CN100577677C - Caulis trachelospermi total lignans extractive, extraction method and medicine use of the active constituent thereof - Google Patents
Caulis trachelospermi total lignans extractive, extraction method and medicine use of the active constituent thereof Download PDFInfo
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- CN100577677C CN100577677C CN200510093357A CN200510093357A CN100577677C CN 100577677 C CN100577677 C CN 100577677C CN 200510093357 A CN200510093357 A CN 200510093357A CN 200510093357 A CN200510093357 A CN 200510093357A CN 100577677 C CN100577677 C CN 100577677C
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Abstract
The invention discloses a total lignans from caulis trachelospermi and extracting method, which is characterized by the following: possessing 30-90% lignans in the total lignans; fitting for preparing medicine to treat inflammation and or pain; making the lignan as inhibitor of epoxidised enzyme.
Description
Invention field
The present invention relates to extract total lignans and the extracting method thereof that obtains from Stem of confederate-jasmine, described total lignans extract contains the lignan component of 30-90 weight %.The invention still further relates to described extract and wherein effectively lignan component be used for the treatment of the purposes in the medicine of inflammation and/or pain and be used for the treatment of purposes in the medicine of other disease such as tumour, thrombus etc. in preparation in preparation as cyclooxygenase (COX) inhibitor.
Background technology
Stem of confederate-jasmine is stem and the leaf of apocynaceae plant trachelospermum jasminoide (Trachelospermum jasminoides (Lindl.)), the conventional Chinese medicine that records for Chinese Pharmacopoeia, have dispel the wind, the effect of vein relaxing, the stasis of blood of stopping blooding, disappear, be mainly used in treatment rheumatic arthritis, arthrodynia, myalgia, soreness of waist and knee joint, swelling and pain in the throat, haematemesis, traumatic hemorrhage etc. clinically.But unclear always to relieving inflammation and relaxing pain effective constituent wherein, do not see up till now about caulis trachelospermi total lignans extractive and extracting method and this extract and the wherein report of the anti-inflammatory and antalgic activity of effective constituent.
Summary of the invention
The inventor has now found that the relieving inflammation and relaxing pain effective constituent of Stem of confederate-jasmine is lignan component, and the extracting method that use to be fit to can extract from Stem of confederate-jasmine and obtains the total lignans extract of lignan component content between 30-90 weight %.Total lignans extract and main lignan component wherein have significant anti-inflammatory and antalgic activity, can be used for treating various inflammation (as rheumatic arthritis etc.) and pain (as arthrodynia etc.).And the inventor discovers that main lignan component has the tangible activity that combines with induction type cyclooxygenase (COX-2) in the total lignans.Thereby, total lignans and wherein lignan component can be used as cox-2 inhibitors and be used for the treatment of other disease such as tumour, thrombus etc.The present invention is based on above-mentioned discovery now finishes.
Therefore, first aspect of the present invention relates to a kind of extract, and it is to extract the total lignans extract obtain from Stem of confederate-jasmine, is characterised in that the lignan component that contains 30-90 weight % and contains a kind of with six kinds of compounds shown in the following formula 1-6 at least:
The essential characteristic of the reactive monomer compound that table 1 the present invention relates to
Second aspect of the present invention relates to the extracting method of described extract, and described method comprises water, acetone, C
1-4Alkyl alcohol or their mixture extract Stem of confederate-jasmine or with column chromatography, liquid liquid, liquid-solid extraction method, CO such as macroporous resin, drop adverse current
2Technology such as supercritical extraction are carried out arbitrary combination and are extracted Stem of confederate-jasmine.The above extract is to extract the total lignans extract obtain from Stem of confederate-jasmine, contains the lignan component of 30-90 weight % and contains a kind of suc as formula six kinds of compounds shown in the 1-6 at least.
The 3rd aspect of the present invention relates to and is used for anti-inflammatory and/or analgesic product or pharmaceutical composition, and it contains the total lignans extract of Stem of confederate-jasmine or the wherein composition of monomer component and their one or more pharmaceutically acceptable carriers or vehicle.Wherein said extract contains the lignan component of 30-90 weight % and contains a kind of suc as formula six kinds of compounds shown in the 1-6 at least.Shown in the formula that the is characterized as 1-6 structure and table 1 of described monomer component.
The 4th aspect of the present invention relates to the total lignans extract of Stem of confederate-jasmine or the arbitrary combination between formula 1-6 monomer component or formula 1-6 monomer component is used for the treatment of the product of inflammation and/or pain or the purposes in the medicine in preparation.Wherein said extract contains the lignan component of 30-90 weight % and contains a kind of suc as formula six kinds of compounds shown in the 1-6 at least.Shown in the formula that the is characterized as 1-6 structure and table 1 of described monomer component.
The invention still further relates to the total lignans extract of Stem of confederate-jasmine or the arbitrary composition between formula 1-6 monomer component or formula 1-6 monomer component and be used for the treatment of purposes in the medicine of except that inflammation and pain various diseases such as tumour, thrombus etc. in preparation as cyclooxygenase (COX-2 and/or COX-1) inhibitor.Wherein said extract contains the lignan component of 30-90 weight % and contains a kind of suc as formula six kinds of compounds shown in the 1-6 at least.Shown in the formula that the is characterized as 1-6 structure and table 1 of described monomer component.
According to the present invention, term C
1-4Alkyl alcohol says it can is methyl alcohol, ethanol, propyl alcohol, Virahol, butanols, isopropylcarbinol or the trimethyl carbinol for example.
According to the present invention, carrier is pharmacy field pharmaceutical excipient or a pharmaceutical excipient commonly used in the pharmaceutical composition of the present invention, as medicinal additive, thinner or disintegrating agent.
According to the present invention, product described in the present invention is meant not the product as medicine, as functional foodstuff or protective foods.
According to the present invention, total lignans can be by following qualitative and quantitative assay in the Stem of confederate-jasmine of the present invention lignanoid general extractive:
(-) is qualitative
The thin layer detection method: the extract that takes a morsel is made into the solution of 0.1mg/ml with methyl alcohol, this solution takes a morsel point sample on silica gel thin-layer plate, the standardized solution of getting trachelospermum jasminoide aglycon and nortracheloside unit compares, parallel point sample is on same silicon thin layer plate, use chloroform: methyl alcohol (15: 1) launches, with iodine or the colour developing of 5% ethanol solution of sulfuric acid, sample solution should have and standard substance R
fBe worth identical spot.
(2) quantitative
High performance liquid chromatography:
1. the configuration of standard solution: standard substance nortracheloside (1), tracheloside (2), nortracheloside unit (3), trachelospermum jasminoide aglycon (5) and each 10mg of aretigenin (6) of accurately taking by weighing dry constant weight, with the chromatogram dissolve with methanol and be settled to 10ml, obtain the standard solution that concentration is 1mg/ml respectively.
2. chromatographic condition: NUCLEODUR C
18Post (4.6 * 250mm, 5 μ m); Moving phase CH
3CN-H
2O (20: 80-60: 40) (0-30min) gradient elution; Column temperature: 25 ℃; Flow velocity: 1.0ml/min; Detector: UV-detector; Detect wavelength: 280nm.
3. the mensuration of working curve: pipette above-mentioned standard solution 11.5ml, 23.0ml, 31.2ml, 51.8ml and 62.5ml respectively, mix, obtain the mixing solutions of standard substance.The concentration of each standard substance is respectively 10.15mg/ml, 20.3mg/ml, 30.12mg/ml, 50.18mg/ml and 60.25mg/ml.Each standard solution check analysis is determined the retention time of each standard substance chromatographic peak among the sample introduction 16 μ l and 1.The standard substance mixing solutions respectively pipettes 0.2,0.4,0.8,1.2,1.6,2.0ml, respectively with methanol constant volume to 2ml, obtain the standard substance mixing solutions of different concns gradient, each solution sample introduction 16 μ l is respectively analyzed.With ultraviolet absorption value (A) is ordinate zou, and standard substance concentration (mg/ml) is X-coordinate, calculates the working curve and the regression equation of each standard substance.
4. total lignans assay: accurately take by weighing the total lignans extract 10mg of dry constant weight, with dissolve with methanol and be settled to 10ml, concentration is 1mg/ml.Analyze with sample introduction 16 μ l behind the 0.45 μ m filtering with microporous membrane.Calculate the content and the total content of 1,2,3,5 and 6 five compound with working curve gained standard equation.
According to the present invention, pharmaceutical composition of the present invention or extract can be by oral or parenteral route administrations.The formulation that is fit to oral administration has been said for example: tablet, capsule, solution, suspension, granule or pill etc.Be fit to parenteral route such as vein, the formulation and the exterior-applied formulation of subcutaneous or muscle administration have been said injection liquid, liniment, ointment or suppository etc. for example.
According to the present invention, the consumption of extract of the present invention and effective constituent thereof depends on factors such as the type of age, body weight and the disease of using object and severity.
Description of drawings
Fig. 1 is the The selection result of celecoxib and COX-2 binding ability
Fig. 2 is the The selection result of composition and COX-2 binding ability in Caulis Trachelospermi 95% ethanol extraction
1 celecoxib, 2 trachelosides, 3 nortrachelosides unit, 4 fringe matairesinols
5 trachelospermum jasminoide aglycons, 6 aretigenins
Embodiment
The following examples are used for further specifying the present invention, but it does not mean that any limitation of the invention.
Embodiment 1
Caulis trachelospermi total lignans extractive's preparation
The preparation method
Stem of confederate-jasmine (1kg) 95% alcohol reflux 3 times (V: W=6: 1), filtered through gauze, concentrating under reduced pressure gets extract 187.5g.95% dissolve with ethanol adds 282g diatomite (thick cream: diatomite=1: 1.5), mix thoroughly, volatilize, pulverize, add 536ml sherwood oil extract at room temperature three times, filter filtrate simmer down to petroleum ether dissolution part 9.177g.Filter residue adds twice of 95% alcohol reflux.Suction filtration while hot, filtrate concentrate medicinal extract 173.1g.With 2L 10% dissolve with ethanol, centrifugal (3000 rev/mins 10min), are got AB-8 macroporous resin column on the supernatant (column volume 2L is with 10% ethanol pre-equilibration).With 4L 10% ethanol elution, elutriant discards after reclaiming solvent earlier.Use 4L 95% ethanol elution again, get total lignans extract 44.6g behind the elutriant concentrate drying, yield is 4.46%.The content that records each lignanoid's composition in the embodiment 1 prepared extract with top described total lignans measuring method and/or high performance liquid chromatography is respectively nortracheloside (1) 12.64 weight %, tracheloside (2) 24.70 weight %, (3) the 1.77 weight % of nortracheloside unit, trachelospermum jasminoide aglycon (5) 3.34 weight % and aretigenin (6) 10.54 weight %, and total lignans content is 52.98 weight %.
Embodiment 1 extract and the wherein anti-inflammatory action evaluation of main effective constituent
Experiment material
Laboratory animal: male kunming mouse, body weight 18-22g; Male Sprague-Dawley rat, body weight 140-180g; All available from raise Experimental Animal Center in the court.
Given the test agent: embodiment 1 extract; Nortracheloside (1), tracheloside (2), nortracheloside unit (3), fringe matairesinol (4), trachelospermum jasminoide aglycon (5) and aretigenin (6) (separate in Caulis Trachelospermi extract by the contriver, measure purity all more than 98% through the liquid phase normalization method), celecoxib (Pfizer (Pfizer) production).
Laboratory apparatus: punch tool, self-control are measured the equipment of rat foot volume etc.
Experiment reagent: Oleum Tiglii and carrageenin are bought from sigma company, and other is homemade analytical pure.
Experimental technique and result:
Oleum Tiglii causes the mice ear test
1. male mice is 40, be divided into 4 groups at random, every group 10, each given the test agent directly is dissolved in the stimulant, stimulant is by Oleum Tiglii: ethanol: water: ether=2: 20: 5: 73 (V/V) form, respectively be coated with the stimulant 10 μ l to be dissolved with given the test agent in the mouse right ear two sides, the blank group singly is coated with stimulant, and left ear does not process.Put to death animal behind the 4h.Cut two ears, strike down the auricle that diameter is 7.5mm.Weigh immediately, calculate left and right sides ear weight difference, and definite inflammation oedema degree.Comparative group differences significance.The results are shown in Table 2.
2. male mice is 80, is divided into 8 groups at random, and 10 every group, each given the test agent is dissolved in the acetone, respectively is coated with in the mouse right ear two sides with stimulant (forming with shown in 1) 10 μ l, and left ear does not process.Respectively be coated with given the test agent 10 μ l in the mouse right ear two sides behind the 15min, the blank group is coated with the acetone with equal volume, and left ear is coated with the acetone with equal volume.Put to death animal behind the 4h.Cut two ears, strike down the auricle that diameter is 7.5mm.Weigh immediately, calculate left and right sides ear weight difference, and definite inflammation oedema degree.Comparative group differences significance.The results are shown in Table 3.
Carrageenin causes the pedal swelling test
36 of male rats are divided into 6 groups at random, and 6 every group, given the test agent is suspended in the physiological saline, abdominal injection (ip) administration 0.1ml, and blank gives the physiological saline with volume.Half an hour after the administration is in the normal saline solution 0.1ml (aseptic technique) of rat right back vola subcutaneous injection 1% carrageenin.By the micropipet method of masurement measure cause scorching before and cause scorching back 1-3 hour (per hour measuring once) right back sufficient volume of rat.With its sufficient volume difference that causes scorching front and back is the swelling degree.Comparative group differences significance.The results are shown in Table 4
Data processing: all data represent that with x ± SD group difference is checked with t.
Table 2 Stem of confederate-jasmine lignan component (being dissolved in stimulant) is to the restraining effect of mice ear
Annotate: compare * P＜0.001**P＜0.0001***P＜0.00001 with the blank group
Total lignans extract, nortracheloside (1), tracheloside (2) are insoluble to stimulant
Table 3 caulis trachelospermi total lignans extractive and wherein main lignan component (being dissolved in acetone) are to the restraining effect of mice ear
Annotate: compare * P＜0.05**P＜0.01***P＜0.0001 with the blank group
Table 4 caulis trachelospermi total lignans extractive and wherein main lignan component are to the restraining effect of rat paw edema
Annotate: compare * P＜0.05 with the blank group
Conclusion
Studies show that the total lignans extract of embodiment 1 and main lignan component wherein can significantly suppress mice ear, though very not remarkable to group difference in the restraining effect test of rat paw edema, demonstrated tangible trend.Above result shows that total lignans extract and main lignan component wherein have anti-inflammatory action.
The analgesic activity evaluation of embodiment 1 extract
Experiment material
Laboratory animal: kunming mouse, male and female half and half, body weight 18-22g, available from raise Experimental Animal Center in the court.
Given the test agent: embodiment 1 extract, indomethacin (available from Cayman company).
Laboratory apparatus: 2L beaker, pick up camera etc.
Reagent is used in experiment: be homemade analytical pure.
Experimental technique and result:
40 of mouse are divided into 5 groups at random, and 8 every group, gastric infusion (ig) (fasting 16h before the administration) or abdominal injection (ip) administration 0.1ml, the blank group gives with the water of volume or physiological saline.After half an hour, abdominal injection (ip) 0.6% acetum 0.2ml, behind the placement 5min, every mouse is turned round body number of times (belly and hind leg elongation once are a writhing response) in the record 15min.Experimental result is represented with turning round the body inhibiting rate:
The results are shown in Table 5 and table 6
Data processing: all data represent that with x ± SD group difference is checked with t.
Table 5 caulis trachelospermi total lignans extractive is to the restraining effect of mouse acetic acid twisting reaction
Annotate: compare * P＜0.05**P＜0.01 with the blank group
Conclusion
The total lignans extract that studies show that embodiment 1 is being irritated the acetic acid twisting reaction that can significantly suppress mouse on stomach (ig) and two kinds of route of administration of abdominal injection (ip), shows that the total lignans extract has analgesic activity.
Main lignan component is active with combining of cyclooxygenase (COX) in embodiment 1 extract
Experiment material
Given the test agent: Stem of confederate-jasmine 95% ethanol extraction, celecoxib (Pfizer (Pfizer) production).
Laboratory apparatus: Agilent 1100 highly effective liquid phase chromatographic systems are furnished with the quaternary gradient pump, the DAD UV-detector; High speed freezing centrifuge; Ultra-fine filter (molecular weight that dams is 30,000).
Experiment uses reagent: COX-2 (ovine) to buy from U.S. Cayman chemical reagents corporation, and other is homemade analytical pure.
Experimental technique and result:
Pipette COX-2 (ovine) 20 μ l (3.5 μ g/ μ l), add screened sample solution 250 μ l (celecoxib 7.3 μ g/ml, Stem of confederate-jasmine 95% ethanol extraction 0.17mg/ml), (50mM pH7.4) supplies the PBS damping fluid of using of cumulative volume less than 270 μ l.37 ℃ of dark places are transferred in the ultra-fine filter after breeding 1h, centrifugal (8500rpm, 25 ℃) 12min.Add 400 μ l PBS damping fluids and wash at twice, centrifugal not removing produces specificity bonded material with enzyme, adds 400 μ l distilled water again and washs at twice, the centrifugal salt constituents of removing.Add 20% acetonitrile solution that 400 μ l contain 1% trifluoroacetic acid at last and wash at twice, centrifugal ultrafiltration is collected filtrate, with 30 μ l dissolve with methanol, gets 20 μ l and is used for the HPLC-DAD analysis after the lyophilize.Other establishes not enzyme-added control group, and other operation is the same.
Chromatographic condition: chromatographic column: NUCLBODUR C
18Post (4.6mm * 250mm, 5 μ m); Moving phase: methanol-water ((60: 40) (0min) → (85: 15) (15min)) gradient elution (celecoxib) or methanol-water ((2: 98) (0min) → (95: 5) (30min)) gradient elution (Stem of confederate-jasmine 95% ethanol extraction); Column temperature: 25 ℃; Flow velocity: 1.0ml/min; Detect wavelength: 251nm (celecoxib) or 230nm (Stem of confederate-jasmine 95% ethanol extraction).
The results are shown in Figure 1 and Fig. 2.
Conclusion
Studies show that all there are certain activity that combines in lignan component main in the total lignans extract of embodiment 1 and COX-2, prompting total lignans extract and wherein lignan component may be the COX inhibitor, its anti-inflammatory and analgesic effect mechanism may be relevant with the activity that suppresses COX enzyme catalysis arachidonic acid generation prostaglandin(PG).And, studies show that in a large number that abroad cox 2 inhibitor has the activity that suppresses tumor growth and transfer, and low dose of COX-1 inhibitor can there be antithrombotic activity (as acetylsalicylic acid).Thereby Caulis Trachelospermi total lignans extract and wherein lignan component have antitumor or antithrombotic effect probably.
Claims (6)
1. caulis trachelospermi total lignans extractive, it contains the lignan component of 30-90 weight % and contains a kind of as shown in the formula the described compound of 1-6 at least:
Described extract extracts Stem of confederate-jasmine by water, alcoholic acid mixture and macroporous resin column chromatography method combination extraction Stem of confederate-jasmine prepares.
2. the described preparation method of extract of claim 1, this method comprise that water, alcoholic acid mixture extract Stem of confederate-jasmine and macroporous resin column chromatography method combination extraction Stem of confederate-jasmine.
3. the pharmaceutical composition that contains the described extract of claim 1 and one or more pharmaceutically acceptable carriers or vehicle.
4. the described extract of claim 1 is used for the treatment of the product of inflammation and/or pain or the purposes in the medicine in preparation.
5. the described extract of claim 1 is used for the treatment of the product of thrombus or the purposes in the medicine as cox-2 inhibitors in preparation.
6. the purposes of claim 5, wherein said cyclooxygenase is COX-2 and/or COX-1.
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| KR100847439B1 (en) * | 2006-07-03 | 2008-07-21 | 신일제약주식회사 | Trachelospermi caulis extracts compositions for treating or preventing inflammatory diseases |
| KR100847440B1 (en) * | 2007-01-24 | 2008-07-21 | 신일제약주식회사 | Drug of herbal mixture for treating or preventing inflammatory diseases |
| KR101192409B1 (en) | 2008-09-25 | 2012-10-17 | 신일제약주식회사 | Pharmaceutical compositions for preventing or treating inflammatory diseases using Trachelospermi caulis partitionated extract and its manufacture method |
| FI20106293A0 (en) | 2010-12-06 | 2010-12-06 | Emilia Peuhu | New pharmaceutical compositions |
| CN103316059A (en) * | 2013-07-10 | 2013-09-25 | 吴中区胥口精益生物医药研究所 | Chinese starjasmine stem essence as well as preparation method and pharmaceutical application thereof |
| CN107602642B (en) * | 2017-10-13 | 2020-09-11 | 陕西嘉禾药业有限公司 | Method for extracting and purifying trachelospermin from safflower seed |
| CN108295100B (en) * | 2018-03-01 | 2021-06-22 | 南昌大学 | Application of parasitic loranthus extract in preparing medicine for treating rheumatoid arthritis |
| CN110554129B (en) * | 2019-09-12 | 2020-09-25 | 浙江省农业科学院 | Screening method of potential anti-inflammatory active ingredients in extra-virgin olive oil |
| CN114748492B (en) * | 2022-05-13 | 2023-03-10 | 山东大学齐鲁医院(青岛) | Medicine for treating atherosclerosis |
| CN115340512B (en) * | 2022-09-22 | 2024-03-15 | 中国科学院西北高原生物研究所 | Three diaryl butyrolactone lignans compounds in jellyfish herba Saussureae Involueratae, and extraction and separation method and application thereof |
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