CN107496490B - A kind of Herba Epimedii rhodiola rosea formulated product and preparation method thereof - Google Patents
A kind of Herba Epimedii rhodiola rosea formulated product and preparation method thereof Download PDFInfo
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- CN107496490B CN107496490B CN201710893479.XA CN201710893479A CN107496490B CN 107496490 B CN107496490 B CN 107496490B CN 201710893479 A CN201710893479 A CN 201710893479A CN 107496490 B CN107496490 B CN 107496490B
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- 238000007796 conventional method Methods 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 238000001976 enzyme digestion Methods 0.000 description 1
- 239000000469 ethanolic extract Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002213 flavones Chemical class 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000010031 fufang xuelian Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000003163 gonadal steroid hormone Substances 0.000 description 1
- 230000011132 hemopoiesis Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 230000002584 immunomodulator Effects 0.000 description 1
- 229940121354 immunomodulator Drugs 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- HUOOMAOYXQFIDQ-UHFFFAOYSA-N isoginkgetin Chemical compound C1=CC(OC)=CC=C1C1=CC(=O)C2=C(O)C=C(O)C(C=3C(=CC=C(C=3)C=3OC4=CC(O)=CC(O)=C4C(=O)C=3)OC)=C2O1 HUOOMAOYXQFIDQ-UHFFFAOYSA-N 0.000 description 1
- CGPVRBMMGYBFAC-UHFFFAOYSA-N isoginkgetin Natural products COc1ccc(cc1)C2=COc3c(C2=O)c(O)cc(O)c3c4cc(ccc4OC)C5=CC(=O)c6c(O)cc(O)cc6O5 CGPVRBMMGYBFAC-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000008777 kaempferol Nutrition 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 150000002617 leukotrienes Chemical class 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 229940043353 maltol Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 238000001471 micro-filtration Methods 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- UXOUKMQIEVGVLY-UHFFFAOYSA-N morin Natural products OC1=CC(O)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UXOUKMQIEVGVLY-UHFFFAOYSA-N 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 150000003833 nucleoside derivatives Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229940100691 oral capsule Drugs 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 230000000242 pagocytic effect Effects 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 235000005875 quercetin Nutrition 0.000 description 1
- 229960001285 quercetin Drugs 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 210000004927 skin cell Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
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Abstract
One kind is disclosed from plant extract glycoside substance method, and the composition comprising Shorthorned Epimedium P.E and gadol extract, the extract has particularly good antiphlogistic effects compared with general extraction mixture.The composition, which can be used for preparing, can enhance immune function of human body, radiation protection and anti-inflammatory drug, health products or drink.
Description
Technical field
The present invention relates to extractive technique fields, more particularly to extract glycoside object from Herba Epimedii using multistage column chromatography for separation
Matter method, and be related to including the composition of Shorthorned Epimedium P.E and rhodiola root derivative.
Background technology
Herba Epimedii is traditional traditional tonic medicine in China, is initially recorded in《Sheng Nong's herbal classic》On, with tonifying kidney and strengthening yang, by force
The effect of muscle reinforcing and bone strengthening, remove rheumatism.Epimedium herb is the dried leaf of Berberidaceae plant Herba Epimedii, and existing pharmacopeia is included shared
The kinds such as Epimedium sagittatum, E. Pubescens and korean epimedium herb are more.Herba Epimedii has the work(of kidney-replenishing, strengthening the bones and muscles, wind-damp dispelling
Effect.Icariin is one of monomer ingredient, and having improves cardiovascular system, adjusts endocrine, strengthen immunity, sex hormone sample
The effects that, while also having positive therapeutic effect in antitumor, anti-liver poison etc..
Modern pharmacological studies have shown that Herba Epimedii can increase cardiovascular and cerebrovascular blood flow, promote hematopoiesis function, immune function and bone
Metabolism has anti-aging, antitumor and other effects.
Recent researches find, the monomeric substances such as glycoside substance, Flavonoid substances and polysaccharose substance in Herba Epimedii,
Improve blood vessel inner skin cell function and be better than tradition processing Herba Epimedii Chinese medicine especially, however their separation and Extraction has very big difficulty.
CN101264120B discloses a kind of barrenwort flavonol glycosides medicine materical crude slice, is made of Herba Epimedii effective part extract,
Icariin content is 10-20%wt, and icariside I I contents are 2-5%wt, general flavone content 40-60%wt, total Huang
Ketone includes icariside I I, newly determine towards leaves of pulse plants glycosides 1, towards the leaves of pulse plants K, icariin, towards leaves of pulse plants glycosides I, towards leaves of pulse plants glycosides third, towards leaves of pulse plants glycosides A, newly towards the leaves of pulse plants
The preparation method of glycosides 2 and Hyperoside, barrenwort flavonol glycosides medicine materical crude slice includes:Weigh the korean epimedium herb overground part after crushing
Point, with ethanol water refluxing extraction;Extracting solution filtering is concentrated under reduced pressure after merging, then is diluted with ethanol water, after standing from
The heart, upper Diaion-HP20 resin columns are collected 60-70%v ethanol waters and elute liquid, subtracted with ethanol water gradient elution
Pressure is concentrated into paste, and crushed after being dried obtains barrenwort flavonol glycosides medicine materical crude slice.
CN101843629A discloses the new application of icariin and the epimedium flavone containing icariin, and in particular to
The extract prepare for treat, prevent, mitigate and/or alleviate disease related with nervous system myelin disease damage and/or
Purposes in the drug of illness, or preparing for the purposes in mitigating myelinoclasis and/or promoting the drug of myelin reparation.
CN104711300A discloses a kind of preparation method of icariine, and this method includes by Shorthorned Epimedium P.E in fruit
Carry out enzyme digestion reaction under the action of glue enzyme, obtain icariine, it is preferable that the pectase include polygalacturonase and
Arabinofuranosidase.
CN101933550A discloses the electuary containing Herba Epimedii, and the electuary is by Herba Epimedii, ground coffee, cordyceps sinensis or pupa
Cordyceps sinensis is constituted, and the weight percent of each material is as follows:Herba Epimedii and the sum of cordyceps sinensis or Cordyceps militaris account for 2-99%, ground coffee 1-
98% or Herba Epimedii 1-95%, cordyceps sinensis or Cordyceps militaris 1-96%, ground coffee 1-98%.
CN104171175A discloses a kind of Herba Epimedii tea, is prepared in following manner:A, acquisition is selected:Every year
Spring acquires Epimedium brevicornum leaves, chooses sundries and old leaf;B, it finishes:It finishes 1-3 minutes at 160 DEG C~200 DEG C;C, it rubs:It will
Epimedium brevicornum leaves after water-removing are rubbed, and are rubbed at item;D, fried dry:It will rub to Epimedium brevicornum leaves in stripes at 130 DEG C -90 DEG C
Carry out fried dry, first through 130 DEG C of fryings of high temperature, fry to it is half-dried when gradually descend temperature regulating to 110 DEG C, gradually descend temperature adjustment again through frying
Degree is to 90 DEG C, until fried dry.
CN101607976A discloses a kind of preparation method of icariin, takes epimedium herb, with the methanol of 30-90%
Or alcohol reflux extraction, recycling design are condensed into medicinal extract;It is extracted repeatedly with petroleum ether, chloroform, ethyl acetate and n-butanol successively
To close colourless, recycling n-butanol obtains coarse extract to dry;Then silica gel column chromatography separation and polyamide column chromatography point are carried out successively
From to get icariin highly finished product, purity >=98%.
CN104688795A discloses a kind of method preparing general flavone by Herba Epimedii, and this approach includes the following steps:a.
Herba Epimedii cured leaf is extracted by ethanol solution first, obtains extracting solution;B. extracting solution macropore step a obtained
Resin column adsorbs, and then uses the macroporous resin column described in water and ethanol elution successively, collects last time ethanol eluate;C. will
The eluent drying that step b is obtained, obtains the general flavone.
CN101669980B discloses a kind of method for extracting separating icariin and general flavone from Herba Epimedii, including with
Lower step:It is first extracted using 20-40% ethyl alcohol as solvent counter current, extracting solution centrifuges, and separating liquid is respectively with microfiltration membranes except heavy
Filtering and Ultra filtration membrane, then with nanofiltration membrane treatment, obtain trapped fluid;This trapped fluid is dried, 60 DEG C of drying temperature is hereinafter, dry
Object moisture content≤5.0%, dried object are epimedium active constituent enriched substance, and wherein Icariin content reaches 60% or more, excessive
Sheep leaves of pulse plants general flavone content reaches 80% or more, UF membrane each unit icariin, the epimedium flavone rate of transform >=98%.
CN101899077A discloses the extracting method of icariside I in Korean epimedium leaves, and step and condition are such as
Under:A. the volumetric concentration that Korean epimedium leaves use is 15 times of its quality is 70% alcohol reflux 4 hours, filters out ethyl alcohol extraction
Liquid is filtered by the dregs of a decoction to flow back with being that the volumetric concentration of 10 times of korean epimedium herb leaf quality is extracted 2 hours for 70% alcohol reflux
Go out ethanol extract, merges filtrate twice;B. filtrate is depressurized at 50 DEG C and steams solvent, obtains extract, contained in extract
Moisture be not more than the 5% of its quality;C. it uses obtained in the absolute ethyl alcohol dissolving step b of 2 times of korean epimedium herb leaf quality
Concentrated hydrochloric acid is added, korean epimedium herb leaf quality gram in extract: the volume mL of concentrated hydrochloric acid is 1:0.05~0.15, in 50 DEG C of water-baths
Heating 15-25 hours, left at room temperature over night, filtering;D filtrates are concentrated under reduced pressure into the 20% of its volume at 50 DEG C, and it is excessive that Korea is added
Precipitation is precipitated in the distilled water of 2 times of sheep leaves of pulse plants leaf quality, is deposited in the ethanol solution for being 20% with volumetric concentration at 50 DEG C and washs, washes
Being deposited at 50 DEG C after washing is dried in vacuo, and obtains icariside I powder.
CN105998140A discloses a kind of rhodiola root composition, is grouped as by following group:1.5-6g of rhodiola root, thorn
Slender acanthopanax 3-27g, Radix Angelicae Sinensis 2-12g.
CN102487979B discloses a kind of Rhodiola rosea micro-powder lotus seed paste, and it includes lotus seeds 50- to constitute by weight percentage
70%, Siraitia grosvenorii 5-15%, vegetable oil 10-20%, Radix Rhodiolae micropowder 7-15%;The Radix Rhodiolae micropowder is rhodiola root ultra micro
The micro mist that grain size made of pulverizer is 0.1-10 μm.
CN103012512A discloses a kind of isolation and purification method of rhodioloside in natural rhodiola root, takes natural rhodiola root
It is sliced for raw material, obtains Aqueous extracts through ultrasonic water leaching, low temperature alcohol precipitation and after being concentrated under reduced pressure, then removed through solvent
Removal of impurities, solvent extraction and back extraction stage obtain the rhodioloside aqueous solution of high-purity, most afterwards through reduced pressure, absolute ethyl alcohol knot
Crystalline substance detaches and is dried to obtain rhodioloside product.
CN101804156A discloses the preparation process and antifatigue effect of compound rhodiola root extractive, by rhodiola root
20g-30g, sealwort 20g-30g, Schisandra chinensis 10g-20g, Herba Epimedii 10g-20g, jujube 3g-5g, what 8-10 times of coarse powder addition was measured
After water impregnates 4h-6h, 100 DEG C of heating extractions, then ultrasound 1h-1.5h, temperature is 30 DEG C, power 80W, then with gauze mistake
Filter, filter residue is each primary with 6 times of amounts and 4 times of amount water repetition above steps respectively again, merges filtrate three times, people is added in vacuum drying
Join three alcohol type saponin(e 0.5g-1g, obtains compound rhodiola root extractive.
" Herba Epimedii Study on extraction ", Chen Luoyi etc., Chinese Journal of Modern Applied Pharmacy, 2000 (s1):12-14, research are excessive
Sheep leaves of pulse plants extraction process selects L9 (3~4) orthogonal test table, knot wherein using Icarrin as Testing index
Fruit shows that decocting method is close with alcohol extracting method extraction effect, and Herba Epimedii uses decocting method, and simple process is at low cost, and extraction efficiency is high,
It is comparatively ideal production technology.
By the above-mentioned prior art it is found that still having number of drawbacks in the prior art, Herba Epimedii extraction in the prior art
Object is actually the mixture of many kinds of substance, wherein including flavones ingredient, more than ten kind leaves of pulse plants glycosides, the leaves of pulse plants time glycosides, a variety of glucosides, the wooden fat
Element, alkaloid and polysaccharide, maltol, the vertical glycosides of sand, Quercetin, icariine A, Epimedium acuminatium glycosides, anhydroicartin, isoamyl
Alkene kaempferol, ginkegetin, Isoginkgetin, bilobetin, epimidin A, Hyperoside also contain certain
Volatile oil, brown eleostearic acid, stearic acid, oleic acid, the leukotrienes of amount.In these substances, effective component is irregular or even some components
Drug effect is relatively low, relatively low to not only result in integral medicinal effect, and since some inefficient ingredients can influence high-drug-effect ingredient instead
The performance of energy.In addition, there exists a further problem in that, Shorthorned Epimedium P.E and gadol extract are mixed although having in the prior art
The report of compound formulation is prepared, but is usually all the extract mixing containing complicated ingredient by two kinds, not only effect is poor, but also
Synergistic effect is also poor.A kind of efficient Herba Epimedii of this field needs and gadol extract and preparation method thereof.
Invention content
To solve the above-mentioned technical problems in the prior art simultaneously, the present invention provides one kind extracting sugar from Herba Epimedii
Glycoside substance method, the glucosides substance has relatively high pharmacological activity compared with other ingredients in extract, special
It is not to improve immunity and anti-inflammatory efficacy.In addition, the composition comprising Shorthorned Epimedium P.E and gadol extract is additionally provided,
It is acted synergistically by the compounding of the two, comprehensive pharmacological activity can be improved.For this purpose, the present invention provides following technical schemes.
In one aspect of the invention, one kind is provided from plant extract glycoside substance method, and this method uses multistage column
Chromatography.
Preferably, wherein the plant is Herba Epimedii.
Preferably, in the multistage column chromatography for separation, first order column chromatography uses reverse phase silica gel column.
Most preferably, the extraction and isolated glucosides substance are lower formula (I) compound represented:
Studies have shown that the glucoside compound has compared with general flavone compound such as icariine A and B
Wider bioactivity, such as anti-osteoporosis disease, androgen, anti-inflammatory and antitumaous effect.Therefore, the application makees the compound
For Objective extraction compound.
For the present invention, particularly preferably, formula (I) compound represented can be made by following method, the party
Method includes the following steps:
(1) MeOH (preferably 3 × 6L, each soaking time are about 20h) extraction Herba Epimedii herbal medicine powder is used at room temperature (preferably
1.18kg), combined extract is evaporated under reduced pressure to obtain brown residue (162.5g) i.e. methanol extract liquid;
(2) reverse phase silica gel column (such as RP-18 silicagel columns) is utilized, uses MeOH-H first2O mixed solutions are to the remnants
Object carries out gradient elution, and to carry out pillar layer separation, preferred elution step is 0:1 (1L), 1:9 (1L), 2:8 (1L), 3:7
(1L), 4:6 (1L), 5:5 (2L), 6:4 (2L), 7:3 (1L), 1:0 (2L) then uses acetone (2L), obtains 10 successively and wash
De- component is denoted as elution component A-J;
(3) elution fraction B (such as 6.5g) is subjected to chromatographic isolation on silicagel column (preferably 60cm × 5cm), used
CHCl3-MeOH-H2O mixed solutions carry out gradient elution, and (gradient is preferably 20:1:0 (1L), 10:1:0 (2L), 30:8:1
(2L) and 15:6:1 (2.5L)), 4 elution components are obtained, elution fraction B1-B4 is denoted as;
(4) elution fraction B2 (such as 300.2mg) is used into MeOH-H2O(1:1) Sephadex LH-20 (preferably
100cm × 3cm) on detach, obtain 7 time elution fractions, be denoted as elution fraction B2.1-B2.7;
(5) by elution fraction B2.6 (such as 95.0mg) by silica gel CC columns (preferably 80cm × 2.5cm), eluent is
EtOAc-CHCl3-MeOH-H2O(16:8:3:1), eluent is concentrated to dryness, obtains pale yellow powder (such as 6.1mg),
As compound shown in formula (I).
It is analyzed through HPLC, the purity of compound shown in formula (I) is 99.7% in extract.Through1HNMR and mass spectral analysis,
It is consistent with the known compound through characterization described in CAS.Positive ion mode ESI-MS shows that molecular ion peak appears in m/
z 667([M+Na]+) and 1311 ([2M+Na]+)。IR(KBr):3423, 2940,1660,1605,1512,1450。1In HNMR,
In the A2B2 coupled systems that δ (H) 7.88 (d, J=8.6, H-C (2 ', 6 ')) and 7.11 (d, J=8.6, H-C (3 ', 5 ')) occur
Show the presence of para-orientating group in B rings;In δ (H) 6.72 (d, J=10.0, H-C (1 "), 5.68 (d, J=10.0, H-C
The serial hydrogen atom signal that (2 "), 2.14 (s, Me (4 ")) and 1.45 (s, Me (5 ")) occur shows that there are γ, γ-dimethyl
Chromene ring.
Experiment finds that it is extremely difficult to obtain compound or extract shown in the formula (I) of high-purity to separation, wherein
A major reason for leading to be difficult to obtain high-purity compound is the interference of albumen in extraction process, in addition, some low liters
Polysaccharide is also the impurity of more difficult separation.The applicant obtains the formula of extreme high purity for the first time by above-mentioned 5 grades of column chromatography for separation
(I) compound shown in.Have close level and matching relationship, setting selection and sequence non-between 5 grades of piece-rate systems
Chang Guanjian.
Certainly, it will be appreciated by those of skill in the art that other elution fractions can also be used to obtain it is other valuable
Substance rather than all discard.
In another aspect of this invention, a kind of composition including Shorthorned Epimedium P.E and gadol extract is provided,
The Shorthorned Epimedium P.E is the glucosides substance obtained according to the above method, preferably compound shown in (I).It can also be at this
Saussurea involucrata extract, wolfberry fruit extract or other extracts with required pharmacological activity are added in composition.
Preferably, the purity of the glucosides substance is more than 99.0wt%.It is highly preferred that the purity of the glucosides substance
More than 99.2wt%.Most preferably, the purity of the glucosides substance is more than 99.7wt%.
The gadol extract is preferably rhodioside.Rhodioside can take the conventional method of this field to be carried
It takes.It is further preferred that the gadol extract is modified gadol extract, most preferably, the gadol extract is logical
It crosses and the lower formula (II) obtained or (III) compound represented is modified to rhodioside:
Compared with general natural nucleoside substance, the immunological regulation of formula (II) or (III) compound represented to normal mouse
Effect becomes apparent from, and due to the introducing of electron-withdrawing group Cl and F, enhances its ability for removing free radical, can dramatically increase mouse
Special antibody secreting cell number can enhance delayed allergy intensity with 50mg/ (kgd) dosage, in addition also show
Go out the phagocytic function of the mixed lymphocyte reaction (MLP) to special-shaped mouse and macrophage, and can reduce to a certain extent white
The activity of cytokine shows that the two is a kind of up-and-coming immunomodulator.
Substance with structure formula (II)~(III) can synthesize by the following method:MCM- is added in the reaction vessel
22 molecular sieves alternatively property catalyst, is then added chloroform solvent, then by the acetyl of natural salidroside and chloro or fluoro
Chlorine (i.e. acylating agent) is with 1:1~1.3 molar ratio is added in reaction dissolvent (natural salidroside and chloro or the acetyl of fluoro
Chlorine is preferably added in the form of chloroformic solution), reaction temperature is 20-30 DEG C, reaction time 10-30min, separation and drying
It can be obtained the compound.This method has the advantages that high income, impurity are few.It is particularly due to the shape-selective of MCM-22 molecular sieves
Effect, can significantly reduce the generation of side reaction.
In another aspect of this invention, the purposes for providing the composition, human immunity work(can be enhanced by being used to prepare
Drug, health products or the drink of energy.
Preferably, the drug is Chinese traditional compound medicine.Preferably, the composition is used to prepare oral capsule, electuary
Deng.The health products include oral-cavity article such as chewable tablets or lozenge.
In a preferred embodiment of the present invention, in the Chinese traditional compound medicine, Shorthorned Epimedium P.E and rhodiola root
The weight ratio of derivative is 1:20-20:1.When Saussurea involucrata extract is added, the weight ratio of Saussurea involucrata extract and Shorthorned Epimedium P.E
It is 1:10-1:20.Such composition has effects that particularly good anti-inflammatory, strengthen immunity and/or radiation protection.
Description of the drawings
Fig. 1 is the compound according to the embodiment of the present application 11HNMR analysis diagrams;
Fig. 2 is the suppression curve figure to PTP1B according to the compound of the embodiment of the present application 1.
Specific implementation mode
Embodiment 1:The extraction of compound shown in formula (I)
Using compound shown in following operation extraction formula (I):(1) MeOH (3 × 6L, each soaking time are used at room temperature
It is about 20h) extraction Herba Epimedii herbal medicine powder (1.18kg, raw material are purchased from the Tonghua, Jilin Province city towns Jin Chang), combined extract is subtracted
Pressure evaporation obtains brown residue (162.5g) i.e. methanol extract liquid;(2) RP-18 reverse phase silica gel columns are utilized, are used first
MeOH-H2O mixed solutions carry out gradient elution to the residue, to carry out pillar layer separation, elution step 0:1 (1L),
1:9 (1L), 2:8 (1L), 3:7 (1L), 4:6 (1L), 5:5 (2L), 6:4 (2L), 7:3 (1L), 1:0 (2L) then uses acetone
(2L) obtains 10 elution fractions successively, is denoted as elution component A-J;(3) by 6.5g elution fractions B silicagel column (60cm ×
Chromatographic isolation is carried out on 5cm), using using CHCl3-MeOH-H2O mixed solutions carry out gradient elution (gradient 20:1:0
(1L), 10:1:0 (2L), 30:8:1 (2L) and 15:6:1 (2.5L)), 4 elution components are obtained, elution fraction B1-B4 is denoted as;
(4) by 300.2mg elution fraction B2 MeOH-H2O(1:1) it detaches, obtains on Sephadex LH-20 (100cm × 3cm)
7 elution fractions, are denoted as elution fraction B2.1-B2.7;(5) 95.0mg elution fractions B2.6 is passed through into silica gel CC columns (80cm
× 2.5cm), eluent EtOAc-CHCl3-MeOH-H2O(16:8:3:1), eluent is concentrated to dryness, obtains 6.1mg
Compound shown in pale yellow powder, as formula (I).
Embodiment 2:Compound shown in formula (I) inhibits PTP 1B (PTP1B) and α-glucuroide
Ability.Specific rejection ability is as shown in table 1 below:
Table 1:Compound shown in formula (I) inhibits the ability of PTP 1B (PTP1B) and alpha-glucosidase
In the test, malol and acarbose are used as positive reference substance.Test method is according to standard method with micro
Method carries out, specifically:This system reaction 100 μ L, PTP1B substrates p-NPP of total volume is dissolved in buffer solution (50mmolL- 1HEPES pH value 7.3,100mmolL-1NaCl, 0.1%BSA, 1mmolL-1DTT in), pNPP reactions are final concentration of
5mmol·L-1, extract dissolves by DMSO, takes 0.5~1 μ L of enzyme solution, diluted and mixed well by 250 μ L PBS buffer solution, taken
The 160 μ L of enzyme solution diluted add to 96 orifice plates, add 1 μ L of DMSO (extract solvent), soft mixing, at the same by PTP1B with
35mmolL is added after 96 orifice plates incubation at room temperature 5min is added in extract-1P-NPP 20 μ L, 37 DEG C are protected from light 30min, and 0.5
mol·L-1Sodium hydroxide terminates reaction, and microplate reader reads absorbance (A) value at wavelength 405nm, and phase is calculated according to normalized form
Answer half-inhibition concentration (IC50) value;Also make suppression curve of the compound to PTP1B simultaneously (referring to Fig. 2).
Embodiment 3:Include the manufacture of the capsule of Shorthorned Epimedium P.E and gadol extract
Including the Shorthorned Epimedium P.E of embodiment 1 and the capsule manufacturing method of gadol extract, wherein the rhodiola root
Extract is compound shown in formula (II), and the weight ratio of Shorthorned Epimedium P.E and rhodiola root derivative is 5:1, each capsule contains
There are 0.1g contents.
Embodiment 4:Anti-inflammatory effect of the capsule of testing example 3 to mice auricle swelling
Kunming mice 40, weight 150-220g is taken, half male and half female is randomly divided into 5 groups, i.e. model group, conventional extract
Capsules group (0.08gkg-1, control group, wherein Shorthorned Epimedium P.E according to described in CN101264120B method obtain,
It is remaining same as Example 3), 3 Capsules group (0.08gkg of embodiment-1), daily gastric infusion 1 time, continuous 4d, in last dose
30min afterwards, every mouse right ear exterior feature two sides are applied 20 μ L of dimethylbenzene, cause mice auricle swelling model, compared with left ear,
Cervical dislocation puts to death mouse after 20min, two ears is cut along auricle baseline, with diameter 6mm card punch respectively in left and right ear antimere
Round auricle is laid, precise weighing using its difference as inflammatory swelling degree (mg), and calculates swelling inhibiting rate.
Swelling inhibiting rate=(model group swelling-administration group swelling)/model group swelling × 100%
Compared with model group mice ear degree, the compound capsule group of embodiment 3 is compared with compareing each dosage group of Capsules group
The significant difference of inhibiting effect of mice ear caused by paraxylene shows to prompt FUFANG XUELIAN JIAONANG that can mitigate diformazan
Benzene causes mice auricle swelling degree, has certain anti-inflammatory effect, see the table below 2:
Table 2:Compound capsule paraxylene causes the influence of mice auricle swelling
Group | Dosage/gkg-1 | Swelling/mg | Inhibiting rate/% |
Model group | - | 8.55±1.22 | - |
Embodiment 3 | 0.08 | 4.01±0.92 | 53.10% |
Control group | 0.08 | 5.96±1.23 | 30.29% |
By above example clearly it can be seen from the present invention Shorthorned Epimedium P.E to PTP1B) and alpha-glucosidase
With good inhibiting effect, and compared with the existing technology in extract (i.e. crude extract, the mixture of Multiple components)
It compares, there is apparent better antiphlogistic effects.
This written description discloses the present invention, including optimal mode using example, and also enables those skilled in the art
It manufactures and using the present invention.The present invention can patentable scope be defined by the claims, and may include this field skill
Other examples that art personnel expect.If this other examples have not different from the structural elements of the literal language of claims
Element, or if this other examples include with equivalent structure element of the literal language of claims without substantial differences,
Then this other examples are intended within the scope of claims.In the case where inconsistent degree will not be caused, by reference to
It will be incorporated herein in place of all references referred to herein.
Claims (5)
1. a kind of extracting glycoside substance method from Herba Epimedii, this method uses multistage column chromatography for separation, the extraction and separation
Obtained glucosides substance is lower formula (I) compound represented:
This approach includes the following steps:
(1) Herba Epimedii herbal medicine powder is extracted with MeOH at room temperature, combined extract is evaporated under reduced pressure to obtain brown residue i.e.
Methanol extract liquid;
(2) reverse phase silica gel column is utilized, uses MeOH-H first2O mixed solutions carry out gradient elution to the residue, to carry out
Pillar layer separation, elution step 0:1 total 1L, 1:9 total 1L, 2:8 total 1L, 3:7 total 1L, 4:6 total 1L, 5:5 total 2L, 6:4 total 2L,
7:3 total 1L, 1:Then 0 total 2L uses acetone 2L, obtains 10 elution fractions successively, be denoted as elution component A-J;
(3) elution fraction B is subjected to chromatographic isolation on a silica gel column, uses CHCl3-MeOH-H2O mixed solutions carry out gradient and wash
It is de-, gradient 20:1:0 total 1L, 10:1:0 total 2L, 30:8:1 total 2L and 15:6:1 total 2.5L obtains 4 elution components,
It is denoted as elution fraction B1-B4;
(4) by elution fraction B2 with 1:1 MeOH-H2O is detached on Sephadex LH-20, obtains 7 elution fractions, note
For elution fraction B2.1-B2.7;
(5) elution fraction B2.6 is passed through into silica gel CC columns, eluent 16:8:3:1 EtOAc-CHCl3-MeOH-H2O will be washed
De- liquid is concentrated to dryness, and obtains pale yellow powder, as compound shown in formula (I).
2. a kind of composition including Shorthorned Epimedium P.E and gadol extract, the Shorthorned Epimedium P.E is to be wanted according to right
The glucosides substance for asking the method described in 1 to obtain, the gadol extract are lower formula (II) compound represented:
3. composition according to claim 2, wherein the purity of the glycoside substance is more than 99.0wt%.
4. composition according to claim 3, wherein the purity of the glycoside substance is more than 99.2wt%.
5. composition according to claim 4, wherein the purity of the glycoside substance is more than 99.7wt%.
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