CN104161748A - Application of rheum lhasaense extract A and B in preparation of biological preparation for reducing blood fat - Google Patents
Application of rheum lhasaense extract A and B in preparation of biological preparation for reducing blood fat Download PDFInfo
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- CN104161748A CN104161748A CN201310182203.2A CN201310182203A CN104161748A CN 104161748 A CN104161748 A CN 104161748A CN 201310182203 A CN201310182203 A CN 201310182203A CN 104161748 A CN104161748 A CN 104161748A
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- lhasa rhubarb
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Abstract
The invention discloses the chemical structural formulas of rheum lhasaense extract A and B, and an application of the rheum lhasaense extract A and B in the preparation of biological preparation for reducing blood fat. The two compounds have a prominent effect on reducing blood fat. Moreover the rheum lhasaense extract B may have a certain effect on treating fatty liver, and has a wide application in preparation of drugs for preventing and treating hyperlipidemia.
Description
Technical field
The invention belongs to biomedicine field, relate to the medical usage of two novel resveratrol trimerizing compound Lhasa rhubarb element A and Lhasa rhubarb element B.
Background technology
Hyperlipemia mainly refers to serum total cholesterol (TC) or triglyceride (TG) level is too high and (or) Serum High-Density Lipoprotein-Cholesterol (HDL-C) level is too low.Hyperlipemia is person in middle and old age's commonly encountered diseases and 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 approximately has 1,200 ten thousand people to die from cardiovascular diseases and apoplexy every year.So the treatment of hyperlipemia is extremely important, this has caused showing great attention to of the whole mankind.The final purpose for the treatment of hyperlipemia is to suppress arteriosclerotic further developing, thereby prevents the death being caused by cardio-cerebrovascular diseases.
Lhasa rhubarb element A (compound 1) and Lhasa rhubarb element B (compound 2) are two novel resveratrol trimers, by inventor's separation and Extraction to carry out structure definite from Rheum ripple leaf group plant plant Lhasa rhubarb (Rheum lhasaense A.J.Li et P.K.Hsiao) first.The report of inanimate object activity.Its structural formula is suc as formula shown in one, two.
The chemical constitution of formula one Lhasa rhubarb element A (compound 1)
The chemical constitution of formula two Lhasa rhubarb element B (compound 2)
Summary of the invention
The chemical structural formula (shown in one, two) of the open noval chemical compound Lhasa rhubarb element A of the present invention and Lhasa rhubarb element B.
The present invention discloses the trimeric a kind of medical usage of these two resveratrols, for the preparation of the purposes of blood fat reducing associated biomolecule preparation.
Lhasa rhubarb element A and Lhasa rhubarb element B all can significantly reduce the serum cholesterol level of hyperlipemia in mice, and Lhasa rhubarb element B can also obviously reduce the liver TG content of animal pattern; Lhasa rhubarb element A is suitable with Lhasa rhubarb element B effect for reducing fat intensity.
The purposes of the Lhasa rhubarb extract that the present invention further provides the present invention in medicine preparation.
According to conventional preparation process, the present invention's compound can be prepared into any pharmaceutical preparation that is applicable to clinical practice.As tablet, capsule, pill, powder, unguentum, dispersant, granule, injectable powder, aqueous injection etc.
Equally, the present invention's compound also can be combined with other active component the preparation that uses formation new.Obviously, these preparations that contain effective site of the present invention are within the scope of claim of the present invention.
Beneficial effect of the present invention: the present invention's noval chemical compound Lhasa rhubarb element A and Lhasa rhubarb element B have significant effect for reducing blood fat; Lhasa rhubarb element B may also have certain lipotropic effect, aspect the medicine as preparation control hyperlipidemia, is having been widely used.
Brief description of the drawings:
Fig. 1 is Electrospray Mass Spectrometry (ESI-MS) spectrogram of Lhasa rhubarb element A of the present invention.
Fig. 2 be Lhasa rhubarb of the present invention element A proton nmr spectra (
1h NMR) spectrogram.
Fig. 3 be Lhasa rhubarb of the present invention element A undistorted polarization transfer technology carbon-13 nmr spectra (
13cNMR) spectrogram.
Fig. 4 is relevant carbon-13 nmr spectra (HMBC) spectrogram of heteronuclear multikey of Lhasa rhubarb element A of the present invention.
Fig. 5 is Electrospray Mass Spectrometry (ESI-MS) spectrogram of Lhasa rhubarb element B of the present invention.
Fig. 6 be Lhasa rhubarb of the present invention element B proton nmr spectra (
1h NMR) spectrogram.
Fig. 7 be Lhasa rhubarb of the present invention element B undistorted polarization transfer technology carbon-13 nmr spectra (
13cNMR) spectrogram.
Fig. 8 is relevant carbon-13 nmr spectra (HMBC) spectrogram of heteronuclear multikey of Lhasa rhubarb element B of the present invention.
Detailed description of the invention
Below in conjunction with the drawings and specific embodiments, technical scheme of the present invention is described in more detail.
Embodiment 1: the structure elucidation of Lhasa rhubarb element A and Lhasa rhubarb element B
Lhasa rhubarb element A is pale yellow powder, and its optical rotation is:
the molecular ion peak m/z679[M-H that the ESI-MS of (C=0.0056, MeOH) (-) provides]
+(HR-ESI-MS:680.9614, calculated for C
42h
32o
9, see accompanying drawing 1) and determine that molecular formula is C
42h
32o
9, degree of unsaturation is 27.Analysis of compounds
1h NMR and
1h-
1h COSY spectrum: fragrant hydrogen signal δ
h7.12 (d, J=8.5Hz, 2H), δ
h6.77 (d, J=8.5Hz, 2H) and δ
h7.16 (d, J=8.5Hz, 2H), δ
h6.75 (d, J=8.5Hz, 2H) show that molecule exists two A
2b
2system, is expressed as A
1ring and C
1ring; δ
h6.10 (d, J=2.0Hz, 2H), δ
h6.14 (t, J=2.0Hz, 1H) and δ
h6.10 (d, J=2.0Hz, 2H), δ
h6.17 (t, J=2.0Hz, 1H) show to contain in molecule two AX
2system, is expressed as A
2and C
2ring; δ
h6.74 (d, J=8.0Hz, 1H), δ
h7.21 (d, J=8.0Hz, 1H) and δ
h6.94 (br s, 1H) show to contain an ABX system in molecule, are expressed as B
2ring; δ
h5.28 (d, J=5.4Hz, 1H), δ
h4.31 (d, J=5.4Hz, 1H) and δ
h5.36 (d, J=8.3Hz, 1H), δ
h4.36 (d, J=8.3Hz, 1H) show to contain in molecule two pairs of fatty hydrogen; δ
h6.40 (d, J=12.2Hz, 1H), δ
h6.46 (d, J=12.2Hz, 1H) show the alkene hydrogen that contains a pair of cis in molecule; From
13in C NMR, can find out δ
c94.72, δ
c94.49, δ
c58.69, δ
c56.69(7a, 8a, 7c, 8c) be 4 fatty carbon, other 38 are all aromatic carbon and olefinic carbon, and its chemical shift is between 100 and 170.Can find out δ from the relevant HMBC signal formula of H-C (accompanying drawing 2)
h6.34(H-2b) and δ
c129.8(C-7b), δ
h6.46(H-8b) and δ
c141.2(C-1b), δ
c130.6(C-14b) there is distant relation, show stilbene be arranged as ring B
1-C7
b-C8
b-ring B
2; The carbon relevant to H-8a has δ
c146.5(C-9a), δ
c107.1(C-10a, 14a), δ
c94.4(C-7a), δ
c134.2(C-1a), δ
c115.1(C-4b), δ
c155.5(C-3b), 163.0(C-5b) show H-8a and encircle A
1, A
2, B
1be connected; The same carbon relevant to H-8c has δ
cδ
c145.4(C-9c), δ
c107.7(C-10c, 14c), δ
c94.7(C-7c), δ
c132.9(C-1c), δ
c131.7(C-11b), δ
c127.4(C-10b), δ
c160.4(C-12b), show H-8c and ring C
1, C
2, B
2be connected; Therefore the basic structure of compound is suc as formula shown in one, called after Lhasa rhubarb element A.
1h NMR and
13c NMR data full ownership is in table one.
The relevant signal formula of main HMBC (direction of arrow is from H to C) of formula three Lhasa rhubarb element A (compound 1) and B (compound 2)
Lhasa rhubarb element B is pale yellow powder, and its optical rotation is:
the molecular ion peak m/z679[M-H that the ESI-MS of (C=0.0054, MeOH) (-) provides]
+(680.9614, calculated forC
42h
32o
9) determine that molecular formula is C
42h
32o
9, degree of unsaturation is 27.Analysis of compounds
1h NMR and
1h-
1hCOSY spectrum: fragrant hydrogen signal δ
h7.13 (d, J=8.5Hz, 2H), δ
h6.76 (d, J=8.5Hz, 2H) and δ
h7.17 (d, J=8.5Hz, 2H), δ
h6.79 (d, J=8.5Hz, 2H) show that molecule exists two A
2b
2system, is expressed as A
1ring and C
1ring; δ
h6.13 (d, J=1.7Hz, 2H), δ
h6.16 (t, J=1.7Hz, 1H) and δ
h6.15 (d, J=1.7Hz, 2H), δ
h6.22 (t, J=1.7Hz, 1H) show to contain in molecule two AX
2system, is expressed as A
2and C
2ring; δ
h6.84 (d, J=8.3Hz, 1H), δ
h7.37 (d, J=8.3Hz, 1H) and δ
h7.20 (br s, 1H) show to contain an ABX system in molecule, are expressed as B
2ring; δ
h5.30 (d, J=5.4Hz, 1H), δ
h4.34 (d, J=5.4Hz, 1H) and δ
h5.39 (d, J=8.4Hz, 1H), 4.44 (d, J=8.4Hz, 1H) show to contain in molecule two pairs of fatty hydrogen; Above data are all similar with compound 1, but the chemical shift contrast of the alkene hydrogen of two compounds is very large, wherein δ in compound 1
h6.40 (d, J=12.2Hz, 1H), δ
h6.46 (d, J=12.2Hz, 1H) are shown to be a cis-structure, and are δ in compound 2
h6.85 (d, J=16.2Hz, 1H), δ
h7.02 (d, J=16.2Hz, 1H) show to contain in molecule a pair of anti-alkene hydrogen; From
13in CNMR, can find out δ
c99.65, δ
c94.94, δ
c58.74, δ
c56.64(7a, 8a, 7c, 8c) be 4 fatty carbon, other 38 are all aromatic carbon and olefinic carbon, and its chemical shift is between 100 and 170.Can find out δ from the relevant HMBC signal formula of H-C (accompanying drawing 3)
h6.50(H-2b) and δ
c127.4(C-7b), δ
h6.50(H-8b) and δ
c141.5(C-1b), δ
c128.7(C-14b) there is distant relation, show stilbene be arranged as ring B
1-C7
b-C8
b-ring B
2; The carbon relevant to H-8a has δ
c146.6(C-9a), δ
c107.0(C-10a, 14a), δ
c94.5(C-7a), δ
c134.3(C-1a), δ
c115.4(C-4b), δ
c155.6(C-3b), δ
c163.3(C-5b) show H-8a and ring A
1, A
2, B
1be connected; The same carbon relevant to H-8c has δ
c145.3(C-9c), δ
c107.9(C-10c, 14c), δ
c94.9(C-7c), δ
c132.8(C-1c), δ
c132.4(C-11b), δ
c124.1(C-10b), δ
c160.9(C-12b), show H-8c and ring C
1, C
2, B
2be connected; The basic structure of this compound is suc as formula shown in two, called after Lhasa rhubarb element B.
1h NMR and
13c NMR data full ownership is in table one.
Table 1 Lhasa rhubarb element A and Lhasa rhubarb element B's
1h NMR,
13c NMR data
The 1H NMR of continued 1 compound 1 and compound 2,13C NMR data
Embodiment 2: the effect for reducing fat research of the effect for reducing fat research series samples of Lhasa
1 material
1.1 medicine
S
1sample, yellow powder, is the research code name of Lhasa rhubarb element A; S
2sample, yellow powder, is the research code name of Lhasa rhubarb element B.Fenofibrate, 100mg/ sheet, Yan'an Wanxiang Pharmaceutical Co., Ltd., Shanghai produces, lot number 121101.When experiment, with 0.5%CMC-Na respectively by S
1～S2 sample and positive control fenofibrate are made into the suspension of desired concn.
1.2 reagent
Triglyceride (TG, 1204101), cholesterol (TC, 1204101) test kit, Sichuan Mai Ke Science and Technology Ltd. produces; Cholesterol (13030) and natrii tauroglycocholas (20131201) biochemical reagents, Beijing extensive and profound in meaning star biochemical technology Co., Ltd produces.
1.3 animal
SPF level ICR mice; Clean level Mus mixed feed; Provided by unming Medical College's Experimental Animal Center.
1.4 instrument
TMS1024 automatic clinical chemistry analyzer, Tokyo Co., Ltd.; Centrifuge5810R type refrigerated centrifuger, German eppendoff company; BS110 type electronic analytical balance, Sai Duolisi company; Millipor ultra-pure-water treatment system, Millipor company of the U.S..
1.5 statistics
Data with
represent, carry out t with Excel and check the relatively significance of group difference.
2 methods and result
Select 143 of 18～20g male mices, be divided at random 14 groups: blank group; 1 group, model (0.5%CMC-Na); 2 groups, model (2% tween 80); Fenofibrate 100mg/kg group; S
1～S
30.5,2.0g/kg group; SO～SZO0.2,1.0g/kg group; Blank and model control group is 11, and all the other each group is 10.Except Normal group is fed normal diet, all the other each treated animals are all fed high lipid food, freely ingest and drink water.During moulding each treated animal morning every day on an empty stomach according to dosage timing gastric infusion once, volume is 20ml/kg, 1 group, blank group and model gavage 0.5%CMC-Na, 2 groups, model gavages 2% tween 80, continuous 7 days.After last administration, water 12h is can't help in fasting, gets blood by eye socket, and separation of serum, by the content of kit method mensuration TC and TG.After getting blood, animal is put to death in dislocation, wins liver and weighs, and calculates liver coefficient, and takes sample 200 ± 2mg in liver with position, uses ethanol: acetone (1:1) mixes extract 2ml homogenate, measures the TG content in hepatic tissue.The results are shown in Table 2 and table 3.
High lipid food formula: 1% cholesterol, 10% Adeps Sus domestica, 0.3% sodium cholate, 88.7% normal feedstuff.
The impact (X ± SD) of table 2 series samples on hyperlipemia in mice blood lipid level
Compared with blank group: △ P<0.01; : ﹡ P<0.05 compared with model group
Experimental result shows, positive control fenofibrate, S
1and S
2two dosage groups all can obviously reduce the serum cholesterol level of hyperlipemia in mice, S
3there is obvious reduction serum TC trend.
The impact of table 3 series samples on hyperlipemia in mice liver exponential sum liver TG
Compared with blank group: △ P<0.01; Compared with model group: * P<0.05, * * P<0.01
Experimental result shows, the TG regulating liver-QI coefficient of model group animal livers obviously raises; S
2two dosage groups can obviously reduce the liver TG content of hyperlipemia in mice, and liver coefficient is had no significant effect;
3. brief summary
S
1and S
2all can significantly reduce the serum cholesterol level of hyperlipemia in mice, S
2can also obviously reduce the liver TG content of animal pattern; S
1and S
2effect for reducing fat intensity is suitable, but S
2there is the advantage of obvious reduction liver TG content; Result: S1, S2 can significantly reduce the blood lipid level of hyperlipemia in mice; S2 can also significantly reduce the liver TG of hyperlipemia in mice.Conclusion: S1, S2 have significant effect for reducing blood fat; S2 may also have certain lipotropic effect.
Embodiment 3: Lhasa rhubarb element tablet preparation
Method for making: take Lhasa rhubarb element A or B100g, be dissolved in appropriate ethanol, add 900g PVPK29/32, mix homogeneously, makes abundant dissolving; Rotary evaporation makes ethanol volatilization, cooling, dry, solidify, pulverize solidfied material, get 100 grams and mix with 50 grams of lactose, 30 grams of pregelatinized Starch, 10 grams of carboxymethyl starch sodium, cross 80 mesh sieve 2 times, mix homogeneously, taking 1% low-substituted hydroxypropyl cellulose alcoholic solution (concentration 50%) as binding agent soft material processed, crossing 40 mesh sieves granulates, 60 DEG C dry, crosses 30 mesh sieve granulate, adds 1.5 grams of Pulvis Talci mix homogeneously, tabletting, can prepare 1000, Lhasa rhubarb element A or Lhasa rhubarb element B tablet.
Claims (3)
1. Lhasa rhubarb A(structural formula 1) and B(structural formula 2) for the preparation of the application in fat biological preparation.
Structural formula 1
Structural formula 2
Described in claim 1 compound for the preparation of the purposes of blood lipid-lowering medicine.
Described in claim 1 compound for the preparation of the purposes of blood fat reducing health products.
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|---|---|---|---|
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110624006A (en) * | 2019-09-23 | 2019-12-31 | 昆明翔昊科技有限公司 | A health wine containing effective components of fructus Quzhazhii |
| CN112830947A (en) * | 2020-12-21 | 2021-05-25 | 中国医学科学院药用植物研究所 | Stilbene compounds isolated from Lhasa rhubarb and their use in the treatment of nervous system diseases |
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| JP2005008572A (en) * | 2003-06-19 | 2005-01-13 | Yakult Honsha Co Ltd | Lipase inhibitor |
| CN101244129A (en) * | 2007-12-14 | 2008-08-20 | 昆明翔昊科技有限公司 | Lhasa rhubarb extract, preparation method, and application in preparing preparation for treating cardiovascular and cerebrovascular diseases |
| CN101787061A (en) * | 2010-03-02 | 2010-07-28 | 昆明翔昊科技有限公司 | Application of Quzhazhigan in preparation of preparations for preventing and treating cardiac-cerebral ischemia diseases, and preparation method thereof |
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2013
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005008572A (en) * | 2003-06-19 | 2005-01-13 | Yakult Honsha Co Ltd | Lipase inhibitor |
| CN101244129A (en) * | 2007-12-14 | 2008-08-20 | 昆明翔昊科技有限公司 | Lhasa rhubarb extract, preparation method, and application in preparing preparation for treating cardiovascular and cerebrovascular diseases |
| CN101787061A (en) * | 2010-03-02 | 2010-07-28 | 昆明翔昊科技有限公司 | Application of Quzhazhigan in preparation of preparations for preventing and treating cardiac-cerebral ischemia diseases, and preparation method thereof |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110624006A (en) * | 2019-09-23 | 2019-12-31 | 昆明翔昊科技有限公司 | A health wine containing effective components of fructus Quzhazhii |
| CN112830947A (en) * | 2020-12-21 | 2021-05-25 | 中国医学科学院药用植物研究所 | Stilbene compounds isolated from Lhasa rhubarb and their use in the treatment of nervous system diseases |
| CN112830947B (en) * | 2020-12-21 | 2022-10-04 | 中国医学科学院药用植物研究所 | Stilbene compounds isolated from Rheum lhasaense and their use in treating nervous system diseases |
| CN115650940A (en) * | 2020-12-21 | 2023-01-31 | 中国医学科学院药用植物研究所 | Compounds isolated from Lhasa rhubarb and their use in the treatment of neurological disorders |
| CN115650940B (en) * | 2020-12-21 | 2024-03-29 | 中国医学科学院药用植物研究所 | Compounds isolated from Rheum emodi and their use in the treatment of neurological disorders |
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Application publication date: 20141126 |