CN104672245B - A kind of method extracting monomer lycorine from lycoris plants - Google Patents
A kind of method extracting monomer lycorine from lycoris plants Download PDFInfo
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- CN104672245B CN104672245B CN201510066563.5A CN201510066563A CN104672245B CN 104672245 B CN104672245 B CN 104672245B CN 201510066563 A CN201510066563 A CN 201510066563A CN 104672245 B CN104672245 B CN 104672245B
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- C07—ORGANIC CHEMISTRY
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- 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
- C07D491/12—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 three hetero rings
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Abstract
A kind of method extracting lycorine monomer from lycoris plants, comprises the following steps：(1) extract：Weigh treated Bulbus Lycoridis Radiatae powder, with solid-liquid ratio 1:10, proportional units are g/mL, add pH to be in 4.5 water, add 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, obtains final product Bulbus Lycoridis Radiatae alkali 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 is vacuum dried to obtain lycorine monomer at 50～60 DEG C.The present invention is simple to operate, and extraction time is short, extraction ratio is high, consumption of organic solvent is few, cost is relatively low, and using ultrasonic synergistic Enzymatic Extraction, lycorine yield is 0.1812%；Extraction and purification process environmental protection, and purity is high, up to 99.4%.
Description
Technical field
The present invention relates to a kind of extracting method of lycorine, especially relate to a kind of extraction lycorine from lycoris plants
The method of monomer.
Background technology
In Bulbus Lycoridis Radiatae, the chemical synthesis process of the alkaloid such as lycorine has had been reported that, but extraction is still from lycoris plants
One big important sources of such material, in prior art, the extracting method of maryllidaceous alkaloid mainly has solvent extraction method, ultrasound wave
The methods such as extraction method, microwave loss mechanisms, supercritical fluid extraction, these methods are usually present that environmental pollution is serious, produce into
The shortcomings of this is high.
Chinese patent 2008102047350 discloses a kind of extraction separation method of lycorine in Bulbus Lycoridis Radiatae, with Bulbus Lycoridis Radiatae bulb
For raw material, using compound enzyme pretreatment, dilute hydrochloric acid extracts, and ultrasonic assistant extracts, and chloroform extraction methods extract lycorine.Though carrying
The high extraction ratio of lycorine, but extract is not lycorine monomer, and step is complicated, complex operation.Lack to Bulbus Lycoridis Radiatae at present
The extraction of alkali monomer.
Chinese patent 2007100532075 discloses a kind of method extracting active alkaloid from lycoris plants, raw
Alkaloids purification is strong and weak different according to maryllidaceous alkaloid alkalescence, synchronously obtains multiple maryllidaceous alkaloids using stage extraction technology and slightly produces
Product, then through column chromatography and it is recrystallizing repeatedly so as to obtain highly purified maryllidaceous alkaloid monomer (galantamine, lycorine, Li Kela
Quick, Sekisanine), and the organic solvent extracting be the chloroform of 0.5-3 times of volume, n-butyl alcohol, petroleum ether, ethyl acetate,
One of ether and isoamyl alcohol, though this invention improves Bulbus Lycoridis Radiatae overall availability, complex operation, organic solvent content
Height, pollutes environment.
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, environmental protection from lycoris plants extract lycorine monomer method.
The technical solution adopted for the present invention to solve the technical problems is that one kind extracts lycorine list from lycoris plants
The method of body, comprises the following steps：
(1) extract：Weigh treated Bulbus Lycoridis Radiatae powder, with solid-liquid ratio 1:10, proportional units are g/mL, add 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, obtains final product Bulbus Lycoridis Radiatae alkali extracting solution；
(2) purification
1. solvent extraction：The Bulbus Lycoridis Radiatae alkali extracting solution NaOH that step (1) is extracted adjusts pH to 10, and by volume 1:1 adds
Enter extractant chloroform, shake up, stand overnight, take off a layer chloroform phase, HCl adjusts pH to 2, sucking filtration, obtain lycorine extraction dense
Contracting liquid；
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 lycorine crude product, filters,
50～60 DEG C of vacuum drying lycorine monomers.
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 Lycoris radiata or Caulis et Folium Oryzae Bulbus Lycoridis Radiatae.
Further, described lycoris plants powder is Lycoris radiata bulb powder.
Compared with prior art, the present invention is simple to operate, extraction time is short, extraction ratio is high, solvent load is few, cost relatively
Low, using ultrasonic synergistic Enzymatic Extraction, lycorine yield is 0.1812%；Purifying process environmental protection, and purity is high, up to
99.4%.
Brief description
Fig. 1 is the impact schematic diagram to lycorine yield for the enzyme dosage of the present invention；
Fig. 2 is the impact schematic diagram to lycorine yield for the enzymolysis time of the present invention；
Fig. 3 is the impact to lycorine 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：(1) extract：Weigh treated Bulbus Lycoridis Radiatae powder, with solid-liquid ratio 1:10, ratio list
Position 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 of pectase
Synthase, described cellulase is 1 with the mass ratio of pectase:1, digest 20-100min, then ultrasonic Treatment 5- at 50 DEG C
25min, 5000r/min are centrifuged 20min, take supernatant, obtain final product Bulbus Lycoridis Radiatae alkali extracting solution；
(2) purification
1. solvent extraction：The Bulbus Lycoridis Radiatae alkali extracting solution NaOH that step (1) is extracted adjusts pH to 10, and by volume 1:1 adds
Enter extractant chloroform, shake up, stand overnight, take off a layer chloroform phase, HCl adjusts pH to 2, sucking filtration, obtain lycorine extraction dense
Contracting liquid；
2. cationic exchange resin adsorption：By step 1. middle extraction concentrated solution through HCl adjust pH to 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 and ethyl acetate, described ethyl acetate and oil
The volume ratio of ether is 8.4:1.6；Dry method loading after evaporation solvent, eluting, collect eluent, concentrate, vacuum lyophilization, obtain dry
Dry thing III；
5. recrystallization：By step, 4. gained dried object III dissolves through ethanol, and recrystallization obtains lycorine crude product, filters,
50～60 DEG C be vacuum dried purity be 99.4% lycorine monomer.
Lycoris plants powder is Lycoris radiata bulb powder.
Referring to the drawings 1, the impact situation of enzyme dosage, weigh treated Bulbus Lycoridis Radiatae powder 2.000g, add the water that pH is 4.5
20mL, adds the cellulase of Bulbus Lycoridis Radiatae powder quality 1.0%, 1.5%, 2.0%, 2.5%, 3.0% and the mixed enzyme of pectase,
Cellulase is 1 with the mass ratio of pectase:1, digest 1h at 50 DEG C, put into ultrasonic 15min in ultrasonic cleaner,
5000r/min is centrifuged 20min, takes supernatant, is settled to 50mL.The yield of result lycorine in the range of 1%-2.5% all with
The increase of the consumption of enzyme and raise, therefore enzyme dosage is 2.5% best results.
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 Bulbus Lycoridis Radiatae powder quality 2.0% and the mixed enzyme of pectase, cellulase is 1 with the mass ratio of pectase；1, point
Not at 50 DEG C enzymolysis 20,40,60,80,100min, put into ultrasonic 15min in ultrasonic cleaner, 5000r/min is centrifuged
20min, takes supernatant, is settled to 50mL.Result in enzymolysis time in 20-60min, lycorine yield all increase in time and
Raise, slightly reduce afterwards.Therefore select 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 Bulbus Lycoridis Radiatae powder quality 2.0% and the mixed enzyme of pectase, cellulase is 1 with the mass ratio of pectase；1,
Digest 1h at 50 DEG C, be respectively put into ultrasonic 5 in ultrasonic cleaner, 10,15,20,25min, 5000r/min is centrifuged 20min, takes
Supernatant, is settled to 50mL.Result lycorine yield increases with the growth of sonication treatment time, during 15min in 5-15min
Reach maximum, ultrasonic treatment time should in 15min extraction effect optimal.
With lycorine yield as index, intuitively analyzed and seen Tables 1 and 2 with the results of analysis of variance.
Table 1 orthogonal design and result
| Tested number | A | B | C | D | Lycorine yield/(× 10-3%) |
| 1 | 1 | 1 | 1 | 1 | 144.200 |
| 2 | 1 | 2 | 2 | 2 | 150.100 |
| 3 | 1 | 3 | 3 | 3 | 142.300 |
| 4 | 2 | 1 | 2 | 3 | 146.900 |
| 5 | 2 | 2 | 3 | 1 | 149.600 |
| 6 | 2 | 3 | 1 | 2 | 150.000 |
| 7 | 3 | 1 | 3 | 2 | 142.000 |
| 8 | 3 | 2 | 1 | 3 | 151.500 |
| 9 | 3 | 3 | 2 | 1 | 146.300 |
| k1 | 145.533 | 144.367 | 148.567 | 146.700 | |
| k2 | 148.833 | 150.400 | 147.767 | 147.367 | |
| k3 | 146.600 | 146.200 | 144.633 | 146.900 | |
| R | 3.300 | 6.033 | 3.934 | 0.667 |
Table 2 analysis of variance table
| Soruces of variation | Deviation square | Degree of freedom | Mean square | F value | P value |
| A | 17.016 | 2 | 8.508 | 24.239 | ＜ 0.05 |
| B | 57.402 | 2 | 28.701 | 81.769 | ＜ 0.05 |
| C | 25.929 | 2 | 12.965 | 36.936 | ＜ 0.05 |
| Error | 0.702 | 2 | 0.351 | 1.000 | |
| Summation | 101.049 |
Intuitively analyzed it can be seen that Bulbus Lycoridis Radiatae alkaline extraction optimised process is A by table 12B2C1.According to variance analyses (table
2), the impact notable (P ＜ 0.05) of enzymolysis time, the yield to lycorine for the ultrasonic time；Enzyme dosage is imitated to the extraction of lycorine
Fruit affects notable (P ＜ 0.05).When each factor primary and secondary order of impact lycorine yield is that enzyme dosage ＞ enzymolysis time ＞ is ultrasonic
Between, therefore, the optimal procedure parameters that supercritical ultrasonics technology works in coordination with Enzymatic Extraction are enzymolysis time 1.0h, ultrasonic time 10min, enzyme dosage
2.5%.
Repeatedly extracted for raw material with Lycoris radiata bulb powder in this Optimal technique process, detected during to the 3rd time
Do not go out lycorine, lycorine yield is 0.1812%.
Comparative example is 1.
Ultrasonic assistant extracts lycorine in Bulbus Lycoridis Radiatae：Using 0.5% H2SO4Aqueous solution, solid-liquid ratio 1:10(g:ML), 70
Extraction 2.5h and then ultrasonic treatment time 30min under DEG C water-bath, extract 2 times with this understanding, and lycorine yield is
0.1561%.
Compared with Example 1, lycorine yield is low by 3.42%.
Comparative example is 2.
Lycorine in Enzymatic Extraction Bulbus Lycoridis Radiatae：With solid-liquid ratio 1:10(g:ML) add pH to be in 4.5 water, add 4% fibre
The plain enzyme of dimension digests 2h with pectase mixed enzyme under 50 DEG C of water-baths, extracts 2 times with this understanding, lycorine yield is
0.1752%.
Compared with Example 1, embodiment 1 lycorine yield highest.
Claims (5)
1. a kind of method of monomer lycorine 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, proportional units are 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, obtains final product Bulbus Lycoridis Radiatae alkali extracting solution；
(2) purification
1. solvent extraction：The Bulbus Lycoridis Radiatae alkali extracting solution NaOH that step (1) is extracted adjusts pH to 10, and by volume 1:1 adds extraction
Take agent chloroform, shake up, stand overnight, take off a layer chloroform phase, HCl adjusts pH to 2, sucking filtration, obtain lycorine extraction concentrated solution；
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 lycorine crude product, filters, 50～
60 DEG C are vacuum dried to obtain lycorine monomer.
2. extract the method for monomer lycorine in lycoris plants according to claim 1 it is characterised in that including following
Step：
(1) extract：Weigh treated lycoris plants powder, with solid-liquid ratio 1:10, proportional units are 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, enzymolysis 40-80min at 50 DEG C, then ultrasonic Treatment 15min-20min,
5000r/min is centrifuged 20min, takes supernatant, obtains final product Bulbus Lycoridis Radiatae alkali extracting solution；
(2) purification
1. solvent extraction：The Bulbus Lycoridis Radiatae alkali extracting solution NaOH that step (1) is extracted adjusts pH to 10, and by volume 1:1 adds extraction
Take agent chloroform, shake up, stand overnight, take off a layer chloroform phase, HCl adjusts pH to 2, sucking filtration, obtain lycorine extraction concentrated solution；
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 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 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 lycorine crude product, filters, 50～
60 DEG C are vacuum dried to obtain lycorine monomer.
3. extract the method for monomer lycorine in lycoris plants according to claim 1 and 2 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. extract the method for monomer lycorine in lycoris plants according to claim 1 and 2 it is characterised in that described
Lycoris plants are Lycoris radiata or Caulis et Folium Oryzae Bulbus Lycoridis Radiatae.
5. the method extracting monomer lycorine from lycoris plants according to claim profit requires 1 or 2, its feature exists
In described lycoris plants powder is Lycoris radiata bulb powder.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1936013A (en) * | 2006-09-12 | 2007-03-28 | 贵州芊芊园艺新技术发展公司 | Technological method for extracting lycorine from lycoris plants |
| CN101157947A (en) * | 2007-09-13 | 2008-04-09 | 华中科技大学 | Method for extracting active alkaloid from lycoris herb |
| CN102391266A (en) * | 2011-12-27 | 2012-03-28 | 贵州芊芊园艺新技术发展公司 | Method for extracting and separating pseudolycorine from lycoris plants |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1936013A (en) * | 2006-09-12 | 2007-03-28 | 贵州芊芊园艺新技术发展公司 | Technological method for extracting lycorine from lycoris plants |
| CN101157947A (en) * | 2007-09-13 | 2008-04-09 | 华中科技大学 | Method for extracting active alkaloid from lycoris herb |
| CN102391266A (en) * | 2011-12-27 | 2012-03-28 | 贵州芊芊园艺新技术发展公司 | Method for extracting and separating pseudolycorine from lycoris plants |
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