CN101869559A - Application of gartanin compound in preparing medicaments for treating hyperlipidemia - Google Patents
Application of gartanin compound in preparing medicaments for treating hyperlipidemia Download PDFInfo
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Abstract
The invention relates to application of a gartanin compound in preparing medicaments for treating hyperlipidemia. An extracting and preparing method of the gartanin compound comprises the following steps of: pulverizing corylus heferopuylla peels and extracting by using 20-25 percent of 30-95 percent alcohol at the temperature of 30-80 DEG C; recovering the alcohol until no alcohol taste exists; extracting by using ethyl acetate; and obtaining the gartanin compound through methods of silica column chromatography, recrystallization, and the like. The compound is a raw material medicine for novel medicine research, mp is 171-172 DEG C, and the productivity reaches 0.4-0.5 percent. The gartanin compound can be applied to preparing medicaments for treating hyperlipidemia.
Description
Technical field
The present invention relates to a kind of medicinal usage of monomeric compound, this chemical compound refers in particular to the gartanin chemical compound.
Background technology
Gartanin chemical compound Chinese is 1,3,5,8-tetrahydroxy-2,4-two (3-methyl-2-butene base)
Ketone.It is the monomeric compound that extraction separation obtains from the Corylus heterophylla Fisch skin.
Fig. 1 is 1,3,5,8-tetrahydroxy-2,4-two (3-methyl-2-butene base)
The ketone structural formula.
Corylus heterophylla Fisch (Corylus heterophylla Fisch) is the kind of hazel.Hazel (Corylusheterophylla Fish.ex Bess.) is Betulaceae (betulaceae) Corylus (corlus) plant, originates in China, has the history in more than 6000 year so far according to textual criticism.Because the wild resource of hazel is abundant, what China was more for many years is to utilize wild resource, along with developing rapidly of cultivation, and the continuous developing in market, existing a spot of cultivation in China some areas in the last few years.At present, hazel in China's cultivation has 12 kinds of Corylus heterophylla Fisch (Corylus heterophylla Fisch), Corylus mandshurica (Corlus mandshurica Batal), cnidocil (Corylus tibetica Batal) etc., it is more and general wherein to distribute with Corylus heterophylla Fisch, in Liaoning, all there is distribution on ground such as Jilin, Heilungkiang, Shanxi, Shandong, Henan.Hazel is the fine tree species of fruit material dual-purpose, not only can produce very precious timber, and can produce first-class nut and be the luxury food of raw material with its kernel.The timber of hazel is hard, and texture, color and luster are attractive in appearance, can do small-sized joiner's material, and its seed kernel oil fragrance is edible, is again the raw material of making soap, wax candle and cosmetics.
Botanical character of hazel and growth distribution: hazel is perennial arbor or shrub, and the height of tree is generally 1.5-2m, and the bark taupe is glossy, 1 year living branch brown, close living fine hair; The perula crineous, the edge hairiness; The leaf alternate, stipule is little, and is caducous; Blade circle, wide avette or obovate, most advanced and sophisticated nearly shape or the circle of cutting, shallow splitting, central sliver is longer, and is gradually sharp, and base portion is heart-shaped or cut shape, and there is irregular heavy sawtooth at the edge; The top is truncate, and there is outstanding blade tip in central authorities; Bottle green above the leaf, below light green color, lateral vein 3-5 is right, mostly is the pinniform vein; Unisexual flower, hermaphroditism, no petal, elder generation's leaf is open, staminate inflorescence is cylindrical, sagging De amentum, the bract that tool majority, imbricate are arranged, there be forked stamen 4-8 piece in each bract, flower pesticide yellow, female flower and are born near the staminate inflorescence, contain in an involucre, only red stigma is outstanding, exposes the bud top when open; Nut 1-6, light brown, cluster or Dan Sheng, bigger, sphere or oval, the about 1.5cm in footpath has 2 of phyllarys, shallow splitting, mitriform, close living pubescence in outside and setiform body of gland.The florescence 4-5 month, the fructescence JIUYUE.Hazel is born in the exsiccant hillside that faces south, hillock, wasteland, roadside and border etc. and locates.Be distributed in Northeast China, North China.
The main component of hazel: the leaf of hazel contains tannin, and the flavone reaction is arranged, and bark contains tannin; Kernel carbohydrate containing, protein, fat; Fruit contains starch; Ye Shang contains alkaloid.The fatty acid of oil is formed Palmic acid, stearic acid, oleic acid and linoleic acid etc.
Hazel has medical value widely: kernel can QI invigorating, whet the appetite, make eye bright.Be used for body void after being ill, lack of appetite is tired.Be decocted in water for oral dose consumption 30-60g.The male flower of hazel has antiinflammatory, detumescence, analgesic effect.Can be used for scytitis, cold injury etc.
Hyperlipemia is person in middle and old age's commonly encountered diseases, and main harm is to cause atherosclerosis, and then causes numerous relevant diseases, and wherein modal a kind of mortality disease is exactly a coronary heart disease.Serious chylomicronemia can cause acute pancreatitis, is another mortality disease.This disease to the infringement of health be concealment, gradually, carrying out property and general.Its direct infringement is to quicken systemic atherosclerosis, because the vitals of whole body all will rely on tremulous pulse blood supply, oxygen supply, in case tremulous pulse is stopped up by atheromatous plaque, will cause serious consequence.The renal failure that arteriosclerosis causes etc., all closely related with hyperlipemia.A large amount of research datas show that hyperlipemia is apoplexy, coronary heart disease, myocardial infarction, cardiac sudden death is independent and important risk.In addition, hyperlipemia also is an important risk factor that promotes hypertension, impaired glucose tolerance, diabetes.Hyperlipemia also can cause fatty liver, liver cirrhosis, cholelithiasis, pancreatitis, retinal hemorrhage, blind, peripheral vascular disease, limping, hyperuricemia.Xanthoma around tendon shape, nodositas, palm plane and the eye socket, arcus juvenilis etc. also can appear in some constitutional and familial hyperlipidemia patient
Hyperlipemia mainly be meant serum total cholesterol (TC) or triglyceride (TG) level too high and (or) serum high-density LP-cholesterol (HDL-C) level is low excessively.Hyperlipemia is person in middle and old age's commonly encountered diseases and a frequently-occurring disease, and along with the raising of people's living standard and the change of living habit, this sick sickness rate obviously increases, and the age of morbidity also shifts to an earlier date to some extent.The caused atherosclerosis of hyperlipemia is to cause the main cause of coronary heart disease, hypertension and cerebrovascular disease, and the whole world has 1,500 ten thousand people to die from cardiovascular diseases and apoplexy every year approximately.So the treatment of hyperlipemia is extremely important, this has caused showing great attention to of the whole mankind.The final purpose of treatment hyperlipemia is to suppress arteriosclerotic further developing, thereby prevents the death that caused by cardio-cerebrovascular diseases.
Rapid-action and curative effect is subjected to everybody favor to the Western medicine that is used for the treatment of hyperlipemia at present certainly because of it, but Western medicine all has toxic and side effects in various degree, and Chinese medicine is in the treatment hyperlipemia, prevent that from there is special advantages aspects such as cardiovascular and cerebrovascular disease generation, its curative effect certainly, continue, side effect is little, is that Western medicine institute is incomparable.Particularly aspect differentiation of symptoms and signs for classification of syndrome, embodied the flexible prescription of the traditional Chinese medical science, the treatment characteristic of giving treatment in accordance with the patient.The modern medicine man generally believes the genus deficiency in origin and excess in superficiality for the understanding of hyperlipemia, blood stasis, and the turbid category of expectorant, ahyperlipoidemia name of disease on the Chinese medicine, clinical syndrome differentiation belongs to caused by liver and kidney deficiency more, and insufficiency of the spleen expectorant is turbid, qi depression to blood stasis.Use liver and kidney tonifying mostly during treatment, invigorating the spleen and benefiting QI, nourishing YIN and benefiting blood, blood circulation promoting and blood stasis dispelling, clearing away heat and loosing the bowels, these medicines eliminate indigestion and phlegm.
In recent years, domestic and international research person is carrying out a large amount of work aspect the research of exploring blood fat reducing Chinese medicine, the bibliographical information flavonoid and
Ketone compounds has hypolipidemic activity, in view of contain more rich flavone compound in Hazel Leaves, in the separation and Extraction process of chemical compound, finds
Ketone compounds Gartanin mainly is distributed in the ethyl acetate part.
Ketone claims the benzo chromone again, is the yellow or colourless phenoloid of a class, has color reaction similar to flavonoid and chromatographic characterization, therefore once is included into the flavonoid discussion, but from its spectral signature
Ketone and flavone are distinguishing.
Ketone itself is not present in plant, and the nature person of existence is its derivant.
The ketone parent nucleus have 8 can substituted position, simple
Ketonic compound mostly is the chemical compound of hydroxyl, methoxyl group replacement, because oxy radical replaces different precedences, and will
Ketonic compound is divided into different oxo types,
Ketone also has methyl substituted except that containing the replacement of oxygen base, isopentene group replaces, and
A pair of horses going side by sides such as ketone nuclear and phenyl ring, furan nucleus are closed, two molecules
Ketonic compound combinations etc. constitute various
Ketonic compound.
Contain a large amount of flavone compounds in the Corylus heterophylla Fisch skin, have stronger biological activity aspect the reduction hyperlipidemia.Gartanin chemical compound exploitation in the resourceful Corylus heterophylla Fisch skin is become atorvastatin, and the hyperlipemic patients crowd at vast is with a wide range of applications.
At present, report is not seen in the application of relevant gartanin chemical compound in preparation treatment hyperlipidemia medicine.
Summary of the invention
The purpose of this invention is to provide the application of gartanin chemical compound in preparation treatment hyperlipidemia medicine.
The preparation method of gartanin chemical compound has had a lot of reported in literature, the invention provides a kind of employing Corylus heterophylla Fisch skin extraction preparation gartanin chemical compound extraction process for purification to be:
A. the Corylus heterophylla Fisch corium farinosum is broken, under 30-80 ℃ of condition, doubly measure the 30%-95% ethanol extraction 3 times with 20-25, be respectively 3h, 2h, 1h at every turn, filter merge extractive liquid;
B. on the extracting solution that step a is obtained, reclaim ethanol, use ethyl acetate extraction, reclaim extract and get ethyl acetate extract to there not being the alcohol flavor.
C. the ethyl acetate extract that step b. is obtained is through silica gel column chromatography, 1) and petroleum ether-acetone (25-1: 1) eluant is chloroform-methanol (15-1:, collect gartanin chemical compound part, reclaim solvent to doing, the chloroform recrystallization gets yellow acicular crystal product, mp 171-172 ℃, productive rate reaches 0.4%-0.5%.
Technical scheme of the present invention is:
The application of gartanin chemical compound in preparation treatment hyperlipidemia medicine.
When the present invention is used to prepare the medicine for the treatment of hyperlipidemia, its oral or parenteral, all be safe, under oral situation, it can any conventionally form administration, as powder, granule, tablet, capsule, pill, solution, suspension, syrup, buccal tablets, sublingual lozenge etc.: when this medicine parenteral, can take any conventionally form, for example injection: as intravenous injection, ointment, suppository, percutaneous dosing, inhalant etc.
It is to be made of effective ingredient monomer or the effective ingredient excipient with solid or liquid that the present invention prepares the medicine for the treatment of hyperlipidemia, the excipient of solid used herein or liquid is well known in the art, lift several object lessons below, powder is the powder agent that takes orally, its excipient has lactose, starch, paste essence, calcium carbonate, synthetic or puritan filler aluminum, magnesium oxide, magnesium stearate, sodium bicarbonate, dry yeast etc.; The excipient of solution has water, glycerol, propylene glycol, simple syrup, ethanol, ethylene glycol, Polyethylene Glycol, Sorbitol etc.; The excipient of ointment can use fatty oil, and agnolin, vaseline, glycerol, Cera Flava, wood are cured, white oil, resin, senior water-repelling agent or the hydrophilizing agent that is combined into such as cured.
The invention has the beneficial effects as follows that the gartanin chemical compound that the Corylus heterophylla Fisch skin obtains belongs to effective ingredient, its medicinal usage belongs to first to be found, for the treatment hyperlipidemia has been found new precursor compound.
The dosage of effective ingredient can be according to the mode of taking, patient's age and body weight and be in a bad way degree and other similar factor and change, and oral dose is: 20～100mg/ time, take for 1～2 time every day: inject 10～30mg/ time, once a day.
The specific embodiment
The present invention can further specify by following experimental example.
The preliminary test of experimental example one, gartanin prevention and treatment hyperlipidemia
1 experiment material
Animal
The ICR mice, 84, male 60, female 24, body weight 18-20g.Available from preclinical medicine institute of Jilin University zoopery center, the animal quality certification number: SCXK-(Ji)-2003-0001.
Medicine and reagent
XUEZHIKANG JIAONANG: specification 300mg/ grain, lot number 20060305, the Beijing WBL Peking University Biotech Co., Ltd produces;
The fenofibrate group: specification 200mg/ grain, lot number 89396, French Li Bofuni drugmaker produces;
Cholesterol: the specification biochemical reagents, the 25g/ bottle, lot number: 070516, Tianjin recovery fine chemistry industry institute;
Sodium cholate: the specification biochemical reagents, lot number: 20070525, Beijing chemical reagents corporation;
Adeps Sus domestica: provide by this research department;
Serum total cholesterol (TC) assay test kit, lot number: 070501, Zhongsheng Beikong Biological Science ﹠ Technology Co., Ltd.;
Triglyceride (TG) assay test kit, lot number: 071831, Zhongsheng Beikong Biological Science ﹠ Technology Co., Ltd.;
HDL-C (HDL-cho) assay test kit, lot number: 070171, Zhongsheng Beikong Biological Science ﹠ Technology Co., Ltd.;
Low-density lipoprotein cholesterol (LDL-cho) assay test kit, lot number: 070171, Zhongsheng Beikong Biological Science ﹠ Technology Co., Ltd.'s product;
Gartanin: yellow acicular crystal (CHCl
3), mp 171-172 ℃.Lot number: 071003, self-control.
Instrument
Microplate reader: model PECAN A-5082, Austria SUNRISE company product.
2 experimental techniques
The high lipid food compound method: reference literature adds 10% Adeps Sus domestica, 1% cholesterol and 0.3% sodium cholate in 88.7% normal feedstuff.Adeps Sus domestica heated dissolve, add cholesterol and sodium cholate, pour in the feedstuff after stirring, mix thoroughly, add an amount of warm water and mix thoroughly, be tiled in the square plate, the about 1.5cm of thickness is divided into the fritter of 2cm * 3cm size with the wallpaper cutter, places in 80 ℃ of thermostatic drying chambers and dries.
Dosage: calculate requirement according to each group dosage, the weight of animals, administration natural law respectively, the accurate title, decide, and adds a small amount of distilled water earlier, grinds evenly, and adding distil water to desired concn gets final product again.
Conformed after animal is bought 3 days, and be divided at random: the normal control group by body weight; The hyperlipidemia model group; Positive control drug XUEZHIKANG JIAONANG group (240mg/kg); Positive control drug fenofibrate group (40mg/kg); Gartanin high dose group (80mg/kg), middle dosage group (40mg/kg) and low dose group (20mg/kg); Totally 7 groups, 12 every group.
In the experimentation, the normal control treated animal is raised with conventional feed, and other each treated animals are all raised with high lipid food.Laboratory animal every morning gastric infusion 1 time.Irritate the long-pending 20ml/kg that is of body of stomach.Normal control group and hyperlipidemia model treated animal are irritated the stomach distilled water, and the administration group gives corresponding drug solution respectively.In 2 weeks of successive administration, on last 1 administration that night, the animal fasting be can't help water 16 hours, and next day, eyeball was got blood 0.5ml, centrifugal (3000r/min) separation of serum; Adopt enzymic colorimetric to measure serum total cholesterol (TC) content, adopt enzymic colorimetric to measure serum triglycerides (TG) content, adopt phosphotungstic acid-magnesium precipitate method to measure serum high-density LP cholesterol (HDL-cho) content, adopt the polyvinyl sulfuric acid sedimentation method to measure serum low-density LP cholesterol (LDL-cho) content.Achievement data with mean add and subtract standard deviation (
) expression, t-check between statistical procedures method employing group.
3 experimental results
Experimental result shows, mice is after raising with 2 weeks of high lipid food modeling continuously, the serum TC of model group animal, TG, LDL-cho content all obviously raise than normal matched group, and TC content normal control group is 3.16 ± 0.48mmol/L, and model group is 6.54 ± 0.84mmol/L (P＜0.01); TG content normal control group is 0.69 ± 0.20mmol/L, and model group is 0.85 ± 0.21mmol/L (P＜0.05); LDL-cho content normal control group is 0.30 ± 0.28mmol/L, and model group is 1.92 ± 1.09mmol/L (P＜0.01); The serum hdl of model group animal-cho content obviously reduces, and the normal control group is 3.90 ± 1.63mmol/L, and model group is 2.40 ± 0.79mmol/L (P＜0.05); The ratio of serum TC of model group animal and HDL-cho content (TC/HDL-cho) obviously raises, and the normal control group is 0.90 ± 0.24, and model group is 2.89 ± 1.53 (P＜0.01); The result shows that the hyperlipidemia animal model forms.
After 2 weeks of administration, (5.53 ± 1.04mmol/L) are starkly lower than hyperlipidemia model group (6.54 ± 0.84mmol/L) (P＜0.05) to Gartanin 80mg/kg dosage treated animal serum TC content; (2.62 ± 1.88mmol/L) relatively have rising trend with the hyperlipidemia model group to administration treated animal serum hdl-cho content, but do not have marked difference (P＞0.05); (1.58 ± 0.87mmol/L) relatively have reduction trend with the hyperlipidemia model group to administration treated animal serum LDL-cho content, but do not have marked difference (P＞0.05); (2.31 ± 1.18mmol/L) relatively have reduction trend with the hyperlipidemia model group to administration treated animal serum TC/HDL-cho ratio, but do not have marked difference (P＞0.05); Administration treated animal serum TG content and hyperlipidemia model group relatively do not have marked difference.
(5.54 ± 1.05mmol/L) are starkly lower than hyperlipidemia model group (6.54 ± 0.84mmol/L) (P＜0.05) to Gartanin 40mg/kg dosage treated animal serum TC content; Administration treated animal serum TG, LDL-cho, HDL-cho content and TC/HDL-cho ratio are compared no marked difference with the hyperlipidemia model group.
Gartanin 20mg/kg dosage treated animal serum TC, TG, LDL-cho, HDL-cho content and TC/HDL-cho ratio are compared no marked difference with the hyperlipidemia model treated animal.
Above-mentioned result of the test shows, extracts the effect that the Gartanin chemical compound has reduction hyperlipidemia model mice serum TC content that obtains in the Hazel Leaves.Each treated animal TC, TG, LDL-cho, HDL-cho content and TC/HDL-cho ratio see Table 1.
The specific embodiment
The present invention can further specify by following experimental example.
The embodiment 1 of extracting method:
A. the Corylus heterophylla Fisch corium farinosum is broken, under 30 ℃ of conditions,, be respectively 3h, 2h, 1h with 25 times of amount 95% ethanol extractions 3 times at every turn, filter merge extractive liquid;
B. on the extracting solution that step a is obtained, reclaim ethanol, use ethyl acetate extraction, reclaim extract and get ethyl acetate extract to there not being the alcohol flavor.
C. the ethyl acetate extract that step b. is obtained is through silica gel column chromatography, 1) and petroleum ether-acetone (25-1: 1) eluant is chloroform-methanol (15-1:, collect gartanin chemical compound part, reclaim solvent to doing, the chloroform recrystallization gets yellow acicular crystal product, mp 171-172 ℃, productive rate reaches 0.45%.
The embodiment 2 of extracting method:
A. the Corylus heterophylla Fisch corium farinosum is broken, under 80 ℃ of conditions,, be respectively 3h, 2h, 1h with 20 times of amount 30% ethanol extractions 3 times at every turn, filter merge extractive liquid;
B. on the extracting solution that step a is obtained, reclaim ethanol, use ethyl acetate extraction, reclaim extract and get ethyl acetate extract to there not being the alcohol flavor.
C. the ethyl acetate extract that step b. is obtained is through silica gel column chromatography, 1) and petroleum ether-acetone (25-1: 1) eluant is chloroform-methanol (15-1:, collect gartanin chemical compound part, reclaim solvent to doing, the chloroform recrystallization gets yellow acicular crystal product, mp171-172 ℃, productive rate reaches 0.5%.
The embodiment 3 of extracting method:
A. the Corylus heterophylla Fisch corium farinosum is broken, under 45 ℃ of conditions,, be respectively 3h, 2h, 1h with 22 times of amount 55% ethanol extractions 3 times at every turn, filter merge extractive liquid;
B. on the extracting solution that step a is obtained, reclaim ethanol, use ethyl acetate extraction, reclaim extract and get ethyl acetate extract to there not being the alcohol flavor.
C. the ethyl acetate extract that step b. is obtained is through silica gel column chromatography, 1) and petroleum ether-acetone (25-1: 1) eluant is chloroform-methanol (15-1:, collect gartanin chemical compound part, reclaim solvent to doing, the chloroform recrystallization gets yellow acicular crystal product, mp 171-172 ℃, productive rate reaches 0.4%.
The embodiment 1 of preparation medicament:
Get gartanin chemical compound 20g, add medical starch 280g, the two fully mixes, and makes 1000 capsules, and every heavy 0.3g contains gartanin 20mg.
The embodiment 2 of preparation medicament:
Get gartanin chemical compound 100g, add medical starch 200g, the two fully mixes, and makes 1000, and every heavy 0.3g contains gartanin 100mg.
The embodiment 3 of preparation medicament:
Get gartanin chemical compound 20g, add 1,2-propylene glycol 100ml, heating for dissolving,, thin up is dressed up 1000 bottles to 1000ml, and every bottle of 1ml contains gartanin20mg.
Claims (1)
1.gartanin the application of chemical compound in preparation treatment hyperlipidemia medicine.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102204942A (en) * | 2011-05-24 | 2011-10-05 | 黑龙江大学 | Method for extracting corylus heterophylla leaf flavone |
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| US6730333B1 (en) * | 2002-10-30 | 2004-05-04 | Dbc, Llc | Nutraceutical mangosteen composition |
| JP2009013105A (en) * | 2007-07-04 | 2009-01-22 | Yoshihiro Futamura | Xanthone derivatives having collagen-increasing action, method for producing the same, cosmetics and food preparation comprising the derivatives |
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2009
- 2009-04-24 CN CN200910066864.2A patent/CN101869559B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6730333B1 (en) * | 2002-10-30 | 2004-05-04 | Dbc, Llc | Nutraceutical mangosteen composition |
| JP2009013105A (en) * | 2007-07-04 | 2009-01-22 | Yoshihiro Futamura | Xanthone derivatives having collagen-increasing action, method for producing the same, cosmetics and food preparation comprising the derivatives |
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| TOSHIHIRO MIURA, ET AL.: "The suppressive effect of mangiferin with exercise on blood lipids in type 2 diabetes", 《BIOL. PHARM. BULL.》 * |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102204942A (en) * | 2011-05-24 | 2011-10-05 | 黑龙江大学 | Method for extracting corylus heterophylla leaf flavone |
| CN102204942B (en) * | 2011-05-24 | 2012-12-05 | 黑龙江大学 | Method for extracting corylus heterophylla leaf flavone |
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Inventor after: Xing Hongcun Inventor after: Li Pingya Inventor after: Liu Jinping Inventor after: Lu Dan Inventor after: Xue Jianfei Inventor before: Li Pingya Inventor before: Liu Jinping Inventor before: Lu Dan Inventor before: Xue Jianfei |
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