CN106631747A - Application of novel compound in preparation of liver protection drugs or health care products - Google Patents
Application of novel compound in preparation of liver protection drugs or health care products Download PDFInfo
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- CN106631747A CN106631747A CN201710070256.3A CN201710070256A CN106631747A CN 106631747 A CN106631747 A CN 106631747A CN 201710070256 A CN201710070256 A CN 201710070256A CN 106631747 A CN106631747 A CN 106631747A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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Abstract
The invention relates to an application of a novel compound in preparation of liver protection drugs or health care products and further relates to a method for preparing the compound through extraction, separation and purification from Sabia parviflora. The pharmacological research indicates that the novel compound can reduce the content of ALT (alanine aminotransferase) and AST (aspartic transaminase) in serum of a CC14 induced acute liver injury model mouse, a D-galactosamine induced acute liver injury model mouse and an ethanol induced liver injury model mouse, reduce the content of MDA (methylene dioxyamphetamine) in liver tissue and enhance SOD (superoxide dismutase) activity of the liver, has a remarkable protection effect on liver injury and is expected to be developed into new drugs or health care products with the liver protection function.
Description
Technical field
The present invention relates to a kind of application of new compound in hepatic or health products is prepared, category medical science neck
Domain.
Background technology
Sabia parviflora Wall.ex Roxb is Sabiaceae fresh breeze Calamus liana Sabia parviflora Wall.ex Roxb Sabia parviflora
Wall.ex Roxb.'s is dried stem.It is the Bouyei, the Folk medicine of Miao ethnic group that Sabia parviflora Wall.ex Roxb is produced in Guizhou, is mainly distributed on Guizhou
The ground such as Xingyi City, Anlong County, Ceheng County, Wangmo County, its rhizome, leaf can be used as medicine, and play the role of dispelling wind and eliminating dampness, anti-inflammatory analgetic,
Treatment A type and virus B hepatitis are evident in efficacy, and Small side effects.Its related kind, clinic is used for the phase of liver region
Related disorders, however, at present main active fails to understand that the working substance of its liver disease is still unclear in Sabia parviflora Wall.ex Roxb.This
Invention carries out system further investigation to Sabia parviflora Wall.ex Roxb chemical composition, and screening obtains the noval chemical compound with hepatoprotective effect.
The content of the invention
The purpose of the present invention is that the chemical composition to Sabia parviflora Wall.ex Roxb is furtherd investigate, there is provided a kind of new compound exists
Prepare hepatic or the application in health products.
A kind of new compound：2,2- dimethyl -3- methylol -4,5- dihydroxy -6- (3- methyl -3- hydroxyl-1-butenes
Base) -1H- 1-Indanones, its structural formula is as follows：
A kind of extraction separation method of new compound, comprises the following steps：
(1) dry Sabia parviflora Wall.ex Roxb medicinal material is taken, the ethanol of concentration 70% for adding 12 times of weight is extracted three times, time difference
For 5 hours, 3 hours, 3 hours, filter, merge extract, be evaporated to without alcohol taste, obtain extract；
(2) extract for taking step (1) adds concentration solubilized for 20-50% ethanol, and with centrifuge insoluble matter is removed,
Obtain supernatant；
(3) macroporous resin column on the supernatant that step (2) is obtained is taken, first 5 column volumes is eluted with 30% alcohol-water, is obtained
To stream part 1, then 5 column volumes are eluted with 50% alcohol-water, concentration is dried, and obtains stream part 2, takes the Jing 200-300 purposes of stream part 2
Silica gel column chromatography, with the mixed liquor of dichloromethane and methyl alcohol successively by volume 20:1、10:1、5:1、2:1 gradient elution, each
Concentration gradient elutes 4 column volumes, and each column volume connects 4 stream parts, and each stream part 500ml is obtained 16 stream parts, takes dichloro
The mixeding liquid volume ratio of methane and methyl alcohol is 20:4 flow points of 1 wash-out, merge, Jing gel filtration chromatographies, with methanol-eluted fractions 10 times,
10 stream parts are obtained successively, and each stream part 50ml takes the merging of stream part 3-8, then Jing ODS mesolow column chromatographies, with first alcohol and water
Mixed liquor successively by volume 1:9、3:7、1:1、7:3、1:0 wash-out, the mixeding liquid volume ratio for taking first alcohol and water is 1:0 elutes
The stream part for arriving, finally with preparative high-performance liquid chromatographic, chromatographic condition is：ODS chromatographic columns, methanol-water 60：40 is mobile phase, is protected
Time 29min is stayed, pure compound is finally separating to obtain.
Wherein, the extracting method described in step (1) be cold-maceration, percolation, microwave loss mechanisms, ultrasonic extraction, return
Stream extraction method or continuous circumfluence extraction method.
The invention provides a kind of application of new compound in hepatic or health products is prepared.
The invention provides a kind of pharmaceutical composition, it includes a kind of noval chemical compound of therapeutically effective amount and its pharmaceutically may be used
The carrier of acceptance, prepare piece agent, capsule, injection, powder-injection, granule, fat emulsion, micro-capsule, dripping pill, ointment or
Skin-permeable and control-released plaster.
Description of the drawings
The structural representation of a kind of new compound that Fig. 1 is provided for the present invention；
Specific embodiment
According to following embodiments, the present invention can be better understood from.
Embodiment 1
A kind of extraction separation method of new compound, comprises the following steps：
(1) dry Sabia parviflora Wall.ex Roxb medicinal material 100kg is taken, the ethanol of concentration 70% for adding 12 times of weight is extracted three times, when
Between be respectively 5 hours, 3 hours, 3 hours, filter, merge extract, be evaporated to without alcohol taste, obtain extract；
(2) extract for taking step (1) adds concentration solubilized for 20-50% ethanol, and with centrifuge insoluble matter is removed,
Obtain supernatant；
(3) macroporous resin column on the supernatant that step (2) is obtained is taken, first 5 column volumes is eluted with 30% alcohol-water, is obtained
To stream part 1, then 5 column volumes are eluted with 50% alcohol-water, concentration is dried, and obtains stream part 2, takes the Jing 200-300 purposes of stream part 2
Silica gel column chromatography, with the mixed liquor of dichloromethane and methyl alcohol successively by volume 20:1、10:1、5:1、2:1 gradient elution, each
Concentration gradient elutes 4 column volumes, and each column volume connects 4 stream parts, and each stream part 500ml is obtained 16 stream parts, takes dichloro
The mixeding liquid volume ratio of methane and methyl alcohol is 20:4 flow points of 1 wash-out, merge, Jing gel filtration chromatographies, with methanol-eluted fractions 10 times,
10 stream parts are obtained successively, and each stream part 50ml takes the merging of stream part 3-8, then Jing ODS mesolow column chromatographies, with first alcohol and water
Mixed liquor successively by volume 1:9、3:7、1:1、7:3、1:0 wash-out, the mixeding liquid volume ratio for taking first alcohol and water is 1:0 elutes
The stream part for arriving, finally with preparative high-performance liquid chromatographic, chromatographic condition is：ODS chromatographic columns, methanol-water 60：40 is mobile phase, is protected
Time 29min is stayed, pure compound (yield is finally separating to obtain：890mg, purity：99.3%), the structural formula figure such as institute of accompanying drawing 1
Show.
The structure elucidation of compound：
Mainly utilize spectral technique, including ultraviolet, infrared, mass spectrum, nuclear magnetic resonance (1H-NMR、13C-NMR, 2D-NMR) mirror
Determine its structure, then Jing TOF high resolution mass spectrums accurately determine its molecular weight and molecular formula.
Its spectral data is as follows：
(1) white amorphous powder, high resolution mass spectrum ESI-TOF-MS：305.1381[M-H]-.Determine that molecular formula is
C17H22O5, δ in H NMR spectroscopyC:211.3 (C-1), show there is carbonyl in structure；δC：19.4,26.4,27.4,27.5(C-8,9,
13,14), with δH:1.20,1.18(each,3H,s,-CH3),1.49,1.50(each,3H,s,-CH3) it is on four quaternary carbons
Methyl signals, δC：113.1(C-7),122.8(C-6),128.6(C-1a),147.2(C-5),143.3(C-4),140.7(C-
3a), δ H:6.97 (1H, s, H-7), may be containing a five substituted phenyl ring, δ in prompting structureC：122.0(C-12),131.9
And δ (C-11)H:5.79 (1H, d, J=9.6Hz H-11), 6.42 (1H, d, J=9.6Hz, H-12), show structure have one it is suitable
Formula double bond.δC：51.6(C-3),δH:3.21 (1H, dd, J=5.2,6.7Hz, H-3) and 61.5 (C-10), δ H:3.94(1H,
Dd, J=10.5,6.8Hz, H-10a), 3.98 (1H, dd, J=5.2,10.6Hz, H-10b), may contain in prompting structure-
CH-CH2- structure fragment, above structure by HMBC, HSQC, finally determines the structure of compound, as shown in Figure 1 again.1H
NMR(600MHz,CD3OD)δ:1.19,1.17(each,3H,s,-CH3),1.48,1.49(each,3H,s,-CH3),3.21
(1H, dd, J=5.2,6.7Hz, H-3), 3.94 (1H, dd, J=10.5,6.8Hz, H-10a), 3.98 (1H, dd, J=5.2,
10.6Hz, H-10b), 5.79 (1H, d, J=9.6Hz H-11), 6.42 (1H, d, J=9.6Hz, H-12), 6.97 (1H, s, H-
7)
13C NMR(600MHz,CD3OD):211.3(C-1),128.6(C-1a),48.5(C-2),51.6(C-3),140.7
(C-3a),143.3(C-4),147.2(C-5),122.8(C-6),113.1(C-7),19.4,26.4(C-8,9),61.5(C-
10),131.9(C-11),122.80(C-12),78.2(C-13),27.4,27.5(C-14,15).
The effect experiment of embodiment 2 is studied
First, experiment material and animal
1. medicine and reagent
Glutamate-pyruvate transaminase determination reagent kit (R1, R2) (Japanese Wako Pure Chemical Industries, Ltd.), glutamic-oxalacetic transaminease are determined
Kit (R1, R2) (Japanese Wako Pure Chemical Industries, Ltd.), superoxide dismutase (SOD), MDA (MDA) kit
(building up Bioengineering Research Institute purchased from Nanjing)；Carbon tetrachloride (analysis is pure), is configured to before use 0.1% peanut with peanut oil
Oil solution；D-Gal (moistens into bio tech ltd in Shanghai), before use with physiological saline be made into 10% it is water-soluble
Liquid；Bicyclol (Beijing XieHe medicine Factory), wears into before use fine powder 0.5%CMC-Na and makes 1.25mg/ml suspensions.
2. animal used as test
Cleaning grade ICR mouse, body weight 18-22g, Hunan SJA Laboratory Animal Co. ， Ltd, quality certification number：SCXK
(Hunan) 2013-0004.
3. laboratory apparatus
The type automatic clinical chemistry analyzer (Hitachi, Ltd) of Hitachi 7180, AL204 type electronic analytical balance (Mettler
Toledo instruments (Shanghai) Co., Ltd.), HC-3018R type high speed freezing centrifuges (limited public affairs of good scientific instrument in section in Anhui
Department), MTV -100 type multitube whirlpool mixed instrument (Hangzhou Ao Sheng Instrument Ltd.), KQ-4000B type supersonic cleaning machines (Gongyi
Yu Hua instruments Co., Ltd of city).
4. test medicine and processing method
The compound that Example 1 is prepared, it is 1.5mg/ml to be diluted with water into concentration, and positive drug is bicyclic alcohols, is faced
With the suspension for front wearing into fine powder 0.5%CMC-Na and making desired concn.
2nd, experimental technique
1. couple CCl4Cause the impact of acute liver
ICR male mices 48 are taken, 4 groups are randomly divided into：Blank control group, model group, positive drug bicyclic alcohols group (25mg
kg-1·d-1), the compound group (30mgkg for preparing of embodiment 1-1·d-1).Blank control group and model group give equivalent
Distilled water, administration group gastric infusion, continuous 7d, the 2h after last dose, in addition to blank control group, remaining each group lumbar injection
0.1%CCl4Peanut oil solution 10mLkg-1；Water is can't help in the physiological saline of blank control group lumbar injection same volume, fasting,
16h posterior orbits take blood.Acquired blood, with 3000rmin-1Centrifugation 10min, takes supernatant, determines by kit method of operating
CCl4 causes ALT, AST content in hepatic injury mice serum.Take and put to death after blood mouse, liver is taken rapidly, picks surrounding connective tissue
It is put into after removing in ice-cold physiological saline and cleans blood stains, take partial liver, make 10% LH, determines according to kit explanation
MDA contents and SOD vigor.
2. pair D-Gal causes the impact of acute liver
ICR male mices 48 are taken, 4 groups are randomly divided into：Blank control group, model group, positive drug bicyclic alcohols group (25mg
kg-1·d-1), the compound group (30mgkg for preparing of embodiment 1-1·d-1).Blank control group and model group give equivalent
Distilled water, administration group gastric infusion, continuous 7d, the 2h after last dose, in addition to blank control group, remaining each group lumbar injection
10%D- amine-galactose solution 10mLkg-1；Water is can't help in the physiological saline of blank control group lumbar injection same volume, fasting,
16h posterior orbits take blood.Acquired blood, with 3000rmin-1Centrifugation 10min, takes supernatant, determines by kit method of operating
D-Gal causes ALT, AST content in hepatic injury mice serum.Take and put to death after blood mouse, liver is taken rapidly, will around be tied
Form to be put in ice-cold physiological saline after tissue is rejected and clean blood stains, take partial liver, 10% LH is made, according to kit
Illustrate to determine MDA contents and SOD vigor.
3. pair ethanol causes the impact of mouse liver injury
ICR male mices 48 are taken, 4 groups are randomly divided into：Blank control group, model group, positive drug bicyclic alcohols group (25mg
kg-1·d-1), the compound group (30mgkg for preparing of embodiment 1-1·d-1).Blank control group mouse gives physiological saline
10ml/kg, 2 times, is spaced 4h.Model group mouse gives physiological saline 10ml/kg, after the 4h of interval, gives 50% ethanol 5ml/kg.
Positive drug group mouse gives bicyclic alcohols medicine, after the 4h of interval, gives 50% ethanol 5ml/kg.The chemical combination that embodiment 1 is prepared
Thing group mouse gives the compound that embodiment 1 is prepared, and after the 4h of interval, gives 50% ethanol 5ml/kg.It is grouped according to more than
Method, the mode that gives of the compound that physiological saline, alcohol and bicyclic alcohols, embodiment 1 are prepared is oral gavage, often
It once, continuous 20d.Last gavage 24h posterior orbit takes blood.Acquired blood, with 3 000rmin-1Centrifugation 10min, takes
Clear liquid, determines alcohol and causes ALT, AST content in hepatic injury mice serum by kit method of operating.Take and put to death after blood mouse, it is fast
Speed takes liver, surrounding connective tissue is rejected after be put in ice-cold physiological saline and clean blood stains, take partial liver, make 10%
LH, according to kit explanation MDA contents and SOD vigor are determined.
4. statistical procedures
Each group experimental data is represented with X ± S, using statistic software SPSS 19.0, each index in hepatic injury test serum
The data of measure are checked using t is compared between variance analysis group, P<0.05 has statistical significance for difference.
3rd, experimental result
1st, this compound is to CCl4Cause the impact of acute liver
CCl4Liver injury model group compares with normal group, mice serum ALT, AST and the significantly raised (P of hepatic tissue MDA levels
<0.01), SOD activity substantially reduces (P<0.01)；The compound of the present invention, bicyclic alcohols group compare with model group, in various degree
Make hepatic injury mice serum ALT, AST reduce (P<0.01)；This compound has reduces hepatic tissue MDA levels, raises liver group
Knit effect of SOD levels；Specific experiment the results are shown in Table 1.
1 compound of table is to CCl4Cause acute hepatic injury mice Serum ALT, AST and liver SOD, the impact (mean of MDA
± SD, n=12)
Note：*Represent compared with model group, significant difference (*P<0.05),**Represent compared with model group, difference extremely shows
Write (**P<0.01)。
2nd, this compound causes the impact of acute liver to D-Gal
D-Gal liver injury model group compares with normal group, and mice serum ALT, AST and hepatic tissue MDA levels are bright
It is aobvious to raise (P<0.01), SOD activity substantially reduces (P<0.01)；Compound group group and bicyclic alcohols group that embodiment 1 is prepared
Compare with model group and make to some extent hepatic injury mice serum ALT, AST reduction (P<0.01)；What embodiment 1 was prepared
Compound group and bicyclic alcohols group compare with model group and make to some extent hepatic injury mouse tissue MDA levels reduction (P<
0.05), SOD levels raise (P<0.05).Specific experiment the results are shown in Table 2.
2 compounds of table cause acute hepatic injury mice Serum ALT, AST and liver SOD, the shadow of MDA to D-Gal
Ring (mean ± SD, n=12)
Note：*Represent compared with model group, significant difference (*P<0.05),**Represent compared with model group, difference extremely shows
Write (**P<0.01)。
3rd, this compound causes the impact of acute liver to ethanol
Ethanol causes liver injury model group to compare with normal group, and mice serum ALT, AST and hepatic tissue MDA levels are significantly raised
(P<0.01), SOD activity substantially reduces (P<0.01)；Compound group, bicyclic alcohols group and model group ratio that embodiment 1 is prepared
Hepatic injury mice serum ALT, AST is set to reduce (P more to some extent<0.05)；Compound group that embodiment 1 is prepared and
Bicyclic alcohols group compares with model group and make to some extent hepatic injury mouse tissue MDA levels reduction (P<0.05), SOD levels liter
Height (P<0.05).Specific experiment the results are shown in Table 3.
The compound of table 3 causes hepatic injury mice serum ALT, AST and liver SOD, impact (mean ± SD, the n of MDA to ethanol
=12)
Note：*Represent compared with model group, significant difference (*P<0.05),**Represent compared with model group, difference extremely shows
Write (**P<0.01)。
Above test result indicate that, the present invention provide compound can significantly reduce CCl4, D-Gal and ethanol
Caused liver injury model mice serum ALT, AST content, Liver MDA, strengthen liver SOD activity.
Therefore, the new compound that the present invention is prepared is expected to be developed into a new generation safely and effectively, for preventing and treating liver
The medicine or health products of damage.
Claims (5)
1. a kind of new compound：2,2- dimethyl -3- methylol -4,5- dihydroxy -6- (3- methyl -3- hydroxyl-1-butenes
Base) -1H- 1-Indanones, its structural formula is as follows：
2. a kind of new compound as claimed in claim 1, it is characterised in that：Extraction separation method is comprised the following steps：
(1) dry Sabia parviflora Wall.ex Roxb medicinal material is taken, the ethanol of concentration 70% for adding 12 times of weight is extracted three times, and the time is respectively 5
Hour, 3 hours, 3 hours, filter, merge extract, be evaporated to without alcohol taste, obtain extract；
(2) extract for taking step (1) adds concentration solubilized for 20-50% ethanol, and with centrifuge insoluble matter is removed, and obtains
Supernatant；
(3) macroporous resin column on the supernatant that step (2) is obtained is taken, first 5 column volumes is eluted with 30% alcohol-water, is flowed
Part 1, then 5 column volumes are eluted with 50% alcohol-water, concentration is dried, and obtains stream part 2, takes the silica gel of the Jing 200-300 mesh of stream part 2
Column chromatography, with the mixed liquor of dichloromethane and methyl alcohol successively by volume 20:1、10:1、5:1、2:1 gradient elution, each concentration
4 column volumes of gradient elution, each column volume connects 4 stream parts, and each stream part 500ml is obtained 16 stream parts, takes dichloromethane
It is 20 with the mixeding liquid volume ratio of methyl alcohol:4 flow points of 1 wash-out, merge, Jing gel filtration chromatographies, with methanol-eluted fractions 10 times, successively
10 stream parts are obtained, each stream part 50ml takes the merging of stream part 3-8, then Jing ODS mesolow column chromatographies, with the mixing of first alcohol and water
Liquid successively by volume 1:9、3:7、1:1、7:3、1:0 wash-out, the mixeding liquid volume ratio for taking first alcohol and water is 1:0 affords
Stream part, finally with preparative high-performance liquid chromatographic, chromatographic condition is：ODS chromatographic columns, methanol-water 60：40 is mobile phase, during reservation
Between 29min, be finally separating to obtain pure compound.
3. a kind of new compound as claimed in claim 2, it is characterised in that：Extracting method described in step (1) is cold
Leaching method, percolation, microwave loss mechanisms, ultrasonic extraction, reflux extraction or continuous circumfluence extraction method.
4. application of a kind of new compound in hepatic or health products is prepared as claimed in claim 1.
5. a kind of pharmaceutical composition, it is characterised in that：A kind of noval chemical compound including therapeutically effective amount and its pharmaceutically acceptable
Carrier, prepare piece agent, capsule, injection, powder-injection, granule, fat emulsion, micro-capsule, dripping pill, ointment or transdermal
Control-released plaster.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108084009A (en) * | 2017-12-27 | 2018-05-29 | 江西本草天工科技有限责任公司 | A kind of compound in Sabia parviflora Wall.ex Roxb and preparation method and application |
| CN108164574A (en) * | 2017-12-27 | 2018-06-15 | 江西本草天工科技有限责任公司 | A kind of compound in Sabia parviflora Wall.ex Roxb and preparation method and application |
| CN109810154A (en) * | 2018-04-16 | 2019-05-28 | 江西本草天工科技有限责任公司 | Sabia parviflora Wall.ex Roxb alkaloid compound, preparation method, using and combinations thereof |
| CN111925404A (en) * | 2020-09-09 | 2020-11-13 | 江西中医药大学 | Preparation method and application of lignan compound |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103880913A (en) * | 2014-04-03 | 2014-06-25 | 南京中医药大学 | Compound with liver protection effect and application thereof |
-
2017
- 2017-02-08 CN CN201710070256.3A patent/CN106631747B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103880913A (en) * | 2014-04-03 | 2014-06-25 | 南京中医药大学 | Compound with liver protection effect and application thereof |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108084009A (en) * | 2017-12-27 | 2018-05-29 | 江西本草天工科技有限责任公司 | A kind of compound in Sabia parviflora Wall.ex Roxb and preparation method and application |
| CN108164574A (en) * | 2017-12-27 | 2018-06-15 | 江西本草天工科技有限责任公司 | A kind of compound in Sabia parviflora Wall.ex Roxb and preparation method and application |
| CN109810154A (en) * | 2018-04-16 | 2019-05-28 | 江西本草天工科技有限责任公司 | Sabia parviflora Wall.ex Roxb alkaloid compound, preparation method, using and combinations thereof |
| CN111925404A (en) * | 2020-09-09 | 2020-11-13 | 江西中医药大学 | Preparation method and application of lignan compound |
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|---|---|
| CN106631747B (en) | 2019-05-07 |
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