CN106117284B - A kind of method of six kinds of iridoid glycoside constituents in while Extraction and enrichment honeysuckle - Google Patents
A kind of method of six kinds of iridoid glycoside constituents in while Extraction and enrichment honeysuckle Download PDFInfo
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- CN106117284B CN106117284B CN201610544064.7A CN201610544064A CN106117284B CN 106117284 B CN106117284 B CN 106117284B CN 201610544064 A CN201610544064 A CN 201610544064A CN 106117284 B CN106117284 B CN 106117284B
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- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
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- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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Abstract
The invention discloses a kind of methods of six kinds of iridoid glycoside constituents in Extraction and enrichment honeysuckle simultaneously, specific step is as follows: (1) drying and crushing being taken to cross the Honeysuckle Flower of 20-40 mesh, use ethyl alcohol as Extraction solvent, ultrasonic extraction is carried out to Honeysuckle Flower, ethanol extract is filtered after ultrasound, it is spare to obtain extracting solution to no alcohol taste for concentrated by rotary evaporation；(2) the extracting solution loading macroporous absorbent resin for obtaining step (1) carries out six kinds of iridoid glycoside constituents enrichments, and adsorption process applied sample amount is 0.5-0.7g Honeysuckle Flower/mL resin, volume flow 1-3BV/h；The ethanol eluate that gradient elution obtains six kinds of iridoid glycoside constituents is carried out using ethanol solution, removal of impurities is first washed with water before elution；(3) ethanol eluate that step (2) obtains is removed into ethyl alcohol and obtains iridoid glycoside.This method is easy to operate, example enrichment effect is good, and as a result reproducibility is high, and stability is good.
Description
Technical field
The invention belongs to field of natural organic chemistry, and in particular to six iridoids in a kind of while Extraction and enrichment honeysuckle
The method of methods of glycosides.
Background technique
Honeysuckle is the dry flower of Caprifoliaceae woodbine honeysuckle Lonicera japonica Thunb. or just opens
Flower.Its is sweet in flavor, cold in nature, and return lung, the heart, stomach meridian have the function of clearing heat and detoxicating, dispelling wind and heat from the body.Honeysuckle and related Chinese patent drug
It is clearing heat and detoxicating, in terms of it is significant in efficacy, be widely applied clinically.
The chemical component of honeysuckle include volatile oil, iridoid glycosides compound, triterpene and triterpene saponin componds,
Flavone compound, organic acid compound etc..Wherein, iridoid glycosides compound is the important chemistry of one kind in honeysuckle
Ingredient.Recent study discovery, iridoid glycoside constituents have antiviral, antibacterial, anti-oxidant, Hepatoprotective cholagogue, antitumor, anti-
Inflammation enhances the various actives such as immune.
It is reported that the iridoid glycosides compound up to 36 identified by separation at present in honeysuckle at present
It is a, wherein logaric acid, morroniside, loganin, chiratin, disconnected oxidation loganin and Secologanin dimethyl-acetal 6
Kind iridoid glycosides compound has the pharmacological actions such as preferable antiviral, anti-inflammatory, Hepatoprotective cholagogue, inhibition tumour more because of it
Attention by researcher.Therefore, how effectively, convenient and safe this 6 kinds of iridoid glycoside constituents of Extraction and enrichment at
For the key for more preferably utilizing honeysuckle problem.To iridoid glycosides Extraction and enrichment method multiplicity in existing report, vapor steams
It evaporates the methods of method, supercritical fluid extraction, organic solvent extraction to have been reported that, although however supercritical fluid extraction tool
There are high income, volatile oil to be not easily decomposed oxidation, the advantages that green non-pollution, but equipment is disposably put into greatly, and it is at high cost, in industry
The application for changing extraction Chinese medicine and plant volatile oil is not universal.It is more then to there are the impurity such as pigment in organic solvent extraction, and has
Dissolvent residual.And the main problem that iridoid glycosides compound is extracted in steam distillation industrialization is iridoid glycosides tool
Hydrophily, is separated from water that effect is poor, and yield is very low.And due to every kind of iridoid glycosides compound all have respectively it is peculiar
Group, cause its physicochemical property to have differences, thus cause enrichment extract specific several iridoid glucosides class compound when more
Add difficulty.Therefore, develop the fast and efficiently Extraction and enrichment method of this 6 kinds of iridoid glycoside constituents in suitable honeysuckle urgently
It is to be solved.
Summary of the invention
In view of the above shortcomings of the prior art, the present invention provides iridoid glycosides in a kind of while Extraction and enrichment honeysuckle
The method of ingredient, this method is easy to operate, example enrichment effect is good, and as a result reproducibility is high, and stability is good.
To achieve the above object, the present invention adopts the following technical scheme:
A kind of method of six kinds of iridoid glycoside constituents in while Extraction and enrichment honeysuckle, wherein the six of Extraction and enrichment kind
Iridoid glycoside constituents are logaric acid, morroniside, loganin, chiratin, disconnected oxidation loganin and Secologanin two
Methyl acetal, the specific steps are as follows:
(1) it takes drying and crushing to cross the Honeysuckle Flower of 20-40 mesh, uses ethyl alcohol as Extraction solvent, to honeysuckle powder
End carries out ultrasonic extraction, filters after ultrasound to ethanol extract, it is spare to obtain extracting solution to no alcohol taste for concentrated by rotary evaporation；
(2) the extracting solution loading macroporous absorbent resin for obtaining step (1) carries out six kinds of iridoid glycoside constituents enrichments,
Adsorption process applied sample amount is 0.5-0.7g Honeysuckle Flower/mL resin, volume flow 1-3BV/h；It is carried out using ethanol solution
Gradient elution obtains the ethanol eluate of six kinds of iridoid glycoside constituents, and removal of impurities is first washed with water before elution.
(3) ethanol eluate that step (2) obtains is removed into ethyl alcohol and obtains iridoid glycoside.
Preferably, it is 20 mesh that grit number is crossed in the step (1)；Ethyl alcohol used is 50% ethyl alcohol, the Honeysuckle Flower
It is 1g:10ml with ethyl alcohol mass volume ratio；
Preferably, ultrasonic extraction actual conditions in the step (1) are as follows: ultrasonic extraction 2h, temperature is 25 DEG C when ultrasonic；
Preferably, macroporous absorbent resin is NKA-2 resin or HPD-826 resin in the step (2)；Further preferably
, the macroporous absorbent resin is HPD-826 resin；
Preferably, adsorption process applied sample amount is 0.61g Honeysuckle Flower/mL resin in the step (2)；
Preferably, volume flow is 2BV/h in the step (2)；
Preferably, distilling water consumption in the step (2) in washed with impurities is 3BV；
Preferably, gradient elution method in the step (3) are as follows: 10% ethanol elution 7BV, 30% ethanol elution 7BV,
50% ethanol elution 2BV；
Preferably, ethyl alcohol used is medicinal alcohol in the above method.
The invention also discloses application of the above method in the enrichment of Chinese medicine iridoid glycosides constituents extraction.
The present invention overcomes the limitations of the defect of the prior art and condition, and the present invention has and has as follows compared with prior art
Beneficial effect:
(1) present invention uses macroreticular resin absorbing method, is enriched with to using the gold and silver garland extracting solution of ultrasonic wave extraction,
It is eluted with medicinal alcohol, dosage is less, can directly obtain 6 kinds of iridoid glycoside constituents ethanol solutions of high concentration, steams
It goes after solvent up to iridoid glycosides；In solving industrial mass production while organic residue problem, also reduce organic
The usage amount of solvent.
(2) method of the invention can be adapted for the Extraction and enrichment of the iridoid glycoside constituents of different Chinese medicines, can be significant
The yield of iridoid glycoside constituents is improved, as a result reproducibility is high, and stability is good.Solvent for use is medicinal alcohol, safe and non-toxic,
It is inexpensive.
(3) method of the invention is particularly suitable for the higher substance of hydrophilic radical ratio such as iridoid glycoside constituents and its
The extraction of analog.Since the higher substance of hydrophilic radical ratio is difficult to be separated with water, cause to extract difficulty, meanwhile, it is right
It is extracted simultaneously in many kinds of substance and then further increases extraction difficulty, the present invention chooses by using macroporous resin adsorption and is suitble to model
Macroreticular resin and process of enriching parameter, then realize the Extraction and enrichment to such difficult extraction of substance.Extraction and enrichment side of the present invention
Method is easy to operate, example enrichment effect is good, and as a result reproducibility is high, and stability is good.
Specific embodiment
The present invention is further illustrated in conjunction with the embodiments, it should which explanation, following the description is merely to explain this
Invention, is not defined its content.
Embodiment 1: six kinds of iridoid glycosides constituents extraction process of enriching in honeysuckle
1. drying and crushing is taken to cross the Honeysuckle Flower 300g of 20 meshes, 50% ethyl alcohol is as Extraction solvent, solid-liquid ratio 1g:
10ml carries out ultrasonic extraction, and ultrasonic 2h, 25 DEG C of ultrasonic temperature, extracting solution filters, and concentrated by rotary evaporation is spare to no alcohol taste.
2.HPD-826 type macroporous absorbent resin is the absorption of 2BV/h loading, every mL hygrometric state resin treatment with volume flow
0.61g Honeysuckle Flower, after absorption completely, then 3BV distilled water washed with impurities carry out gradient elution: 10% ethyl alcohol of 7BV,
30% ethyl alcohol of 7BV, 50% ethanol gradient elution of 2BV, elution volume flow are 2BV/h, and obtained ethanol eluate removes second
Alcohol obtains iridoid glycoside.
Experiment proves that each iridoid glycoside content is greatly improved, together after HPD-826 macroporous resin enrichment
When retention rate it is most of 64% or more, the retention rate of chiratin and Secologanin dimethyl-acetal is even up to
100%.Show this method with to 6 kinds of alkene ether terpene glycosides have excellent concentration effect.
Embodiment 2: six kinds of iridoid glycosides constituents extraction process of enriching in honeysuckle
1. drying and crushing is taken to cross the Honeysuckle Flower 300g of 20 meshes, 50% ethyl alcohol is as Extraction solvent, solid-liquid ratio 1g:
10ml carries out ultrasonic extraction, and ultrasonic 2h, 25 DEG C of ultrasonic temperature, extracting solution filters, and concentrated by rotary evaporation is spare to no alcohol taste.
2.HPD-826 type macroporous absorbent resin is the absorption of 3BV/h loading, every mL hygrometric state resin treatment with volume flow
0.7g Honeysuckle Flower, after absorption completely, then 3BV distilled water washed with impurities carry out gradient elution: 10% ethyl alcohol of 7BV, 7BV
30% ethyl alcohol, 50% ethanol gradient elution of 2BV, elution volume flow are 2BV/h, and obtained ethanol eluate removes ethyl alcohol and obtains
Iridoid glycoside.
Embodiment 3: six kinds of iridoid glycosides constituents extraction process of enriching in honeysuckle
1. drying and crushing is taken to cross the Honeysuckle Flower 300g of 20 meshes, 50% ethyl alcohol is as Extraction solvent, solid-liquid ratio 1g:
10ml carries out ultrasonic extraction, and ultrasonic 2h, 25 DEG C of ultrasonic temperature, extracting solution filters, and concentrated by rotary evaporation is spare to no alcohol taste.
2.NKA-2 type macroporous absorbent resin is the absorption of 1BV/h loading, every mL hygrometric state resin treatment 0.5g with volume flow
Honeysuckle Flower, after absorption completely, then 3BV distilled water washed with impurities carry out gradient elution: 10% ethyl alcohol of 7BV, 7BV
30% ethyl alcohol, 50% ethanol gradient elution of 2BV, elution volume flow are 2BV/h, and obtained ethanol eluate removes ethyl alcohol and obtains
Iridoid glycoside.
Comparative example 1
HPD-826 macroreticular resin is replaced with into D4020, HPD-500, DM130, D101, HPD-400 and HPD-100, remaining
With embodiment 1.
1 six kinds of macroreticular resins of embodiment 1 and comparative example are calculated to the adsorbance of six kinds of iridoid glycoside constituents, are as a result seen
Table 1.
1 macroporous resin adsorption ability (mg/mL) of table
As it can be seen from table 1 the macroporous absorbent resin of various models for the iridoid glycoside in Flos Lonicerae extractive solution at
Dividing has different degrees of absorption.But HPD-826 adsorption effect is much better than other absorption resins.
Comparative example 2
Loading volume flow in embodiment 1 is adjusted to 1BV/h, 5BV/h, 10BV/h and 20BV/h, remaining is the same as implementation
Example 1.
After completion of the sample, absorption of the macroreticular resin to six kinds of iridoid glycoside constituents in measurement embodiment 1, comparative example 2
Rate the results are shown in Table 2.
2 loading flow velocity of table investigates result
The result shows that macroreticular resin is higher to the adsorption rate of six kinds of iridoid glycosides, with flow velocity when loading flow velocity is lower
Increase, macroreticular resin reduces the adsorption rate of six kinds of iridoid glycosides.But loading flow velocity is also unsuitable relatively low, and flow velocity is too low to drop
Low production efficiency increases production cost.Therefore, adsorption effect and production efficiency are comprehensively considered, with loading used by embodiment 1
Flow velocity 2BV/h is advisable.
Comparative example 3
Gradient elution (scheme 1) in embodiment 1 is revised as single mode to elute, uses 10% ethyl alcohol list of 7BV respectively
One mode elutes (scheme 2), and the single mode of 30% ethyl alcohol of 7BV elutes (scheme 3), the single mode of 50% ethyl alcohol of 2BV (scheme 4)
Elution calculates embodiment 1 and 3 each type of elution of comparative example, six kinds of each desorption efficiencies of iridoid glycoside constituents.
3 type of elution desorption efficiency of table investigates result
It is not difficult to find out by 3 result of table, although the single type of elution of comparative example has a certain or several iridoid glycosides
Ingredient desorption efficiency is higher than the gradient elution in embodiment 1, but in general, the type of elution in embodiment 1 is much better than comparative example
Scheme 2-4.
Above-mentioned, although specific embodiments of the present invention have been described with comparative example in conjunction with the embodiments, not to this
The limitation of invention protection scope, those skilled in the art should understand that, based on the technical solutions of the present invention, this field
Technical staff does not need to make the creative labor the various modifications or changes that can be made still within protection scope of the present invention.
Claims (7)
1. a kind of method of six kinds of iridoid glycoside constituents in Extraction and enrichment honeysuckle simultaneously, which is characterized in that described six kinds
Iridoid glycoside constituents are logaric acid, morroniside, loganin, chiratin, disconnected oxidation loganin and Secologanin two
Methyl acetal, the specific steps are as follows:
(1) Honeysuckle Flower for taking drying and crushing to be sieved uses ethyl alcohol as Extraction solvent, carries out ultrasound to Honeysuckle Flower and mention
It takes, ethanol extract is filtered after ultrasound, it is spare to obtain extracting solution to no alcohol taste for concentrated by rotary evaporation；
(2) the extracting solution loading macroporous absorbent resin for obtaining step (1) carries out six kinds of iridoid glycoside constituents enrichments, absorption
Process applied sample amount is 0.5-0.7g Honeysuckle Flower/mL resin, volume flow 2BV/h；Gradient is carried out using ethanol solution to wash
The ethanol eluate of de- six kinds of iridoid glycoside constituents, is first washed with water removal of impurities before elution；
(3) ethanol eluate that step (2) obtains is removed into ethyl alcohol and obtains iridoid glycoside；
Macroporous absorbent resin is HPD-826 resin in the step (2)；
Gradient elution method in the step (2) are as follows: 10% ethanol elution 7BV, 30% ethanol elution 7BV, 50% ethanol elution
2BV。
2. the method as described in claim 1, which is characterized in that crossing grit number in the step (1) is 20-40 mesh；Second used
Alcohol is 50% ethyl alcohol, and the Honeysuckle Flower and ethyl alcohol mass volume ratio are 1g:10ml.
3. method according to claim 2, which is characterized in that the grit number of crossing is 20 mesh.
4. the method as described in claim 1, which is characterized in that ultrasonic extraction actual conditions in the step (1) are as follows: ultrasound mentions
2h is taken, temperature is 25 DEG C when ultrasonic.
5. the method as described in claim 1, which is characterized in that adsorption process applied sample amount is 0.61g gold and silver in the step (2)
Pollen end/mL resin.
6. the method as described in claim 1, which is characterized in that distilling water consumption in the step (2) in washed with impurities is
3BV。
7. the method as described in claim 1, which is characterized in that ethyl alcohol used is medicinal alcohol.
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| CN116549476B (en) * | 2023-07-10 | 2023-09-19 | 暨南大学附属第一医院（广州华侨医院） | Compound, composition and application thereof in preparation of drugs with tumor angiogenesis inhibiting effect |
| CN118576633B (en) * | 2024-08-02 | 2024-10-29 | 山东中医药大学 | Extract for repairing damaged islet cells and improving islet cell functions and application |
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