CN1392128A - Process for preparing extract containing hypericin and flavon compounds - Google Patents
Process for preparing extract containing hypericin and flavon compounds Download PDFInfo
- Publication number
- CN1392128A CN1392128A CN 02134379 CN02134379A CN1392128A CN 1392128 A CN1392128 A CN 1392128A CN 02134379 CN02134379 CN 02134379 CN 02134379 A CN02134379 A CN 02134379A CN 1392128 A CN1392128 A CN 1392128A
- Authority
- CN
- China
- Prior art keywords
- hypericin
- content
- polar solvent
- extract
- package stabilizer
- 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.)
- Granted
Links
- 229940005608 hypericin Drugs 0.000 title claims abstract description 32
- PHOKTTKFQUYZPI-UHFFFAOYSA-N hypericin Natural products Cc1cc(O)c2c3C(=O)C(=Cc4c(O)c5c(O)cc(O)c6c7C(=O)C(=Cc8c(C)c1c2c(c78)c(c34)c56)O)O PHOKTTKFQUYZPI-UHFFFAOYSA-N 0.000 title claims abstract description 32
- SSKVDVBQSWQEGJ-UHFFFAOYSA-N pseudohypericin Natural products C12=C(O)C=C(O)C(C(C=3C(O)=CC(O)=C4C=33)=O)=C2C3=C2C3=C4C(C)=CC(O)=C3C(=O)C3=C(O)C=C(O)C1=C32 SSKVDVBQSWQEGJ-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 239000000284 extract Substances 0.000 title claims abstract description 25
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N flavone Chemical class O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 title claims abstract description 10
- BTXNYTINYBABQR-UHFFFAOYSA-N hypericin Chemical compound C12=C(O)C=C(O)C(C(C=3C(O)=CC(C)=C4C=33)=O)=C2C3=C2C3=C4C(C)=CC(O)=C3C(=O)C3=C(O)C=C(O)C1=C32 BTXNYTINYBABQR-UHFFFAOYSA-N 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 16
- 229930003944 flavone Natural products 0.000 claims abstract description 12
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- -1 flavone compounds Chemical class 0.000 claims abstract description 10
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 claims abstract description 9
- 150000002212 flavone derivatives Chemical class 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- MPGWGYQTRSNGDD-UHFFFAOYSA-N hypericin Chemical class OC1=CC(O)=C(C2=O)C3=C1C1C(O)=CC(=O)C(C4=O)=C1C1=C3C3=C2C(O)=CC(C)=C3C2=C1C4=C(O)C=C2C MPGWGYQTRSNGDD-UHFFFAOYSA-N 0.000 claims description 42
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 229930003935 flavonoid Natural products 0.000 claims description 16
- 235000017173 flavonoids Nutrition 0.000 claims description 16
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 15
- 239000003381 stabilizer Substances 0.000 claims description 15
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- 239000000203 mixture Substances 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 150000002215 flavonoids Chemical class 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
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- 238000001556 precipitation Methods 0.000 claims description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 2
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 1
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- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
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- NQJGJBLOXXIGHL-UHFFFAOYSA-N podocarpusflavone A Natural products COc1ccc(cc1)C2=CC(=O)c3c(O)cc(O)c(c3O2)c4cc(ccc4O)C5=COc6cc(O)cc(O)c6C5=O NQJGJBLOXXIGHL-UHFFFAOYSA-N 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- OVSQVDMCBVZWGM-QSOFNFLRSA-N quercetin 3-O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OVSQVDMCBVZWGM-QSOFNFLRSA-N 0.000 description 1
- OEKUVLQNKPXSOY-UHFFFAOYSA-N quercetin 3-O-beta-D-glucopyranosyl(1->3)-alpha-L-rhamnopyranosyl(1->6)-beta-d-galactopyranoside Natural products OC1C(O)C(C(O)C)OC1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OEKUVLQNKPXSOY-UHFFFAOYSA-N 0.000 description 1
- QPHXPNUXTNHJOF-UHFFFAOYSA-N quercetin-7-O-beta-L-rhamnopyranoside Natural products OC1C(O)C(O)C(C)OC1OC1=CC(O)=C2C(=O)C(O)=C(C=3C=C(O)C(O)=CC=3)OC2=C1 QPHXPNUXTNHJOF-UHFFFAOYSA-N 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000009871 tenuigenin Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002137 ultrasound extraction Methods 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The present invention relates to the preparation process of extract containing hypericin and flavone compounds. The technological process includes extraction with polar organic solvent, biphase extraction and acid precipitation and through the simple process the extract containing total effective component not less than 50%, hypericin of 2-4 % and general flavone up to 50-90 % may be obtained. In the technological process, composite stabilizer is used, so that the extracted product may be maintained stably.
Description
Technical field
The present invention relates to a kind of preparation method of extract that is rich in hypericin class and flavonoid compound.
Background technology
Hypericin (Hypericin) is one of antidepressant effective constituent in the Hypericaceae plant Herba Hyperici Monogyni, at first is used widely in the antidepressant field.In addition, antiviral exsomatize and experiment made on the living shows that hypericin can suppress HIV (human immunodeficiency virus) (HIV) and some other retroviruss.As: to herpes simplex virus type 1,2 types (HSV-1, HSV-2), parainfluenza virus, vaccinia virus, bleb Stomatovirus and human macrophage virus have restraining effect.Hypericin has therapeutic action to infecting the Friend leukosis virus in the mouse body.The antitumor action of hypericin has also caused scientist's close attention, and hypericin can directly cause cancer cell-apoptosis, and is attended by cytochrome C and is discharged to tenuigenin by plastosome.
Hypericin (Hypericin) is one of antidepressant effective constituent in the Hypericaceae plant Herba Hyperici Monogyni, the plant origin of hypericin extract mainly is a hypericum, comprise Herba Hyperici perforati Hypericum perforatum L., the Herba Hyperici Erecti H.lianzhouense of Lianzhou City, Herba hyperici attenuati H.attenuatum, Herba Hyperici Erecti H.erectum, the southern regions of the Yunnan Province Radix Hyperici Monogyni (Herba Hyperici Monogyni) Hypericum austroyunnanicum, etc.
Hypericin is the dianthrone class, promptly 4,4 ', 5,5 ', 7, and 7 '-hexahydroxy--2,2 '-dimethyl-meta benzo dianthrone.Molecular formula is C
30H
16O
8, molecular weight is 504.43.Black-and-blue needle crystal (pyridine-contain HCl methyl alcohol), 320 ℃ of fusing points (decomposition) are soluble in pyridine or other organic amines and are orange red and fluorescence redly, are insoluble to most organic solvents, dissolve in the alkaline aqueous solution.The solution that takes on a red color when being lower than pH11.5 is green solution and fluorescence redly when being higher than pH11.5.To light, oxygen, thermally labile.Its chemical structure is as follows:
Hypericin (Hypericin) chemical structure
Increasing pharmacological experiments shows that the hypericin class is not unique activeconstituents of Herba Hyperici perforati antidepressant effect, and its contained flavonoid also has tangible antidepressant activity.Flavonoid content is 9.25% in the Herba Hyperici perforati, how to exist with the glucoside form, mainly comprises flavonol glucoside, flavonol, biflavone, pycnogenols and xanthone class.The flavonol glucoside has Hyperoside (hyperoside), rutin (rutin), thujin (quercitrin), trifoliin (isoquercitrin), flavonol has Quercetin (quercetin) and bisflavones, as Oman's holder flavones (amentoflavone) and I3, II8-biapigenin.Hyperoside wherein, trifoliin and campherol have been proved to be antidepressant activity in the tangible monoamine oxidase restraining effect of external demonstration.Flavonoid does not especially contain the flavonoid of 3-OH, can with Benzodiazepine (benzodiazepin) receptors bind, infer that the flavonoid in the Herba Hyperici perforati also plays a role by this way.Find two kinds of dimeric flavones compound: I3 in the Herba Hyperici perforati, and II8-Biapigenin (0.1-0.5%) and arnentoflavone (I3 ', II8-Biapigenin, 0.01-0.05%), they have the maincenter sedative activity.Arnentoflavone combines with the brain benzodiazepine receptors external, display part agonist effect, and its avidity is similar to diazepam (diazepam).Xanthone is the typical composition of guttiferae plant, 1,3,6, and 7-tetrahydroxy xanthone can 99% inhibition MAO-A in the concentration of 95 μ mol/L.In addition, flavones ingredient also may work by increasing intravital enkephalin content.
The preparation method of existing Herba Hyperici perforati extract has multiple, the extracting method that with ethanol is solvent is the most commonly used, the shortcoming of this method is, the content of hypericin class and flavonoid is low in the extract, and in the raw material content of hypericin with the place of production, kind, the difference of gathering the phase has very big-difference (0.01-0.06%) again, is difficult to obtain qualified product sometimes.With the extracting method of sodium hydroxide solution, although have with low costly, technology is simple, and advantages such as environmental protection have very big difference with the kind of the resulting extract ingredient of this extracting method and content and ethanol extraction, and its drug effect waits further checking.Also have ultrasonic extraction in addition, add antioxidant method or the like, himself advantage is respectively arranged, but they having a common shortcoming, is exactly the content too low (0.2-0.6%) of hypericin, and major part is an invalid components.
Summary of the invention
The purpose of this invention is to provide a kind of preparation technology who contains the stable extract of hypericin class and flavonoid compound, the content of hypericin class and flavonoid reaches 2-4%wt and 50-90%wt respectively in the resulting extract, and can be used as with the Herba Hyperici perforati is the medicinal preparations of raw material and the raw materials for production of functional food.
The present invention utilizes the solublization of other compositions in the Herba Hyperici perforati, with organic solvent hypericin is extracted in medicinal material, has solved the very little and problem that is difficult to extract of hypericin solubleness in organic solvent.Simultaneously, utilize hypericin class and flavonoid all to contain phenolic hydroxyl group, have this character of certain acidity, by regulating pH its precipitation is separated out, thereby its content in extract is further improved.
The concrete steps of the inventive method are as follows:
(1) gets hypericum Herba Hyperici perforati Hypericum perforatum L. or contain other plant of hypericin, each polar solvent that contains the 0.1-5% one package stabilizer with 4-10 times of crude drug amount, under the protection of room temperature and filling with inert gas lixiviate 12-48 hour, lixiviate 2-4 time, or reflux under the filling with inert gas protection, extracted 2-5 hour; Said polar organic solvent is alcohols, ketone, alcohol-water mixture or ketone water mixture; Said alcohols is ethanol preferably, and ketone is acetone preferably, and alcohol-water mixture is 60% above ethanol preferably, and the ketone water mixture is 60% above acetone preferably; Said one package stabilizer be vitamins C or derivatives thereof and organic acid by 5: 1-50: the mixture of 1 weight ratio; Organic acid in the one package stabilizer can be in citric acid, phenylformic acid, the tartrate any or they combination with arbitrary proportion; Said rare gas element can be nitrogen, argon gas or carbonic acid gas;
(2) the gained extracting solution adds water to water content 20-60%, is non-polar solvent extraction 1-3 time of 8-16 times of crude drug amount with cumulative volume; Used non-polar solvent is ether, alkanes or cycloalkane, or they arbitrarily than mixed solvent;
(3) with extracting solution (being the polar solvent phase) the reclaim under reduced pressure organic solvent after the non-polar solvent extraction, regulate pH=0-4, room temperature or 4 ℃ left standstill 1-3 days, leach precipitation and be washed to neutrality, it is 0.1-5%wt that the adding one package stabilizer makes content, drying obtains containing the stable Herba Hyperici perforati extract of hypericin class and flavonoid compound; Said one package stabilizer is identical with step (1).
The total content of hypericin class and flavonoid is not less than 50% in the extract of gained, and wherein total hypericin content is 2-4%wt, and general flavone content is 50-90%wt.
Tlc is adopted in the discriminating of hypericin in the extract, and assay adopts ultraviolet spectrophotometry and HPLC method.
Technological operation of the present invention is easy, and the extraction object height of the existing clinical use of extract obtained middle hypericin content ratio is more than 10 times.And in leaching process and product are preserved, add one package stabilizer, can increase the stability of effective constituent such as hypericin class.
Embodiment
The invention will be further described by the following examples.
Embodiment 1:
Get Herba Hyperici perforati medicinal powder 1100g, ethanol lixiviate 3 times, each 6600ml, each 1 day, merge alcohol extract and concentrating under reduced pressure, get black solid 21g, hypericin content 0.32%.
Embodiment 2:
Get Herba Hyperici perforati medicinal powder 1100g, acetone extraction 3 times, each 6600ml, lixiviate 3 times, each 1 day, merge acetone extraction liquid and concentrating under reduced pressure, get black solid 12g, hypericin content 0.6%.
Embodiment 3:
Herba Hyperici perforati powder 400g, acetone extraction 3 times, each 2500ml each 1 day, merges acetone extraction liquid and adds 4000ml distilled water, again with petroleum ether extraction 3 times, each 1200ml merges the acetone water layer, is evaporated to 1500ml under 60 ℃, obtained aqueous solution is regulated pH=0 with hydrochloric acid, and 4 ℃ left standstill 72 hours.Centrifugal, will precipitate lyophilize and obtain brown extract 8.40g, hypericin content 2.3%, general flavone content (in rutin) 64.2%.
Embodiment 4:
Herba Hyperici perforati powder 400g, 3 times (contain 2% one package stabilizer, stablizer consists of V to acetone extraction
C: citric acid=20: 1), logical nitrogen protection, each 2500ml, each 1 day; vat liquor adds 4000ml water, and with extracted with diethyl ether 3 times, each 1200ml merges the acetone water again; be evaporated to 1000ml under 60 ℃, the aqueous solution 10% hydrochloric acid is regulated pH=4, and 4 ℃ left standstill 48 hours.Centrifugal, will precipitate lyophilize and get sorrel extract 5.8g, hypericin content 3.8%, general flavone content (in rutin) 85.3%.
Embodiment 5:
Herba Hyperici perforati powder 400g, acetone reflux, and 5 times (contain 0.5% one package stabilizer, stablizer consists of V
C: phenylformic acid=40: 1), logical nitrogen protection, each 1600ml, each 2 hours; vat liquor adds 4000ml water, uses n-hexane extraction 3 times, each 1200ml; be evaporated to 1200ml under 60 ℃ of the acetone waters, the aqueous solution 10% hydrochloric acid is regulated pH=2, and 4 ℃ left standstill 48 hours.Centrifugal, will precipitate lyophilize and get sorrel extract 6.0g, hypericin content 3.5%, general flavone content (in rutin) 70.6%.
Embodiment 6:
Herba Hyperici perforati powder 400g, 70% aqueous acetone solution reflux, and 2 times (contain 3% one package stabilizer, stablizer consists of V
CCetylate: citric acid=10: 1), logical nitrogen protection, each 4000ml, each 4 hours, with hexanaphthene extraction 2 times, be evaporated to 1000ml under the each 3000ml, 60 ℃ of acetone waters, the aqueous solution 10% hydrochloric acid is regulated pH=3, room temperature left standstill 72 hours.Centrifugal, will precipitate lyophilize and get sorrel extract 7.6g, hypericin content 2.5%, general flavone content (in rutin) 58.5%.
Embodiment 7:
Herba Hyperici perforati powder 400g, 3 times (contain 2% one package stabilizer, stablizer consists of V to 80% alcohol reflux
C: citric acid=5: 1), logical nitrogen protection, each 2500ml, each 3 hours, with petroleum ether extraction 3 times, be evaporated to 1500ml under the each 1500ml, 60 ℃ of ethanol waters, the aqueous solution 10% hydrochloric acid is regulated pH=3, and room temperature left standstill 72 hours.Centrifugal, will precipitate lyophilize and get sorrel extract 9.1g, hypericin content 2.1%, general flavone content (in rutin) 50.2%.
Claims (6)
1. preparation method who contains the stable extract of hypericin class and flavonoid compound, its concrete steps are:
(1) gets hypericum Herba Hyperici perforati or contain other plant of hypericin, each polar solvent that contains the 0.1-5% one package stabilizer with 4-10 times of crude drug amount, under the protection of room temperature and filling with inert gas lixiviate 12-48 hour, lixiviate 2-4 time, or reflux under the filling with inert gas protection, extracted 2-5 hour; Said polar solvent is alcohols, ketone, alcohol-water mixture or ketone water mixture; Said one package stabilizer be vitamins C or derivatives thereof and organic acid by 5: 1-50: the mixture of 1 weight ratio;
(2) the gained extracting solution adds water to water content 20-60%, is non-polar solvent extraction 1-3 time of 8-16 times of crude drug amount with cumulative volume; Used non-polar solvent is ether, alkanes or cycloalkane, or they arbitrarily than mixed solvent;
(3) with the extracting solution reclaim under reduced pressure organic solvent after the non-polar solvent extraction, regulate pH=0-4, room temperature or 4 ℃ left standstill 1-3 days, leach precipitation and be washed to neutrality, it is 0.1-5%wt that the adding one package stabilizer makes content, drying obtains containing the stable Herba Hyperici perforati extract of hypericin class and flavonoid compound; Said one package stabilizer is identical with step (1).
2. in accordance with the method for claim 1, it is characterized in that said alcohols is an ethanol, ketone is an acetone, and alcohol-water mixture is 60% above ethanol, and the ketone water mixture is 60% above acetone.
3. in accordance with the method for claim 1, it is characterized in that the alkanes in the said non-polar solvent is sherwood oil, Skellysolve A, normal hexane or normal heptane, cycloalkane is pentamethylene or hexanaphthene.
4. in accordance with the method for claim 1, it is characterized in that organic acid in the said one package stabilizer be in citric acid, phenylformic acid, the tartrate any or they with the combination of arbitrary proportion.
5. in accordance with the method for claim 1, it is characterized in that said rare gas element is nitrogen, argon gas or carbonic acid gas.
6. according to the described method of one of claim 1 to 5, it is characterized in that the total content of hypericin class and flavonoid is not less than 50% in the extract of gained, wherein total hypericin content is 2-4%wt, general flavone content is 50-90%wt.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103462841A (en) * | 2013-09-06 | 2013-12-25 | 广州立白企业集团有限公司 | Toothpaste containing saussurea involucrate component |
| CN106349307A (en) * | 2016-07-29 | 2017-01-25 | 安徽徽王农业有限公司 | Stabilizer for extracting blueberry flavonoid and preparation method thereof |
| CN106668088A (en) * | 2017-02-08 | 2017-05-17 | 内蒙古昶辉生物科技股份有限公司 | Preparation method of hyperforin perforatum extract |
| CN116712476A (en) * | 2023-06-20 | 2023-09-08 | 陕西嘉禾生物科技股份有限公司 | Hypericum perforatum extract and preparation method thereof |
-
2002
- 2002-07-18 CN CN 02134379 patent/CN1215032C/en not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103462841A (en) * | 2013-09-06 | 2013-12-25 | 广州立白企业集团有限公司 | Toothpaste containing saussurea involucrate component |
| CN103462841B (en) * | 2013-09-06 | 2015-06-10 | 广州立白企业集团有限公司 | Toothpaste containing saussurea involucrate component |
| CN106349307A (en) * | 2016-07-29 | 2017-01-25 | 安徽徽王农业有限公司 | Stabilizer for extracting blueberry flavonoid and preparation method thereof |
| CN106668088A (en) * | 2017-02-08 | 2017-05-17 | 内蒙古昶辉生物科技股份有限公司 | Preparation method of hyperforin perforatum extract |
| CN116712476A (en) * | 2023-06-20 | 2023-09-08 | 陕西嘉禾生物科技股份有限公司 | Hypericum perforatum extract and preparation method thereof |
| CN116712476B (en) * | 2023-06-20 | 2024-05-31 | 陕西嘉禾生物科技股份有限公司 | Hypericum perforatum extract and preparation method thereof |
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Assignee: Shenzhen AESTHETIC Biological Technology Co., Ltd. Assignor: Sun Yat-sen University Contract record no.: 2011440000549 Denomination of invention: Process for preparing extract containing hypericin and flavon compounds Granted publication date: 20050817 License type: Exclusive License Open date: 20030122 Record date: 20110621 |
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