CN103110651A - Application of active ingredient namely loganin in dogwood in preparation of medicaments for treating diabetes - Google Patents
Application of active ingredient namely loganin in dogwood in preparation of medicaments for treating diabetes Download PDFInfo
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- CN103110651A CN103110651A CN2013100480860A CN201310048086A CN103110651A CN 103110651 A CN103110651 A CN 103110651A CN 2013100480860 A CN2013100480860 A CN 2013100480860A CN 201310048086 A CN201310048086 A CN 201310048086A CN 103110651 A CN103110651 A CN 103110651A
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Abstract
The invention discloses a new medical application of loganin, and in particular relates to an application of the loganin in preparation of medicaments for treating diabetes, wherein the loganin is extracted from dogwood. The method for extracting the loganin comprises the following steps of: (1) performing water extraction and alcohol precipitation on dogwood coarse powder to obtain a dogwood water extraction and alcohol precipitation extracting solution; (2) loading the dogwood water extraction and alcohol precipitation extracting solution into a macroporous adsorption resin column, and performing enrichment to obtain dogwood iridoid glycosides; (3) performing chromatographic separation by using a silica gel column to obtain a loganin flow component; and (4) purifying to obtain a loganin monomeric compound. Pharmacodynamics experimental results prove that the loganin has the functions of reducing the content of blood sugar, serum AGEs and urokinase protein, raising the serum insulin level, relieving pathologic lesions of pancreas, kidney, liver, heart, testis and the like, and obviously improving a 'three more one less' symptom. Therefore, the loganin can be used for preparing the medicaments for treating the diabetes.
Description
Technical field
The present invention relates to the novel medical use of loganin, specifically relate to the application of effective ingredient loganin in preparation treatment diabetes medicament in Fructus Corni.
Background technology
Diabetes belong to " diabete " category on Chinese medicine.Long-term diabetes can cause the chronic complicating diseases of diabetes, are mainly wherein vascular lesions.The macroangiopathic change nature is atherosclerosis, mainly involves the trunks such as aorta, coronary artery, and the microangiopathies main manifestations of diabetes is the microangiopathies such as retina, kidney.Clinical statistics shows, the diabetics of 40%-50% after 10 years, retinopathy occurs in morbidity; Approximately there is 2% patient as blind as a bat after 15 years in morbidity; 5%~10% patient is worsened into end stagerenaldisease in morbidity after 20 years.Although the definite pathomechanism of the genesis of chronic complicating diseases of diabetes is still very not detailed at present, mainly contains the multiple hypothesis such as nonenzymatic glycosylation theory, polyhydric alcohol path theory, protein kinase C activation theory, oxidative stress.The nonenzymatic glycosylation theory thinks, under long-term hyperglycemia state, glucose molecule can with body internal protein generation non-enzymatic glycation, form the result of irreversible strong active substance-advanced glycosylation end products (AGEs).The toxicity of AGEs is very large, after crosslinked, its supporting structure aperture is increased as glomerular basement membrane AGEs, and permeability raises, and albumen, immunoglobulin etc. in " seizures " blood circulation increase the discharge of basement membrane thickened and urine protein.AGEs also has chemotaxis, impel monocytes/macrophages to move to extracellular matrix (ECM), and cause and monocytes/macrophages, endotheliocyte and mesangial cell secrete cytokines as TNF-α, IL-1 α, IGF-1A, PDGF etc., cause the glomerule proliferative lesion.In addition, AGEs is combined rear activation signal Signal Transduction Pathways with cell surface RAGE, generate multiple damage factor such as TNF-α, IL-6, TGF-β, thereby further cause and increase the weight of generation and the development of chronic complicating diseases of diabetes.Present clinical chemicals such as sulfonylurea, the biguanides etc. that are used for the treatment of diabetes, although certain hypoglycemic activity is arranged, but because side effect is larger, and on the AGEs that generated without impact, therefore can not slow down the generation of chronic complicating diseases of diabetes, have certain limitation on the treatment diabetes.Therefore seek existing hypoglycemic activity, the medicine tool that can slow down again its chronic complicating diseases has very important significance.
Summary of the invention
Goal of the invention: the object of the present invention is to provide the novel medical use of loganin, specifically be to provide the application of effective ingredient loganin in preparation treatment diabetes medicament in Fructus Corni.
Technical scheme:
A kind of monomeric compound for the treatment of diabetes---loganin, this compound are that extraction separates and obtains from Fructus Corni, have comprised the concrete extraction step such as water decoction-alcohol sedimentation, separation, purification in step as follows:
1. the preparation of water extract-alcohol precipitation extracting solution: take the Fructus Corni coarse powder, add 2~12 times of water soakings to spend the night, decoct 2~4 times, merge water extraction liquid, be evaporated to 1/2~1/10 of original volume, add 2~10 times of amount dehydrated alcohol, stir evenly, cold preservation is spent the night, filter, filtrate recycling ethanol is evaporated to without the alcohol flavor, gets Fructus Corni water extract-alcohol precipitation extracting solution;
2. the preparation of cornel iridoid glycoside class: get above-mentioned gained Fructus Corni extracting solution, be written into the D101 macroporous adsorptive resins, first use 1000~4000mL distilled water eluting, use again 20~60% ethanol water 1000~5000mL eluting, collect effluent, eluting part concentrating under reduced pressure is got rufous extractum, extractum is transferred in culture dish, be positioned over the cryotherapy refrigerator interior freezing, dry rear grind into powder gets the cornel iridoid glycoside class;
3. the preparation of loganin monomeric compound: adopt silica gel (100~200 order) wet method dress post, get above-mentioned obtained freeze-drying powder, with appropriate dissolve with methanol, add the equivalent silica gel mixed sample, reclaim under reduced pressure methanol gets the rufous powder to doing; Upper silica gel column chromatography separates, and (3~8:1) solvent systems carry out isocratic elution, collect effluent with chloroform-methanol, be decompressed to driedly again, use appropriate dissolve with methanol, silica gel thin-layer chromatography is followed the tracks of and is detected, merge all stream parts of goal object, and suitably fling to a part of methanol;
4, will carry out purification through preparative high performance liquid chromatography with upper reaches part, every pin sample introduction 1~5mL sample solution, disengaging time 10~40min, eluent be with the mixed solution of deionized water and methanol, take 10~30% methanol aqueous solutions as a little less than wash, 70~90% methanol aqueous solutions are for washing by force, collect according to the time of chromatographic peak in chromatograph, then merge the effluent that contains loganin, concentrated gained solution is to containing less moisture content, lyophilization, obtain the loganin monomeric compound, purity is 98.5%.
The application of effective ingredient loganin in preparation treatment diabetes medicament in Fructus Corni.
Fructus Corni of the present invention is the drying and ripening sarcocarp of Cornaceae plant Fructus Corni CornusoficinalisSieb.etZucc..Modern chemistry studies show that the Fructus Corni active ingredient mainly contains iridoid glycoside, triterpenic acid and polysaccharide.The main component of iridoid glycosides is morroniside, loganin, sweroside etc., and wherein iridoid glycoside has the effects such as blood sugar lowering, antiplatelet aggregation and antithrombotic; Polysaccharide has antioxidation, the anti-ageing effect of waiting for a long time; Triterpenic acid has antiinflammatory, blood fat reducing, blood sugar lowering and antitumaous effect.Fructus Corni ethyl acetate extraction position, n-butanol extraction position, ethanol extract have the level that reduces blood glucose and rising insulin.Fructus Corni, the sour-puckery flavor tepor is returned liver, kidney channel, liver and kidney tonifying, essence astringing and desertion stemming.The also discovery of Integral animal experiment research in early stage, the Fructus Corni iridoids can improve blood glucose in diabetic rats level, Profilin urine, reduce the glucose in urine metabolism, recovers NO-ET and TXA
2-PGI
2Balance suppresses the generation of AGEs, alleviates nephropathy change, cardiomyopathy, retinopathy and Thoracic Aortic Diseases, shows that iridoids has the blood sugar level of improving diabetes and the effect of chronic complicating diseases.
The purity testing of loganin
Adopt the HPLC method to measure.Condition is chromatographic column: ThermoODSHypersil(4.6mm * 150mm, 5 μ m); Mobile phase: water-acetonitrile (88:12); Flow velocity 1mLmin-1; Sample size: 20 μ L; 35 ℃ of column temperatures; Detect wavelength 240nm.Fig. 1.
Loganin provided by the invention causes studies show that of diabetic mice model through AGEs feedstuff composite S TZ, and this compound can improve diabetic mice " three-many-one-little " symptom, and blood sugar reducing function is obvious, and protection islets of langerhans, kidney, heart, testis are respond well.Therefore loganin provided by the invention can be used as the medicine of preparation treatment diabetes.
Description of drawings
Loganin HPLC chromatogram in Fig. 1, sample.
Loganin HPLC hydrogen spectrogram in Fig. 2, sample.
Loganin HPLC carbon spectrogram in Fig. 3, sample.
The specific embodiment
Below in conjunction with specific embodiment, further illustrate the present invention, should understand these embodiment and only be used for explanation the present invention, limit the scope of the invention and be not used in, after having read the present invention, those skilled in the art all fall within the application's claims limited range to the modification of the various equivalent form of values of the present invention.
The extracting method of effective ingredient loganin monomeric compound in embodiment 1 Fructus Corni, its extracting method step is as follows:
(1) extraction of Fructus Corni water extract-alcohol precipitation extracting solution:
Take approximately 5kg of Fructus Corni coarse powder (crossing 10 mesh sieves), add 6 times of water soakings to spend the night, then decoct 2 times, each 1h filters, and merges water extraction liquid, be evaporated to 1/5 of original volume, add 4 times of amount dehydrated alcohol, stir evenly, cold preservation is spent the night, filter, filtrate recycling ethanol is evaporated to without the alcohol flavor, gets Fructus Corni water extract-alcohol precipitation extracting solution;
(2) iridoid glycosides in macroporous resin enrichment Fructus Corni extracting solution:
Get gained Fructus Corni extracting solution in step 1, be written into the D101 macroporous adsorptive resins, first use 2000mL distilled water eluting, with remove portion impurity, then use approximately 2500mL eluting of 30% ethanol water, collect effluent, with 30% ethanol water eluting part concentrating under reduced pressure, get rufous extractum, extractum is transferred in culture dish, be positioned over-the interior freezing approximately 3h of 86oC cryotherapy refrigerator, take out lyophilization, get the rufous solid matter, careful grind into powder is put into exsiccator and stored, and is stand-by;
(3) silica gel column chromatography separates to get loganin stream part:
Silica gel (100~200 order) wet method dress post is got obtained freeze-drying powder in step (2), with appropriate dissolve with methanol, adds the equivalent silica gel mixed sample, and reclaim under reduced pressure methanol gets the rufous powder to doing; Upper silica gel column chromatography separates, carry out isocratic elution with chloroform-methanol (6:1) solvent system, per hour collect the effluent of a approximately 500mL, be decompressed to again dried, use appropriate dissolve with methanol, silica gel thin-layer chromatography is followed the tracks of and is detected, according to the thin layer chromatography check result, whether contain the goal object loganin in preliminary judgement stream part, confirm with high-efficient liquid phase chromatogram technique analysis, judgement contains stream part of loganin according to chromatogram again, merges all stream parts of the goal object that contains similar purity, and fling to a part of methanol, to reach concentrated purpose;
(4) preparative HPLC purification loganin monomeric compound
Stream part of gained in step (3) is carried out purification through preparative high performance liquid chromatography, every pin sample introduction 1~5mL sample solution, disengaging time 20min, about sample introduction three pins per hour, the eluent mixed solution of deionized water and methanol, take 10% methanol aqueous solution as a little less than wash, 90% methanol aqueous solution is for washing by force, collect according to the time of chromatographic peak in chromatograph, then merge the effluent that contains loganin, concentrated gained solution is to containing less moisture content, lyophilization obtains the loganin monomeric compound, and purity is 98.5%.
The purity testing step of embodiment 2 loganin monomeric compounds
Adopt the HPLC method to measure.Condition is chromatographic column: ThermoODSHypersil(4.6mm * 150mm, 5 μ m); Mobile phase: water-acetonitrile (88:12); Flow velocity 1mLmin-1; Sample size: 20 μ L; 35 ℃ of column temperatures; Detect wavelength 240nm.Record loganin (molecular formula: C
17H
26O
10, molecular weight: 390.38) purity is 98.5%.The loganin chemical structural formula is as follows: Fig. 1 is loganin HPLC chromatogram in sample;
Fig. 2 is the hydrogen spectrogram of loganin in sample
Prepare the loganin monomeric compound by the extracting method of embodiment 1 and carry out pharmacological experiment study, method is as follows:
Get male 6 the week age C57BL/6J mice, body weight 18-22g, adaptability fed for 1 week, fasting 12h before modeling, respectively at the 1st day, the 4th day dosage lumbar injection streptozotocin (STZ) with 100mg/kg, measured the mice fasting glucose on the 8th day, choose blood glucose value greater than the mice of 16.7mmol/L as diabetes modeling success mice.Be divided at random model group, metformin group (0.2g/kg), loganin low dosage (0.02g/kg), loganin high dose group (0.1g/kg) by blood glucose value, 10 every group, above mice is all with high AGEs forage feed.Separately establish simultaneously one group of blank group.The medicine of the above-mentioned dosage of the other gavage of drug component, every day 1 time, continuous 12 weeks, model group and blank group mouse stomach distilled water.
At experimental session and after finishing, carry out the mensuration of following index:
1. general index determining: every 4 weeks are measured Mouse Weights, blood glucose, dietary amount, amount of drinking water and urine amounts.
2. biochemical indicator: mice is got blood after winning eyeball, for detection of AGEs, serum insulin etc. in serum; Every 4 weeks are collected urine, and the centrifugal 10min of 3000rpm gets supernatant and surveys urine protein content.
3. organ coefficient and tectology inspection: experiment is got pancreas, liver, heart, kidney, testis after finishing, and kidney is weighed rapidly, calculates organ index: heavy (the mg)/body weight (g) of organ coefficient (mg/g)=kidney.Institute's taking internal organ is fixed with 10% formalin, be used for histopathologic examination.
Experimental result is as follows:
1. mice ordinary circumstance and body weight, change of blood sugar
Before administration and after administration, 4W, 8W, 12W measure Mouse Weight respectively, tail point measuring blood sugar of blood extracting.Begin to occur the metabolism disorder symptoms such as polyphagia, polydipsia, polyuria after mice Cheng Mo, and increase the weight of gradually; After 12 weeks of medication, model group mice fur is withered and yellow, be slow in action, and bradykinesia, body weight obviously descends (P<0.01) than the blank group, and blood glucose value, food ration, amount of drinking water, urine amount are all than blank group obviously raise (P<0.01).After giving loganin, though Mouse Weight is compared not statistically significant with model group, the indexs such as its blood glucose, food ration, amount of drinking water, urine amount all have obvious decline (P<0.05,0.01) than model group, see Table 1-5.
2. mouse blood and urine biochemical indicator
The result demonstration, loganin can reduce the excretion of urine protein, reduces serum AGEs and rising serum insulin content, sees Table 6-7 with model group comparing difference remarkable (P<0.05,0.01).
3. organ coefficient and histopathologic examination
The result demonstration, loganin can reduce the kidney organ index, and the metformin reducing effect is not obvious; Histopathologic examination's result shows, loganin slightly makes islet function take a turn for the better, but with model group there was no significant difference relatively; Kidney, heart, testis pathological changes can be reduced, with model group comparing difference remarkable (P<0.05,0.01), slightly hepatic lesions can be alleviated.See Table 8-10.
Compare with the blank group ##p<0.01; * compare with model group p<0.05
Compare with the blank group ##p<0.01; * p<0.05, * * p<0.01 and model group comparison
Compare with the blank group ##p<0.01; * p<0.05, * * p<0.01 and model group comparison
Compare with the blank group ##p<0.01; * p<0.05, * * p<0.01 and model group comparison
Compare with the blank group ##p<0.01; * p<0.05, * * p<0.01 and model group comparison
Table 6 loganin on the impact of AGEs+STZ diabetic mice 24h excretion quantity of urinary protein (
N=5)
Compare with the blank group ##p<0.01; * p<0.05, * * p<0.01 and model group comparison
The impact of table 7 loganin on AGEs+STZ diabetic mice serum insulin and AGEs level
Compare with the blank group ##p<0.01; * p<0.05, * * p<0.01 and model group comparison
Table 8 loganin on the impact of AGEs+STZ diabetic mice organ coefficient (
N=10)
Compare with the blank group ##p<0.01; Compare with model group * p<0.01
Table 10 loganin on the impact of AGEs+STZ diabetic mice kidney, the heart, liver, testis pathological changes (
N=6)
Annotate: score value is higher, and pathological changes is heavier.
The present invention has carried out chemical extraction, separation and purification to active component loganin in Fructus Corni, and it has been carried out the pharmacological basic research such as blood sugar lowering by integrated application modern chemistry, pharmacy, pharmacological method and technology.Above result shows, loganin can reduce blood glucose and serum AGEs level, the rising serum insulin, reduce the excretion of dietary amount, amount of drinking water and urine amount and urine protein, improve islet function, alleviate the pathological changes such as kidney, heart, liver, testis, so the present invention can be clinical practice loganin treatment diabetes experimental basis is provided.
Above embodiment only is explanation technical conceive of the present invention and characteristics; its purpose is to allow the person skilled in the art understand content of the present invention and implemented; can not limit protection scope of the present invention with this; all equivalences that spirit is done according to the present invention change or modify, and all should be encompassed in protection scope of the present invention.
Claims (1)
1. the application of effective ingredient loganin in preparation treatment diabetes medicament in Fructus Corni.
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CN115304653A (en) * | 2022-08-16 | 2022-11-08 | 河南中医药大学 | Four iridoid glycoside compounds extracted from dogwood, preparation method and application thereof |
CN115304653B (en) * | 2022-08-16 | 2024-05-28 | 河南中医药大学 | Four iridoid glycoside compounds extracted from dogwood, and preparation method and application thereof |
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