CN103585166A - Medical applications of flavonol derivatives - Google Patents
Medical applications of flavonol derivatives Download PDFInfo
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- CN103585166A CN103585166A CN201210437298.3A CN201210437298A CN103585166A CN 103585166 A CN103585166 A CN 103585166A CN 201210437298 A CN201210437298 A CN 201210437298A CN 103585166 A CN103585166 A CN 103585166A
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Abstract
The invention relates to the pharmaceutical field, and especially relates to medical applications of flavonol derivatives with the structural formula (I), wherein R1 and R2 are selected from hydroxyl or 2,6-dimethyl-6-hydroxyl-2,7-octadiene acyl independently; R3 is selected from hydrogen or methoxyl; R4 is selected from hydroxyl or XCH2(CHOH)4CO-, when R4 is XCH2(CHOH)4CO-, X is selected from hydroxyl or erucic acyl. The flavonol derivatives with the structural formula (I), or pharmaceutically acceptable salts, hydrates or prodrug thereof can be used for treating hyperlipemia.
Description
Technical field
The invention belongs to pharmaceutical field, particularly relate to a kind of medical usage of flavol ketone derivatives.
Background technology
Hyperlipemia, with the feature of changing into of various lipoprotein spectrums in blood plasma, comprises that blood T-CHOL (TC) level raises, triglyceride (TG) level raises, high density lipoprotein (HDL-C) level reduces and low density lipoprotein, LDL (LDL-C) level raises.Hyperlipemia is easily induced arterial wall generation atherosclerotic lesion, increases the unstability of speckle, finally causes the generation of acute cardiovascular disease.
At present, the more lipid lowerers of clinical practice is statins, although such curative effect of medication is remarkable, long-term taking has certain toxic and side effects, and as musclar toxicity, dysbolismus, the intestines and stomach reaction etc., the serious liver transaminase that also can cause raises.On market, blood fat reducing class tcm product is mainly three kinds of Xuezhikang, zhibituo and Herb Gynostemmae Pentaphylli total glycosides, and wherein the above two main component is all the Monacolins that utilize herb fermenting technology to obtain from Qu Hongzhong.And other blood fat reducing class tcm products are mostly compound recipe class preparation, the shortcoming such as ubiquity active chemical is unintelligible, study on mechanism weakness.So finding new hypolipidemic activity composition from plant is an important research direction.
Fructus Hippophae (Hippophae rhamnoides L) has another name called vinegar willow, belongs to Elaeangnaceae Hippophae, machaka or dungarunga, nature and flavor " sour, puckery, temperature ", have the effect ，Xi Mongols, Tibetan's conventional crude drugs of " eliminating phlegm and stopping cough, relieving dyspepsia; blood circulation promoting and blood stasis dispelling ".1977, Fructus Hippophae was formally listed in < < Chinese Pharmacopoeia > >, and the eighties in 20th century, Fructus Hippophae is classified as first medicine food dual purpose plant kind of China by health ministry.
Summary of the invention
First the present invention provides the flavonol derivant of a kind of structural formula (I), or the application in preparing blood lipid-lowering medicine of its pharmaceutically acceptable salt, hydrate or prodrug, and wherein structural formula (I) is:
R wherein
1and R
2independently selected from hydroxyl or 2,6-dimethyl-6-hydroxyl-2,7-octadiene acyl group;
R
3be selected from hydrogen or methoxyl group;
R
4be selected from hydroxyl or XCH
2(CHOH)
4cO-, works as R
4for XCH
2(CHOH)
4during CO-, X is selected from hydroxyl or mustard acyl.
The present invention also comprises corresponding all pharmaceutically acceptable salt, hydrate or the prodrug of above-claimed cpd.These salt can be positively charged in compound part (for example, amido) with there is contrary electrical electronegative (for example, trifluoracetic acid) and form; Or part (for example, completing base) electronegative in compound for example, forms with positive charge (, sodium, potassium, calcium, magnesium).Compound can contain a nonaromatic pair of key, has one or more asymmetric centers.So these compounds can be used as racemic mixture, independent enantiomer, independent diastereomer, non-enantiomer mixture, cis or transisomer existence.All these isomers are all expected.Described " prodrug of the flavonol derivant of structural formula (I) " is often referred to a kind of material, after using by suitable method, can in subject, carry out metabolism or chemical reaction and be transformed at least one compound or its salt of structural formula (I).
Comparatively preferably, the R of the flavonol derivant of said structure formula (I)
1and R
2when different, be 2,6-dimethyl-6-hydroxyl-2,7-octadiene acyl group.
More preferably, some concrete compounds of structural formula of the present invention (I) are:
Compound 1
Compound 2
Compound 3
Compound 4
Compound 5
Compound 6
Compound 7
The flavonol derivant of structural formula of the present invention (I) can be by this area conventional method from the plants such as Fructus Hippophae, extract acquisition as alcohol extraction, chromatography etc., also can buy or utilize marketable material by commercial sources, by compou nd synthesis method traditional in prior art is synthetic, obtain.Those of ordinary skill in the art can synthesize compound of the present invention according to existing known technology.Synthetic compound can further be further purified by modes such as column chromatography, high performance liquid chromatography or crystallizations.
Synthetic chemistry transformation, protection functional group methodology (protect or go and protect) are helpful to synthetic application compound, and be technology commonly known in the art, as R.Larock, Comprehensive OrganicTransformations, VCH Publishers (1989); T.W.Greene and P.G.M.Wuts, Protective Groups in Organic Synthesis, 3
rded., John Wiley and Sons (1999); L. Fieser and M.Fieser, Fieser and Fieser ' s Reagents for Organic Synthesis, John Wiley and Sons (1994); And L.Paquette, ed., Encyclopedia of Reagents for Organic Synthesis, has open in John Wiley and Sons (1995).
The flavonol derivant of structural formula of the present invention (I) or its pharmaceutically acceptable salt, hydrate or prodrug can effectively reduce the blood lipid level of animal.So flavonol derivant of the present invention or its pharmaceutically acceptable salt, hydrate or prodrug can be used for preparing the medicine of blood fat reducing.
Flavonol derivant or its pharmaceutically acceptable salt, hydrate or the prodrug of structural formula of the present invention (I) can be prepared into pharmaceutical composition, said composition comprises one or more flavonol derivant of the present invention or its pharmaceutically acceptable salt, hydrate or prodrugs, with pharmaceutically acceptable carrier, said composition can be used for treating hyperlipemia;
Flavonol derivant or its pharmaceutically acceptable salt, hydrate or the prodrug of structural formula of the present invention (I) can be prepared into pharmaceutical preparation, this pharmaceutical preparation comprises flavonol derivant or its pharmaceutically acceptable salt, hydrate or the prodrug of one or more structural formulas of the present invention (I), and this pharmaceutical preparation can be used for treating hyperlipemia.
The flavonol derivant of described structural formula (I) or its pharmaceutically acceptable salt, hydrate or the prodrug content in compositions or pharmaceutical preparation is 0.0001-50wt% for example; 0.001-30wt% preferably; Better 0.01-20wt%.
The compound of the structural formula of the present invention (I) for the treatment of effective dose (that is: can produce function or amount active and that can be accepted by people and/or animal to people and/or animal) and the acceptable carrier (carrier that is used for the treatment of administration pharmaceutically, they itself are not necessary active component, and after using, there is no undue toxicity) to form pharmaceutical preparation, these pharmaceutical preparatioies can be prepared into oral formulations, injection, tablet, powder preparation, capsule, dispersible tablet, slow releasing preparation etc.
The consumption of the pharmaceutical composition of the present invention for the treatment of effective dose is between 0.001-500mg/kg body weight/day, and any consumption within above-mentioned scope is all effective dose of the present invention.Preferably, the consumption of compositions of the present invention is between 0.005-300mg/kg body weight/day; Preferred, the consumption of compositions of the present invention is between 0.01-100mg/kg body weight/day.Described " treatment effective dose " can be used for single drug or the drug combination treatment of relevant disease.One of skill in the art can understand, and the consumption when actual administration can be higher or lower than above-mentioned dosage range.For " the treatment effective dose " of a certain object (as mammal-people) and concrete therapeutic scheme, can be subject to the impact of factors, comprise the drug activity of compound used therefor or its prodrug, age, body weight, ordinary circumstance, sex, diet, administration time, disease susceptibility, the disease process of administration object and the judgement etc. of accepting doctor for medical treatment.Described " treatment " refers to the flavonol derivant that gives one or more structural formulas of the present invention (I) of body (contain tumor, have the symptom of tumor or have the omen of tumor), to treat, alleviate, slow down, change, cure, affect, to improve the symptom of its hyperlipemia, hyperlipemia or the omen of hyperlipemia.
The compound of structural formula of the present invention (I) or its pharmaceutically acceptable salt, hydrate or prodrug or its compositions or its pharmaceutical preparation can be by administrations such as oral, intravenous, intramuscular, subcutaneous, nasal cavity, internal rectum.Solid carrier is as starch, lactose, phosphoric acid glycol, microcrystalline Cellulose, nigecose and kaolin, and liquid carrier is as sterilized water, Polyethylene Glycol, nonionic surfactant and edible oil (as Semen Maydis oil, Oleum Arachidis hypogaeae semen and Oleum sesami), as long as be applicable to characteristic and the needed specific administration mode of active component.In pharmaceutical compositions, normally used adjuvant also can advantageously be included, as, flavoring agent, pigment, antiseptic and antioxidant are as vitamin E, vitamin C, BHT and BHA.
These reactive compounds also can parenteral or intraperitoneal administration.Also can in the water that is suitably mixed with surfactant (as hydroxypropyl cellulose), prepare solution or the suspension of these reactive compounds (as free alkali or pharmaceutically acceptable salt).Also can in glycerol, Polyethylene Glycol and the mixture in oil thereof, prepare dispersion liquid.Under conventional storage and service condition, in these preparations, contain antiseptic to prevent microbial growth.
The medicament forms that is applicable to injection comprises: aseptic aqueous solution or dispersion liquid and aseptic powder (for prepare aseptic parenteral solution or dispersion liquid temporarily).In all situations, these forms must be aseptic and must be that fluid is discharged fluid to be easy to syringe.Under manufacture and condition of storage, must be stable, and must be able to prevent that microorganism is as the pollution of antibacterial and fungus and impact.Carrier can be solvent or disperse medium, wherein contains just like water, alcohol, their suitable mixture and vegetable oil.
The details of various aspects of the present invention will be able to detailed description in chapters and sections subsequently.By below and the description of claim, feature of the present invention, object and advantage will be more obvious.
The specific embodiment
Below in conjunction with specific embodiment, further set forth the present invention.Should be understood that these embodiment are only not used in and limit the scope of the invention for the present invention is described.The experimental technique of unreceipted actual conditions in the following example, conventionally according to normal condition or the condition of advising according to manufacturer.Unless otherwise indicated, otherwise all percent, ratio, ratio or umber by weight.
Unless otherwise defined, the same meaning that all specialties of using in literary composition and scientific words and one skilled in the art are familiar.In addition, any method similar or impartial to described content and material all can be applicable in the inventive method.The use that better implementation method described in literary composition and material only present a demonstration.
The above-mentioned feature that the present invention mentions, or the feature that embodiment mentions can combination in any.All features that patent specification discloses can with any composition forms use, each feature disclosing in description, can anyly provide the alternative characteristics of identical, impartial or similar object to replace.Therefore except there being special instruction, the feature disclosing is only the general example of equalization or similar features.
Embodiment 1 extracts compound 1
1) extract monomer component
Get Chinese crude drug seed of Fructus Hippophae 1000g, with 8 times of 75% alcohol reflux 2 hours, be concentrated into and do and obtain extract, 3: 0.5 gradient elutions) and reversed-phase silica gel column chromatography (400 orders silica gel column chromatography (400 orders, 30 times of extract qualities, chloroform: methanol: water=8: 2: 0.2-7: repeatedly continuously, 50 times of extract qualities, methanol: water=3: 7-5: 5 gradient elutions), separation obtains compound 10.05g, yield 0.005%.
2) Structural Identification
Through MS-ESI, 13C-NMR, 1H-NMR, measure, obtain the spectral data of this compound 1.
ESI-MS (m/z): 617.20[M+Na]+(positive), 593.21[M-H]-(negative), molecular formula: C27H30O15, 1H-NMR (DMSO-d6,500MHz): 6.44 (1H, s, H-6), 6.83 (1H, s, H-8), 8.08 (2H, d, J=8.8Hz, H-2 ', 6 '), 6.89 (2H, d, J=8.8Hz, H-3 ', 5 '), 5.55 (1H, s, Rha-1), 5.49 (1H, d, J=7.5Hz, Glc-1), 13C-NMR (DMSO-d6, 125MHz): 156.8 (C-2), 133.5 (C-3), 177.7 (C-4), 160.2 (C-5), 99.6 (C-6), 161.6 (C-7), 94.5 (C-8), 156.0 (C-9), 105.7 (C-10), 120.8 (C-1 '), 131.1 (C-2 ', 6 '), 115.2 (C-3 ', 5 '), 160.9 (C-4 '), 100.7 (Glc-1), 74.3 (Glc-2), 76.5 (Glc-3), 70.3 (Glc-4), 77.6 (Glc-5), 60.9 (Glc-6), 98.4 (Rha-I), 70.1 (Rha-2), 70.0 (Rha-3), 71.6 (Rha-4), 69.9 (Rha-5), 18.0 (Rha-6).
Embodiment 2 extracts and authenticating compound 2-7
Compound 2～7th, the similar method of applicating adn implementing example 1 is extracted.Through MS-ESI, 13C-NMR, 1H-NMR, measure, obtain the following spectral data of these compounds.
Compound 2
ESI-MS (m/z): 647.23[M+Na]+(positive), 623.26[M-H]-(negative), molecular formula: C28H32O16, 1H-NMR (DMSO-d6,500MHz): 6.34 (1H, s, H-6), 6.70 (1H, s, H-8), 7.89 (1H, s, H-2 '), 6.70 (1H, d, J=-6.5Hz, H-5 '), 7.55 (1H, d, J=6.5Hz, H-6 '), 5.53 (1H, s, Rha-1), 5.50 (1H, d, J=7.2Hz, Glc-1), 13C-NMR (DMSO-d6, 125MHz): 1 57.2 (C-2), 132.4 (C-3), 176.6 (C-4), 160.2 (C-5), 99.0 (C-6), 161.6 (C-7), 94.8 (C-8), 156.0 (C-9), 105.8 (C-10), 120.8 (C-1 '), 112.8 (C-2 '), 148.2 (C-3 '), 150.2 (C-4 '), 114.8 (C-5 '), 122.7 (C-5 '), 100.1 (Glc-1), 74.4 (Glc-2), 76.5 (Glc-3), 70.3 (Glc-4), 77.5 (Glc-5), 60.7 (Glc-6), 98.2 (Rha-1), 70.0 (Rha-2), 70.0 (Rha-3), 7 1.7 (Rha-4), 69.9 (Rha-5), 1 8.0 (Rha-6),
Compound 3
Compound 4
ESI-MS (m/z): 779.20[M+Na]+(positive), 755.02[M-H]
-(negative), molecular formula: C
33h
40o
20,
1h-NMR (DMSO-d
6, 500MHz): 6.42 (1H, d, J=1.5Hz, H-6), 6.82 (1H, d, J=1.5 Hz, H-8), 8.09 (2H, d, J=9.0Hz, H-2 ', 6 '), 6.90 (2H, d, J=9.0Hz, H-3 ', 5 '), 5.51 (1H, s, Rha-1), 5.71 (1H, d, J=6.5Hz, Glc I-1), 4.59 (1H, d, J=7.0Hz, Glc II-1),
13c-NMR (DMSO-d
6, 125MHz): 156.0 (C-2), 133.1 (C-3), 177.6 (C-4), 161.0 (C-5), 99.4 (C-6), 161.6 (C-7), 94.4 (C-8), 156.3 (C-9), 105.7 (C-10), 120.2 (C-1 '), 131.2 (C-2 ', 6 '), 115.6 (C-3 ', 5 '), 161.0 (C-4 '), 98.4 (Glc I-1), 82.4 (Glc I-2), 76.7 (Glc I-3), 69.6 (Glc I-4), 76.6 (Glc I-5), 60.6 (Glc I-6), 104.2 (Glc II-1), 74.7 (Glc II-2), 77.1 (Glc II-3), 70.3 (Glc II-4), 77.6 (Glc II-5), 60.8 (Glc II-6), 98.0 (Rha-1), 69.9 (Rha-2), 70.1 (Rha-3), 71.7 (Rha-4), 69.7 (Rha-5), 18.0 (Rha-6),
Compound 5 and compound 6
Compound 7
ESI-MS (m/z): 985.22[M+Na]+(positive), 960.98[M-H]-(negative), molecular formula: C44H50O24, 1H-NMR (DMSO-d6,500MHz): 6.35 (1H, s, H-6), 6.73 (1H, s, H-8), 8.02 (2H, d, J=9.0Hz, H-2 ', 6 '), 6.90 (2H, d, J=9.0Hz, H-3 ', 5 '), 6.73 (2H, s, H-2 ", 6 "), 7.32 (2H, d, J=15.5Hz, H-α), 6.22 (2H, d, J=15.5Hz, H-β), 3.71 (6H, s, 3 ", 5 " OCH3), 5.51 (1H, s, Rha-1), 5.71 (1H, d, J=6,5Hz, Glc I-1), 4.59 (1H, d, J=7.0Hz, Glc II-1), 13C-NMR (DMSO-d6, 125MHz): 155.8 (C-2), 133.2 (C-3), 177.6 (C-4), 161.5 (C-5), 99.3 (C-6), 161.5 (C-7), 94.1 (C-8), 156.2 (C-9), 105.6 (C-10), 120.6 (C-1 '), 131.1 (C-2 ', 6 '), 115.3 (C-3 ', 5 '), 161.5 (C-4 '), 120.6 (C-1 "), 105.8 (C-2 ", 6 "), 147.8 (C-3 ", 5 "), 138.2 (C-4 "), 145.2 (C-α positions), 114.4 (C-β positions), 166.5 (CO-), 55.9 (C3 ", 5 " OCH3), 98.1 (GlcI-1), 83.4 (Glc I-2), 76.3 (Glc I-3), 69.8 (Glc I-4), 76.5 (Glc I-5), 60.5 (Glc I-6), 104.6 (Glc II-1), 74.6 (Glc II-2), 77.5 (Glc II-3), 70.4 (Glc II-4), 74.0 (Glc II-5), 63.3 (Glc II-6), 98.4 (Rha-1), 70.1 (Rha-2), 70.3 (Rha-3), 71.7 (Rha-4), 69.9 (Rha-5), 18.0 (Rha-6),
The mensuration of embodiment 3 compound 1～7 external hypolipidemic activities
Laboratory animal: male KM mice, body weight 25-30g
Dosage: the test dose of compound 1～10 is 10mg/kg, positive drug simvastatin is 10mg/kg.
Emulsion preparation: Adeps Sus domestica 80g is placed in to 500ml beaker and heating and melting on electric furnace, add cholesterol 40g and make it to dissolve, add again sodium cholate 8g and propylthiouracil sheet 4g, fully stir evenly, then add appropriate distilled water and tween 80, each 80ml of propylene glycol, constantly stir evenly, then add distilled water to 400ml fully mixing, the lipomul of 100g/l cholesterol, 200g/l Adeps Sus domestica, 20g/l sodium cholate and 10g/l propylthiouracil.Put into Refrigerator store, the used time needs heating and melting.
Experimental technique: except Normal group, all the other are respectively organized and gavage Emulsion (0.5ml) every afternoon, the morning next day oral administration, continuous 10d, last day eye socket arterial blood drawing.After centrifuging and taking serum, survey hyperlipemia in mice serum cholesterol (CHO), two biochemical indicators of low density lipoprotein, LDL (LDL).
Experimental result:
Above result of the test shows that compound 1～7 all has effect for reducing blood fat significantly, when 10mg/kg and the lipid-lowering effect of simvastatin approach.
Many aspects involved in the present invention have been done as above and have been set forth.Yet, it should be understood that before not departing from spirit of the present invention and put, those skilled in the art can be equal to and change and modify it, and described change and modification fall into the coverage of the claim of present patent application equally.
Claims (3)
1. a flavonol derivant for structural formula (I), or its pharmaceutically acceptable salt, hydrate or the prodrug application in preparing blood lipid-lowering medicine:
R wherein
1and R
2independently selected from hydroxyl or 2,6-dimethyl-6-hydroxyl-2,7-octadiene acyl group;
R
3be selected from hydrogen or methoxyl group;
R
4be selected from hydroxyl or XCH
2(CHOH)
4cO-, works as R
4for XCH
2(CHOH)
4during CO-, X is selected from hydroxyl or mustard acyl.
2. the purposes of claim 1, is characterized in that, described R
1and R
2when different, be 2,6-dimethyl-6-hydroxyl-2,7-octadiene acyl group.
3. the purposes of claim 2, is characterized in that, described flavonol derivant is selected from:
Compound 1
Compound 2
Compound 3
Compound 4
Compound 5
Compound 6
Compound 7.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108676013A (en) * | 2018-06-25 | 2018-10-19 | 中国医学科学院医药生物技术研究所 | Flavol ketone compounds, preparation method with autophagy Activation Activity and its pharmacy application |
| CN112353810A (en) * | 2020-11-23 | 2021-02-12 | 湖州师范学院求真学院 | Application of compound F-B in preparation of product for preventing and/or treating heart injury |
| CN112608306A (en) * | 2020-12-22 | 2021-04-06 | 河南中医药大学 | Preparation method and application of flavonoid saponin new ketone A in spina gleditsiae |
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| JP2004217545A (en) * | 2003-01-10 | 2004-08-05 | Univ Nihon | New flavonoid glycoside and use thereof |
| CN1837202A (en) * | 2006-04-25 | 2006-09-27 | 中国人民解放军第二军医大学 | Flavonols with blood-fat-lowering effect |
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| JP2004217545A (en) * | 2003-01-10 | 2004-08-05 | Univ Nihon | New flavonoid glycoside and use thereof |
| CN1837202A (en) * | 2006-04-25 | 2006-09-27 | 中国人民解放军第二军医大学 | Flavonols with blood-fat-lowering effect |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108676013A (en) * | 2018-06-25 | 2018-10-19 | 中国医学科学院医药生物技术研究所 | Flavol ketone compounds, preparation method with autophagy Activation Activity and its pharmacy application |
| CN112353810A (en) * | 2020-11-23 | 2021-02-12 | 湖州师范学院求真学院 | Application of compound F-B in preparation of product for preventing and/or treating heart injury |
| CN112353810B (en) * | 2020-11-23 | 2023-08-25 | 湖州师范学院求真学院 | Use of compound F-B in preparation of products for preventing and/or treating heart injury |
| CN112608306A (en) * | 2020-12-22 | 2021-04-06 | 河南中医药大学 | Preparation method and application of flavonoid saponin new ketone A in spina gleditsiae |
| CN112608306B (en) * | 2020-12-22 | 2022-06-03 | 河南中医药大学 | Preparation method and application of flavonoid saponin new ketone A in spina gleditsiae |
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| CN103585166B (en) | 2016-04-20 |
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