CN103585166B - The medical usage of flavol ketone derivatives - Google Patents
The medical usage of flavol ketone derivatives Download PDFInfo
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Abstract
The present invention relates to pharmaceutical field, particularly relate to the medical usage of the flavonol derivant of a kind of structural formula (I):
wherein R
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 flavonol derivant of structural formula of the present invention (I), or its pharmaceutically acceptable salt, hydrate or prodrug 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 changes into feature with lipoprotein spectrum various in blood plasma, comprises the rising of blood T-CHOL (TC) level, triglyceride (TG) level raises, high density lipoprotein (HDL-C) level reduces and low density lipoprotein, LDL (LDL-C) level raises.Hyperlipemia easily induces 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 transaminases that also can cause raises.Blood fat reducing class tcm product mainly Xuezhikang, zhibituo and Herb Gynostemmae Pentaphylli total glycosides three kinds on market, wherein the above two main component is all the Monacolins utilizing herb fermenting technology to obtain from Qu Hongzhong.The shortcomings such as and other blood fat reducing class tcm products are mostly compound recipe class preparation, ubiquity active chemical is unintelligible, and study on mechanism is weak.So finding new hypolipidemic activity composition from plant is an important research direction.
Fructus Hippophae (HippophaerhamnoidesL) has another name called vinegar willow, belongs to Elaeangnaceae Hippophae, machaka or dungarunga, nature and flavor " sour, puckery, warm ", have the effect of " eliminating phlegm and stopping cough, relieving dyspepsia; blood circulation promoting and blood stasis dispelling ", are the Mongols, Tibetan's conventional crude drugs.1977, Fructus Hippophae was formally listed in " Chinese Pharmacopoeia ", the eighties in 20th century, and Fructus Hippophae is classified as first medicine food dual purpose plant kind of China by health ministry.
Summary of the invention
The present invention provide firstly the flavonol derivant of a kind of structural formula (I), or its pharmaceutically acceptable salt, hydrate or prodrug are preparing the application in blood lipid-lowering medicine, and wherein structural formula (I) is:
Wherein R
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 all accordingly pharmaceutically acceptable salt of above-claimed cpd, hydrate or prodrug.These salt can be formed by part (such as, amido) positively charged in compound and electronegative (such as, the trifluoracetic acid) with opposite-sign; Or formed by part (such as, completing base) electronegative in compound and positive charge (such as, sodium, potassium, calcium, magnesium).Compound can contain a nonaromatic double bond, has one or more asymmetric center.So these compounds can exist as racemic mixture, independent enantiomer, independent diastereomer, non-enantiomer mixture, cis or transisomer.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, metabolism or chemical reaction can be carried out and be transformed at least one compound or its salt of structural formula (I) in subject.
Comparatively preferably, the R of the flavonol derivant of structure above (I)
1and R
2be asynchronously 2,6-dimethyl-6-hydroxyl-2,7-octadiene acyl groups.
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) obtains as alcohol extraction, chromatography etc. extract from the plants such as Fructus Hippophae by the conventional method of this area, also buy by commercial sources or utilize marketable material, being obtained by compou nd synthesis method traditional in prior art synthesis.Those of ordinary skill in the art can synthesize compound of the present invention according to existing known technology.The compound of synthesis can be further purified further by modes such as column chromatography, high performance liquid chromatography or crystallizations.
Synthetic chemistry transformation, protection functional group methodology (protect or go protection) are helpful to synthesis application compound, and be technology commonly known in the art, as R.Larock, ComprehensiveOrganicTransformations, VCHPublishers (1989); T.W.GreeneandP.G.M.Wuts, ProtectiveGroupsinOrganicSynthesis, 3
rded., JohnWileyandSons (1999); L.FieserandM.Fieser, FieserandFieser ' sReagentsforOrganicSynthesis, JohnWileyandSons (1994); Have open in andL.Paquette, ed., EncyclopediaofReagentsforOrganicSynthesis, JohnWileyandSons (1995).
The flavonol derivant of structural formula of the present invention (I) or its pharmaceutically acceptable salt, hydrate or prodrug effectively can 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 the medicine preparing 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 such as 0.0001-50wt%; Preferably 0.001-30wt%; Better 0.01-20wt%.
Treatment effective dose (that is: can to people and/or animal produce function or activity and can by people and/or animal the amount that accepts) the compound of structural formula of the present invention (I) (be used for the treatment of the carrier of administration with pharmaceutically acceptable carrier, 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 higher or lower than above-mentioned dosage range.Can by the impact of factors for " the treatment effective dose " of a certain object (as mammal-people) and concrete therapeutic scheme, comprise the drug activity of compound used therefor or its prodrug, age of administration object, body weight, ordinary circumstance, sex, diet, administration time, disease susceptibility, disease process and accept the judgement etc. of doctor for medical treatment.Described " treatment " refers to the flavonol derivant giving body (containing tumor, have the symptom of tumor or have the omen of tumor) one or more structural formulas of the present invention (I), to treat, to alleviate, to slow down, to change, to cure, to affect, to improve its hyperlipemia, the symptom of 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 by the 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 the characteristic of active component and required specific administration mode.In pharmaceutical compositions, normally used adjuvant also can advantageously be included, and e.g., 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 solution or the suspension of these reactive compounds (as free alkali or pharmaceutically acceptable salt) can be prepared in the water being suitably mixed with surfactant (as hydroxypropyl cellulose).Also can prepare dispersion liquid in glycerol, Polyethylene Glycol and the mixture in oil thereof.Under conventional storage and service condition, contain antiseptic in these preparations to prevent microbial growth.
The medicament forms being applicable to inject comprises: aseptic aqueous solution or dispersion liquid and aseptic powder (for extemporaneous preparation of sterile injection or dispersion liquid).In all situations, these forms must be aseptic and must be that fluid is to be easy to syringe displacement fluids.Must be stable under conditions of manufacture and storage, and microorganism must be able to be prevented as the pollution of antibacterial and fungus and impact.Carrier can be solvent or disperse medium, wherein containing, for example water, alcohol, their suitable mixture and vegetable oil.
The details of various aspects of the present invention is able to detailed description by chapters and sections subsequently.By hereafter and the description of claim, feature of the present invention, object and advantage will be more obvious.
Detailed description of the invention
Below in conjunction with specific embodiment, set forth the present invention further.Should be understood that these embodiments are only not used in for illustration of the present invention to limit the scope of the invention.The experimental technique of unreceipted actual conditions in the following example, the usually conveniently conditioned disjunction condition of advising according to manufacturer.Unless otherwise indicated, otherwise all percent, ratio, ratio or number by weight.
Unless otherwise defined, all specialties used in literary composition and scientific words and one skilled in the art the same meaning be familiar with.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 is mentioned can combination in any.All features that patent specification discloses can with any composition forms and use, each feature disclosed in description, anyly can provide identical, alternative characteristics that is impartial or similar object replaces.Therefore apart from special instruction, the feature disclosed is only general example that is impartial or similar features.
Embodiment 1 extracts compound 1
1) monomer component is extracted
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, continuous silica gel column chromatography (400 orders, 30 times of extract qualities, chloroform: methanol: water=8: 2: 0.2-7: 3: 0.5 gradient elution) and reversed-phase silica gel column chromatography (400 orders repeatedly, 50 times of extract qualities, methanol: water=3: 7-5: 5 gradient elutions), be separated and obtain compound 10.05g, yield 0.005%.
2) Structural Identification
Measure through MS-ESI, 13C-NMR, 1H-NMR, 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 is extracted and authenticating compound 2-7
Compound 2 ~ 7 is that the similar method of applicating adn implementing example 1 is extracted.Measure through MS-ESI, 13C-NMR, 1H-NMR, 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): 157.2 (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), 71.7 (Rha-4), 69.9 (Rha-5), 18.0 (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=1.5Hz, 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, GlcI-1), 4.59 (1H, d, J=7.0Hz, GlcII-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 (GlcI-1), 82.4 (GlcI-2), 76.7 (GlcI-3), 69.6 (GlcI-4), 76.6 (GlcI-5), 60.6 (GlcI-6), 104.2 (GlcII-1), 74.7 (GlcII-2), 77.1 (GlcII-3), 70.3 (GlcII-4), 77.6 (GlcII-5), 60.8 (GlcII-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, GlcI-1), 4.59 (1H, d, J=7.0Hz, GlcII-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 (GlcI-2), 76.3 (GlcI-3), 69.8 (GlcI-4), 76.5 (GlcI-5), 60.5 (GlcI-6), 104.6 (GlcII-1), 74.6 (GlcII-2), 77.5 (GlcII-3), 70.4 (GlcII-4), 74.0 (GlcII-5), 63.3 (GlcII-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 the external hypolipidemic activity of embodiment 3 compound 1 ~ 7
Laboratory animal: male KM mice, body weight 25-30g
Dosage: the test dose of compound 1 ~ 10 is 10mg/kg, and positive drug simvastatin is 10mg/kg.
Emulsion prepare: Adeps Sus domestica 80g is placed in 500ml beaker and on electric furnace heating and melting, add cholesterol 40g and make it to dissolve, add sodium cholate 8g and propylthiouracil sheet 4g again, fully stir evenly, then appropriate distilled water and tween 80, each 80ml of propylene glycol is added, constantly stir evenly, then add distilled water to 400ml and 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), low density lipoprotein, LDL (LDL) two biochemical indicators.
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 close.
Many aspects involved in the present invention have been done and have as above been set forth.It is to be understood, however, that put before not departing from spirit of the present invention, those skilled in the art can carry out equivalent change and modification to it, and described change and modification fall into the coverage of the claim of present patent application equally.
Claims (1)
1. flavonol derivant or its pharmaceutically acceptable salt are preparing the application in blood lipid-lowering medicine, and described flavonol derivant is selected from:
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| CN108676013B (en) * | 2018-06-25 | 2021-01-01 | 中国医学科学院医药生物技术研究所 | Flavonol ketone compound with autophagy activation activity, preparation method and pharmaceutical application thereof |
| 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 |
| 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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| Publication number | Priority date | Publication date | Assignee | Title |
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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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| Publication number | Priority date | Publication date | Assignee | Title |
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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 |
Non-Patent Citations (1)
| Title |
|---|
| 中国沙棘中一个新的黄酮醇苷;张静等;《中国医药工业杂志》;20111231;第42卷(第04期);第265-267页 * |
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