (en) * | 2016-08-15 | 2017-01-04 | 湖北中鑫生物科技有限公司 | A kind of preparation method of L-Epicatechin gallate monomer |
| CN106380457A (en) * | 2016-08-26 | 2017-02-08 | 江苏天晟药业股份有限公司 | Preparation method of epicatechin gallate |
| CN109384762A (en) * | 2018-12-14 | 2019-02-26 | 成都华高生物制品有限公司 | The extracting method of ECG catechin in a kind of tealeaves |
| CN112142707A (en) * | 2020-10-20 | 2020-12-29 | 成都华高生物制品有限公司 | Production and preparation process of epicatechin |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106279091A (en) * | 2016-08-15 | 2017-01-04 | 湖北中鑫生物科技有限公司 | A kind of preparation method of L-Epicatechin gallate monomer |
| CN106380457A (en) * | 2016-08-26 | 2017-02-08 | 江苏天晟药业股份有限公司 | Preparation method of epicatechin gallate |
| CN106380457B (en) * | 2016-08-26 | 2019-01-01 | 江苏天晟药业股份有限公司 | The preparation method of L-Epicatechin gallate |
| CN109384762A (en) * | 2018-12-14 | 2019-02-26 | 成都华高生物制品有限公司 | The extracting method of ECG catechin in a kind of tealeaves |
| CN112142707A (en) * | 2020-10-20 | 2020-12-29 | 成都华高生物制品有限公司 | Production and preparation process of epicatechin |
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