CN104086424A - Method for extracting and separating chlorogenic acid from honeysuckle flower - Google Patents
Method for extracting and separating chlorogenic acid from honeysuckle flower Download PDFInfo
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- CN104086424A CN104086424A CN201410332285.9A CN201410332285A CN104086424A CN 104086424 A CN104086424 A CN 104086424A CN 201410332285 A CN201410332285 A CN 201410332285A CN 104086424 A CN104086424 A CN 104086424A
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- chlorogenic acid
- extracting
- macroporous resin
- lonicera confusa
- ethanol
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
Abstract
The invention discloses a method for extracting and separating chlorogenic acid from honeysuckle flower. The method comprises the following steps: (1) crushing honeysuckle flowers into medicinal material powder of 10-100 meshes by using a crusher; (2) putting the medicinal material powder obtained in the step (1) into an extraction tank, adding water to perform extraction, and then filtering to obtain an extraction liquid; (3) performing adsorption separation on the extraction liquid obtained in the step (2) by using macro-porous resin, and performing sample loading under the conditions that the sample loading quantity is that the weight ratio of a medicinal material to the macro-porous resin is 1 to (1-8) and the sample loading flow velocity is 0.5-2BV/h; after completing sample loading, firstly flushing by using 0.5-5BV of water at a speed of 0.5-2BV/h, then eluting by using 4-8BV of 10-40% ethanol at a speed of 1-4BV/h, and collecting eluent; and (4), concentrating the eluent to 1/3-1/8 of the original volume, filtering, then performing industrial chromatographic purification, and performing reduced pressure concentration and spray drying on the eluent by using 10-30% ethanol as an eluting agent at a flow velocity of 10-25mL.min<-1> to obtain chlorogenic acid. A process disclosed by the invention is reasonable, feasible, high in chlorogenic acid transfer rate, simple in procedure, single in solvent and convenient in recovery, and has very strong practical values.
Description
Technical field
The present invention relates to extraction and separation technology field, relate in particular to a kind of method of extracting separating chlorogenic acid from Lonicera confusa DC..
Background technology
Chlorogenic acid is from Japanese Honeysuckle, in the medicinal materials such as Lonicera confusa DC., extract and separate a kind of important biologically active substance obtaining, there is pharmacologically active widely, as antibacterial, antiviral, hepatic cholagogic, antitumor, hypotensive, reducing blood-fat, remove free radical and stimulating central nervous system system etc., be with a wide range of applications, as can be used as the effective constituent of the production quality control such as multiple Chinese patent medicine, can replace partial synthesis oxygenant, add in lard and prevent that lard is oxidized, increase the quality guaranteed period, also can be used as the uses such as fodder additives, there is larger market demand, especially highly purified chlorogenic acid extract is expensive.Research obtains high-purity chlorogenic acid and will play an important role to society from plant.
Chlorogenic acid wide material sources, at present mainly contain Japanese Honeysuckle class, Lonicera confusa DC. class, Folium Eucommiae etc. for extracting the medicinal material kind of separating chlorogenic acid, the Chinese medicine that wherein the Lonicera confusa DC. class medicinal material such as largeflower-like honeysuckle flower, lonicera hypoglauca miq, Lonicera confusa records for Chinese Pharmacopoeia, there is higher chlorogenic acid content, and the report quantity of openly extracting separating chlorogenic acid both at home and abroad from Lonicera confusa DC. is relatively less, selects from Lonicera confusa DC., to extract separating chlorogenic acid and there is larger resources advantage.
In chlorogenic acid structure, have active group, its character is unstable, and extracting can not be in the environment of high temperature, high light, facile hydrolysis while separation.At present report that the main method of extracting separating chlorogenic acid from natural drug has solvent-extraction process, physical field assisted Extraction to follow the example of (ultrasonic field, microwave field etc.), alcohol deposition method, ethyl acetate extraction process, Amberlyst process etc.In said extracted separation method, there are some problems, follow the example of and be not suitable for scale operation as physical field assisted Extraction, the rate of transform of alcohol deposition method, ethyl acetate extraction process is low, process is dangerous, solvent toxicity is large, and the rate of transform of the Amberlyst process of having reported is low, process is complicated, solvent for use is not suitable for reclaiming.Therefore the chlorogenic acid rate of transform is high, process is simple to study one, and solvent toxicity extraction separating technology route little and that can conveniently be reclaimed has important economic implications.
Summary of the invention
The invention provides a kind of method of extracting separating chlorogenic acid from Lonicera confusa DC..
The present invention adopts following technical scheme:
The concrete steps of the method for extracting separating chlorogenic acid from Lonicera confusa DC. of the present invention are as follows:
(1) use pulverizer to pulverize Lonicera confusa DC., be ground into 10-100 object medicinal powder;
(2) medicinal powder of step (1) is put into extractor extracting in water, solid-liquid ratio is 1:10-30, and extraction temperature is 40-90 DEG C, extracts 1-2 time, and each 0.5-2h, then filters and obtain extracting solution;
(3) extracting solution step (2) being obtained carries out fractionation by adsorption by macroporous resin, macroporous resin fills post with wet method, its blade diameter length ratio is 1:3-10, applied sample amount is that the weight ratio of medicinal material and macroporous resin is 1:1-8, loading flow velocity is 0.5-2BV/h, after completion of the sample, first rinses with the speed of 0.5-2 BV/h with the water of 0.5-5 BV, then use the ethanol of 4-8 BV 10%-40% with the speed wash-out of 1-4BV/h, collect elutriant;
(4) elutriant of step (3) gained is concentrated into original volume 1/3～1/8, after filtering, by industrial chromatography purifying, using 10%-30% ethanol as eluent, flow velocity is 10-25mLmin
-1, elutriant concentrating under reduced pressure, spraying are dried, and obtain chlorogenic acid product.
In step (1), preferably Lonicera confusa DC. is ground into 60 object drug powders.
In step (2), the medicinal powder of step (1) is put into extractor extracting in water, solid-liquid ratio is 1:20, and extracting temperature is 60 DEG C, extracts 1 time, and extraction time is 2h, then filters and obtains extracting solution.
In step (3), macroporous resin is that D101 type, AB-8 type, HPD100 type, HPD750 type or the preferred macroporous resin of ADS-7 type are ADS-7 type.
In step (3), macroporous resin fills post with wet method, and its blade diameter length ratio is preferably 1:5-8.
In step (3), the weight ratio of preferably extracting medicinal material and macroporous resin is 1:5, loading flow velocity is 1 BV/h, after completion of the sample, first rinse with the speed of 1 BV/h with the distilled water of 1 BV, then use the ethanol of 6 BV with the speed wash-out of 2 BV/h, collect elutriant, the mass concentration of described ethanol is 20%.
In step (3), macroporous resin carries out pre-treatment before using, step is as follows: by extremely anhydrous drippage of macroporous resin decompress filter, for subsequent use, test before by macroporous resin with more than 95% alcohol immersion 24h, remove macroporous resin fragment and foreign material, wet method upper prop, after being first washed till effluent liquid and mixing with water with 95% ethanol till aobvious muddiness, then be washed till effluent liquid without alcohol taste with distilled water; Then use again 4% sodium hydroxide solution with 2BV volume with 2BVh
-1speed is rinsed, and then soaks 2～4h, and it is neutral being washed till effluent liquid with distilled water; Use again 4% hydrochloric acid soln with 2BV volume with 2BVh
-1speed is rinsed, and then soaks 2～4h, and it is neutral being washed till effluent liquid with distilled water.
In step (4), chromatograph packing material is the one in CT-25-1, CT-25-2, PIPO-02, and preferably chromatograph packing material is PIPO-02.
Positively effect of the present invention is as follows:
The present invention adopts the method for extracting separating chlorogenic acid taking water extraction-macroporous resin adsorption separation-industrial chromatography purifying as the complete set technology of core from Lonicera confusa DC. first, set up the operational path of an extraction from Lonicera confusa DC., separation, purification of high-purity chlorogenic acid, this technique is reasonable, feasible, the rate of transform of chlorogenic acid is high, process is simple, solvent is convenient to be reclaimed, and has very strong practical value.
Embodiment
The following examples are to describe in further detail of the present invention.
Embodiment 1
The concrete steps of the method for extracting separating chlorogenic acid from Lonicera confusa DC. of the present invention are as follows:
(1) use pulverizer to pulverize Lonicera confusa DC., be ground into 10 object medicinal powders;
(2) medicinal powder of step (1) is put into extractor extracting in water, solid-liquid ratio is 1:10, and extracting temperature is 40 DEG C, extracts 2 times, and each 2h, then filters and obtain extracting solution;
(3) extracting solution step (2) being obtained carries out fractionation by adsorption by macroporous resin, applied sample amount is that the weight ratio of medicinal material and macroporous resin is 1:1, loading flow velocity is 0.5 BV/h, after completion of the sample, first rinse with the speed of 0.5 BV/h with the water of 0.5 BV, then use the ethanol of 4 BV10% with the speed wash-out of 1 BV/h, collect elutriant;
(4) elutriant of step (3) gained is concentrated into original volume 1/3, upper industrial chromatography after filtering, chromatograph packing material is CT-25-1, using 10% ethanol as eluent, flow velocity is 10mLmin
-1, elutriant concentrating under reduced pressure, spraying are dried, and obtain chlorogenic acid product.
In step (3), macroporous resin is D101 type.
In step (3), macroporous resin carries out pre-treatment before using, step is as follows: by extremely anhydrous drippage of macroporous resin decompress filter, for subsequent use, test before by macroporous resin with more than 95% alcohol immersion 24h, remove macroporous resin fragment and foreign material, wet method upper prop, after being first washed till effluent liquid and mixing with water with 95% ethanol till aobvious muddiness, then be washed till effluent liquid without alcohol taste with distilled water; Then use again 4% sodium hydroxide solution with 2BV volume with 2BVh
-1speed is rinsed, and then soaks 2～4h, and it is neutral being washed till effluent liquid with distilled water; Use again 4% hydrochloric acid soln with 2BV volume with 2BVh
-1speed is rinsed, and then soaks 2～4h, and it is neutral being washed till effluent liquid with distilled water.
In step (3), macroporous resin fills post with wet method, and its blade diameter length ratio is 1:3.
Embodiment 2
The concrete steps of the method for extracting separating chlorogenic acid from Lonicera confusa DC. of the present invention are as follows:
(1) use pulverizer to pulverize Lonicera confusa DC., be ground into 100 object medicinal powders;
(2) medicinal powder of step (1) is put into extractor extracting in water, solid-liquid ratio is 1:30, and extracting temperature is 90 DEG C, extracts 1 time, and each 0.5h, then filters and obtain extracting solution;
(3) extracting solution step (2) being obtained carries out fractionation by adsorption by macroporous resin, applied sample amount is that the weight ratio of medicinal material and macroporous resin is 1:8, loading flow velocity is 2 BV/h, after completion of the sample, first rinse with the speed of 2 BV/h with the water of 5 BV, then use the ethanol of 8BV 40% with the speed wash-out of 4 BV/h, collect elutriant;
(4) elutriant of step (3) gained is concentrated into original volume 1/8, upper industrial chromatography after filtering, chromatograph packing material is CT-25-2, using 30% ethanol as eluent, flow velocity is 25mLmin
-1, elutriant concentrating under reduced pressure, spraying are dried, and obtain chlorogenic acid product.
In step (3), macroporous resin is HPD750 type.
In step (3), macroporous resin carries out pre-treatment before using, step is as follows: by extremely anhydrous drippage of macroporous resin decompress filter, for subsequent use, test before by macroporous resin with more than 95% alcohol immersion 24h, remove macroporous resin fragment and foreign material, wet method upper prop, after being first washed till effluent liquid and mixing with water with 95% ethanol till aobvious muddiness, then be washed till effluent liquid without alcohol taste with distilled water; Then use again 4% sodium hydroxide solution with 2BV volume with 2BVh
-1speed is rinsed, and then soaks 2～4h, and it is neutral being washed till effluent liquid with distilled water; Use again 4% hydrochloric acid soln with 2BV volume with 2BVh
-1speed is rinsed, and then soaks 2～4h, and it is neutral being washed till effluent liquid with distilled water.
In step (3), macroporous resin fills post with wet method, and its blade diameter length ratio is 1:10.
Embodiment 3
The concrete steps of the method for extracting separating chlorogenic acid from Lonicera confusa DC. of the present invention are as follows:
(1) use pulverizer to pulverize Lonicera confusa DC., be ground into 60 object medicinal powders;
(2) medicinal powder of step (1) is put into extractor extracting in water, solid-liquid ratio is 1:20, and extracting temperature is 60 DEG C, extracts 1 time, extracts 2h, then filters and obtains extracting solution;
(3) extracting solution step (2) being obtained carries out fractionation by adsorption by macroporous resin, applied sample amount is that the weight ratio of medicinal material and macroporous resin is 1:5, loading flow velocity is 1 BV/h, after completion of the sample, first rinse with the speed of 1 BV/h with the water of 1 BV, then use the ethanol of 6 BV 20% with the speed wash-out of 2 BV/h, collect elutriant;
(4) elutriant of step (3) gained is concentrated into original volume 1/5, upper industrial chromatography after filtering, chromatograph packing material is PIPO-02, using 20% ethanol as eluent, flow velocity is 16.46mLmin
-1, elutriant concentrating under reduced pressure, spraying are dried, and obtain chlorogenic acid product.
In step (3), macroporous resin is ADS-7 type.
In step (3), macroporous resin carries out pre-treatment before using, step is as follows: by extremely anhydrous drippage of macroporous resin decompress filter, for subsequent use, test before by macroporous resin with more than 95% alcohol immersion 24h, remove macroporous resin fragment and foreign material, wet method upper prop, after being first washed till effluent liquid and mixing with water with 95% ethanol till aobvious muddiness, then be washed till effluent liquid without alcohol taste with distilled water; Then use again 4% sodium hydroxide solution with 2BV volume with 2BVh
-1speed is rinsed, and then soaks 2～4h, and it is neutral being washed till effluent liquid with distilled water; Use again 4% hydrochloric acid soln with 2BV volume with 2BVh
-1speed is rinsed, and then soaks 2～4h, and it is neutral being washed till effluent liquid with distilled water.
In step (3), macroporous resin fills post with wet method, and its blade diameter length ratio is 1:5.
Extract the calculation specifications of test
Solution Content of Chlorogenic Acid total amount (mg)=C × V
1
Medicinal extract content (%)=(C × V
2/ W
1) × 100%
The rate of transform (%)=C × V
1/ (W
0× 4.41%) × 100%
C: according to regression equation calculation gained solution Content of Chlorogenic Acid concentration (mgml
-1)
V
1: extracting solution cumulative volume (ml)
W
0: Lonicera confusa DC. medicinal material weight (mg)
V
2: dissolve medicinal extract liquor capacity (ml)
W
1: medicinal extract sampling heavy (mg)
Extraction efficiency refers to extract chlorogenic acid amount in the unit time, is directly proportional to extracting solution Content of Chlorogenic Acid amount, is inversely proportional to extraction time.
In extraction test, the rate of transform refers to the rate of transform of extraction process.
Medicinal extract content and the rate of transform of the leaching process to embodiment 1-3 are calculated, and result is as shown in table 1.
Table 1
The present invention, under the condition of low production cost, transfers to as much as possible medicinal material Content of Chlorogenic Acid and extracts in solvent, and other impurity components in medicinal material are retained in the dregs of a decoction as much as possible.As can be seen from Table 1, method chlorogenic acid mean transferred rate of the present invention is 82.98 ± 0.52%.
The calculating of macroporous resin adsorption separation test and explanation
Solution Content of Chlorogenic Acid total amount (mg)=C × V
1
Adsorptive capacity (%)=applied sample amount-discharge
Adsorption rate (%)=(applied sample amount-discharge)/(applied sample amount) × 100%
Water elution rate (%)=water elution amount/adsorptive capacity × 100%
Eluting rate (%)=elution amount/adsorptive capacity × 100%
Chlorogenic acid purity (%)=(C × V
2/ W
1) × 100%
The rate of transform (%)=elution amount/applied sample amount × 100%
C: according to regression equation calculation gained solution Content of Chlorogenic Acid concentration (mgml
-1)
V
1: overall solution volume (ml)
V
2: the volume (ml) that dissolves elutriant medicinal extract
W
1: elutriant medicinal extract sampling amount (mg)
Applied sample amount is the extracting solution Content of Chlorogenic Acid total amount (mg) that flows through macroporous resin bed.
When outflow liquid measure is loading, effluent liquid Content of Chlorogenic Acid total amount (mg).
Water elution amount when washing with water, the receiving liquid Content of Chlorogenic Acid total amount (mg) of gained.
Elution amount is with after the eluent drip washing that contains ethanol, the receiving liquid Content of Chlorogenic Acid total amount (mg) of gained.
In macroporous resin adsorption separation test, purity refers to the medicinal extract Content of Chlorogenic Acid purity that elutriant is dried to
In macroporous resin adsorption separation test, the rate of transform refers to the rate of transform of macroporous resin adsorption separating technology.
Purity and the rate of transform of the macroporous resin sepn process to embodiment 1-3 are calculated, and result is as shown in table 2.
Table 2
The present invention, under the condition of low production cost, transfers in eluting solvent extracting solution Content of Chlorogenic Acid as much as possible, and other impurity component content in elutriant are reduced as far as possible.The mean transferred rate of this process chlorogenic acid is 95.12 ± 0.73% as can be seen from Table 2.
The calculation specifications of industrial chromatography purification experiment
Solution Content of Chlorogenic Acid total amount (mg)=C × V
1
Rate of transform %=elution amount/sample size × 100%
Chlorogenic acid purity (%)=(C × V
2/ W
1) × 100%
C: according to regression equation calculation gained solution Content of Chlorogenic Acid concentration (mgml
-1)
V
1: overall solution volume (ml)
V
2: the cumulative volume (ml) that dissolves dry powder solution
W
1: get chlorogenic acid extract dry powder weight (mg)
Sample size is the elutriant Content of Chlorogenic Acid total amount of gained under optimum macroporous resin adsorption separating technology condition.
Elution amount is the receiving liquid Content of Chlorogenic Acid total amount of gained after industrial chromatography purifying.
Preparation efficiency is the amount that elutes chlorogenic acid within the unit time, is directly proportional to elution amount, is inversely proportional to industrial chromatography elution time.
In industrial chromatography purification experiment, purity refers to the dry powder Content of Chlorogenic Acid purity of the spray-dried one-tenth of elutriant.
In industrial chromatography purification experiment, the rate of transform refers to the rate of transform of industrial chromatography purifying process.
The rate of transform of the industrial chromatography purge process to embodiment 1-3 is calculated, and result is as shown in table 3.
Table 3
Although illustrated and described embodiments of the invention, for the ordinary skill in the art, be appreciated that without departing from the principles and spirit of the present invention and can carry out multiple variation, amendment, replacement and modification to these embodiment, scope of the present invention is limited by claims and equivalent thereof.
Claims (10)
1. a method of extracting separating chlorogenic acid from Lonicera confusa DC., is characterized in that: the concrete steps of described method are as follows:
(1) use pulverizer to pulverize Lonicera confusa DC., be ground into 10-100 object medicinal powder;
(2) medicinal powder of step (1) is put into extractor extracting in water, solid-liquid ratio is 1:10-30, and extraction temperature is 40-90 DEG C, extracts 1-2 time, and each 0.5-2h, then filters and obtain extracting solution;
(3) extracting solution step (2) being obtained carries out fractionation by adsorption by macroporous resin, macroporous resin fills post with wet method, its blade diameter length ratio is 1:3-10, applied sample amount is that the weight ratio of medicinal material and macroporous resin is 1:1-8, loading flow velocity is 0.5-2 BV/h, after completion of the sample, first rinses with the speed of 0.5-2 BV/h with the water of 0.5-5 BV, then use the ethanol of 4-8 BV 10%-40% with the speed wash-out of 1-4 BV/h, collect elutriant;
(4) elutriant of step (3) gained is concentrated into original volume 1/3～1/8, after filtering, by industrial chromatography purifying, using 10%-30% ethanol as eluent, flow velocity is 10-25mLmin
-1, elutriant concentrating under reduced pressure, spraying are dried, and obtain chlorogenic acid product.
2. the method for extracting separating chlorogenic acid from Lonicera confusa DC. as claimed in claim 1, is characterized in that: in step (1), Lonicera confusa DC. is ground into 60 object drug powders.
3. the method for extracting separating chlorogenic acid from Lonicera confusa DC. as claimed in claim 1, it is characterized in that: in step (2), the medicinal powder of step (1) is put into extractor extracting in water, solid-liquid ratio is 1:20, extracting temperature is 60 DEG C, extract 1 time, extraction time is 2h, then filters and obtains extracting solution.
4. the method for extracting separating chlorogenic acid from Lonicera confusa DC. as claimed in claim 1, is characterized in that: in step (3), macroporous resin is D101 type, AB-8 type, HPD100 type, HPD750 type or ADS-7 type.
5. the method for extracting separating chlorogenic acid from Lonicera confusa DC. as claimed in claim 1, is characterized in that: in step (3), macroporous resin is ADS-7 type.
6. the method for extracting separating chlorogenic acid from Lonicera confusa DC. as claimed in claim 1, is characterized in that: in step (3), macroporous resin fills post with wet method, and its blade diameter length ratio is 1:5-8.
7. the method for extracting separating chlorogenic acid from Lonicera confusa DC. as claimed in claim 1, it is characterized in that: in step (3), the weight ratio of extracting medicinal material and macroporous resin is 1:5, loading flow velocity is 1 BV/h, after completion of the sample, first rinse with the speed of 1 BV/h with the distilled water of 1 BV, then use the ethanol of 6 BV with the speed wash-out of 2 BV/h, collect elutriant, the mass concentration of described ethanol is 20%.
8. the method for extracting separating chlorogenic acid from Lonicera confusa DC. as claimed in claim 1, is characterized in that: in step (4), chromatograph packing material is the one in CT-25-1, CT-25-2, PIPO-02.
9. the method for extracting separating chlorogenic acid from Lonicera confusa DC. as claimed in claim 1, is characterized in that: in step (4), chromatograph packing material is PIPO-02.
10. the method for extracting separating chlorogenic acid from Lonicera confusa DC. as claimed in claim 1, is characterized in that: in step (4), eluent is that concentration is 10% ethanol, and flow velocity is 15mLmin
-1.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107793314A (en) * | 2017-10-20 | 2018-03-13 | 中山大学 | A kind of method that 8 kinds of monomers are prepared from Honeysuckle flower |
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|---|---|---|---|---|
| JPH04145048A (en) * | 1990-10-04 | 1992-05-19 | T Hasegawa Co Ltd | Production of purified chlorogenic acid |
| CN1616403A (en) * | 2004-09-21 | 2005-05-18 | 济南永曜医药科技有限公司 | Process for preparing chlorogenic acid from honeysuckle |
| CN1687008A (en) * | 2005-03-22 | 2005-10-26 | 中国药科大学 | Method for extracting compound of phenolic acid from leaves of woodbind |
| CN102973635A (en) * | 2012-11-22 | 2013-03-20 | 贵州大学 | Wild honeysuckle flower extracting method |
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2014
- 2014-07-11 CN CN201410332285.9A patent/CN104086424B/en active Active
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| JPH04145048A (en) * | 1990-10-04 | 1992-05-19 | T Hasegawa Co Ltd | Production of purified chlorogenic acid |
| CN1616403A (en) * | 2004-09-21 | 2005-05-18 | 济南永曜医药科技有限公司 | Process for preparing chlorogenic acid from honeysuckle |
| CN1687008A (en) * | 2005-03-22 | 2005-10-26 | 中国药科大学 | Method for extracting compound of phenolic acid from leaves of woodbind |
| CN102973635A (en) * | 2012-11-22 | 2013-03-20 | 贵州大学 | Wild honeysuckle flower extracting method |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107793314A (en) * | 2017-10-20 | 2018-03-13 | 中山大学 | A kind of method that 8 kinds of monomers are prepared from Honeysuckle flower |
| CN107793314B (en) * | 2017-10-20 | 2021-01-29 | 中山大学 | Method for preparing 8 monomers from lonicera confusa |
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| CN104086424B (en) | 2016-01-27 |
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