CN105085268B - A kind of method being enriched with natural methyl jasmonate from oil of aglaia odorate - Google Patents
A kind of method being enriched with natural methyl jasmonate from oil of aglaia odorate Download PDFInfo
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Abstract
The invention discloses a kind of method being enriched with natural methyl jasmonate from oil of aglaia odorate, first extract preparation, take petroleum ether, methanol, water, mix according to volume ratio 2 8:1 7:0.3 1, fully stratification after mixing, upper and lower phase is retained separately in different vessels, obtains upper phase solution A and lower phase B solution；Secondly MeJA extract and separate, after oil of aglaia odorate is added upper phase solution A dissolving, add the extraction of isopyknic lower phase B solution, the mass volume ratio that wherein orchid oil and upper phase solution A are dissolved is 1:1 10, lower phase solution is released after layering, upper phase solution continues to add lower phase B solution and extracts 1 time or repeatedly, merge and extract all lower phase solution every time, be concentrated under reduced pressure to give enrichment positions C of MeJA；Last column chromatographic isolation and purification MeJA.This technique is simple, and easy to operate, equipment investment is few, and gained methyl jasmonate compound purity is high, and quality is good.
Description
Technical field
The invention belongs to chemical technology field, relate to the method for the natural methyl jasmonate of separation and concentration from oil of aglaia odorate extractum.
Background technology
Methyl jasmonate, Chinese: methyl jasmonate, pentenyl Ketocyclopentane-3-methyl acetate, English name: Methyl jasmonate,
Write a Chinese character in simplified form: MeJA, chemical name: 2-(1R, 2R)-3-ketone group-2-((Z)-2-heptene) 2-Cyclopentylacetic acid methyl ester,
2-((1R, 2R)-3-oxo-2-((Z)-pent-2-enyl) cyclopentyl) acetate, CAS:1211-29-6, molecular formula: C13H20O3, point
Son amount: 224.3, structural formula is:
Methyl jasmonate, colourless to weak yellow liquid, boiling point: higher than 300 DEG C, density: 1.02；Flash-point: 156 DEG C, index of refraction 20 DEG C:
1.473-1.477；It is practically insoluble in water, is dissolved in ethanol and oils, strong, soft and happy jasmin, compares MDJ
Fragrance is lasting.Be naturally occurring in Spanish jasmin, Tunisia Herba Rosmarini Officinalis, Fructus Piperis, Herba Menthae Rotundifoliae, in tree orchid and Folium Camelliae sinensis.Can be widely applied to manually prepare
Jasmin quintessence oil, it is also possible to make essence have the characteristic perfume of natural Flos Jasmini Sambac in jasmine perfume base, but the most expensive, now it is mainly used in height
In the shelves formula such as perfume fragrance, cosmetic essence.Current chemosynthesis circuit is a lot, but the most complicated.
Methyl jasmonate is a kind of micromolecular compound with several functions.Methyl jasmonate occupies important ground in essence and flavoring agent field
Position, the flowers and plants with strong lasting similar jasmin quintessence oil are fragrant and fragrant and sweet, are generally used in the cosmetics of super quality owing to it is expensive.Meanwhile, jasmine
Jasmine keto acid esters is novel phytohormone, it is possible to the aging of involved in plant organ, induction its secondary metabolites content, induction fruit maturation, anti-cold
The physiological process such as cold injury evil.Additionally, show good anti-tumor activity at field of medicaments jasmonate and derivant thereof, although it is controlled in tumor
Effect and antitumor mechanism in treatment also need to widely further investigate, but can reduce normal cell tissue poison compared with existing chemotherapeutic
Property reaction, and the tumor cell of many drug resistances is also had certain curative effect, both can also be as preventive usage as therapeutic medication.
In view of the huge Development volue that jasmonate is potential, find the more natural plants of content or develop new preparation method and will become jasmone
The top priority of acid esters research.
The traditional preparation method of jasmonate is chemosynthesis, and synthesis technique step is the most more complicated, and product is the mixture of isomer, single
One isomer is difficult to obtain, and is chemicals.
The methyl jasmonate of plant origin is single configuration methyl jasmonate, and is natural methyl jasmonate.Current natural (1S,2S)-3-oxo-2-(2'-cis-pentenyl)cyclopentan-1-acetate first
Ester is typically found in plants essential oil or extractum or absolute oil, and such as oil of aglaia odorate volatile ingredient 86 kinds, methyl jasmonate accounts for about 4.5%.Conventional skill
Art such as distillation, column chromatography etc. is difficult to separation energy and obtains the methyl jasmonate of high-load.
Summary of the invention
The problems referred to above existed for prior art, it is an object of the invention to provide a kind of simple, and the preparation side that natural methyl jasmonate content is high
Method.
For achieving the above object, the present invention adopts the following technical scheme that a kind of method being enriched with natural methyl jasmonate from oil of aglaia odorate, including
Following steps:
Step 1, extract is prepared
Taking petroleum ether, methanol, water, mix according to volume ratio 2-8:1-7:0.3-1, fully stratification after mixing, separates upper and lower phase
It is stored in different vessels, obtains upper phase solution A and lower phase B solution；
Step 2, MeJA extract and separate
After oil of aglaia odorate adds upper phase solution A dissolving, adding the extraction of isopyknic lower phase B solution, wherein orchid oil dissolves with upper phase solution A
Mass volume ratio be 1:1-10, release lower phase solution after layering, upper phase solution continues to add lower phase B solution and extracts 1 time or repeatedly, merge every time
Extract all lower phase solution, be concentrated under reduced pressure to give enrichment positions C of MeJA；
Step 3, column chromatographic isolation and purification MeJA
MeJA enrichment positions C step 2 being obtained by extraction is splined on silica gel column chromatography after adding silica gel mixed sample, wherein enrichment positions C with mix sample silica gel
Ratio is 1:1-2, with petroleum ether-ethyl acetate system gradient elution, when eluent ratio is 5-40:1, collects eluent, concentrating under reduced pressure
Obtain enrichment positions D of MeJA after purification.
As optimization, in described step 1, petroleum ether, methanol, water, according to volume ratio 5:4:1；
The mass volume ratio that in described step 2, orchid oil and upper phase solution A are dissolved is 1:5；
In described step 3 when eluent ratio is 20:1, collect eluent, be concentrated under reduced pressure to give enrichment positions D of MeJA after purification.
The present invention is found by research, and two-phase extraction system contributes to concentration and separation methyl jasmonate from oil of aglaia odorate.Further study show that,
The three component two-phase extraction systems being made up of petroleum ether, methanol, water are more beneficial for the enrichment of methyl jasmonate.Further find, petroleum ether,
Methanol, water three component can be divided into upper and lower two-layer according to after certain ratio mixing, and upper strata is upper phase solution A, and lower floor is lower phase B solution.Enter again
One step finds, upper phase solution A and lower phase B solution jointly extract methyl jasmonate from oil of aglaia odorate, and concentration and separation effect is best.Enter one again
Step finds, oil of aglaia odorate is initially charged phase solution A, then adds lower phase B solution, and effect of extracting is better than oil of aglaia odorate and is initially charged lower phase B solution, then adds
Upper phase solution A extracts.Because when oil of aglaia odorate mixes with 1:5 mass volume ratio with lower phase B solution, if tree orchid oil is initially charged lower phase B
Solution, then oil of aglaia odorate is difficult to be completely dissolved in lower phase B solution, thus when being subsequently added phase solution A, extraction efficiency is poor.Certainly under increasing
Phase B solution volume until add oil of aglaia odorate dissolve if, one is to increase B solution cost, and two is to need to increase more solution A to extract, from
And increase solution A cost, three are as solution A and B solution increase, and wastewater flow rate increases.Further finding, the amount that lower phase B solution adds should
Equal-volume is in upper phase solution A, the too much or very few two-phase laminated flow that is all unfavorable for as far as possible, thus causes enriched product quantity few, and content is low.
Further finding, two-phase extracting process combines with simple silica gel column chromatography, can remove other compositions in enriched substance further, improves richness
The content of methyl jasmonate in collection thing.And the extraction of single method such as two-phase or column chromatography all can not significantly improve enriched product methyl jasmonate and contain
Amount.
Relative to prior art, present invention have the advantage that
1, the methyl jasmonate compound during the present invention uses the method purification oil of aglaia odorate that double solvents enrichment and column chromatography combine, separates
Degree is good, and gained methyl jasmonate compound purity is high, and quality is good；Methyl jasmonate enriching and purifying effect is obvious, improves (1S,2S)-3-oxo-2-(2'-cis-pentenyl)cyclopentan-1-acetate first
The valid density of ester.
2, the invention provides a new way for separation and concentration methyl jasmonate from plant, the plant origin containing methyl jasmonate enriches,
And technique is simple, easy to operate, equipment investment is few, has a good application prospect.
Detailed description of the invention
Below the present invention is described in further detail.
The present invention extracts methyl jasmonate through processing steps such as extract preparation, extract and separate, column chromatographies, and concentration effect is jasmine from tree orchid quintessence oil
Jasmine keto acid methyl ester one-component content brings up to more than 90% from 4.5%, and methyl jasmonate enriching and purifying effect is obvious, improves methyl jasmonate
Valid density, present invention process is easy, and bioaccumulation efficiency is high, and equipment investment is few, has a good application prospect.It addition, the present invention proposes from tree orchid
The method of the natural methyl jasmonate of separation and concentration in caul-fat extractum, enriches raw material prepared by natural methyl jasmonate compound separation and Extraction
Source, the flavouring exploitation of the most natural methyl jasmonate compound, it is simultaneously also beneficial to alleviate because natural methyl jasmonate price is high, and limits
A difficult problem for the development and application research of natural methyl jasmonate compound.
Embodiment 1: a kind of method being enriched with natural methyl jasmonate from oil of aglaia odorate, comprises the steps:
Step 1, extract is prepared
Take petroleum ether (100ml), methanol (80ml), water (20ml), mix according to volume ratio 5:4:1, fully stand after mixing and divide
Layer, is retained separately upper and lower phase in different vessels, obtains upper phase solution A and lower phase B solution.
Step 2, MeJA extract and separate
Take oil of aglaia odorate 6g, add phase solution A on 30mL and be transferred in separatory funnel after dissolving, add the extraction of isopyknic lower phase B solution,
Releasing lower phase solution after layering, upper phase solution continues to add lower phase B solution (30 milliliters) and extracts 2 times, merges and extracts all lower phase solution every time, subtracts
Pressure is concentrated to give enrichment positions C of MeJA.Enrichment positions C taking a small amount of MeJA adds after dichloromethane solvent dilutes for GC detection analysis, knot
Fruit display methyl jasmonate accounts for 44.2%, light yellow transparent liquid.
Step 3, column chromatographic isolation and purification MeJA
It is splined on silica gel column chromatography after the silica gel mixed sample of the MeJA enrichment positions C 1 times of enrichment positions C mass of addition step 2 being obtained by extraction,
With petroleum ether-ethyl acetate system gradient elution, when eluent ratio is 20:1, collects eluent, be concentrated under reduced pressure to give the enrichment portion of MeJA
Position D, colourless transparent liquid.Take MeJA enrichment positions D and add q. s. methylene chloride dissolved dilution on a small quantity, be used for after crossing 0.22 μm organic facies filter membrane
GC analyzes, and result display methyl jasmonate accounts for 90%.
Embodiment 1 is given below and is enriched with the comparative example of natural methyl jasmonate method:
Comparative example 1: silica gel column chromatography concentration and separation MeJA
Step 1, loading
Choosing 30 × 250mm chromatographic column, dry method loads 200-300 mesh silica gel 50g, and after paving, decompression is bled and made silica gel filling closely, then
Take the direct loading of oil of aglaia odorate 5g.
Step 2, eluting
After sample adsorbs on a silica gel column completely, successively with normal hexane, normal hexane-dichloromethane 1:1 (volume ratio), dichloromethane, acetic acid
Ethyl ester each 300mL eluting.Collect dichloromethane eluant, be concentrated under reduced pressure to give enrichment positions D of MeJA, colourless transparent liquid.
Step 3, Analysis and Identification
Taking MeJA enrichment positions D and add q. s. methylene chloride dissolved dilution on a small quantity, analyze for GC after crossing 0.22 μm organic facies filter membrane, result shows
Methyl jasmonate accounts for 18.23%.
Comparative example 2: alumina column chromatography concentration and separation MeJA
Step 1, loading
Take in aluminium oxide 100g to 250ml beaker, add petroleum ether (200ml) stirring and pour glass chromatography column into bubble-free, treat that nature sinks
Aglaia odorata oil 10g 10mL petroleum ether dilution loading is taken after blood pressure lowering is real.
Step 2, eluting
After sample adsorbs completely, successively with petroleum ether, petroleum ether-dichloromethane 1:1 (volume ratio), dichloromethane, each 400mL of ethyl acetate
Eluting, collects each section of flow point, petroleum ether-dichloromethane 1:1 (volume ratio) and dichloromethane position is merged, is concentrated under reduced pressure to give the richness of MeJA
Collection position D, colourless transparent liquid.
Step 3, Analysis and Identification
Enrichment positions D taking MeJA uses suitable dichloromethane dissolved dilution on a small quantity, analyzes for GC after crossing 0.22 μm organic facies filter membrane, and result shows
Methyl jasmonate accounts for 35.1%.
Embodiment 2-6, uses method same as in Example 1, the except for the difference that proportioning of parameter, concrete such as table 1:
Table 1
The detection method of the content of the enrichment positions D methyl jasmonate of the MeJA that embodiment 2-6 obtains is same as in Example 1, and testing result is such as
Table 2.
Table 2
Finally illustrating, above example is only in order to illustrate technical scheme and unrestricted, although carrying out the present invention with reference to preferred embodiment
Describe in detail, it will be understood by those within the art that, technical scheme can be modified or equivalent, without deviating from
The objective of technical solution of the present invention and scope, it all should be contained in the middle of scope of the presently claimed invention.
Claims (2)
1. the method being enriched with natural methyl jasmonate from oil of aglaia odorate, it is characterised in that include as
Lower step:
Step 1, extract is prepared
Take petroleum ether, methanol, water, mix according to volume ratio 2-8:1-7:0.3-1, fully stand after mixing
Layering, is retained separately upper and lower phase in different vessels, obtains upper phase solution A and lower phase B solution；
Step 2, MeJA extract and separate
After oil of aglaia odorate is added upper phase solution A dissolving, add the extraction of isopyknic lower phase B solution, wherein
The mass volume ratio that orchid oil dissolves with upper phase solution A is 1g:1-10ml, releases lower phase solution after layering,
Upper phase solution continues to add lower phase B solution and extracts 1 time or repeatedly, merge and extract all lower phase solution every time, subtract
Pressure is concentrated to give enrichment positions C of MeJA；
Step 3, column chromatographic isolation and purification MeJA
MeJA enrichment positions C step 2 being obtained by extraction is splined on silica gel column chromatography after adding silica gel mixed sample,
Wherein enrichment positions C is 1:1-2 with mixing sample silica gel ratio, with petroleum ether-ethyl acetate system gradient elution,
When eluent ratio is 5-40:1, collects eluent, be concentrated under reduced pressure to give the enrichment portion of MeJA after purification
Position D.
2. the method being enriched with natural methyl jasmonate from oil of aglaia odorate as claimed in claim 1, it is special
Levying and be, in described step 1, petroleum ether, methanol, water, according to volume ratio 5:4:1；
The mass volume ratio that in described step 2, orchid oil and upper phase solution A are dissolved is 1g:5ml；
In described step 3 when eluent ratio is 20:1, collect eluent, be concentrated under reduced pressure to give purification
Enrichment positions D of rear MeJA.
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Application publication date: 20151125 Assignee: Shenzhen Haoyu Biological Technology Co.,Ltd. Assignor: BOTON (SHANGHAI) BIOTECHNOLOGY Co.,Ltd. Contract record no.: 2017440020058 Denomination of invention: Method for enriching natural MeJA (methyl jasmonate) from aglaia odorate oil Granted publication date: 20161130 License type: Common License Record date: 20170726 |
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Application publication date: 20151125 Assignee: Shenzhen xinshengrui Biotechnology Co.,Ltd. Assignor: BOTON (SHANGHAI) BIOTECHNOLOGY Co.,Ltd. Contract record no.: X2022980009383 Denomination of invention: A method for enriching natural methyl jasmonate from magnolia oil Granted publication date: 20161130 License type: Common License Record date: 20220705 |
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