CN104147026A - New application of resveratrol derivative - Google Patents
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- CN104147026A CN104147026A CN201410412064.2A CN201410412064A CN104147026A CN 104147026 A CN104147026 A CN 104147026A CN 201410412064 A CN201410412064 A CN 201410412064A CN 104147026 A CN104147026 A CN 104147026A
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Abstract
The invention relates to a new application of a resveratrol derivative, the resveratrol derivative has effects for stabilizing mast cells, reducing obesity rat inflammatory mediator and free fatty acid levels, mitigating hyperinsulinemia and hyperleptindemia, promoting energy metabolism of adipose tissue, realizing fat-reducing effect; a molecule structural formula of the resveratrol derivative is as follows, a molecular formula of the resveratrol derivative with the above molecule structural formula is C20H22O9, the molecular weight is 406, degree of unsaturation n is 10, and a name of the is 3'-hydroxy resveratrol, 4'-O-beta-D-pyranoglucoside. the resveratrol derivative has effects for stabilizing mast cells, reducing obesity rat inflammatory mediator and free fatty acid levels, mitigating hyperinsulinemia and hyperleptindemia, promoting energy metabolism of adipose tissue, realizing fat-reducing effect; the resveratrol derivative has the advantages of obvious curative effect, no toxicity, no side effect, simple and convenient extraction, low cost and high extraction efficiency.
Description
Technical field
The present invention relates to medical technical field, relate in particular to a kind of new purposes of Verakanol derivative.
Background technology
Obesity is a kind of chronic inflammatory diseases, can cause insulin resistant, even and then become the high risk factor of type 2 diabetes mellitus, cardiovascular disease and lipid metabolic disorder, more and more concentrates on immune inflammation field in recent years about fat research.Macrophage is the inflammatory cell of finding the earliest in fatty tissue, fatty tissue macrophage (Adipose tissue macrophage, ATM) the relation that is found to be fat and inflammatory reaction provides a research direction, research finds that macrophage content and obese degree are proportionate, the ratio of normal person ATM in fatty tissue all cells is less than 10%, and can be up to 40% under fat state, ATM is the main source of fatty tissue proinflammatory factor, is to support the fat important evidence as a kind of chronic inflammatory disease process.Obesity is the important pathophysiological basis that causes insulin resistant, and the state of insulin resistant increases the weight of the rising of FFA and triacylglycerol etc., causes blood fat disorder.Meanwhile, being related closely of leptins and insulin resistant found in a lot of research, and hyperinsulinemia depositing normally under fat state, points out and have insulin resistant and leptin resistance simultaneously.Obesity now also becomes the another main killer of harm humans health.Fat of bringing to patient inconvenience in life, overweight people at the sickness rate of the aspects such as cardiovascular and cerebrovascular disease and hypertension, hyperlipidemia, diabetes, heart disease higher than general population.Present diet products have the side effect of diarrhoea mostly.Find and a kind ofly in treatment, need not keep on a diet in fat, do not go on a diet, do not suffer from diarrhoea, do not dewater, the natural green medicine not rebounding, is of great immediate significance.
Summary of the invention
In order to overcome the above problems, the invention provides a kind of Verakanol derivative in the level of stablizing mastocyte realization reduction obese rat inflammatory mediator and free fatty, alleviate hyperinsulinemia and hyperleptinaemia, promote fatty tissue energy metabolism, realize the new purposes of fat-reducing.
The present invention is achieved by the following technical solutions:
The new purposes of above-mentioned Verakanol derivative, has stable mastocyte and realizes the level that reduces obese rat inflammatory mediator and free fatty, alleviates hyperinsulinemia and hyperleptinaemia, promotes fatty tissue energy metabolism, realizes antiobesity action; The molecular structural formula of described Verakanol derivative is as follows:
The molecular formula of described Verakanol derivative is C20H22O9, and molecular weight is 406, degree of unsaturation n=10, and its name is called 3 '-hydroxyl resveratrol, 4 '-O-β-D-glucopyanoside.
The new purposes of described Verakanol derivative, wherein: the Verakanol derivative of described molecular structural formula can also increase the expression of obese rat uncoupling protein-2.
The new purposes of described Verakanol derivative, wherein: the Verakanol derivative of described molecular structural formula promotes fatty tissue energy metabolism, is embodied in the metabolism that can promote free fatty (FFA), triglyceride (TG), low-density lipoprotein cholesterol (LDL-C).
The new purposes of described Verakanol derivative, wherein: the Verakanol derivative of described molecular structural formula alleviates hyperinsulinemia and hyperleptinaemia, be embodied in and can improve blood glucose (FBG), insulin (FINS) and leptin (LEP) level.
The new purposes of described Verakanol derivative, wherein: the Verakanol derivative of described molecular structural formula is realized and reduced obese rat inflammatory mediator, is embodied in the level that can reduce be situated between white element-6 (IL-6) and tumor necrosis factor-alpha inflammatory mediator.
The new purposes of described Verakanol derivative, wherein: the Verakanol derivative of described molecular structural formula can be from natural drug as extracted or synthetic Radix Rhei emodi, Rheum hotaoense C. Y. Cheng et C. T. Kao, Rheum officinale, Rheum tanguticum and Rhizoma Polygoni Cuspidati, Radix Polygoni Multiflori Chinese medicine.
The new purposes of described Verakanol derivative, wherein, the extracting method of the Verakanol derivative of described molecular structural formula is as follows: (1) gets dry Rheum hotaoense C. Y. Cheng et C. T. Kao, pulverize, the medicinal alcohol that is 95% by concentration, first once, rear 6 times of calorimetrics reflux and carry out for the second time, extract for the third time 8 times of calorimetric reflux, extract,, totally three hot refluxs are extracted, merge extractive liquid; (2) extracting solution after above-mentioned steps (1) merging is suitably concentrated, with defat with petroleum ether; (3) extracting solution after above-mentioned steps (2) defat is evaporated to without alcohol taste, with 2 times of amount methanol extractions 8 times, then by extract anhydrous sodium sulfate dehydration, then the extract reclaim under reduced pressure of dewater is extremely done; (4) above-mentioned steps (3) reclaim under reduced pressure is separated with silica gel column chromatography to dry extract, with ethyl acetate: methanol=5:1 eluting, collect component, reclaim under reduced pressure, crude product methanol/water recrystallization, obtains.
Beneficial effect:
The new purposes of Verakanol derivative of the present invention, the Verakanol derivative that is embodied in above-mentioned molecular structural formula has stable mastocyte and realizes the level that reduces obese rat inflammatory mediator and free fatty, alleviate hyperinsulinemia and hyperleptinaemia, promote fatty tissue energy metabolism, the antiobesity action of realization to obese rat, the obvious toxic and side effects of evident in efficacy and nothing.The extracting method of the Verakanol derivative of the above-mentioned molecular structural formula of the present invention is simultaneously simple, convenient, and cost is low and extraction efficiency is high.
The specific embodiment
The new purposes of Verakanol derivative of the present invention, its Verakanol derivative relating to can be from natural drug as extracted the Chinese medicines such as Radix Rhei emodi, Rheum hotaoense C. Y. Cheng et C. T. Kao, Rheum officinale, Rheum tanguticum and Rhizoma Polygoni Cuspidati, Radix Polygoni Multiflori, also can synthetic.
Verakanol derivative of the present invention has stable mastocyte and realizes the level that reduces obese rat inflammatory mediator and free fatty, alleviates hyperinsulinemia and hyperleptinaemia, promotes fatty tissue energy metabolism, realizes the antiobesity action to obese rat.
The structural formula of Verakanol derivative of the present invention is as follows:
The molecular formula of the Verakanol derivative of above-mentioned molecular structural formula is C20H22O9, and molecular weight is 406, degree of unsaturation n=10, and its name is called 3 '-hydroxyl resveratrol, 4 '-O-β-D-glucopyanoside.
The extracting method of the Verakanol derivative of the above-mentioned molecular structural formula of the present invention, comprises the following steps:
1) get dry Rheum hotaoense C. Y. Cheng et C. T. Kao, pulverize, the medicinal alcohol that is 95% by concentration, first once, rear 6 times of calorimetrics reflux and carry out for the second time, extract for the third time 8 times of calorimetric reflux, extract,, and totally three hot refluxs are extracted, merge extractive liquid;
2) by step 1) extracting solution after merging is suitably concentrated, with defat with petroleum ether;
3) by step 2) extracting solution after defat is evaporated to without alcohol taste, and with 2 times of amount methanol extractions 8 times, then by extract anhydrous sodium sulfate dehydration, then the extract reclaim under reduced pressure of dewater is extremely done;
4) by step 3) reclaim under reduced pressure is separated with silica gel column chromatography to dry extract, with ethyl acetate: methanol=5:1 eluting, collect component, reclaim under reduced pressure, crude product methanol/water recrystallization, obtains.
The extracting method of the Verakanol derivative of the above-mentioned molecular structural formula of the present invention is simple, convenient, and cost is low and extraction efficiency is high.
The new purposes to Verakanol derivative of the present invention below in conjunction with specific embodiment or experiment, make further proof:
(1) prepare medicine, reagent and instrument
(1.1) medicine: streptozotocin (STZ), high glucose and high fat feedstuff (20% Adeps Sus domestica, 5% sucrose, 1% cholesterol, 74% normal feedstuff), insulin that purity is greater than 98%;
(1.2) reagent: leptin (LEP) test kit, free fatty (FFA) test kit, reverse transcriptase test kit, polymerase chain reaction (PCR) test kit, 772N visible spectrophotometer, white element-6 (IL-6) that are situated between, tumor necrosis factor-alpha (TNF-α) test kit, triglyceride (TG) are measured test kit, low-density lipoprotein cholesterol (LDL-C) is measured test kit;
(1.3) instrument: blood glucose meter.
(2) model preparation, animal grouping and specimen collection
(2.1) model preparation: select 6～8 weeks, 24 male SD rats of body weight 160～180g, adaptability is fed one week;
(2.2) animal grouping: the SD rat of feeding after a week in above-mentioned steps (2.1) is divided into Normal group, obese model group and Verakanol derivative intervention group, 8 every group at random;
(2.3) specimen collection: obese model group and Verakanol derivative intervention group rat feed high glucose and high fat feedstuff (20% Adeps Sus domestica, 5% sucrose, 1% cholesterol, 74% normal feedstuff), laboratory temperature is room temperature, and humidity is normal wet, freely drink water, round the clock than 1:1; Set time weighs 1 time weekly, and feedstuff divides 3 times/d to supply with; Verakanol derivative intervention group is calculated rat oral gavage dose according to " conventional animal and human body area ratio ", Verakanol derivative consumption every day is 0.09mg/kg, Verakanol derivative is made into 0.04g/l with normal saline, weigh in weekly, then according to the dose calculating, carry out gavage; Normal group, obese model group rat, with same computational methods, by physiologic saline for substitute, continue 12 weeks;
It is generally acknowledged that the rat body weight body weight 120% that is above standard has reached fat standard, after off-test, have 16 rats and reach obese model standard, measure body weight height, calculate lee ' s index; Then more than animal fasting being can't help to water 12h, lumbar injection gives 2% pentobarbital 35ml/kg anesthesia, and docking is got blood examination and surveyed fasting glucose (FBG); Then, cervical vertebra is from disconnected execution rat, hepatic portal passages through which vital energy circulates six district's blood preparations, detect fasting insulin (FINS), leptin (LEP), free fatty (FFA), triglyceride (TG), low-density lipoprotein cholesterol (LDL-C), the white element of Jie-6 (IL-6), tumor necrosis factor-alpha (TNF-α) level.
(3) mensuration of relevant Biochemical Indices In Serum
Adopt blood sugar quantitative to measure GOD-PAP method and detect insulin (FINS), leptin (LEP), free fatty (FFA), triglyceride (TG), low-density lipoprotein cholesterol (LDL-C), the white element of Jie-6 (IL-6), tumor necrosis factor-alpha (TNF-α) level in glucose.
(4) organization material is prepared
After the rat of step (2) is put to death, Jiang Liu district kidney week white adipose organize that to put into rapidly liquid nitrogen freezing, then put in-80 degree ultra cold storage freezers and preserve in order to detecting uncoupling protein-2 (UCP2mRNA);
(5) calculating of lee ' s index
Lee ' s index=* 1000/ body long (cm);
(6) mensuration of uncoupling protein-2 (UCP-2mRNA)
By Trizol description, from about 100mg kidney of rats week and epididymis white adipose tissue, extract total RNA, ultraviolet spectrophotometer carries out quantitatively, electrophoresis judgement RNA quality; By 25 μ L reaction systems, it is that template increases that the synthetic cDNA of reverse transcription puts cDNA aside, and reaction cumulative volume is 25 μ L, 10 * polymerase chain reaction (PCR) buffer, 2.5 μ L wherein, MgCL
2(25mmol/L) 1.5 μ L, dNTPS (10mmol/ μ L) 0.5 μ L, each 0.5 μ L of upstream and downstream primer (10pmol/ μ L), TaqDNA polymerase 1.5U (1U=200ml), cDNA template 2.5 μ L, wherein 10 * polymerase chain reaction (PCR) buffer, 2.5 μ L, mend distilled water to cumulative volume 25 μ L, on the instrument of PE-9600 type polymerase chain reaction (PCR), circulate.Conditioned reflex: 95 ℃ of degeneration 45S, 55 ℃ of annealing+extensions are 2min altogether, and 30 circulations are extended 10min after 55 ℃; RT-PCR product is through 1.2% agarose gel, and gel images scanner carries out gray scale scanning, take β-actin as internal reference, and the gray level ratio that records UCP2mRNA and β-actin mRNA represents the relative value of each experimental group mRNA.
(7) statistical procedures
Result of the test is mean ± standard deviation (± s) expression for data, with SPSS17.0, impacting software analyzes, the significance one factor analysis of variance of group difference, relatively wakes up with a start statistical disposition with SNK check between group, and P ﹤ 0.05 represents that difference has statistical significance.
The situation that affects below in conjunction with the Verakanol derivative of the above-mentioned molecular structural formula of the present invention on each hormone in obese rat body, is described further the present invention:
One, the impact of the Verakanol derivative of the above-mentioned molecular structural formula of the present invention on obese rat weight and Lee ' s index
With Normal group comparison, obese rat weight obviously increases (P ﹤ 0.05), give after the Verakanol derivative intervention of above-mentioned molecular structural formula, weight declines obviously (P ﹤ 0.05), illustrates that the Verakanol derivative of the above-mentioned molecular structural formula of the present invention has significant antiobesity action; With Normal group comparison, obese rat Lee ' s index raises (P ﹤ 0.05), and Verakanol derivative intervention group declines obviously (P ﹤ 0.05), but still higher than Normal group (P ﹤ 0.05, table 1).
The variation (± s, n=8) of table 1 rat weight and Lee ' s index
| Group | Weight (g) | Lee ' s index |
| Normal group | 391±9 | 292.8±1.8 |
| Obese model group | 492±20 b | 315.4±1.7 b |
| Verakanol derivative intervention group | 451±16 be | 306.6±3.2 be |
With Normal group comparison
bp < 0.05; With the comparison of obese model group
ep < 0.05.
Two, the impact of the Verakanol derivative of the above-mentioned molecular structural formula of the present invention on obese rat FBG, FINS and LEP level
With Normal group comparison, obese model group rat FBG level rising (P < 0.05) gives after the Verakanol derivative treatment of the above-mentioned molecular structural formula of the present invention, rat FBG level decline (P < 0.05), illustrate that the Verakanol derivative of the above-mentioned molecular structural formula of the present invention can improve the carbohydrate metabolism state of obese rat, with Normal group comparison, obese model group rat FINS and LEP level all raise (P < 0.05), there is hyperinsulinemia and hyperleptinaemia in prompting, give after the Verakanol derivative intervention of the white above-mentioned molecular structural formula of the present invention, FINS and LEP level all decline (P < 0.05 table 2).
The variation (± s, n=8) of table 2 rat FBG, FINS and LEP level
With Normal group comparison
bp < 0.05; With the comparison of obese model group
ep < 0.05.
Three, the Verakanol derivative of the white above-mentioned molecular structural formula of the present invention is to obese rat FFA, TG
Impact with LDL-C level
With Normal group comparison, obese model group rat FFA, TG and LDL-C level obviously raise (P < 0.05), Verakanol derivative intervention group FFA, TG and LDL-C level decline (P < 0.05), and the Verakanol derivative of the above-mentioned molecular structural formula of prompting the present invention can improve the disorders of lipid metabolism (table 3) of diabetes rat.
Table 3 is respectively organized the variation (± s, n=8) of rat serum FFA, TG and LDL-C level
With normal control comparison
bp < 0.05; With the comparison of obese model group
ep < 0.05.
Four, the impact of the Verakanol derivative of the white above-mentioned molecular structural formula of the present invention on obese rat inflammatory mediator
With normal control comparison, the inflammatory mediator IL-6 of obese rat, `TNF-a level be obviously rising (P < 0.05) all, show that obese rat is in a kind of inflammatory conditions, give IL-6 after the Verakanol derivative intervention of the above-mentioned molecular structural formula of the present invention, `TNF-a level obviously reduces (P < 0.05), but with Normal group more higher (P < 0.05), show that the Verakanol derivative of the above-mentioned molecular structural formula of the present invention can to a certain degree improve the inflammatory conditions (table 4) of obese rat.
The variation (x ± s, n=8) of table 4 rat inflammation medium level
| Group | IL-6(ng/L) | TNF-a(ug/L) |
| Normal group | 21±4 | 0.73±0.13 |
| Obese model group | 56±4 b | 1.86±0.31 b |
| Verakanol derivative intervention group | 40±4 be | 1.40±0.17 be |
With normal control comparison
bp < 0.05; With the comparison of obese model group
ep < 0.05.
Five, the impact of the Verakanol derivative of the above-mentioned molecular structural formula of the present invention on obese rat UCP-2mRNA expression
Under identical condition, extracted total RNA is carried out to PCR reaction, product, after agarose gel electrophoresis, is observed and is found under uviol lamp: each experimental group all has 202bp and two bands of 471bp, matches with the theoretical expanding fragment length of UCP2 and β-actin.With normal control comparison, obese rat UCP-2mRNA expression increases (P < 0.05), after giving the Verakanol derivative intervention of the above-mentioned molecular structural formula of the present invention, UCP-2mRNA expression further increases, with the comparison of obesity group rat, difference has statistical significance (P < 0.05).
In sum, the new purposes of the Verakanol derivative of the above-mentioned molecular structural formula of the present invention, specifically stablize mastocyte and realize the level that reduces obese rat inflammatory mediator and free fatty, improve insulin resistance in obese rats and leptin resistance state, promote fatty tissue energy metabolism, realize the antiobesity action to obese rat.
Claims (7)
1. a new purposes for Verakanol derivative, has stable mastocyte and realizes the level that reduces obese rat inflammatory mediator and free fatty, alleviates hyperinsulinemia and hyperleptinaemia, promotes fatty tissue energy metabolism, realizes antiobesity action; The molecular structural formula of described Verakanol derivative is as follows:
The molecular formula of described Verakanol derivative is C20H22O9, and molecular weight is 406, degree of unsaturation n=10, and its name is called 3 '-hydroxyl resveratrol, 4 '-O-β-D-glucopyanoside.
2. the new purposes of Verakanol derivative as claimed in claim 1, is characterized in that: the Verakanol derivative of described molecular structural formula can also increase the expression of obese rat uncoupling protein-2.
3. the new purposes of Verakanol derivative as claimed in claim 1, it is characterized in that: the Verakanol derivative of described molecular structural formula promotes fatty tissue energy metabolism, is embodied in the metabolism that can promote free fatty (FFA), triglyceride (TG), low-density lipoprotein cholesterol (LDL-C).
4. the new purposes of Verakanol derivative as claimed in claim 1, it is characterized in that: the Verakanol derivative of described molecular structural formula alleviates hyperinsulinemia and hyperleptinaemia, be embodied in and can improve blood glucose (FBG), insulin (FINS) and leptin (LEP) level.
5. the new purposes of Verakanol derivative as claimed in claim 1, it is characterized in that: the Verakanol derivative of described molecular structural formula is realized and reduced obese rat inflammatory mediator, be embodied in the level that can reduce be situated between white element-6 (IL-6) and tumor necrosis factor-alpha inflammatory mediator.
6. the new purposes of Verakanol derivative as claimed in claim 1, is characterized in that: the Verakanol derivative of described molecular structural formula can be from natural drug as extracted or synthetic Radix Rhei emodi, Rheum hotaoense C. Y. Cheng et C. T. Kao, Rheum officinale, Rheum tanguticum and Rhizoma Polygoni Cuspidati, Radix Polygoni Multiflori Chinese medicine.
7. the new purposes of Verakanol derivative as claimed in claim 1, is characterized in that, the extracting method of the Verakanol derivative of described molecular structural formula is as follows:
(1) get dry Rheum hotaoense C. Y. Cheng et C. T. Kao, pulverize, the medicinal alcohol that is 95% by concentration, first once, rear 6 times of calorimetrics reflux and carry out for the second time, extract for the third time 8 times of calorimetric reflux, extract,, and totally three hot refluxs are extracted, merge extractive liquid;
(2) extracting solution after above-mentioned steps (1) merging is suitably concentrated, with defat with petroleum ether;
(3) extracting solution after above-mentioned steps (2) defat is evaporated to without alcohol taste, with 2 times of amount methanol extractions 8 times, then by extract anhydrous sodium sulfate dehydration, then the extract reclaim under reduced pressure of dewater is extremely done;
(4) above-mentioned steps (3) reclaim under reduced pressure is separated with silica gel column chromatography to dry extract, with ethyl acetate: methanol=5:1 eluting, collect component, reclaim under reduced pressure, crude product methanol/water recrystallization, obtains.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105669790A (en) * | 2016-03-08 | 2016-06-15 | 中南林业科技大学 | Bibenzil compounds and extraction method thereof |
| CN111875513A (en) * | 2020-08-20 | 2020-11-03 | 湖南省人民医院 | Resveratrol A ring N (CH)3)2Base derivatives, preparation method and application thereof |
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| CN1294912A (en) * | 1999-11-05 | 2001-05-16 | 中国人民解放军军事医学科学院放射医学研究所 | Blood sugar reducing compound |
| CN101269054A (en) * | 2007-03-20 | 2008-09-24 | 华中科技大学 | Methoxy toluylene compounds as medicaments for preventing and controlling metabolism syndrome and using method thereof |
| CN102058678A (en) * | 2010-12-10 | 2011-05-18 | 成都华西天然药物有限公司 | Medicine or health-care food composition for treating fatty liver |
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2014
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1294912A (en) * | 1999-11-05 | 2001-05-16 | 中国人民解放军军事医学科学院放射医学研究所 | Blood sugar reducing compound |
| CN101269054A (en) * | 2007-03-20 | 2008-09-24 | 华中科技大学 | Methoxy toluylene compounds as medicaments for preventing and controlling metabolism syndrome and using method thereof |
| CN102058678A (en) * | 2010-12-10 | 2011-05-18 | 成都华西天然药物有限公司 | Medicine or health-care food composition for treating fatty liver |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105669790A (en) * | 2016-03-08 | 2016-06-15 | 中南林业科技大学 | Bibenzil compounds and extraction method thereof |
| CN105669790B (en) * | 2016-03-08 | 2016-09-21 | 中南林业科技大学 | A kind of Bibenzyl compound and extracting method thereof |
| CN111875513A (en) * | 2020-08-20 | 2020-11-03 | 湖南省人民医院 | Resveratrol A ring N (CH)3)2Base derivatives, preparation method and application thereof |
| CN111875513B (en) * | 2020-08-20 | 2022-12-30 | 湖南省人民医院 | Resveratrol A ring N (CH) 3 ) 2 Base derivatives, preparation method and application thereof |
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