CN105541687B - A kind of method of the separated in synchronization from orange peel and purifying β kryptoxanthin and stigmasterol - Google Patents
A kind of method of the separated in synchronization from orange peel and purifying β kryptoxanthin and stigmasterol Download PDFInfo
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- CN105541687B CN105541687B CN201510941144.1A CN201510941144A CN105541687B CN 105541687 B CN105541687 B CN 105541687B CN 201510941144 A CN201510941144 A CN 201510941144A CN 105541687 B CN105541687 B CN 105541687B
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- kryptoxanthin
- stigmasterol
- orange peel
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- synchronization
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
Abstract
The present invention disclose a kind of method that the separated in synchronization from orange peel purifies β kryptoxanthin and stigmasterol, step one, orange peel is dried and is milled；Step 2, pretreated raw material is extracted with absolute ethyl alcohol, be concentrated under reduced pressure to give total ester extract；Step 3, total ester extract is dissolved in extract solution is obtained in n-hexane, then to adding the KOH ethanol solutions to carry out saponification in extract solution, then extracted, finally washed and be concentrated under reduced pressure；Step 4, isolated and purified using chromatography, collect the eluent consistent with standard items；Step 5, Double solvent method crystallization is carried out to the concentrate of the eluent from n-hexane acetone first, crystallize out stigmasterol crystal, then crystallized from ether methyl alcohol, crystallize out β kryptoxanthin crystal.Using a kind of separated in synchronization from orange peel purifying β kryptoxanthin of the invention and the method for stigmasterol, β kryptoxanthin and stigmasterol can be extracted from orange peel simultaneously, method simple practical, good separating effect, the wherein purity of β kryptoxanthin are up to 98.48%.
Description
Technical field
The present invention relates to the separated in synchronization from orange peel and the technical matters and parameter of purifying β-kryptoxanthin and stigmasterol.
Background technology
β-kryptoxanthin is one kind of carotenoid Lutein, various with anticancer, anti-oxidant, suppression osteoporosis etc.
Physiological function, structural formula is as follows：
It is primarily present in higher plant, fungi, blue-green algae etc.；Recent studies suggest that, β-kryptoxanthin or one kind are good
Vitamin A precursor material.
Phytosterol is a kind of natural active matter being present in plant, be plant constitute cell membrane into point it
One, be also various hormones, vitamin D and steroidal compounds synthesis precursor, with anticancer, anti-inflammatory, anti-oxidant, reduction blood fat and
The physiological functions such as cholesterol, reduction coronary heart disease generation.Stigmasterol is one of Typical Representative of phytosterol, and structural formula is as follows：
It is primarily present in all kinds of plants and grease deodorized distillate.Stigmasterol is special except the general pharmacology with phytosterol
Outside property, also it is mainly used in synthesizing various hormones and vitamin D3, it is widely used in biological and pharmaceuticals industry.Because orange peel comes
Source is easy and cost is relatively low, and natural β-kryptoxanthin is extracted from orange peel turns into the main path for obtaining β-kryptoxanthin；Orange peel
In in addition to containing pectin, cellulose, pigment, also containing bioactivators such as flavones, sterols, but at present on being carried from skin slag
The research for taking stigmasterol is rarely reported.
Described content in documents below, can be as β-kryptoxanthin and the judging basis of stigmasterol：1st, friend Liu Yu is red
The extraction separation of potato cauline leaf chemical composition and Structural Identification [D] Jilin University, 2013；2nd, in Liu Zhihua, Yang Zhixue common callas
The separation of constituent phytosterols and Structural Identification [J] Chinese pharmacists, 2007,10 phases:978-979.DOI:doi:10.3969/
j.issn.1008-049X.2007.10.015；3rd, well phoenix, Wang Li, Xu Shuanshuan wait the separation of beta-cryptoxanthin in capsicums to prepare
[J] Food Sciences, the 2013, the 6th phase:10-13；4、Khachik,F,Chang,ANGana,A,Mazzola,E.Partial
synthesis of(3R,6'R)-alpha-cryptoxanthin and(3R)-beta-cryptoxanthin from(3R,
3'R,6'R)-lutein[J].Journal of Natural Products,2007,70(2):220-226.
The content of the invention
A kind of method that the present invention provides separated in synchronization from orange peel and purifying β-kryptoxanthin and stigmasterol, can obtain simultaneously
Obtain the β-kryptoxanthin and stigmasterol of high-purity.
Technical scheme is as follows：
A kind of method of separated in synchronization from orange peel and purifying β-kryptoxanthin and stigmasterol, it is critical only that including following
Step：
Step one, orange peel is dried and is milled；
Step 2, pretreated raw material is extracted with absolute ethyl alcohol, be concentrated under reduced pressure to give total ester extract；
Step 3, total ester extract is dissolved in extract solution is obtained in n-hexane first, then to extract solution
Middle addition KOH- ethanol solutions carry out saponification, are extracted after the completion of saponification, finally wash and are concentrated under reduced pressure；
Step 4, isolated and purified using chromatography, be control with β-kryptoxanthin standard items, collect simultaneously containing sterol and β-
The eluent of kryptoxanthin；
Step 5, the eluent that will be obtained in step 4 are concentrated, and obtain concentrate；
Step 6, the concentrate of eluent first from n-hexane-acetone to being obtained in step 4 carry out Double solvent method
Crystallization, crystallizes out stigmasterol crystal, then the washing lotion after above-mentioned removal stigmasterol crystal is concentrated again, obtain mainly containing β-
The concentrate of kryptoxanthin, is finally crystallized from ether-methanol, is just crystallized out β-kryptoxanthin crystal.
In above-mentioned steps two, citrus peel meal is extracted under conditions of 38~45 DEG C.
In above-mentioned steps three, the mass concentration of the extract solution is 0.046~0.056%, and the KOH- ethanol is molten
The mass concentration of liquid is 8~12%, and the extract solution is 1 with the volume ratio of KOH- ethanol solutions:1, saponification time is
12h。
In above-mentioned steps three, after the completion of saponification, isometric n-hexane is added to be extracted, isolated n-hexane
Phase, then n-hexane phase is washed with the NaCl aqueous solution that isometric mass concentration is 0.5%, finally it is concentrated under reduced pressure.
In above-mentioned steps four, using silica gel column chromatography separating purification, using n-hexane wet method dress post, using n-hexane：Third
Ketone：Methyl alcohol=92.5:7:0.5 volume ratio isocratic elution, and detected with thin-layered chromatography.
In above-mentioned steps six, after crystallizing out stigmasterol crystal, crystal is cleaned with n-hexane, until crystal is colourless；Again will be molten
Liquid carries out concentrate drying, and dried material is crystallized from ether-methanol finally, obtains β-kryptoxanthin crystal, is used in combination
Methyl alcohol cleans crystal, untill methyl alcohol cleaning fluid is colourless.
The condition of thin-layer chromatography is in above-mentioned steps four：Solvent is petroleum ether:Ether=7:3, developer is 10% sulphur
Acid-absolute ethyl alcohol, 95 DEG C of baking 2min.
Beneficial effect：Using a kind of separated in synchronization from orange peel of the invention and the side of purifying β-kryptoxanthin and stigmasterol
Method, can extract β-kryptoxanthin and stigmasterol from orange peel simultaneously, and method simple practical, good separating effect, separation product is pure
Degree is high, is adapted to industrialized production.
Brief description of the drawings
Fig. 1 is the flow chart that the present invention is obtained；
Fig. 2 is the infrared spectrogram of the stigmasterol that the present invention is obtained；
Fig. 3 is the stigmasterol that the present invention is obtained1H-NMR spectrum；
Fig. 4 is the stigmasterol that the present invention is obtained13C-NMR spectrograms；
Fig. 5 is β-kryptoxanthin that the present invention is obtained1H-NMR spectrum；
Fig. 6 is the high-efficient liquid phase chromatogram of β-kryptoxanthin standard items；
Fig. 7 is the high-efficient liquid phase chromatogram of β-kryptoxanthin that the present invention is obtained；
The microphoto of β-kryptoxanthin that Fig. 8 present invention is obtained；
The microphoto of the stigmasterol that Fig. 9 present invention is obtained.
Specific embodiment
With reference to embodiment, the invention will be further described.
A kind of method of purifying β-kryptoxanthin of the separated in synchronization from orange peel and stigmasterol, comprises the following steps：
Step one, by orange peel in drying and be milled under 40 DEG C of temperature conditionss；
Step 2, in 38~45 DEG C of water-bath, extract pretreated raw material 2 times with absolute ethyl alcohol, merge and extract
Liquid, is concentrated under reduced pressure to give total ester extract；
Step 3, total ester extract is dissolved in n-hexane obtains extract solution first, the extract solution
Mass concentration is 0.046~0.056%, then carries out saponification to addition KOH- ethanol solutions in extract solution, the KOH-
The mass concentration of ethanol solution is 8~12%, and the extract solution is 1 with the volume ratio of KOH- ethanol solutions:1, during saponification
Between be 12h；After the completion of saponification, isometric n-hexane is added to be extracted, isolated n-hexane phase, then with isometric
Mass concentration be 0.5% the NaCl aqueous solution washing n-hexane phase, be finally concentrated under reduced pressure.
Step 4, using silica gel column chromatography separating purification, using n-hexane wet method dress post, using n-hexane：Acetone：Methyl alcohol
=92.5:7:0.5 volume ratio isocratic elution, and detected with thin-layered chromatography, it is control with β-kryptoxanthin standard items, collect master
Contain the eluent of β-kryptoxanthin and stigmasterol；
The condition of the thin-layer chromatography is：Solvent is petroleum ether:Ether=7:3, developer is 10% sulfuric acid-anhydrous second
Alcohol, 95 DEG C of baking 2min.
Step 5, Double solvent method crystallization is carried out to the concentrate of the eluent from n-hexane-acetone first, wherein third
Ketone is the good solvent of stigmasterol, and n-hexane is the poor solvent of stigmasterol, stigmasterol crystal is crystallized out under the conditions of 25 DEG C, with just
Hexane cleans crystal, until crystal is colourless；
Solution is carried out into concentrate drying again, dried material is crystallized from ether-methanol finally, wherein ether
It is the good solvent of β-kryptoxanthin crystal, methyl alcohol is the poor solvent of β-kryptoxanthin, crystallization obtains β-kryptoxanthin under the conditions of 25 DEG C
Crystal, and clean crystal with methyl alcohol, the purity of its β-kryptoxanthin is up to 98.48%.
The identification of crystallized product：
First, the infrared spectrum analysis of white crystals
Fig. 2 is stigmasterol crystal infrared spectrogram, and Fig. 2 is analyzed：3500-3200cm-1Place is wide and strong bands of a spectrum are
The absorption band that O-H stretching vibrations cause, it is a key character bands of a spectrum of fatty alcohol.2870 and 2949 is the C-H of methyl
Stretching vibration peak, 1448 and 1373 for methylene C-H deformation vibration the absworption peaks.The relatively low weak peak of intensity is C=C at 1651
The stretching vibration absworption peak of double bond, weak peak is the stretching vibration absworption peak of C-O keys, the above infrared spectrum characteristic peak at 1060
The compound is embodied for steroidal compounds.
2nd, crystallized product nuclear magnetic spectrum analysis
Above β-kryptoxanthin crystal and stigmasterol crystal are carried out into nmr analysis, as a result as shown in Fig. 3 to Fig. 5, wherein Fig. 3
It is above stigmasterol1H-NMR spectrum, Fig. 4 is above stigmasterol13C-NMR spectrograms, Fig. 5 is above β-kryptoxanthin1H-
NMR spectra.
Fig. 3 is analyzed：1H-NMR(400MHz,CDCl3) 6 methyl signals peaks are had in spectrum, it is respectively 0.69 (d, J
=7.3Hz, 3H)；0.74–0.93(m,9H)；0.93-1.01(m,6H).In 5.02 (dd, J=15.2,8.6Hz, 1H) and 5.15
(dd, J=15.2,8.6Hz, 1H) is the trans alkene hydrogen signal in 22 and 23 double bonds；5.35 (dt, J=4.8,1.9Hz, 1H) are
The olefinic carbon hydrogen signal of C-6；One company's oxygen carbon signal 3.51 (m, 1H)；
Fig. 4 is analyzed：13C-NMR (125MHz, CDCl3) spectrum provide 29 carbon signals altogether.δ140.79、δ138.32、
δ 129.33, four olefinic carbon signals of δ 121.72 (C-5, C-22, C-23, C-6), wherein δ 140.79 (C-5) are quaternary carbon signal；In δ
42.34 (C-13), δ 36.54 (C-10) place are 2 signal peaks of quaternary carbon；Signal peak at δ 71.82 (C-3) place is one and oxygen
Connected carbon signal, remaining carbon signal is the carbon signal of alkyl, and the content according to described in existing document is inferred, the sterol material
It is probably stigmasterol.
Fig. 5 is analyzed：1H-NMR(400MHz,CDCl3) 10 methyl signals peaks are had in spectrum, respectively：1.03
(s, Me-16 ', Me-17 '), 1.07 (s, Me-16, Me-17), 1.72 (s, Me-18 '), 1.74 (s, Me-18), 1.97 (s, Me-
19,Me-20,Me-19′,Me-20′).Additionally, 4.02 (m, 1H) are O-H alcoholic extract hydroxyl group signal peaks；1.0-2.0 is alkane=CH- knots
Structure signal peak；2.0-3.0 is alkene-CH=CH2 signal peaks；6.0-7.0 is aromatic hydrocarbons CH2-C=signal peaks.The result and document
Described content is basically identical.
The analysis of Fig. 2, Fig. 3, Fig. 4 and Fig. 5 is understood, the product that can be obtained with the preliminary judgement present invention as β-kryptoxanthin and
Stigmasterol.
3rd, crystallized product thin-layer chromatographic analysis
Above β-kryptoxanthin crystal and stigmasterol crystal are carried out into thin-layer chromatographic analysis, and using β-kryptoxanthin standard items and
Stigmasterol standard items are contrasted.Thin-layer chromatography condition：Solvent is petroleum ether:Ether=7:3, developer is 10% sulfuric acid-anhydrous
Ethanol, 95 DEG C of baking 2min.Determine the R of each groupfValue, the results are shown in Table 1：
The R of table 1, crystallized product and standard itemsfValue
As can be seen from Table 1, the R of above crystal and corresponding standard itemsfValue is equal, in the base of above nuclear magnetic spectrum analysis
On plinth, it is possible to determine that the product that the present invention is obtained is very likely β-kryptoxanthin and stigmasterol.And after colour developing is heated, β-hidden Huang
Element is in aubergine in dark blue-green, stigmasterol, consistent with associated description.
4th, efficient liquid phase chromatographic analysis
Efficient liquid phase chromatographic analysis are carried out to β-kryptoxanthin standard items and β-kryptoxanthin crystallization；High-efficient liquid phase chromatogram condition
For：Mobile phase A is ethyl acetate, and Mobile phase B is 90% acetonitrile, A:B=40:60, isocratic elution；Flow velocity is 1mL/min；Post
Temperature is 30 DEG C.Fig. 6 and Fig. 7 are respectively the high-efficient liquid phase chromatogram of β-kryptoxanthin standard items and β-kryptoxanthin crystallization.The He of comparison diagram 6
Fig. 7 understands that the appearance time of the β that the present invention is obtained-kryptoxanthin crystallization is 14.073min, during with β-kryptoxanthin standard items appearance
Between 14.050min be consistent, i.e., differentiate from high performance liquid chromatography and understand, the β-kryptoxanthin crystallization as β that the present invention is obtained-hidden
Flavine.
5th, crystalline mi morphological analysis
Fig. 8 and Fig. 9 are respectively the microphoto of product β-kryptoxanthin of the present invention and stigmasterol, it can be seen from figure 7 that β-
Kryptoxanthin in the form of sheets, with metallic luster；Stigmasterol is mainly acicular crystal, and this result is consistent with document report.
In sum, using the method for the present invention, β-kryptoxanthin and stigmasterol can be separated and purify from orange peel simultaneously.
Finally it should be noted that foregoing description is only the preferred embodiments of the present invention, the ordinary skill people of this area
Member on the premise of without prejudice to present inventive concept and claim, can make table as multiple types under enlightenment of the invention
Show, such conversion is each fallen within protection scope of the present invention.
Claims (7)
1. a kind of separated in synchronization from orange peel and purifying β-kryptoxanthin and stigmasterol method, it is characterised in that including following step
Suddenly：
Step one, orange peel is dried and is milled；
Step 2, pretreated raw material is extracted with absolute ethyl alcohol, be concentrated under reduced pressure to give total ester extract；
Step 3, the step 2 total ester extract of gained is dissolved in extract solution is obtained in n-hexane first, then it is molten to extract
KOH- ethanol solutions are added in liquid carries out saponification, is extracted after the completion of saponification, finally washes and is concentrated under reduced pressure；
Step 4, isolated and purified using chromatography, be control with β-kryptoxanthin standard items, collected and contain sterol and β-hidden Huang simultaneously
The eluent of element；
Step 5, the eluent that will be obtained in step 4 are concentrated, and obtain concentrate；
Step 6, first from n-hexane-acetone to step 5 gained eluent concentrate carry out Double solvent method crystallization, crystallize
Go out stigmasterol crystal, then the washing lotion after above-mentioned removal stigmasterol crystal is concentrated, obtain the mainly concentration containing β-kryptoxanthin
Thing, is finally crystallized from ether-methanol, crystallizes out β-kryptoxanthin crystal.
2. the method that a kind of separated in synchronization from orange peel according to claim 1 purifies β-kryptoxanthin and stigmasterol, its
It is characterised by：In the step 2, citrus peel meal is extracted under conditions of 38~45 DEG C.
3. the method that a kind of separated in synchronization from orange peel according to claim 1 and 2 purifies β-kryptoxanthin and stigmasterol,
It is characterized in that：In the step 3, the mass concentration of the extract solution is 0.046~0.056%, the KOH- ethanol
The mass concentration of solution is 8~12%, and the extract solution is 1 with the volume ratio of KOH- ethanol solutions:1, saponification time is
12h。
4. the method that a kind of separated in synchronization from orange peel according to claim 3 purifies β-kryptoxanthin and stigmasterol, its
It is characterised by：In the step 3, after the completion of saponification, add isometric n-hexane to be extracted, it is isolated just oneself
Alkane phase, then n-hexane phase is washed with the NaCl aqueous solution that isometric mass concentration is 0.5%, finally it is concentrated under reduced pressure.
5. the method that a kind of separated in synchronization from orange peel according to claim 1 purifies β-kryptoxanthin and stigmasterol, its
It is characterised by：In the step 4, using silica gel column chromatography separating purification, using n-hexane wet method dress post, using n-hexane：Third
Ketone：Methyl alcohol=92.5:7:0.5 volume ratio isocratic elution, and detected with thin-layered chromatography.
6. a kind of separated in synchronization from orange peel purifying β-kryptoxanthin according to claim 1 or 2 or 5 and the side of stigmasterol
Method, it is characterised in that：In the step 6, after crystallizing out stigmasterol crystal, crystal is cleaned with n-hexane, until crystal is colourless；
Washing lotion is carried out into concentrate drying again, dried material is crystallized from ether-methanol finally, obtain β-kryptoxanthin brilliant
Body, and crystal is cleaned with methyl alcohol, untill colourless for the methyl alcohol for cleaning.
7. the method that a kind of separated in synchronization from orange peel according to claim 5 purifies β-kryptoxanthin and stigmasterol, its
The condition for being characterised by thin-layer chromatography in step 4 is：Solvent is petroleum ether:Ether=7:3, developer is 10% sulfuric acid-nothing
Water-ethanol, 95 DEG C of baking 2min.
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| CN106380501B (en) * | 2016-08-09 | 2018-04-24 | 右江民族医学院 | A kind of method that stigmasterol is extracted in the stem from Job's tears |
| CN109717485A (en) * | 2019-02-15 | 2019-05-07 | 湖北土老憨调味食品股份有限公司 | It is a kind of from tangerine orange produce tangerine vinegar after tangerine slag in continuously acquire the preparation method of orange pigment and dietary fiber |
| CN110208443A (en) * | 2019-06-21 | 2019-09-06 | 广东食品药品职业学院 | A kind of method of carotenoid in extraction Mango Fruit |
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| CN101863955A (en) * | 2010-05-10 | 2010-10-20 | 孙志高 | Process for hierarchically extracting limonin, flavonoid and dietary fiber from orange peel residues |
| CN102057048A (en) * | 2008-04-09 | 2011-05-11 | 索拉兹米公司 | Direct chemical modification of microbial biomass and microbial oils |
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| CN102057048A (en) * | 2008-04-09 | 2011-05-11 | 索拉兹米公司 | Direct chemical modification of microbial biomass and microbial oils |
| CN101863955A (en) * | 2010-05-10 | 2010-10-20 | 孙志高 | Process for hierarchically extracting limonin, flavonoid and dietary fiber from orange peel residues |
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| 温州蜜柑皮β-隐黄素的分离和纯化;孙志高 等;《食品科学》;20131231;第34卷(第12期);第11-15页 * |
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