CN104725441A - Method for simultaneously separating and preparing syringin and oleuropein from syringa oblata Lindl - Google Patents

Method for simultaneously separating and preparing syringin and oleuropein from syringa oblata Lindl Download PDF

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Publication number
CN104725441A
CN104725441A CN201510136231.XA CN201510136231A CN104725441A CN 104725441 A CN104725441 A CN 104725441A CN 201510136231 A CN201510136231 A CN 201510136231A CN 104725441 A CN104725441 A CN 104725441A
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Prior art keywords
oleuropein
syringin
syringa oblata
oblata lindl
ethyl acetate
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刘香萍
韩玉静
李国良
曲善民
罗英花
杨智明
杨伟光
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Heilongjiang Bayi Agricultural University
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Heilongjiang Bayi Agricultural University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/06—Separation; Purification
    • C07H1/08—Separation; Purification from natural products
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a method for simultaneously separating and preparing syringin and oleuropein from syringa oblata Lindl. The method comprises the following steps: by taking branchlets of syringa oblata Lindl as raw materials, extracting by virtue of a homogenate technique and adsorbing by virtue of a macroporous resin column; carrying out gradient elution by virtue of ethanol solutions with different concentrations; then, respectively carrying out chromatography and separation by using a silica gel column; and recrystalizing to obtain syringing crystals and oleuropein crystals. The method disclosed by the invention comprises the following processes such as extraction of syringin and oleuropein, separation by virtue of macroporous resin and a silica gel column and the like, and has the advantages of being low in cost of raw materials and simple in process, and both solvents and resin can be recovered and the like. The purities of both products are greater than 95%, so that the method is suitable for industrial production on a large scale.

Description

A kind of simultaneously separation from Syringa oblata Lindl. prepares the method for Syringin and Oleuropein
Technical field
The present invention relates to field of natural product chemistry, be specifically related to a kind of simultaneously separation from Syringa oblata Lindl. and prepare the method for Syringin and Oleuropein.
Background technology
Syringin, Oleuropein all have many-sided pharmacologically active, thus have medical applications prospect widely.
Syringin has another name called Syringin, and being one of the primary medicinal component of Radix Et Caulis Acanthopanacis Senticosi, is a kind of anti-liver cytotoxic drug by force.Current Syringin is mainly derived from Radix Et Caulis Acanthopanacis Senticosi, and Radix Et Caulis Acanthopanacis Senticosi is state three level protecting plant, and its processing and utilization is subject to strict restriction.There are some researches show, the content of Syringin in Syringa oblata Lindl. is more than 2 times of Radix Et Caulis Acanthopanacis Senticosi; Oleuropein is mainly separated from leaf of Fructus oleae europaeae.Fructus oleae europaeae is mainly distributed in mediterranean country, though China introduces a fine variety in recent years, stock number is very limited, so it is significant to carry out trial prepared by Oleuropein from other plant resource.Therefore utilize the present invention separating syringin, Oleuropein from Syringa oblata Lindl., not only raw material sources are extensive, and can make full use of gardens pruning the Syringa oblata Lindl. branch discarded, for the field such as pharmacy industry and makeup provides high-quality feedstocks.
At present, the correlative study of rapid extraction separating high-purity Syringin and Oleuropein two compositions simultaneously from Syringa oblata Lindl. is not yet had.
Publication number is that the Chinese patent of CN101643484 discloses a kind of high-purity syringin, preparation method and application, it, by dissolving Radix Et Caulis Acanthopanacis Senticosi cream, macroporous adsorption resin chromatography, decolouring, macroporous adsorption resin chromatography, crystallization, recrystallization, obtains highly purified Syringin.Its step is numerous and diverse, and twice chromatographic enrichment, once decolours, and twice crystallization not only increases the cost of sorbent material, also increase the production cycle, add extraction cost.
Publication number is the extraction and separation method that the Chinese patent of CN101328198 discloses a kind of Syringin, Sparrow Faeces (Syringa oblata Lindl.var.alba Hort.ex Rehd.) branch is pulverized by the method, decocting method is utilized to extract Syringin from Sparrow Faeces, by Syringin extracting solution XDA-1 or AB-8 macroporous adsorptive resins with 20% ~ 60% ethanolic soln wash-out, recycle silicon plastic column chromatography is separated, the Syringin crystal of obtained purity more than 97%.The method crushing process and decoction process carry out respectively, and power consumption increases, and decoct 2 ~ 3 times, 1 ~ 3h consuming time at every turn, and the production cycle is long, and production cost increases.
Publication number is a kind of method that the Chinese patent of CN101307079 discloses extraction and isolation Syringin from Ilex rotunda Thunb., pulverizing medicinal materials is become fine powder by it, use benzene refluxing extraction, the dregs of a decoction after extracting are dried, add acetone refluxing extraction again, merging filtrate, concentrated extracting solution, leave standstill, adularescent powder is separated out, and filters after precipitation completely, use washing with acetone precipitate, by the mixing solutions of precipitate acetone-methanol recrystallization repeatedly, finally use recrystallizing methanol again, the white needles of Syringin can be obtained.The method repeatedly uses the contour toxic organic solvent of benzene, acetone, will produce environmental pollution and the harm such as producers are poisoning.
Publication number is the preparation method that the Chinese patent of CN101003557 discloses the olive leaf extract being rich in high purity Oleuropein, it adopts dissimilar repeatedly film separation coupling technique and media adsorbs coupling technique to replace conventional solvent extraction process, is separated the olive leaf extract being rich in Oleuropein obtaining content and be greater than 50%.But the method gained Oleuropein content is lower, have impact on it and applies further.
Summary of the invention
For solving the problem, the invention provides a kind of simultaneously separation from Syringa oblata Lindl. and preparing the method for Syringin and Oleuropein, to widen the extraction raw material of Syringin, Oleuropein, for pharmacy industry and Management of Cosmetics Enterprises provide high-purity raw.
For achieving the above object, the technical scheme that the present invention takes is:
From Syringa oblata Lindl., be separated the method preparing Syringin and Oleuropein simultaneously, comprise the steps:
S1, prescind to 1 ~ 2cm by the Syringa oblata Lindl. sprig of drying, adding 10 ~ 20 times amount concentration is that 30 ~ 60% ethanolic soln homogenate are extracted 2 ~ 3 times, each homogenate 5 ~ 10min, filters, concentrating under reduced pressure reclaims ethanol, obtain extracting solution after being merged by the solution extracted;
S2, by the extracting solution macroporous resin column of step S1 gained with 2 ~ 3BV/h flow velocity absorption after, with concentration be 15% ~ 25% ethanol 4 ~ 6BV and concentration be 35 ~ 45% ethanolic soln 6 ~ 8BV carry out gradient elution, the Syringin of absorption, Oleuropein can be eluted respectively; Merge the ethanol eluate of same concentrations, concentrating under reduced pressure postlyophilization obtains Syringin crude product, Oleuropein crude product respectively;
S3, by silica gel column chromatography in the Syringin crude product dry method of step S2 gained, carry out wash-out with ethyl acetate, methyl alcohol, water mixed liquid as eluent, collect elutriant, by recrystallizing methanol 2 ~ 3 times after concentrated, obtain the Syringin crystal that purity is greater than 97%;
S4, by silica gel column chromatography in the Oleuropein crude product dry method of step S2 gained, wash-out is carried out as eluent with ethyl acetate, methyl alcohol, water mixed liquid, collect elutriant, leave standstill after concentrated, separate out Oleuropein crystallization, with dehydrated alcohol recrystallization 2 ~ 3 times, obtain the Oleuropein crystal that purity is greater than 95%.
Preferably, in described step S2, the flow velocity of wash-out is 2 ~ 4BV/h.
Preferably, described macroporous resin is the one in D101, HPD-100B or HPD400A.
Preferably, the ratio 12: 1: 0.2 of ethyl acetate, methyl alcohol, water in described step S3, S4.
Preferably, in described step S3, S4, the ratio of ethyl acetate, methyl alcohol, water is 16: 1: 0.2.
The present invention has following beneficial effect:
Open Syringin, Oleuropein prepares new way, its production technique is simple, agents useful for same and resin recoverable, and energy consumption is low, is applicable to suitability for industrialized production; Product yield is high, and purity is high, and wherein, the purity of Syringin is greater than 95%, and the purity of Oleuropein is greater than 97%.
Accompanying drawing explanation
Fig. 1 is the Syringin liquid chromatogram in embodiment of the present invention macroporous resin column elutriant.
Fig. 2 is the Oleuropein liquid chromatogram in embodiment of the present invention macroporous resin column elutriant.
Fig. 3 is gained Syringin liquid chromatogram after the separation and purification of embodiment of the present invention silica gel.
Fig. 4 is gained Oleuropein liquid chromatogram after the separation and purification of embodiment of the present invention silica gel.
Embodiment
In order to make objects and advantages of the present invention clearly understand, below in conjunction with embodiment, the present invention is further elaborated.Should be appreciated that specific embodiment described herein only in order to explain the present invention, be not intended to limit the present invention.
Embodiments provide a kind of simultaneously separation from Syringa oblata Lindl. and prepare the method for Syringin and Oleuropein, comprise the steps:
S1, prescind to 1 ~ 2cm by the Syringa oblata Lindl. sprig of drying, adding 10 ~ 20 times amount concentration is that 30 ~ 60% ethanolic soln homogenate are extracted 2 ~ 3 times, each homogenate 5 ~ 10min, filters, concentrating under reduced pressure reclaims ethanol, obtain extracting solution after being merged by the solution extracted;
S2, by the extracting solution macroporous resin column of step S1 gained with 2 ~ 3BV/h flow velocity absorption after, with concentration be 15% ~ 25% ethanol 4 ~ 6BV and concentration be 35 ~ 45% ethanolic soln 6 ~ 8BV carry out gradient elution, the Syringin of absorption, Oleuropein can be eluted respectively; Merge the ethanol eluate of same concentrations, concentrating under reduced pressure postlyophilization obtains Syringin crude product, Oleuropein crude product respectively; Fig. 1 is the Syringin liquid chromatogram in macroporous resin column elutriant; Fig. 2 is the Oleuropein liquid chromatogram in macroporous resin column elutriant, and wherein, X-coordinate is retention time, and ordinate zou is signal response value.
S3, by silica gel column chromatography in the Syringin crude product dry method of step S2 gained, carry out wash-out with ethyl acetate, methyl alcohol, water mixed liquid as eluent, collect elutriant, by recrystallizing methanol 2 ~ 3 times after concentrated, obtain the Syringin crystal that purity is greater than 97%; Fig. 3 is gained Syringin liquid chromatogram after silica gel separation and purification.
S4, by silica gel column chromatography in the Oleuropein crude product dry method of step S2 gained, wash-out is carried out as eluent with ethyl acetate, methyl alcohol, water mixed liquid, collect elutriant, leave standstill after concentrated, separate out Oleuropein crystallization, with dehydrated alcohol recrystallization 2 ~ 3 times, obtain the Oleuropein crystal that purity is greater than 95%, Fig. 4 is gained Oleuropein liquid chromatogram after silica gel separation and purification.
In described step S2, the flow velocity of wash-out is 2 ~ 4BV/h.Described macroporous resin be D101,
One in HPD-100B or HPD400A.
Embodiment 1
Prepared by S11, extracting solution
Get Syringa oblata Lindl. (Syringa oblata Lindl.) sprig 1kg, extract 3 times, each 10min, solid-liquid ratio 1: 10 (kg/L) after pulverizing with 40% ethanolic soln homogenate, extracting solution merges filtration, is concentrated into 4L.
S12, macroporous resin are separated
Concentrated rear extracting solution HPD-100B macroporous resin column adsorbed with the flow velocity of 3BV/h, then be the ethanolic soln priority wash-out successively of 20% and 40% by volumetric concentration, Fractional Collections elutriant, adopts thin-layer chromatography silica gel precoated plate (HSGF 254) fast qualitative detection.
S13, by concentrated for the elutriant collecting 20% aqueous ethanolic solution obtained, dry Syringin crude product, stirs rear dry method loading after acetic acid ethyl dissolution with a small amount of silica gel and cross silicagel column.Silicagel column is with ethyl acetate: methyl alcohol: water volume ratio 12: 1: 0.2 carries out wash-out, collects elutriant, crystallization after concentrated, with dehydrated alcohol recrystallization 1 time, obtains Syringin crystal 2.71g.Detecting its purity with high performance liquid chromatography is 98.48%.
S14, by concentrated for the elutriant collecting 40% aqueous ethanolic solution obtained, dry Oleuropein crude product, stirs rear dry method loading after acetic acid ethyl dissolution with a small amount of silica gel and cross silicagel column.Silicagel column is with ethyl acetate: methyl alcohol: water volume ratio 16: 1: 0.2 carries out wash-out, collects elutriant, dry after concentrated.Use anhydrous alcohol solution again, crystallization, recrystallization 2 times, obtain Oleuropein crystal 3.26g.Detecting its purity with high performance liquid chromatography is 97.39%.
Embodiment 2
Prepared by S21, extracting solution
Get Syringa oblata Lindl. (Syringa oblata Lindl.) sprig 0.5kg, extract 2 times, each 8min, solid-liquid ratio 1: 20 (kg/L) after pulverizing with 30% ethanolic soln homogenate, extracting solution merges filtration, is concentrated into 2L.
S22, macroporous resin are separated
Concentrated rear extracting solution HPD-400A macroporous resin column adsorbed with the flow velocity of 2BV/h, then be the ethanolic soln priority wash-out successively of 25% and 50% by volumetric concentration, Fractional Collections elutriant, adopts thin-layer chromatography silica gel precoated plate (HSGF 254) fast qualitative detection.
S23, by concentrated for the elutriant collecting 25% aqueous ethanolic solution obtained, dry, after ethyl acetate stirs, dry method loading crosses silicagel column.With ethyl acetate: methyl alcohol: water volume ratio 12: 1: 0.2 carries out wash-out, collect elutriant, crystallization after concentrated, with dehydrated alcohol recrystallization 2 times, obtain Syringin crystal 1.34g.Detecting its purity with high performance liquid chromatography is 95.61%.
S24, by concentrated for the elutriant collecting 50% aqueous ethanolic solution obtained, dry, after ethyl acetate stirs, dry method loading crosses silicagel column.With ethyl acetate: methyl alcohol: water volume ratio 16: 1: 0.2 carries out wash-out, collect elutriant, dry after concentrated.Use anhydrous alcohol solution again, crystallization, recrystallization 2 times, obtain Oleuropein crystal 1.63g.Detecting its purity with high performance liquid chromatography is 98.11%.
Embodiment 3
Prepared by S31, extracting solution
Get Syringa oblata Lindl. (Syringa oblata Lindl.) sprig 0.5kg, extract 3 times, each 6min, solid-liquid ratio 1: 10 (kg/L) after pulverizing with 50% ethanolic soln homogenate, extracting solution merges filtration, is concentrated into 1.5L.
S32, macroporous resin are separated
Concentrated rear extracting solution D101 macroporous resin column adsorbed with the flow velocity of 4BV/h, then be the ethanolic soln priority wash-out successively of 20% and 50% by volumetric concentration, Fractional Collections elutriant, adopts thin-layer chromatography silica gel precoated plate (HSGF 254) fast qualitative detection.
S33, by concentrated for the elutriant collecting 20% aqueous ethanolic solution obtained, dry, after ethyl acetate stirs, dry method loading crosses silicagel column.With ethyl acetate: methyl alcohol: water volume ratio 12: 1: 0.2 carries out wash-out, collect elutriant, crystallization after concentrated, with dehydrated alcohol recrystallization 2 times, obtain Syringin crystal 1.52g.Detecting its purity with high performance liquid chromatography is 96.75%.
S34, by concentrated for the elutriant collecting 50% aqueous ethanolic solution obtained, dry, after ethyl acetate stirs, dry method loading crosses silicagel column.With ethyl acetate: methyl alcohol: water volume ratio 16: 1: 0.2 carries out wash-out, collect elutriant, dry after concentrated.Use anhydrous alcohol solution again, crystallization, recrystallization 3 times, obtain Oleuropein crystal 2.06g.Detecting its purity with high performance liquid chromatography is 98.18%.
The above is only the preferred embodiment of the present invention; it should be pointed out that for those skilled in the art, under the premise without departing from the principles of the invention; can also make some improvements and modifications, these improvements and modifications also should be considered as protection scope of the present invention.

Claims (5)

1. from Syringa oblata Lindl., be separated the method preparing Syringin and Oleuropein simultaneously, it is characterized in that, comprise the steps:
S1, prescind to 1 ~ 2cm by the Syringa oblata Lindl. sprig of drying, adding 10 ~ 20 times amount concentration is that 30 ~ 60% ethanolic soln homogenate are extracted 2 ~ 3 times, each homogenate 5 ~ 10min, filters, concentrating under reduced pressure reclaims ethanol, obtain extracting solution after being merged by the solution extracted;
S2, by the extracting solution macroporous resin column of step S1 gained with 2 ~ 3BV/h flow velocity absorption after, with concentration be 15% ~ 25% ethanol 4 ~ 6BV and concentration be 35 ~ 45% ethanolic soln 6 ~ 8BV carry out gradient elution, merge the ethanol eluate of same concentrations, concentrating under reduced pressure postlyophilization obtains Syringin crude product, Oleuropein crude product respectively;
S3, by silica gel column chromatography in the Syringin crude product dry method of step S2 gained, carry out wash-out with ethyl acetate, methyl alcohol, water mixed liquid as eluent, collect elutriant, by recrystallizing methanol 2 ~ 3 times after concentrated, obtain the Syringin crystal that purity is greater than 97%;
S4, by silica gel column chromatography in the Oleuropein crude product dry method of step S2 gained, wash-out is carried out as eluent with ethyl acetate, methyl alcohol, water mixed liquid, collect elutriant, leave standstill after concentrated, separate out Oleuropein crystallization, with dehydrated alcohol recrystallization 2 ~ 3 times, obtain the Oleuropein crystal that purity is greater than 95%.
2. a kind of simultaneously separation from Syringa oblata Lindl. according to claim 1 prepares the method for Syringin and Oleuropein, and it is characterized in that, in described step S2, the flow velocity of wash-out is 2 ~ 4BV/h.
3. a kind of simultaneously separation from Syringa oblata Lindl. according to claim 1 prepares the method for Syringin and Oleuropein, and it is characterized in that, described macroporous resin is the one in D101, HPD-100B or HPD400A.
4. a kind of simultaneously separation from Syringa oblata Lindl. according to claim 1 prepares the method for Syringin and Oleuropein, it is characterized in that, the ratio 12: 1: 0.2 of ethyl acetate, methyl alcohol, water in described step S3, S4.
5. a kind of simultaneously separation from Syringa oblata Lindl. according to claim 1 prepares the method for Syringin and Oleuropein, and it is characterized in that, in described step S3, S4, the ratio of ethyl acetate, methyl alcohol, water is 16: 1: 0.2.
CN201510136231.XA 2015-03-19 2015-03-19 Method for simultaneously separating and preparing syringin and oleuropein from syringa oblata Lindl Pending CN104725441A (en)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104402949A (en) * 2014-12-12 2015-03-11 黑龙江八一农垦大学 Method for simultaneously separating and preparing syringoside and oleuropein from syringa oblata lindl
CN104693249A (en) * 2015-02-05 2015-06-10 黑龙江八一农垦大学 Method for simultaneously separating and preparing syringin and oleuropein from syringa oblate lindl.

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104402949A (en) * 2014-12-12 2015-03-11 黑龙江八一农垦大学 Method for simultaneously separating and preparing syringoside and oleuropein from syringa oblata lindl
CN104693249A (en) * 2015-02-05 2015-06-10 黑龙江八一农垦大学 Method for simultaneously separating and preparing syringin and oleuropein from syringa oblate lindl.

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
XUEYAN BI，ET AL.: ""Secoiridoid glucosides and related compounds from Syringa reticulate and their antioxidant activities"", 《BIOORGANIC & MEDICINAL CHEMISTRY LETTERS》 *
尉小慧，等: ""RP-HPLC同时测定不同采集地紫丁香树枝中丁香苷和橄榄苦苷的含量"", 《中国药学杂志》 *

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