CN104606178A - Application of 2-valeryl-1, 5-cyclohexadiene-1-carboxylic acid in preparing medicine for treating chloasma - Google Patents
Application of 2-valeryl-1, 5-cyclohexadiene-1-carboxylic acid in preparing medicine for treating chloasma Download PDFInfo
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- CN104606178A CN104606178A CN201510065388.8A CN201510065388A CN104606178A CN 104606178 A CN104606178 A CN 104606178A CN 201510065388 A CN201510065388 A CN 201510065388A CN 104606178 A CN104606178 A CN 104606178A
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- valeryl
- cyclohexadiene
- carboxylic acid
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Abstract
The invention discloses application of 2-valeryl-1, 5-cyclohexadiene-1-carboxylic acid in preparing a medicine for treating chloasma. According to the relation between generation of the chloasma and the endocrine disorder and excessive daylight irradiation, a mouse model with the chloasma is established, and the treating action of the compound for the chloasma by observing the influence of the 2-valeryl-1, 5-cyclohexadiene-1-carboxylic acid on the contents of tyrosine and lipofuscin, so that a new candidate medicine for treating the chloasma is brought for clinic practice.
Description
Technical field
The invention belongs to medical art, prepare the application in the medicine for the treatment of chloasma in particular to 2-valeryl-1,5-cyclohexadiene-1-carboxylic acid.
Background technology
Chloasma (chloasma) is a kind ofly apt to occur in female face and the hyperpigmentation dermatoses of refractory, clinical manifestation is that facial area occurs that limitation is filbert or brown pigment is calm, skin lesion is yellowish-brown or dark brown patch, often be symmetrically distributed in cheekbone portion, face, buccal, in butterfly shape, or involve forehead, nose, mouth week and chin portion be irregularly shaped, be apt to occur in young and middle-aged women.Current research thinks that the generation of chloasma is relevant with endocrine regulation, and there are some researches prove that estrogen can stimulation melanin emiocytosis melanin granule, and progestogen can promote the transhipment of melanosome and increase melanin amount, finally cause pigmentation.The cause of disease of chloasma is except outside the Pass having with endocrine regulation, sun exposure is also a key factor, after excessive ray irradiates, chloasma can increase the weight of, avoid Exposure to Sunlight that chloasma can be made to alleviate and even disappear, long term ultraviolet irradiates especially ultraviolet B radiation (UVB) can make melanocyte rise in value, and melanin amount increases.
CN102795991A discloses a kind of 2-valeryl-1; 5-cyclohexadiene-1-carboxylic acid and synthetic method thereof and application; having under catalyst existent condition; make 4; 5-dihydro-1 (3H)-isobenzofuranone and butyraldehyde react and generate 3-(1 '-hydroxyl) butyl-4; 5-dihydro-1 (3H)-isobenzofuranone; react with pyridine again and generate 3-cyclobutenyl-4; 5-dihydro-1 (3H)-isobenzofuranone; then sodium hydroxide hydrolysis is added; generate 2-valeryl-1,5-cyclohexadiene-1-carboxylic acid.This patented technology further discloses 2-valeryl-1,5-cyclohexadiene-1-carboxylic acid and has analgesic effect, can be used in the medicine preparing prevention or treatment pain especially dysmenorrhea.
By retrieval domestic and foreign literature, still do not find that 2-valeryl-1,5-cyclohexadiene-1-carboxylic acid has the bioactive bibliographical information reducing tyrosine, lipofuscin content in skin.
Summary of the invention
In view of the deficiencies in the prior art, the object of the present invention is to provide a kind of new pharmaceutical use, i.e. the application of 2-valeryl-1,5-cyclohexadiene-1-carboxylic acid in the medicine of preparation treatment chloasma.
The present inventor finds in test unexpectedly, and 2-valeryl-1,5-cyclohexadiene-1-carboxylic acid has the effect suppressing tyrosine to generate, and then by providing the pharmaceutical applications of this compound after further investigation, achieves object of the present invention.
Skin pigment is formed in skin base layer melanoblast.In vitro study shows, the synthesis of skin pigment is that tyrosine is oxidized to DOPA lentamente by the effect of tryrosinase, the DOPA intermedium that oxidation formation is colourless under the impact of dopase again, this material is under the further impact of tyrosine, finally be oxidized to brown melanin, visible, tyrosine increases the main matter basis for chloasma morbidity.Proved that estrogen can stimulate melanocyte to secrete melanin granule, progestogen can impel melanosome combine and increase its amount.In addition, chloasma also has an important exogenous stimulating factor to be ultraviolet, and especially wavelength is that the ability of the ultraviolet B radiation activity of tyrosinase of 290-380nm is the strongest, thus promotes melanocytic formation further.
The present inventor according to the generation of chloasma and endocrine regulation, excessive sun exposure is relevant establishes chloasma mouse model, observe respectively the tyrosine in mouse model skin, lipofuscin content change as modeling whether successfully foundation.And by observing 2-valeryl-1,5-cyclohexadiene-1-carboxylic acid to the impact of These parameters, study its therapeutical effect to chloasma.Result of the test shows, and 2-valeryl-1,5-cyclohexadiene-1-carboxylic acid has certain preventive and therapeutic effect to mice chloasma model, and its action target spot is the propagation of check melanin cell and the generation of tyrosine, thus suppresses the formation of chloasma.
Based on the result of study of inventor, the invention provides following pharmaceutical applications:
The application of 2-valeryl-1,5-cyclohexadiene-1-carboxylic acid or derivatives thereof in the medicine preparing check melanin cell proliferation or health product.
The application of 2-valeryl-1,5-cyclohexadiene-1-carboxylic acid or derivatives thereof in the medicine or health product of the generation of preparation suppression tyrosine.
The application of 2-valeryl-1,5-cyclohexadiene-1-carboxylic acid or derivatives thereof in the medicine of preparation treatment chloasma.
It should be noted that; described 2-valeryl-1; the derivant of 5-cyclohexadiene-1-carboxylic acid is its 2-valeryl-1; the precursor compound of 5-cyclohexadiene-1-carboxylic acid; this precursor compound has more weak activity or does not even have activity; but (such as by metabolism, solvolysis or other mode) is converted to 2-valeryl-1,5-cyclohexadiene-1-carboxylic acid upon administration, in physiological conditions.
Based on 2-valeryl-1; 5-cyclohexadiene-1-carboxylic acid can the propagation of check melanin cell and the generation of tyrosine; therefore the present invention proposes 2-valeryl-1 first; 5-cyclohexadiene-1-carboxylic acid is for the preparation of medicine or the health product for the treatment of chloasma; for bringing the drug candidate of new this disease for the treatment of clinically, there is larger clinical value.
Detailed description of the invention
Be below effect test of the present invention example, the description of these embodiments can understand and apply the invention for ease of those skilled in the art.Person skilled in the art obviously easily can make various amendment to these embodiments, and General Principle described herein is applied in other embodiments and need not through performing creative labour.Therefore; protection scope of the present invention is not limited to these embodiments; those skilled in the art are according to announcement of the present invention; do not depart from improvement that scope makes and amendment all should within protection scope of the present invention; the application of derivant in the medicine of preparation treatment chloasma of such as 2-valeryl-1,5-cyclohexadiene-1-carboxylic acid.
embodiment 1:2-valeryl-1,5-cyclohexadiene-1-carboxylic acid affects experimental study to tyrosine, lipofuscin content in chloasma mouse skin
SPF level Kunming mouse 40, female, body weight 28-32g.Mice is divided into Normal group, model control group, medicine high and low dose group at random, often organizes 10.Adaptability starts test after raising one week, Normal group intramuscular injection sterilized water for injection 5ml/kg; Model control group and each administration group intramuscular injection progesterone injection 20mg/kg.Each group is all injected in mice thigh root, 1 time on the 1st, and both sides alternately, set totally 30 days, wavelength 350nm ultraviolet radiation 30 minutes (height 30 centimetres, area 20 × 30mm) with EB-160/FE uviol lamp simultaneously.After modeling the 16th day, each group mice gave tested material by following dosage gavage:
Normal group: normal saline 0.2ml/10g;
Model control group: normal saline 0.2ml/10g;
Medicine low dose group: 2-valeryl-1,5-cyclohexadiene-1-carboxylic acid 2mg/kg;
Medicine high dose group: 2-valeryl-1,5-cyclohexadiene-1-carboxylic acid 8mg/kg.
Each group of every day gives corresponding tested material 1 time, continuous 30 days.Put to death animal in last administration after 2 hours, the skin histology of UV-irradiating portion of learning from else's experience respectively is appropriate, makes 10% tissue homogenate, centrifuging and taking supernatant, the tyrosine of detection of skin and skin lipofuscin contents level in ice bath.
Can be found out by the result of the test of table 1, compare with Normal group, in model control group mouse skin, the content of tyrosine, lipofuscin all significantly increases, and hints model is successfully prepared; Compare with model control group, medicine high and low dose group all obviously can reduce content and the lipofuscin content of tyrosine in chloasma mouse skin, difference have extremely significant statistical significance (
p< 0.01).
Table 1 respectively organizes tyrosine, lipofuscin comparision contents in chloasma mouse skin
| Group | n | Tyrosine (μ g/100mg) | Lipofuscin (μ g/g) |
| Normal group | 10 | 9.49±1.71 | 1.49±0.82 |
| Model control group | 10 | 17.02±3.63 ** | 2.05±0.19 ** |
| Medicine low dose group | 10 | 8.63±2.14 ## | 1.47±0.06 ## |
| Medicine high dose group | 10 | 9.17±1.55 ## | 1.39±0.15 ## |
Compare with Normal group,
* p< 0.05;
* p< 0.01
Compare with model control group,
# p< 0.05;
## p< 0.01.
Claims (3)
- The application of 1.2-valeryl-1,5-cyclohexadiene-1-carboxylic acid or derivatives thereof in the medicine preparing check melanin cell proliferation or health product.
- The application of 2.2-valeryl-1,5-cyclohexadiene-1-carboxylic acid or derivatives thereof in the medicine or health product of the generation of preparation suppression tyrosine.
- The application of 3.2-valeryl-1,5-cyclohexadiene-1-carboxylic acid or derivatives thereof in the medicine of preparation treatment chloasma.
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| CN201510065388.8A CN104606178A (en) | 2015-02-09 | 2015-02-09 | Application of 2-valeryl-1, 5-cyclohexadiene-1-carboxylic acid in preparing medicine for treating chloasma |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510065388.8A CN104606178A (en) | 2015-02-09 | 2015-02-09 | Application of 2-valeryl-1, 5-cyclohexadiene-1-carboxylic acid in preparing medicine for treating chloasma |
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| CN104606178A true CN104606178A (en) | 2015-05-13 |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58107191A (en) * | 1981-12-18 | 1983-06-25 | Ajinomoto Co Inc | Preparation of l-1,4-cyclohexadiene-1-alanine |
| CN101234132A (en) * | 2007-01-31 | 2008-08-06 | 成都彩子化妆品有限公司 | New use of angelica sinensis or its extract in preparing skin care products |
| CN102795991A (en) * | 2012-08-25 | 2012-11-28 | 神威药业集团有限公司 | 2-valeryl-1,5-cyclohexadiene-1-carboxylic acid, and synthetic method and application thereof |
| CN102809619A (en) * | 2012-08-25 | 2012-12-05 | 神威药业集团有限公司 | Method for determining ligustilide in natural medicinal preparation |
| CN103209697A (en) * | 2010-08-11 | 2013-07-17 | 吾儿得伟有限公司 | Composition for preventing and alleviating brain disease comprising silk amino acid and tyrosine as active ingredients |
-
2015
- 2015-02-09 CN CN201510065388.8A patent/CN104606178A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58107191A (en) * | 1981-12-18 | 1983-06-25 | Ajinomoto Co Inc | Preparation of l-1,4-cyclohexadiene-1-alanine |
| CN101234132A (en) * | 2007-01-31 | 2008-08-06 | 成都彩子化妆品有限公司 | New use of angelica sinensis or its extract in preparing skin care products |
| CN103209697A (en) * | 2010-08-11 | 2013-07-17 | 吾儿得伟有限公司 | Composition for preventing and alleviating brain disease comprising silk amino acid and tyrosine as active ingredients |
| CN102795991A (en) * | 2012-08-25 | 2012-11-28 | 神威药业集团有限公司 | 2-valeryl-1,5-cyclohexadiene-1-carboxylic acid, and synthetic method and application thereof |
| CN102809619A (en) * | 2012-08-25 | 2012-12-05 | 神威药业集团有限公司 | Method for determining ligustilide in natural medicinal preparation |
Non-Patent Citations (1)
| Title |
|---|
| 康金森等: "红玉祛斑胶囊对黄褐斑模型小鼠的影响", 《中药药理与临床》 * |
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