CN109776631A - A kind of preparation method of acteoside - Google Patents
A kind of preparation method of acteoside Download PDFInfo
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- CN109776631A CN109776631A CN201910093150.4A CN201910093150A CN109776631A CN 109776631 A CN109776631 A CN 109776631A CN 201910093150 A CN201910093150 A CN 201910093150A CN 109776631 A CN109776631 A CN 109776631A
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- acteoside
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- aqueous solution
- reduced pressure
- methanol aqueous
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- QFRYQWYZSQDFOS-UHFFFAOYSA-N verbascoside Natural products CC1OC(COC2C(O)C(COC3OC(C(O)C(O)C3O)C(=O)O)OC(Oc4cc(O)cc5OC(=CC(=O)c45)c6ccc(O)c(O)c6)C2O)C(O)C(O)C1O QFRYQWYZSQDFOS-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 229930185474 acteoside Natural products 0.000 title claims abstract description 50
- FBSKJMQYURKNSU-ZLSOWSIRSA-N acteoside Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](OC(=O)\C=C\C=2C=C(O)C(O)=CC=2)[C@@H](CO)O[C@@H](OCCC=2C=C(O)C(O)=CC=2)[C@@H]1O FBSKJMQYURKNSU-ZLSOWSIRSA-N 0.000 title claims abstract description 50
- FBSKJMQYURKNSU-UKQWSTALSA-N acteoside I Natural products C[C@@H]1O[C@H](O[C@@H]2[C@@H](O)[C@H](OCCc3ccc(O)c(O)c3)O[C@H](CO)[C@H]2OC(=O)C=Cc4ccc(O)c(O)c4)[C@H](O)[C@H](O)[C@H]1O FBSKJMQYURKNSU-UKQWSTALSA-N 0.000 title claims abstract description 50
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- 239000000284 extract Substances 0.000 claims abstract description 19
- 241000404844 Callicarpa nudiflora Species 0.000 claims abstract description 17
- 239000000287 crude extract Substances 0.000 claims abstract description 13
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000000605 extraction Methods 0.000 claims abstract description 12
- 238000010992 reflux Methods 0.000 claims abstract description 9
- 239000011347 resin Substances 0.000 claims abstract description 9
- 229920005989 resin Polymers 0.000 claims abstract description 9
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229930182470 glycoside Natural products 0.000 claims abstract description 5
- FLUADVWHMHPUCG-OVEXVZGPSA-N Verbascose Natural products O(C[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](OC[C@@H]2[C@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]3(CO)[C@H](O)[C@@H](O)[C@@H](CO)O3)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](CO[C@@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@H](CO)O2)O1 FLUADVWHMHPUCG-OVEXVZGPSA-N 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 114
- 239000007864 aqueous solution Substances 0.000 claims description 32
- 239000003480 eluent Substances 0.000 claims description 24
- 239000000243 solution Substances 0.000 claims description 15
- 238000010828 elution Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims 2
- 150000002338 glycosides Chemical class 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- FLUADVWHMHPUCG-SWPIJASHSA-N verbascose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO[C@@H]3[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO[C@@H]4[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O4)O)O3)O)O2)O)O1 FLUADVWHMHPUCG-SWPIJASHSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- -1 verbascose glycoside Chemical class 0.000 abstract description 3
- 241000196324 Embryophyta Species 0.000 abstract description 2
- 241001529246 Platymiscium Species 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 description 10
- 239000000725 suspension Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 4
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 3
- 241000336291 Cistanche deserticola Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- KDSWDGKIENPKLB-QJDQKFITSA-N verbascoside Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](OC(=O)CCC=2C=C(O)C(O)=CC=2)[C@@H](CO)O[C@@H](OCCC=2C=C(O)C(O)=CC=2)[C@@H]1O KDSWDGKIENPKLB-QJDQKFITSA-N 0.000 description 2
- QIMGUQIHCNDUKU-UHFFFAOYSA-N 2-[[6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-methyloxane-3,4,5-triol Chemical compound OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OCCC=2C=C(O)C(O)=CC=2)O1 QIMGUQIHCNDUKU-UHFFFAOYSA-N 0.000 description 1
- 241001337994 Cryptococcus <scale insect> Species 0.000 description 1
- DTOUWTJYUCZJQD-QJDQKFITSA-N Forsythiaside Natural products C[C@@H]1O[C@H](OC[C@H]2O[C@@H](OCCc3ccc(O)c(O)c3)[C@H](O)[C@@H](O)[C@@H]2OC(=O)C=Cc4ccc(O)c(O)c4)[C@H](O)[C@H](O)[C@H]1O DTOUWTJYUCZJQD-QJDQKFITSA-N 0.000 description 1
- 208000009362 Pneumococcal Pneumonia Diseases 0.000 description 1
- 101710183389 Pneumolysin Proteins 0.000 description 1
- 206010035728 Pneumonia pneumococcal Diseases 0.000 description 1
- 241000405414 Rehmannia Species 0.000 description 1
- 240000002657 Thymus vulgaris Species 0.000 description 1
- 235000007303 Thymus vulgaris Nutrition 0.000 description 1
- YMWRMAOPKNYHMZ-LLVTZOIGSA-N [(2r,3r,4r,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-4-[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2-[[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-3-yl] (e)-3-(3,4-dihydroxyphenyl)prop-2-enoate Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC[C@@H]1[C@@H](OC(=O)\C=C\C=2C=C(O)C(O)=CC=2)[C@H](O[C@H]2[C@@H]([C@H](O)[C@@H](O)[C@H](C)O2)O)[C@@H](O)[C@H](OCCC=2C=C(O)C(O)=CC=2)O1 YMWRMAOPKNYHMZ-LLVTZOIGSA-N 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000002155 anti-virotic effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- YDDMELPLARDERH-UHFFFAOYSA-N cistanoside Natural products CC1OC(OC2C(O)C(OCCc3ccc(O)c(OC(=O)C)c3)OC(COC4OC(CO)C(O)C(O)C4O)C2OC(=O)C=Cc5ccc(O)c(O)c5)C(O)C(O)C1O YDDMELPLARDERH-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 229930189432 forsythoside Natural products 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 230000023597 hemostasis Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000004112 neuroprotection Effects 0.000 description 1
- 229930015704 phenylpropanoid Natural products 0.000 description 1
- YMWRMAOPKNYHMZ-FFPRBYOHSA-N poliumoside Natural products C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](OCCc3ccc(O)c(O)c3)O[C@H](CO[C@H]4O[C@H](C)[C@@H](O)[C@H](O)[C@@H]4O)[C@H]2OC(=O)C=Cc5ccc(O)c(O)c5)[C@H](O)[C@H](O)[C@H]1O YMWRMAOPKNYHMZ-FFPRBYOHSA-N 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 230000004224 protection Effects 0.000 description 1
- 208000022218 streptococcal pneumonia Diseases 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000001585 thymus vulgaris Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a kind of preparation methods of acteoside.It is the following steps are included: use ethanol water refluxing extraction after callicarpa nudiflora rhizome is dry, crushing, extracting solution obtains medicinal extract after being concentrated under reduced pressure, medicinal extract obtains acteoside crude extract through macroporous resin column, then obtains acteoside through Sephadex LH-20 gel column separating purification.The present invention makes full use of purple strain platymiscium is callicarpa nudiflora to prepare acteoside, has expanded the plant origin of acteoside；The extraction preparation method of acteoside is optimized, preparation process is simple, and production cost is low, and operation is controllable；The verbascose glycoside product of preparation has the features such as content is high, and quality is stablized.
Description
Technical field:
The invention belongs to field of biology, and in particular to a kind of preparation method of acteoside.
Background technique:
Acteoside (Verbascoside) is also known as acteoside, acteoside, and Verbascoside etc. is a kind of Phenylpropanoid Glycosides
Glycosides compound belongs to natural polyphenol constituents, molecular formula C29H36O15, molecular weight 624.59, structural formula such as formula (I)
It is shown.During it is primarily present in Cistanche deserticola, purple strain category, reach the clouds category and glutinous rehmannia category etc. belong to, modern studies have found that acteoside
With a variety of stronger bioactivity such as anti-bacteria and anti-virus, anti-inflammatory, anti-oxidant, antitumor, neuroprotection.Such as Funari human hair
Existing acteoside has the function of that anti-neogenesis cryptococcus, zhao et al. discovery acteoside can inhibit pneumolysin
The cytotoxicity of mediation eliminates pneumococcal pneumonia symptom.
Biosynthesis and chemical synthesis all difficulty of acteoside are big, are not easy mass production, presently mainly by mentioning
The method for taking separation obtains, and patent mainly extracts separation acteoside from Cistanche deserticola in recent years, and purple strain category is also
The important sources of acteoside.Wherein callicarpa nudiflora is Verenaceae purple strain platymiscium, is distributed mainly on China Guangdong, extensively
West, the ground such as Hainan, medicinal part are ground drying nest, have hemostasis, dissolving stasis, antibacterial anti-inflammatory, analgesia, Thyme Extract.It is main
To contain acteoside, Forsythoside, poliumoside, cistanoside etc..There has been no prepare hair stamen from callicarpa nudiflora at present
The method of flower glucosides.
Summary of the invention:
The purpose of the present invention is overcoming defect in the prior art, a kind of preparation method of acteoside is provided.
The purpose of the invention is achieved by the following technical solution:
A kind of preparation method of acteoside, comprising the following steps: use ethyl alcohol after callicarpa nudiflora rhizome is dry, crushing
Aqueous solution refluxing extraction, extracting solution obtain medicinal extract after being concentrated under reduced pressure, and macroporous resin column are crossed after medicinal extract is dissolved with water, with methanol
Aqueous solution is as mobile phase, from the methanol aqueous solution linear gradient elution of volume fraction 10%-100%, collected volume score
The eluent that the methanol aqueous solution of 20%-50% elutes, eluent obtain acteoside crude extract after being concentrated under reduced pressure,
Sephadex LH-20 gel column is crossed after acteoside crude extract is dissolved with methanol, using methanol aqueous solution as mobile phase,
From the methanol aqueous solution linear gradient elution of volume fraction 10%-100%, the methanol of collected volume score 30%-70% is water-soluble
The eluent that liquid elutes, eluent obtain acteoside after being concentrated under reduced pressure.
The ethanol water is preferably the ethanol water of volume fraction 50%-80%.
The usage amount of the ethanol water is preferably 8-25 times of dry callicarpa nudiflora rhizome quality.
The Extracting temperature of the refluxing extraction is preferably 70 DEG C -100 DEG C, and extraction time is preferably 0.5-3h.
The pressure that the extracting solution obtains the reduced pressure in medicinal extract after being concentrated under reduced pressure is preferably 7-10kPa, temperature
Preferably 50 DEG C -60 DEG C.
The macroporous resin column is preferably D101 macroporous resin column.
Effect innovative point of the invention:
Acteoside rule of origin of the present invention belongs to callicarpa nudiflora plant in purple strain, has expanded acteoside
Plant origin.
Acteoside product preparation process of the present invention is simple, and production cost is low, and operation is controllable.
Verbascose glycoside product of the present invention has the features such as content is high, and quality is stablized.
Specific embodiment:
To facilitate a better understanding of the present invention, it is illustrated by the following examples.These examples belong to protection of the invention
Range, but do not limit the scope of the invention.
A kind of embodiment 1: preparation method 1 of acteoside
A kind of preparation method of acteoside, comprising the following steps:
A) it takes callicarpa nudiflora rhizome dry, is processed into powdered, 10 times of callicarpa nudiflora rhizome quality dry of body is added
The ethanol water of fraction 60% carries out refluxing extraction 1h at 80 DEG C, and filtrate is obtained by filtration in extracting solution；It extracts 2 times repeatedly,
Collect extracting solution, merging filtrate.
B) combined filtrate is carried out on a rotary evaporator being concentrated under reduced pressure to give medicinal extract, the pressure of reduced pressure is
10kPa, temperature are 60 DEG C.
C) medicinal extract is dissolved with water, is allowed into suspension, after D101 macroporous resin column, using methanol aqueous solution as flowing
Phase, from the methanol aqueous solution linear gradient elution of volume fraction 10%-100%, the methanol-water of collected volume score 30%-40%
The eluent that solution elutes, eluent obtain acteoside crude extract after being concentrated under reduced pressure.
D) acteoside crude extract is dissolved with methanol, is allowed into suspension, after Sephadex LH-20 gel column,
Using methanol aqueous solution as mobile phase, from the methanol aqueous solution linear gradient elution of volume fraction 10%-100%, collected volume
The eluent that the methanol aqueous solution of score 50%-60% elutes, it is pure that eluent obtains acteoside after being concentrated under reduced pressure
Product.
A kind of embodiment 2: preparation method 2 of acteoside
A kind of preparation method of acteoside, comprising the following steps:
A) it takes callicarpa nudiflora rhizome dry, is processed into powdered, 8 times of callicarpa nudiflora rhizome quality dry of volume is added
The ethanol water of score 80% carries out refluxing extraction 2h at 70 DEG C, and filtrate is obtained by filtration in extracting solution.
B) filtrate is carried out on a rotary evaporator being concentrated under reduced pressure to give medicinal extract, the pressure of reduced pressure is 7kPa, temperature
It is 50 DEG C.
C) medicinal extract is dissolved with water, is allowed into suspension, after D101 macroporous resin column, using methanol aqueous solution as flowing
Phase, from the methanol aqueous solution linear gradient elution of volume fraction 10%-100%, the methanol-water of collected volume score 40%-50%
The eluent that solution elutes, eluent obtain acteoside crude extract after being concentrated under reduced pressure.
D) acteoside crude extract is dissolved with methanol, is allowed into suspension, after Sephadex LH-20 gel column,
Using methanol aqueous solution as mobile phase, from the methanol aqueous solution linear gradient elution of volume fraction 10%-100%, collected volume
The eluent that the methanol aqueous solution of score 60%-70% elutes, it is pure that eluent obtains acteoside after being concentrated under reduced pressure
Product.
A kind of embodiment 3: preparation method 3 of acteoside
A kind of preparation method of acteoside, comprising the following steps:
A) it takes callicarpa nudiflora rhizome dry, is processed into powdered, 15 times of callicarpa nudiflora rhizome quality dry of body is added
The ethanol water of fraction 50% carries out refluxing extraction 0.5h at 100 DEG C, and filtrate is obtained by filtration in extracting solution；3 are extracted repeatedly
It is secondary, collect extracting solution, merging filtrate.
B) combined filtrate is carried out on a rotary evaporator being concentrated under reduced pressure to give medicinal extract, the pressure of reduced pressure is
8kPa, temperature are 55 DEG C.
C) medicinal extract is dissolved with water, is allowed into suspension, after D101 macroporous resin column, using methanol aqueous solution as flowing
Phase, from the methanol aqueous solution linear gradient elution of volume fraction 10%-100%, the methanol-water of collected volume score 20%-30%
The eluent that solution elutes, eluent obtain acteoside crude extract after being concentrated under reduced pressure.
D) acteoside crude extract is dissolved with methanol, is allowed into suspension, after Sephadex LH-20 gel column,
Using methanol aqueous solution as mobile phase, from the methanol aqueous solution linear gradient elution of volume fraction 10%-100%, collected volume
The eluent that the methanol aqueous solution of score 30%-40% elutes, it is pure that eluent obtains acteoside after being concentrated under reduced pressure
Product.
A kind of embodiment 4: preparation method 4 of acteoside
A kind of preparation method of acteoside, comprising the following steps:
A) it takes callicarpa nudiflora rhizome dry, is processed into powdered, 25 times of callicarpa nudiflora rhizome quality dry of body is added
The ethanol water of fraction 70% carries out refluxing extraction 3h at 90 DEG C, and filtrate is obtained by filtration in extracting solution.
B) filtrate is carried out on a rotary evaporator being concentrated under reduced pressure to give medicinal extract, the pressure of reduced pressure is 10kPa, temperature
It is 60 DEG C.
C) medicinal extract is dissolved with water, is allowed into suspension, after D101 macroporous resin column, using methanol aqueous solution as flowing
Phase, from the methanol aqueous solution linear gradient elution of volume fraction 10%-100%, the methanol-water of collected volume score 30%-50%
The eluent that solution elutes, eluent obtain acteoside crude extract after being concentrated under reduced pressure.
D) acteoside crude extract is dissolved with methanol, is allowed into suspension, after Sephadex LH-20 gel column,
Using methanol aqueous solution as mobile phase, from the methanol aqueous solution linear gradient elution of volume fraction 10%-100%, collected volume
The eluent that the methanol aqueous solution of score 50%-70% elutes, it is pure that eluent obtains acteoside after being concentrated under reduced pressure
Product.
Claims (6)
1. a kind of preparation method of acteoside, which comprises the following steps: the dry, powder by callicarpa nudiflora rhizome
Ethanol water refluxing extraction is used after broken, extracting solution obtains medicinal extract after being concentrated under reduced pressure, and macropore tree is crossed after medicinal extract is dissolved with water
Rouge column, from the methanol aqueous solution linear gradient elution of volume fraction 10%-100%, is collected using methanol aqueous solution as mobile phase
The eluent that the methanol aqueous solution of volume fraction 20%-50% elutes, eluent obtain verbascose after being concentrated under reduced pressure
Glycosides crude extract is crossed Sephadex LH-20 gel column, is made with methanol aqueous solution after dissolving acteoside crude extract with methanol
For mobile phase, from the methanol aqueous solution linear gradient elution of volume fraction 10%-100%, collected volume score 30%-70%'s
The eluent that methanol aqueous solution elutes, eluent obtain acteoside after being concentrated under reduced pressure.
2. preparation method according to claim 1, which is characterized in that the ethanol water is volume fraction 50%-
80% ethanol water.
3. preparation method according to claim 1 or 2, which is characterized in that the usage amount of the ethanol water is dry
8-25 times of dry callicarpa nudiflora rhizome quality.
4. preparation method according to claim 1 or 2, which is characterized in that the Extracting temperature of the refluxing extraction is 70
DEG C -100 DEG C, extraction time 0.5-3h.
5. preparation method according to claim 1 or 2, which is characterized in that the extracting solution obtains after being concentrated under reduced pressure
The pressure of reduced pressure in medicinal extract is 7-10kPa, and temperature is 50 DEG C -60 DEG C.
6. preparation method according to claim 1 or 2, which is characterized in that the macroporous resin column is D101 macropore tree
Rouge column.
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| CN116925166A (en) * | 2023-08-16 | 2023-10-24 | 右江民族医学院 | Method for extracting effective active ingredients of buddleja officinalis and application thereof |
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Application publication date: 20190521 |