CN105693494A - Process for extracting and purifying hypericin from hypericum perforatum - Google Patents
Process for extracting and purifying hypericin from hypericum perforatum Download PDFInfo
- Publication number
- CN105693494A CN105693494A CN201610111414.0A CN201610111414A CN105693494A CN 105693494 A CN105693494 A CN 105693494A CN 201610111414 A CN201610111414 A CN 201610111414A CN 105693494 A CN105693494 A CN 105693494A
- Authority
- CN
- China
- Prior art keywords
- hypericin
- herba hyperici
- hyperici perforati
- technique
- extraction
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/10—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a process for extracting and purifying hypericin from hypericum perforatum. At present, high-purity hypericin medicinal components cannot be extracted out through most of studies on the hypericin extraction process. The process is characterized in that according to the polyphenol characteristics of hypericin, an original extraction process route is improved through an acid and alkali extraction method, and the purity of objects to be separated is effectively improved. Finally, the high-purity hypericin is prepared. The macroporous resin separation technology, the column chromatography on silica gel technology and the like are comprehensively utilized, and a basis and a simple and feasible industrial route are provided for fully utilizing hypericum perforatum resources in industrial production.
Description
Technical field
The present invention relates to technical field of extraction of Chinese traditional medicine, particularly relate to a kind of technique of extraction purification hypericin from Herba Hyperici perforati。
Background technology
It is Guttiferae Hypericum herbaceos perennial that Herba Hyperici perforati (HypericumPerforatumL.) has another name called Herba Hyperici perforati, and Herba Hyperici perforati extract and preparation are one of best-selling plant amedica in North America and Europe。It is few that research shows that this natural drug has untoward reaction compared with synthetic drug, and short term security is high, the features such as patient compliance is good。Along with the upsurge of domestic and international back to nature grows to even greater heights, the drawback of chemical drugs displays day by day, and natural drug market increases swift and violent。On world pharmaceutical market, natural drug has accounted for the share of 30%, and quickly increases with the amplitude of annual 15-20%。The modernization of Chinese medicine is the inexorable trend of social development, including the Chinese medicine modernization of industry, medicinal plant farming modernization and Chinese medicine business modernization。It is a systematic engineering of business, is faced with many opportunities and challenges。Want to realize the modernization of Chinese medicine and need to have breakthrough in three guardian techniques: the modernization of pharmacological effect tracer technique；The modernization of Quality Control Technology；Extract the modernization of (particularly selective extraction) technology of separation。Chinese medicine ingredient is sufficiently complex, existing effective ingredient, has again toxic component and invalid components。For improving the therapeutic effect of Chinese medicine, lower toxic and side effects, improve the inherent quality of Chinese medicine preparation, select rational extraction process extremely important。
Herba Hyperici perforati contains multiple chemical composition, mainly has phloroglucinol derivatives, benzo dianthrone class, tannins, flavonoid etc.。Wherein benzo dianthrone class, flavonoid, phloroglucinol derivatives is considered as the main active of depression in Herba Hyperici perforati。
(1) benzo dianthrone class
Benzo dianthrone class mainly includes pseudohypericin (pseudohypericin), hypericin (hypericin) and some precursor substances, such as former pseudohypericin (protopseudohypericin), former hypericin (protohypericin)。Wherein pseudohypericin and hypericin are the characteristic components of hypericum, are primarily present in bud and spend, content in Herba Hyperici perforati is generally ten thousand/and several。Wherein the content of pseudohypericin is 2-4 times of hypericin。The content of Hypericin in Hypericum perforatum L is very low, and on international market, regulation Hypericin Content in Extract of Hypericum content cannot be below 0.3%。
(2) phloroglucinol derivatives
Phloroglucinol derivatives material widely exists in Garcinia maingayii。Herba Hyperici perforati mainly contains Adhyperforin. (adhyperforin) and hyperforine (hyperforin)。
(3) flavonoid
Hypericin is considered as the depressed active main active of Herba Hyperici perforati always, but there are some researches show in recent years, and Plant crude extract is better than the antidepressant effect of pure hypericin。Studies have reported that, Flavonoid substances also has antidepressant effect。And both at home and abroad the research of Herba Hyperici perforati is mostly focused on hypericin at present。Flavonoid content in Herba Hyperici perforati is significantly high, has reached 9.25% in herb, and much more stable than hypericin, is Protected from Heat without lucifuge, has good DEVELOPMENT PROSPECT。The main Flavonoid substances of Herba Hyperici perforati has rutin (rutin), Quercetin (quercetin), Quercitroside (quercitrin), hyperins (hyperin) etc., have antiinflammatory, antiviral, the effects such as antidiarrheal, astringing to arrest bleeding, great exploitation potential。
(4) tannins
Tannins mainly includes poly-proanthocyanidin (procuanidin), its precursor catechin (catechin) and epicatechin (epicatechin)。
Hypericin molecular structural formula is as follows:
In order to better develop this natural resources of Chinese medicinal materials of Herba Hyperici perforati, intend the multiple quantification and qualification determination techniques of integrated use, Chinese medicine extraction separating and purifying technology and modernization chromatographic technique, active component dianthracene ketone compounds in research Herba Hyperici perforati: hypericin (hypericin), pseudohypericin (pseudohypericin), former hypericin (pro-tohypericin), ring pseudohypericin (cyclopseudohypericin), the process for extracting, separating and purifying of nor-basic ring pseudohypericin (desmethylcyclopseudohypericin), and correlated quality analysis method, simple in order to set up, stable preparation technology, prepare the content hypericin series products more than 8-9%, in order to improve the bioavailability of medicine, strengthen the safety of medication, at present, domestic more about hypericin research。But most researchs all fail to extract high-purity hypericin class active ingredient。
Summary of the invention
The invention provides a kind of technique of extraction purification hypericin from Herba Hyperici perforati。
The present invention adopts the following technical scheme that
The specifically comprising the following steps that of the technique of extraction purification hypericin from Herba Hyperici perforati of the present invention
(1) being pulverized by Herba Hyperici perforati, obtain fine powder, be subsequently adding methanol, liquid-solid ratio is 30-50:1, then carries out ultrasonic lixiviate, lixiviate 3-5 time, each 30-90min, is then evaporated to the liquid obtained without alcohol taste, obtains Herba Hyperici perforati extracting solution；
(2) the extracting solution AB-8 macroporous adsorbent resin of step (1) is adsorbed, then with ethanol elution, concentrate eluant, is evaporated to without alcohol taste, and adding volume ratio is the extraction into ethyl acetate of 1:0.5-2, ethyl acetate is dried mutually, reclaim ethyl acetate, obtain extractum, then refine through silica gel column chromatography, obtain hypericin crude product, finally use half preparative high-performance liquid chromatographic to refine further and obtain hypericin sterling。
In step (1), after Herba Hyperici perforati pulverizing, the particle diameter of fine powder is be more than or equal to 80 orders。
In step (1), the volumetric concentration adding methanol is 60%, methanol: water (V/V)=3:2。
In step (1), it is preferable that liquid-solid ratio is 40:1, then carry out ultrasonic lixiviate, lixiviate 4 times, each 60min。
In step (2), the volumetric concentration of eluting ethanol is 60%, eluting 4 times。
In step (2), it is preferable that adding volume ratio is the extraction into ethyl acetate of 1:1。
In step (2), chloroform, methanol and formic acid that silica gel column chromatography is refining is 8:2:0.25 with volume ratio are for eluant。
In step (2), the condition of half preparative high-performance liquid chromatographic is: flow velocity 4ml/min, 2ml/ time, wavelength 254nm, column temperature 30 DEG C, mobile phase V (acetonitrile): V (0.1%H3PO4)=16:84。
The positive effect of the present invention is as follows:
Because all failing to extract high-purity hypericin class active ingredient to researchs most in hypericin Study on extraction at present。Innovation of the present invention is in that according to the polyphenol characteristic of hypericin own, adopts acid, alkali extraction that former extraction process route is improved, is effectively improved material to be separated purity。Final realization prepares high-purity hypericin。
At present the research of Herba Hyperici perforati is concentrated mainly on hypericin composition, because of Hypericin in Hypericum perforatum L content relatively low (less than 1%), integrated use macroporous resin isolation technics of the present invention, silica gel column chromatography technology etc., for utilizing Herba Hyperici perforati resource to provide the commercial routes of foundation and simple possible more fully in commercial production。
Detailed description of the invention
The following examples are describing in further detail the present invention。
Embodiment 1
The specifically comprising the following steps that of the technique of extraction purification hypericin from Herba Hyperici perforati of the present invention
(1) Herba Hyperici perforati is pulverized, obtaining fine powder, be subsequently adding methanol, liquid-solid ratio is 30:1, then ultrasonic lixiviate is carried out, lixiviate 3 times, each 90min, then the liquid obtained is evaporated to without alcohol taste, obtain Herba Hyperici perforati extracting solution, in extracting solution, Determination of Hypericin from Extraction is 0.325%, and extraction ratio is 90%, and ultimate yield is 0.063%；
(2) the extracting solution AB-8 macroporous adsorbent resin of step (1) is adsorbed, then with ethanol elution, concentrate eluant, it is evaporated to without alcohol taste, adding volume ratio is the extraction into ethyl acetate of 1:0.5, ethyl acetate is dried mutually, reclaims ethyl acetate, obtain extractum, then refine through silica gel column chromatography, obtaining hypericin crude product, finally use half preparative high-performance liquid chromatographic to refine further and obtain hypericin sterling, hypericin sterling content is 8.5%。
In step (1), after Herba Hyperici perforati pulverizing, the particle diameter of fine powder is be more than or equal to 80 orders。
In step (1), the volumetric concentration adding methanol is 60%。
In step (2), the volumetric concentration of eluting ethanol is 60%, eluting 4 times。
In step (2), chloroform, methanol and formic acid that silica gel column chromatography is refining is 8:2:0.25 with volume ratio are for eluant。
In step (2), the condition of half preparative high-performance liquid chromatographic is: flow velocity 4ml/min, 2ml/ time, wavelength 254nm, column temperature 30 DEG C, mobile phase V (acetonitrile): V (0.1%H3PO4)=16:84。
Embodiment 2
The specifically comprising the following steps that of the technique of extraction purification hypericin from Herba Hyperici perforati of the present invention
(1) Herba Hyperici perforati is pulverized, obtaining fine powder, be subsequently adding methanol, liquid-solid ratio is 50:1, then ultrasonic lixiviate is carried out, lixiviate 5 times, each 30min, then the liquid obtained is evaporated to without alcohol taste, obtain Herba Hyperici perforati extracting solution, in extracting solution, Determination of Hypericin from Extraction is 0.328%, and extraction ratio is 91%, and ultimate yield is 0.066%；
(2) the extracting solution AB-8 macroporous adsorbent resin of step (1) is adsorbed, then with ethanol elution, concentrate eluant, it is evaporated to without alcohol taste, adding volume ratio is the extraction into ethyl acetate of 1:2, ethyl acetate is dried mutually, reclaims ethyl acetate, obtain extractum, then refine through silica gel column chromatography, obtaining hypericin crude product, finally use half preparative high-performance liquid chromatographic to refine further and obtain hypericin sterling, hypericin sterling content is 9%。
In step (1), after Herba Hyperici perforati pulverizing, the particle diameter of fine powder is be more than or equal to 80 orders。
In step (1), the volumetric concentration adding methanol is 60%。
In step (2), the volumetric concentration of eluting ethanol is 60%, eluting 4 times。
In step (2), chloroform, methanol and formic acid that silica gel column chromatography is refining is 8:2:0.25 with volume ratio are for eluant。
In step (2), the condition of half preparative high-performance liquid chromatographic is: flow velocity 4ml/min, 2ml/ time, wavelength 254nm, column temperature 30 DEG C, mobile phase V (acetonitrile): V (0.1%H3PO4)=16:84。
Embodiment 3
The specifically comprising the following steps that of the technique of extraction purification hypericin from Herba Hyperici perforati of the present invention
(1) Herba Hyperici perforati is pulverized, obtaining fine powder, be subsequently adding methanol, liquid-solid ratio is 40:1, then ultrasonic lixiviate is carried out, lixiviate 4 times, each 60min, then the liquid obtained is evaporated to without alcohol taste, obtain Herba Hyperici perforati extracting solution, in extracting solution, Determination of Hypericin from Extraction is 0.335%, and extraction ratio is 92%, and ultimate yield is 0.069%；
(2) the extracting solution AB-8 macroporous adsorbent resin of step (1) is adsorbed, then with ethanol elution, concentrate eluant, it is evaporated to without alcohol taste, adding volume ratio is the extraction into ethyl acetate of 1:1, ethyl acetate is dried mutually, reclaims ethyl acetate, obtain extractum, then refine through silica gel column chromatography, obtaining hypericin crude product, finally use half preparative high-performance liquid chromatographic to refine further and obtain hypericin sterling, hypericin sterling content is 9%。
In step (1), after Herba Hyperici perforati pulverizing, the particle diameter of fine powder is be more than or equal to 80 orders。
In step (1), the volumetric concentration adding methanol is 60%。
In step (2), the volumetric concentration of eluting ethanol is 60%, eluting 4 times。
In step (2), chloroform, methanol and formic acid that silica gel column chromatography is refining is 8:2:0.25 with volume ratio are for eluant。
In step (2), the condition of half preparative high-performance liquid chromatographic is: flow velocity 4ml/min, 2ml/ time, wavelength 254nm, column temperature 30 DEG C, mobile phase V (acetonitrile): V (0.1%H3PO4)=16:84。
Although an embodiment of the present invention has been shown and described, for the ordinary skill in the art, being appreciated that and these embodiments can be carried out multiple change, amendment, replacement and modification without departing from the principles and spirit of the present invention, the scope of the present invention be defined by the appended。
Claims (8)
1. the technique of extraction purification hypericin from Herba Hyperici perforati, it is characterised in that: specifically comprising the following steps that of described technique
(1) being pulverized by Herba Hyperici perforati, obtain fine powder, be subsequently adding methanol, liquid-solid ratio is 30-50:1, then carries out ultrasonic lixiviate, lixiviate 3-5 time, each 30-90min, is then evaporated to the liquid obtained without alcohol taste, obtains Herba Hyperici perforati extracting solution；
(2) the extracting solution AB-8 macroporous adsorbent resin of step (1) is adsorbed, then with ethanol elution, concentrate eluant, is evaporated to without alcohol taste, and adding volume ratio is the extraction into ethyl acetate of 1:0.5-2, ethyl acetate is dried mutually, reclaim ethyl acetate, obtain extractum, then refine through silica gel column chromatography, obtain hypericin crude product, finally use half preparative high-performance liquid chromatographic to refine further and obtain hypericin sterling。
2. the technique of extraction purification hypericin from Herba Hyperici perforati as claimed in claim 1, it is characterised in that: in step (1), after Herba Hyperici perforati pulverizing, the particle diameter of fine powder is be more than or equal to 80 orders。
3. the technique of extraction purification hypericin from Herba Hyperici perforati as claimed in claim 1, it is characterised in that: in step (1), the volumetric concentration adding methanol is 60%。
4. the technique of extraction purification hypericin from Herba Hyperici perforati as claimed in claim 1, it is characterised in that: in step (1), liquid-solid ratio is 40:1, then carries out ultrasonic lixiviate, lixiviate 4 times, each 60min。
5. the technique of extraction purification hypericin from Herba Hyperici perforati as claimed in claim 1, it is characterised in that: in step (2), the volumetric concentration of eluting ethanol is 60%, eluting 4 times。
6. the technique of extraction purification hypericin from Herba Hyperici perforati as claimed in claim 1, it is characterised in that: in step (2), adding volume ratio is the extraction into ethyl acetate of 1:1。
7. the technique of extraction purification hypericin from Herba Hyperici perforati as claimed in claim 1, it is characterised in that: in step (2), chloroform, methanol and formic acid that silica gel column chromatography is refining is 8:2:0.25 with volume ratio are for eluant。
8. the technique of extraction purification hypericin from Herba Hyperici perforati as claimed in claim 1, it is characterized in that: in step (2), the condition of half preparative high-performance liquid chromatographic is: flow velocity 4ml/min, 2ml/ time, wavelength 254nm, column temperature 30 DEG C, mobile phase V (acetonitrile): V (0.1%H3PO4)=16:84。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610111414.0A CN105693494A (en) | 2016-02-27 | 2016-02-27 | Process for extracting and purifying hypericin from hypericum perforatum |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610111414.0A CN105693494A (en) | 2016-02-27 | 2016-02-27 | Process for extracting and purifying hypericin from hypericum perforatum |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105693494A true CN105693494A (en) | 2016-06-22 |
Family
ID=56223526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610111414.0A Pending CN105693494A (en) | 2016-02-27 | 2016-02-27 | Process for extracting and purifying hypericin from hypericum perforatum |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105693494A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109704939A (en) * | 2019-02-23 | 2019-05-03 | 重庆工商大学 | A method of preparing high-purity hypericin |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1850766A (en) * | 2006-04-29 | 2006-10-25 | 中国农业科学院兰州畜牧与兽药研究所 | Method for extracting hypericin |
| CN1951895A (en) * | 2006-11-03 | 2007-04-25 | 深圳职业技术学院 | Process for extracting high-content hypericin from Hypericum perforatum L. |
| CN100367976C (en) * | 2004-04-21 | 2008-02-13 | 上海市中药研究所 | Hypericum perforatum extract and its preparation process |
| CN101961358A (en) * | 2010-10-13 | 2011-02-02 | 浙江大学城市学院 | Preparation method of hypericum perforatum extractive |
-
2016
- 2016-02-27 CN CN201610111414.0A patent/CN105693494A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100367976C (en) * | 2004-04-21 | 2008-02-13 | 上海市中药研究所 | Hypericum perforatum extract and its preparation process |
| CN1850766A (en) * | 2006-04-29 | 2006-10-25 | 中国农业科学院兰州畜牧与兽药研究所 | Method for extracting hypericin |
| CN1951895A (en) * | 2006-11-03 | 2007-04-25 | 深圳职业技术学院 | Process for extracting high-content hypericin from Hypericum perforatum L. |
| CN101961358A (en) * | 2010-10-13 | 2011-02-02 | 浙江大学城市学院 | Preparation method of hypericum perforatum extractive |
Non-Patent Citations (2)
| Title |
|---|
| 程力惠等: "贯叶连翘中金丝桃素提取分离工艺的研究", 《时珍国医国药》 * |
| 邢桂珍: "金丝桃素的提取与化学合成工艺的研究", 《中国优秀硕士学位论文全文数据库》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109704939A (en) * | 2019-02-23 | 2019-05-03 | 重庆工商大学 | A method of preparing high-purity hypericin |
| CN109704939B (en) * | 2019-02-23 | 2021-09-17 | 重庆工商大学 | Method for preparing high-purity hypericin |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Zhang et al. | Extraction of bio-active components from Rhodiola sachalinensis under ultrahigh hydrostatic pressure | |
| CN102976909B (en) | Method for extracting and purifying 6-gingerol from ginger | |
| CN102260227B (en) | Method for separating paclitaxel and related taxane substances | |
| CN103450120A (en) | Preparation method for extracting taxol from taxus chinensis | |
| CN102241659A (en) | Purification method of alpha-mangostin | |
| CN105132172B (en) | A method of preparing tobacco orrisroot Flavonoid substances from orrisroot | |
| CN103304605B (en) | Method for preparing flavonoid glycoside and stibene glucoside type compound by separating from fenugreek | |
| CN102718774B (en) | Method for preparing artemisinin | |
| CN102731592B (en) | A kind of method extracting oleuropein and Tridemethylsciadopitysin from olive leaf | |
| CN101234147B (en) | Method of preparing total flavones of tropaeolum for injections | |
| CN108864021A (en) | A method of high-purity luteolin is prepared using zinc salt | |
| CN110092767A (en) | A method of Sync enrichment purification of paclitaxel and 10-DAB III from Chinese yew | |
| CN104382968B (en) | Extraction method of andrographolide, andrographolide pharmaceutical composition and application | |
| CN105693494A (en) | Process for extracting and purifying hypericin from hypericum perforatum | |
| CN104163754A (en) | Method for extraction and separating of high purity resveratrol from peanut root | |
| CN105646519A (en) | Method for ultrasonic aqueous solution extraction of artemisinin | |
| CN101024604B (en) | Novel dihydrochalcone compound separated and purified from drgon blood and preparation method thereof | |
| CN105198850A (en) | Method for rapidly preparing 3,5,6,7,8,3',4'-heptanmethphoxyflavone from citrus chachiensis hortorum | |
| CN103058979A (en) | Method for extracting procyanidine in ginkgo leaves | |
| CN102389456A (en) | Method for extracting isodon japonica var.galaucocalyx total diterpenoids or Glaucocalyxin A | |
| CN103613621B (en) | The preparation method of verbascoside and Isoverbascoside in spot lip Herb of Resupinate Woodbetony | |
| CN107011157A (en) | A kind of method that Arteannuic acid is extracted from the extract solution of production qinghaosu | |
| CN104910246A (en) | Cucurbitacins preparation method | |
| CN105193935A (en) | Method for preparing lindera aggregata leaf extract and application of lindera aggregata leaf extract | |
| CN102850367A (en) | Preparation method of blumealactone A |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20160622 |