CN102219664B - Method for extracting walnut ketones from epicarps of carya cathayensis Sarg and preparing walnut ketone standard product - Google Patents
Method for extracting walnut ketones from epicarps of carya cathayensis Sarg and preparing walnut ketone standard product Download PDFInfo
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- CN102219664B CN102219664B CN2011101047571A CN201110104757A CN102219664B CN 102219664 B CN102219664 B CN 102219664B CN 2011101047571 A CN2011101047571 A CN 2011101047571A CN 201110104757 A CN201110104757 A CN 201110104757A CN 102219664 B CN102219664 B CN 102219664B
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- walnut
- nucin
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- epicarps
- carya cathayensis
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- 241000758789 Juglans Species 0.000 title abstract description 11
- 235000009496 Juglans regia Nutrition 0.000 title abstract description 11
- 235000020234 walnut Nutrition 0.000 title abstract description 11
- 240000004875 Carya cathayensis Species 0.000 title abstract description 7
- 235000005663 Carya cathayensis Nutrition 0.000 title abstract description 7
- 150000002576 ketones Chemical class 0.000 title abstract 10
- 101150107869 Sarg gene Proteins 0.000 title abstract 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000007788 liquid Substances 0.000 claims abstract description 16
- 238000000605 extraction Methods 0.000 claims abstract description 10
- 239000002994 raw material Substances 0.000 claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000000284 extract Substances 0.000 claims abstract description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- KQPYUDDGWXQXHS-UHFFFAOYSA-N juglone Chemical compound O=C1C=CC(=O)C2=C1C=CC=C2O KQPYUDDGWXQXHS-UHFFFAOYSA-N 0.000 claims description 40
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 30
- 239000012043 crude product Substances 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 241000899834 Obovaria olivaria Species 0.000 claims description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 11
- 239000000741 silica gel Substances 0.000 claims description 10
- 229910002027 silica gel Inorganic materials 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 238000004587 chromatography analysis Methods 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 9
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 238000012746 preparative thin layer chromatography Methods 0.000 claims description 6
- 229960001866 silicon dioxide Drugs 0.000 claims description 6
- 238000001291 vacuum drying Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 4
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- 239000012535 impurity Substances 0.000 claims description 3
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- 239000006228 supernatant Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 239000012670 alkaline solution Substances 0.000 claims description 2
- 230000001174 ascending effect Effects 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 238000004440 column chromatography Methods 0.000 abstract description 4
- 239000003480 eluent Substances 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 239000002699 waste material Substances 0.000 abstract description 3
- 238000004809 thin layer chromatography Methods 0.000 abstract description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- 238000007664 blowing Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 210000000582 semen Anatomy 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 241000723418 Carya Species 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- 229940088623 biologically active substance Drugs 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
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- 238000001514 detection method Methods 0.000 description 2
- 239000002158 endotoxin Substances 0.000 description 2
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 2
- 229920006008 lipopolysaccharide Polymers 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- ZXYYTDCENDYKBR-SSDOTTSWSA-N (4r)-4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2[C@H](O)CCC(=O)C2=C1O ZXYYTDCENDYKBR-SSDOTTSWSA-N 0.000 description 1
- UPLPHRJJTCUQAY-WIRWPRASSA-N 2,3-thioepoxy madol Chemical compound C([C@@H]1CC2)[C@@H]3S[C@@H]3C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@](C)(O)[C@@]2(C)CC1 UPLPHRJJTCUQAY-WIRWPRASSA-N 0.000 description 1
- 241000143060 Americamysis bahia Species 0.000 description 1
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- 108010074328 Interferon-gamma Proteins 0.000 description 1
- 241000758791 Juglandaceae Species 0.000 description 1
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- 206010028980 Neoplasm Diseases 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
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- 230000004223 radioprotective effect Effects 0.000 description 1
- ZXYYTDCENDYKBR-UHFFFAOYSA-N regiolone Natural products C1=CC=C2C(O)CCC(=O)C2=C1O ZXYYTDCENDYKBR-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
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- 238000000638 solvent extraction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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- Medicines Containing Plant Substances (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention provides method for extracting walnut ketones from epicarps of carya cathayensis Sarg and preparing walnut ketone standard product. The method comprises the steps of: firstly, crushing the epicarps of the carya cathayensis Sargs, moistening with aqueous ammonia, adding 95 percent of ethanol solution, carrying out hot reflux extraction, extracting extract with chloroform to obtain carya cathayensis Sarg ketone sample liquid, concentrating the sample liquid, purifying by thin layer chromatography to obtain rough walnut ketone, further purifying the rough walnut ketone by using C18 reverse-phase column chromatography, collecting the rough walnut ketone eluent by segments, combining the eluent with purity larger than 95 percent detected by HPLC (High Performance Liquid Chromatography), and carrying out nitrogen blowing to remove a solvent, thus obtaining the walnut ketone standard product. For the method, the extraction process is simple, the walnut ketone has high yield and high purity, theoretical and practical application basis can be provided for comprehensively utilizing carya cathayensis Sarg resources by taking the epicarps of the carya cathayensis Sargs as raw materials, thus having an effect on changing wastes into treasures.
Description
Technical background
The invention belongs to Separation of Natural Products purifying field, be specifically related to a kind of method of extracting nucin and prepare the nucin standard substance from hickory nut epicarp.
Background technology
Semen Caryae Cathayensis (Carya cathayensis Sarg.) is the hickory plant, has 2 mutation of 17 kinds.China's Semen Caryae Cathayensis main product in Zhejiang, the temmoku mountain area that has a common boundary, Anhui, be distributed in prosperousization in Linan, Zhejiang Province, in diving, the Lin Qi ,Tang village in Chunan, the filial piety of Anji is rich, minute water of Tonglu; The Ningguo in Anhui Province, Shexian County, Jingde, the counties such as Jixi.In addition, the nineties in 20th century, at the Jinzhai County in Dabie Mountains, Anhui Province district, find the Wild hickory of thousands of mu in flakes.For a long time, the Semen Caryae Cathayensis comprehensive exploitation dynamics of China is inadequate, backward in technique, and resource utilization is lower, substantially take the Semen Caryae Cathayensis product as main.In fact, the Semen Caryae Cathayensis whole body is precious, and timber, bark, branches and leaves, male inflorescence, kind Pu (exocarp), nucleocapsid etc. contain and enrich biologically active substance, and boundless exploitation prospect is arranged.The modern study result shows, juglandaceae plant contains and enriches biologically active substance, and antitumor, antibacterial, allelopathic, desinsection, anti-inflammatory, radioprotective, anti peroxidation of lipid, hypoglycemic effect are arranged, and in addition, its pigment is the good stability of tool also.
For a long time, hickory nut epicarp is deposited in by roadside, small stream as waste always, the not only wasting of resources, and serious environment pollution.Negative impact is caused in Semen Caryae Cathayensis production producing region with regard to the contaminated situation of environment always.Exocarp, by the juice of rainwater or river leaching, has toxic action to fishes and shrimps, and simultaneously, the soil that alkalized, to surrounding environment and ecological generation havoc.
Recent study finds that nucin (Regiolone) is to cancer cells HL-60, Hela, HepG
2Cytotoxicityinvitro is obvious, can suppress again the generation of the RAW264.7 rat macrophage NO that lipopolysaccharides (LPS) and γ-interference (IFN-γ) induce, is the natural product with antitumour activity that a kind of utmost point has exploitation to be worth.
Patent CN 101328114A discloses a kind of method of extracting nucin from green peel of walnut, the method is got raw material dry powder 5kg, by water or 95% extraction using alcohol, through organic solvent extractions such as sherwood oil, ethyl acetate, propyl carbinols, take petroleum ether-ethyl acetate or sherwood oil-acetone as eluent, carry out the ordinary silicon plastic column chromatography and separate, then with petroleum ether-ethyl acetate or sherwood oil-acetone, carry out crystallization and recrystallization obtains 200mg nucin crude product.Can find out, the method yield is equivalent to 40 μ g crude product/g dry powder, and purity is short of, productive rate is lower, and crystallization and recrystallization operating time are long, affected by temperature humidity larger, and nucin have certain water absorbability, so during practical application, this method is inadvisable.Moreover Cortex walnut and hickory nut epicarp there are differences on raw material, composition.
Summary of the invention
The invention provides a kind of method of extracting nucin and prepare the nucin standard substance from hickory nut epicarp.The inventive method technique is simple, and method is reliable, and the yield of nucin is high, good stability, and purity is high, can reach more than 98%.
The technical solution used in the present invention is as follows for achieving the above object:
A kind of method of extracting nucin from hickory nut epicarp, is characterized in that, specifically comprises the following steps:
(1) after Semen Caryae Cathayensis is gathered, peel off hickory nut epicarp, and it is dried in the shade, 45-55 ℃ of vacuum-drying, pulverize, and crosses the 55-65 mesh sieve, and is standby;
(2) add 10-20% ammoniacal liquor in raw material powder, mix thoroughly to moistening;
(3) will be equivalent to raw material powder weight 8-12 95% ethanol doubly and join in moistening shape raw material powder, 50 ℃ of-80 ℃ of thermal backflows are extracted 2-4 time, each 1-1.5h, and the extracting solution centrifugation, merge supernatant liquor, is evaporated to the medicinal extract shape;
(4) medicinal extract 1-3% dissolving with hydrochloric acid, the pH=2-4 of adjusting acid liquid; Acid liquid equal-volume chloroform extraction, get chloroform layer, with the 2-4%NaOH solution left standstill, extracts, and gets upper strata alkali lye, with 10-20% hydrochloric acid, transfers pH=7-9, and standing, lower floor's chloroform layer is the nucin sample liquid.
The nucin that utilizes claim 1 to extract prepares the method for nucin standard substance, it is characterized in that concrete steps are as follows:
(1) prepare the type thin-layer chromatography nucin sample liquid claimed in claim 1 is concentrated after, the Preparative TLC chromatography, scrape the silica gel at position, nucin place, then Soxhlet extracting, vacuum-drying obtains the nucin crude product, the mixed solution of Preparative TLC chromatography developping agent chloroform used, methyl alcohol, ammoniacal liquor, the volume ratio of its each component is chloroform: methyl alcohol: ammoniacal liquor=(62-68): (0.8-1.2): 1,80 ℃-100 ℃ of Soxhlet extraction temperatures;
(2) C
18Reversed phase column chromatography is with C
18Silica gel with methyl alcohol fully soak degassed after, settling methods dress post, after fully washing out impurity with methyl alcohol, use again 20-40% acetonitrile solution balance, with the described nucin dissolving crude product of step (1) upper prop after methyl alcohol, and with 20-40% acetonitrile wash-out, chromatography process carries out at normal temperatures and pressures, wherein, the quality volume (g/ml) of nucin crude product and methyl alcohol is than being 1: (20-40);
(3) elutriant refinement treatment Fractional Collections nucin crude product elutriant, detect purity with HPLC and merge greater than stream part of 95%, and nitrogen is blown away neat solvent, obtains the nucin standard substance.
The described method for preparing the nucin standard substance is characterized in that: to detect the moving phase of purity be acetonitrile solution to HPLC in described step (3), the volume ratio of acetonitrile and water=15: 85 wherein, detection wavelength 258-261nm, column temperature 24-26 ℃.
The described method for preparing the nucin standard substance is characterized in that: step (1) Preparative TLC chromatography silica-gel plate used is: prepare type GF
254Silica-gel plate.
Compared with prior art, the invention has the advantages that:
(1) utilize hickory nut epicarp to extract nucin for raw material, aboundresources, can play the effect of utilization of waste material;
(2) extraction and separation process is simple, and extraction solvent is chloroform, is easy to reclaim; Method is reliable, utilizes Preparative TLC chromatography and C
18Reversed phase column chromatography, adopt suitable developping agent and eluent, optionally nucin separated out to greatest extent.
(3) yield of nucin is high, good stability, and yield is 350 μ g/g.
(4) purity of nucin is high, and purity can reach more than 98%.The finished product good stability.
The present invention is take hickory nut epicarp as raw material, and for comprehensive utilization Semen Caryae Cathayensis Resource Supply is theoretical and the practical application foundation, the present invention, will be to promoting the Semen Caryae Cathayensis industry development, the aspects such as Semen Caryae Cathayensis deep exploitation of resources being had positive effect after industrializing implementation.
Embodiment
Now take laboratory implementation as example, non-limiting examples is described below:
The hickory nut epicarp that will dry in the shade, 50 ℃ of vacuum-dryings, pulverize, and crosses 60 mesh sieves (aperture 0.25mm).Get in the 600g raw material powder that to add concentration be the ammoniacal liquor of 10-20%, mix thoroughly to moistening, then add the ethanol of 6kg95%, 50 ℃-80 ℃ lower thermal backflows are extracted 4 times, each 1.5h, the centrifugal (3500r/min of extracting solution, 15min), merge supernatant liquor, be evaporated to the medicinal extract shape.Medicinal extract, with 300mL 1-3% dissolving with hydrochloric acid, obtains acid liquid (transferring pH=2-4); Acid liquid 300mL chloroform extraction, take off a layer chloroform layer, and is standing with 300mL 2-4%NaOH extraction, gets the upper strata alkaline solution, with 10-20% hydrochloric acid, transfers pH=7-9, and standing, lower floor's chloroform layer is sample liquid.Sample liquid is concentrated into 2mL, adopts and prepares type GF
254Silica-gel plate, micropipet pipette 2 μ L sample liquid points in the thin plate positon of near bottom, and hair dryer dries up.To put excellent thin plate and be placed in airtight exhibition cylinder, ascending development, hair dryer dries up.Take chloroform: methyl alcohol: the volume ratio of ammoniacal liquor, as the mixed solution of 65: 1: 1 as developping agent launches,, with the iodine vapor colour developing, scrapes the silica gel at position, nucin place, 80 ℃ of-100 ℃ of Soxhlet extractings, and vacuum-drying is red nucin crude product.With C
18Silica gel with methyl alcohol (chromatographic grade) fully soak degassed after, settling methods is dressed up the post of 500 * 25mm.After fully washing out impurity with methyl alcohol, then use 20% acetonitrile solution balance.Will be through the crude product of Preparative TLC chromatography preliminary purification, be dissolved in upper prop after 2ml methyl alcohol, and with 20-40% acetonitrile wash-out, chromatography process carries out at normal temperatures and pressures.Collect nucin crude product elutriant, 20ml/ part, collect 30 parts, treats that HPLC measures each section stream part purity.Fractional Collections nucin crude product elutriant, (the moving phase condition is acetonitrile: water=15: 85 (V: V) be moving phase with the HPLC detection; Detect wavelength: 260nm; Column temperature: 25 ℃), purity merges greater than 19～No. 25 streams part of 95%, and nitrogen is blown away neat solvent, obtains the nucin standard substance, and recording purity is 98.1%, and productive rate is 350 μ g/g.
Claims (1)
1. the nucin of an extraction prepares the method for nucin standard substance, it is characterized in that, the hickory nut epicarp that will dry in the shade, 50 ℃ of vacuum-dryings, pulverize, cross 60 mesh sieves, get in the 600g raw material powder that to add concentration be the ammoniacal liquor of 10-20%, mix thoroughly to moistening, the ethanol that adds again 6kg95%, a ℃ lower thermal backflow is extracted 4 times in temperature 50 C-80, each 1.5h, the centrifugal 15min of extracting solution, centrifugal rotational speed 3500r/min, merge supernatant liquor, is evaporated to the medicinal extract shape, medicinal extract, with 300mL 1-3% dissolving with hydrochloric acid, transfers pH=2-4 to obtain acid liquid, acid liquid 300mL chloroform extraction, take off a layer chloroform layer, extract standing with 300mL 2-4% NaOH, get the upper strata alkaline solution, transfer pH=7-9 with 10-20% hydrochloric acid, standing, lower floor's chloroform layer is sample liquid, sample liquid is concentrated into 2mL, employing prepares type GF254 silica-gel plate, micropipet pipettes 2 μ L sample liquid points in the thin plate positon of near bottom, hair dryer dries up, to put excellent thin plate is placed in airtight exhibition cylinder, ascending development, hair dryer dries up, take chloroform: methyl alcohol: the volume ratio of ammoniacal liquor is launched as the mixed solution of 65:1:1 as developping agent, develop the color with iodine vapor, scrape the silica gel at position, nucin place, 80 ℃ of-100 ℃ of Soxhlet extractings, vacuum-drying is red nucin crude product, with C18 silica gel with methyl alcohol fully soak degassed after, settling methods is dressed up the post of 500 * 25 mm, after fully washing out impurity with methyl alcohol, use again 20% acetonitrile solution balance, will be through the crude product of Preparative TLC chromatography preliminary purification, be dissolved in upper prop after 2ml methyl alcohol, and with 20-40% acetonitrile wash-out, chromatography process carries out at normal temperatures and pressures, collect nucin crude product elutriant, 20ml/ part, collect 30 parts, treat that HPLC measures each section stream part purity, Fractional Collections nucin crude product elutriant, HPLC is detected, the moving phase condition is acetonitrile: water=15:85(V:V) is moving phase, detect wavelength: 260nm, column temperature: 25 ℃, purity merges greater than 19～No. 25 streams part of 95%, nitrogen is blown away neat solvent, obtain the nucin standard substance, recording purity is 98.1%, and productive rate is 350 μ g/g.
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| CN104370713B (en) * | 2014-09-26 | 2016-03-02 | 浙江大学宁波理工学院 | 4-(2,3-dihydroxyl propoxy-)-8-hydroxyl-ALPHA-tetralone and synthetic method |
| CN104326889B (en) * | 2014-09-26 | 2016-09-14 | 浙江大学宁波理工学院 | Ethylene glycol bisthioglycolate-8-(4-hydroxyl-ALPHA-tetralone) ether and synthetic method |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101328114A (en) * | 2007-06-23 | 2008-12-24 | 中国科学院兰州化学物理研究所 | Method for extracting walnuts ketone from walnut green husk |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101328114A (en) * | 2007-06-23 | 2008-12-24 | 中国科学院兰州化学物理研究所 | Method for extracting walnuts ketone from walnut green husk |
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| Title |
|---|
| 山核桃外果皮中核桃酮热回流法提取的工艺条件;王晓燕等;《经济林研究》;20110315;第29卷(第1期);第85-89页,第86页左栏第7-8、29-32行、右栏第5-6行,第89页左栏第9-10行 * |
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| 王晓燕等.山核桃外果皮中核桃酮热回流法提取的工艺条件.《经济林研究》.2011,第29卷(第1期),第85-89页. |
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