CN109438548A - A kind of preparation method of paris polyphylla pennogenin Pb - Google Patents
A kind of preparation method of paris polyphylla pennogenin Pb Download PDFInfo
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- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
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Abstract
The invention discloses the quickly and efficiently preparation methods of paris polyphylla pennogenin Pb a kind of.This method includes that three steps such as ethyl alcohol extraction, macroporous resin enrichment total saposins and column chromatography for separation obtain pennogenin Pb in paris polyphyllas, obtains 95% or more the purity of chonglou saponin Pb.This method, as extractant, is extracted abundant using ethyl alcohol；Macroporous resin enrichment total saposins are complete；By silicagel column and YMC pillar, single pennogenin Pb is effectively obtained.The Extraction solvent small toxicity that this method uses, simple process is feasible, and low in cost, operating procedure is simple, is easy to amplify, is very suitable to large-scale production.
Description
Technical field
The invention belongs to the extractive technique fields of vegetable active composition, and in particular to one kind extracts separation from Paris polyphylla medicinal material
The method of pennogenin Pb prepares paris polyphylla using macroporous resin enrichment and column chromatography combination rapidly extracting more particularly to a kind of
The method of pennogenin Pb.
Background technique
Paris polyphylla is the herbaceos perennial of Trilliaceae (Triliaceae) Paris (paris L.), and the whole world is shared
27 kinds, China has 25 kinds, wherein there is 19 kinds to be distributed in Southwestern China area, is mostly used as medicine with rhizome, is in the common tradition in China
Medicine is recorded by version over the years " Chinese Pharmacopoeia ", and it is paris polyphylla Paris that " Chinese Pharmacopoeia " version in 2015, which records Paris polyphylla kind,
Polyphylla Smith Var.chinensis (Franch.) Hara and Yunnan Rhizoma Paridis Paris polyphylla Smith
The dry rhizome of var.yunnanensis (Franch.) Hand.-Mazz..Paris polyphylla, bitter, cold nature, return liver warp have small
Poison, has swelling and pain relieving, and clearing heat and detoxicating, dispelling wind and relieving convulsion and other effects can be used for traumatic injury, abscess of throat, venomous snake bite, infantile convulsion
The diseases such as twitch.
Steroid saponin compound is mainly contained in Paris polyphylla medicinal material, over one hundred is had reported at present, according to structure type master
It is divided into inclined promise steroid saponin (pennogenin saponins) and Chinese yam steroid saponin (diosgenin saponins), with
And C-22 lactone steroid saponin, pregnane saponin(e (pregnane saponins) and furostan type steroid saponin
(furostanolsaponins) etc., most of steroid saponins have stronger pharmacology and physiological activity, have antitumor, only
Blood, anti-inflammatory, analgesia, calmness, inhibits angiogenesis, immunological regulation, anti-oxidant, protection liver and kidney and other effects at antibacterial, clinical
Aspect chonglou saponin is widely used in treating the treatment of the various diseases such as tumour, urinary system infection contamination and gynecologic blood diseases.
In recent years, many scholars go deep into the pharmacological activity of chonglou saponin and clinical application and widely study, and are
Broader prospect is opened up in the comprehensive exploitation and utilization of chonglou saponin.But since Paris polyphylla production of crude drugs year limit for length and Paris polyphylla resource subtract
It is few, affect the comprehensive exploitation and utilization of chonglou saponin.
Pennogenin Pb is one of principle active component of chonglou saponin and Paris polyphylla medicinal material and the preparation matter of medicinal material containing Paris polyphylla
One of the effective component mainly controlled is measured, there is preferable styptic activity, gynecologic blood diseases are had a better effect.
Separation, the preparation of pennogenin Pb mostlys come from the separation of Paris polyphylla medicinal material chemical component and identification.It mainly adopts at present
It is obtained using chloroform, methanol or acetonitrile equal solvent as eluant, eluent finally by multiple methanol crystallization with half preparation method, gained is most
Easily there are the organic solvent residuals such as methanol in finished product.In addition, since chloroform and acetonitrile solvent toxicity are all bigger, it is volatile, it is long
Time use is also bigger to human injury, and environmental pollution limits its a large amount of use industrially also than more serious,
It is only applicable to a small amount of pennogenin Pb sample preparation at present, is not suitable for large-scale production, prepares pennogenin Pb.
Summary of the invention
The present invention provides a kind of quickly preparation paris polyphylla pennogenin Pb on the basis of studying paris polyphylla effective component
New process.Using paris polyphylla as raw material, ethyl alcohol extracted, is designed to provide and a kind of extracts separation pennogenin Pb from paris polyphylla
Method, with solve organic solvent toxicity used when the existing separation from paris polyphylla medicinal material prepares pennogenin Pb it is big, to environment
It is seriously polluted, can not large-scale production technical problem.
In order to realize above-mentioned purpose of the invention, the present invention provides the following technical solutions:
A kind of preparation method of paris polyphylla pennogenin Pb, this method include ethyl alcohol extraction, macroporous resin enrichment total saposins,
Column chromatography for separation step.
According to a kind of method for extracting separation pennogenin Pb from paris polyphylla, specifically includes the following steps:
It (1) is coarse powder by the paris polyphylla pulverizing medicinal materials after drying, addition weight is 2 times of 1 ~ of paris polyphylla medicinal material weight, volume
The ethyl alcohol that percentage concentration is 80%, refluxing extraction 2~3 times, 1~3h, Extracting temperature are 85 DEG C of 80 ~ every time, and extracting solution passes through
Then filter, combined extract are concentrated in vacuo into 5% ~ of alcohol content, 10% solution, filter, obtain filtrate.
It (2) is first 20 times of 10 ~ of Paris polyphylla medicinal material weight with weight, pure water is washed by the upper macroporous resin column of filtrate obtained above
It is de-, discard eluent；It is again 10 times of 5 ~ of Paris polyphylla medicinal material weight with weight, the ethanol elution that concentration expressed in percentage by volume is 85% will
85% ethanol eluate merges, and is concentrated to get the crude extract of chonglou saponin Pb is rich in.
(3) 100 ~, the 200 mesh silica gel mixed sample for being 2.0 times of 1.5 ~ of crude extract by crude extract obtained above and weight
Afterwards, upper 200 ~, 300 mesh silicagel column carries out silica gel column chromatography, and using ethyl acetate: ethyl alcohol=6:1 is eluted, will be containing inclined
The eluent of promise saponin(e Pb ingredient merges, and recycling design is done to close, obtains pennogenin Pb crude product.
(4) methanol that the pennogenin Pb crude product concentration expressed in percentage by volume obtained is 60% dissolves, then upper YMC column, first
It is eluted with 60% methanol, discards eluent, then eluted with 70% methanol, collect eluent, it is dense to steam 50 DEG C of decompressions of instrument using rotation
It is reduced to close dry.
(5) solid that concentration is spin-dried for is washed with a small amount of methanol 3 times, and gained sediment fraction vacuum oven is dried, and is done
Dry temperature is 40-50 DEG C, and drying time is the chonglou saponin Pb that 2-4h is greater than 98% to get content.
Compared with prior art, the advantages and benefits of the present invention are:
(1) 80% ethyl alcohol thermal extraction is used, is extracted more abundant.
(2) macroporous resin enrichment total saposins are used, simple process is more suitable for scale.
(3) silicagel column separates saponin(e in conjunction with YMC column, avoids introducing using the toxic solvents such as chloroform and acetonitrile.
(4) when the present invention extracts separation paris polyphylla pennogenin Pb used Extraction solvent be ethyl alcohol, ethyl acetate and
Water, small toxicity, simple process is feasible, be suitable for industrialized production, and solvent for use easily recycle, can Reusability, to environment
Less pollution, resulting pennogenin Pb sterling are that the research and development of next step drug and application are laid a good foundation.
Detailed description of the invention
Fig. 1 is the mass spectrogram of chonglou saponin Pb；
Fig. 2 is the hydrogen spectrogram of chonglou saponin Pb；
Fig. 3 is the carbon spectrogram of chonglou saponin Pb.
Specific embodiment
Below in conjunction with the drawings and specific embodiments, the invention will be further elaborated, so as to those skilled in the art
The present invention is known more about, but the present invention is not limited with this.
The instrument arrived used in following embodiments and reagent are as follows:
Instrument: BRUKER AV-500M type Nuclear Magnetic Resonance (Germany, Brooker)；Agilent G6230 flight time liquid matter
Combined instrument (Anjelen Sci. & Tech. Inc).
Reagent and reagent: paris polyphylla medicinal material (place of production: Lijing Yun Xin green bio development corporation, Ltd.)；Ethyl alcohol, methanol, second
Acetoacetic ester is to analyze pure (The Titan Corp.)；Water is ultrapure water；Macroreticular resin D-101 (Tianjin sea light Chemical Co., Ltd.)；
YMC reverse phase silica gel filled column (50 μm, Japanese YMC Co., Ltd.).
Embodiment 1
The method for extracting separation pennogenin Pb from paris polyphylla, specifically includes the following steps:
It (1) is coarse powder (1.0kg) by dry paris polyphylla pulverizing medicinal materials, addition weight is 2 times of 1 ~ of paris polyphylla medicinal material weight
(about 2L), the ethyl alcohol that concentration expressed in percentage by volume is 80%, refluxing extraction 2~3 times, 1~3h, Extracting temperature are 80-85 DEG C every time,
Extracting solution is through filtering, combined extract, is then concentrated in vacuo into 5% ~ of alcohol content, 10% solution, and filtration obtains filtrate.
(2) filtrate obtained above is upper large pore resin absorption column (3kg, column internal diameter 8.5cm), it is first Paris polyphylla with weight
20 times of 15 ~ of medicinal material weight (about 20L), pure water elution discard eluent；It is again 20 times of 10 ~ of paris polyphylla medicinal material weight with weight,
The ethanol elution that concentration expressed in percentage by volume is 85% merges 85% ethanol eluate, and concentration claims to get inclined promise total saposins are arrived
Weight is 15g.
It (3) is 100 ~, 200 mesh of 1.0-1.5 times of crude extract (about 22g) by crude extract obtained above and weight
After silica gel mixed sample, upper 200 ~, 300 mesh silicagel column (0.5kg；Column internal diameter is 4cm), silica gel column chromatography is carried out, using ethyl acetate:
Ethyl alcohol=6:1 is eluted, eluting agent about 4L, will be merged containing the eluent of chonglou saponin Pb ingredient, recycling design is extremely
It is close dry, obtain pennogenin Pb crude product, weight 4.4g, purity about 18-25%.
(4) pennogenin Pb crude product obtained above is mixed into sample with YMC, then upper YMC column (column internal diameter 26mm, height
460mm), it is first eluted with 60% methanol 1L, discards eluent, then eluted with 70% methanol 1L, collect eluent, steamed using rotation
50 DEG C of instrument are concentrated under reduced pressure into close dry, obtain pennogenin Pb.
(5) above-mentioned acquisition solid is washed 3 times, each 5ml with methanol, at the drying of gained sediment fraction vacuum oven
Reason, drying temperature are 40 DEG C, and drying time is the chonglou saponin Pb, yield 0.88g that 4h is greater than 95% to get content.
Embodiment 2
The method for extracting separation chonglou saponin Pb from paris polyphylla, specifically includes the following steps:
It (1) is coarse powder (10kg) by dry paris polyphylla pulverizing medicinal materials, it is 4-6 times of weight of paris polyphylla medicinal material that weight, which is added,
(about 50L), the ethyl alcohol that concentration expressed in percentage by volume is 80%, refluxing extraction 2~3 times, 1~3h, Extracting temperature are 80-85 DEG C every time,
Extracting solution is through filtering, combined extract, is then concentrated in vacuo into 5% ~ of alcohol content, 10% solution, and filtration obtains filtrate.
(2) filtrate obtained above is upper large pore resin absorption column (30kg, column internal diameter 27cm), it is first Yunnan weight with weight
20 times of 15 ~ of building medicinal material weight (about 200L), pure water elution discard eluent；It is again 10 ~ 20 of paris polyphylla medicinal material weight with weight
Times, the ethanol elution that concentration expressed in percentage by volume is 85% merges 85% ethanol eluate, it is concentrated to get inclined promise total saposins are arrived,
It is weighed as 152g.
It (3) is 100 ~, 200 mesh of 1.0-1.5 times of crude extract (about 220g) by crude extract obtained above and weight
After silica gel mixed sample, upper 200 ~, 300 mesh silicagel column (8kg；Column internal diameter is 8.5cm), silica gel column chromatography is carried out, using ethyl acetate:
Ethyl alcohol=6:1 is eluted, eluting agent about 40L, will be merged containing the eluent of chonglou saponin Pb ingredient, recycling design is extremely
It is close dry, obtain pennogenin Pb crude product, weight 42g, about 18 ~ 25% of purity.
(4) pennogenin Pb crude product obtained above is mixed into sample with YMC, then upper YMC column (678g；Column internal diameter is 49mm,
High 460mm), it is first eluted with 60% methanol 15L, discards eluent, then eluted with 70% methanol 15L, eluent is collected, using rotation
Turn 50 DEG C of steaming instrument and be concentrated under reduced pressure into close dry, obtains pennogenin Pb.
(5) above-mentioned acquisition solid is washed 3 times, each 100ml with methanol, at the drying of gained sediment fraction vacuum oven
Reason, drying temperature are 40 DEG C, and drying time is the chonglou saponin Pb, yield 8.5g that 4h is greater than 95% to get content.
The Structural Identification of chonglou saponin Pb is detailed in Fig. 1 to Fig. 3:
Chonglou saponin Pb, white crystals (methanol), molecular formula C45H72O17, CAS registration number: 55916-52-4；
ESI-MSm/z:907 [M+Na]+。1H-NMR (CD3OD, 500MHz) δ: 0.71 (3H, d, J=5.5Hz, CH3-27), 097
(3H, s, CH3-18), 1.09 (3H, s, CH3-19), 1.25 (3H, d, J=7.1Hz, CH3-21), 1.77 (3H, d, J=
6.1Hz, CH3-Rha), 4.83 (1H, d, J=5.8Hz, Glc-H-1), 5.37 (1H, s, Rha-H-l), 5.38 (1H, s,
Rha-H-1), 5.12 (1H, brs, H-6).13C-NMR (CD3OD, 125MHz) δ: 37.2 (C-1), 30.7 (C-2),
78.3 (C-3), 38.8 (C-4), 141.2 (C-5), 122.2 (C-6), 32.3 (C-7), 32.0 (C-8) .50.0 (C-
9), 36.9 (C-10), 20.9 (C-11), 31.9 (C-12), 44.8 (C-13), 52.6 (C-14), 31.0 (C-15),
90.3 (C-16), 90.7 (C-17), 17.4 (C-18), 19.8 (C-19), 43.9 (C-20), 9.6 (C-21), 110.8
(C-22), 31.9 (C-23), 28.7 (C-24), 30.3 (C-25), 66.7 (C-26), 17.7 (C-27), Glc:100.1
(C-1 '), 77.3 (C-2 '), 77.4 (C-3 '), 76.6 (C-4 '), 76.9 (C-5 '), 62.0 (C-6 '), Rha:101.9
(C-1 "), 72.4 (C-2 "), 73.0 (C-3 "), 74.0 (C-4 "), 70.0 (C-5 "), 19.2 (C-6 "), Rha:111.0
(C-1 " '), 83.2 (C-2 " '), 78.2 (C-3 " '), 86.6 (C-4 " '), 62.3 (C-5 " ').Its NMR data and document
[southeast Hua Dong, Liu Yang, Wang Xiayin, Lu Yunyang, Li Hui, Tang Haifeng wide leaf Paris polyphylla chemical constitution study [J] pharmacy, 2015,13
(1): 43-46. the data in] are almost the same.
Claims (2)
1. a kind of preparation method of paris polyphylla pennogenin Pb, it is characterised in that this method includes ethyl alcohol extraction, macroreticular resin richness
Collect total saposins, column chromatography for separation step.
2. a kind of preparation method of paris polyphylla pennogenin Pb as described in claim 1, it is characterised in that under this method includes
State step:
(1) dry paris polyphylla medicinal material is taken, is crushed as coarse powder, addition weight is 1~2 times of paris polyphylla medicinal material weight, volume basis
The ethyl alcohol that concentration is 80%, refluxing extraction 2~3 times, 1~3h, Extracting temperature are 80~85 DEG C every time, and extracting solution is filtered, and is closed
And extracting solution, it is then concentrated in vacuo into 5%~10% solution of alcohol content, filters, obtains filtrate；
It (2) is first 10~20 times of paris polyphylla medicinal material weight with weight, pure water is washed by the upper macroporous resin column of filtrate obtained above
It is de-, discard eluent；It is again 5~10 times of paris polyphylla medicinal material weight with weight, the ethanol elution that concentration expressed in percentage by volume is 85% will
85% ethanol eluate merges, and concentration obtains the crude extract rich in chonglou saponin Pb；
(3) after 100~200 mesh silica gel mixed samples for being 1~2 times of crude extract by crude extract obtained above and weight, upper 200
~300 mesh silicagel columns carry out silica gel column chromatography, and using ethyl acetate: ethyl alcohol=6:1 is eluted, and will contain chonglou saponin Pb
The eluent of ingredient merges, and recycling design is done to close, obtains chonglou saponin Pb crude product；
(4) 60% methanol of pennogenin Pb crude product obtained above is dissolved, then upper YMC column, is first eluted with 60% methanol,
Eluent is discarded, then is eluted with 70% methanol, eluent is collected, is concentrated under reduced pressure into using 50 DEG C of instrument of rotation steaming close dry；
(5) precipitating obtained above is washed 3 times with methanol, gained sediment fraction vacuum oven is dried, drying temperature
It is 40-50 DEG C, drying time 2-4h obtains the pennogenin Pb that content is greater than 95%.
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