CN105566436B - A kind of tea seed flavone aglycone and theasapogenol Zn complex and its preparation method and purposes - Google Patents
A kind of tea seed flavone aglycone and theasapogenol Zn complex and its preparation method and purposes Download PDFInfo
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- CN105566436B CN105566436B CN201510962057.4A CN201510962057A CN105566436B CN 105566436 B CN105566436 B CN 105566436B CN 201510962057 A CN201510962057 A CN 201510962057A CN 105566436 B CN105566436 B CN 105566436B
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- theasapogenol
- flavone aglycone
- tea seed
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- 229930192129 Theasapogenol Natural products 0.000 title claims abstract description 51
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 title claims abstract description 47
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 title claims abstract description 47
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- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention belongs to field of medicaments, a kind of tea seed flavone aglycone and theasapogenol Zn complex and its preparation method and purposes are disclosed.Methods described, specifically includes following steps：Degreasing leached tea oil slag is extracted with ethanol water, filters, filtrate is used into sour water solution, concentration, liquid precipitate will be concentrated, sediment ethanol will be redissolved, natrium carbonicum calcinatum, zinc salt is added, back flow reaction, pH is adjusted to 8~10, is staticly settled, is washed, vacuum drying, produces tea seed flavone aglycone and theasapogenol Zn complex.The complex have significantly protection nerve cell, prevent neurodegenerative effect, can as new anti-nerve degenerative diseases medicine application and development.
Description
Technical field
It is more particularly to a kind of that there is neuroprotection tea seed flavone aglycone and theasapogenol the invention belongs to field of medicaments
Zn complex and preparation method thereof, and it is used as the application of anti-neurodegenerative disorders medicine.
Background technology
The many compositions of Chinese medicine have neuroprotection, typically there is flavonoids, saponins compound.The anti-aging of Chinese medicine
Effect is exactly the synergy of Multiple components, but is under study for action usually isolated and purified them respectively, certainly will so drop
Low action effect.
Contain 2~3% flavones and 12~14% saponins compounds in tea seed.Conventional flavones and the separation method of saponin(e
There are extraction, resin method, chromatography etc., chromocor compound and tea saponin can be obtained respectively by isolating and purifying.But separation
The Neuroprotective effect of product is not protruded.
Flavones and saponin(e are more in plant to be existed in the form of glucosides, because molecular weight is larger and water-soluble relatively strong, no
Beneficial to it neuroprotection is played through blood-brain barrier.
Tea seed flavones and sapogenin are not added with separating and directly extracted, flavone aglycone and theasapogenol Zn complex is prepared,
Report is had no as the research of new anti-nerve degeneration medicine.
The content of the invention
In order to overcome shortcoming and defect of the prior art, it is an object of the invention to provide a kind of tea seed flavone aglycone simultaneously
Theasapogenol Zn complex.
Another object of the present invention is to provide the preparation method of above-mentioned tea seed flavone aglycone and theasapogenol Zn complex.
It is still another object of the present invention to provide the application of a kind of above-mentioned tea seed flavone aglycone and theasapogenol Zn complex
The pharmaceutical preparation with neuroprotection being made into.
The purpose of the present invention is achieved through the following technical solutions：
A kind of tea seed flavone aglycone and theasapogenol Zn complex, its structural formula are shown below：
The preparation method of the tea seed flavone aglycone and theasapogenol Zn complex, specifically includes following steps：
Degreasing leached tea oil slag is extracted with ethanol water, filtered, the acid hydrolysis into filtrate, concentration obtains concentrate；To
Precipitating reagent is added in concentrate to be precipitated, and obtains sediment；Sediment is dissolved, natrium carbonicum calcinatum and zinc salt, backflow is added
Reaction, pH is to 8~10 for regulation, staticly settles, and washs, and dries, and obtains tea seed flavone aglycone and theasapogenol Zn complex.
The condition of the concentration is to be concentrated under reduced pressure under 50~80 DEG C and 0.01~0.1 atmospheric pressure, the concentrate
Volume is the 1/3 of filtrate volume.
The precipitating reagent is water, and the consumption of the precipitating reagent is 3~5 times of the volume of concentrate.
Sediment dissolving, which is directed to add absolute ethyl alcohol in sediment, is dissolved, the consumption of the absolute ethyl alcohol and
Sediment is identical in quality.
The material of the regulation pH is ammoniacal liquor；The washing refers to using ethanol washing.
Described to staticly settle 8~24 hours, the condition of the drying is to be dried 3~6 hours in 50~80 DEG C.
The volume fraction of the ethanol water is 70~85%.
The addition of the ethanol water is (10~20) mL with the liquid-solid ratio of degreasing leached tea oil slag raw material：1g；Extract temperature
Spend for 60~80 DEG C, 1~3 hour extraction time.
The acid is hydrochloric acid, into filtrate after acid adding, HCl 2~5mol/L of final concentration；The hydrolysis temperature is 70~80
DEG C, hydrolysis time is 5~8 hours.
The natrium carbonicum calcinatum addition is the 0.5~2% of degreasing tea seed cake quality, and the zinc salt addition is degreasing tea seed cake
The 0.5~2% of quality；The back flow reaction temperature is 70~80 DEG C, and the reaction time is 5~10 hours.
The zinc salt is zinc acetate.
The degreasing leached tea oil slag is the one of which of the degreasing tea seeds dregs of rice or degreasing camellia seed meal.
Simultaneously theasapogenol Zn complex is used to prepare with neuroprotective medicine preparation the tea seed flavone aglycone, yellow
The preparation for the various pharmaceutical dosage forms that ketoside member and theasapogenol Zn complex can be made with any legal compounding ingredient and excipient.
Of the present invention to have in neuroprotective medicine preparation, formulation can appointing for oral or injectable pharmaceutically dosage form
What is a kind of.
The theasapogenol derivative is combined to be made as active component with acceptable pharmaceutical carrier can be used as preventing and controls
Treat the oral of various anti-neurodegenerative diseases or injection folk prescription and compound preparation.
The present invention has the following advantages that and effect compared with prior art：
(1) present invention has flavone aglycone, theasapogenol and zinc ion concurrently simultaneously, and three's Synergistic, Central nervous is protected
Shield activity is significantly improved；
(2) flavone aglycone of the invention and theasapogenol Zn complex preparation method, pass through alcohol extracting using degreasing leached tea oil slag
After hydrolysis, the flavone aglycone of acquisition, theasapogenol structure are small, are conducive to them to pass through blood-brain barrier, play central action；
(3) technique is simple, it is not necessary to isolates and purifies flavones and saponin(e respectively, is easy to industrialized production.
Embodiment
Further detailed description is done to the present invention with reference to embodiment, but the implementation of the present invention is not limited to this.
Embodiment 1
By degreasing tea seeds dregs of rice 1kg, the ethanol water of 10L volume fraction 80% is added, 70 DEG C of refluxing extractions 3 are small
When, filtering, filtrate adds hydrochloric acid to HCl final concentration of 2mol/L, 80 DEG C of hydrolysis times, 5 hours, 80 DEG C and 0.1 atmospheric pressure
Under be concentrated under reduced pressure into the 1/3 of filtrate volume, add 3 times of water sedimentations of the volume of concentrate, the sediment anhydrous second of its equimultiple quality
After alcohol redissolves, natrium carbonicum calcinatum 20g, zinc acetate 10g, 70 DEG C of reaction 10h are added, pH is adjusted to 8 with ammoniacal liquor, staticly settles 24 small
When, after collection precipitation is washed with ethanol, 50 DEG C are dried in vacuo 6 hours, and the flavone aglycone and theasapogenol zinc that 48g is made coordinate
Thing.
Product is made into 0.2mg/mL sample liquid by solvent of DMSO, and UV scanning is shown, the feature of flavones and sapogenin is inhaled
Receive peak and there occurs 10~15nm of red shift；Infrared display, flavones carbonyl peak (1650cm-1) move 40 to low frequency direction~
50cm, and in 500cm-1Place adds a new broad peak, is metal and the stretching vibration peak of oxygen bonding at this, illustrates flavones carbonyl
Base, saponin(e hydroxyl and zinc ion there occurs complexation reaction.Elementary analysis result shows, flavone aglycone, theasapogenol and zinc atom
Proportioning be 1：1：1.
Embodiment 2
By degreasing camellia seed meal 1kg, the ethanol water of 15L volume fraction 70% is added, 60 DEG C of refluxing extractions 2 are small
When, filtering, filtrate adds hydrochloric acid to HCl final concentration 5mol/L, 70 DEG C of hydrolysis times, 8 hours, 50 DEG C and 0.01 atmospheric pressure
Under be concentrated under reduced pressure into the 1/3 of filtrate volume, add 5 times of water sedimentations of the volume of concentrate, the sediment anhydrous second of its equimultiple quality
After alcohol redissolve, natrium carbonicum calcinatum 10g, zinc acetate 5g, 80 DEG C of reaction 5h are added, pH is adjusted to 9 with ammoniacal liquor, staticly settles 8 hours,
After collection precipitation is washed with ethanol, 80 DEG C are dried in vacuo 3 hours, and 36g flavone aglycone and theasapogenol Zn complex is made.
Product be the same as Example 1 is equally detected, as a result consistent with embodiment 1.
Embodiment 3
By degreasing camellia seed meal 1kg, the ethanol water of 12L volume fraction 85% is added, 65 DEG C of refluxing extractions 1 are small
When, filtering, filtrate adds hydrochloric acid to HCl final concentration 3mol/L, 80 DEG C of hydrolysis times, 5 hours, 60 DEG C and 0.05 atmospheric pressure
Under be concentrated under reduced pressure into the 1/3 of filtrate volume, add 4 times of water sedimentations of the volume of concentrate, the sediment anhydrous second of its equimultiple quality
After alcohol redissolves, natrium carbonicum calcinatum 20g, zinc acetate 15g, 70 DEG C of reaction 10h are added；PH is adjusted to 10 with ammoniacal liquor, staticly settles 10
Hour, after collection precipitation is washed with ethanol, 60 DEG C are dried in vacuo 4 hours, and the flavone aglycone and theasapogenol zinc that 52g is made coordinate
Thing.
Product be the same as Example 1 is equally detected, as a result consistent with embodiment 1.
Embodiment 4
By degreasing Camellia Leaves seed dregs of rice 1kg, the ethanol water of 20L volume fraction 80% is added, 65 DEG C of refluxing extractions 2 are small
When, filtering, filtrate adds hydrochloric acid to HCl final concentration 2.5mol/L, 75 DEG C of hydrolysis times 6 hours；Under 70 DEG C and 0.1 atmospheric pressure
It is concentrated under reduced pressure into the 1/3 of filtrate volume, adds 3.5 times of water sedimentations of the volume of concentrate, the sediment anhydrous second of its equimultiple quality
After alcohol redissolves, natrium carbonicum calcinatum 5g, zinc acetate 5g, 80 DEG C of reaction 7h are added；PH is adjusted to 8.5 with ammoniacal liquor, staticly settles 16 small
When, after collection precipitation is washed with ethanol, 70 DEG C are dried in vacuo 4 hours, and the flavone aglycone and theasapogenol zinc that 40g is made coordinate
Thing.
Product be the same as Example 1 is equally detected, as a result consistent with embodiment 1.
Embodiment 5
By degreasing tea seeds dregs of rice 1kg, the ethanol water of 16L volume fraction 75% is added, 75 DEG C of refluxing extractions 1.5 are small
When, filtering, filtrate adds hydrochloric acid to HCl final concentration 4mol/L, 80 DEG C of hydrolysis times 7 hours；Under 70 DEG C and 0.05 atmospheric pressure
It is concentrated under reduced pressure into the 1/3 of filtrate volume, adds 4.5 times of water sedimentations of the volume of concentrate, the sediment anhydrous second of its equimultiple quality
After alcohol redissolves, natrium carbonicum calcinatum 15g, zinc acetate 10g, 75 DEG C of reaction 8h are added；PH is adjusted to 9 with ammoniacal liquor, staticly settles 20 small
When, after collection precipitation is washed with ethanol, 60 DEG C are dried in vacuo 5 hours, and the flavone aglycone and theasapogenol zinc that 45g is made coordinate
Thing.
Product be the same as Example 1 is equally detected, as a result consistent with embodiment 1.
Embodiment 6
By degreasing camellia seed meal 1kg, the ethanol water of 18L volume fraction 70% is added, 80 DEG C of refluxing extractions 2.5 are small
When, filtering, filtrate adds hydrochloric acid to HCl final concentration 4.5mol/L, 75 DEG C of hydrolysis times 8 hours；65 DEG C and 0.03 atmospheric pressure
Under be concentrated under reduced pressure into the 1/3 of filtrate volume, add 5 times of water sedimentations of the volume of concentrate, the sediment anhydrous second of its equimultiple quality
After alcohol redissolves, natrium carbonicum calcinatum 17g, zinc acetate 14g, 80 DEG C of reaction 9h are added, pH is adjusted to 9 with ammoniacal liquor, staticly settles 12 small
When, after collection precipitation is washed with ethanol, 80 DEG C are dried in vacuo 3.5 hours, and the flavone aglycone and theasapogenol zinc that 34g is made coordinate
Thing.
Product be the same as Example 1 is equally detected, as a result consistent with embodiment 1.
Embodiment 7
The flavone aglycone and theasapogenol Zn complex 10g of Example 1~6,3 are pressed with lactose, avicel cellulose:7 mix
Compound 30g, 1% magnesium stearate are well mixed, and every 200mg tablet is made through tablet press machine.
Embodiment 8
Flavone aglycone made from embodiment 1~6 and theasapogenol Zn complex 10g are weighed, medicinal microcrystalline cellulose is added
30g, is well mixed, wet granulation is adjusted with ethanol, and the loose mesh sieve of mistake 20 of particle is made, dries.Capsule is filled after drying, i.e.,
Obtain the capsule of flavone aglycone and theasapogenol Zn complex.
Embodiment 9
The flavone aglycone and theasapogenol Zn complex 10g of Example 1~6, after being dissolved with Spheron MD 30/70 1000mL,
Bottle is poured into, injection is made.
Embodiment 10
Flavone aglycone made from embodiment 1~6 and theasapogenol Zn complex 10g are weighed, 50g PEG6000 are added, plus
It is well mixed after heat to 60 DEG C of fusings, is placed in pill dripping machine, uses atoleine refrigeration, dripping pill.Cooling produces flavone aglycone and tea
The pill of sapogenin Zn complex.
The flavone aglycone and theasapogenol Zn complex of the present invention has notable neuroprotection, is tested by following
To confirm.
(1) to the protective effect of glutamic acid (Glu) injury rats hippocampal tissue
Method：4~5 monthly age male Wistar rat 40 is taken, body weight (200 ± 20) g is randomly divided into sham-operation group, Glu
Damage group, flavone aglycone and theasapogenol Zn complex group, kaempferol group, Tea Saponin group every group 8.The advance gavage of administration group is given
Medicine 10d, remaining group gavage normal saline.Mouse is fixed on stereotaxic apparatus after tail vein injection Thiopental Anesthesia,
Calvarium center skin and periosteum are cut, brill at bregma, the 0.8mm after bregma, the other 1.5mm in sagittal suture right side is clearly exposed and opens cranium
Bone, with micro syringe row intracerebroventricular injection Glu4 μ L (1mg/kg), depth of needle 3.8mm, let the acupuncture needle remain at a certain point 5min.Take and observe big after pin
Mouse behaviouristics changes, and is succeeded with there is the model that shows as of epilepsy seizure.Inject after Glu solution 2h, by rat sacrificed by decapitation,
Full brain is taken rapidly, hippocampus is isolated, and normal saline is added after weighing into 1：The hippocampal homogenates of 10 (w/vs).
Each group hippocampal homogenates are taken, are operated in strict accordance with kit specification, with multi-function microplate reader detection wherein MDA contents, SOD
With GSH-Px activity.It the results are shown in Table 1.
As a result：Intracerebroventricular injection Glu can cause MDA contents in Rat hippocampus to raise, SOD and GSH-Px activity drop
Low (p<0.05)；Compared with Glu damage groups, medicine group MDA contents are reduced, SOD and GSH-Px activity are raised, flavonoid glycoside
Member and theasapogenol Zn complex group change maximum, up to the level of signifiance (P<0.01), show flavone aglycone and theasapogenol zinc is matched somebody with somebody
Compound can improve the activity of intracerebral antioxidase and antagonism Glu neurotoxicity, and with neuroprotection, its effect is better than mountain
Naphthols and Tea Saponin group.
Simultaneously theasapogenol Zn complex influences the flavone aglycone of table 1 on activities of antioxidant enzymes in hippocampal tissue
(2) Protection damaged to MPTP induced mices dopamine neuron
Method：5~6 monthly age male mice 50 is taken, body weight (20 ± 2) g is randomly divided into Normal group, MPTP groups, Huang
Ketoside member and theasapogenol Zn complex, kaempferol group, Tea Saponin group, every group 10.The advance intraperitoneal injection 3d of administration group,
1 time a day, remaining group intraperitoneal injection normal saline.4d is in addition to normal group, other injection MPTP solution 4mg/kg.7d
Afterwards, by mouse sacrificed by decapitation, full brain being taken rapidly, corpus straitum is isolated, PE buffers are added after weighing into 1：10 (weighing bodies
Product ratio) tissue homogenate.After homogenate centrifugation, dopamine (DA) content is determined through HPLC.It the results are shown in Table 2.
As a result：MPTP group DA contents significantly reduce (p compared with normal group<0.05), show that MPTP causes dopamine neuron
Damage.Flavone aglycone and theasapogenol Zn complex administration group DA contents and MPTP significantly improve (p according to a group ratio<0.05), say
Simultaneously damage of the theasapogenol Zn complex to dopamine neuron caused by MPTP has preferable protective effect to bright flavone aglycone.
The flavone aglycone of table 2 and influence of the theasapogenol Zn complex to striatum DA level
Claims (10)
1. a kind of tea seed flavone aglycone and theasapogenol Zn complex, it is characterised in that：Its structural formula is shown below：
2. the preparation method of tea seed flavone aglycone and theasapogenol Zn complex according to claim 1, it is characterised in that：Tool
Body comprises the following steps：Degreasing leached tea oil slag is extracted with ethanol water, filtered, the acid hydrolysis into filtrate, concentration obtains dense
Contracting liquid；Precipitating reagent is added into concentrate to be precipitated, and obtains sediment；Sediment is dissolved, natrium carbonicum calcinatum and zinc is added
Salt, back flow reaction, pH is to 8~10 for regulation, staticly settles, and washs, and dries, and produces tea seed flavone aglycone and theasapogenol zinc coordinates
Thing.
3. the preparation method of tea seed flavone aglycone and theasapogenol Zn complex according to claim 2, it is characterised in that：Institute
The volume fraction for stating ethanol water is 70~85%；The Extracting temperature is 60~80 DEG C, 1~3 hour extraction time；It is described
70~80 DEG C of hydrolysis temperature, hydrolysis time 5~8 hours；70~80 DEG C of the back flow reaction temperature, the reaction time is 5~10h.
4. the preparation method of tea seed flavone aglycone and theasapogenol Zn complex according to claim 2, it is characterised in that：Institute
It is (10~20) mL that the addition of ethanol water, which is stated, with the liquid-solid ratio of degreasing leached tea oil slag raw material：1g；The acid is hydrochloric acid；It is described
Hydrochloric acid adds final concentration of 2~5mol/L of HCl after filtrate.
5. the preparation method of tea seed flavone aglycone and theasapogenol Zn complex according to claim 2, it is characterised in that：Institute
It is the 0.5~2% of degreasing tea seed cake quality to state natrium carbonicum calcinatum addition, and the zinc salt addition is the 0.5 of degreasing tea seed cake quality
~2%；The zinc salt is zinc acetate.
6. the preparation method of tea seed flavone aglycone and theasapogenol Zn complex according to claim 2, it is characterised in that：Institute
State sediment dissolving be directed in sediment add absolute ethyl alcohol dissolved, the consumption and sediment of ethanol are identical in quality.
7. the preparation method of tea seed flavone aglycone and theasapogenol Zn complex according to claim 2, it is characterised in that：Institute
The condition of concentration is stated to be concentrated under reduced pressure under 50~80 DEG C and 0.01~0.1 atmospheric pressure, the volume of concentrate is filtrate body
Long-pending 1/3；The condition of the drying is 50~80 DEG C and dried 3~6 hours.
8. the preparation method of tea seed flavone aglycone and theasapogenol Zn complex according to claim 2, it is characterised in that：Institute
Precipitating reagent is stated for water, the consumption of precipitating reagent is 3~5 times of the volume of concentrate；The material of the regulation pH is ammoniacal liquor；The washing is
Refer to and washed using ethanol；The degreasing leached tea oil slag is middle one kind of the degreasing tea seeds dregs of rice or degreasing camellia seed meal.
9. the application of tea seed flavone aglycone and theasapogenol Zn complex according to claim 1, it is characterised in that：The tea
Simultaneously theasapogenol Zn complex is used to prepare with neuroprotective medicine preparation seed flavone aglycone.
10. the application of theasapogenol Zn complex according to claim 9, it is characterised in that：The formulation of the pharmaceutical preparation
For external application, one kind of oral or injectable pharmaceutically dosage form.
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| CN108383891B (en) * | 2018-03-03 | 2020-10-20 | 广西师范大学 | Method for extracting saponin and co-producing kaempferol from camellia oleifera abel cake |
| CN115364161A (en) * | 2021-12-29 | 2022-11-22 | 江西环境工程职业学院 | Tea oil glycoprotein saponin nano intestinal probiotic accelerant and preparation method and application thereof |
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