CN1489994A - Extracts of fat soluble benzyl ethene contents from curcuma longa and use in preparation - Google Patents
Extracts of fat soluble benzyl ethene contents from curcuma longa and use in preparation Download PDFInfo
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Abstract
An application of the phenylpropylethylene curcumin or the composition of curcumin, demethoxy curcumin and bidemethoxy curcumin in the medicine or health-care food for treating depression is disclosed.
Description
Technical field
Two kinds of preparations that the present invention relates to natural drug and foodstuff effective ingredient monomer or be combined into that branch forms and the single component of the fat-soluble phenylpropyl alcohol vinyl of preparation new purposes, particularly Rhizoma Curcumae Longae composition or the medicine that compound recipe is prepared into the treatment depression.
Background technology
Depression is serious harm human physical and mental health's commonly encountered diseases, a frequently-occurring disease.The recent statistics result of World Health Organization (WHO) shows that global prevalence is about 11%, and the prediction depression will be classified on the year two thousand twenty spectrum of disease second as.Many serious diseases (as heart disease, apoplexy, cancer, immune disease etc.) also usually can cause depression.Depression rate occurred frequently, high disability rate and being on the rise property of social danger have caused common concern in the world.At present all there is the shortcoming that is difficult to overcome in use in Western medicine, and is narrower as the antidepressant spectrum, toxic and side effects is big, easily recurrence etc. after the drug withdrawal.Lack efficient, of fine quality, safe, controlled antidepressant drug on both at home and abroad on the drug market.Still lack at present satisfied medicine.
Summary of the invention
The purpose of this invention is to provide two kinds of preparations that fat-soluble phenylpropyl alcohol vinyl monomer of Rhizoma Curcumae Longae or composite parts extract are formed.
Another purpose of the present invention provides the application of preparation in preparation treatment depression medicine of fat-soluble phenylpropyl alcohol vinyl monomer of Rhizoma Curcumae Longae or composite parts composition.
It is monoamine oxidase inhibitor that another object of the present invention provides the antidepressant mechanism of action of curcumin.
Purpose of the present invention can reach by following measure:
The fat-soluble phenylpropyl alcohol vinyl of a kind of Rhizoma Curcumae Longae component extract is characterized in that being is that curcumin, demethoxycurcumin, bisdemethoxycurcumin are formed by monomer curcumin or composite parts; Monomer curcumin purity content is 90～96%, and composite parts contains curcumin, demethoxycurcumin, bisdemethoxycurcumin content weight ratio and is: 1: (0.5-0.01): (0.4-0.01).
Above-mentioned complex or monomer extract extraction process are as follows:
1, Rhizoma Curcumae Longae composite parts or title compound recipe are Rhizoma Curcumae Longae effective site, its extraction process is with fat-soluble organic solvent such as ethanol, methanol, acetone, ethyl acetate, chloroform, dichloromethane etc., concentration can get the effective site of Rhizoma Curcumae Longae with 75-95% ethanol or acetone (or aforementioned other solvents) lucifuge percolation or heating and refluxing extraction method, the dry extract yield is 5% ±, wherein curcumin accounts for 73-82%.Its extraction process flow process is as follows: Rhizoma Curcumae Longae coarse powder 75-95% ethanol or acetone percolation or heating and refluxing extraction, extracting solution concentrates through vacuum and low temperature, dry concentrate, levigate, promptly get effective site (containing curcumin, demethoxycurcumin, bisdemethoxycurcumin) with petroleum ether or industrial naptha defat and also claim the Rhizoma Curcumae Longae compound recipe.
2, high-purity curcumin extraction, purifying process: with effective site process column chromatography for separation, thin layer follow the tracks of similar compound solution, merge and concentrate, get the high-purity turmeric effective ingredient, successfully isolate purity greater than 96% main active substances curcumin (curcumin), contain demethoxycurcumin, bisdemethoxycurcumin in addition, its ratio as described above.Its separation process is as follows: the Rhizoma Curcumae Longae coarse powder is crossed 20 orders 75-95% ethanol or acetone (or above-mentioned other solvents) percolation or reflux, extract,, extracting solution concentrates through vacuum and low temperature, levigate concentrate gets effective site dry powder, behind defat with petroleum ether, separate with silicagel column, with chloroform (or dichloromethane) and ethanol gradient elution, be in charge of that collection, thin layer are followed the tracks of, same pipe merges, the vacuum and low temperature concentrate drying gets high-purity curcumin (96-99%) respectively; In addition method with effective site behind defat with petroleum ether, with the ethanol of 75-95% repeatedly recrystallization can contain the curcumin of 90-94%.
Annotate: extract, note when separating lucifuge.
The oral formulations that is prepared into based on the single component or the compound recipe of curcumin comprises oral tablet, capsule, granule, solid dispersion, nanoparticle, Emulsion.
Advantage of the present invention
The invention provides a kind of medicine-food two-purpose, have the new medicine preparation or the health food of treatment, improvement or the effect of prevention depression.The present invention has successively developed dosage forms such as capsule, tablet, Emulsion, nanoparticle, nanometer liposome, beta-CD inclusion and solid dispersion.Zoopery shows: various dosage forms all have the effect of varying degree, are good with solid dispersion and nanoparticle as preparation formulation.Effective site can be used as the antidepressant health product; High-purity curcumin (content 90-96%) solid dispersion and nanoparticle can be used as antidepressant drug and preparation.This product is compared with the positive drug fluoxetine, and the single component or the compound recipe novel formulation that are become to be grouped into by Rhizoma Curcumae Longae phenylpropyl alcohol vinyl have the advantage that effect is approximate, safe, effectiveness is good.
The Rhizoma Curcumae Longae phenylpropyl alcohol vinyl component preparation of gained of the present invention has good safety, and the patient who is suitable for diseases such as all ages and classes level and all types of patients with depression and the cardiovascular that occurs together, diabetes, cancer uses.
The effectiveness of the preparation for treating depression of the evaluation of the present invention's science on depression model and definite Rhizoma Curcumae Longae phenylpropyl alcohol vinyl single component or composite parts, and be index with curcumin, demethoxycurcumin, bisdemethoxycurcumin content, set up the quality standard of science, drug effect is reliable and stable, and the technological process controllability is strong.
The medicament sources of the treatment depression that is obtained by the present invention is single, and active ingredient is clear and definite.
The preparation technology that the present invention adopts obtains to have the preparation of treatment depression, technology is reasonable, workable, be convenient to suitability for industrialized production, the product that obtains have good effect, safe and reliable, quality controllable, the incomparable advantage of multiple Western medicine such as be easy to take, cheap, can make the lot of domestic and foreign patient break away from slight illness, improve the quality of living, have vast market prospect.
The specific embodiment
Below the embodiment be embodiment only as the usefulness of further setting forth invention, can not be used for limiting the present invention.
Embodiment 1:
The Rhizoma Curcumae Longae pulverizing medicinal materials is crossed 20 mesh sieves, take by weighing 500 gram medicated powder, measure the ethanol infiltration after 1 hour with one times, pack into equably in the percolator, the limit rim is pressed, and injects the capacity soak with ethanol and spends the night, flow velocity with 2-5ml/min carries out percolation, collect percolate, follow the tracks of with tlc analysis and detect (developing solvent: chloroform-dehydrated alcohol 100: 2.5), merge percolate until the curcumin speckle not occurring.Low temperature, concentrating under reduced pressure become extractum, put drying under reduced pressure in the vacuum drying ware, put in the apparatus,Soxhlet's, with petroleum ether (or can be used as the gasoline that solvent is used) heating extraction 16-20 hour, remove volatile oil, residue dry dry extract, Rhizoma Curcumae Longae benzyl ethylene chemical compound gets 14.5 grams, yield 2.9%.Through checking that with HPLC (condition is seen embodiment 2) wherein curcumin accounts for 82.01%, demethoxycurcumin 14.51%, bisdemethoxycurcumin 2.10%, impurity 1.38%.
Embodiment 2:
Take by weighing activated column chromatography silica gel (100-200 order) 400g, stir evenly with chloroform, and the glass chromatography column of packing into (40 * 120mm), use chloroform 5ml/min flow velocity balance 10～30 hours.Take by weighing the Rhizoma Curcumae Longae propene compound 20g of said extracted, with the chloroform dissolving and the good chromatographic column of balance of packing into, the adjustment flow velocity is 2-5ml/min, add chloroform and a spot of ethanol gradient elution, to there being yellow the outflow to begin to collect, dehydrated alcohol 100: 2.5) or HPLC (C 15ml/ pipe is with TLC (developing solvent chloroform:
8Post ultraviolet light detector, wavelength 254nm mobile phase: acetonitrile-10% glacial acetic acid 44-56 flow velocity 1.2ml/min room temperature) follow the tracks of the curcumin speckle.Collecting liquid puts in the rotary evaporator, concentrating under reduced pressure, logical nitrogen heating (45 ℃ ± 1) is removed solvent and is got orange-yellow crystal powder, after HPLC checks that curcumin: demethoxycurcumin: Bisdemethoxycurcumin: its weight ratio of impurity peaks is 97.1%: 1.23%: 0.72%: 0.95%.
Embodiment 3:
Take by weighing activated column chromatography silica gel (100-200 order) 500g, stir evenly with ethyl acetate, the glass chromatography column of packing into is used ethyl acetate 5ml/min flow velocity balance 10～30 hours.Take by weighing the Rhizoma Curcumae Longae propene compound 7g of said extracted, with the ethyl acetate dissolving and the good chromatographic column of balance of packing into, the adjustment flow velocity is 2-5ml/min, add ethyl acetate and a spot of ethanol gradient elution, begin to collect to there being color to flow out, dehydrated alcohol 100: 2.5) or HPLC (C 15ml/ pipe is with TLC (developing solvent acetone:
8Post ultraviolet light detector, wavelength 254nm mobile phase: acetonitrile-10% glacial acetic acid 44-56 flow velocity 1.2ml/min room temperature) follow the tracks of the curcumin speckle.Collect liquid (45 ℃) concentrating under reduced pressure of heating, logical nitrogen, heating (45 ℃ ± 1) is removed solvent and is got orange-yellow crystal powder in the decompression rotary evaporator, after HPLC checks that curcumin: demethoxycurcumin: Bisdemethoxycurcumin: its weight ratio of impurity peaks is 98.0%: 1.30%: 0.68%: 0.02%.
Embodiment 4:
Take by weighing said extracted curcumin chemical compounds 10g, add 300ml ethanol after 80-85 ℃ of water-bath is back to dissolving, filters, is cooled to room temperature, put into-16～-19 ℃ of refrigerators 1 day, promptly have crystallization to separate out.Filter, get crystallization, recrystallization is 1-2 time again, obtains curcumin 2.95g, detects its weight ratio through the HPLC method to be: curcumin: demethoxycurcumin: Bisdemethoxycurcumin: impurity peaks 91.5%: 6.2%: 0.68%: 1.62%.
Embodiment 5:
Curcumin purity 90-96% is to the influence of animal depression model due to the reserpine.Observation index: 1, eyes is sagging; 2, motion can not; 3, animal heat.The results are shown in Table I:
Table I: curcumin causes the influence (X ± SD.n=20) of mice depression model to reserpine
The sagging motion of eyes can not number of animals
Group dosage (mg/kg)/total number of animals/total number of animals animal heat (℃)
Normal control group 0.2ml/10gNC 0,/20 0,/20 36.23 ± 0.57
Model group 0.2ml/10gNC 18
△ △/ 20 17
△ △/ 20 35.73 ± 0.65
△
Fluoxetine group 15.6mg/kg 11*/20 7*/20 36.15 ± 0.59*
Low dose of 30mg/kg 15/20 8* of curcumin/20 36.17 ± 0.43*
Dosage 50mg/kg 11*/20 8*/20 36.15 ± 0.53* in the curcumin
The heavy dose of 100mg/kg 9* of curcumin/20 5**/20 36.17 ± 0.43*
Annotate: closing half number of animals and motion of eyes can not number of animals, and the result carries out λ
2Check; Animal anus temperature, result are carried out the T check.Compare with the normal control group,
△P＜0.05,
△ △P＜0.01; Compare with model group
*P＜0.05,
*P＜0.01
Result of the test shows: the medicine curcumin causes that to reserpine the depressed eyes that occurs of mice is sagging, motion can not have obvious inhibitory action with the animal heat symptom, compares with model group that there were significant differences (P＜0.05, P＜0.01).Show that the medicine curcumin can improve the animal depression that is caused by reserpine.
Embodiment 6:
Curcumin (purity 90-96%) causes the influence of mice depression model to tetrabenazine.Observation index: 1, eyes is sagging; 2, stiff firmly effect.The results are shown in Table II:
Table II: curcumin causes the influence (X ± SD.n=20) of animal depression model to tetrabenazine
The stiff firmly number of animals of the sagging number of animals of eyes
Group dosage (mg/kg) 30 minutes 60 minutes 90 minutes 30 minutes 60 minutes 90 minutes
Normal control group 0.2ml/10gNS 100000
Model group 0.2ml/10gNS 19
△ △18
△ △18
△ △18
△ △18
△ △18
△ △
Fluoxetine group 15.6 5** 8** 11* 6** 7** 10*
Little dose 30 16 19 14 8** 14 11* of curcumin
Dosage 50 15 16 18 11* 12* 7** in the curcumin
The heavy dose of 100 11* 12* 9* 4** 10* 11* of curcumin
Annotate: close half number of animals and the stiff number of animals of living of eyes, the result carries out λ
2Check; Compare with the normal control group,
△ △P＜0.01; Compare with model group
*P＜0.05,
*P＜0.01.
Result of the test shows: the medicine curcumin causes that to tetrabenazine sagging, the stiff number of animals of living of the eyes of animal depression model compares with model, Rhizoma Curcumae Longae is heavy dose of there were significant differences (P＜0.05, p＜0.01), in dosage obviously reduce the stiff number of animals of living, total show the medicine curcumin to tetrabenazine cause that animal depression model eyes is sagging, animal is stiff that obvious inhibitory action firmly all arranged.
Embodiment 7:
Curcumin (purity 90-96%) is to the influence of mouse tail suspension test.The results are shown in Table III:
Table III: the influence that Rhizoma Curcumae Longae is tested mouse tail suspension (X ± SD.n=20)
Group dosage (mg/kg) hangs the tail dead time (S)
Normal matched group 0.2ml/10gNS 111.05 ± 63.21
Model group 0.2ml/10gNS 214.45 ± 86.66
△ △
Fluoxetine group 15.6 149.95 ± 98.36
The low dose of 30 146.00 ± 104.62* of curcumin
Dosage 50 140.80 ± 117.55* in the curcumin
The heavy dose of 100 98.15 ± 91.43** of curcumin
Annotate: compare with the normal control group,
△ △P＜0.01; Compare with model group
*P＜0.05,
*P＜0.01.
Result of the test shows: the medicine Rhizoma Curcumae Longae was compared with model group the outstanding tail dead time of mouse tail suspension test, and there were significant differences, showed that the medicine curcumin has obvious antagonism to the outstanding tail dead time of mouse tail suspension test.
Embodiment 8:
Curcumin (purity 90-96%) is to the influence of mice forced swimming test.The results are shown in Table IV:
Table IV: Rhizoma Curcumae Longae is to the influence of mice forced swimming test (X ± SD.n=20)
Group dosage (mg/kg) hangs the tail dead time (S)
Normal control group 0.2ml/10gNS 205.67 ± 86.43
Model group 0.2ml/10gNS 619.70 ± 120.44
△ △
Fluoxetine group 15.6 497.95 ± 169.43*
The low dose of 30 474.28 ± 193.14** of curcumin
Dosage 50 450.68 ± 175.31** in the curcumin
The heavy dose of 100 454.33 ± 158.60** of curcumin
Annotate: compare with the normal control group,
△ △P＜0.01; Compare with model group
*P＜0.05,
*P＜0.01.
Result of the test shows: the medicine curcumin was compared with model group the dead time of mice swimming test, and there were significant differences, showed that the medicine curcumin has obvious antagonism to the non-swimming time of mice swimming test.
Embodiment 9: the compound turmeric element is to the influence of mouse tail suspension and swimming time.
The results are shown in Table V:
Table V compound turmeric element is to the influence of mouse tail suspension and swimming time
| Group | Number of animals (n) | Dosage (mg/kg) | The outstanding tail dead time (S) | Non-swimming time (s) |
| Positive group (fluoxetine) | ????10 | ????16 | ????26.7±19.5 | ????1.6±1.83 |
| Negative group | ????10 | ????/ | ????69.8±23.3 | ????53.7±30.5 |
| The compound turmeric element | ????10 | ????15 | ????33.2±23.2** | ????11.25±9.38** |
| ????10 | ????30 | ????46.4±32 | ????24.4±20.6** | |
| ????10 | ????50 | ????40.5±31.18** | ????10.18±0.6** | |
| ????10 | ????80 | ????50.3±23.39 | ????14.7±13.8** | |
| ????10 | ????160 | ????51.1±39.8 | ????8.1±10.1** |
Experiment shows: the various dose of various compound turmeric elements all shows anti-in various degree melancholy effect.
Annotate: * * and negative control group are than P＜0.05
Embodiment 10:
The solid dispersed formulation of Rhizoma Curcumae Longae is to the influence of mouse tail suspension and swimming time.The results are shown in Table VI:
Table VI: the curcumin solid dispersant is to the influence of mouse tail suspension and swimming time
Group number of animals dosage (mg/kg) hangs tail dead time (S) non-swimming time (S)
Fluoxetine
Positive controls 10 16 26.7 ± 19.5 1.6 ± 1.83
Negative control group 10/69.8 ± 23.3 53.7 ± 30.5
Small dose group 10 30 31.7 ± 30.9** 3.83 ± 5.2**
Middle dosage group 10 50 36.3 ± 38.4** 4.50 ± 4.4**
* represents P＜0.05
Experiment shows: the curcumin solid particle dispersants relatively has appreciable impact to mouse tail suspension and swimming time and negative control group.
Embodiment 11:
The plain nanoparticle of compound turmeric is to the influence of mouse tail suspension and swimming time.The results are shown in Table VII:
The plain nanoparticle of Table VII compound turmeric is to the influence of mouse tail suspension and swimming time
Group number of animals dosage (mg/kg) hangs tail dead time (S) non-swimming time (S)
Fluoxetine
Positive controls 10 16 26.7 ± 19.5 1.6 ± 1.83
Negative control group 10/69.8 ± 23.3 53.7 ± 30.5
Plain 10 15 65.6 ± 36.4 4 ± 5.15** of compound turmeric
* represents P＜0.05
Experiment shows: the plain nanoparticle of compound turmeric relatively has appreciable impact to mice swimming time and negative control group.
Embodiment 12: the antidepressant mechanism of action test of curcumin, show that by mouse test the mechanism of action of curcumin is a monoamine oxidase inhibitor, and the results are shown in Table XIII:
Table X III: the inhibition test of ammoxidation single enzyme
1h 2h 3h 4h 5h 6h before the group administration
Model group 37.3 ± 0.3 36.1 ± 0.6 34.0 ± 0.9 33.5 ± 0.9 33.1 ± 1.1 33.0 ± 1.0 33.0 ± 1.0
Positive group 37.4 ± 0.3 36.2 ± 0.7 35.8 ± 0.8** 36.2 ± 1.2** 35.9 ± 0.7** 35.6 ± 0.6** 34.2 ± 0.2**
Heavy dose of 37.3 ± 0.5 36.1 ± 0.3 36.2 ± 0.7**, 35.9 ± 0.6**, 35.3 ± 0.7**, 35.8 ± 0.6**, 35.8 ± 0.6**
Middle dosage 37.3 ± 0.6 36.1 ± 0.7 35.8 ± 0.4**, 36.1 ± 0.4**, 36.1 ± 0.3**, 35.8 ± 0.4**, 35.5 ± 0.6**
Low dose of 37.3 ± 0.3 36.1 ± 0.5 35.9 ± 0.9**, 35.6 ± 0.8**, 36.0 ± 0.6**, 35.5 ± 1.0**, 35.3 ± 1.1**
Annotate: 1, heavy dose is 100mg/kg, and middle dosage is 50mg/kg, and low dose is 30mg/kg, and used animal is the ICR mice.
2, each group relatively compares * * P＜0.01 for the difference before some hrs after the administration and the administration.
Experiment shows: can find out tentatively that from above result the monoamine mechanism of action of curcumin is a monoamine oxidase inhibitor, by suppressing ammoxidation single enzyme, cause accumulating of monoamine class material, the performance antidepressant effect.
Claims (6)
1, the fat-soluble phenylpropyl alcohol vinyl of a kind of Rhizoma Curcumae Longae component extract is characterized in that being is that curcumin, demethoxycurcumin, bisdemethoxycurcumin are formed by monomer curcumin or composite parts; Monomer curcumin purity content is 90～96%, and composite parts contains curcumin, demethoxycurcumin, bisdemethoxycurcumin weight ratio and is: 1: (0.5-0.01): (0.4-0.01).
2, the fat-soluble phenylpropyl alcohol vinyl of Rhizoma Curcumae Longae according to claim 1 component extract is characterized in that said medicament is an oral formulations.
3, the fat-soluble phenylpropyl alcohol vinyl of Rhizoma Curcumae Longae according to claim 2 component extract is characterized in that said oral formulations is to comprise oral tablet, capsule, granule, solid dispersion, nanoparticle, Emulsion.
4, the fat-soluble phenylpropyl alcohol vinyl of the Rhizoma Curcumae Longae application of preparation in preparation treatment depression medicine that become to be grouped into.
5, the fat-soluble phenylpropyl alcohol vinyl of the Rhizoma Curcumae Longae preparation that becomes to be grouped into improves application in the depressed behavior in preparation.
6, the fat-soluble phenylpropyl alcohol vinyl of the Rhizoma Curcumae Longae application of preparation in the activity that reduces ammoxidation single enzyme that become to be grouped into.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100486567C (en) * | 2004-08-12 | 2009-05-13 | 山东绿叶天然药物研究开发有限公司 | Curcumin emulsion and its preparation process |
| US20140371327A1 (en) * | 2005-05-30 | 2014-12-18 | Arjuna Natural Extracts, Ltd. | Formulation of Curcumin with Enhanced Bioavailability of Curcumin and method of preparation and treatment thereof |
| US10286027B2 (en) | 2005-05-30 | 2019-05-14 | Arjuna Natural Extracts, Ltd. | Sustained release formulations of curcuminoids and method of preparation thereof |
| US10485843B2 (en) | 2005-05-30 | 2019-11-26 | Arjuna Natural Private Limited | Composition to enhance the bioavailability of curcumin |
-
2003
- 2003-08-22 CN CNA031528082A patent/CN1489994A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100486567C (en) * | 2004-08-12 | 2009-05-13 | 山东绿叶天然药物研究开发有限公司 | Curcumin emulsion and its preparation process |
| US20140371327A1 (en) * | 2005-05-30 | 2014-12-18 | Arjuna Natural Extracts, Ltd. | Formulation of Curcumin with Enhanced Bioavailability of Curcumin and method of preparation and treatment thereof |
| US10159654B2 (en) * | 2005-05-30 | 2018-12-25 | Arjuna Natural Extracts, Ltd | Formulation of curcumin with enhanced bioavailability of curcumin and method of preparation and treatment thereof |
| US10286027B2 (en) | 2005-05-30 | 2019-05-14 | Arjuna Natural Extracts, Ltd. | Sustained release formulations of curcuminoids and method of preparation thereof |
| US10485843B2 (en) | 2005-05-30 | 2019-11-26 | Arjuna Natural Private Limited | Composition to enhance the bioavailability of curcumin |
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