CN105541687A - Method for synchronously separating and purifying beta-cryptoflavin and stigmasterol in orange peel - Google Patents
Method for synchronously separating and purifying beta-cryptoflavin and stigmasterol in orange peel Download PDFInfo
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- CN105541687A CN105541687A CN201510941144.1A CN201510941144A CN105541687A CN 105541687 A CN105541687 A CN 105541687A CN 201510941144 A CN201510941144 A CN 201510941144A CN 105541687 A CN105541687 A CN 105541687A
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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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- 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
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Abstract
The invention discloses a method for synchronously separating and purifying beta-cryptoflavin and stigmasterol in orange peel. The method comprises 1, drying orange peel and grinding the dried orange peel, 2, carrying out extraction on the pretreated raw material through anhydrous ethanol and carrying out reduced pressure condensation to obtain total ester extract, 3, dissolving the total ester extract in n-hexane to obtain an extract solution, adding a KOH-ethanol solution into the extract solution, carrying out a saponification reaction process, carrying out extraction and carrying out water washing and reduced pressure condensation, 4, carrying out separation purification through a chromatography method and collecting the eluate the same to the standard substance, and 5, carrying out double-solvent crystallization on the eluate concentrate through n-hexane-acetone to obtain stigmasterol crystals and carrying out crystallization through ether-methanol to obtain beta-cryptoflavin crystals. The method can extract beta-cryptoflavin and stigmasterol from orange peel, is simple and practical, has good separation effects and realizes beta-cryptoflavin purity of 98.48%.
Description
Technical field
The present invention relates to technical matters and the parameter of separated in synchronization and purifying β-cryptoxanthin and Stigmasterol from peel of Citrus reticulata Blanco.
Background technology
β-cryptoxanthin is the one of carotenoid Lutein, have anticancer, anti-oxidant, suppress the different physiological roles such as osteoporosis, structural formula is as follows:
It is mainly present in higher plant, fungi, blue-green algae etc.; Recent research shows, β-cryptoxanthin or a kind of good vitamin A precursor material.
Plant sterol is a kind of natural active matter be present in plant, that plant materials forms one of composition of cytolemma, also be the precursor of multiple hormone, vitamins D and steroidal compounds synthesis, have anticancer, anti-inflammatory, anti-oxidant, reduce blood fat and the physiological function such as cholesterol, the generation of minimizing coronary heart disease.Stigmasterol is one of Typical Representative of plant sterol, and structural formula is as follows:
It mainly exists in all kinds of plant and grease deodorized distillate.Stigmasterol, except the general pharmacology characteristic with plant sterol, is also mainly used in synthesizing various hormone and vitamins D
3, be widely used in biology and pharmaceutical industries.Due to peel of Citrus reticulata Blanco source easily and cost is lower, from orange peel, extract natural β-cryptoxanthin becomes the main path obtaining β-cryptoxanthin; Except containing except pectin, Mierocrystalline cellulose, pigment in orange peel, also containing the biologically active substance such as flavones, sterol, but at present about the rarely seen report of research extracting Stigmasterol from skin slag.
With content described in Publication about Document, can as the judging basis of β-cryptoxanthin and Stigmasterol: 1, Liu Yupeng. the extraction and isolation of sweet potato stem leaf chemical composition and Structural Identification [D]. Jilin University, 2013; 2, Liu Zhihua, Yang Zhixue. the separation of constituent phytosterols and Structural Identification [J] in common calla. Chinese pharmacists, 2007,10 phase: 978-979.DOI:doi:10.3969/j.issn.1008-049X.2007.10.015; 3, well phoenix, Wang Li, Xu Shuanshuan, etc. separation preparation [J] of beta-cryptoxanthin in capsicum. Food science, the 2013,6th phase: 10-13; 4, Khachik, F, Chang, ANGana, A, Mazzola, E.Partialsynthesisof (3R, 6'R)-alpha-cryptoxanthinand (3R)-beta-cryptoxanthinfrom (3R, 3'R, 6'R)-lutein [J] .JournalofNaturalProducts, 2007,70 (2): 220-226.
Summary of the invention
The invention provides a kind of method of separated in synchronization and purifying β-cryptoxanthin and Stigmasterol from peel of Citrus reticulata Blanco, highly purified β-cryptoxanthin and Stigmasterol can be obtained simultaneously.
Technical scheme is as follows:
A method for separated in synchronization and purifying β-cryptoxanthin and Stigmasterol from peel of Citrus reticulata Blanco, its key is to comprise the following steps:
Step one, by peel of Citrus reticulata Blanco dry and abrasive dust;
Step 2, the pretreated raw material of use dehydrated alcohol lixiviate, concentrating under reduced pressure obtains total ester extract;
Step 3, first described total ester extract is dissolved in normal hexane is extracted thing solution, then in extract solution, add KOH-ethanolic soln carry out saponification reaction, extract after saponification reaction completes, finally washing concentrating under reduced pressure;
Step 4, the separation and purification of employing chromatography, with β-cryptoxanthin standard substance for contrast, collect the elutriant simultaneously containing sterol and β-cryptoxanthin;
Step 5, the elutriant obtained in step 4 to be concentrated, obtain enriched material;
Step 6, first normal hexane-acetone is selected to carry out Double solvent method crystallization to the enriched material of the elutriant obtained in step 4, crystallization goes out Stigmasterol crystal, again the washing lotion after above-mentioned removal Stigmasterol crystal is concentrated again, obtain mainly containing the enriched material of β-cryptoxanthin, finally select ether-methanol to carry out crystallization, just crystallizable go out β-cryptoxanthin crystal.
In above-mentioned steps two, under the condition of 38 ~ 45 DEG C, lixiviate is carried out to citrus peel meal.
In above-mentioned steps three, the mass concentration of described extract solution is 0.046 ~ 0.056%, and the mass concentration of described KOH-ethanolic soln is 8 ~ 12%, and the volume ratio of described extract solution and KOH-ethanolic soln is 1:1, and saponification time is 12h.
In above-mentioned steps three, after saponification reaction completes, add isopyknic normal hexane and extract, be separated and obtain normal hexane phase, then be the NaCl aqueous solution washing normal hexane phase of 0.5% by isopyknic mass concentration, last concentrating under reduced pressure.
In above-mentioned steps four, adopt silica gel column chromatography separating purification, adopt normal hexane wet method dress post, adopt normal hexane: acetone: the volume ratio isocratic elution of methyl alcohol=92.5:7:0.5, and detect by tlc, collect the elutriant consistent with β-cryptoxanthin standard substance.
In above-mentioned steps six, crystallization cleans crystal with normal hexane after going out Stigmasterol crystal, until crystal is colourless; Again solution is carried out concentrate drying, finally select ether-methanol to carry out crystallization to dried material, obtain β-cryptoxanthin crystal, and use washed with methanol crystal, till washed with methanol liquid is colourless.
In above-mentioned steps four, the condition of thin-layer chromatography is: developping agent is sherwood oil: ether=7:3, and developer is 10% sulfuric acid-dehydrated alcohol, 95 DEG C of baking 2min.
Beneficial effect: the method adopting a kind of separated in synchronization and purifying β-cryptoxanthin and Stigmasterol from peel of Citrus reticulata Blanco of the present invention, β-cryptoxanthin and Stigmasterol can be extracted from peel of Citrus reticulata Blanco, method simple practical, good separating effect simultaneously, separated product purity is high, is applicable to suitability for industrialized production.
Accompanying drawing explanation
Fig. 1 is the schema that the present invention obtains;
Fig. 2 is the infrared spectrogram of the Stigmasterol that the present invention obtains;
Fig. 3 is the Stigmasterol that obtains of the present invention
1h-NMR spectrogram;
Fig. 4 is the Stigmasterol that obtains of the present invention
13c-NMR spectrogram;
Fig. 5 is β-cryptoxanthin of obtaining of the present invention
1h-NMR spectrogram;
Fig. 6 is the high-efficient liquid phase chromatogram of β-cryptoxanthin standard substance;
Fig. 7 is the high-efficient liquid phase chromatogram of β-cryptoxanthin that the present invention obtains;
The Photomicrograph of β-cryptoxanthin that Fig. 8 the present invention obtains;
The Photomicrograph of the Stigmasterol that Fig. 9 the present invention obtains.
Embodiment
Below in conjunction with embodiment, the invention will be further described.
A method for separated in synchronization purifying β-cryptoxanthin and Stigmasterol from peel of Citrus reticulata Blanco, comprises the following steps:
Step one, by peel of Citrus reticulata Blanco dry and abrasive dust under the temperature condition of 40 DEG C;
Step 2, in the water-bath of 38 ~ 45 DEG C, with the pretreated raw material of dehydrated alcohol lixiviate 2 times, united extraction liquid, concentrating under reduced pressure obtains total ester extract;
Step 3, first described total ester extract is dissolved in normal hexane is extracted thing solution, the mass concentration of this extract solution is 0.046 ~ 0.056%, in extract solution, add KOH-ethanolic soln again carry out saponification reaction, the mass concentration of this KOH-ethanolic soln is 8 ~ 12%, the volume ratio of described extract solution and KOH-ethanolic soln is 1:1, and saponification time is 12h; After saponification reaction completes, add isopyknic normal hexane and extract, be separated and obtain normal hexane phase, then be the NaCl aqueous solution washing normal hexane phase of 0.5% by isopyknic mass concentration, last concentrating under reduced pressure.
Step 4, employing silica gel column chromatography separating purification, adopt normal hexane wet method dress post, adopt normal hexane: acetone: the volume ratio isocratic elution of methyl alcohol=92.5:7:0.5, and detect by tlc, with β-cryptoxanthin standard substance for contrast, collect the main elutriant containing β-cryptoxanthin standard substance and Stigmasterol;
The condition of described thin-layer chromatography is: developping agent is sherwood oil: ether=7:3, and developer is 10% sulfuric acid-dehydrated alcohol, 95 DEG C of baking 2min.
Step 5, first normal hexane-acetone is selected to carry out Double solvent method crystallization to the enriched material of described elutriant, wherein acetone is the good solvent of Stigmasterol, and normal hexane is the poor solvent of Stigmasterol, and under 25 DEG C of conditions, crystallization goes out Stigmasterol crystal, crystal is cleaned, until crystal is colourless with normal hexane;
Again solution is carried out concentrate drying, ether-methanol is finally selected to carry out crystallization to dried material, wherein ether is the good solvent of β-cryptoxanthin crystal, methyl alcohol is the poor solvent of β-cryptoxanthin, under 25 DEG C of conditions, crystallization obtains β-cryptoxanthin crystal, and use washed with methanol crystal, the purity of its β-cryptoxanthin reaches 98.48%.
The qualification of crystallized product:
One, the Infrared spectroscopy of white crystals
Fig. 2 is Stigmasterol crystal infrared spectrogram, analyzes: 3500-3200cm to Fig. 2
-1locating wide and strong bands of a spectrum is absorption bands that O-H stretching vibration causes, and it is key character bands of a spectrum of fatty alcohol.2870 and 2949 is the stretching vibration peak of the C-H of methyl, and 1448 and 1373 is the C-H formation vibration absorption peak of methylene radical.The weak peak that 1651 place's intensity are lower is the stretching vibration absorption peak of C=C double bond, and 1060 weak peaks, place are the stretching vibration absorption peak of C-O key, and it is steroidal compounds that these diffuse reflectance infrared spectroscopy peaks above embody this compound.
Two, crystallized product nuclear magnetic spectrum is analyzed
Above β-cryptoxanthin crystal and Stigmasterol crystal carried out nmr analysis, and result is as shown in Fig. 3 to Fig. 5, and wherein Fig. 3 is above Stigmasterol
1h-NMR spectrogram, Fig. 4 is above Stigmasterol
13c-NMR spectrogram, Fig. 5 is above β-cryptoxanthin
1h-NMR spectrogram.
Fig. 3 is analyzed:
1h-NMR (400MHz, CDCl
3) have 6 methyl signals peaks in spectrum, be 0.69 (d, J=7.3Hz, 3H) respectively; 0.74 – 0.93 (m, 9H); 0.93-1.01 (m, 6H).Be the trans alkene hydrogen signal in 22 and 23 double bonds at 5.02 (dd, J=15.2,8.6Hz, 1H) and 5.15 (dd, J=15.2,8.6Hz, 1H); The olefinic carbon hydrogen signal that 5.35 (dt, J=4.8,1.9Hz, 1H) are C-6; Company's oxygen carbon signal 3.51 (m, 1H);
Fig. 4 is analyzed:
13c-NMR (125MHz, CDCl
3) spectrum provide 29 carbon signals altogether.δ 140.79, δ 138.32, δ 129.33, δ 121.72 (C-5, C-22, C-23, C-6) four olefinic carbon signals, wherein δ 140.79 (C-5) is quaternary carbon signal; It is the fignal center of 2 quaternary carbons at δ 42.34 (C-13), δ 36.54 (C-10) place; Be a carbon signal be connected with oxygen at the fignal center at δ 71.82 (C-3) place, all the other carbon signals are the carbon signal of alkyl, and the content described in existing document is inferred, this sterol material is probably Stigmasterol.
Fig. 5 is analyzed:
1h-NMR (400MHz, CDCl
3) have 10 methyl signals peaks in spectrum, be 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 ').In addition, 4.02 (m, 1H) are O-H alcoholic extract hydroxyl group fignal center; 1.0-2.0 is alkane=CH-architecture signals peak; 2.0-3.0 be alkene-CH=CH2 fignal center; 6.0-7.0 is aromatic hydrocarbons CH2-C=fignal center.This result and the content described in document basically identical.
Known to the analysis of Fig. 2, Fig. 3, Fig. 4 and Fig. 5, can the product that obtains of preliminary judgement the present invention be β-cryptoxanthin and Stigmasterol.
Three, crystallized product thin-layer chromatographic analysis
Above β-cryptoxanthin crystal and Stigmasterol crystal are carried out thin-layer chromatographic analysis, and adopts β-cryptoxanthin standard substance and the contrast of Stigmasterol standard substance.Thin-layer chromatography condition: developping agent is sherwood oil: ether=7:3, developer is 10% sulfuric acid-dehydrated alcohol, 95 DEG C of baking 2min.Measure the R of each group
fvalue, the results are shown in Table 1:
The R of table 1, crystallized product and standard substance
fvalue
As can be seen from Table 1, the R of above crystal and corresponding standard substance
fbe worth equal, on the basis that above nuclear magnetic spectrum is analyzed, can judge that product that the present invention obtains is very likely as β-cryptoxanthin and Stigmasterol.And after heating colour developing, β-cryptoxanthin is dark blue-green, Stigmasterol is red-purple, consistent with associated description.
Four, efficient liquid phase chromatographic analysis
Efficient liquid phase chromatographic analysis is carried out to β-cryptoxanthin standard substance and β-cryptoxanthin crystallization; High-efficient liquid phase chromatogram condition is: mobile phase A is ethyl acetate, and Mobile phase B is the acetonitrile of 90%, A:B=40:60, isocratic elution; Flow velocity is 1mL/min; Column temperature is 30 DEG C.Fig. 6 and Fig. 7 is respectively the high-efficient liquid phase chromatogram of β-cryptoxanthin standard substance and β-cryptoxanthin crystallization.Comparison diagram 6 and Fig. 7 known, the appearance time of the β that the present invention obtains-cryptoxanthin crystallization is 14.073min, be consistent with β-cryptoxanthin standard substance appearance time 14.050min, namely differentiate from high performance liquid chromatography, the β that the present invention obtains-cryptoxanthin crystallization is β-cryptoxanthin.
Five, crystalline mi morphological analysis
Fig. 8 and Fig. 9 is respectively the Photomicrograph of product of the present invention β-cryptoxanthin and Stigmasterol, and as can be seen from Figure 7, β-cryptoxanthin in the form of sheets, has metalluster; Stigmasterol is mainly needle crystal, and this result is consistent with bibliographical information.
In sum, adopt method of the present invention, energy is abstraction and purification β-cryptoxanthin and Stigmasterol from peel of Citrus reticulata Blanco simultaneously.
Finally it should be noted that; foregoing description is only the preferred embodiments of the present invention; those of ordinary skill in the art is under enlightenment of the present invention; under the prerequisite without prejudice to present inventive concept and claim; can make like multiple types and representing, such conversion all falls within protection scope of the present invention.
Claims (7)
1. the method for separated in synchronization and purifying β-cryptoxanthin and Stigmasterol from peel of Citrus reticulata Blanco, is characterized in that comprising the following steps:
Step one, by peel of Citrus reticulata Blanco dry and abrasive dust;
Step 2, the pretreated raw material of use dehydrated alcohol lixiviate, concentrating under reduced pressure obtains total ester extract;
Step 3, first total for step 2 gained ester extract is dissolved in normal hexane is extracted thing solution, then in extract solution, add KOH-ethanolic soln carry out saponification reaction, extract after saponification reaction completes, finally washing concentrating under reduced pressure;
Step 4, the separation and purification of employing chromatography, with β-cryptoxanthin standard substance for contrast, collect the elutriant simultaneously containing sterol and β-cryptoxanthin;
Step 5, the elutriant obtained in step 4 to be concentrated, obtain enriched material;
Step 6, first the enriched material of normal hexane-acetone to step 5 gained elutriant is selected to carry out Double solvent method crystallization, crystallization goes out Stigmasterol crystal, again the washing lotion after above-mentioned removal Stigmasterol crystal is concentrated, obtain mainly containing the enriched material of β-cryptoxanthin, finally select ether-methanol to carry out crystallization, crystallization goes out β-cryptoxanthin crystal.
2. the method for a kind of separated in synchronization purifying β-cryptoxanthin and Stigmasterol from peel of Citrus reticulata Blanco according to claim 1, is characterized in that: in described step 2, under the condition of 38 ~ 45 DEG C, carries out lixiviate to citrus peel meal.
3. the method for a kind of separated in synchronization purifying β-cryptoxanthin and Stigmasterol from peel of Citrus reticulata Blanco according to claim 1 and 2, it is characterized in that: in described step 3, the mass concentration of described extract solution is 0.046 ~ 0.056%, the mass concentration of described KOH-ethanolic soln is 8 ~ 12%, the volume ratio of described extract solution and KOH-ethanolic soln is 1:1, and saponification time is 12h.
4. the method for a kind of separated in synchronization purifying β-cryptoxanthin and Stigmasterol from peel of Citrus reticulata Blanco according to claim 3, it is characterized in that: in described step 3, after saponification reaction completes, add isopyknic normal hexane to extract, separation obtains normal hexane phase, be the NaCl aqueous solution washing normal hexane phase of 0.5% again by isopyknic mass concentration, last concentrating under reduced pressure.
5. the method for a kind of separated in synchronization purifying β-cryptoxanthin and Stigmasterol from peel of Citrus reticulata Blanco according to claim 1, it is characterized in that: in described step 4, adopt silica gel column chromatography separating purification, adopt normal hexane wet method dress post, adopt normal hexane: acetone: the volume ratio isocratic elution of methyl alcohol=92.5:7:0.5, and detect by tlc, collect the elutriant consistent with β-cryptoxanthin standard substance.
6. the method for a kind of separated in synchronization purifying β-cryptoxanthin and Stigmasterol from peel of Citrus reticulata Blanco according to claim 1 or 2 or 5, it is characterized in that: in described step 6, crystallization cleans crystal with normal hexane after going out Stigmasterol crystal, until crystal is colourless; Again washing lotion is carried out concentrate drying, finally select ether-methanol to carry out crystallization to dried material, obtain β-cryptoxanthin crystal, and use washed with methanol crystal, till the methyl alcohol for cleaning is colourless.
7. the method for a kind of separated in synchronization purifying β-cryptoxanthin and Stigmasterol from peel of Citrus reticulata Blanco according to claim 5, it is characterized in that the condition of thin-layer chromatography in step 4 is: developping agent is sherwood oil: ether=7:3, developer is 10% sulfuric acid-dehydrated alcohol, 95 DEG C of baking 2min.
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| CN106380501A (en) * | 2016-08-09 | 2017-02-08 | 右江民族医学院 | Method for extracting stigmasterol from coix stems |
| 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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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106380501A (en) * | 2016-08-09 | 2017-02-08 | 右江民族医学院 | Method for extracting stigmasterol from coix stems |
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| 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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