CN108084009A - A kind of compound in Sabia parviflora Wall.ex Roxb and preparation method and application - Google Patents
A kind of compound in Sabia parviflora Wall.ex Roxb and preparation method and application Download PDFInfo
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- CN108084009A CN108084009A CN201711441077.2A CN201711441077A CN108084009A CN 108084009 A CN108084009 A CN 108084009A CN 201711441077 A CN201711441077 A CN 201711441077A CN 108084009 A CN108084009 A CN 108084009A
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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
Abstract
The application belongs to pharmaceutical technology field, discloses a kind of compound and preparation method and application in Sabia parviflora Wall.ex Roxb.The compound its be 2 methyl, 2,3 dihydroxymethyl 4,5 dihydroxy 6 (3 methyl, 3 hydroxyl, 1 cyclobutenyl) 1H indenes, 1 ketone.The preparation method of compound of the present invention is easy to operate, can separate and obtain pure compound.Experiment show compound of the present invention can significantly reduce aliphatic acid caused by triacylglycerol content, caspase3 vigor in liver cell, raise MDA contents, reduce hepatocellular apoptosis rate, can be used for preventing nonalcoholic fatty liver damage.Therefore the application the present invention provides the compound in the drug for preparing treatment nonalcoholic fatty liver damage.
Description
Technical field
The invention belongs to pharmaceutical technology fields, and in particular to a kind of compound in Sabia parviflora Wall.ex Roxb and preparation method thereof with
Using more particularly, to the application in the drug for preparing treatment nonalcoholic fatty liver damage.
Background technology
Nonalcoholic fatty liver (NAFLD) is also known as non-alcohol fatty liver, false alcoholic liver disease, is a kind of liver group
It is similar with alcoholic liver disease to knit change, but the clinical pathology syndrome without excessive drinking history, pathological change is with the course of disease
It is in progress and is presented with simple fatty liver, steatohepatitis, fatty liver fibrosis and hepatic sclerosis.With fat and its related generation
Thank to the fashion trend of syndrome globalization, non-alcohol fatty liver has become the developed countries such as America and Europe and China abundantly
The Important cause of disease of area's chronic liver disease, average adult NAFLD illness rates 10%~30%, wherein 10%~20% is non-alcoholic fat
Fat hepatitis (NASH), hepatic sclerosis incidence is up to 25% in the latter 10 years.
Non-alcohol fatty liver in addition to it can directly result in decompensated liver cirrhosis, hepatocellular carcinoma and liver transplantation recur,
The progress of other chronic liver diseases can be also influenced, and participates in the morbidity of diabetes B and atherosclerosis.Metabolic syndrome is related
Malignant tumour, arteriosclerotic cardiovascular and cerebrovascular disease and hepatic sclerosis are influence patients with nonalcoholic fatty liver disease quality of life
And an important factor for life expectancy.For this purpose, non-alcohol fatty liver is the new challenge in contemporary medical science field, non-wine at no distant date
Essence fatty liver disease will be continuously increased the harm of human health.
Sabia parviflora Wall.ex Roxb is Sabiaceae fresh breeze Calamus liana Sabia parviflora Wall.ex Roxb Sabia parviflora
The drying stem of Wall.ex Roxb..Guizhou production Sabia parviflora Wall.ex Roxb is the Bouyei, the Folk medicine of Miao ethnic group, is mainly distributed on Guizhou
The ground such as Xingyi City, Anlong County, Ceheng County, Wangmo County, rhizome, leaf can be used as medicine, and have dispelling wind and eliminating dampness, anti-inflammatory analgetic, heat-clearing profit
Wet, hemostasis effect, for jaundice with damp-heat pathogen, traumatic hemorrhage, treats A type and virus B hepatitis is evident in efficacy, and side effect
It is small.Its related kind of Sabia parviflora Wall.ex Roxb, clinic are chiefly used in the relevant disease of liver region, however, main in Sabia parviflora Wall.ex Roxb at present
Want active ingredient unknown, the working substance of liver disease is still unclear.
The content of the invention
The purpose of the present invention is the chemical composition to Sabia parviflora Wall.ex Roxb is furtherd investigate, one in Sabia parviflora Wall.ex Roxb is provided
Kind compound and preparation method and application.
A kind of compound in Sabia parviflora Wall.ex Roxb is 2- methyl -2,3- dihydroxymethyl -4,5- dihydroxy -6- (3- first
Base -3- hydroxyl-1-butenes base) -1H- 1-Indanones, structural formula shown in formula I,
The present invention also provides the preparation methods of compound shown in Formulas I, comprise the following steps：
(1) Sabia parviflora Wall.ex Roxb is taken, ethanol solution extraction is added in and collects extracting solution；
(2) extracting solution removes insoluble matter after adding in ethyl alcohol solubilising, obtains supernatant；
(3) supernatant that step (2) obtains is taken first to elute 5 column volumes through macroporous resin column with 30% alcohol-water, obtain
To fraction 1；5 column volumes are eluted with 50% alcohol-water again, are concentrated, it is dry, obtain fraction 2；Fraction 2 is taken through 200-300 purposes
Silica gel column chromatography, with the mixed solution of dichloromethane and methanol successively by volume 20:1、10:1、5:1、2:1 gradient elution, often
A 4 column volumes of gradient elution, are obtained 16 fractions；It is 10 to take the volume ratio of carbon dichloride and methanol:4 streams of 1 elution
Part, merge, through gel filtration chromatography, 12 fractions are afforded with methanol, fraction 6-9 is taken to merge, then through ODS mesolow column layers
Analysis, with the mixed solution of first alcohol and water successively by volume 1:9、3:7、4:6、5:5、7:3、1:0 elution, obtains 5 fractions；It takes
The mixeding liquid volume ratio of first alcohol and water is 7:3 fractions afforded, with preparative high-performance liquid chromatographic, chromatographic condition is：ODS colors
Compose column, methanol-water 55:45 be mobile phase, retention time 33min, isolated pure compound.
Wherein, preferably, the ethanol water that the ethanol solution described in step (1) is 5%-95%.More preferably
70% ethanol water.
Preferably, the extracting method described in preparation method of the present invention is cold-maceration, percolation, Microwave Extraction
Method, ultrasonic extraction, reflux extraction or continuous circumfluence extraction method.
Preferably, described in step (1) being extracted as extraction three times, when extraction time is respectively 3 small, 2 it is small when, 2 it is small when.
Extracting solution filtering after Sabia parviflora Wall.ex Roxb extraction, merges extracting solution, is concentrated under reduced pressure into no alcohol taste, obtains extract.
Preferably, step (2) the ethyl alcohol solubilising that adds in makes extract alcohol content dense up to 5%-50% for addition ethyl alcohol
Spend the solution of scope.More preferably make extract alcohol content up to the solution of 20% concentration range.
Preferably, macroreticular resin described in step (3) is AB-8, D101, HP-20, XAD-4, HPD100, DM301,
HPD400 type resins.
Preferably, the supernatant is 1 with resin volume ratio:2.
Experiment shows that triacylglycerol contains in liver cell caused by compound can significantly reduce aliphatic acid shown in formula I
Amount, caspase3 vigor raise MDA contents, reduce hepatocellular apoptosis rate.Therefore the present invention provides compounds shown in Formulas I to exist
Prepare the application in the drug for the treatment of nonalcoholic fatty liver damage.
Preferably, the nonalcoholic fatty liver damage is hepatic injury caused by aliphatic acid.
The present invention also provides a kind of pharmaceutical preparations, including compound shown in the Formulas I of therapeutically effective amount and its pharmaceutically may be used
The carrier of receiving.
Those skilled in the art can prepare the direct or indirect addition of compound shown in the Formulas I required during different dosage forms
Pharmaceutically acceptable various common auxiliary materials, such as filler, disintegrant, lubricant, adhesive, with traditional drug formulations side
Common oral formulations or ejection preparation is made in method.
Preferably, the oral formulations are tablet, capsule, granule, fat emulsion, micro-capsule, dripping pill.
Preferably, the ejection preparation is parenteral solution or powder-injection.
As shown from the above technical solution, the present invention provides a kind of compound in Sabia parviflora Wall.ex Roxb and preparation method thereof with
Using.The compound its for 2- methyl -2,3- dihydroxymethyl -4,5- dihydroxy -6- (3- methyl -3- hydroxyl-1-butenes base) -
1H- 1-Indanones.The preparation method of compound of the present invention is easy to operate, can separate and obtain pure compound.Test table
Bright, triacylglycerol content, caspase3 vigor in liver cell caused by compound of the present invention can significantly reduce aliphatic acid rise
High MDA contents reduce hepatocellular apoptosis rate, can be used for preventing nonalcoholic fatty liver damage.Therefore the present invention provides institutes
State application of the compound in the drug for preparing treatment nonalcoholic fatty liver damage.
Specific embodiment
The invention discloses a kind of compounds in Sabia parviflora Wall.ex Roxb and preparation method and application.Those skilled in the art
Present disclosure can be used for reference, is suitably modified technological parameter realization.In particular, it should be pointed out that all similar substitutions and modifications pair
It is it will be apparent that they are considered as being included in the present invention for those skilled in the art.The method and product of the present invention is
Be described through passing through preferred embodiment, related personnel substantially can not depart from present invention, in spirit and scope to this
Method described in text is modified or suitably changes with combining, to realize and using the technology of the present invention.
For a further understanding of the present invention, below in conjunction with the embodiment of the present invention, to the technical side in the embodiment of the present invention
Case is clearly and completely described, it is clear that described embodiment is only part of the embodiment of the present invention rather than whole
Embodiment.Based on the embodiments of the present invention, those of ordinary skill in the art institute without making creative work
The every other embodiment obtained, belongs to the scope of protection of the invention.
Unless otherwise specified, reagent involved in the embodiment of the present invention is commercial product, can pass through business canal
Road purchase obtains.
The preparation method of noval chemical compound in embodiment 1, Sabia parviflora Wall.ex Roxb
(1) take dry Sabia parviflora Wall.ex Roxb medicinal material, add in 70% ethyl alcohol of concentration of 12 times of amounts, refluxing extraction three times, the time
Respectively 3 it is small when, 2 it is small when, 2 it is small when, filtering, merge extracting solution, be concentrated under reduced pressure into no alcohol taste, obtain extract；
(2) extract of step (1) is taken, which to add in ethyl alcohol, makes alcohol content be 20%, removes insoluble matter with centrifuge, obtains
To supernatant.
(3) supernatant that step (2) obtains is taken to adsorb (medicinal material through HP-20 types macroporous resin column:Resin=1:2 absorption),
5 column volumes first are eluted with 30% alcohol-water, obtain fraction 1；5 column volumes are eluted with 50% alcohol-water again, are concentrated, are done
It is dry, obtain fraction 2.Silica gel column chromatography of the fraction 2 through 200-300 mesh is taken, is pressed successively with the mixed solution of dichloromethane and methanol
Volume ratio 20:1、10:1、5:1、2:1 gradient elution, each 4 column volumes of gradient elution, is obtained 16 fractions；Take dichloride
The volume ratio of carbon and methanol is 10:4 fractions of 1 elution, merge, through gel filtration chromatography, 12 fractions are afforded with methanol,
Fraction 6-9 is taken to merge, then through ODS mesolow column chromatographies, with the mixed solution of first alcohol and water successively by volume 1:9、3:7、1:
1、7:3、1:0 (pure methanol) elutes, and obtains 5 fractions；The mixeding liquid volume ratio for taking first alcohol and water is 7:3 streams afforded
Part, with preparative high-performance liquid chromatographic, chromatographic condition is：ODS chromatographic columns, methanol-water 55:45 be mobile phase, and retention time is
33min, isolated pure compound.(yield 499mg, purity 99.5%).
The structure elucidation of compound：Mainly using spectroscopy techniques, including ultraviolet, infrared, mass spectrum, nuclear magnetic resonance (1H-
NMR, 13C-NMR, 2D-NMR) identify its structure, spectral data and resolving are as follows：
Its spectral data and resolving are as follows：
(1) white amorphous powder, high resolution mass spec ESI-TOF-MS：321.1342[M-H]-.Determine that molecular formula is
C17H22O6, δ in H NMR spectroscopyC:209 (C-1) show that there are carbonyls in structure；δC:14.5,26.9,27.0, δH:1.01,1.37,
1.38 (each 3H, s) be three methyl signals, δC:129.0,141.3,143.0,148.8,121.5,112.1,δH:6.83
(1H, s), showing structure, there are one five substituted benzene rings, δC:122.2(C-11),131.33(C-12),δH:5.69 (1H, d, J=
10.0Hz, H-11), 6.31 (1H, d, J=10.0Hz, H-12), showing structure, there are one cis-double bonds.Then in conjunction with HMBC,
The two dimensional NMRs spectral data such as HSQC, determines the final structure of compound, structural formula shown in formula I, the entitled 2- first of chemistry
Base -2,3- dihydroxymethyl -4,5- dihydroxy -6- (3- methyl -3- hydroxyl-1-butenes base) -1H- 1-Indanones.
Spectral data is as follows：
1HNMR(600MHz,CD3OD)δ:1.01,1.37,1.38 (each, 3H, s ,-CH3), 3.49 (1H, dd, J=7.5,
5.0Hz, H-3), 3.86 (1H, dd, J=7.3,10.4Hz, H-10a), 3.93 (1H, dd, J=5.2,10.4Hz, H-10b),
5.69 (1H, d, J=10.0Hz, H-11), 6.31 (1H, d, J=10.0Hz H-12), 6.83 (1H, s, H-7)；
13CNMR(150MHz,CD3OD):209(C-1),129(C-1a),45.8(C-2),54(C-3),141.3(C-3a),
143(C-4),146.8(C-5),121.5(C-6),112.1(C-7),14.5(C-8),67.3(C-9),61(C-10),131.3
(C-11),122.2(C-12),77.7(C-13),26.9,27.0(C-14,15)。
Embodiment 2, effect experiment research
First, experiment material and animal
1. drug and reagent
Human normal hepatocyte strain L-02 cells (Shanghai Hui Ying bio tech ltd), hyclone (Hangzhou Chinese holly
Biological engineering material Co., Ltd), RPMI Medium1640 culture mediums (Solarbio companies), oleic acid (OA, O7501), palm
Sour (PA, P9767) is purchased from SIGMA companies, biochemistry detection kit (Co., Ltd of Bioengineering Research Institute is built up in Nanjing), pancreas
Enzyme-EDTA digestive juices (Solarbio companies).
2. laboratory apparatus
Inverted microscope (Olympus-ckx41), Biohazard Safety Equipment (HealForce), AL204 type electronic analytical balances
(Mettler Toledo instruments (Shanghai) Co., Ltd.), (Hangzhou is difficult to understand to contain the limited public affairs of instrument to MTV-100 type multitube whirlpools mixed instrument
Department).
3. test medicine and processing method
The compound that Example 1 is prepared adds DMSO to be diluted to the solution that concentration is 0.1mmol/ml.
2nd, experimental method
1. cell culture
1640 culture medium of the L-02 cells containing 5% hyclone, in 37 DEG C, containing 5%CO2Incubator in cultivate
48h is used to test when cell 70%~80% merges.
The compound processing cell that 2.FFAs mixtures (free fatty acid mixture) and embodiment 1 are prepared
Oleic acid or palmitic acid are dissolved in isopropanol, are prepared as the storing liquid of 500mmol/L.By cell inoculation in 96 holes
In plate, per about 5000, hole cell, culture for 24 hours, sucks old culture medium, cell then is randomly divided into 5 groups：Blank group, mould
Type group (250mmol/L FFAs, oleic acid: palmitic acid=2: 1), and administration group (high, medium and low dosage), every group of 6 multiple holes, blank group
Add 100 μ l fresh mediums (1640 culture medium containing 5% hyclone), model group and administration group add in 100 μ l and contain
The culture solution of 250mmol/L FFAs continues culture for 24 hours, sucks culture solution, blank group and model group add the new cultures of 100 μ l
Liquid is administered high, medium and low dosage group and is separately added into the compound that the embodiment 1 that 100 μ l contain 15,30,60 μm of ol/L is prepared
Culture solution, continue culture for 24 hours.
3. Biochemical Indexes
Each processing group cell, histocyte enzymatic assays liver cell triacylglycerol content are collected, barbital acid system measures liver
Cell malonaldehyde (malondialdehyde, MDA) content, spectrophotometer method measure liver cell caspase-3
(casepase3) vigor.Concrete operation step is carried out by kit specification.
4. hepatocellular apoptosis detects
Cell adds in 10 μ lMTT (5mg/ml) per hole after last culture for 24 hours, continues after cultivating 4h, sucks culture solution, add
Enter 150 μ l DMSO, the absorbance under 490n is measured with microplate reader.
5. statistical method
Experimental data withIt represents, carrying out t inspections using 19.0 statistical softwares of SPSS compares, P<0.05 is to have statistics
Learn meaning.
3rd, experimental result
1. the compound that embodiment 1 is prepared is horizontal to triacylglycerol content, caspase3 vigor, MDA in liver cell
Influence, the results are shown in Table 1.
Influence of the table 1 to triacylglycerol content, caspase3 vigor, MDA levels in liver cell
| Group | Triacylglycerol (μm ol/L protein) | Caspase3 vigor (U/g protein) | MDA(mg/g) |
| Blank group | 41.6±6.3 | 2.60±0.45 | 0.91±0.02 |
| Model group | 301.2±53.0 | 5.35±0.54 | 0.58±0.05 |
| Administration group (low) | 253.1±45.3* | 5.01±0.44* | 0.66±0.04* |
| Administration group (in) | 223.1±42.2* | 4.85±0.49* | 0.73±0.04* |
| Administration group (height) | 183.7±41.7* | 4.35±0.41* | 0.81±0.05* |
Note：* represent compared with model group, significant difference (* P<0.05)
The results show that compared with model group, administration group can be substantially reduced triacylglycerol content and caspase3 vigor, together
Shi Shenggao MDA are horizontal.
2. influence of the compound that embodiment 1 is prepared to hepatocellular apoptosis, the results are shown in Table 1.
Influence of the table 2 to hepatocellular apoptosis rate
| Group | Apoptosis rate % |
| Blank group | 0 |
| Model group | 45.3 |
| Administration group (low) | 38.2* |
| Administration group (in) | 32.6* |
| Administration group (height) | 28.1* |
Note：* represent compared with model group, significant difference (* P<0.05)
The results show that compared with model group, administration group is substantially reduced apoptosis rate.
Above the experimental results showed that, caused by the compound that the embodiment of the present invention 1 is prepared can significantly reduce aliphatic acid
Triacylglycerol content, caspase3 vigor in liver cell raise MDA contents, reduce hepatocellular apoptosis rate.Therefore, can develop
As for prevent nonalcoholic fatty liver damage drug or health products.
Claims (10)
1. a kind of compound is 2- methyl -2,3- dihydroxymethyl -4,5- dihydroxy -6- (3- methyl -3- hydroxyl-1-butenes
Base) -1H- 1-Indanones, structural formula shown in formula I,
2. the preparation method of compound described in claim 1, which is characterized in that comprise the following steps：
(1) Sabia parviflora Wall.ex Roxb is taken, ethanol solution extraction is added in and collects extracting solution；
(2) extracting solution removes insoluble matter after adding in ethyl alcohol solubilising, obtains supernatant；
(3) supernatant that step (2) obtains is taken first to elute 5 column volumes through macroporous resin column with 30% alcohol-water, flowed
Part 1；5 column volumes are eluted with 50% alcohol-water again, are concentrated, it is dry, obtain fraction 2；Take silica gel of the fraction 2 through 200-300 mesh
Column chromatography, with the mixed solution of dichloromethane and methanol successively by volume 20:1、10:1、5:1、2:1 gradient elution, Mei Geti
Degree 4 column volumes of elution, are obtained 16 fractions；It is 10 to take the volume ratio of carbon dichloride and methanol:4 fractions of 1 elution, are closed
And through gel filtration chromatography, 12 fractions are afforded with methanol, fraction 6-9 is taken to merge, then through ODS mesolow column chromatographies, uses first
The mixed solution of alcohol and water successively by volume 1:9、3:7、4:6、5:5、7:3、1:0 elution, obtains 5 fractions；Take methanol and
The mixeding liquid volume ratio of water is 7:3 fractions afforded, with preparative high-performance liquid chromatographic, chromatographic condition is：ODS chromatographic columns,
Methanol-water 55:45 be mobile phase, retention time 33min, isolated pure compound.
3. preparation method according to claim 2, which is characterized in that the ethanol solution described in step (1) is 5%-95%
Ethanol water；The extracting method for cold-maceration, percolation, microwave loss mechanisms, ultrasonic extraction, reflux extraction or
Continuous circumfluence extraction method.
4. preparation method according to claim 2, which is characterized in that be extracted as extraction three times described in step (1), extraction
When time is respectively 3 small, 2 it is small when, 2 it is small when.
5. preparation method according to claim 2, which is characterized in that step (2) is described to add in ethyl alcohol solubilising to add in second
Alcohol makes extract alcohol content up to the solution of 5%-50% concentration ranges.
6. preparation method according to claim 2, which is characterized in that macroreticular resin described in step (3) is AB-8,
D101, HP-20, XAD-4, HPD100, DM301, HPD400 type resin；The supernatant is 1 with resin volume ratio:2.
7. application of the compound described in claim 1 in the drug for preparing treatment nonalcoholic fatty liver damage.
It 8. applies according to claim 1, which is characterized in that the nonalcoholic fatty liver damage is liver caused by aliphatic acid
Damage.
9. a kind of pharmaceutical preparation, it is characterised in that：Compound described in claim 1 including therapeutically effective amount and its pharmaceutically may be used
The carrier of receiving.
10. pharmaceutical preparation according to claim 9, which is characterized in that it is oral formulations or ejection preparation.
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| CN113563172A (en) * | 2021-09-23 | 2021-10-29 | 江西中医药大学 | Azulene compound and preparation method and application thereof |
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|---|---|---|---|---|
| CN106631747A (en) * | 2017-02-08 | 2017-05-10 | 江西本草天工科技有限责任公司 | Application of novel compound in preparation of liver protection drugs or health care products |
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| CN106631747A (en) * | 2017-02-08 | 2017-05-10 | 江西本草天工科技有限责任公司 | Application of novel compound in preparation of liver protection drugs or health care products |
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| CN113563172A (en) * | 2021-09-23 | 2021-10-29 | 江西中医药大学 | Azulene compound and preparation method and application thereof |
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Address after: 330004 Jiangxi city of Nanchang province Wanli District Hing Wan Road No. 818 Applicant after: JIANGXI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE Applicant after: Bencao Tian'gong Science & Tech. Co., Ltd., Jiangxi Address before: 330006 No. 56 Yangming Road, East Lake District, Jiangxi, Nanchang Applicant before: Bencao Tian'gong Science & Tech. Co., Ltd., Jiangxi Applicant before: JIANGXI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE |
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