CN105726524A - Use of diarylheptanoid compound in preparation of drug or food for preventing and treating psoriasis - Google Patents
Use of diarylheptanoid compound in preparation of drug or food for preventing and treating psoriasis Download PDFInfo
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- CN105726524A CN105726524A CN201410742068.7A CN201410742068A CN105726524A CN 105726524 A CN105726524 A CN 105726524A CN 201410742068 A CN201410742068 A CN 201410742068A CN 105726524 A CN105726524 A CN 105726524A
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Abstract
The invention belongs to the technical field of medicines and discloses a use of a diarylheptanoid compound in preparation of a drug or food for preventing and treating psoriasis. The diarylheptanoid compound has a structure shown in the formula I, wherein 4th-5th sites of the diarylheptanoid compound form a single bond or a double bond, 6th-7th sites of the diarylheptanoid compound form a single bond or a double bond, R1 represents a double bond oxygen group or an acetoxyl group and R2 represents hydrogen, hydroxyl or methoxyl. The diarylheptanoid compound can inhibit proliferation of human skin T cell lymphoma cell line HH cells and human immortalized epidermal keratinocyte producing cell line HaCaT cells and can be used for preparing a drug or a food for preventing and treating psoriasis.
Description
Technical field
The invention belongs to pharmaceutical technology field, preparing, particularly to compound in diphenyl heptane class, the application prevented and treated in psoriasis or food.
Background technology
Psoriasis is a kind of commonly encountered diseases in department of dermatologry, frequently-occurring disease, its cause of disease complexity and recurrent exerbation, is always up the difficult medical problem in the puzzlement whole world.Its histopathology feature main manifestations is epidermal keratinocytes cellulation abnormality proliferation and differentiation, and with the infiltration of scytitis cell.At present, the method for this disease of western medical treatment mainly has four aspects: medicine for external use is treated, such as steroid hormone, tacrolimus and vitamin D3Derivant etc.；Systemic drug is treated, such as tretinoin medicines, methotrexate and ciclosporin etc.；Physiotherapy, such as narrow-band UVB irradiation treatment；Biological preparation, such as Embrel, Ah method's Saite and efalizumab etc..But these therapies are all not fee from the problem of drug dependence and recurrence, and simultaneity factor medicine brings again bigger side effect, and biological preparation is expensive, and these all limit the clinical practice of these therapies.Psoriasis Treated by TCM method is various, is administered flexible and changeable, and curative effect is better, and side effect is little, and has cheap advantage concurrently, receives significant attention in clinical treatment psoriasis.But Chinese medicine compound composition is indefinite, and it is qualitative and method for evaluating safety is perfect not, limits its clinical expansion and application.Therefore, from Chinese medicine, isolate the Chinese medicine monomer of determined curative effect, be the main direction of studying of Psoriasis Treated by TCM from now on.
Guangxi zedoary is the dry rhizome of Zingiberaceae curcuma, is one of conventional Chinese medicine.Within 2005, version Chinese Pharmacopoeia is recorded: Rhizoma Curcumae is the dry rhizome of zingiberaceous plant Rhizoma Curcumae (CurcumaphaeocauLisValeton), Guangxi zedoary (CurcumakwangsiensisS.G.LeeetC.F.Liang) or RADIX CURCUMAE (CurcumawenyujinY.H.ChenetC.Ling), mainly originates in the places such as Guangxi, Sichuan, Zhejiang, Fujian.Chinese medicine and pharmacy theory is thought, its property acrid, bitter, warm, has circulation of qi promoting removing blood stasis, effect of removing food stagnancy pain relieving.Cure mainly vim and vigour pained, eating accumulation, abdominal distention, amenorrhea due to stagnation of blood, dysmenorrhea, traumatic injury.Curcuma typically contains two big active component, i.e. compound in diphenyl heptane class and volatile oil compounds, in addition, possibly together with compositions such as Diterpenes, polysaccharide, phenolic acids and sterols.Have been demonstrated that compound in diphenyl heptane class and volatile oil composition are its primary bioactive components.
The present invention adopt application on human skin t cell lymphoma cell line HH cell and people immortalization epidermal keratinocytes cellulation system HaCaT cell as medicaments sifting model, in-vitro screening treats psoriatic drug candidate, it has been found that the compound in diphenyl heptane class in Traditional Chinese medicine Rhizoma curcumae has the stronger activity suppressing cell proliferation.
Research both at home and abroad by pharmacological experiment confirm compound in diphenyl heptane class there is emesis, tuberculosis, protect the liver, anticoccidial, antifungal, anticancer and suppress the multiple biological activitys such as prostaglandin synthesis.Have no the involved in the present invention relevant report suppressing HTL's cell line HH cell and people immortalization epidermal keratinocytes cellulation system HaCaT cell proliferation.
Summary of the invention
In order to overcome shortcoming and the deficiency of above-mentioned prior art, the primary and foremost purpose of the present invention is in that the application providing compound in diphenyl heptane class in preparation preventing and treating psoriasis or food.
The purpose of the present invention is realized by following proposal:
Compound in diphenyl heptane class application in preparation preventing and treating psoriasis or food.
Described compound in diphenyl heptane class has structure shown in formula I:
Wherein, the 4-5 position of described compound in diphenyl heptane class is singly-bound or double bond, and 6-7 position is singly-bound or double bond；R1For double bond oxygen base or acetoxyl group；R2For hydrogen, hydroxyl or methoxyl group.
Above-mentioned compound in diphenyl heptane class can prepare from plant extract or synthetic method.
Described synthetic method preparation refers to be synthetically derived with the analog of compound.
The preparation method that present invention also offers a kind of above-mentioned compound in diphenyl heptane class, comprises the steps:
(1) Rhizoma Curcumae rhizome is taken, extract with 95% alcohol-water, extract separates through HP-20 macroporous adsorbent resin column chromatography, successively with water, 30% ethanol, 90～100% ethanol gradient elutions, collect each eluent respectively, concentrating under reduced pressure, obtains water elution position, 30% alcohol elution, 90～100% alcohol elutions；
(2) 90～100% alcohol elutions of step (1) are taken, separate through silica gel column chromatography, use chloroform-methanol gradient elution, collecting chloroform-methanol ratio is evaporating of 9:1, through ODS pillar layer separation, using methanol-water gradient elution, collecting methanol-water ratio is the fraction of 6:4, separate through preparative liquid chromatography HPLC, obtain compound in diphenyl heptane class.
In above-mentioned preparation method, step (2) described preparative liquid chromatography, with ratio be 55:45 methanol-water for mobile phase, detection wavelength be 208nm and 220nm, flow velocity is 12mL/min.
Described compound in diphenyl heptane class includes (4E, 6E)-1, double; two (the 4-hydroxy phenyl)-4 of 7-, 6-heptadiene-3-ketone (compound 1), at least one in 1-(3-methoxyl group-4-hydroxy phenyl)-7-(4-hydroxy phenyl)-3-heptanone (compound 2) and 3-acetoxyl group-1-(3,4-dihydroxy phenyl)-7-(4-hydroxy phenyl)-heptane (compound 3).The compound 1 retention time in preparation liquid phase is 10.3min, and the compound 2 retention time in preparation liquid phase is 13.4min, and the compound 3 retention time in preparation liquid phase is 26.1min.
The application in preparation preventing and treating psoriasis of the compound in diphenyl heptane class of the present invention.
Described medicine refers to containing (4E, 6E)-1, double; two (the 4-hydroxy phenyl)-4 of 7-, 6-heptadiene-3-ketone (compound 1), 1-(3-methoxyl group-4-hydroxy phenyl)-7-(4-hydroxy phenyl)-3-heptanone (compound 2) and 3-acetoxyl group-1-(3,4-dihydroxy phenyl) at least one in-7-(4-hydroxy phenyl)-heptane (compound 3), or at least one in its pharmaceutical salts and solvate.Known, the solvation form of compound and salt generally have no effect on the biologic activity of compound self.
Described medicine can contain one or more pharmaceutically acceptable carrier or excipient.
The compound in diphenyl heptane class of described present invention application main manifestations in preparation preventing and treating psoriasis or food is for suppressing HTL's cell line HH cell proliferation and people's immortalization epidermal cell proliferation.
Accompanying drawing explanation
Fig. 1 is that compound in diphenyl heptane class of the present invention is to HTL's cell line HH cell inhibitory effect design sketch.
Fig. 2 is that compound in diphenyl heptane class of the present invention is to people's immortalization epidermal keratinocytes cellulation system HaCaT cell inhibitory effect design sketch.
Detailed description of the invention
Below in conjunction with embodiment and accompanying drawing, the present invention is described in further detail, but embodiments of the present invention are not limited to this.
In embodiment, biological material source used is as follows:
DMEM high glucose medium, hyclone (FBS) are purchased from Hyclone company；Pancreatin Trypsin-EDTA is purchased from Gibco company；RPMI1640 high glucose medium, HTL's cell line HH cell are purchased from ATCC company；Purchased from China typical culture collection center, (CCTCC numbers people immortalization epidermal keratinocytes cellulation system HaCaT cell: GDC106)；CCK-8 cytoactive detection kit is purchased from east Renhua subject skill (Shanghai) Co., Ltd..
Embodiment 1: the extraction of compound in diphenyl heptane class of the present invention and preparation
Take dry Guangxi zedoary rhizome, with 95% ethanol extraction (ethanol: water 95:5, v/v), extract separates through HP-20 macroporous adsorbent resin column chromatography, successively with water, and 30% ethanol, 90～100% ethanol gradient elutions (each gradient eluent consumption 12L), collect each eluent, concentrating under reduced pressure respectively, obtain water elution position, 30v/v% alcohol elution, 90～100v/v% alcohol elution；nullTake 90～100v/v% alcohol elution，Separate through silica gel column chromatography，With chloroform-methanol gradient elution (each gradient eluent consumption 12L)，Collect the fraction E that chloroform-methanol ratio is 9:1，Fraction E is through ODS pillar layer separation，Use methanol-water gradient elution，Collect the fraction E-5 that methanol-water ratio is 6:4，Fraction E-5 separates through preparation liquid phase HPLC，With ratio be 55:45 methanol-water for mobile phase，Detection wavelength is 208nm and 220nm，Flow velocity is 12mL/min，Retention time in preparation liquid phase is 10.3min、13.4min and 26.1min，Separating obtained solution dries，Utilize high resolution mass spectrum (HR-ESI-MS)，Nuclear magnetic resonance, NMR (NMR) method，Determine and obtain (4E,6E)-1,Double; two (the 4-hydroxy phenyl)-4 of 7-,6-heptadiene-3-ketone (compound 1) 115mg，1-(3-methoxyl group-4-hydroxy phenyl) 7-(4-hydroxy phenyl)-3-heptanone (compound 2) 17.5mg and 3-acetoxyl group-1-(3,4-dihydroxy phenyl)-7-(4-hydroxy phenyl)-heptane (compound 3) 23.6mg.
Embodiment 2: compound in diphenyl heptane class vitro inhibition HTL's cell line HH cell proliferation of the present invention detects
1600rpm, 3min are centrifuged and collect the HH cell being in exponential phase, and resuspended with the high glucose medium containing 10%FBSRPMI1640；In 96 orifice plates, every hole adds the HH cell suspension of 100 μ L, to final concentration of 2 × 104Individual cell per well.Embodiment 1 separates the compound 1 obtained and compound 2 is dissolved in DMSO respectively, is configured to the storage liquid of final concentration of 10mM；During use, take storing in the RPMI1640 culture medium that liquid joins 90 μ L of 10 μ L, be diluted to the use liquid of 1mM；Meanwhile, take the DMSO of 10 μ L to join in the RPMI1640 culture medium of 90 μ L and use liquid as negative control group.The liquid that uses taking 0,1,2,2.5,3,3.5,5,10 μ L respectively adds the Concentraton gradient making 0,10,20,25,30,35,50,100 μMs to 96 orifice plates；Meanwhile, negative control group adds the negative control group use liquid of respective volume.37 DEG C, 5%CO2Cultivating 24h in incubator, every hole adds the CCK-8 of 10 μ L, and in incubator, lucifuge cultivates 4h, uses microplate reader to measure the light absorption value of 450nm, and convert suppression ratio, uses the mapping of Graphpad software, and result is shown in Fig. 1.
Suppression ratio %=[1-(experimental group OD/ matched group OD)] × 100%
As seen from Figure 1, by using CCK8 kit measurement cell viability, it is found that compared with negative control group, after the compounds of this invention 1, compound 2 or compound 3 process, HH cell proliferation all receives obvious suppression.
Embodiment 3: the compounds of this invention vitro inhibition people immortalization epidermal keratinocytes cellulation system HaCaT cell proliferation detection
Pancreatin Trypsin-EDTA digestion is used to be in the HaCaT cell of exponential phase；1600rpm, 3min are centrifugal to be collected, and resuspended with the DMED high glucose medium containing 10%FBS；In 96 orifice plates, every hole adds the cell suspension of 100 μ L, to 5000 cells in final concentration of every hole；37 DEG C, 5%CO2Incubator is cultivated 12h；As stated above, the liquid that uses taking different volumes adds the Concentraton gradient making 0,10,20,25,30,35,50,100 μMs to 96 orifice plates；Meanwhile, negative control group adds the negative control group use liquid of respective volume.37 DEG C, 5%CO2Cultivating 24h in incubator, every hole adds the CCK-8 of 10 μ L, and in incubator, lucifuge cultivates 4h, uses microplate reader to measure the light absorption value of 450nm, and convert suppression ratio, uses the mapping of Graphpad software, and result is shown in Fig. 2.
Suppression ratio %=[1-(experimental group OD/ matched group OD)] × 100%
From Figure 2 it can be seen that by using CCK-8 kit measurement cell viability it is found that after the compounds of this invention 1 or compound 2 or compound 3 process, HaCaT cell proliferation all receives obvious suppression.
Above-described embodiment is the present invention preferably embodiment; but embodiments of the present invention are also not restricted to the described embodiments; the change made under other any spirit without departing from the present invention and principle, modification, replacement, combination, simplification; all should be the substitute mode of equivalence, be included within protection scope of the present invention.
Claims (6)
1. compound in diphenyl heptane class application in preparation preventing and treating psoriasis or food.
2. the compound in diphenyl heptane class according to claim 1 application in preparation preventing and treating psoriasis or food, it is characterised in that: described compound in diphenyl heptane class has structure shown in formula I:
Wherein, the 4-5 position of described compound in diphenyl heptane class is singly-bound or double bond, and 6-7 position is singly-bound or double bond；R1For double bond oxygen base or acetoxyl group；R2For hydrogen, hydroxyl or methoxyl group.
3. the compound in diphenyl heptane class according to claim 1 application in preparation preventing and treating psoriasis or food, it is characterised in that: described compound in diphenyl heptane class prepares from plant extract or synthetic method.
4. the compound in diphenyl heptane class according to claim 1 application in preparation preventing and treating psoriasis or food, it is characterized in that: described compound in diphenyl heptane class includes (4E, 6E)-1, double; two (the 4-hydroxy phenyl)-4 of 7-, 6-heptadiene-3-ketone, at least one in 1-(3-methoxyl group-4-hydroxy phenyl)-7-(4-hydroxy phenyl)-3-heptanone and 3-acetoxyl group-1-(3,4-dihydroxy phenyl)-7-(4-hydroxy phenyl)-heptane.
5. the compound in diphenyl heptane class according to claim 1 application in preparation preventing and treating psoriasis or food, it is characterized in that: described medicine refers to containing (4E, 6E)-1, double; two (the 4-hydroxy phenyl)-4 of 7-, 6-heptadiene-3-ketone, 1-(3-methoxyl group-4-hydroxy phenyl)-7-(4-hydroxy phenyl)-3-heptanone and 3-acetoxyl group-1-(3,4-dihydroxy phenyl) at least one in-7-(4-hydroxy phenyl)-heptane, or at least one in its pharmaceutical salts and solvate.
6. the compound in diphenyl heptane class according to claim 1 application in preparation preventing and treating psoriasis or food, it is characterised in that: described medicine can contain one or more pharmaceutically acceptable carrier or excipient.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108653253A (en) * | 2018-05-07 | 2018-10-16 | 武汉轻工大学 | Galangal diphenyl heptane class component is preparing application and preparation in preventing and/or treating the preparation of pig epidemic diarrhea |
| CN111643669A (en) * | 2020-06-30 | 2020-09-11 | 广东省中医院（广州中医药大学第二附属医院、广州中医药大学第二临床医学院、广东省中医药科学院） | Application of glutaminase inhibitor in preparation of medicine for treating psoriasis |
| CN111728968A (en) * | 2020-07-08 | 2020-10-02 | 桂林医学院 | Application of daphnetin in preparation of medicine for treating psoriasis |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101979366A (en) * | 2010-09-26 | 2011-02-23 | 沈阳药科大学 | Diarylheptanoid compounds in curcuma zedoary and medicinal application thereof |
| CN103083289A (en) * | 2013-01-25 | 2013-05-08 | 广东省中医院 | Application of curcumin in preparation of medicine for treating psoriasis |
-
2014
- 2014-12-08 CN CN201410742068.7A patent/CN105726524A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101979366A (en) * | 2010-09-26 | 2011-02-23 | 沈阳药科大学 | Diarylheptanoid compounds in curcuma zedoary and medicinal application thereof |
| CN103083289A (en) * | 2013-01-25 | 2013-05-08 | 广东省中医院 | Application of curcumin in preparation of medicine for treating psoriasis |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108653253A (en) * | 2018-05-07 | 2018-10-16 | 武汉轻工大学 | Galangal diphenyl heptane class component is preparing application and preparation in preventing and/or treating the preparation of pig epidemic diarrhea |
| CN111643669A (en) * | 2020-06-30 | 2020-09-11 | 广东省中医院（广州中医药大学第二附属医院、广州中医药大学第二临床医学院、广东省中医药科学院） | Application of glutaminase inhibitor in preparation of medicine for treating psoriasis |
| CN111728968A (en) * | 2020-07-08 | 2020-10-02 | 桂林医学院 | Application of daphnetin in preparation of medicine for treating psoriasis |
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