CN106928289A - One kind is acylated the glucosides of flavones four and its extracting method and application - Google Patents
One kind is acylated the glucosides of flavones four and its extracting method and application Download PDFInfo
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- 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
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
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- 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
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Abstract
The invention provides it is a kind of separated from tealeaves the entitled tea hill for preparing how the glucosides of acylation flavones four of phenose glycosides C;It is first that Lu`an Guapian.Tea tea or yellow big tea powder is broken during preparation;Then Lu`an Guapian.Tea tea or yellow big tea after being crushed with 70 80% acetone floodings obtain leaching liquor, extracted with dichloromethane, ethylacetate step again, extract solution is obtained corresponding extraction position paste extract dichloromethane position, ethyl acetate extract and remaining water position by concentrated under reduced pressure;Water position is isolated and purified using various column chromatography technologies obtain Kaempferol glucosides C again.How the glucosides of acylation flavones four of phenose glycosides C can be applied to lipid-lowering diet drug in the entitled tea hill that the present invention is prepared.
Description
Technical field
The invention belongs to technical field of chemistry, and in particular to a kind of entitled tea hill how the acylation flavones tetrose of phenose glycosides C
Glycosides and its extracting method and application.
Background technology
Tea originates from China, is found and is utilized by our ancestors with its medicinal function, existing away from the present
The history of more than 3000 years, successively experienced the differentiation of the drink from the medicinal whole world to eating to popularizing now.As the fashionable world
Beverage, tealeaves is not only to enjoy consumer's pro-gaze by its unique local flavor, and more crucial factor is by tealeaves institute
The functional component and health-care efficacy for containing.As people are to the pay attention to day by day of health, the healthy functions research of tealeaves also result in
The broad interest of researcher.Research shows that tealeaves has anticancer, anti-oxidant, lowering blood-fat and reducing weight, hypoglycemic, antiallergy, sterilization, disease-resistant
The effects such as poison, protection liver.
Lu`an Guapian.Tea belongs to green tea, originates in the peace of Anhui six, is one of Chinese well-known tea, there is long history inside information
With deep cultural connotation.Most tealeaves all is connected to pluck and processes with bud-leaf, and Lu`an Guapian.Tea is then with list
Piece leaf is processed, while the unique serious skill of drawing in also having drying process concurrently so that it is different from other green tea, together
When it is also popular among consumers.
Huang great Cha belongs to yellow tea class as its name suggests, and the Huang great Cha in Anhui mainly originates in the band of Huoshan one, the spy of Huang great Cha
Select is that leaf is big, stalk is long, yellow yellow stuff, with the dense Gao Huoxiang for splitting, is commonly called as a pot cake perfume (or spice).Yellow big processing raw material with thick old leaf for tea be
Main, vexed Huang is its distinctive manufacturing procedure.There is correlative study to show that Huang great Cha has good effect of lowering blood sugar and hypoglycemic in the recent period
Effect is better than green tea and black tea.
The report of the chemical fundamentals on Lu`an Guapian.Tea and yellow big tea bioactivity is fewer, if can successfully from six peaces
The flavonoid glycoside biotic component with bioactivity is researched and developed in green tea produced in Anhui Province and Huang great Cha, it will to Western Anhui Lu`an Guapian.Tea
And the development and publicity of yellow big tea brand provide certain help, while also important tribute can be made to agricultural and medicine and other fields
Offer.
The content of the invention
An object of the present invention is to provide a kind of entitled tea hill for being separated from Lu`an Guapian.Tea and Huang great Cha and being prepared
How the glucosides of acylation flavones four of phenose glycosides C, this entitled tea hill how the glucosides of acylation flavones four of phenose glycosides C have it is as follows
Structure:
The second object of the present invention be to provide a kind of above-mentioned entitled tea hill how phenose glycosides C acylation the glucosides of flavones four system
Preparation Method, including following two paths:
Path A:
1) raw material is crushed:
Dry Lu`an Guapian.Tea sample tea or Huang great Cha are taken, is crushed powdered;
2) extract
Lu`an Guapian.Tea sample tea or yellow big tea after being crushed with 70-80% acetone flooding obtain leaching liquor, through undue
Level extracts and is concentrated under reduced pressure to give last remaining water position paste;
3) isolate and purify
Water position paste is isolated and purified obtain tea hill how phenose glycosides C.
Preferably, the step 2) in extraction, the Lu`an Guapian.Tea or yellow big after first being crushed with 70-80% acetone flooding
Tea obtains leaching liquor, then is extracted with dichloromethane, ethylacetate step, and extract solution is obtained corresponding extraction position by concentrated under reduced pressure
Paste extract:Dichloromethane position, ethyl acetate extract and remaining water position paste.
Preferably, the step 3) described in isolate and purify be will water position paste dissolve after pass through successively
MCI column chromatographies, silica gel column chromatography, Sephadex LH-20 gel filtration chromatographies, Toyopearl column chromatographic isolation and purifications.
Preferably, the step 3) described in isolate and purify concretely comprise the following steps:By water position paste with water-soluble
MCI posts are crossed after solution uses MeOH-H2O volume ratios 0: 100 to 100: 0 as gradient elution, collects wherein MeOH-H2O volume ratios
70: 30 to 80: 20 elution fraction;Then by the wash-out component of gained through silica gel column chromatography, with CH2Cl2- MeOH volume ratios 20:
1,15: 1,10: 1,5: 1 to 0: 1 used as gradient elution, collects wherein CH2Cl2The elution fraction of-MeOH volume ratios 5: 1;Gained is washed
Again through Sephadex LH-20 gel filtration chromatographies, using MeOH as eluent, collection obtains elution fraction to de- component;Wash-out
Component through Toyopearl column chromatographies, wash-out, obtains Kaempferol glucosides C again.
Path B:
1) raw material is crushed:
Dry Lu`an Guapian.Tea sample tea or Huang great Cha are taken, is crushed powdered;
2) extract
Lu`an Guapian.Tea sample tea or yellow big tea after being crushed with 70-80% acetone flooding obtain leaching liquor, through undue
Level extracts and is concentrated under reduced pressure to give last remaining n-butanol portion paste;
3) isolate and purify
N-butanol portion paste is isolated and purified obtain tea hill how phenose glycosides C.
Preferably, the path step B 2) in extraction, the Lu`an Guapian.Tea after first being crushed with 70-80% acetone flooding
Or yellow big tea obtains leaching liquor, then extracted with dichloromethane, ethylacetate step, extract solution is obtained corresponding extraction by concentrated under reduced pressure
Take position paste extract:Dichloromethane position, ethyl acetate extract and remaining water position, water position extracting n-butyl alcohol,
Finally obtain n-butanol portion paste.
Preferably, the path step B 3) described in isolate and purify be by n-butanol portion paste dissolve after according to
Secondary being isolated and purified through MCI column chromatographies, Sephadex LH-20 gel filtration chromatographies obtains Kaempferol glucosides C.
Preferably, the path step B 3) described in isolate and purify concretely comprise the following steps:
MeOH-H2O volume ratios 20: 80 to 100: 0 are used by MCI column chromatographies are crossed after n-butanol portion paste water dissolves
As gradient elution, the elution fraction of wherein MeOH-H2O volume ratios 70: 30 to 80: 20 is collected;Then by the wash-out group of gained
Through Sephadex LH-20 gel filtration chromatographies, using methyl alcohol as eluent, collection obtains elution fraction to part;Elution fraction is again
Through chromatography, wash-out, Kaempferol glucosides C is obtained.
Preferably, in two kinds of paths of above A, B:The step 2) extraction in, Solvent Extract methods use immersion way
Extract, Lu`an Guapian.Tea or Huang great Cha after will crushing all equally are separately immersed in 70-80 hours in organic solvent;Or by powder
Lu`an Guapian.Tea or Huang great Cha after broken are all equally extracted with organic solvent supersonic oscillations respectively.
The third object of the present invention be by entitled tea hill as described above how the glucosides application of acylation flavones four of phenose glycosides C
Application in terms of lipid-lowering diet drug.
Specifically by tea hill as described above, how phenose glycosides C is acylated the glucosides of flavones four and pharmaceutically general
Auxiliary material is made a kind of lipid-lowering diet drug, and the pharmaceutical dosage form includes oral type, external application type and injection-type.
Beneficial effects of the present invention are as follows:
1) by testing confirmation, how the acylation glucosides of flavones four of phenose glycosides C is in induction in entitled tea hill of the present invention
There is certain lipid accumulation that suppresses to act in 3T3-L1 cells, can apply to prepare lipid-lowering diet drug aspect.Therefore it is of the invention
The flavonoid glycoside compound with medicinal actives for providing, has great importance to agricultural and field of medicaments;
2) while for effective exploitation provides more wide prospect using Lu`an Guapian.Tea and Huang great Cha.
3) preparation method of the present invention is simple, and cost is relatively low.
Brief description of the drawings
Fig. 1 be tea hill how the chemical structural formula of phenose glycosides C.
Fig. 2 is that how the suppression of phenose glycosides C and the other three flavone glycoside to lipid accumulation in 3T3-L1 cells is tested in tea hill
Schematic diagram, wherein 1 be tea hill how phenose glycosides C, 2 be tea hill how phenose glycosides A, 3 is tea quercetin glycoside C, and 4 is tea quercetin glycoside
A。
Specific embodiment
Embodiment of the present invention is described in detail below in conjunction with embodiment, but those skilled in the art will
Understand, the following example is merely to illustrate the present invention, and should not be taken as limiting the scope of the invention.
First, tea hill how the preparation of phenose glycosides C
Embodiment 1:
From the preparation in Lu`an Guapian.Tea
(1) 9.0 kilograms of dry Lu`an Guapian.Tea sample teas are taken, and is crushed powdered;
(2) 9.0 kilograms of dry Lu`an Guapian.Teas are extracted 72 hours with 29 liter of 80% acetone water normal temperature first, Ran Hou
Ultrasound extraction 2 hours under 70Hz;Obtain 80% acetone water position extract solution;Extracted three times by above-mentioned steps, merging extract solution simultaneously will
Extract solution is concentrated into paste, obtains 5 liters of extract solution;
Then extract solution is extracted three times with 5 liters of dichloromethane, obtains water layer and dichloromethane layer, combined dichloromethane layer is simultaneously
Concentration, obtains dichloromethane and extracts 400 grams of medicinal extract;
Water layer adds 4 liters of ethyl acetate to extract three times again, obtains water layer and ethyl acetate layer, respectively combined ethyl acetate layer and water
760 grams of ethyl acetate extract medicinal extract, 630 grams of get Shui positions medicinal extract are obtained after layer concentration.
(3) 400 Ke Shui positions medicinal extract 500mL hot water dissolvings are taken, then by MCI column chromatographies, uses MeOH-H2O volumes
Than 0: 100 to 100: 0 gradient elution, wherein MeOH-H is collected2The elution fraction of O volume ratios 70: 30 to 80: 20;Then by institute
Wash-out component through silica gel column chromatography, with CH2Cl2- MeOH volume ratios 20: 1,15: 1,10: 1,5: 1 to 0: 1 are washed as gradient
It is de-, collect wherein CH2Cl2The elution fraction of-MeOH volume ratios 5: 1;Gained elutes component again through Sephadex LH-20 gel columns
Chromatography, using MeOH as eluent, collection obtains seven elution fractions;Component the six channels Toyopearl column chromatographies, with methyl alcohol
Used as eluent, collection obtains four elution fractions;Component two be tea hill how phenose glycosides C (kaempferol 3-O- [E-
p-coumaroyl-(1→2)][α-L-arabinopyranosyl-(1→3)][β-D-glucopyranosyl-(1→3)-α-
L-rhamnopyranosyl (1 → 6)]-β-D-glucopyranoside, 12.7 milligrams).The separation process is also assigned to simultaneously
The other three flavone glycoside, respectively tea hill how phenose glycosides A, tea quercetin glycoside A, tea quercetin glycoside C.
Embodiment 2:From the preparation in Huang great Cha
(1) 10 kilograms of dry yellow big tea are taken, and is crushed powdered;
(2) 10 kilograms of dry yellow big tea are first extracted 72 hours with 30 liter of 80% acetone water normal temperature first, Ran Hou
Ultrasound extraction 2 hours under 70Hz;Obtain 80% acetone water position extract solution;Extracted three times by above-mentioned steps, merging extract solution simultaneously will
Extract solution is concentrated into paste, obtains 5 liters of extract solution;
Then extract solution liquid is extracted three times with 5 liters of dichloromethane, obtains water layer and dichloromethane layer, combined dichloromethane layer
And concentrate, obtain dichloromethane and extract 700 grams of medicinal extract.
Water layer adds 4 liters of ethyl acetate to extract three times again, obtains water layer and ethyl acetate layer, and combined ethyl acetate layer obtains acetic acid second
625 grams of esteratic site medicinal extract.
Water layer adds 3L extracting n-butyl alcohols three times, obtains water layer and n-butanol layer, after n-butanol layer and water layer concentration are merged respectively
Obtain 128 grams of n-butanol portion medicinal extract, 150 grams of get Shui positions medicinal extract.
93.4 grams of n-butanol portion medicinal extract 150mL hot water dissolvings are taken, by MCI column chromatographies, MeOH-H is used2O volumes
Than 20: 80 to 100: 0 as gradient elution, wherein MeOH-H is collected2The elution fraction of O volume ratios 70: 30 to 80: 20;Then
By the wash-out component of gained through Sephadex LH-20 gel filtration chromatographies, using methyl alcohol as eluent, collection obtains eight
Elution fraction;Through Sephadex LH-20 gel filtration chromatographies, using methyl alcohol as eluent, collection obtains three and washes component four
De- component;Component one is Kaempferol glucosides C (kaempferol 3-O- [E-p-coumaroyl- (1 → 2)] [α-L-
arabinopyranosyl-(1→3)][β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl(1→
6)]-β-D-glucopyranoside, 6.1 milligrams).
Embodiment 3
Raw material is changed to 9.0 kilograms of dry yellow big tea, using the method for embodiment 1, how tea hill of the present invention is prepared
4.2 milligrams of phenose glycosides C.
Embodiment 4
Raw material is changed to 10 kilograms of dry Lu`an Guapian.Tea sample teas, using the method for embodiment 2, the present invention is prepared
Tea hill how 12.5 milligrams of phenose glycosides C.
As can be seen from the above embodiments, from by after extracting n-butyl alcohol, later separation purifying obtains the step of the compound
It is rapid substantially simple.
Comparative example 1
A kind of jasmine tea of in the market is bought, does not extract of the present invention using the method for embodiment 1 and embodiment 2
Tea hill how phenose glycosides C.
Tea hill of the present invention how phenose glycosides C characteristic it is as follows:
1) methyl alcohol and DMSO, are dissolved in, yellow solid,
2)、IR(KBr)vmax(cm-1):3394,1700,1654,1604,1511,1078;
3)、HR-ESI-MS:m/z1033.28429([M-H]-, C24H19O9 -Calculated value for 1033.28251);Core
Resonance spectroscopic data is shown in Table 1.
Table 1:Tea hill how phenose glycosides C spectroscopic data of the nuclear magnetic resonance (1H NMR in 600MHz,13C NMR are in 150MHz conditions
Lower test, δ units are ppm, and coupling constant J units are Hz, and solvent is deuterated DMSO).
The spectroscopic data of the nuclear magnetic resonance of the Kaempferol glucosides C of table 1.
All spectral datas pass through1H NMR,13C NMR, ESI-HR-MS and1H-1The two dimensions such as H COSY, HMQC, HMBC
Nuclear magnetic resoance spectrum belongs to, it was demonstrated that the structure of gained compound.
2nd, tea hill how the suppression 3T3-L1 adipocyte lipids accumulation experiment of phenose glycosides C and the other three flavone glycoside
Cell culture:3T3-L1 PECTORAL LIMB SKELETONs are taken, with containing the dual anti-DMEM culture mediums of 10% hyclone and 1%, with
Certain condition (37 DEG C of temperature, gas concentration lwevel 5%, humidity 95%) is incubated in carbon dioxide constant incubator.
Cell viability is detected:Cell viability is determined using thiazole blue laws.3T3-L1 PECTORAL LIMB SKELETONs are taken according to 3 × 104Individual/
ML is inoculated in 96 orifice plates, and the compound (25,50,100 and 200 μM) of different quality concentration, continuous training are separately added into after culture 24h
The tetrazolium bromide nutrient solution (5mg/ml) of 20 μ l is added after foster 72h, nutrient solution is blotted after culture 4h, 150 μ l diformazans are added per hole
Base sulfoxide, OD value is determined after shaking table vibration 10min with ELIASA at 490nm wavelength.
The induction differentiation of cell and oil red O stain:3T3-L1 PECTORAL LIMB SKELETONs are inoculated in 24 orifice plates, are cultivated using DMEM
Base (containing 10% hyclone) culture, after cell is merged completely, addition insulin differentiating inducer (10 μ g/mL insulin,
0.5mol/L3- isobutyl group 1- methyl yellow Piao purines and 1 μm of ol/L dexamethasone) induction;DMEM medium cultures 8 are replaced with after 3 days
My god.Self-induction starts (0 day), and experimental group adds different quality concentration (25,50,100 μM) compound, and resveratrol is used as the positive
Control group (20 μ g/mE).After 8 days cell with phosphate buffer rinse, with after 10% formalin fix again with 60% it is different
Propyl alcohol drip washing, using 0.5% oil red O stain, observes the deposition of fat in endochylema and takes pictures.Added per hole after oil red dyeing
The cell of 400ul isopropanols treatment dyeing, goes out to detect OD value in ELIASA 510nm.
Test result indicate that, how phenose glycosides C and other three flavone glycosides are hardly produced to 3T3-L1 fat cells in tea hill
Raw cytotoxicity, while the accumulation of lipid in 3T3-L1 fat cells can be reduced effectively.When Kaempferol glucosides C is acted on for 50 μM
During 3T3-L1 fat cells, the relative amount of the lipid in 3T3-L1 fat cells is 55.53%;Kaempferol glucosides C is 100 μM
When, the relative amount of the lipid in 3T3-L1 fat cells is reduced to less than 50%.Illustrate tea hill how phenose glycosides C can be effective
Suppress the accumulation of lipid in 3T3-L1 fat cells, while this inhibition is not that how phenose glycosides C is thin to 3T3-L1 by tea hill
Caused by the cytotoxicity of born of the same parents.
Cytotoxicity of the 2. 4 flavone glycoside monomeric compounds of table to 3T3-L1 cells
1 be tea hill how phenose glycosides C, 2 be tea hill how phenose glycosides A, 3 is tea quercetin glycoside C, and 4 is tea quercetin glycoside A.
Therefore entitled tea hill of the invention how flavones four glucosides of being acylated of phenose glycosides C can be using in terms of lipid-lowering diet drug
Prepare.
Specifically by as above tea hill of the invention, how the glucosides of acylation flavones four of phenose glycosides C is by medically acceptable
Dosage and pharmaceutically general auxiliary material be made a kind of lipid-lowering diet drug.The pharmaceutical dosage form include oral type, external application type and
Injection-type etc..
Above content describes general principle of the invention and principal character, and the present invention is not limited to the above embodiments,
Without departing from the spirit and scope of the present invention, various changes and modifications of the present invention are possible, and these changes and improvements are all
Fall into scope of the claimed invention.
Claims (10)
1. it is a kind of to be acylated the glucosides of flavones four, it is characterised in that be named as tea hill how phenose glycosides C, with structure as shown below:
2. the preparation method of the glucosides of flavones four is acylated according to claim 1, it is characterised in that in turn included the following steps:
1) raw material is crushed:
Dry Lu`an Guapian.Tea sample tea or Huang great Cha are taken, is crushed powdered;
2) extract:
Lu`an Guapian.Tea sample tea or yellow big tea after being crushed with 70-80% acetone flooding obtain leaching liquor, extract by classification
Take and be concentrated under reduced pressure to give last remaining water position paste;
3) isolate and purify:
Water position paste is isolated and purified obtain tea hill how phenose glycosides C.
3. according to claim 2 be acylated the glucosides of flavones four preparation method, it is characterised in that the step 2) extraction in,
Lu`an Guapian.Tea sample tea or yellow big tea after first being crushed with 70-80% acetone flooding obtain leaching liquor, then with dichloromethane, second
Acetoacetic ester fractional extraction, extract solution is obtained corresponding extraction position paste extract by concentrated under reduced pressure:Dichloromethane position, acetic acid
Ethyl ester position and remaining water position paste.
4. the preparation method of the glucosides of flavones four is acylated according to claim 2, it is characterised in that the step 3) described in
Isolate and purify be by water position paste dissolve after successively through MCI column chromatographies, silica gel column chromatography, Sephadex LH-20
Gel filtration chromatography, Toyopearl column chromatographic isolation and purifications.
5. according to claim 2 or 4 be acylated the glucosides of flavones four preparation method, it is characterised in that the step 3) in institute
State isolate and purify concretely comprise the following steps:MCI posts will be crossed after the paste water dissolves of water position and will use MeOH-H2O volume ratios 0:
As gradient elution, collect the elution fraction of wherein MeOH-H2O volume ratio 70: 30 to 80: 20 at 100 to 100: 0;Then by institute
Wash-out component through silica gel column chromatography, with CH2Cl2- MeOH volume ratios 20: 1,15: 1,10: 1,5: 1 to 0: 1 are washed as gradient
It is de-, collect wherein CH2Cl2The elution fraction of-MeOH volume ratios 5: 1;Gained elutes component again through Sephadex LH-20 gel columns
Chromatography, using MeOH as eluent, collection obtains elution fraction;Elution fraction again through Toyopearl column chromatographies, wash-out,
Obtain Kaempferol glucosides C.
6. the preparation method of the glucosides of flavones four is acylated according to claim 1, it is characterised in that in turn included the following steps:
1) raw material is crushed:
Dry Lu`an Guapian.Tea sample tea or Huang great Cha are taken, is crushed powdered;
2) extract:
Lu`an Guapian.Tea sample tea or yellow big tea after being crushed with 70-80% acetone flooding obtain leaching liquor, extract by classification
Take and be concentrated under reduced pressure to give last remaining n-butanol portion paste;
3) isolate and purify:
N-butanol portion paste is isolated and purified obtain tea hill how phenose glycosides C.
7. according to claim 6 be acylated the glucosides of flavones four preparation method, it is characterised in that the step 2) extraction in,
Lu`an Guapian.Tea sample tea or yellow big tea after first being crushed with 70-80% acetone flooding obtain leaching liquor, then with dichloromethane, second
Acetoacetic ester fractional extraction, extract solution is obtained corresponding extraction position paste extract by concentrated under reduced pressure:Dichloromethane position, acetic acid
Ethyl ester position and remaining water position, water position extracting n-butyl alcohol finally obtain n-butanol portion paste;
The step 3) described in isolate and purify be by n-butanol portion paste dissolve after successively through MCI column chromatographies,
Sephadex LH-20 gel filtration chromatographies are isolated and purified and obtain Kaempferol glucosides C;
Preferably, the step 3) described in isolate and purify concretely comprise the following steps:
MCI column chromatographies are crossed after n-butanol portion paste is dissolved and uses MeOH-H2O volume ratios 20: 80 to 100: 0 are used as gradient
Wash-out, collects wherein MeOH-H2The elution fraction of O volume ratios 70: 30 to 80: 20;Then the wash-out component of gained is passed through
Sephadex LH-20 gel filtration chromatographies, using methyl alcohol as eluent, collection obtains elution fraction;Elution fraction is passed through again
Sephadex LH-20 gel filtration chromatographies, wash-out, obtain Kaempferol glucosides C.
8. a kind of application for being acylated the glucosides of flavones four in terms of lipid-lowering diet drug is prepared as claimed in claim 1.
9. the fat medicine of a kind of lowering blood-fat and reducing weight, it is characterised in that the medicine by being acylated flavones tetrose as claimed in claim 1
Glycosides and auxiliary material are made.
10. lipid-lowering diet drug according to claim 9, it is characterised in that the pharmaceutical dosage form includes oral type, external application
Type and injection-type.
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