CN115536521A - Preparation method of hydroxycitric acid in lucuma tenuifolia fruits - Google Patents
Preparation method of hydroxycitric acid in lucuma tenuifolia fruits Download PDFInfo
- Publication number
- CN115536521A CN115536521A CN202210882067.7A CN202210882067A CN115536521A CN 115536521 A CN115536521 A CN 115536521A CN 202210882067 A CN202210882067 A CN 202210882067A CN 115536521 A CN115536521 A CN 115536521A
- Authority
- CN
- China
- Prior art keywords
- hydroxycitric acid
- phase
- concentration
- mass ratio
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- ZMJBYMUCKBYSCP-UHFFFAOYSA-N Hydroxycitric acid Chemical compound OC(=O)C(O)C(O)(C(O)=O)CC(O)=O ZMJBYMUCKBYSCP-UHFFFAOYSA-N 0.000 title claims abstract description 96
- 229940089491 hydroxycitric acid Drugs 0.000 title claims abstract description 88
- 235000013399 edible fruits Nutrition 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 11
- 244000266507 Pouteria lucuma Species 0.000 title description 4
- 235000009321 Pouteria lucuma Nutrition 0.000 title description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 48
- 235000000885 Garcinia xanthochymus Nutrition 0.000 claims abstract description 32
- 238000000605 extraction Methods 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 28
- 241000593508 Garcinia Species 0.000 claims abstract description 24
- 230000001376 precipitating effect Effects 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 7
- 241000598860 Garcinia hanburyi Species 0.000 claims abstract description 5
- 238000013375 chromatographic separation Methods 0.000 claims abstract description 5
- 229940117709 gamboge Drugs 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- 239000000243 solution Substances 0.000 claims description 31
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 14
- 239000000047 product Substances 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 11
- 239000000706 filtrate Substances 0.000 claims description 10
- 238000004587 chromatography analysis Methods 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000002425 crystallisation Methods 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 238000004806 packaging method and process Methods 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 238000005119 centrifugation Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 239000011259 mixed solution Substances 0.000 claims description 5
- 239000012141 concentrate Substances 0.000 claims description 4
- 239000003480 eluent Substances 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 238000003809 water extraction Methods 0.000 claims description 4
- 230000005526 G1 to G0 transition Effects 0.000 claims description 3
- 239000012153 distilled water Substances 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- 239000012528 membrane Substances 0.000 claims description 3
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- 238000000967 suction filtration Methods 0.000 claims description 3
- 238000000108 ultra-filtration Methods 0.000 claims description 3
- 241000157554 Luculia Species 0.000 claims description 2
- 238000005191 phase separation Methods 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000004042 decolorization Methods 0.000 claims 1
- 229910001873 dinitrogen Inorganic materials 0.000 claims 1
- 238000010298 pulverizing process Methods 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000012071 phase Substances 0.000 description 56
- 244000119461 Garcinia xanthochymus Species 0.000 description 8
- 235000013305 food Nutrition 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 240000006053 Garcinia mangostana Species 0.000 description 3
- 235000017048 Garcinia mangostana Nutrition 0.000 description 3
- 229920002527 Glycogen Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229940096919 glycogen Drugs 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 241000598812 Garcinia tinctoria Species 0.000 description 2
- 235000005206 Hibiscus Nutrition 0.000 description 2
- 235000007185 Hibiscus lunariifolius Nutrition 0.000 description 2
- 244000284380 Hibiscus rosa sinensis Species 0.000 description 2
- 239000007836 KH2PO4 Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003729 cation exchange resin Substances 0.000 description 2
- 235000021438 curry Nutrition 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 2
- 235000019796 monopotassium phosphate Nutrition 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000001814 pectin Substances 0.000 description 2
- 229920001277 pectin Polymers 0.000 description 2
- 235000010987 pectin Nutrition 0.000 description 2
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 102000004146 ATP citrate synthases Human genes 0.000 description 1
- 108090000662 ATP citrate synthases Proteins 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 235000000832 Ayote Nutrition 0.000 description 1
- 241000345998 Calamus manan Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 240000004244 Cucurbita moschata Species 0.000 description 1
- 235000009854 Cucurbita moschata Nutrition 0.000 description 1
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 1
- 206010014020 Ear pain Diseases 0.000 description 1
- 244000245602 Garcinia atroviridis Species 0.000 description 1
- 241001620225 Garcinia multiflora Species 0.000 description 1
- 241000496351 Garcinia spicata Species 0.000 description 1
- 241001430578 Garcinia yunnanensis Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- CTYZDZBOBNKJOV-UHFFFAOYSA-N OC(=O)C(O)C(O)(C(O)=O)CC(O)=O.OC(=O)C(O)C(O)(C(O)=O)CC(O)=O Chemical compound OC(=O)C(O)C(O)(C(O)=O)CC(O)=O.OC(=O)C(O)C(O)(C(O)=O)CC(O)=O CTYZDZBOBNKJOV-UHFFFAOYSA-N 0.000 description 1
- 208000025157 Oral disease Diseases 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000011759 adipose tissue development Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 230000004596 appetite loss Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 235000011869 dried fruits Nutrition 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 208000007176 earache Diseases 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 230000004136 fatty acid synthesis Effects 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 208000014617 hemorrhoid Diseases 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 208000028774 intestinal disease Diseases 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 208000030194 mouth disease Diseases 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000012946 outsourcing Methods 0.000 description 1
- 208000027753 pain disease Diseases 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- -1 polyethylene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 235000012950 rattan cane Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 235000019614 sour taste Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for extracting and purifying hydroxycitric acid from garcinia cambogia, which takes the garcinia cambogia as a raw material and comprises the following steps: (1) extracting gamboge; (2) centrifuging, concentrating, precipitating with ethanol and concentrating the extract; (3) aqueous two-phase extraction; (4) Three-band simulated moving bed chromatographic separation of hydroxycitric acid; and (5) preparing a finished product of the hydroxycitric acid. The method prepares the high-content hydroxycitric acid, has advanced and unique process, and is suitable for industrial mass production.
Description
Technical Field
The invention relates to a preparation method of hydroxycitric acid in lucuma rattan fruits.
Background
Hydroxycitric acid (Hydroxycitric acid), chinese name: 2-hydroxycitric acid, 1,2-dihydroxy-1,2,3-propane tricarboxylic acid, CAS No.6205-14-7, readily soluble in water, slightly soluble in methanol, poorly soluble in chloroform, petroleum ether, and benzene, formula: c 6 H 8 O 8 Molecular weight: 208.12, structural formula as follows:
hydroxycitric acid is a natural organic acid, mainly distributed in the India subcontinent, western Srilanka, south Africa and Boraginia, and is wild in the India and Srilanka in tropical rainforest areas. Is present in Garcinia cambogia, garcinia
Pericarp of indica and Garcinia atroviridis is also found in Hibiscus (Hibiscus). Garcinia cambogia is a tree of the genus Garcinia of dicotyledonous plants, also known as Malabatamarind (Malabartamarinade), and the fruit, like orange, is yellow in color, has an outer surface similar to pumpkin, and has several longitudinal furrows. For centuries, southern India and Thailand have been cultivated in large numbers for use as herbal medicines. In the late 60's of the 20 th century, scientists found that this fruit contained citric acid, called hydroxycitric acid, like orange and lemon in its interior, which was named as hydroxycitric acid (agri. And food chemistry,2002, 50, 10-22). Pharmacological action of hydroxycitric acid: (1) inhibit fat synthesis, and prevent glucose from synthesizing fat in vivo. Inhibit ATP-Citrate lyase activity, and prevent sugar from converting into excessive fat. (2) Burning fat, stimulating body function, releasing fat,
converting the excess energy into readily consumable glycogen. (3) Regulate fat metabolism, and store excessive nutrients not consumed by the body as calories in the form of glycogen in the muscles and liver. (4) Increase glycogen storage capacity, decrease fat production, and slow down carbohydrate and protein production.
Scientists separate hydroxycitric acid from gamboges fruits, and the hydroxycitric acid has unique regulation effect on fatty acid synthesis, adipogenesis, appetite and weight loss, promotes the combustion of fatty acid by inhibiting the synthesis of fat, reduces the intake of food, integrates the functions of slimming and losing weight, has good weight-losing effect, and is a beneficial and healthy weight-losing health-care raw material. Can be used as medicine for protecting heart, reducing weight, improving endurance, and treating rheumatism and intestinal diseases, and can be used as veterinary medicine for treating oral diseases of livestock. Can be used as ingredient to impart sour taste to curry, and can also be used for preparing syrup. The fruit can be used for expelling parasites, and treating hemorrhoid, dysentery, tumor, pain and heart disease. In srilanka, dried fruit peel is used together with salt to cure fish, in malaysia, sun-dried unripe peel is added as sour agent to curry, and can also be used together with alum as fixing agent to dye silk, and leaves and roots are boiled to treat earache (Sichuan food and fermentation, 2006, 42, 19-23; chinese food additive, 2004,4, 59-63). At present, various functional foods and weight-losing health-care products containing hydroxycitric acid are on the market at home and abroad. Wang Kaizhi in "weight-reducing food xinxiu - Garcinia (Garcinia) plants are reported to be evergreen trees or shrubs, spread over tropical Asia, africa and Bornesia, about 200 species of this genus, 30 of which are produced only in India. Particularly the western coast of india, as well as the inhabitants of laos, malaysia, thailand and burma, have long been eating gamboges. Garcinia is also known as mangosteen and is distributed in south ChinaThere are Garcinia multiflora, garcinia kaempferi, garcinia mangostana, garcinia spicata, and Garcinia yunnanensis. In addition, the famous tropical fruit of this genus, namely, the mangosteen, is cultivated in south China and Taiwan.
Yi Xin systematic study of the purification process of hydroxycitric acid from Garcinia cambogia was performed by comparing D201, D315, D301, HZ - 202 and 335, screening the optimal resin D201, determining the optimal adsorption and desorption process conditions, wherein the pH value of the loading solution is 5, the concentration is 3.12mg/mL, the flow rate is 1mL/min, the eluent is 0.4moL/L sodium chloride solution, the elution flow rate is 1mL/min, and the purity of the hydroxycitric acid sample solution is improved from 40.3% to 91.3% after the hydroxycitric acid sample solution is adsorbed and desorbed by the D201 resin (food and machinery, 2014, 30, 179-184). Moffett et al uses pericarp of Garcinia cambogia as raw material, water as extractant, the extract passes through anion exchange resin column, and is eluted with sodium hydroxide solution, and the eluate passes through cation exchange resin to obtain hydroxycitric acid with 23-54% content (US 5656314). Lewis et al extract hydroxycitric acid from Cambogia gambogia pericarp by decocting with water under reduced pressure, concentrate the extract, precipitate with ethanol, filter, remove pectin, basify the filtrate, recover acid by cation exchange resin column, concentrate hydroxycitric acid and dry to obtain crude product (phytochemistry, 1965,4, 619-625). Lewis has also reported the extraction and separation of hydroxycitric acid from Cambogia gambogia using acetone, the concentration of the acetone extract, and the recovery of acetone to obtain a crude hydroxycitric acid extract (u.s 4005086). Guthrie et al and Moffett et al report a process for preparing hydroxycitric acid from garcinia cambogia pericarp with crude hydroxycitric acid content of 23-54% and lactone content of 6-20%, respectively (U.S. 4006166, U.S. 565656565631. Majeed et al reported the extraction of hydroxycitric acid from Garcinia cambogia fruits with higher alcohols (U.S 5783603). Balalubramanyam et al reported extraction of hydroxycitric acid with water (u.s 6160172). Ibnusaud et al reported extracting fresh and dried Cambogia, indica and atroviridis gamboge pericarp with boiling water, extracting the pericarp 4-5 times, extracting for 20h, concentrating the extract, precipitating with ethanol, filtering to remove pectin, the filtrate being an aqueous solution of hydroxycitric acid (U.S. 6147228).
At present, few reports on the extraction of hydroxycitric acid from garcinia cambogia fruits in China exist, and the extraction method reported in the literature lags behind, the garcinia cambogia fruits are used as raw materials, and the method comprises the following steps: (1) extracting gamboge; (2) centrifuging, concentrating, precipitating with ethanol and concentrating the extract; (3) aqueous two-phase extraction; (4) Three-band simulated moving bed chromatographic separation of hydroxycitric acid; and (5) preparing a finished product of the hydroxycitric acid. The method prepares the high-content hydroxycitric acid, has advanced and unique process, and is suitable for industrial mass production.
Disclosure of Invention
In order to overcome the defects in the background art, the invention aims to provide a method for extracting and purifying hydroxycitric acid from luculia repens.
The technical solution of the invention is as follows:
a preparation method of hydroxycitric acid in Garcinia cambogia fruits takes Garcinia cambogia fruits as raw materials, and the method comprises the following steps: (1) extracting gamboge; (2) centrifuging, concentrating, precipitating with ethanol and concentrating the extract; (3) aqueous two-phase extraction; (4) Three-band simulated moving bed chromatographic separation of hydroxycitric acid; and (5) preparing a finished product of the hydroxycitric acid.
A preparation method of hydroxycitric acid in lucuma tenuifolia fruits is characterized in that subcritical water is adopted for extraction in the step (1), high-purity nitrogen is introduced into a subcritical water extraction device, deoxygenated distilled water is used as an extractant, the material-water ratio is 1: 10-20 (g: mL), the extraction temperature is 100-150 ℃, the extraction time is 30-60 min, the pressure is controlled at 3-10 Mpa, and hydroxycitric acid extract liquid is obtained,
a preparation method of hydroxycitric acid in Garcinia cambogia is characterized in that, the extracting solution in the step (2) is centrifuged, concentrated, precipitated with alcohol and concentrated;
the centrifugation is carried out for 10-20 min at the rotating speed of 3000-5000 r/min;
the concentration is carried out, and an ultrafiltration membrane with the molecular weight cut-off of 10-50 kD is used for concentrating to 1/3-1/10 of the original volume;
the alcohol precipitation is to add 95-100 wt% ethanol into the hydroxyl citric acid concentrated solution to ensure that the final concentration of the ethanol is 70-80 wt%, to stir evenly, to stand and precipitate for 5-10 h, to perform suction filtration to obtain filtrate;
concentrating the filtrate into a solution with the hydroxycitric acid content of 30-50 wt% at the vacuum degree of 82.7-90.6 KPa and the temperature of 50-60 ℃ to obtain a hydroxycitric acid concentrated solution;
a preparation method of hydroxycitric acid in lucidus fruits is characterized in that aqueous two-phase extraction is carried out in step (3), and (NH) is added into hydroxycitric acid concentrated solution obtained in step (2) 4 ) 2 SO 4 So that (NH) 4 ) 2 SO 4 The mass ratio concentration of the ethanol is 10-20%, then ethanol is added to ensure that the mass ratio concentration of the ethanol is 10-20%, a double aqueous phase system is obtained, an upper phase and a lower phase are obtained after standing and phase splitting, and the upper phase is collected;
and/or, adding K into the hydroxycitric acid solution 2 HPO 4 So that K is 2 HPO 4 The mass ratio concentration of the acetone is 30-40%, then acetone is added to ensure that the mass ratio concentration of the acetone is 30-40% to obtain a double water phase system, an upper phase and a lower phase are obtained after standing and phase splitting, and the upper phase is collected;
and/or, adding Na into the hydroxycitric acid solution 2 SO 4 So that Na is present 2 SO 4 The mass ratio concentration of the N-propanol is 20-30%, then the N-propanol is added to ensure that the mass ratio concentration of the N-propanol is 20-30%, a double water phase system is obtained, an upper phase and a lower phase are obtained after standing and phase splitting, and the upper phase is collected;
and/or, adding CaCl into the hydroxycitric acid solution 2 So that CaCl is 2 The mass ratio concentration of the mixed solution is 20-30%, then isopropanol is added to ensure that the mass ratio concentration of the isopropanol is 20-30%, a double water phase system is obtained, an upper phase and a lower phase are obtained after standing and phase splitting, and the upper phase is collected;
and/or adding KH2PO4 into the hydroxycitric acid solution to ensure that the mass ratio concentration of the KH2PO4 is 20-30%, then adding n-propanol to ensure that the mass ratio concentration of the n-propanol is 20-30% to obtain a double water phase system, standing for phase separation to obtain an upper phase and a lower phase, and collecting the upper phase.
A preparation method of hydroxycitric acid in Garcinia cambogia is characterized in that the upper phase in the step (4) is collected, hydroxycitric acid is separated and purified by applying a three-band simulated moving bed chromatography, octadecylsilane chemically bonded silica is adopted as a stationary phase of the simulated moving bed chromatography, a mixed solution of methanol and water is adopted as a mobile phase, the volume ratio of the methanol to the water is 45: 55 (V/V),
the three-zone simulated moving bed chromatographic system consists of 4-8 chromatographic columns, and the chromatographic columns are divided into three zones: each zone is composed of 1-4 identical chromatographic columns which are connected in series, and the operating parameters of the simulated moving bed chromatographic system are as follows: the flow rate UF of the sample injection liquid is 0.2-3.0 mL/min; the flow rate UD of the eluent is 5.0-50.0 mL/min; the flow rate of the extraction liquid UE is 3.0-30.0 mL/min; the flow rate UR of the raffinate is 2.0-20.0 mL/min; the switching time TS is 1-6 min; obtaining the separating liquid of the hydroxycitric acid.
A preparation method of hydroxycitric acid in Garcinia cambogia is characterized in that in the step (5), the hydroxycitric acid finished product is prepared by carrying out steps of decoloring, crystallizing, filtering, recrystallizing, centrifuging, drying, crushing, packaging and the like on the separation liquid obtained in the step (4) to obtain the finished product hydroxycitric acid.
Adding activated carbon into the decoloration, slowly heating the decoloration solution to 70 +/-2 ℃ under stirring, and keeping the temperature for refluxing for 1 hour;
the concentration is carried out under the conditions of vacuum degree of (0.06-0.08) Mpa and 50 +/-2 ℃ and is carried out under reduced pressure until the volume is 1/2-1/3 of the initial volume;
the drying and crushing are carried out, the drying is carried out for 2.5h under the condition that the temperature is between 40 and 60 ℃ and is between 0.06 and 0.08 Mpa, the crushing is carried out by a crusher, the rotation is carried out for 30min at the rotating speed of 2r/min, and the mixing is completed.
Detailed Description
A preparation method of hydroxycitric acid in Garcinia cambogia fruits takes Garcinia cambogia fruits as raw materials, and the method comprises the following steps: the method comprises the following steps: extracting garcinia cambogia; step two: centrifuging, concentrating, precipitating with ethanol, and concentrating; step three: aqueous two-phase extraction: step four: three-band simulated moving bed chromatographic separation of hydroxycitric acid; step five: and (5) preparing a finished product of the hydroxycitric acid.
Step one of implementation 1: crushing garcinia cambogia, putting the garcinia cambogia into a subcritical water extraction device, introducing high-purity nitrogen, taking deoxidized distilled water as an extracting agent, adding deionized water at a material-water ratio of 1: 10-20 (g: mL), extracting at the temperature of 100-150 ℃ for 10-120 min, uniformly stirring, screwing down an extraction kettle cover to seal the extraction kettle, controlling the pressure of the extraction kettle to be 3-10 Mpa, then putting the extraction kettle on a temperature heating controller, controlling the preheating temperature of the temperature heating controller to be 100-200 ℃, heating the extraction kettle to make the temperature of materials in the extraction kettle be 140 ℃ by the temperature heating controller, keeping the temperature at 140 ℃ for 10min, taking out the extraction kettle, cooling the extraction kettle to room temperature in 5min by using cold water, opening a valve at the bottom of the extraction kettle, allowing an extraction liquid extract to flow into a stirring tank, separating liquid residues in the materials, and mechanically filtering to obtain an extraction liquid containing the hydroxycitric acid.
Step two: centrifuging the filtrate in the stirring tank at a rotating speed of 3000-5000 r/min for 10-20 min, and concentrating the supernatant to 1/3-1/10 of the original volume by using an ultrafiltration membrane with the molecular weight cut-off of 10-50 kD to obtain a concentrated solution containing hydroxyl citric acid; adding 95-100 wt% ethanol into the concentrated solution containing the hydroxycitric acid to ensure that the final concentration of the ethanol is 70-80 wt%, uniformly stirring, standing and precipitating for 5-10 h, carrying out suction filtration to obtain a filtrate, and concentrating the filtrate into a solution with the hydroxycitric acid content of 30-50 wt% at the vacuum degree of 82.7-90.6 KPa and the temperature of 50-60 ℃ to obtain a hydroxycitric acid concentrated solution;
step three: adding (NH) into 50mL of hydroxycitric acid concentrated solution 4 ) 2 SO 4 So that (NH 4) 2 SO 4 The mass ratio concentration of the ethanol is 10 percent, then ethanol is added to ensure that the mass ratio concentration of the ethanol is 10 percent, a double water phase system is obtained, an upper phase and a lower phase are obtained after standing and phase splitting, and the upper phase is collected.
Step four: collecting upper phase in the double water phase extraction, separating and purifying the hydroxycitric acid by using a three-band simulated moving bed chromatography, wherein the stationary phase of the simulated moving bed chromatography adopts octadecylsilane chemically bonded silica, the mobile phase adopts a mixed solution of methanol and water, the volume ratio of the methanol to the water is 45: 55 (V/V), a three-band simulated moving bed chromatography system consists of 4-8 chromatographic columns, and the chromatographic columns are divided into three bands: each zone is composed of 1-4 same chromatographic columns which are connected in series, and the operating parameters of the simulated moving bed chromatographic system are as follows: the flow rate UF of the sample injection liquid is 0.2-3.0 mL/min; the flow rate UD of the eluent is 5.0-50.0 mL/min; the flow rate of the extraction liquid UE is 3.0-30.0 mL/min; the flow rate UR of the raffinate is 2.0-20.0 mL/min; the switching time TS is 1-6 min.
Step five: adding 3.0kg of activated carbon into hydroxycitric acid separated and purified by a three-belt simulated moving bed chromatography, sealing a feeding port, slowly heating to 70 +/-2 ℃ under stirring, keeping the temperature for refluxing for 1 hour, recording the temperature every 30min, after timing is finished, closing a material reflux valve on a reaction kettle, adjusting a hot steam valve on the reaction kettle to increase the pressure in the kettle to 0.12-0.14 MPa, closing a heat-carrying steam valve of the reaction kettle, installing a filter while dissolving, slowly opening a material discharge valve of the reaction kettle after a concentration person in a clean area confirms that the material is ready to be received, pressing the dissolved material into the filter through a pipeline, strictly operating according to the operating rules of the filter during filtering, closing a material feeding valve after receiving filtrate from a dissolving station, opening a solvent recovery valve on a concentration tank, opening a vacuum valve, opening a hot steam valve on the concentration tank, carrying the hot steam valve on the concentration tank under the conditions of 50 +/-2 ℃ of (0.06-0.08) MPa, carrying out reduced pressure concentration, observing the material in the concentration tank to 1/2 of the initial concentration volume, closing the heat-carrying steam valve, closing the vacuum valve, pressing the crystallization tank by compressed air, opening the crystallization valve, opening a crystallization tank, cooling water pump, cooling the crystallization tank, and cooling the crystallization tank to 12-16 hours. And (3) pouring the obtained materials into a centrifuge for centrifugation in batches, weighing and metering the centrifuged materials, drying the weighed materials at a drying station, transferring the centrifuged refined hydroxycitric acid wet product into a dryer, drying the dried product at the temperature of 0.06-0.08 MPa and 40-60 ℃ for 2.5 hours, checking that the drying quality is qualified, and weighing and crushing the dried product at the drying station. Crushing the dried refined hydroxycitric acid by a crusher, applying for sampling detection on the crushed material by an intermediate station after crushing, calculating according to the weight of 50.0kg of the finished product of the refined hydroxycitric acid after mixing, determining a mixing batch, adding the mixing batch into a total mixer, rotating at the rotating speed of 2r/min for 30min, completing mixing, subpackaging the materials in polyethylene packaging bags, adjusting the packaging amount of each bag to be 25.0 +/-0.1 kg between inner packages, sampling, detecting, pricking and sealing, sleeving a layer 2 packaging bag, pricking and sealing, then transferring to an outer packaging room from a transfer window, outsourcing, labeling and warehousing.
The first and second steps of the 2 process are the same as those of the 1 process.
Taking 70mL of hydroxycitric acid concentrated solution, adding K 2 HPO 4 So that K is 2 HPO 4 The mass ratio concentration of the acetone is 30 percent, then acetone is added to ensure that the mass ratio concentration of the acetone is 30 percent, a double water phase system is obtained, an upper phase and a lower phase are obtained after standing and phase splitting, and the upper phase is collected.
Step four and step five are implemented by the same method 1.
The first and second steps of the 3 process are the same as those of the 1 process.
Taking 40mL of hydroxycitric acid concentrated solution, adding Na 2 SO 4 So that Na is present 2 SO 4 The mass ratio concentration of the N-propanol is 20%, then the N-propanol is added to ensure that the mass ratio concentration of the N-propanol is 20%, a double aqueous phase system is obtained, an upper phase and a lower phase are obtained after standing and phase splitting, and the upper phase is collected.
And the fourth step and the fifth step are carried out in the same way as the step 1.
The method of the first and second steps is the same as the method of the first step 1.
Taking 60mL of hydroxycitric acid concentrated solution, adding CaCl 2 So that CaCl is 2 The mass ratio concentration of the isopropanol is 20-30%, then the isopropanol is added to ensure that the mass ratio concentration of the isopropanol is 20-30%, a double water phase system is obtained, an upper phase and a lower phase are obtained after standing and phase splitting, and the upper phase is collected.
Step four and step five are implemented by the same method 1.
The method 1 is the same as the method 1 in the step 5.
Adding KH into 90mL of hydroxycitric acid concentrate 2 PO 4 Make KH 2 PO 4 The mass ratio concentration of the N-propanol is 20-30%, then the N-propanol is added to ensure that the mass ratio concentration of the N-propanol is 20-30%, a double water phase system is obtained, an upper phase and a lower phase are obtained after standing and phase splitting, and the upper phase is collected.
The fourth and fifth methods are the same as embodiment 1.
Claims (6)
1. A preparation method of hydroxycitric acid in Garcinia cambogia fruits takes Garcinia cambogia fruits as raw materials, and the method comprises the following steps: (1) extracting gamboge; (2) centrifuging, concentrating, precipitating with ethanol and concentrating the extract; (3) aqueous two-phase extraction; (4) Chromatographic separation of the hydroxycitric acid by a three-band simulated moving bed; and (5) preparing a finished product of the hydroxycitric acid.
2. The method for preparing hydroxycitric acid from luculia scandens fruit as claimed in claim 1, wherein the subcritical water extraction is adopted in step (1), high-purity nitrogen gas is introduced into the subcritical water extraction device, deoxygenated distilled water is used as an extractant, the ratio of material to water is 1: 10-20 (g: mL), the extraction temperature is 100-150 ℃, the extraction time is 30-60 min, and the pressure is controlled at 3-10 MPa, so as to obtain the extract of hydroxycitric acid.
3. The method for preparing hydroxycitric acid from Garcinia cambogia as claimed in claim 1, wherein the step (2) comprises centrifugation, concentration, alcohol precipitation and concentration of the extractive solution;
the centrifugation is carried out for 10-20 min at the rotating speed of 3000-5000 r/min;
the concentration is carried out, and an ultrafiltration membrane with the molecular weight cut-off of 10-50 kD is used for concentrating to 1/3-1/10 of the original volume;
the alcohol precipitation is to add 95-100 wt% ethanol into the hydroxyl citric acid concentrated solution to ensure that the final concentration of the ethanol is 70-80 wt%, to stir evenly, to stand and precipitate for 5-10 h, to perform suction filtration to obtain filtrate;
and concentrating the filtrate into a solution with the hydroxycitric acid content of 30-50 wt% at the vacuum degree of 82.7-90.6 KPa and the temperature of 50-60 ℃ to obtain the hydroxycitric acid concentrated solution.
4. The method for preparing hydroxycitric acid from Garcinia cambogia as claimed in claim 1, wherein the aqueous two-phase extraction is performed in step (3), and (NH) is added to the hydroxycitric acid concentrate obtained in step (2) 4 ) 2 SO 4 So that (NH) 4 ) 2 SO 4 The mass ratio concentration of the ethanol is 10 to 20 percent, and then the ethanol is added to ensure that the mass ratio concentration of the ethanol is 10 to 20 percentObtaining a double water phase system, standing for phase splitting to obtain an upper phase and a lower phase, and collecting the upper phase;
and/or, adding K into the hydroxycitric acid solution 2 HPO 4 So that K is 2 HPO 4 The mass ratio concentration of the acetone is 30-40%, then acetone is added to ensure that the mass ratio concentration of the acetone is 30-40% to obtain a double water phase system, an upper phase and a lower phase are obtained after standing and phase splitting, and the upper phase is collected;
and/or, adding Na into the hydroxycitric acid solution 2 SO 4 So that Na is present 2 SO 4 The mass ratio concentration of the N-propanol is 20-30%, then the N-propanol is added to ensure that the mass ratio concentration of the N-propanol is 20-30%, a double water phase system is obtained, an upper phase and a lower phase are obtained after standing and phase splitting, and the upper phase is collected;
and/or, adding CaCl into the hydroxycitric acid solution 2 So that CaCl is 2 The mass ratio concentration of the mixed solution is 20-30%, then isopropanol is added to ensure that the mass ratio concentration of the isopropanol is 20-30%, a double water phase system is obtained, an upper phase and a lower phase are obtained after standing and phase splitting, and the upper phase is collected;
and/or, adding KH into the hydroxycitric acid solution 2 PO 4 Make KH 2 PO 4 Then adding n-propanol to make the mass ratio concentration of the n-propanol be 20-30% to obtain a double water phase system, standing for phase separation to obtain an upper phase and a lower phase, and collecting the upper phase.
5. The method for preparing hydroxycitric acid from Garcinia cambogia as claimed in claim 1, wherein the upper phase in step (4) is collected, hydroxycitric acid is separated and purified by using a three-band simulated moving bed chromatography, octadecylsilane chemically bonded silica is used as a stationary phase of the simulated moving bed chromatography, a mixed solution of methanol and water is used as a mobile phase, the volume ratio of methanol to water is 45: 55 (V/V), the three-band simulated moving bed chromatography system comprises 4 to 8 chromatographic columns, and the chromatographic columns are divided into three bands: each zone is composed of 1-4 same chromatographic columns which are connected in series, and the operating parameters of the simulated moving bed chromatographic system are as follows: the flow rate UF of the sample injection liquid is 0.2-3.0 mL/min; the flow rate UD of the eluent is 5.0-50.0 mL/min; the flow rate of the extraction liquid UE is 3.0-30.0 mL/min; the flow rate UR of the raffinate is 2.0-20.0 mL/min; the switching time TS is 1-6 min; obtaining the separating liquid of the hydroxycitric acid.
6. The method for preparing hydroxycitric acid from Garcinia cambogia as claimed in claim 1, wherein the hydroxycitric acid product obtained in step (5) is obtained by subjecting the separated liquid obtained in step (4) to decolorization, crystallization, filtration, recrystallization, centrifugation, drying, pulverization, packaging, etc.
Adding active carbon into the decoloration, slowly heating the decoloration solution to 70 +/-2 ℃ under stirring, and keeping the temperature for refluxing for 1 hour;
the concentration is carried out under the conditions of vacuum degree of (0.06-0.08) Mpa and 50 +/-2 ℃ and reduced pressure concentration to 1/2-1/3 of the initial volume;
the drying and crushing are carried out, the drying is carried out for 2.5h under the condition that the temperature is between 40 and 60 ℃ and is between 0.06 and 0.08 Mpa, the crushing is carried out by a crusher, the rotation is carried out for 30min at the rotating speed of 2r/min, and the mixing is completed.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210882067.7A CN115536521A (en) | 2022-07-17 | 2022-07-17 | Preparation method of hydroxycitric acid in lucuma tenuifolia fruits |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210882067.7A CN115536521A (en) | 2022-07-17 | 2022-07-17 | Preparation method of hydroxycitric acid in lucuma tenuifolia fruits |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN115536521A true CN115536521A (en) | 2022-12-30 |
Family
ID=84724247
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210882067.7A Pending CN115536521A (en) | 2022-07-17 | 2022-07-17 | Preparation method of hydroxycitric acid in lucuma tenuifolia fruits |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115536521A (en) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1162910A (en) * | 1994-08-24 | 1997-10-22 | 新生草本植物公司 | Hydroxycitric acid concentrate and method of making |
| CN104610049A (en) * | 2015-02-12 | 2015-05-13 | 白心亮 | Method for extracting hydroxyl citric acid from garcinia cambogia |
| CN104725218A (en) * | 2015-03-02 | 2015-06-24 | 李玉山 | Method for extracting and purifying hydroxycitric acid from garcinia cambogia |
| CN104844447A (en) * | 2015-04-15 | 2015-08-19 | 义乌章舸生物工程有限公司 | Method for preparing high-purity hydroxycitric acid with garcinia cambogia as raw material |
| CN108047029A (en) * | 2017-12-20 | 2018-05-18 | 南京慧博生物科技有限公司 | A kind of preparation method of the extraction purification hydroxycitric acid from Garcinia Cambogia |
| CN110590543A (en) * | 2019-08-26 | 2019-12-20 | 湖南人文科技学院 | Method for extracting hydroxycitrate from lucidus fruit |
-
2022
- 2022-07-17 CN CN202210882067.7A patent/CN115536521A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1162910A (en) * | 1994-08-24 | 1997-10-22 | 新生草本植物公司 | Hydroxycitric acid concentrate and method of making |
| CN104610049A (en) * | 2015-02-12 | 2015-05-13 | 白心亮 | Method for extracting hydroxyl citric acid from garcinia cambogia |
| CN104725218A (en) * | 2015-03-02 | 2015-06-24 | 李玉山 | Method for extracting and purifying hydroxycitric acid from garcinia cambogia |
| CN104844447A (en) * | 2015-04-15 | 2015-08-19 | 义乌章舸生物工程有限公司 | Method for preparing high-purity hydroxycitric acid with garcinia cambogia as raw material |
| CN108047029A (en) * | 2017-12-20 | 2018-05-18 | 南京慧博生物科技有限公司 | A kind of preparation method of the extraction purification hydroxycitric acid from Garcinia Cambogia |
| CN110590543A (en) * | 2019-08-26 | 2019-12-20 | 湖南人文科技学院 | Method for extracting hydroxycitrate from lucidus fruit |
Non-Patent Citations (4)
| Title |
|---|
| 俞泉;胡一鸿;: "羟基柠檬酸研究进展", 生命的化学, no. 03, 15 March 2020 (2020-03-15) * |
| 李春宇;张彤;郭庆华;孙端方;: "大果藤黄乙醇提取物的降血脂与抗氧化性", 贵州农业科学, no. 07, 15 July 2017 (2017-07-15) * |
| 袁尔东;: "功效活性成分-羟基柠檬酸的研究进展", 四川食品与发酵, no. 02, 30 June 2006 (2006-06-30) * |
| 赵希荣: "羟基柠檬酸的来源、制备方法和性质", 中国食品添加剂, no. 04, 15 August 2004 (2004-08-15) * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101912480B (en) | Method for preparing procyanidin extract of lycium ruthenicum murr | |
| CN102106931B (en) | Method for producing diverse extracts of berry tea | |
| CN108752231B (en) | Method for extracting theanine from sweet tea and simultaneously extracting rubusoside and tea polyphenol | |
| CN107898868B (en) | Method for synchronously separating and preparing lycium erythrophyll, lycium barbarum polysaccharide and lycium barbarum flavone from lycium barbarum | |
| CN108176079B (en) | A method for decolorizing Glycyrrhrizae radix extract | |
| CN112195063A (en) | Preparation method of tea seed oil rich in tea polyphenol | |
| CN110981921B (en) | Continuous method for synchronously extracting multiple effective components from figs | |
| CN107098942B (en) | Method for subcritical water extraction of kaempferitrin in radish leaves | |
| CN109053385A (en) | A method of extracting luteolin and resveratrol | |
| CN101659793A (en) | Method for extracting gynura bicolor purpurin | |
| CN104725218A (en) | Method for extracting and purifying hydroxycitric acid from garcinia cambogia | |
| CN110917240B (en) | Continuous method for separating multiple effective components from cyclocarya paliurus | |
| CN115844937B (en) | Preparation method and application of herba Sonchi Oleracei extract with anti-hangover and brain protecting effects | |
| CN115536521A (en) | Preparation method of hydroxycitric acid in lucuma tenuifolia fruits | |
| CN113603742B (en) | Preparation method of mogroside V | |
| CN108409807B (en) | Method for separating and preparing malvidin-3-O-glucoside | |
| CN108250052A (en) | The method of separation and Extraction quebrachite from sapindaceous plant longan or lichee | |
| CN113913029B (en) | Method for preparing effective components of gardenia jasminoides ellis | |
| CN106916065B (en) | Method for preparing high-purity chlorogenic acid from burdock roots | |
| JP3806693B2 (en) | Method for recovering pinitol from soybean processing by-products in high yield | |
| CN110841004B (en) | Process for extracting dendrobium candidum extract from dendrobium candidum at low temperature through hot reflux | |
| CN101732391B (en) | Method for enriching and purifying cardiac glycoside of wormseed mustard herb | |
| CN100500688C (en) | Total saponin of American ginseng and injection liquid thereof | |
| CN108517000B (en) | Method for separating and preparing petunidin-3-O-arabinoside | |
| CN102532219A (en) | Method for enriching and purifying anthocyanin in lonicera caerulea |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |