CN105769834A - Application of Antrodia camphorate compound and extract to preparation of drug used for promoting insulin secretion - Google Patents
Application of Antrodia camphorate compound and extract to preparation of drug used for promoting insulin secretion Download PDFInfo
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Abstract
The purposes for promoting the drug of insulin secretion is used to prepare the invention discloses a kind of Antrodia camphorata compound, extract. The compound is indicated with Formulas I:
, wherein R1 is hydrogen or acetyl group, and R2 is
Or
.
Description
Technical field
The present invention is about the compound of a kind of separated from Antrodia sesame, extract and application thereof, especially with regard to this compound and extract are applied to the purposes that preparation promotes the medicine of insulin secretion.
Background technology
Antrodia Camphorata (Antrodiacamphorata), also known as Antrodia camphorata, Antrodia camphorata or red Antrodia camphorata etc., belong to the perennial mushroom fungus class of Aphyllophorales (Aphyllophorales), Polyporaceae (Polyporaceae), for Taiwan endemic species fungus, it is only grow on the rotten heartwood inwall of hollow of Taiwan child care class seeds-Cinnamomum kanahirai hay tree (CinnamoumkanehiraiHay).Owing to Cinnamomum kanahirai hay tree distributed quantity is extremely rare, add artificial felling trees unlawfully so that parasitize the wild Antrodia Camphorata quantity more shape that wherein can grow rare, and owing to its sporophore growth is relatively slow, trophophase is also only between June to October, and therefore price is much more expensive.
With studied maximum of triterpenoid compound in the numerous composition of Antrodia Camphorata, triterpenoid compound is to be combined into hexagon or the general name of pentagon native compound by 30 carbons, and the bitterness that Antrodia Camphorata has is namely essentially from this composition of triterpenes.During nineteen ninety-five, Cherng et al. finds in Antrodia Camphorata sporophore extract containing the triterpenoid compound being skeleton with lumistane (ergostane) three kinds new: antcinA, antcinB and antcinC (Cherng, I.H., andChiang, H.C.1995.ThreenewtriterpenoidsfromAntrodiacinnamomea.J.N at.Prod.58:365-371).Chen et al. is to find three kinds of triterpenoid compound (Chen such as zhankuicacidA, zhankuicacidB and zhankuicacidC after alcohol extraction Antrodia camphorata sporophore, C.H., andYang, S.W.1995.NewsteroidacidsfromAntrodiacinnamomea ,-afungusparasiticonCinnamomummicranthum.J.Nat.Prod.58:165 5-1661).nullIn addition，Chiang et al. in nineteen ninety-five also by sporophore extract in find the new triterpenoid compound of other three kinds of respectively sesquiterpene lactones (sesquiterpenelactone) and two kinds of bisphenols derivants，This is antrocin,4,7-dimethoxy-5-methyl isophthalic acid,3-benzo dioxy ring (4,7-dimethoxy-5-methy-1,3-benzodioxole) with 2,2',5,5'-tetramethoxy-3,4,3',4'-pair-methylene-dioxy-6,6'-dimethyl diphenyl (2,2',5,5'-teramethoxy-3,4,3',4'-bi-methylenedioxy-6,6'-dimethylbiphenyl)(Chiang,H.C.,Wu,D.P.,Cherng,I.W.,andUeng,C.H.1995.Asesquiterpenelactone,phenylandbiphenylcompoundsfromAntrodiacinnamomea.Phytochemistry.39:613-616).By 1996, Cherng et al. finds triterpenoid compound four kinds new once again to analyze method equally: antcinE, antcinF, methylantcinateG, methylantcinateH (Cherng, I.H., Wu, D.P., andChiang, H.C.1996.TriteroenoidsfromAntrodiacinnamomea.Phytochemis try.41:263-267)；nullYang et al. is then found that two kinds of noval chemical compound zhankuicacidD being skeleton with lumistane、zhankuicacidE，With three kinds be skeleton with lanostane (lanostane) noval chemical compound: 15 α acetyl-dehydrosulphurenic acid (15 α-acetyl-dehydrosulphurenicacid)、Dehydroeburicoic acid (dehydroeburicoicacid) and the sulfurenic acid that anhydrates (dehydrasulphurenicacid) (Yang,S.W.,Shen,Y.C.,andChen,C.H.1996.SteroidsandtriterpenoidsofAntrodiacinnamomea-af ungusparasiticonCinnamomummicranthum.Phytochemistry.41:1 389-1392).
Diabetes spp in endocrine metabolism chronic disease, be insulin secretion definitely or relative deficiency and cause the disease of sugar, fat and protein metabolism disorder, be divided into I type and two kinds of II type clinically.I type is insulin-dependent (IDDM), and the overwhelming majority falls ill because of autoimmune, patient because beta Cell of islet is impaired cannot excreting insulin, cause that insulin is definitely not enough；II type is non-insulin-depending type (NIDDM), patient's beta Cell of islet still has the function of excreting insulin, simply because islets of langerhans is have opposing or insensitive by target cell (corresponding cell) Insulin receptor INSR, insulin does not have the time marquis at needs to discharge or the adhesion of receptor and insulin declines, although the amount of insulin is normal, but can not meeting the needs maintaining homergy and make blood glucose raise, glucose in urine increases, and this situation is called insulin relative deficiency.
Although can be learnt that Antrodia Camphorata extract has multiple medical functions by current many experiments, but do not work out it for wherein specific extract/compound and there is the effect promoting insulin secretion, so the association area being applied in research Antrodia Camphorata of aspect still needs to be differentiated further.
Summary of the invention
Accordingly, the present inventor has suitable studying intensively based on the extract/compound for Antrodia Camphorata, finds out some specific Antrodia Camphorata extract/compounds gradually and has the both effectiveness of insulin secretion.
One purpose of the present invention, in the purposes of the medicine providing a kind of Antrodia Camphorata compound to promote insulin secretion as preparation, represents with Formulas I:
Wherein R1 is hydrogen or acetyl group, and R2 is
It is preferred that wherein the R1 of this compound to be hydrogen, R2 beRepresent with formula (II):
It is preferred that wherein the R1 of this compound to be acetyl group, R2 beRepresent with formula (III):
It is preferred that wherein the R1 of this compound to be hydrogen, R2 beRepresent with formula (IV):
It is preferred that wherein the R1 of this compound to be hydrogen, R2 beRepresent with formula (V):
The present invention more provides a kind of Antrodia Camphorata extract for preparing the purposes of the medicine promoting insulin secretion.
Preferably, wherein this extract obtains so that the following step carries out extracting: takes and merges concentration after Antrodia Camphorata mycelium, sporophore or the mixture of the two extract 2 times with the ethanol of 10 times amount and obtain one and slightly take out thing, this is slightly taken out thing and is allocated extraction 3 times with methylene chloride/water (1:1), to be divided into a dichloromethane layer and a water layer, wherein this dichloromethane layer and this water layer are this Antrodia Camphorata extract.
Accompanying drawing explanation
Figure 1A～Figure 1B represents Antrodia Camphorata extract ANCA-D, ANCA-W cell survival rate analysis for MIN6 cell.
Fig. 2 A～Fig. 2 C represents Antrodia Camphorata compound AntrocamolLT1, AntrocamolLT2, AntrocamolLT3 cell survival rate analysis for MIN6 cell.
Fig. 3 A～Fig. 3 C represents that the glucose of Antrodia Camphorata extract ANCA-D, ANCA-W and Antrodia Camphorata compound AntrocamolLT1, AntrocamolLT2, AntrocamolLT3, Antroquinonol stimulates lower insulin releasing (GSIS) test.
Detailed description of the invention
The extraction of Antrodia Camphorata composition
Take Antrodia Camphorata (Antrodiacamphorata) mycelium, after sporophore or the mixture of the two (1.0kg) extract 2 times with the ethanol of 10 times amount, merge concentration to obtain and slightly take out thing and be about 230g (LT-E), slightly take out thing and be allocated extraction 3 times with methylene chloride/water (1:1), it is divided into dichloromethane layer to be about 102.6g (ANCA-D) and water layer is about 127.4g (ANCA-W), take dichloromethane layer 6.0g with silica gel column chromatography through normal hexane/dichloromethane (1:4), dichloromethane, the solvent of ethanol/methylene (5:95) separates, it is divided into ANCA-E-D-1, ANCA-E-D-2, ANCA-E-D-3, ANCA-E-D-4 etc. four layers.The acquirement of above-mentioned four layers is respectively as follows: merging normal hexane/dichloromethane (1:4) and dichloromethane is ANCA-E-D-1, it is ANCA-E-D-2 that ethanol/methylene (5:95) purges with liquid first half, it is ANCA-E-D-3 that ethanol/methylene (5:95) purges with liquid latter half, finally purges with as ANCA-E-D-4 with methanol.
Antrodia Camphorata compound AntrocamolLT1, AntrocamolLT2, AntrocamolLT3
Antrodia Camphorata compound AntrocamolLT1, AntrocamolLT2, AntrocamolLT3 are inventor's purified three compounds obtained in Antrodia Camphorata extract, precisely because purification process and Structural Identification have been exposed in previous application, at this, it is no longer repeated, only briefly disclose its structural formula and simple information thereof, as follows:
AntrocamolLT1 is colourless product liquid, and the molecular formula of this compound is C by analysis24H38O5, molecular weight is 406, and complete Chinese illustrious name is called 4-hydroxyl-2,3-dimethoxy-6-methyl-5-(9-hydroxyl-3,7,11-trimethyls-2,6,10-12 carbon triolefin)-2-cyclonene, 4-hydroxy-5-[9-hydroxy-3,7,11-trimethyldodeca-2,6,10-trienyl]-2,3-dimethoxy-6-methyl-cyclohex-2-enone, its structural formula is such as shown in Formula II:
AntrocamolLT2: for colourless product liquid, the molecular formula of this compound is C by analysis26H40O6；Molecular weight is 448, complete Chinese illustrious name is called 4-acetyl carboxyl-2, and 3-dimethoxy-6-methyl-5-(9-hydroxyl-3,7,11-trimethyl-2,6,10-ten two carbon triolefins)-2-cyclonene, 4-acetoxy-5-[9-hydroxy-3,7,11-trimethyldodeca-2,6,10-trienyl]-2,3-dimethoxy-6-methyl-cyclohex-2-enone.Its structural formula is such as shown in formula III:
AntrocamolLT3: for colourless product liquid, the molecular formula of this compound is C by analysis24H38O5；Molecular weight is 406；, complete China and British title is (4R, 5R, 6R)-4-hydroxyl 5-[(2E respectively, 6E, 9E)-11-hydroxyl-3,7,11-trimethyls-ten two-2,6,9-trialkenyl]-2,3-dimethoxy-6-methyl-cyclohexyl-2-ketenes, (4R, 5R, 6R)-4-hydroxy-5-[(2E, 6E, 9E)-11-hydroxy-3,7,11-trimethyldodeca-2,6,9-trienyl]-2,3-dimethoxy-6-methylcyclohex-2-enone.Its structural formula is such as shown in Formulas I V:
Chinese called after 4-hydroxyl-2,3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon the triolefin)-2-cyclonene of Antroquinonol compound；English called after 4-hydroxy-2,3-dimethoxy-6-methy-5 (3,7,11-trimethyl-dodeca-2,6,10-trienyl)-cyclohex-2-enone), the structure of this compound represents with Formula V:
Above AntrocamolLT1, AntrocamolLT2, AntrocamolLT3 and Antroquinonol have similar main structure, and its formula can represent shown in formula I:
Wherein, R1 is hydrogen or acetyl group, and R2 is
Wherein to be hydrogen, R2 be the R1 of this compoundRepresent with formula (V):
About the details such as extraction and purification of above-mentioned four kinds of Antrodia Camphorata compounds, see the previous related application of inventor.Owing to such compound previously application case disclosing successively, there is multiple medical functions, related experiment is carried out with these four kinds of compounds at this, detect its impact for insulin secretion, examine whether, for diseases relevant to insulin secretion such as diabetes, also there is therapeutic potential.
The cell survival detection of Antrodia Camphorata extract/compound
It is respectively directed to MIN6 mouse islets β cell and carries out cell survival detection (MTTcellviabilityassay).MIN6 mouse islets β cell strain is that SV40 transfects, by T cell, the islet cell tumor strain that non obese diabetic mice (NOD Mus) obtains, and is a kind of mouse islets element tumor cell strain with beta Cell of islet physiological property.
MIN6 cell is cultivated
MIN6 cell strain is incubated in the DMEM high glucose medium containing 15% hyclone, 50 μm of ol/L mercaptoethanols, 100U/ml penicillin and 100mg/ml streptomycin, changes liquid every other day.
Cell survival rate analyzes (MTTAssay)
MIN6 is made 1x105The cell suspending liquid of/ml, it is inoculated in 96 porose discs, every hole 100 μ l, after cell attachment, change 0.2% serum free culture system liquid and cultivate 24h, make cell remain static, Antrodia Camphorata extract/the compound (experimental group) of the BSA culture medium and various predetermined concentration that are then respectively adding 200mg/L reacts 24h, adding endoplasmic reticulum calcium ion side Pu inhibitor TG (Thapsigargin) and react 24h, matched group adds 100 μ l culture fluid, is placed in 37 degree of C, 5%CO2Constant incubator in cultivate certain time.Before terminating, the every hole of 4h adds 20 μ lMTT (0.5mg/ml) continuation cultivation 4h, carries out vibration and makes crystal fully dissolve, surveys the suction brightness value (A) that every hole wavelength is 570nm on detector.Cell viability is calculated: cell survival rate=(the experimental group average A570/ average A570 of matched group) x100% by following equation.
Antrodia Camphorata extract ANCA-D, ANCA-W are for the impact of MIN6 cell survival rate
Consult Figure 1A, each group of cell is added variable concentrations ANCA-D extract (6.25,12.5,25,50,100ng/ml) react 24 hours, add after TG (Thapsigargin) reacts 24h and survey its cell survival rate.Thapsigargin is a kind of endoplasmic reticulum calcium ion side Pu inhibitor, can promote the emptying of endocytoplasmic reticulum calcium ion, and then open calcium pond regulation and control calcium channel, cause intracellular calcium to rise, and then can suppress the secretion of insulin.
Result is as shown in Figure 1A, after the Antrodia Camphorata extract ANCA-D pretreatment 24 hours with variable concentrations of each group of cell, add endoplasmic reticulum calcium ion side Pu inhibitor TG to react 24 hours, it demonstrates compares with the group only adding TG, carry out the group of pretreatment with the Antrodia Camphorata extract ANCA-D of higher concentration, its cell survival rate has cumulative trend.Being demonstrated by result, Antrodia Camphorata extract ANCA-D, ANCA-W can slightly increase the cell survival rate of MIN6 cell, and slightly present positively related trend with its concentration.
Antrodia Camphorata compound AntrocamolLT1, AntrocamolLT2, AntrocamolLT3 are for the impact of MIN6 cell survival rate
Consulting Fig. 2 A～Fig. 2 C, it demonstrates Antrodia Camphorata compound AntrocamolLT1, AntrocamolLT2, AntrocamolLT3 impact for MIN6 cell survival rate respectively.As shown in the 2nd A figure, comparing with the group only adding TG, AntrocamolLT1 can increase the cell survival rate of MIN6 cell, particularly concentration be 250,500, the group of 1000ng/ml becomes apparent from.
Consult shown in Fig. 2 B, the group only adding TG is compared, AntrocamolLT2 can dramatically increase the cell survival rate of MIN6 cell when low concentration, particularly in the group that concentration is 6.25～25ng/ml, but reach in the group of more than 50ng/ml in concentration, make the cell survival rate of MIN6 start slightly to reduce on the contrary.
Consult shown in Fig. 2 C, the group only adding TG is compared, AntrocamolLT3 is in the group that concentration is below 500ng/ml, it appears that the not cell survival rate of appreciable impact MIN6 cell, and starts to promote the cell survival rate of MIN6 cell in the group of 1000ng/ml.
Glucose stimulates lower insulin releasing (GSIS) test
In order to observe aforementioned Antrodia Camphorata extract, compound for the impact of insulin secretion, it is carry out glucose with MIN6 cell to stimulate lower insulin releasing (GSIS) test.First by MIN6 cell with 1x105The concentration of/ml is inoculated in 24 porose discs, 15%FBSDMEM culture fluid 37 degree of C, 5%CO2Cultivate adherent after, after each hole is separately added into Antrodia Camphorata extract/compound reaction 24hr of the BSA culture medium of 200mg/L and variable concentrations, then the glucose giving 5.5mM/16.7mM respectively stimulates, and carries out insulin assay with enzyme linked immunosorbent analytic process.The simultaneously every porocyte total protein of extracting, surveys protein concentration as correction using BCA method.
Consult Fig. 3 A, its display is with after Antrodia Camphorata extract ANCA-D (100ng/ml and 50ng/ml) of variable concentrations, ANCA-W (200ng/ml and 100ng/ml) pretreatment, the more post-stimulatory insulin releasing result of glucose with 5.5mM/16.7mM.As it can be seen, compare with control group, in the group of the ANCA-D pretreatment of 100ng/ml and 50ng/ml, no matter to be under high glucose (16.7mM)/LG (5.5mM) environment, insulin all be can be observed and increase the result of secretion.But, with in the group of the ANCA-W pretreatment of 200ng/ml and 100ng/ml, compare its insulin secretion does not increase with control group.Result according to this experiment, three kinds of compound Ls T1, LT2, LT3 being further directed to be purified from ANCA-D carry out identical test.
Consult Fig. 3 B, its display is with after Antrodia Camphorata compound L T1 (1000ng/ml and 500ng/ml) of variable concentrations, LT2 (100ng/ml and 50ng/ml), LT3 (500ng/ml and 250ng/ml) pretreatment, the more post-stimulatory insulin releasing result of glucose with 5.5mM/16.7mM.As it can be seen, under high glucose (16.7mM)/LG (5.5mM) environment, it is the most notable that the group showing of LT2 (100ng/ml) goes out its effect promoting insulin secretion, compares with control group and about reaches 2 times.And the group of LT1 (1000ng/ml and 500ng/ml), though if it promotes that amount of insulin secretion not LT2 is notable, but still can be seen that the trend slightly increased.And in the group of LT3, also have the trend slightly promoting insulin secretion with the concentration pretreatment of 250ng/ml.Be can be seen that by the above results, the condition of three kinds of its promotion insulin secretions of compound is different each other, such as LT2 effect when concentration is 100ng/ml is quite notable, but its effect is then had no when 50ng/ml, or LT3 is the effect of its promotion insulin secretion visible under high glucose environment, but under LG environment, then have no its effect, these a little differences are likely to be due to the machine involved by various composition and turn different, first not discuss at this, but in objective terms, still as seen above-mentioned three kinds of compounds its at different conditions presented promote insulin secretion both effectiveness, therefore study further via future, its characteristic can be complied with and develop the medical component of different pharmacological mechanism, using as a kind of medical application for diseases relevant to insulin secretion such as diabetes.
Additionally, the follow-up LT1 that is still further directed to of inventor, and the known compound Antroquinonol close with LT series structure carries out insulin secretion experiment again.
Result consults Fig. 3 C, its display is with after Antrodia Camphorata compound L T1 (1000ng/ml and 500ng/ml) of variable concentrations, Antroquinonol (be called for short Antro) (20uM and 10uM) pretreatment 24 hours, the more post-stimulatory insulin releasing result of glucose with 5.5mM/16.7mM.As shown in the figure, under high glucose (16.7mM)/LG (5.5mM) environment, the group showing of LT1 (500ng/ml) goes out its effect promoting insulin secretion, and effect of stimulation with high glucose (16.7mM) environment is more apparent, compare with control group and about reach 2 times, and the stimulation under LG (5.5mM) environment also has and increases a little.And in the group of LT1 (1000ng/ml), the effect of stimulation of high glucose (16.7mM) environment becomes apparent from, and the stimulation under LG (5.5mM) environment also has the trend of corresponding increase.It will thus be seen that the effect that LT1 promotes insulin secretion seems comparatively notable under high glucose (16.7mM) environment.
Additionally as it can be seen, Antroquinonol seems the effect for stimulating insulin secretion more preferably.Under high glucose (16.7mM)/LG (5.5mM) environment, it it is no matter the effect (comparing with control group) all with obvious stimulation insulin secretion of the group with 10um or 20um pre-treatment, only can reach the amount of insulin secretion of about 2 times with the group of the Antroquinonol pre-treatment of 10um, and more can reach the amount of insulin secretion of about 3 times with the group of the Antroquinonol pre-treatment of 20um.Through this further experiment result, more susceptible of proof LT1 and Antroquinonol has the good effects promoting insulin secretion, but the shutdown turn of its phase still must further be studied.
The compound of Antrodia Camphorata provided by the present invention, extract really have a value in industry for preparing the purposes of medicine promoting insulin secretion, only above narration is only presently preferred embodiments of the present invention explanation, all being skillful in this those skilled in the art when can do other all improvement according to above-mentioned explanation, only these change in spirit and the scope of the claims bounded by still falling within the present invention.
Claims (7)
1. Antrodia Camphorata compound is for preparing a purposes for the medicine promoting insulin secretion, shown in this Antrodia Camphorata compound such as formula (I):
Wherein R1 is hydrogen or acetyl group, and R2 is
2. purposes as claimed in claim 1, wherein to be hydrogen, R2 be the R1 of this compoundRepresent with formula (II):
3. purposes as claimed in claim 1, wherein to be acetyl group, R2 be the R1 of this compoundRepresent with formula (III):
4. purposes as claimed in claim 1, wherein to be hydrogen, R2 be the R1 of this compoundRepresent with formula (IV):
5. purposes as claimed in claim 1, wherein to be hydrogen, R2 be the R1 of this compoundRepresent with formula (V):
6. an Antrodia Camphorata extract is for preparing the purposes of the medicine promoting insulin secretion.
7. purposes as claimed in claim 5, wherein this extract is to obtain so that the following step carries out extracting: takes and merges concentration after Antrodia Camphorata mycelium, sporophore or the mixture of the two extract 2 times with the ethanol of 10 times amount and obtain one and slightly take out thing, this is slightly taken out thing and is allocated extraction 3 times with methylene chloride/water (1:1), to be divided into a dichloromethane layer and a water layer, wherein this dichloromethane layer and this water layer are this Antrodia Camphorata extract.
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Citations (4)
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|---|---|---|---|---|
| GB2453808A (en) * | 2007-10-19 | 2009-04-22 | Golden Biotechnology Corp | Novel compounds from antrodia camphorata |
| CN101417934A (en) * | 2007-10-24 | 2009-04-29 | 国鼎生物科技股份有限公司 | New compounds separated from Antrodia camphorate extract |
| CN103908445A (en) * | 2011-12-30 | 2014-07-09 | 国鼎生物科技股份有限公司 | Use Of Compound For Preparing Composition For Treating Diabetes |
| TW201529066A (en) * | 2014-01-22 | 2015-08-01 | Nat Univ Dong Hwa | Compounds from antrodia camphorate and their use in treatment of diabetes mellitus |
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2014
- 2014-12-23 CN CN201410811323.9A patent/CN105769834A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2453808A (en) * | 2007-10-19 | 2009-04-22 | Golden Biotechnology Corp | Novel compounds from antrodia camphorata |
| CN101417934A (en) * | 2007-10-24 | 2009-04-29 | 国鼎生物科技股份有限公司 | New compounds separated from Antrodia camphorate extract |
| CN103908445A (en) * | 2011-12-30 | 2014-07-09 | 国鼎生物科技股份有限公司 | Use Of Compound For Preparing Composition For Treating Diabetes |
| TW201529066A (en) * | 2014-01-22 | 2015-08-01 | Nat Univ Dong Hwa | Compounds from antrodia camphorate and their use in treatment of diabetes mellitus |
Non-Patent Citations (1)
| Title |
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| PO-CHENG CHIANG 等: "Antroquinonol displays anticancer potential against human hepatocellular carcinoma cells: A crucial role of AMPK and mTOR pathways", 《BIOCHEMICAL PHARMACOLOGY》 * |
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Application publication date: 20160720 |