CN104628736B - A kind of method extracting galantamine from lycoris plants - Google Patents
A kind of method extracting galantamine from lycoris plants Download PDFInfo
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- CN104628736B CN104628736B CN201510066820.5A CN201510066820A CN104628736B CN 104628736 B CN104628736 B CN 104628736B CN 201510066820 A CN201510066820 A CN 201510066820A CN 104628736 B CN104628736 B CN 104628736B
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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Abstract
A kind of method extracting galantamine from lycoris plants, comprises the following steps：(1) extract：Weigh treated Bulbus Lycoridis Radiatae powder, with solid-liquid ratio 1:10, unit ratio is g/mL, adds pH to be in 4.5 water, adds the cellulase of Bulbus Lycoridis Radiatae powder quality 1.0% 3.0% and the mixed enzyme of pectase, and described cellulase is 1 with the mass ratio of pectase:1, digest 20 100min at 50 DEG C, then ultrasonic Treatment 5 25min, 5000r/min is centrifuged 20min, takes supernatant to obtain final product galantamine extracting solution；(2) purification：1. solvent extraction；2. cationic exchange resin adsorption；③C18Reversed-phase silica gel column chromatography；4. normal-phase silica gel column chromatography；5. recrystallization：By step, 4. gained dried object III dissolves through ethanol, and recrystallization obtains galantamine crude product, filters, is vacuum dried to obtain galantamine at 50～60 DEG C.The present invention is simple to operate, and extraction time is short, extraction ratio is high, solvent load is few, cost is relatively low；Purifying process environmental protection, and purity is high, up to 99.2%.
Description
Technical field
The present invention relates to a kind of extracting method of galantamine, especially relate to a kind of extraction Garland from lycoris plants
His quick method.
Background technology
In Bulbus Lycoridis Radiatae, the chemical synthesis process of the alkaloid such as galantamine has had been reported that, but extracts still from lycoris plants
It is big important sources of such material, in prior art, the extracting method of maryllidaceous alkaloid mainly has solvent extraction method, ultrasonic
The methods such as ripple extraction method, microwave loss mechanisms, supercritical fluid extraction, these methods are usually present that environmental pollution is serious, produce
The shortcomings of high cost.
Content of the invention
The technical problem to be solved is that the drawbacks described above overcoming prior art to exist, when providing a kind of extraction
Between short, solvent load is few, extraction ratio is high, low cost from lycoris plants extract galantamine method.
The technical solution adopted for the present invention to solve the technical problems is that one kind extracts galantamine from lycoris plants
Method, comprise the following steps：
(1) extract：Weigh treated Bulbus Lycoridis Radiatae powder, with solid-liquid ratio 1:10, unit ratio is g/mL, adds pH to be 4.5
Water in, add Bulbus Lycoridis Radiatae powder quality 1.0%-3.0% (preferably 2.0%-2.8%, more preferably 2.5%) cellulase with fruit
The mixed enzyme of glue enzyme, described cellulase is 1 with the mass ratio of pectase:1, digest 20-100min (preferably 40- at 50 DEG C
80min, more preferably 60min), then ultrasonic Treatment 5-25min (preferably 15min-20min, more preferably 15min), 5000r/
Min is centrifuged 20min, takes supernatant to obtain final product galantamine extracting solution；
(2) purification
1. solvent extraction：The galantamine extracting solution NaOH that step (1) is extracted adjusts pH to 10, and by volume 1:1
Add extractant chloroform, shake up, stand overnight, take off a layer chloroform phase, HCl adjusts pH to 2, sucking filtration, obtain galantamine extraction
Take concentrated solution；
2. cationic exchange resin adsorption：By step, 1. middle extraction concentrated solution adjusts pH to 1～6 (preferably pH is 2) through HCl
With D-001 type cation exchange resin, with loading speed 1-3BV/h (preferably 3BV/h) loading to saturation, with containing 0.5-
40%-80% (preferably 70%) ethanol solution of 2.5mol/L (preferably 1.5mol/L) ammonia is carried out with the elution rate of 3BV/h
Eluting, is dried, obtains dried object I；
③C18Reversed-phase silica gel column chromatography：C18Filler pre-treatment, by 20 times of quality in the C of step 2. middle dried object I18Filler
It is loaded in chromatographic column, then with mobile phase (mobile phase：V (acetonitrile) V (phosphate) is 16 84) chromatography that separates out of dissolving layer
Thing, loading, using methanol-water solution gradation eluting, collect eluent, concentrate, vacuum lyophilization, obtain dried object II；
4. normal-phase silica gel column chromatography：With pretreated 20 times of quality in the column chromatography silicon of step 3. gained dried object II
With column diameter-pillar height wet method dress post, the ratio of described column diameter-pillar height is 1 to glue (200-300 mesh):10～30 (preferably 1:10),
3. gained dried object II and silica gel mix step, add eluant dissolving, described eluant is petroleum ether, ethyl acetate, chloroform,
Two kinds of solvent mixing in acetone, methanol；Dry method loading after evaporation solvent, eluting, collect eluent, concentrate, vacuum freezing is done
Dry, obtain dried object III；
5. recrystallization：By step, 4. gained dried object III dissolves through ethanol, and recrystallization obtains galantamine crude product, filters,
It is vacuum dried to obtain galantamine at 50～60 DEG C.
Further, described step 4. in, eluant is petroleum ether and ethyl acetate, the body of described ethyl acetate and petroleum ether
Long-pending ratio is 8.4:1.6.
Further, described lycoris plants are that Lycoris aurea, Lycoris radiata, Flos Rosae Rugosae Bulbus Lycoridis Radiatae, Caulis et Folium Oryzae Bulbus Lycoridis Radiatae or Lycoris are (excellent
Select Lycoris aurea).
Further, the preferred Lycoris aurea bulb powder of described Bulbus Lycoridis Radiatae powder.
Compared with prior art, the present invention is simple to operate, and extraction time is short, extraction ratio is high, extraction time is few, solvent load
Less, cost is relatively low, and using ultrasonic synergistic Enzymatic Extraction, galantamine yield is 0.02840%；Purifying process environmental protection, and pure
Degree is high, up to 99.2%.
Brief description
Fig. 1 is the impact schematic diagram to galantamine yield for the enzyme dosage of the present invention；
Fig. 2 is the impact schematic diagram to galantamine yield for the enzymolysis time of the present invention；
Fig. 3 is the impact schematic diagram to galantamine yield for the ultrasonic time of the present invention.
Specific embodiment
Below in conjunction with drawings and Examples, the present invention will be further described.
Embodiment 1
The present embodiment comprises the following steps：Accurately weigh treated Bulbus Lycoridis Radiatae powder 2.0g, with solid-liquid ratio 1:10, unit is
G/mL, adds pH to be the mixed enzyme with pectase for the cellulase being separately added into raw materials quality 1.0%-3.0% in 4.5 water,
Digest 20-100min, then ultrasonic Treatment 5-25min at 50 DEG C, 5000r/min is centrifuged 20min, takes supernatant, obtains final product
Galantamine extracting solution；
(2) purification
1. solvent extraction：The galantamine extracting solution NaOH that step (1) is extracted adjusts pH to 10, and by volume 1:1
Add extractant chloroform, shake up, stand overnight, take off a layer chloroform phase, HCl adjusts pH to 2, sucking filtration, obtain galantamine extraction
Take concentrated solution；
2. cationic exchange resin adsorption：By step 1. middle extraction concentrated solution through HCl adjust pH be 2, with D-001 type sun from
Sub-exchange resin, with loading speed 3BV/h loading to saturation, with 70% ethanol solution containing 1.5mol/L ammonia with 3BV/h's
Elution rate carries out eluting, is dried, obtains dried object I；
③C18Reversed-phase silica gel column chromatography：C18Filler pre-treatment, by 20 times of quality in the C of step 2. middle dried object I18Filler
It is loaded in chromatographic column, then with mobile phase (mobile phase：V (acetonitrile) V (phosphate) is 16 84) chromatography that separates out of dissolving layer
Thing, loading, using methanol-water solution gradation eluting, collect eluent, concentrate, vacuum lyophilization, obtain dried object II；
4. normal-phase silica gel column chromatography：With pretreated 20 times of quality in the column chromatography silicon of step 3. gained dried object II
With column diameter-pillar height wet method dress post, the ratio of described column diameter-pillar height is 1 to glue (200-300 mesh):10,3. gained is dried step
Thing II is mixed with silica gel, adds eluant dissolving, and described eluant is petroleum ether, in ethyl acetate, chloroform, acetone, methanol
Two kinds of solvent mixing；Dry method loading after evaporation solvent, eluting, collect eluent, concentrate, vacuum lyophilization, obtain dried object III；
5. recrystallization：By step, 4. gained dried object III dissolves through ethanol, and recrystallization obtains galantamine crude product, filters,
50～60 DEG C be vacuum dried purity be 99.2% galantamine.
Step 4. in, eluant is petroleum ether and ethyl acetate, and the volume ratio of described ethyl acetate and petroleum ether is 8.4:
1.6.
Referring to the drawings 1, the impact situation of enzyme dosage, accurately weigh treated Bulbus Lycoridis Radiatae powder 2.000g, add pH to be 4.5
Water 20mL, be separately added into the mixed of the cellulase of raw materials quality 1.0%, 1.5%, 2.0%, 2.5%, 3.0% and pectase
Synthase, digests 1h, supersound process 15min, 5000r/min is centrifuged 20min, takes supernatant, is settled to 50mL at 50 DEG C.Result
Display, in the range of 1%-2.5%, galantamine yield raises with the increase of enzyme dosage, enzyme dosage be 2.5% effect
Good.
Referring to the drawings 2, the impact of enzymolysis time, weigh Bulbus Lycoridis Radiatae powder 2.000g, add the water 20mL that pH is 4.5, add
The cellulase of raw materials quality 2.0% and the mixed enzyme of pectase, at 50 DEG C enzymolysis 20,40,60,80,100min, ultrasonic place
Reason 15min, 5000r/min are centrifuged 20min, take supernatant, be settled to 50mL.Result understand, enzymolysis time in 20-60min,
Galantamine yield increases in time and raises, and slightly reduces afterwards.60min best results.
Referring to the drawings 3, the impact of ultrasonic time, weigh Bulbus Lycoridis Radiatae powder 2.000g, add the water 20mL that pH is 4.5, add
The cellulase of raw materials quality 2.0% and the mixed enzyme of pectase, 50 DEG C of enzymolysis 1h, then supersound process 5,10,15,20,
25min, 5000r/min are centrifuged 20min, take supernatant, are settled to 50mL, galantamine yield is in 5-15min with ultrasonic place
The growth of reason time and increase, reach maximum during 15min.
With galantamine yield as index, intuitively analyzed and be shown in Table 1, table 2 with the results of analysis of variance.
Table 1 ultrasonic synergistic Enzymatic Extraction galantamine orthogonal design and result
Table 2 ultrasonic synergistic Enzymatic Extraction galantamine variance analyses
| Soruces of variation | Deviation square | Degree of freedom | Mean square | F value | P value |
| A | 7.152 | 2 | 3.576 | 12.460 | ＜ 0.1 |
| B | 15.107 | 2 | 7.554 | 26.319 | ＜ 0.05 |
| C | 13.105 | 2 | 6.552 | 22.831 | ＜ 0.05 |
| Error | 0.57 | ||||
| Summation | 35.934 |
Intuitively analyzed by table 1 it is known that galantamine optimum extraction process is A2B2C1.According to variance analyses (table 2), enzyme
Solution time, the impact to galantamine yield for the ultrasonic time are notable (P ＜ 0.05)；Enzyme dosage has an impact to the extraction of galantamine
(P ＜ 0.1).Each factor primary and secondary order of impact galantamine yield is enzymolysis time ＞ ultrasonic time ＞ enzyme dosage.Ultrasound wave
The optimal procedure parameters of collaborative Enzymatic Extraction galantamine are enzymolysis time 1.0h, ultrasonic time 10min, enzyme dosage 2.5%.
It is 0.02840% in this Optimal technique process galantamine yield.
Comparative example is 1.
Ultrasonic assistant extracts galantamine in Bulbus Lycoridis Radiatae：Using 0.5% H2SO4Aqueous solution, solid-liquid ratio 1:10(g:ML),
Extraction 2.5h and then ultrasonic treatment time 30min under 70 DEG C of water-baths, extract 2 times with this understanding, and galantamine yield is
0.02530%.
Compared with Example 1, galantamine yield is low.
Comparative example is 2.
Galantamine in Enzymatic Extraction Bulbus Lycoridis Radiatae：With solid-liquid ratio 1:10(g:ML) add pH to be in 4.5 water, add 4%
Cellulase and pectase mixed enzyme digest 2h under 50 DEG C of water-baths, extract 2 times with this understanding, and galantamine yield is
0.02940%.
Compared with Example 1, though embodiment 1 galantamine yield is lower than the present embodiment enzymatic isolation method by 3.42%, implement
Example 1 extract enzyme dosage be the 62.5% of simple enzymatic isolation method, enzymolysis time only has the 1/2 of the present embodiment enzymatic isolation method, therefore from
From the point of view of economy, embodiment 1 carries out galantamine extraction and has bigger advantage.
Claims (6)
1. a kind of method of galantamine of extracting from lycoris plants is it is characterised in that comprise the following steps：
(1) extract：Weigh treated lycoris plants powder, with solid-liquid ratio 1:10, unit ratio is g/mL, and addition pH is
In 4.5 water, add the cellulase of lycoris plants powder quality 1.0%-3.0% and the mixed enzyme of pectase, described fibre
The plain enzyme of dimension is 1 with the mass ratio of pectase:1, enzymolysis 20-100min at 50 DEG C, then ultrasonic Treatment 5-25min,
5000r/min is centrifuged 20min, takes supernatant to obtain final product galantamine extracting solution；
(2) purification：
1. solvent extraction：The galantamine extracting solution NaOH that step (1) is extracted adjusts pH to 10, and by volume 1:1 addition
Extractant chloroform, shakes up, and stands overnight, and takes off a layer chloroform phase, and HCl adjusts pH to 2, sucking filtration, obtains galantamine extraction dense
Contracting liquid；
2. cationic exchange resin adsorption：By step 1. middle extraction concentrated solution through HCl adjust pH to 1～6, with D-001 type sun from
Sub-exchange resin, with loading speed 1-3BV/h loading to saturation, molten with the 40%-80% ethanol containing 0.5-2.5mol/L ammonia
Liquid carries out eluting with the elution rate of 3BV/h, is dried, obtains dried object I；
③C18Reversed-phase silica gel column chromatography：C18Filler pre-treatment, by 20 times of quality in the C of step 2. middle dried object I18Filler is loaded on
In chromatographic column, the chromatography thing that then separated out with mobile phase dissolving layer, loading, using methanol-water solution gradation eluting, collection is washed
De- liquid, concentrates, vacuum lyophilization, obtains dried object II；
4. normal-phase silica gel column chromatography：With pretreated 20 times of quality in step 3. gained dried object II column chromatography silica gel with
Column diameter-pillar height wet method dress post, the ratio of described column diameter-pillar height is 1:10～30, step 3. gained dried object II and silica gel
Mix, add eluant dissolving, described eluant is petroleum ether, ethyl acetate, chloroform, acetone, two kinds of solvents in methanol mix
Close；Dry method loading after evaporation solvent, eluting, collect eluent, concentrate, vacuum lyophilization, obtain dried object III；
5. recrystallization：By step, 4. gained dried object III dissolves through ethanol, and recrystallization obtains galantamine crude product, filters, 50
～60 DEG C are vacuum dried to obtain galantamine.
2. according to claim 1 from lycoris plants extract galantamine method it is characterised in that include below
Step：
(1) extract：Weigh treated lycoris plants powder, with solid-liquid ratio 1:10, unit ratio is g/mL, and addition pH is
In 4.5 water, add the cellulase of lycoris plants powder quality 2.0%-2.8% and the mixed enzyme of pectase, described fibre
The plain enzyme of dimension is 1 with the mass ratio of pectase:1, digest 40-80min, then ultrasonic Treatment 5-25min, 5000r/ at 50 DEG C
Min is centrifuged 20min, takes supernatant to obtain final product galantamine extracting solution；
(2) purification
1. solvent extraction：The galantamine extracting solution NaOH that step (1) is extracted adjusts pH to 10, and by volume 1:1 addition
Extractant chloroform, shakes up, and stands overnight, and takes off a layer chloroform phase, and HCl adjusts pH to 2, sucking filtration, obtains galantamine extraction dense
Contracting liquid；
2. cationic exchange resin adsorption：By step, 1. middle extraction concentrated solution adjusts pH to 2 through HCl, is handed over D-001 type cation
Change resin, with loading speed 3BV/h loading to saturation, with 70% ethanol solution containing 1.5mol/L ammonia with the eluting of 3BV/h
Speed carries out eluting, is dried, obtains dried object I；
③C18Reversed-phase silica gel column chromatography：C18Filler pre-treatment, by 20 times of quality in the C of step 2. middle dried object I18Filler is loaded on
In chromatographic column, the chromatography thing that then separated out with mobile phase dissolving layer, loading, using methanol-water solution gradation eluting, collection is washed
De- liquid, concentrates, vacuum lyophilization, obtains dried object II；
4. normal-phase silica gel column chromatography：With pretreated 20 times of quality in step 3. gained dried object II column chromatography silica gel with
Column diameter-pillar height wet method dress post, the ratio of described column diameter-pillar height is 1:10,3. gained dried object II and silica gel mix step,
Add eluant dissolving, described eluant is petroleum ether, ethyl acetate, chloroform, acetone, two kinds of solvents mixing in methanol；Steam
Send out dry method loading after solvent, eluting, collect eluent, concentrate, vacuum lyophilization, obtain dried object III；
5. recrystallization：By step, 4. gained dried object III dissolves through ethanol, and recrystallization obtains galantamine crude product, filters, 50
～60 DEG C are vacuum dried to obtain galantamine.
3. the method for galantamine of extracting from lycoris plants according to claim 1 and 2 is it is characterised in that described
Step 4. in, eluant is petroleum ether and ethyl acetate, and the volume ratio of described ethyl acetate and petroleum ether is 8.4:1.6.
4. the method for galantamine of extracting from lycoris plants according to claim 1 and 2 is it is characterised in that described
Lycoris plants are Lycoris aurea, Lycoris radiata, Flos Rosae Rugosae Bulbus Lycoridis Radiatae, Caulis et Folium Oryzae Bulbus Lycoridis Radiatae or Lycoris.
5. the method for galantamine of extracting from lycoris plants according to claim 4 is it is characterised in that described Bulbus Lycoridis Radiatae
Platymiscium is Lycoris aurea.
6. the method extracting galantamine from lycoris plants according to claim 1 or 2 any one, its feature exists
In described lycoris plants powder is Lycoris aurea bulb powder.
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| CN106967080A (en) * | 2017-04-10 | 2017-07-21 | 吉首大学 | A kind of method that galanthamine is extracted from short-tube lycoris |
| CN107462656A (en) * | 2017-07-04 | 2017-12-12 | 上海市农业科学院 | A kind of method of galanthamine content in quick detection amrallid |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101704822A (en) * | 2009-10-20 | 2010-05-12 | 南京荣世医药科技有限公司 | Method for preparing galanthamine |
| CN101781305A (en) * | 2010-03-23 | 2010-07-21 | 泰州市今朝伟业精细化工有限公司 | Method for artificially synthesizing galanthamine |
| CN101157947B (en) * | 2007-09-13 | 2011-04-20 | 华中科技大学 | Method for extracting active alkaloid from lycoris herb |
| CN103772403A (en) * | 2014-02-27 | 2014-05-07 | 湖南中医药大学 | Method for extracting galanthamine by using lycoris aurea |
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- 2015-02-07 CN CN201510066820.5A patent/CN104628736B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101157947B (en) * | 2007-09-13 | 2011-04-20 | 华中科技大学 | Method for extracting active alkaloid from lycoris herb |
| CN101704822A (en) * | 2009-10-20 | 2010-05-12 | 南京荣世医药科技有限公司 | Method for preparing galanthamine |
| CN101781305A (en) * | 2010-03-23 | 2010-07-21 | 泰州市今朝伟业精细化工有限公司 | Method for artificially synthesizing galanthamine |
| CN103772403A (en) * | 2014-02-27 | 2014-05-07 | 湖南中医药大学 | Method for extracting galanthamine by using lycoris aurea |
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