CN1117734C - Process for extracting lotucine from plumula nelumbinis - Google Patents
Process for extracting lotucine from plumula nelumbinis Download PDFInfo
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- CN1117734C CN1117734C CN98121705A CN98121705A CN1117734C CN 1117734 C CN1117734 C CN 1117734C CN 98121705 A CN98121705 A CN 98121705A CN 98121705 A CN98121705 A CN 98121705A CN 1117734 C CN1117734 C CN 1117734C
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- lotusine
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- plumula nelumbinis
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Abstract
The present invention relates to a preparation method for extracting lotucine from lotus plumule. The lotus plumule Na2CO3 is wetted and soaked by adding methanol with proper quantity, the lotus plumule is recovered and filtered, filtered solution is degreased, a chloroform water layer is recovered to be filtered, the pH value is adjusted, saturated Redwood ammonia salt is added, and sediments are collected. After air drying, the sediments are dissolved into acetone to filter insoluble substances. After the acetone is recovered to be concentrated, saturated silver sulfate is added to filter the sediments, the filtered solution is decompressed and concentrated into a syrup shape to place to precipitate crystals, and crude product crystals are obtained. Crystallization is repeated to obtain total alkaloids crystals with water solubility, fractional crystallization is carried out in anhydrous alcohol to obtain needle-shaped crystals, separation is carried out to obtain mother liquid and white prismatic crystals, and the crystallization is repeated in the methanol and the water to obtain the fine product lotucine.
Description
The present invention relates to medicine, particularly the preparation method of plant extract medicine.
Once had " Plumula Nelumbinis decocting liquid composition can strengthen the isolated frog heart convergent force " report (Huo Jingwen, mound peptide in morning, Zhang Mao are exhausted: national member representative assembly of second of Chinese Pharmacological Society thesis summary set, second collection, 1956,8-9); Cherish the pharmaceutical research of not making further monomer reactivity composition.We are when carrying out Plumula Nelumbinis vegetable chemistry, pharmaceutical research, after finding to extract the fat-soluble position of Plumula Nelumbinis, the Plumula Nelumbinis water soluble part has the effect of the myocardial contraction of enhancing, and therefrom extraction separation goes out a kind of new alkaloids, turns out to be lotusine through wave spectrum and physico-chemical analysis.Exsomatize to reach and to be phosphodiesterase iii and/or V-type inhibitor in body pharmacological experiment proof LOTUSINE.
The object of the present invention is to provide a kind of low cost, high recovery rate, high-quality (content is greater than 90%), be suitable for the preparation method who from Plumula Nelumbinis, extracts the purifying LOTUSINE of suitability for industrialized production.
Realize that technical scheme of the present invention promptly extracts the preparation method of LOTUSINE and comprise from Plumula Nelumbinis: 1. be raw material with the Plumula Nelumbinis, produce water-soluble total alkaloids; 2. water-soluble total alkaloids separates; 3. Steppecd crystallization separates lotusine.
Concrete operation method is: the Plumula Nelumbinis crude drug is soaked 3 times with methyl alcohol, reclaim methyl alcohol and get total alkali medicinal extract, transfer pH to 2-3 with 1% aqueous hydrochloric acid, filter, get acid total alkaline solution, transfer pH to 9-10 with strong aqua, alkaline total alkali precipitation, suspension, with chloroform extraction 5 times, alkaline water layer, transfer pH to 2-3, add saturated ammonium tetrathiocyanodiaminochromate, fully precipitation, the leaching throw out, air-dry, be dissolved in acetone, the filtering insolubles; The saturated sulfuric acid silvering solution of adding fully precipitates in the acetone solution, and the filtering throw out reclaims acetone, is evaporated to syrupy shape, and crystallization gets the crystallization of crude product total alkali, and respectively at periodic crystallisation in dehydrated alcohol and the water, fractional crystallization in the ethanol gets white prismatic crystal.Add saturated bariumchloride in the aqueous solution, the filtering precipitation, recrystallization gets the lotusine hydrochloride in the dehydrated alcohol.
Accompanying drawing is the process flow sheet of the inventive method.
Below in conjunction with specific embodiment the inventive method is described further.
Embodiment:
Select clean, dry Plumula Nelumbinis 8kg, use an amount of 3%Na in advance
2CO
3(about 100ml/kg crude drug) deg adds an amount of (about 4000ml/kg) methyl alcohol (or ethanol) again and soak a week continuous three times under room temperature.Merge the methyl alcohol soak solution, reclaim methyl alcohol, debris is transferred pH to 2-3 with 1% hydrochloric acid, filters, and filtrate is used ether defatting, continues following steps:
(1). water-soluble total alkaloids separates
With acidic solution after the above-mentioned degreasing, transfer about pH to 9 with strong aqua, with chloroform extraction each 3 times, reclaim chloroform.Water layer filters, filtrate is transferred pH to 2-3 with hydrochloric acid, adds saturated ammonium tetrathiocyanodiaminochromate, generates a large amount of precipitations immediately, the collecting precipitation thing, under the room temperature air-dry after, be dissolved in acetone, the filtering insolubles, after an amount of reclaiming acetone, concentrating, add saturated Sulfuric acid disilver salt and make it abundant precipitation, the filtering precipitation, filtrate is the sulfate liquor of water-soluble total alkali, (or filtrate is behind an amount of concentrating under reduced pressure, add saturated bariumchloride, generate a large amount of barium sulfate precipitates immediately, fully post precipitation, the filtering insolubles), filtrate is placed crystallization through being evaporated to syrupy shape, draws crude product crystallization 8.3g.
(2) Steppecd crystallization separates lotusine
Crude product crystallization 8.3g refluxed down respectively is dissolved in water-soluble 50ml under dehydrated alcohol 200ml (or methyl alcohol) and the hot water bath, periodic crystallisation, water-soluble total alkaloids crystallization 6.2g.Fractional crystallization in dehydrated alcohol again, the first step crystallization gets needle crystal. and filtering separation gets mother liquor; Mother liquor carries out the second step crystallization, gets white prismatic crystal 5.6, is accredited as lotusine through TLC, and periodic crystallisation (deciding available activated carbon decolorizing according to color and luster) in methyl alcohol and water gets elaboration lotusine 4.7g again.
The affirmation of gained material---LOTUSINE (physics and chemistry and wave spectrum are identified)
Main physicochemical constant and wave spectrum are counted a tree name: lotusine hydrochloride: white prismatic crystal (dehydrated alcohol), MP:213-214 ℃; Lotusine vitriol: MP:224-225 ℃.UV λ
229.2nm, 283.2nm, UV λ
(252.4nm blue shift under alkalescence (KOH) condition).Do not fluoresce under the 254nm UV-irradiation; IRV
3550,3390,3200,1615, l530,1520,1265,1240,1115,915,880,840.MS?M/Z：314(M
+1)、298、206、192、107、73、58、44。NMR (D
2O) δ: 3.02 (3H), 3.28 (3H, 2 * N-CH
3), 3.33 (3H, 0-CH
3), 4.39 (1H, multiplets), 5.57 (1H): virtue-H6.72 (1H), 6.74 (4H); Above-mentioned data and document [the grand Yakugaku Zasshi 1965 of Gu Chuan; 85 (5): 472] [CHINA JOURNAL OF CHINESE MATERIA MEDICA 1991 such as Wang Jialing; 16 (11): 673-675] [Chinese medicinal materials 1991 such as Wang Jialing; 14 (6) 36-38] conform to, so confirm as LOTUSINE (Lotusine, lotus nut quaternary ammonium hydroxide, lotusine), its chemical structure is:
Chinese is by name: LOTUSINE, lotus nut quaternary ammonium hydroxide, lotusine
English name: Lotusine
Chemical name: 1-dimethyl-6-hydroxyl-7-methoxyl group-10-benzyl (right-hydroxyl) tetrahydroisoquinoline; Divide in amount: 313.47; Molecular formula: C
19H
23NO
3
Produce LOTUSINE with the inventive method, have that raw material sources are abundant, cost is low, recovery rate is high, high-quality---content greater than 90%, be suitable for characteristics such as suitability for industrialized production.
The experimental result of LOTUSINE pharmacological action:
1. exsomatizing and on the body sample, the lotusine and the derivative that methylates thereof (1-100 μ mol/L) have tangible positive inotropic action and are better than Western medicine amrinone (Amrinone, Am, PDE III inhibitor) and Papaverine (Papavirine, non-selective PDE inhibitor), EC
50Can be suitable with Western medicine;
2. lotusine slightly prolongs myocardial cell's Action Potential Duration, increases Ca
++Electric current is to Ca
++The kinetic character of passage influence is different from Bay K8644 and Racemic isoproterenol;
3. the multiple vasoconstriction medicine of lotusine antagonism effect, vasodilator effect intensity is equivalent to Papaverine;
4. lotusine diastole corpus cavernosum penis blood vessel and action intensity slightly are better than Papaverine and Am.
5. lotusine suppresses PDE, improves cAMP in the thrombocyte, cGMP content.
Conclusion: lotusine is that PDE III (shows that it has Ca
++Sensitization) and/or the V-type inhibitor.
Experiment and result:
Lot is to the influence of myocardial contraction
1. to guinea pig left atrium and the musculotonic influence of corpora mammillaria
On guinea pig left atrium and papillary muscle sample, but Lot1-300 μ mol/L concentration dependent ground increases convergent force, and 3,300 μ mol/L make the left atrium convergent force increase by 19% and 84% respectively, makes the papillary muscle convergent force increase by 21% and 91%.Under the same experiment condition, Am 1-300 μ mol/L also concentration dependent ground increases convergent force, and 3,300 μ mol/L make the left atrium convergent force increase by 9% and 58% respectively.The effect that shows Lot obviously is better than Am.
Table 1; Lotusine and amrinone are received guinea pig left atrium and lotusine guinea pig papillary muscle
The influence of the power that contracts (x ± SD), (n=7～9)
Lotusine (μ mol/L)
Contrast 13 10 30 100 300 guinea pig left atrium convergent forces (mg) 445 ± 95 495 ± 140 530 ± 135 590 ± 105 645 ± 120 771 ± 141 823 ± 199 and increase (%) 0 11 ± 4 19 ± 5 33 ± 6 45 ± 14 73 ± 18 84 ± 14Gpla (n=9) guinea pig papillary muscle convergent force (mg) 301 ± 75 340 ± 37 365 ± 31 420 ± 57 470 ± 80 545 ± 78 578 ± 113 increase (%) 09 ± 4 21 ± 5 39 ± 7 56 ± 12 81 ± 14 91 ± 15Gpc (n=7)
Amrinone (μ mol/L)
Contrast 13 10 30 100 300 guinea pig left atrium convergent forces (mg) 421 ± 81 432 ± 89 459 ± 96 501 ± 98 589 ± 101 629 ± 108 657 ± 114 and increase (%) 03 ± 39 ± 4 19 ± 8 40 ± 9 49 ± 11 58 ± 13
2. to rat left atrium and the musculotonic influence of cat corpora mammillaria
On the sample of rat left atrium, but lotusine 1-300 μ mol/L concentration dependent ground increases convergent force, and 3,300 μ mol/L make the left atrium convergent force increase by 23% and 94% respectively.On cat papillary muscle sample, but the same concentration dependent ground of lotusine 1-300mol/L increases convergent force, and 3,300 μ mol/L make convergent force increase by 21% and 117% respectively.
Table 2: lotusine to the rat left atrium (on) and the influence of cat papillary muscle (descending) convergent force
(x±SD)，(n＝6～7)
Lotusine (μ mol/L)
Contrast 13 10 30 100 300 rat left atrium convergent forces, (mg) 487 ± 98 514 ± 91 602 ± 112 693 ± 154 756 ± 196 875 ± 238 945 ± 243 increase, (%) 0 5.5 ± 4 23 ± 5 42 ± 6 55 ± 11 80 ± 18 94 ± 12 cat papillary muscles increase, (%) 07 ± 5 13 ± 6 21 ± 11 47 ± 13 84 ± 22 117 ± 32
Amrinone (μ mol/L)
Contrast 13 10 30 100 rat atrium sinistrum convergent forces (mg) 463 ± 31 471 ± 33 490 ± 45 511 ± 61 562 ± 57 616 ± 64 and increase (%) 02 ± 26 ± 4 11 ± 8 21 ± 7 33 ± 9Ratln (n=6) cat papillary muscle convergent force (mg) 352 ± 44 363 ± 37 387 ± 43 412 ± 41 472 ± 48 528 ± 61 increase (%) 03 ± 4 10 ± 4 17 ± 7 34 ± 11 51 ± 12Ratc (n=6)
3. to the musculotonic influence of reserpinization cavy shape
Handling through reserpinization in advance
[9](5mg/kg, abdominal injection prepare sample behind the 24h) or handle on the guinea pig papillary muscle sample, but the equal concentration dependent ground increase convergent force of lotusine 1-100 μ mol/L without reserpinization.But with compare without the reserpinization treatment group, lotusine increases the musculotonic dose-effect curve of reserpinization cavy shape and obviously moves to right and force down; 100 μ mol/L lotusines increase myodyamia effect, by reducing to through 51% of reserpinization treatment group without 83% of reserpinization treatment group.The positive inotropic action of prompting lotusine is relevant with the noradrenergic nerve mediator.Under the same experiment condition, the ground influence of Papaverine 1-100 μ mol/L two-phase without or the guinea pig papillary muscle convergent force handled through reserpinization, the former graded effect curve is presented raises earlier and afterwards reduces, and make the latter present earlier slightly liter inhibition then, even be lower than the preceding level of administration.Table 3: lotusine to the musculotonic influence of reserpinization cavy shape (x ± SD, n=8)
Increase convergent force without reserpinization through reserpinization medicine convergent force and increase (μ mol/L) (mg) (Δ %) (mg) (Δ %) lotusine 0 209 ± 48 0 233 ± 56 0
10 270±50 29 252±60 8
30 318±90 52 294±61 26
100 382 ± 63 83 353 ± 78 51 Papaverine 0 230 ± 56 0 218 ± 40 0
10 274±81 19 224±30 3
30 282±80 23 245±86 12
186±68 -15
4. the animal species selectivity ratios of lotusine positive inotropic action
Compare the Lot positive inotropic action as seen, 30 μ mol/L Lot make cavy, rat and rabbit left atrium convergent force increase by 45%, 55% and 51% respectively; Make cavy, rat and cat papillary muscle convergent force increase by 56%, 53% and 47% respectively.Show that the Lot positive inotropic action there is no animal species selectivity significantly.
Table 4: lotusine 30 (μ mol/L) positive inotropic action animal species choosing
The comparison of selecting property (n=5～9, x ± SD)
The sample muscular strength increases (%)
Guinea pig left atrium 45 ± 14
Rat left atrium 55 ± 11
Rabbit left atrium 51 ± 18
Guinea pig papillary muscle 56 ± 12
Rat papillary muscle 53 ± 13
Cat papillary muscle 47 ± 13
Lotusine to amrinone, Papaverine, Lema (Lemakalim, Lei Makalin), the influence of the positive flesh effect of Racemic isoproterenol and with the interaction of Proprasylyte
On guinea pig left atrium and papillary muscle sample, amrinone 30 μ mol/L slightly increase myocardial contraction, give lotusine 30 μ mol/L on this basis again, and the increase of myocardial contraction is obviously high and single with amrinone or lotusine group, points out both that summation action is arranged.Equally, on guinea pig left atrium flesh sample, handling with Papaverine 30 μ mol/L in advance, give lotusine 30 μ mol/L again, myocardial contraction obviously increases.
On the guinea pig left atrium sample, with Lama 10 μ mol/L muscular strength is obviously descended in advance, the negative flesh that gives the turning Lama of lotusine 100 μ mol/L again act as positive flesh effect.
On the guinea pig left atrium sample, handle with lotusine 30 μ mol/L in advance, give Racemic isoproterenol again, make concentration-effect curve.Lotusine slightly makes the Racemic isoproterenol concentration-effect curve move to left, and maximum reaction is constant.
On the guinea pig left atrium sample of handling with Proprasylyte 0.1 μ mol/L in advance, give lotusine again, Proprasylyte is antagonism or cancel the positive flesh effect of lotusine significantly.
Table 5: Papaverine, amrinone, Lama are to the influence of the positive flesh effect of lotusine
(n＝6～9，x±SD)
Medicine (μ mol/L) convergent force (mg) increases (%)
0 431±105 0
Papaverine 30 564 ± 165 31
Papaverine+lotusine 735 ± 175 71
0 420±92 0
Amrinone 30 589 ± 108 40
Amrinone+lotusine 773 ± 139 83
0 413±87 0
Lama 30 302±79 -27
Lama+ lotusine 100 528 ± 102+28
6. frequency of stimulation is to the influence of the positive flesh effect of lotusine
On the guinea pig left atrium sample, Bay K8644 10nmol/L positive inotropic action speeds and increases with frequency of stimulation (0.25-2Hz), is frequency dependence
[10]And the positive flesh effect of lotusine 100 μ mol/L is only in rising trend when low frequency stimulates, but downtrending when high frequency stimulates.Also visible similar phenomenon on the guinea pig papillary muscle sample.
7. lotusine is to the influence of right atrium from the frequency of fighting
On cavy and rat right atrium sample, lotusine 1-300 μ mol/L slightly speeds the right atrium from the frequency of fighting, but does not have the significance meaning.On the Resization guinea pig right atrium sample, Lot does not still speed the right atrium from fighting frequency (n=5, p＞0.05).
Table 6: the lotusine right atrium is from influence (n=5～7, the X ± SD) of the frequency of fighting
Heart rate (inferior/minute) lotusine (μ mol/L cavy rat
0 192±21 179±11
1 188±20 177±9
3 187±22 177±8 10 190±17 178±7 30 193±18 180±5 100 192±18 179±10 300 195±20 183±12
8. the influence of lotusine isolated heart function
On the isolated working heart lung preparation, through left atrium perfusion intubate, single dose (10mmol/L, 0.2ml) give lotusine (final concentration is 20 μ mol/L), 0.5min after, left ventricular pressure (LVP), left ventricle contraction rate (+dp/dt) and the left ventricle relaxation rate (dp/dt) increase (increasing of dp/dt negative value); Coronary flow (CO) and aorta flow (MAO) slightly increase and heart rate constant (p＞0.05).
Claims (3)
1. preparation method who from Plumula Nelumbinis, extracts LOTUSINE, comprising: (1) is raw material with the Plumula Nelumbinis, produces the water-soluble biological total alkali; It is characterized in that (2) separating water-soluble total alkaloids gets the crystallization of crude product total alkali; (3) the crude product total alkali crystallization that the separating water-soluble total alkaloids is made is respectively at periodic crystallisation in dehydrated alcohol and the water, fractional crystallization in the ethanol gets white prismatic crystal, adds saturated bariumchloride in the aqueous solution, the filtering precipitation, recrystallization gets the lotusine hydrochloride in the dehydrated alcohol.
2. a kind of preparation method who from Plumula Nelumbinis, extracts LOTUSINE according to claim 1, it is characterized in that said is raw material with the Plumula Nelumbinis, the method of producing the water-soluble biological total alkali is: the Plumula Nelumbinis crude drug is soaked 3 times with methyl alcohol, reclaim methyl alcohol and get total alkali medicinal extract, regulate pH to 2-3 with 1% aqueous hydrochloric acid, filter, get acid total alkaline solution.
3. according to claim 1,2 described a kind of preparation methods that from Plumula Nelumbinis, extract LOTUSINE, the method that it is characterized in that said separating water-soluble total alkaloids is: will be the water-soluble biological total alkali that raw material is produced with the Plumula Nelumbinis, promptly acid total alkaline solution, regulate pH to 9-10 with strong aqua, get alkaline total alkali precipitation, suspension, again with chloroform extraction 5 times, keep alkaline water layer, regulate pH to 2-3, add saturated ammonium tetrathiocyanodiaminochromate, fully precipitation, the leaching throw out, air-dry, be dissolved in acetone, the filtering insolubles; Add saturated sulfuric acid silvering solution in the acetone solution, fully precipitate, the filtering throw out reclaims acetone, is evaporated to syrupy shape, and crystallization gets thick total alkali crystallization.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN98121705A CN1117734C (en) | 1998-12-14 | 1998-12-14 | Process for extracting lotucine from plumula nelumbinis |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN98121705A CN1117734C (en) | 1998-12-14 | 1998-12-14 | Process for extracting lotucine from plumula nelumbinis |
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| Publication Number | Publication Date |
|---|---|
| CN1257069A CN1257069A (en) | 2000-06-21 |
| CN1117734C true CN1117734C (en) | 2003-08-13 |
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|---|---|---|---|
| CN98121705A Expired - Fee Related CN1117734C (en) | 1998-12-14 | 1998-12-14 | Process for extracting lotucine from plumula nelumbinis |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112755036A (en) * | 2019-10-21 | 2021-05-07 | 朱敏生 | Agent for altering smooth muscle properties by modulating MYPT1 and uses thereof |
| CN110786341B (en) * | 2019-11-15 | 2021-04-06 | 中南民族大学 | Preparation method and application of lotus plumule extracting solution |
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1998
- 1998-12-14 CN CN98121705A patent/CN1117734C/en not_active Expired - Fee Related
Non-Patent Citations (4)
| Title |
|---|
| 中国中药杂志1991年第16卷第11期 1991-01-01 王嘉陵等:莲子心中生物碱成分的研究 * |
| 中草药1984年第15卷第7期 1984-01-01 郭毛娣，陈兰贵,中国大陆产莲子心中生物碱成分的研究 * |
| 山西林业科技1997年第1期 1997-01-01 马养民，傅建熙生物碱的研究概况 * |
| 山西林业科技1997年第1期 1997-01-01 马养民，傅建熙生物碱的研究概况;中草药1984年第15卷第7期 1984-01-01 郭毛娣，陈兰贵,中国大陆产莲子心中生物碱成分的研究;中国中药杂志1991年第16卷第11期 1991-01-01 王嘉陵等:莲子心中生物碱成分的研究 * |
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