CN107669665A - The metoxyphenol of 5 amyl group 3 is in the application for preparing oxidative stress or inflammatory reaction induces an illness in preventing and treating product - Google Patents
The metoxyphenol of 5 amyl group 3 is in the application for preparing oxidative stress or inflammatory reaction induces an illness in preventing and treating product Download PDFInfo
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/075—Ethers or acetals
- A61K31/085—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/347—Phenols
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
Abstract
The invention discloses the metoxyphenol of 5 amyl group 3 in the application for preparing oxidative stress or inflammatory reaction induces an illness in preventing and treating product.The chemical formula of the metoxyphenol of 5 amyl group 3 is：The metoxyphenol of 5 amyl group 3 is a kind of Nrf2 signal paths activator and NF κ B signal pathway inhibitors.The metoxyphenol of 5 amyl group 3 can raise Nrf2 and its II phases detoxification enzyme NQO1 and antioxidase GCLM protein levels of regulation and control; increase endogenous antioxidant glutathione level; suppress the generation of the active oxygen of external source poisonous substance induction, pulmonary branches tracheal epithelial cell, glomerulus membrane system cell, human nerve cell and the human breast cancer cell oxidative damage that exogenous poisonous substance induces have protective effect.The metoxyphenol of 5 amyl group 3 lowers inflammation gene expression expression, the mouse macrophage RAW264.7 inflammatory reactions to LPS inductions are inhibited to that can suppress NF κ B signal Pathway Activations.
Description
Technical field
The present invention relates to field of medicaments is belonged to, it is related to the application of oxidation phenolic compound, and in particular to 5- amyl group -3- methoxies
Base-phenol answering in preparation prevention or treatment oxidative stress or inflammatory reaction induce an illness medicine, health products or cosmetics
With.
Background technology
The fast development of society, causes environmental pollution to increasingly sharpen.A variety of environmental contaminants, as carbon sulphur nitrogen oxides (CO,
SO2、NO2Deng), heavy metal (lead, chromium, arsenic etc.), building Mineral Dust formed haze；Water source is dirty caused by industry and sanitary sewage
Dye and soil pollution, and grain contamination caused by entering etc., exogenous pollution thing slowly attacks human tissue organ, causes
Oxidative stress.Then, body tissue generates a large amount of lipid peroxidation products and excessive endogeneous activity oxygen, and the two is by acting on
After birth, protein and DNA cause cellular damage.Excessive endogeneous activity oxygen will also induction inflammation nuclear factor (Nuclear
Factor, NF)-kB activation, cause downstream inflammatory factor TNF-α, IL-6 and IL-1 β largely to produce.Increase release inflammation because
Sub- positive feedback adjusts endogeneous activity oxygen, further activates NF- κ B, oxidative stress is formed spiral formula with inflammatory reaction
Vicious circle, so as to induce a series of serious diseases, such as cancer, nerve degenerative diseases, angiocardiopathy, diabetes and chronic
Obstructive lung disease etc..Therefore, anti-oxidant, the anti-inflammatory power of body are strengthened, to preventing and treating what is triggered by oxidative stress and chronic inflammation
It is diseases related significant.
Nuclear factor Nrf2 (Nuclear factor-erythroid 2-related factor 2) signal path is
Regulate and control the critical path of human body oxidative stress, be the target spot of chemopreventive agent (medicine) effect.Nrf2 is to adjust cellular oxidation also
Yuanping City weighing apparatus important transcription factor, by with antioxidase and II phase detoxication enzyme promoter region Antioxidation reaction original papers (ARE)
With reference to regulating cell redox equilibrium, II phase detoxication enzyme of its target gene including encoding GST, UGT, NQO1, and GCLM,
The endogenous anti-oxidative albumen such as HO-1.NF- κ B signal paths are the critical paths for regulating and controlling human body inflammatory reaction, are to suppress inflammation
The useful effect target spot of reaction.NF- κ B are the important transcription factors for adjusting cellular inflammation reaction, by being combined with κ B sequences, are adjusted
Control the expression of inflammation-related gene.These inflammation gene expressions include inflammatory factor (tumor necrosis factor α (TNF-α), Interleukin -1β
(IL-1 β)), chemotactic factor (CF), (cyclooxygenase-2 (COX-2), is lured for adhesion molecule (such as CD62L) and inflammation related proteins
Conductivity type nitricoxide synthase (iNOS)).Therefore, activate the defense mechanism of Nrf2 mediations and suppress the inflammatory reaction of NF- κ B regulation and control,
It is the available strategy to anti-oxidation stress and inflammatory reaction.
Oxidative stress and inflammation damnification state caused by pollutant are tackled, human body device is raised using exogenous Nrf2 activators
Official and tissue Nrf2 are horizontal, can strengthen body self-defense ability, suppress NF- κ B signal signal pathway activateds, chronic for preventing
The generation of obstructive disease of lung, chronic kidney disease, respiratory inflammation, diabetes, nerve degenerative diseases and tumor disease has weight
Want meaning.Nrf2 signal paths are activated, II phases can be raised and detoxified enzyme level, clearing the pollution off middle carcinogenic substance or reduces its poison
Property, suppress DNA damage, the gene mutation of carcinogenic substance induction, so as to the generation of pre- preventing tumor.Raise Nrf2 expression, by increasing capacitance it is possible to increase
Glutathione levels, strengthen activities of antioxidant enzymes, suppress cytolipin peroxidating, active oxygen in scavenger-cell, lower
NF- kB activations and the secretion of downstream inflammatory factor, protect body from the harm of environmental contaminants, reduce COPD
The incidence of disease of the diseases such as disease, chronic kidney disease, respiratory inflammation, diabetes, nerve degenerative diseases.
Natural products is the important sources of lead compound, and significant contribution is made that to human medicine development history.Mesh
Before, many clinical applications are for natural products or from natural products, such as qinghaosu, taxol, ET743 etc., from natural production
The lead compound with preventive and therapeutic action is found in thing, is the important channel of medicament research and development.Wherein, invention of the invention
People has found that litsea martabanica extract has Nrf2 agonisms and NF- κ B inhibitory action first, and having, which turns into preventing and treating oxidation, answers
Swash the potentiality for the medicine that induces an illness.Litsea martabanica chemical constitution study is less, and does not have document in litsea martabanica
Chemical composition bioactivity is evaluated.
The content of the invention
In order to solve the deficiencies in the prior art, an object of the present invention is to provide 5- amyl group -3- methoxy-phenols and made
Induce an illness the application prevented and treated in product for oxidative stress or inflammatory reaction, can prevent or treat COPD,
Chronic kidney disease, respiratory inflammation, diabetes, nerve degenerative diseases and tumor disease.
To achieve these goals, the technical scheme is that：
5- amyl group -3- methoxy-phenols in the application for preparing oxidative stress or inflammatory reaction induces an illness in preventing and treating product,
The chemical formula of the 5- amyl groups -3- methoxy-phenols is：
The present inventor has found 5- amyl group -3- methoxy-phenols by studying, protein stabilized by increasing Nrf2
Property, suppress Nrf2 protein degradations, raise Nrf2 and its II phases detoxification enzyme NQO1 and antioxidase GCLM protein levels of regulation and control,
Suppress the generation of the excessive cell endogeneous activity oxygen of arsenic induction；NF- κ B activation can be suppressed, inflammation gene expression expression is lowered, protect
Protect harm of the body from environmental contaminants.To confirm the anti-oxidant anti-inflammatory power of 5- amyl group -3- methoxy-phenols, adopt first
The pulmonary branches tracheal epithelium Beas-2B cellular damage models induced with arsenic, have rated 5- amyl group -3- methoxy-phenols to anti-oxidant
The ability of damage, the results showed that the compound can increase endogenous cellular antioxidant agent GSH levels, suppress arsenic induction Beas-
2B cellular damages and apoptosis；In addition 5- amyl groups -3- methoxy-phenols are to glomerulus membrane system cell SV40MES13 cells, people's nerve
SHSY5Y cells and human breast carcinoma MDA-MB-231 cells also show protective effect.Then, the mouse macrophage induced using LPS
Cell RAW264.7 inflammatory models, it have rated the antiinflammatory action of 5- amyl group -3- methoxy-phenols, the results showed that, the compound energy
It is enough to suppress protein I κ B alpha levels by raising NF- κ B and suppress NF- κ B subunits p65 activation, reduce inflammatory mediator TNF-α, IL-1 β and
Inflammation related proteins iNOS, COX-2 are horizontal, lower Cellular inflammatory reaction.Thus, it was therefore concluded that, 5- amyl groups of the present invention-
3- methoxy-phenols can have preventing and treating COPD, breathing to anti-oxidation stress, and can to anti-inflammatory response
Road inflammation, cutaneous lesions, diabetes, the potentiality of nerve degenerative diseases and tumour.
The second object of the present invention is to provide a kind of pharmaceutical composition for realizing above-mentioned application, and active principle includes 5- penta
Base -3- methoxy-phenols.
The third object of the present invention is to provide a kind of medicament for realizing above-mentioned application, including 5- amyl group -3- methoxy-phenols
And auxiliary material.
The fourth object of the present invention is to provide a kind of preparation method of above-mentioned medicament, by 5- amyl group -3- methoxy-phenols,
Sieved after starch and dextrin mixing, add sodium carboxymethylcellulose granulation, then added tabletting after magnesium stearate mixes and produce
Tablet；Or, carbomer and polysorbate are added into water and are well mixed, it is equal to add the mixing of 5- amyl group -3- methoxy-phenols
It is even to produce gel.
The fifth object of the present invention is to provide a kind of cosmetics for realizing above-mentioned application, including above-mentioned 5- amyl groups -3- methoxies
Base-phenol and cosmetic material.
Beneficial effects of the present invention are：
The present inventor has found that 5- amyl group -3- methoxy-phenols can raise Nrf2 and its regulation and control by studying
II phases detoxification enzyme NQO1 and antioxidase GCLM protein levels, suppress the generation of the excessive endogeneous activity oxygen of arsenic induction, and it swashs
Mechanism living is to suppress the realization of Nrf2 protein degradations by increasing Nrf2 protein stabilities；Meanwhile the excess for lowering arsenic induction is endogenous
Property active oxygen, moreover it is possible to weaken NF- κ B signal Pathway Activations, lower inflammation gene expression expression, protect body from environmental contaminants
Harm.To confirm the anti-oxidant anti-inflammatory power of 5- amyl group -3- methoxy-phenols, the pulmonary branches tracheal epithelium induced first using arsenic
Beas-2B cellular damage models, it have rated ability of the 5- amyl group -3- methoxy-phenols to anti-oxidative damage, the results showed that the change
Compound can increase endogenous cellular antioxidant agent GSH levels, suppress arsenic induction Beas-2B cellular damages and apoptosis；In addition 5-
Amyl group -3- methoxy-phenols are to glomerulus membrane system cell SV40MES13 cells, people's nerve SHSY5Y cells and human breast carcinoma
MDA-MB-231 cells also show protective effect.Then, the mouse macrophage RAW264.7 inflammation moulds induced using LPS
Type, it have rated the antiinflammatory action of 5- amyl group -3- methoxy-phenols, the results showed that, the compound can be by raising NF- κ B suppressions
Protein I κ B alpha levels processed suppress NF- κ B subunits p65 activation, reduce inflammatory mediator TNF-α, IL-1 β and inflammation related proteins
INOS, COX-2 are horizontal, lower Cellular inflammatory reaction, have antiinflammatory action.
Brief description of the drawings
The Figure of description for forming the part of the application is used for providing further understanding of the present application, and the application's shows
Meaning property embodiment and its illustrate be used for explain the application, do not form the improper restriction to the application.
Fig. 1：The block diagram tested for NQO1 induced activity, shows that 5- amyl group -3- methoxy-phenols can induce hepa
1c1c7 cell II phase detoxication enzymes NQO1 expression simultaneously strengthens its activity, the 5- amyl group -3- methoxy-phenol concentration units in figure
For μM, 2.0 μM of sulforaphen is positive control；
Fig. 2 is the immunoblotting assay figure of various concentrations 5- amyl group -3- methoxy-phenols, shows 5- amyl group -3- methoxies
Base-phenol can raise Nrf2 and anti-oxidant GCLM with II phases downstream and detoxify zymoprotein NQO1 protein levels, the 5- penta in figure
Base -3- methoxy-phenols concentration unit is μM；
Fig. 3 is the fluorescence micrograph of cellular immunity, shows that 5- amyl group -3- methoxy-phenols can promote Nrf2 indexable
Enter core 5- amyl group -3- methoxy-phenols concentration for 25 μM；
Fig. 4 is the immunoblotting assay figure of different time 5- amyl group -3- methoxy-phenols, shows 5- amyl group -3- methoxies
Base-phenol can extend Nrf2 protein half-lifes, and 5- amyl group -3- methoxy-phenols concentration is 25 μM in figure；
Fig. 5 is the block diagram of influence of the different material to glutathione, shows that 5- amyl group -3- methoxy-phenols can increase
Add human bronchial epithelial Beas-2B endogenous cellular antioxidant agent glutathione levels, 2.5 μM of sulforaphen is positive right in figure
According to 5- amyl group -3- methoxy-phenols concentration unit is μM；
Fig. 6 is endogenous cellular active oxygen fluorescence photo, shows that 5- amyl group -3- methoxy-phenols can suppress in excess
The generation of source property active oxygen, in figure didox100 μM be positive control 5- amyl group -3- methoxy-phenols concentration unit for μM；
Fig. 7 is the block diagram of the cell survival amount of cell toxicity test, shows that 5- amyl group -3- methoxy-phenols can press down
The cytotoxicity of arsenic induction processed, figure is protection of the various concentrations 5- amyl group -3- methoxy-phenols to 6 μM of arsenic inducing cytotoxics
Effect.
Fig. 8 is the fluorescence micrograph of natural death of cerebral cells, and AO/EB dyeing shows that 5- amyl group -3- methoxy-phenols can suppress
The Apoptosis of arsenic induction, 5- amyl group -3- methoxy-phenols concentration are 12.5 μM, and the concentration of arsenic is 6 μM.
Fig. 9 is that NO generations suppress analysis of experiments figure, shows that 5- amyl group -3- methoxy-phenols can press down under non-toxic
NO generation in the RAW264.7 cells of LPS inductions processed.5- amyl group -3- methoxy-phenols concentration unit in figure for μM, LPS
Concentration is 1 μ g/mL；
Figure 10 is the immunoblotting assay figure of various concentrations 5- amyl group -3- methoxy-phenols, shows 5- amyl group -3- methoxies
Base-phenol can raise the expression that NF- κ B suppress protein I κ B α, reduce NF- κ B subunits p65 and downstream inflammation related proteins
INOS, COX-2 protein level, 5- amyl group -3- methoxy-phenols concentration unit in figure for μM；LPS concentration is 1 μ g/ml；
100 μM of didox is positive control；
Figure 11 is the fluorescence micrograph of cellular immunity, shows that 5- amyl group -3- methoxy-phenols can suppress LPS inductions
NF- κ B subunit p65 indexings enter core；5- amyl group -3- methoxy-phenols concentration is 25 μM；LPS concentration is 1 μ g/mL；didox
100 μM are positive control；
Figure 12 is the ELISA figure of various concentrations 5- amyl group -3- methoxy-phenols, shows 5- amyl group -3- methoxies
Base-phenol can lower the inflammatory mediator TNF-α of LPS inductions, and IL-1 β are horizontal, and the 5- amyl group -3- methoxy-phenols in figure are dense
It is μM to spend unit；LPS concentration is 1 μ g/mL；100 μM of didox is positive control.
Embodiment
It is noted that described further below is all exemplary, it is intended to provides further instruction to the application.It is unless another
Indicate, all technologies used herein and scientific terminology are with usual with the application person of an ordinary skill in the technical field
The identical meanings of understanding.
It should be noted that term used herein above is merely to describe embodiment, and be not intended to restricted root
According to the illustrative embodiments of the application.As used herein, unless the context clearly indicates otherwise, otherwise singulative
It is also intended to include plural form, additionally, it should be understood that, when in this manual using term "comprising" and/or " bag
Include " when, it indicates existing characteristics, step, operation, device, component and/or combinations thereof.
As background technology is introduced, exist in the prior art it is less to litsea martabanica chemical constitution study, not
There are the deficiency that document carries out Activity determination to the chemical composition in litsea martabanica, in order to solve technical problem as above, this Shen
5- amyl group -3- methoxy-phenols please be propose in the application for preparing oxidative stress or inflammatory reaction induces an illness in preventing and treating product.
A kind of exemplary embodiment of the application, there is provided 5- amyl group -3- methoxy-phenols are preparing oxidative stress or inflammation
Disease reacts the application in the preventing and treating product that induces an illness, and the chemical formula of the 5- amyl groups -3- methoxy-phenols is：
The application is by studying the II phase detoxifications for finding that 5- amyl group -3- methoxy-phenols can raise Nrf2 and its regulation and control
Enzyme NQO1 and antioxidase GCLM protein levels, suppress the generation of the excessive endogeneous activity oxygen of arsenic induction, and its activation mechanism is
Suppress the realization of Nrf2 protein degradations by increasing Nrf2 protein stabilities；Meanwhile the excessive endogeneous activity oxygen of arsenic induction is lowered,
NF- κ B signal Pathway Activations can also be weakened, inflammation gene expression expression is lowered, protects body from the harm of environmental contaminants.To be true
The anti-oxidant anti-inflammatory power of 5- amyl group -3- methoxy-phenols is demonstrate,proved, the pulmonary branches tracheal epithelium Beas-2B induced first using arsenic is thin
Cellular damage model, it have rated ability of the 5- amyl group -3- methoxy-phenols to anti-oxidative damage, the results showed that the compound can
It is horizontal to increase endogenous cellular antioxidant agent GSH, suppresses arsenic induction Beas-2B cellular damages and apoptosis；In addition 5- amyl groups -3-
Methoxy-phenol is to glomerulus membrane system cell SV40MES13 cells, people's nerve SHSY5Y cells and human breast carcinoma MDA-MB-
231 cells also show protective effect.Then, the mouse macrophage RAW264.7 inflammatory models induced using LPS, have rated
The antiinflammatory action of 5- amyl group -3- methoxy-phenols, the results showed that, the compound can suppress protein I κ B by raising NF- κ B
Alpha levels suppress NF- κ B subunits p65 activation, reduce inflammatory mediator TNF-α, IL-1 β and inflammation related proteins iNOS, COX-2 water
It is flat, Cellular inflammatory reaction is lowered, thus, it was therefore concluded that, 5- amyl groups -3- methoxy-phenols of the present invention can be to antioxygen
Change stress, and can to anti-inflammatory response, have preventing and treating COPD, respiratory inflammation, cutaneous lesions, diabetes,
The potentiality of nerve degenerative diseases and tumour.
Product described herein includes medicine, health products, cosmetics etc..
Preferably, the oxidative stress induces an illness as COPD, respiratory inflammation, cutaneous lesions, sugar
Urine disease, nerve degenerative diseases or tumor disease.
Preferably, the concentration of the 5- amyl groups -3- methoxy-phenols is 6.25~25 μM.Cell is produced under the concentration
More preferable protective effect.It is further preferred that the concentration of the 5- amyl groups -3- methoxy-phenols is 12.5 μM.To thin under the concentration
Born of the same parents produce best protection effect.
5- amyl groups -3- methoxy-phenols described herein can be used and are chemically synthesized, can also be so as in plant
Extraction.The application is preferable, there is provided a kind of method that 5- amyl group -3- methoxy-phenols are always extracted from litsea martabanica, by Yunnan
The ethanol extract of southern Litsea pungens uses petroleum ether extraction, and the part of petroleum ether extraction is used into petroleum ether-ethyl acetate system
Gradient elution, by the 8th part of petroleum ether-ethyl acetate system gradient elution through sephadex lh-20 chromatogram post separation,
The 5th part that sephadex lh-20 chromatogram post separation obtains is separated into obtain 5- by semipreparative performance liquid chromatographic column
Amyl group -3- methoxy-phenols.
5- amyl group -3- methoxy-phenols activation Nrf2 signal paths act on and pollutant are induced cellular damage protection
The research of effect
Using mouse hepa 1c1c7 liver cancer cell lines, 5- amyl group -3- methoxy-phenols are have rated to II phase detoxification enzymes
NQO1 inducing action, the results showed that 5- amyl group -3- methoxy-phenols can strengthen NQO1 activity, i.e. 5- amyl groups -3- methoxies
Base-phenol has the function that to suppress oxidative stress (Fig. 1).
Using the normal pulmonary epithelial cells Beas-2B cells of people, 5- amyl group -3- methoxy-phenols are have rated to cell Nrf2
The effect of signal path.Western blot shows that 5- amyl group -3- methoxy-phenols can raise Nrf2 albumen
Expression, and anti-oxidant GCLM with the II phases in downstream can be promoted to detoxify zymoprotein NQO1 expression (Fig. 2).Cellular immunofluorescence tests table
Bright, 5- amyl group -3- methoxy-phenols can promote Nrf2 indexings to enter core (Fig. 3), extend Nrf2 protein half-lifes, suppress Nrf2
Protein degradation, increase its stability (Fig. 4).
The pulmonary branches tracheal epithelial cell toxic model induced using arsenic, have rated 5- amyl group -3- methoxy-phenols and arsenic is lured
The effect of the excessive endogeneous activity oxygen of guided cell, the results showed that 5- amyl group -3- methoxy-phenols can suppress arsenic inducing cell
The generation of middle excessive endogeneous activity oxygen, i.e. 5- amyl groups -3- methoxy-phenols can suppress oxidative stress (Fig. 6).
The pulmonary branches tracheal epithelial cell toxic model of arsenic induction is selected, it is normal to people to evaluate 5- amyl group -3- methoxy-phenols
Pulmonary epithelial cells Beas-2B protective effect.Research is it has proven convenient that arsenic can increase intracellular reactive oxygen level, induce cell oxygen
Change stress, cause cellular damage and death.As a result show, cell is handled through 5- amyl group -3- methoxy-phenols, it is right at 12.5 μM
Cell produces best protection effect (Fig. 7)；In addition, 5- amyl group -3- methoxy-phenols can suppress the Apoptosis of arsenic induction
(Fig. 8).
Using mouse macrophage RAW264.7 cell lines, 5- amyl group -3- methoxy-phenols are have rated to inflammatory mediator NO
Generation inhibitory action, the results showed that 5- amyl group -3- methoxy-phenols can suppress under non-toxic NO activity, i.e. 5- penta
Base -3- methoxy-phenols have the function that to suppress inflammatory mediator (Fig. 9).
Using mouse macrophage RAW264.7 cell lines, 5- amyl group -3- methoxy-phenols are have rated to cell NF- κ B
The effect of signal path.Western blot shows that 5- amyl group -3- methoxy-phenols can raise NF- κ B and suppress egg
White I κ B alpha levels, lower the expression of NF- κ B subunit p65 albumen, and can suppress downstream inflammation related proteins iNOS and COX-2
Express (Figure 10).Cellular immunofluorescence experiment shows that the NF- κ B that 5- amyl group -3- methoxy-phenols can suppress LPS inductions are sub-
Base p65 indexings enter core (Figure 11).EUSA shows that 5- amyl group -3- methoxy-phenols can lower LPS inductions
Inflammatory factor TNF-α and IL-1 β horizontal (Figure 12), reduce Cellular inflammatory reaction.
The another embodiment of the application, there is provided a kind of pharmaceutical composition for realizing above-mentioned application, active principle bag
Include 5- amyl group -3- methoxy-phenols.
The present invention the third embodiment there is provided a kind of medicament for realizing above-mentioned application, including 5- amyl group -3- methoxies
Base-phenol and auxiliary material.
Preferably, the medicament is capsule, tablet, powder, granule, injection, oral liquid, vina, pill, mixture
Or tincture.
The 4th kind of the application is embodiment there is provided a kind of preparation method of above-mentioned medicament, by 5- amyl group -3- methoxies
Sieved after base-phenol, starch and dextrin mixing, add sodium carboxymethylcellulose granulation, after then adding magnesium stearate mixing
Tabletting produces tablet；Or, carbomer and polysorbate are added into water and are well mixed, add 5- amyl groups -3- methoxyl groups-benzene
Phenol is well mixed to produce gel.
Preferably, 5- amyl groups -3- methoxy-phenols, starch and the dextrin mass ratio are 1~2:2~3:2~3；Or,
The mass ratio of 5- amyl group -3- methoxy-phenols, carbomer and polysorbate is 2~3:3~4:1~2.
The 5th kind of the application embodiment there is provided a kind of cosmetics for realizing above-mentioned application, including above-mentioned 5- amyl groups-
3- methoxy-phenols and cosmetic material.
Preferably, the cosmetics are facial mask, face cream, cold cream, surfactant, skin care powder or skin-care gel.
In order that the technical scheme of the application can clearly be understood by obtaining those skilled in the art, below with reference to tool
The embodiment of body describes the technical scheme of the application in detail.
Embodiment 1：The structural identification of 5- amyl group -3- methoxy-phenols
Litsea martabanica aerial part, ethanol extract is extracted to obtain with 95% ethanol, then successively using petroleum ether, acetic acid
Ethyl ester, extracting n-butyl alcohol.Oil ether moiety uses petroleum ether-ethyl acetate system gradient elution, concentration be respectively pure petroleum ether,
Petroleum ether-ethyl acetate=95：5 (volume ratios), petroleum ether-ethyl acetate=90：10 (volume ratios), petroleum ether-ethyl acetate
=85：15 (volume ratios), petroleum ether-ethyl acetate=80：20 (volume ratios), petroleum ether-ethyl acetate=75：25 (volumes
Than), petroleum ether-ethyl acetate=70：30 (volume ratios), petroleum ether-ethyl acetate=60：40 (volume ratios), petroleum ether-acetic acid
Ethyl ester=50：50 (volume ratios), petroleum ether-ethyl acetate=40：60 (volume ratios), 100% ethyl acetate obtain 14 parts
(Frs.1-14).Fr.8 parts (petroleum ether-ethyl acetate=90：10 elutions) obtained through sephadex lh-20 chromatogram post separation
Six components (Frs.8A-F), Fr.8E separate to obtain 5- amyl group -3- methoxy-phenols through semipreparative performance liquid chromatographic column.
Method：Using DMSO-d6 as solvent, TMS is internal standard, and its hydrogen spectrum and carbon spectrum are determined simultaneously using nuclear magnetic resonance chemical analyser
Carry out structure elucidation.
As a result：The 1H-NMR signals of compound are δ H 6.32 (1H, s, H-), 6.27 (1H, s, H-6), 6.24 (1H, t, J
=2.4 Hz, H-2), 3.76 (3H, s ,-OCH3), 2.51 (2H, t, J=8Hz, H-1 '), 1.55~1.62 (2H, m, H-2 '),
1.26~1.35 (4H, m, H-3 ', 4 '), the 13C NMR signals of 0.89 (3H, t, J=6.8Hz, H-5 ') compound are δ 160.8
(C-3),156.6 (C-1),145.7(C-5),107.9(C-4),106.7(C-6),98.7(C-2),55.2(3-OMe),36.0
(C-1′),31.5(C-2′), 30.8(C-3′),22.5(C-4′),14.0(C-5′).Structural identification is 5- amyl group -3- methoxies
Base-phenol.
Embodiment 2：The NQO1 induced activitys evaluation of 5- amyl group -3- methoxy-phenols
(1) culture of murine hepatocarcinoma cell hepa 1c1c cell lines
Murine hepatocarcinoma cell hepa 1c1c cell lines are purchased from American Type Culture collection warehousing (ATCC), using containing 10%
The MEM culture mediums of hyclone (FBS), are placed in 37 DEG C, 5%CO2Cultivated in incubator.
(2) NQO1 induced activitys are tested
Hepa 1c1c cells are inoculated on 96 orifice plates, the 5- amyl group -3- methoxies of various concentrations are added after cell attachment
Base-phenol (embodiment 1 is confirmed), handle 24 hours, using 0.8% digitonin solution cell lysis, add detection liquid
(1.0mL 0.5M trishydroxymethylaminomethanes-hydrochloric acid (Tris-HCl), 15mg bovine serum albumin(BSA)s, 6mg MTT, 150 μ L are told
Warm -20,150 μ L 150mM D-Glucose -6- phosphoric acid, 15 μ L 7.5mM flavin adenine dinucleotide (FAD)s, 27 μ L 50mM nicotinoyl
Amine adenine-dinucleotide phosphoric acid, 20 μ L 50mM menadiones), place 3 minutes, luminous intensity is determined in 630nm.
As a result：As shown in figure 1,5- amyl group -3- methoxy-phenols can activate NQO1 activity in hepa 1c1c7 cells,
Its maximum induced activity is 3.83 times (100 μM), and positive control medicine sulforaphen (2.0 μM) is 2.98 times of blank control group.
The above results show that 5- amyl group -3- methoxy-phenols can activate II phase detoxification enzymes, have protective effect to human body cell.
Embodiment 3：5- amyl group -3- methoxy-phenols can raise Nrf2, GCLM and NQO1 protein level
Method：The change of protein level in western blot analysis (Western blot) detection cell
Beas-2B cells are inoculated in diameter 35mm culture dishes, cultivated after reaching 70%-80% to density, are added not
Testing compound with concentration handles 16h, and PBS is washed 2 times, adds cell pyrolysis liquid (50 μ g/mL Aprotinins, 0.5mM benzyls
Sulfuryl fluoride, 1mM sodium vanadates, 10mM sodium fluorides, 10mM β-phosphoglycerol), collect albumen and using Bradford methods measure egg
White concentration.Sample protein (100 μ g) loading is respectively taken, SDS-PAGE protein isolates component is simultaneously turned protein band using electrotransfer method
Move on cellulose nitrate film.Film through TBS prepare 5% skimmed milk power solution room temperature closing 1h after, respectively with it is each to be measured
4 DEG C of overnight incubations of protein antibodies.After the secondary antibody incubation 1h of horseradish peroxidase is separately added into after TBS is washed, with increasing
Strong type ECL chemiluminescences carry out analysis of protein.
As a result：As shown in Fig. 2 cell is after 5- amyl group -3- methoxy-phenols handle 16h, Nrf2 and anti-oxidant downstream
With II phases detoxify zymoprotein NQO1 and GCLM protein level present dose dependent increase, Keap1 protein levels are unchanged, card
The real compound can activate Nrf2 signal paths on protein level.
Embodiment 4：5- amyl group -3- methoxy-phenols promote Nrf2 protein translocations to enter core
Method：Immuno-fluorescence assay Nrf2 intracellular locations
Cell climbing sheet is positioned in 24 orifice plates, is inoculated with Beas-2B cells, 5- amyl group -3- first is added after cell attachment
Epoxide-phenol is handled 8 hours, and PBS is washed 2 times, is added methanol and is fixed 4 hours, and PBS is washed 2 times, adds Nrf2 antibody incubations 1
Hour, PBS is washed 3 times, adds DAPI and fluorescence secondary antibody is incubated 50 minutes, using fluorescence microscope and take pictures.
As a result：Immunofluorescence results are shown (Fig. 3), and under cell normal condition, Nrf2 is located in cytoplasm, add 5- penta
After base -3- methoxy-phenols and positive control sulforaphen are handled 8 hours, Nrf2 indexings enter nucleus.
Embodiment 5：5- amyl group -3- methoxy-phenols increase Nrf2 protein stabilities
Method：Western blot analysis detect Nrf2 protein half-lifes
Beas-2B cells are inoculated in diameter 35mm culture dishes, cultivated after reaching 70%-80% to density, add 5-
Amyl group -3- methoxy-phenol 8h, cycloheximide is then added, timing, albumen was collected at 0,10,20,30,40 minute respectively, enters
Row western blot analysis detect, and are quantified using Image J softwares.
As a result：As shown in figure 4, blank group Beas-2B cell Nrf2 protein half-lifes are 19.23 minutes, through 5- amyl groups -3-
After methoxy-phenol processing 8h, Nrf2 protein half-lifes extend to 38.84 minutes, show 5- amyl group -3- methoxy-phenol energy
Enough extend Nrf2 protein half-lifes.
Embodiment 6：5- amyl group -3- methoxy-phenols can increase endogenous cellular antioxidant agent glutathione level
(1) culture of people's normal epidermis Beas-2B cells
People normal lung bronchiolar epithelium Beas-2B cells are purchased from American Type Culture collection warehousing (ATCC), using 1640
Culture medium, and 10% hyclone (FBS) is added thereto, 5% glutamine, 37 DEG C are placed in, 5%CO2Cultivated in incubator.
(2) measure of glutathion inside cell content
Beas-2B cells are inoculated in diameter 35mm culture dishes, cultivated after reaching 70%-80% to density, are added not
5- amyl group -3- methoxy-phenols (embodiment 1 is confirmed) with concentration are handled 24 hours, and PBS is washed 2 times, add 0.5mL 50mM
Sodium phosphate and 1mM edta buffers liquid receive cell, and ultrasonic 1min, 10000g are centrifuged 15 minutes, supernatant are taken, according to glutathione
Kit specification operation is determined, 412nm measure absorbances simultaneously calculate glutathione content.
As a result：As shown in figure 5,5- amyl group -3- methoxy-phenols can dramatically increase glutathione levels, increase
Strong intracellular reducing power.
Embodiment 7：5- amyl group -3- methoxy-phenols can reduce mistake in the human bronchial epithelial Beas-2B cells that arsenic induces
Measure the level of endogeneous activity oxygen
Beas-2B cells are inoculated in diameter 35mm culture dishes, cultivated after reaching 30%-40% to density, add 5-
Amyl group -3- methoxy-phenols handle 8h, then act on 10h altogether with 5 μM of As, and DCFH-DA (10 μM) is added after discarding nutrient solution
30min is incubated, PBS is washed 3 times, using fluorescence microscope and taken pictures.
As a result：As shown in fig. 6,5- amyl group -3- methoxy-phenols can significantly reduce the excessive endogeneous activity of arsenic induction
The level of oxygen, suppressing cellular oxidation stress.
Embodiment 8：The guarantor for the human bronchial epithelial Beas-2B cellular damages that 5- amyl group -3- methoxy-phenols are induced arsenic
Shield acts on
Method：The protective effect for the cytotoxicity that mtt assay measure Chinese medicine composition is induced arsenic
Beas-2B cells are inoculated on 96 orifice plates, after cell attachment, using concentration 5- amyl groups -3- methoxyl groups-benzene to be measured
Phenol pretreatment cell 8 hours, add the arsenic of various concentrations and concentration 5- amyl group -3- methoxy-phenols to be measured (embodiment 1 is confirmed)
Processing 48 hours, or MTT is added after 3 hours, 590nm measure absorbances simultaneously calculate cells survival rate.
As a result：As shown in fig. 7, using 5- amyl group -3- methoxy-phenols pretreatment cell 8 hours, 10 can be significantly inhibited
The cytotoxicity that μM arsenic induces, increase cells survival rate, wherein 12.5 μM of concentration 5- amyl group -3- methoxy-phenols activity are most
It is good.As shown in fig. 7, using 25 μM of concentration 5- amyl group -3- methoxy-phenols as protection medicines, can significantly inhibit 5,10,
The cytotoxicity that 20 μM of arsenic induces, increase cells survival rate.As a result prove, 5- amyl group -3- methoxy-phenols can suppress to cause
The toxicity of cancer thing arsenic induction.
Embodiment 9：5- amyl group -3- methoxy-phenols can suppress the natural death of cerebral cells of arsenic induction
Beas-2B cells are inoculated in 35mm culture dishes, added after adherent 5 μM of arsenic or 25 μM of 5- amyl group -3- methoxyl groups -
Phenol handles 12h, is separately added into acridine orange (AO)/ethidium bromide (EB) and is dyed, and cellular using fluorescence microscope
State.
As a result：As shown in figure 8, using arsenic and/or 5- amyl group -3- methoxy-phenols coprocessing 12 hours, can significantly press down
The Apoptosis of arsenic induction processed.
Embodiment 10：The RAW264.7 that 5- amyl group -3- methoxy-phenols under non-toxic, can suppress LPS inductions is thin
NO generation in born of the same parents.
(1) mouse macrophage RAW264.7 culture
Mouse macrophage RAW264.7 is purchased from American Type Culture collection warehousing (ATCC), using DMEM culture mediums, and
10% hyclone (FBS) is added thereto, 5% glutamine, is placed in 37 DEG C, 5%CO2Cultivated in incubator.
(2) NO generates Inhibition test
RAW264.7 cells are inoculated in 96 hole versions, cultivated after reaching 70%-80% to density, add LPS (1 μ g/mL)
With the testing compound coprocessing cell 18 hours of various concentrations, then, 100 μ L culture supernatants are taken, with isometric Griess
(0.1% naphthodiamide and 1% sulfanilamide (SN) are in 5%H for reagent3PO4In solution) mixing.After being incubated 15 minutes at room temperature, surveyed at 570nm
Absorbance is measured, and passes through NaNO2Standard curve assesses NO contents.
After determining NO contents, CDCC of the extract to the cells of Raw 264.7 is determined using mtt assay.Removing
After above-mentioned 100 μ L of supernatant liquid, 1640 culture mediums that 100 μ L contain 0.4%MTT are added into each hole, incubated cell 3 is small at 37 DEG C
When.Then, medium removed with care, 100 μ L DMSO are added into each hole.After dye crystal dissolving, measured at 570nm
Solution absorbance.
Embodiment 11：5- amyl group -3- methoxy-phenols can raise NF- κ B and suppress protein I κ B alpha levels, lower NF- κ B
The expression of subunit p65 albumen, and downstream inflammation related proteins iNOS and COX-2 expression can be suppressed
Method：The change of protein level in western blot analysis (Western blot) detection cell
RAW264.7 cells are inoculated in diameter 35mm culture dishes, cultivated after reaching 70%-80% to density, are added not
Testing compound with concentration handles different time, and PBS is washed 2 times, adds cell pyrolysis liquid (50 μ g/ml Aprotinins, 0.5 mM
Phenylmethylsulfonyl fluoride, 1mM sodium vanadates, 10mM sodium fluorides, 10mM β-phosphoglycerol), collect albumen and use Bradford methods
Determine protein concentration.Sample protein (100 μ g) loading is respectively taken, SDS-PAGE protein isolates component simultaneously uses electrotransfer method by albumen
Band is transferred on cellulose nitrate film.Film through TBS prepare 5% skimmed milk power solution room temperature closing 1h after, respectively with
Each 4 DEG C of overnight incubations of testing protein antibody.The secondary antibody that horseradish peroxidase is separately added into after TBS is washed is incubated 1h
Afterwards, analysis of protein is carried out with enhanced ECL chemiluminescences.
As a result：As shown in Figure 10, cell is incubated 1h, NF- κ altogether after 5- amyl group -3- methoxy-phenols handle 1h with LPS
B suppresses protein I κ B alpha levels and risen, and NF- κ B subunit p65 expressing quantities decline, and cell is through 5- amyl group -3- methoxy-phenols
After LPS coprocessing 18h, the inflammation related proteins horizontal dose dependent that presents in NF- κ B downstreams reduces, it was demonstrated that the compound can
Suppress NF- κ B signal paths on protein level.
Embodiment 12：The NF- κ B subunit p65 protein translocations that 5- amyl group -3- methoxy-phenols suppress LPS inductions enter core
Method：Immuno-fluorescence assay NF- κ B subunit p65 intracellular locations
Cell climbing sheet is positioned in 24 orifice plates, is inoculated with RAW264.7 cells, 5- amyl group -3- first is added after cell attachment
After epoxide-phenol is handled 1 hour, 1h is incubated altogether with LPS, PBS is washed 2 times, is added methanol and is fixed 4 hours, and PBS is washed 2 times,
Add p65 antibody incubations 1 hour, PBS is washed 3 times, adds DAPI and fluorescence secondary antibody is incubated 50 minutes, seen using fluorescence microscope
Examine and take pictures.
As a result：Immunofluorescence results are shown (Figure 11), and under cell normal condition, NF- κ B subunits p65 is located in cytoplasm,
P65 enters nucleus under LPS induction states, adds 5- amyl group -3- methoxy-phenols and positive control didox100 (μM) place
After reason, p65 returns to cytoplasm.
Embodiment 13：5- amyl group -3- methoxy-phenols can suppress the inflammatory Cytokines Expression of LPS inductions
Method：ELISA detects inflammatory factor concentration
RAW264.7 cells are inoculated in 24 orifice plates, cultivated after reaching 70%-80% to density, add various concentrations
With LPS coprocessing 18 hours after testing compound pretreatment 1h, cell culture fluid is drawn, after centrifugation, supernatant is taken, according to enzyme-linked
Immunoassay kit specification is operated, and luminous intensity is determined at 450nm.Inflammatory factor concentration is calculated according to standard curve.
As a result：Enzyme linked immunosorbent assay result shows (Figure 12), the inflammation that 5- amyl group -3- methoxy-phenols are induced LPS
The rejection ability of the factor is in dose dependent increase.
Embodiment 14：The preparation of tablet
5- amyl group -3- methoxy-phenol 1g, starch 1.5g, dextrin 1.5g are added, sieving, adds sodium carboxymethylcellulose
In right amount, pelletize.Magnesium Stearate proper quantity is added, mixes, tabletting, produces.
Embodiment 15：The preparation of gel
3 grams of carbomer, 1g polysorbates, 100mL water are well mixed, and add 5- amyl group -3- methoxy-phenol 2g, fully
Mix, and dispense, produce.
The preferred embodiment of the application is the foregoing is only, is not limited to the application, for the skill of this area
For art personnel, the application can have various modifications and variations.It is all within spirit herein and principle, made any repair
Change, equivalent substitution, improvement etc., should be included within the protection domain of the application.
Claims (10)
1.5- amyl group -3- methoxy-phenols in the application for preparing oxidative stress or inflammatory reaction induces an illness in preventing and treating product, its
It is characterized in, the chemical formula of the 5- amyl groups -3- methoxy-phenols is：
2. application as claimed in claim 1, it is characterized in that, the oxidative stress induce an illness for COPD,
Respiratory inflammation, cutaneous lesions, diabetes, nerve degenerative diseases or tumor disease.
3. application as claimed in claim 1, it is characterized in that, the concentration of the 5- amyl groups -3- methoxy-phenols is 6.25~25
μM；Preferably, the concentration of the 5- amyl groups -3- methoxy-phenols is 12.5 μM.
4. application as claimed in claim 1, it is characterized in that, the preparation method of 5- amyl group -3- methoxy-phenols is：By the southern regions of the Yunnan Province
The ethanol extract of Litsea pungens uses petroleum ether extraction, by the part of petroleum ether extraction using petroleum ether-ethyl acetate system ladder
Degree elution, will by the 8th part of petroleum ether-ethyl acetate system gradient elution through sephadex lh-20 chromatogram post separation
The 5th part that sephadex lh-20 chromatogram post separation obtains separates to obtain 5- penta by semipreparative performance liquid chromatographic column
Base -3- methoxy-phenols.
5. a kind of pharmaceutical composition for realizing any described application of Claims 1 to 4, it is characterized in that, active ingredient includes power
Profit requires the 5- amyl group -3- methoxy-phenols used in 1~4 any application.
6. a kind of medicament for realizing any described application of Claims 1 to 4, it is characterized in that, including Claims 1 to 4 is any
5- amyl group -3- the methoxy-phenols and auxiliary material used in the application.
7. medicament as claimed in claim 6, it is characterized in that, the medicament is capsule, tablet, powder, granule, injection
Agent, oral liquid, vina, pill, mixture or tincture.
8. a kind of preparation method of medicament as claimed in claim 6, it is characterized in that, by any application of claims 1 to 3
5- amyl group -3- methoxy-phenols, starch and the dextrin of middle use sieve after mixing, and add sodium carboxymethylcellulose granulation, so
Tabletting produces tablet after adding magnesium stearate mixing afterwards；Or, carbomer and polysorbate are added into water and are well mixed, then add
Enter that the 5- amyl group -3- methoxy-phenols that are used in any application of claims 1 to 3 are well mixed to produce gel.
9. a kind of cosmetics for realizing any application of Claims 1 to 4, it is characterized in that, including Claims 1 to 4 is any
5- amyl group -3- the methoxy-phenols and cosmetic material used in the application.
10. cosmetics as claimed in claim 9, it is characterized in that, the cosmetics are facial mask, face cream, cold cream, skin care
Water, skin care powder or skin-care gel.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109045017A (en) * | 2018-07-10 | 2018-12-21 | 济南市妇幼保健院 | A kind of Polymethoxylated flavanones is preparing the application in anti-oxidation stress medicine |
| CN111205302A (en) * | 2020-01-10 | 2020-05-29 | 贵州景诚制药有限公司 | Litsea pungens fruit extract, extraction method, preparation method and application |
| CN115192569A (en) * | 2022-08-10 | 2022-10-18 | 山东大学 | Application of SphaeropsidinA in preparation of medicine for preventing or treating inflammation-induced diseases |
| CN115192569B (en) * | 2022-08-10 | 2024-05-10 | 山东大学 | Use of Sphaeropsidin A in preparing medicine for preventing or treating inflammation induced diseases |
-
2017
- 2017-11-21 CN CN201711167223.7A patent/CN107669665B/en active Active
Non-Patent Citations (1)
| Title |
|---|
| 孔得刚: "潺槁木姜子和滇南木姜子化学成分研究", 《中国优秀硕士学位论文全文数据库医药卫生科技辑》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109045017A (en) * | 2018-07-10 | 2018-12-21 | 济南市妇幼保健院 | A kind of Polymethoxylated flavanones is preparing the application in anti-oxidation stress medicine |
| CN111205302A (en) * | 2020-01-10 | 2020-05-29 | 贵州景诚制药有限公司 | Litsea pungens fruit extract, extraction method, preparation method and application |
| CN111205302B (en) * | 2020-01-10 | 2021-03-30 | 贵州景诚制药有限公司 | Litsea pungens fruit extract, extraction method, preparation method and application |
| CN115192569A (en) * | 2022-08-10 | 2022-10-18 | 山东大学 | Application of SphaeropsidinA in preparation of medicine for preventing or treating inflammation-induced diseases |
| CN115192569B (en) * | 2022-08-10 | 2024-05-10 | 山东大学 | Use of Sphaeropsidin A in preparing medicine for preventing or treating inflammation induced diseases |
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