KR101834550B1 - Composition for preventing, improving or treating vascular diseases comprising 3-caffeoyl-4-dihydrocaffeoylquinic acid as effective component - Google Patents
Composition for preventing, improving or treating vascular diseases comprising 3-caffeoyl-4-dihydrocaffeoylquinic acid as effective component Download PDFInfo
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- KR101834550B1 KR101834550B1 KR1020150171156A KR20150171156A KR101834550B1 KR 101834550 B1 KR101834550 B1 KR 101834550B1 KR 1020150171156 A KR1020150171156 A KR 1020150171156A KR 20150171156 A KR20150171156 A KR 20150171156A KR 101834550 B1 KR101834550 B1 KR 101834550B1
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- acid
- caffeoyl
- composition
- disease
- nitric oxide
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Abstract
The present invention relates to 3-dihydro-4-five days cafe cafe five days quinolyl prevention, a composition for improving or treating vascular disease comprising the acid as an active ingredient, 3-isolated from Salicornia (Salicornia herbacea) according to the invention When 3-caffeoyl-4-dihydrocaffeoylquinic acid was administered to vascular endothelial cells, the expression of phospho-eNOS (endothelial nitric oxide synthase) was increased and NO (nitric acid) And the generated NO is liberated into blood vessels and induces relaxation of smooth muscle to relax the blood vessels. Therefore, blood vessels such as hypertension, arteriosclerosis, coronary artery disease, cerebrovascular disease, peripheral vascular disease, or aortic disease Can be usefully used as a composition for preventing, ameliorating or treating diseases.
Description
The present invention relates to a composition for preventing, improving or treating vascular diseases containing 3-caffeoyl-4-dihydrocafeoyl-quinic acid as an active ingredient, and more particularly, to a composition for preventing, Which comprises 3-caffeoyl-4-dihydrocaffeoyl-quinic acid as an active ingredient, to a composition for preventing, improving or treating vascular diseases.
The endothelium of blood vessels plays an important role in maintaining vascular homeostasis in vasoreactivity, platelet activation, leukocyte adhesion, proliferation and migration of smooth muscle cells. The nitric oxide (NO) produced in the vascular endothelium is the most potent substance to protect the blood vessels. It relaxes the vascular smooth muscle cells and expands blood vessels. The damaged NO signaling system is atherosclerosis and hypertension, And the like. Nitric oxide synthase (NOS) is an enzyme that catalyzes the conversion of O 2 and the cofactor nicotinamide adenine dinucleotide phospate (NADPH), flavin adenine dinucleotide (FAD), flavin mononucleotide (FMN) Arginine is a group of enzymes that synthesize NO from the terminal nitrogen atom of L-arginine in the presence of heme, tetrahydrobiopterin (BH4). Of the known NOSs, n-NOS (neuronal nitric oxide (eosinophils), eosinophils (eosinophils), eosinophils (eosinophils), eosinophils (eosinophils), and eosinophils.
On the other hand, Salicornia herbacea ( Salicornia herbacea ) is an annual plant that grows in the coastal waters of Korea. It is also known as a mildew or mullet. It is also called a coral reef because its whole shape resembles a coral. It is recorded as "green tea" in the Chinese medicine medical book "Chinese medicine" which is the best medicine book in China, and "Shincho", "Chinese medicine" or " Has been used. It removes toxins and succulents accumulated in the body and has excellent therapeutic effect on cancer, myoma, sinusitis, hypertension, hypotension, back pain, diabetes, bronchial asthma, hypothyroidism, hyperthyroidism, skin disease, arthritis, nephritis or various incurable diseases It is known as the amazing herb that it has.
Korean Patent Publication No. 2011-0081007 discloses a composition for prevention or improvement of hypertension including a fermented product of green tea, Korean Patent No. 1323157 discloses a composition for preventing or improving hypertension comprising 3-caffeoyl-4-dihydrocaffeoylquinic acid As an active ingredient, a pharmaceutical composition for inhibiting cancer metastasis. However, a composition for preventing, improving or treating vascular diseases containing 3-caffeoyl-4-dihydrocafeoylquinic acid as an active ingredient of the present invention has not yet been disclosed.
The present invention has been made in view of the above-mentioned needs, and the present inventors have found that Salicornia 3-caffeoyl-4-dihydrocaffeoylquinic acid was isolated from herbacea and the 3-caffeoyl-4-dihydrocaffeoylquinic acid was treated with vascular endothelial cells (Endothelial nitric oxide synthase), thereby increasing the amount of NO (nitric acid) produced. The present invention has been completed based on this finding.
In order to solve the above-mentioned problems, the present invention provides a pharmaceutical composition for preventing or ameliorating vascular diseases containing 3-caffeoyl-4-dihydrocaffeoylquinic acid or a salt thereof as an active ingredient Functional food composition.
The present invention also relates to a pharmaceutical composition for preventing or treating vascular diseases containing 3-caffeoyl-4-dihydrocaffeoylquinic acid or a pharmaceutically acceptable salt thereof as an active ingredient Lt; / RTI >
When 3-caffeoyl-4-dihydrocaffeoylquinic acid isolated from Salicornia herbacea according to the present invention was treated with vascular endothelial cells, phospho-eNOS (endothelial nitric acid (nitric acid) production is increased by increasing the expression level of nitric oxide synthase (NO synthase), and the generated NO is liberated into blood vessels to induce relaxation of smooth muscle to relax blood vessels. Thus, hypertension, arteriosclerosis, coronary artery disease , Vascular diseases such as cerebrovascular disease, peripheral vascular disease, or aortic disease, and the like.
FIG. 1 is a graph showing the effect of 3-caffeoyl-4-dihydrocaffeoylquinic acid on the vascular endothelial cells at various concentrations according to an embodiment of the present invention. ). CDCQ is 3-caffeoyl-4-dihydrocaffeoylquinic acid.
FIG. 2 is a graph showing the results of treatment of 3-caffeoyl-4-dihydrocaffeoylquinic acid according to an embodiment of the present invention on endothelial cells at various concentrations, phospho-eNOS (endothelial nitric oxide synthase). β-actin is a loading control.
FIG. 3 is a graph illustrating the effect of 3-caffeoyl-4-dihydrocaffeoylquinic acid (NO) on nitric oxide (NO) when treated with various concentrations of vascular endothelial cells according to an embodiment of the present invention. (A) and fluorescence intensity graph (B), respectively.
FIG. 4 is a graph showing that when 3-caffeoyl-4-dihydrocaffeoylquinic acid is treated with vascular endothelial cells over time, phospho-eNOS and NO (A) and CaMKIIa (calcium / calmodulin-dependent protein kinase) (B), which are related to the signal transduction pathway. β-actin is a loading control.
FIG. 5 is a graph showing the results of pretreatment of H-89 and KN-93 which are inhibitors of PKA and CaMKIIa according to an embodiment of the present invention, respectively, on vascular endothelial cells, and then 3-caffeoyl -4-dihydrocaffeoylquinic acid), the expression level of phospho-eNOS is shown. β-actin is a loading control.
FIG. 6 is a graph showing the results of pretreatment of vascular endothelial cells with H-89 and KN-93, inhibitors of PKA and CaMKIIa, respectively, according to an embodiment of the present invention, and then 3-caffeoyl-4-dihydro caffeoylquinic acid (3- caffeoyl-4-dihydrocaffeoylquinic acid), the degree of formation of NO (nitric oxide) is represented by a total fluorescence microscope photograph (A) and a fluorescence intensity graph (B).
In order to achieve the above object, the present invention provides a pharmaceutical composition for preventing or ameliorating vascular diseases comprising 3-caffeoyl-4-dihydrocaffeoylquinic acid or a salt thereof as an active ingredient Functional food composition.
The 3-caffeoyl-4-dihydrocaffeoic acid may be isolated from Salicornia herbacea , but is not limited thereto.
The vascular disease may be, but is not limited to, atherosclerosis, hypertension, cerebrovascular disease, peripheral vascular disease, or aortic disease.
The health functional food composition for preventing or ameliorating the vascular disease may increase the expression amount of phospho-eNOS (endothelial nitric oxide synthase) in vascular endothelial cells to increase the production amount of nitric acid (NO), but the present invention is not limited thereto.
When the health functional food composition for preventing or ameliorating vascular diseases according to the present invention is used as a food additive, the health functional food composition may be added as it is or may be used together with other food or food ingredients, . Generally, the health functional food composition of the present invention is added in an amount of not more than 15 parts by weight, preferably not more than 10 parts by weight based on the raw material, when the food or beverage is produced. However, in the case of long-term intake for the purpose of controlling health, the amount may be less than the above range, and since there is no problem in terms of safety, the active ingredient may be used in an amount exceeding the above range.
There is no particular limitation on the kind of the health functional food. Examples of the foods to which the health functional food composition can be added include dairy products including meat, sausage, bread, chocolate, candy, snacks, confectionery, pizza, ramen and other noodles, gums, ice cream, soups, , A drink, an alcoholic beverage, and a vitamin complex, all of which include health foods in a conventional sense.
In addition, the health functional food composition of the present invention can be produced as a food, particularly a functional food. The functional food of the present invention includes components that are ordinarily added in food production, and includes, for example, proteins, carbohydrates, fats, nutrients, and seasonings. For example, in the case of a drink, a natural carbohydrate or a flavoring agent may be included as an additional ingredient in addition to the active ingredient. The natural carbohydrate may be selected from the group consisting of monosaccharides (e.g., glucose, fructose, etc.), disaccharides (e.g., maltose, sucrose, etc.), oligosaccharides, polysaccharides (e.g., dextrin, cyclodextrin, For example, xylitol, sorbitol, erythritol, etc.). The flavoring agent may be a natural flavoring agent (e.g., tau Martin, stevia extract, etc.) and a synthetic flavoring agent (e.g., saccharin, aspartame, etc.).
In addition to the above health functional food composition, it is also possible to use various nutrients, vitamins, electrolytes, flavors, colorants, pectic acids and salts thereof, alginic acid and salts thereof, organic acids, protective colloid thickening agents, pH adjusting agents, stabilizers, preservatives, glycerin, A carbonating agent used in beverages, and the like. Although the ratio of the above-mentioned ingredients is not critical, it is generally selected in the range of 0.01 to 0.1 part by weight based on 100 parts by weight of the health functional food composition of the present invention.
The present invention also relates to a pharmaceutical composition for preventing or treating vascular diseases containing 3-caffeoyl-4-dihydrocaffeoylquinic acid or a pharmaceutically acceptable salt thereof as an active ingredient Lt; / RTI >
The salt is not particularly limited as long as it is pharmaceutically acceptable so long as it is pharmaceutically acceptable and includes, for example, hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, hydrofluoric acid, hydrobromic acid, formic acid acetic acid, tartaric acid, lactic acid, citric acid, fumaric acid, , Benzenesulfonic acid, toluenesulfonic acid, and naphthalenesulfonic acid. In addition to acid addition salts, additional base salts such as sodium hydroxide, potassium hydroxide, triethylamine, tertiary-butylamine may also be used.
The pharmaceutical composition for the prevention or treatment of vascular diseases of the present invention may further comprise an appropriate carrier, excipient or diluent conventionally used in the production of a pharmaceutical composition.
The pharmaceutical composition for the prevention or treatment of vascular diseases according to the present invention can be administered orally or parenterally in the form of powders, granules, tablets, capsules, oral preparations such as suspensions, emulsions, syrups and aerosols, external preparations, suppositories, And the like. Examples of carriers, excipients and diluents that can be included in the pharmaceutical composition of the present invention include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, acacia rubber, alginate, gelatin, calcium phosphate, calcium silicate , Various compounds or mixtures including cellulose, methyl cellulose, microcrystalline cellulose, polyvinylpyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil. In the case of formulation, a diluent or excipient such as a filler, an extender, a binder, a wetting agent, a disintegrant, or a surfactant is usually used. Solid form preparations for oral administration include tablets, pills, powders, granules, capsules and the like, which may contain at least one excipient such as starch, calcium carbonate, sucrose or lactose, gelatin, . In addition to simple excipients, lubricants such as magnesium stearate and talc are also used. Examples of liquid formulations for oral use include suspensions, solutions, emulsions and syrups. In addition to water and liquid paraffin, which are commonly used simple diluents, various excipients such as wetting agents, sweeteners, fragrances, preservatives and the like have. Formulations for parenteral administration include sterilized aqueous solutions, non-aqueous solutions, suspensions, emulsions, freeze-dried preparations, and suppositories. Examples of the suspending agent include propylene glycol, polyethylene glycol, vegetable oil such as olive oil, injectable ester such as ethyl oleate, and the like. Examples of the suppository base include withexol, macrogol, tween 61, cacao butter, laurin, glycerogelatin and the like.
A suitable dose of the pharmaceutical composition of the present invention may be variously prescribed by factors such as the formulation method, the administration method, the age, body weight, sex, pathological condition, food, administration time, administration route, excretion rate and responsiveness of the patient .
The pharmaceutical composition of the present invention may be administered orally or parenterally. In the case of parenteral administration, the composition may be administered topically to the skin, intravenously, subcutaneously, intramuscularly, intraperitoneally, or transdermally.
Hereinafter, the present invention will be described in more detail with reference to Examples. It is to be understood by those skilled in the art that these embodiments are merely illustrative of the present invention and that the scope of the present invention is not limited thereto.
Example One. From Hamcho 3-caffeoyl-4-dihydro Cafe oil Quinic detach
1.5 kg of the dried plant extracts collected from the tidal flats of the west coast were cut off and extracted with 100% (v / v) methanol for 3 days. After filtration under reduced pressure, the methanol concentrate was concentrated under reduced pressure in a water bath at 60 ° C., Lt; / RTI > The methanol extract suspended in distilled water was extracted with shaking with 2 l of ethyl acetate to obtain a water layer. The water layer was concentrated under reduced pressure in a water bath at 60 캜 to remove ethyl acetate present in the water layer. The water layer with ethyl acetate removed was adsorbed on Diaion HP-20 column chromatography equilibrated with distilled water, washed with water, and then extracted with 30% (v / v) methanol solution to obtain an active substance To obtain an active fraction. Thereafter, the active fractions were concentrated under reduced pressure, dissolved in a small amount of methanol, and developed on a Sephadex LH-20 gel column chromatography equilibrated with methanol to obtain active fractions. The fractions were separated by a YMC gel ODS column chromatography (V / v) acetonitrile aqueous solution at acidic conditions using YMC gel ODS column chromatography using high performance liquid chromatography. As a result of instrumental analysis, the compound 3-caffeoyl-4-dihydrocaffeoylquinic acid (CDCQ, molecular formula: C 25 H 26 O 12 ) was obtained.
Example 2. In vascular endothelial cells, 3-caffeoyl-4-dihydro Cafe oil Quinic Cytotoxicity check
In order to confirm that 3-caffeoyl-4-dihydrocaffeoylquinic acid (CDCQ) of the present invention is a compound without cytotoxicity, 1, 5, 10, 20 And 50 μM of CDCQ were cultured for 24 hours and cultured for 24 hours using MTT (3- (4,5-dimethylthiazol-2-yl) -2,5-diphenyltetrazolium bromide) assay kit (USB corporation, Cleveland, OH USA) Cell viability was measured. For this, EA.hy926 cells were divided into 48-well plates at a density of 1 × 10 4 cells / well and cultured for 24 hours. Then, the CDCQ was diluted to different concentrations while replacing 500 μl of the cell culture medium, Lt; / RTI > Thereafter, the treated medium for each sample was collected, treated with 0.2 mg / ml of MTT solution in a 96-well plate, and reacted for 30 minutes. After the completion of the reaction, the supernatant was removed, and 100 mu l of DMSO (dimethyl sulfoxide) was added to dissolve the generated formazan crystals, and the absorbance at 550 nm was measured with a microplate analyzer. As a result, when the CDCQ of the present invention was treated with the endothelial cells of the present invention as shown in FIG. 1, no cytotoxicity was observed at a concentration of 50 μM or less (Fig. 1).
Example 3. In vascular endothelial cells, 3-caffeoyl-4-dihydro Cafe oil Quinic acid Depending on the treatment phospho - eNOS ( endothelial nitric oxide synthase ),
EA.hy926 cells were treated with 3-caffeoyl-4-dihydrocaffeoylquinic acid (CDCQ) of the present invention for 1 hour to obtain total cell lysates And the expression of phospho - eNOS (endothelial nitric oxide synthase) in the cell lysate was confirmed by Western blot analysis. As a result, as shown in FIG. 2, it was confirmed that the expression level of phospho-eNOS was increased in a concentration-dependent manner by treatment with CDCQ in vascular endothelial cells.
Example 4. In vascular endothelial cells, 3-caffeoyl-4- Dihydro caffe oil Quinic acid Treatment with NO ( nitric acid )
The degree of NO production in vascular endothelial cells was measured using DAF-FM diacetate (4-Amino-5-methylamino-2 ', 7'-difluorofluorescein diacetate, Molecular Probe, OR). The vascular endothelial cells were attached to 96-well plates at a density of 5 x 10 < 4 > cfu / ml. Cells were cultured in growth medium for 12 hours, cultured in medium lacking FBS (fetal bovine serum) at 37 ° C for 3 hours, treated with L-NAME (LN G- nitroarginine methyl ester, 100M) And then pretreated for 30 min. Then, the CDCQ of the present invention was treated for 60 minutes, the vascular endothelial cells were washed twice with PBS, and then treated with 10 μM of DAF-FM diacetate for 20 minutes. After the medium was removed, the cells were fixed with 4% paraformaldehyde as a fixing solution for 5 minutes, and the fluorescence was measured by replacing the medium with FBS-free medium. The excitation wavelength is 488 nm and when NO is bound to DAF, it fluoresces at 515 nm. FIG. 3 shows the results of measurements with a total internal fluorescence microscope (Nikon, Japan) and a microplate reader, showing that the production of NO by CDCQ treatment in vascular endothelial cells was concentration-dependent , Respectively.
Example 5. In vascular endothelial cells, 3-caffeoyl-4- Dihydro caffe oil Quinic acid Depending on the treatment phospho - eNOS And NO Confirmation of the expression pattern of the signal transduction-related protein
EA.hy926 cells were treated with 20 .mu.M CDCQ for 10, 30 and 60 minutes to obtain total cell lysates. Western blot analysis was performed to investigate the phospho - eNOS expression-related signaling proteins in the cell lysate As a result, as shown in FIG. 4, it was confirmed that CDCQ of the present invention increases the expression amount of PKA (protein kinase A) and CaMKIIa (calcium / calmodulin-dependent protein kinase). In order to confirm the relationship between the expression of the signal transduction proteins PKA and CaMKIIa and phospho - eNOS, inhibitors of PKA and CaMKIIa, H - 89 and KN - 93, respectively, were used. The vascular endothelial cells were pretreated with each inhibitor for 1 hour and then treated with 20 μM of CDCQ for 1 hour to obtain total cell lysate. Western blot analysis was performed to examine the expression level of phospho - eNOS in the cell lysate. Results As shown in FIG. 5, it was confirmed that the expression of PKA and CaMKIIa, which are signal transduction proteins in vascular endothelial cells, is involved in the expression of phospho - eNOS by CDCQ.
In order to confirm the relationship between expression of the signal transduction proteins PKA and CaMKIIa and NO production, H-89 and KN-93 inhibitors of PKA and CaMKIIa were added to vascular endothelial cells for 1 hour After pretreatment, 20 μM of CDCQ was treated for 1 hour and the degree of fluorescence was measured using DAF-FM diacetate (Molecular Probe, OR). FIG. 6 shows the results obtained by photographing with a total internal fluorescence microscope (Nikon, Japan) and a microplate analyzer, showing that PKA and CaMKIIa, which are signal transduction proteins, are involved in NO production by CDCQ in vascular endothelial cells .
Claims (7)
[Chemical Formula 1]
[Chemical Formula 1]
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| KR20220037530A (en) | 2020-09-17 | 2022-03-25 | 농업회사법인 주식회사 장수식품 | A composition for improving, preventing and treating of vascular disease |
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Non-Patent Citations (1)
| Title |
|---|
| Man Hee Rhee 외 2명, Salicornia herbacea: Botanical, chemical and pharmacological review of halophyte marsh plant, Journal of Medicinal Plants Research Vol. 3(8), pp. 548-555, August, 2009년 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20220037530A (en) | 2020-09-17 | 2022-03-25 | 농업회사법인 주식회사 장수식품 | A composition for improving, preventing and treating of vascular disease |
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