CN103641882A - Novel 2,3-dihydroxyl-30-noroleanolic acid as well as preparation method and application thereof in preparing glycosidase inhibitor medicament - Google Patents
Novel 2,3-dihydroxyl-30-noroleanolic acid as well as preparation method and application thereof in preparing glycosidase inhibitor medicament Download PDFInfo
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Abstract
The invention discloses novel 2,3-dihydroxyl-30-noroleanolic acid as well as a preparation method thereof and application thereof in preparing a glycosidase inhibitor medicament. According to the novel 2,3-dihydroxyl-30-noroleanolic acid as well as a preparation method thereof and application thereof disclosed by the invention, a strong-effect alpha-glucosidase inhibitor is extracted and separated from akebia plants, and the plants are rich in resource. Moreover, when fruit extraction is adopted, the plants are utilized for a long time without being damaged, so that not only can economic benefits be improved, but also environmental friendliness can be achieved. A pharmacological experiment shows that a compound 2,3- dihydroxyl-23-aldehyde group-nor olean-12,20(29)-diene-28-acid has in-vitro alpha-glucosidase-inhibitory activity stronger than that of a first-line diabetes medicament acarbose, is expected to be further developed into a medicament for preventing and treating type II diabetes mellitus, and has good application and development potentials.
Description
Technical field:
The invention belongs to Natural Medicine Chemistry field, be specifically related to a new 30-and fall volatile oil acids pentacyclic triterpene compound, 2, olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, 20 (29)-diene-28-acid, and the method for separating and preparing of this compound and this compound or its pharmaceutically useful salt or the application of its esterified derivative in preparing glycosidase inhibitor.
Background technology:
Along with social progress and the raising of people's living standard, the sickness rate of diabetes improves in the world, has especially the morbidity that surpasses 100,000,000 people in China, and presents the trend increasing year by year.Diabetes are clinical common endocrine metabolism dysfunctional disease, and the occurred frequently year by year of itself and cardiovascular disease and cancer etc. has an important dependency, is the potential important killer of human health.Diabetes Zheng Gei China people ' s health and national economy cause more and more great loss.
Diabetes doctor trained in Western medicine be divided into insulin-dependent diabetes mellitus (IDDM) (or claim insulin-dependent, DM1) and type II diabetes (or claim non-insulin-dependent, DM2), wherein type II diabetes morbidity, with morbidity all far above insulin-dependent diabetes mellitus (IDDM), thereby endangers larger.Competitive alpha-glucosidase inhibitor can effectively be postponed glucide and be digested and assimilated, alleviates kidney burden, controls blood sugar after meal and sharply raise and then can make the variation fluctuating range of blood sugar concentration reduce, thereby they have good potential quality in exploitation aspect prevention and treatment type II diabetes medicine.Having developed at present listing and positive clinic trial makes the important alpha-glucosidase inhibitor for the treatment of type II diabetes one line medication and comprises acarbose(acarbose), voglibose, miglitol and emigliate etc.
The traditional Chinese medical science often claims that diabetes are diabetes, according to Compendium of Materia Medica, records, and the single medicinal material that can be used for treating diabetes has nearly 200 kinds, shows that from plant origin, excavating new alpha-glucosidase inhibitor has very big potentiality.Existing studies show that, Lardizabalaceae Three Akebia Decne Species is rich in triterpene and falls triterpene compound, but the general study of relevant its chemical composition and pharmacologically active is deep not enough.According to the literature, triterpene and fall triterpene compound there is important potential quality aspect alpha-glucosidase inhibitor, thereby corresponding deducibility, Three Akebia Decne Species should have important potentiality excavating aspect the alpha-glucosidase inhibitor of new safety.
Summary of the invention:
First object of the present invention is to provide a kind of new 29-with alpha-glucosidase inhibition activity and falls triterpene new compound-2, olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, 20 (29)-diene-28-acid, that is 2 α, 3 β-dihydroxy-23-oxo-30-nor olean-12,20 (29)-dien-28-oic acid.
Second object of the present invention is to provide a kind of compound 2, olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, the preparation method of 20 (29)-diene-28-acid, it is characterized in that, compound 2, olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, 20 (29)-diene-28-acid is from akebi (Akebia quinata (Thumb.) Decne.), threeleaf akebia (Akebia trifolia (Thumb.) Koidz), long order akebi (Akebia longeracemosa Matsumura), the stem of Caulis Akebiae (Akebia trifolia (Thumb.) Koidz.Var.australis (Diels) Rehd) and long calyx threeleaf akebia (Akebia trifolia (Thumb.) Koidz..subsp.Longisepala H.N.Qin), in leaf or fruit, preparation separation obtains.Concrete material can be dry product or fresh goods, the fruit dry product of preferred plant.
Concrete steps are preferably:
A, prepare total medicinal extract: will akebi, stem, leaf or the fruit of threeleaf akebia, Caulis Akebiae or long order akebi pulverize after with aqueous ethanolic solution, ethanol, aqueous acetone solution or acetone extraction, concentrated ethanol or the acetone removed of extracting solution, obtain total medicinal extract crude extract, total medicinal extract crude extract is suspended in water, with petroleum ether extraction, petroleum ether extract obtains the total medicinal extract of sherwood oil after concentrated;
B, separation and purification: the total medicinal extract of sherwood oil is through purification on normal-phase silica gel column chromatography, take sherwood oil/acetone as eluent, from volume ratio 90:10,85:15,7:3,6:4,0:100 gradient elution, collects sherwood oil/acetone 6:4v/v eluting fraction, through MCI column chromatography, decolour, by methanol-eluted fractions, collect methanol-eluted fractions part, then through purification on normal-phase silica gel column chromatography purification, with chloroform/methanol 98:2v/v wash-out, must be as shown in formula I 2, olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, 20 (29)-diene-28-acid.
Described aqueous ethanolic solution or aqueous acetone solution are preferably volume fraction and are more than or equal to 70% aqueous ethanolic solution or aqueous acetone solution.
The 3rd object of the present invention is to provide 2,3-dihydroxyl-23-aldehyde radical-30-and falls olea-12,20 (29)-diene-28-acid, its pharmaceutically useful salt or the application of its esterified derivative in preparing alpha-glucosidase inhibitor medicament.
The 4th object of the present invention is to provide a kind of alpha-glucosidase inhibitor medicament, it is characterized in that, the compound 2 that contains significant quantity, olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, 20 (29)-diene-28-acid or its pharmacologically acceptable salt or its esterified derivative, and pharmaceutically commonly use auxiliary material or carrier.
The 5th object of the present invention is to provide stem, leaf or the fruit of akebi, threeleaf akebia, long order akebi, Caulis Akebiae and long calyx threeleaf akebia and preparing compound 2, olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, the application in 20 (29)-diene-28-acid.
The present invention adopts separated potent alpha-glucosidase inhibitor-2 of extraction the Three Akebia Decne Species extensively distributing from China, olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, 20 (29)-diene-28-acid, its material source is abundant, preparation process easy handling, and when adopting fruit to extract, can also make plant itself be utilized for a long time without destruction, when obtaining better economic benefit, can also be environmentally friendly.And the alpha-glucosidase of this compound suppresses activity even apparently higher than clinical application acarbose, the alpha-glucosidase inhibitor medicine that is further development of most probably new, effective, safe prevention and treatment type II diabetes, has the potential good prospect of marketing.
Accompanying drawing explanation:
Fig. 1 is compound 2, and olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, 20 (29)-diene-28-acid
1h NMR collection of illustrative plates;
Fig. 2 is compound 2, and olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, 20 (29)-diene-28-acid
13c NMR collection of illustrative plates;
Fig. 3 is compound 2, and olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, the HMBC collection of illustrative plates of 20 (29)-diene-28-acid.
Embodiment:
Following examples are to further illustrate of the present invention, rather than limitation of the present invention, and the simple modifications that essence according to the present invention is carried out the present invention all belongs to the scope of protection of present invention.
Embodiment 1: in Trilobed Caulis Akebiae fruit 2, olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, the preparation of 20 (29)-diene-28-acid
1.1 instruments and reagent
Concentrating under reduced pressure adopts the Tokyo N-1000 of physics and chemistry company Rotary Evaporators, the circulating cooling tank of CCA-1110 and SB-1000 electric-heated thermostatic water bath; HPLC adopts the Japanese Shimadzu LC-20AT of company type liquid chromatograph, SPD-M20A detector and Shim-PackPRC-ODS chromatographic column (particle diameter 5 μ m, aperture 12nm, 250mm * 20mm); Electrospray ionization mass spectrum (ESIMS) adopts the MDS SCIEX API2000LC/MS/MS of Applied biosystems instrument, take methyl alcohol as solvent direct injection mensuration;
1h NMR spectrum and
13c NMR spectrum adopts Bruker advance600 nuclear magnetic resonance analyser, and take tetramethylsilane as interior mapping fixed.Coloration method adopts 10% ethanol solution of sulfuric acid or sulfuric acid Vanillin to process post-heating colour developing or iodine vapor colour developing.
1.2 plant origins and evaluation
For the fruit sample that extracts vegetable material threeleaf akebia (Akebia trifolia (Thumb.) Koidz.), in September, 2009, pick up from Hunan Province domestic, by South China Botanical Garden Chinese Academy of Sciences, Xing Fuwu researcher identifies.
1.3 extract with separated
Sample (Trilobed Caulis Akebiae fruit dry product weighs 1.0 kilograms) is pulverized rear with extracting three times under volume fraction 95% ethanol room temperature, and merging filtrate concentrating under reduced pressure is removed organic solvent ethanol, obtains total medicinal extract crude extract.Total medicinal extract crude extract is suspended in 500ml water, and with isopyknic Petroleum ether extraction three times, petroleum ether extraction liquid obtains the total medicinal extract of sherwood oil (16g) through concentrating under reduced pressure.By sherwood oil total for medicinal extract acetone (150mL) dissolve, adding purification on normal-phase silica gel (80-100 order) to mix sample with weight ratio 1:1.5 volatilizes, dry column-packing (200-300 order, 300 grams) dry method loading, use successively sherwood oil/acetone=90:10,85:15,7:3,6:4,0:100v/v is that eluent gradient wash-out obtains 5 component F1 – F5; The cut F4 of sherwood oil/acetone 6:4v/v wash-out is decoloured through MCI column chromatography again, by methanol-eluted fractions, collect methanol-eluted fractions part, again through purification on normal-phase silica gel column chromatography purification, with chloroform/methanol 98:2v/v wash-out, pure compound 1(2 that must be as shown in formula I, olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, 20 (29)-diene-28-acid) (4mg).
1.4 compounds 2, olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, the Structural Identification of 20 (29)-diene-28-acid
Institute's compound that obtains 1 is white amorphous powder, and molecular formula is C
29h
42o
5, its
1h NMR collection of illustrative plates,
13c NMR collection of illustrative plates and HMBC collection of illustrative plates are as shown in Figure 1,2 and 3.
eSI-MS (+) m/z493[M+Na]
+; ESI-MS (-) m/z469[M-H]
–; HR-ESI-MS (pos.) m/z493.2922[M+Na]
+(calcd for C
29h
42naO
5, 493.2924);
1h-NMR (pyridine-d
5, 600MHZ) and
13c-NMR (pyridine-d
5, 150MHZ) data are as shown in table 1:
Table 1.2, olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, the NMR data of 20 (29)-diene-28-acid
According to the comprehensive analysis of the spectral datas such as above mass spectrum and nuclear-magnetism, the structure that analytic derivation goes out this new compound is 2, and olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, 20 (29)-diene-28-acid, and its structural formula is as shown in formula I
Embodiment 2: in threeleaf akebia cauline leaf 2, olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, the preparation of 20 (29)-diene-28-acid
2.1 instruments and reagent: with embodiment 1
2.2 plant origins and evaluation: with embodiment 1
2.3 extract with separated
Sample (1.0 kilograms of threeleaf akebia cauline leaf dry products) extracts three times by volume fraction 95% ethanol room temperature after pulverizing, and merging filtrate concentrating under reduced pressure obtains total medicinal extract crude extract.Total medicinal extract crude extract is suspended in 500ml water, uses equal-volume Petroleum ether extraction three times, extraction liquid obtains the total medicinal extract of sherwood oil (13g) through concentrating under reduced pressure.By sherwood oil total for medicinal extract acetone (150mL) dissolve, adding purification on normal-phase silica gel (80-100 order) to mix sample with weight ratio 1:1.5 volatilizes, dry column-packing (200-300 order, 300 grams) dry method loading, use successively sherwood oil/acetone=90:10,85:15,7:3,6:4,0:100v/v is that eluent gradient wash-out obtains 5 component F1 – F5; The cut F4 of sherwood oil/acetone 6:4v/v wash-out is decoloured through MCI column chromatography again, by methanol-eluted fractions, collect methanol-eluted fractions part, again through purification on normal-phase silica gel column chromatography purification, with chloroform/methanol 98:2v/v wash-out, pure compound 2 that must be as shown in formula I, olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, 20 (29)-diene-28-acid (2.5mg).
Embodiment 3:
Stem, leaf or the fruit of akebi, long order akebi, Caulis Akebiae and long calyx threeleaf akebia of take is sample, according to the extraction described in embodiment 1 and separation method final purification, obtain the pure compound 2 of formula I, olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, 20 (29)-diene-28-acid.
Embodiment 4:2, olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, and the alpha-glucosidase of 20 (29)-diene-28-acid suppresses active and detects
4.1 instruments and reagent
Laboratory apparatus: microplate reader Genois microplate reader(Tecan GENios, Swizerland)
Reagent and compound sample: alpha-glucosidase is purchased from Sigma Chemical Co.(Sigma-Aldrich, St.Louis, USA); 4-nitrophenol-alpha-D-glucose pyrans glycosides (PNPG) is purchased from Tokyo Chemical Industry Co., Ltd. (Japan); Acarbose (Acarbose), purchased from Tokyo Chemical Industry Co., Ltd. (Japan); Olea-12 fall in 2,3-dihydroxyl-23-aldehyde radical-30-, and 20 (29)-diene-28-acid is prepared by above experimental example
4.2 testing method:
A) compounding pharmaceutical solution: by 2, olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, 20 (29)-diene-28-acid and acarbose are prepared respectively the solution of 10mg/ml by dimethyl sulfoxide (DMSO), and prepare the phosphoric acid buffer (ultrapure water preparation) of 67mM, PNPG substrate solution (5mM, phosphoric acid buffer is prepared), and the NaCO of 0.2M
3solution (phosphoric acid buffer preparation).
B) adopt colorimetry, by 96 porocyte culture plates, with regard to compound 2, olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, and 20 (29)-diene-28-acid is measured the half-inhibition concentration of alpha-glucosidase.First the alpha-glucosidase of 20 μ L (0.8U) is joined in sample well, then will test sample solution dilutes by a certain percentage with phosphoric acid buffer, every hole adds sample solution 120 μ L, make the ultimate density of testing sample be: 500 μ g/mL, 250 μ g/mL, 125 μ g/mL, 62.5 μ g/mL, 31.25 μ g/mL, 15.625 μ g/mL, finally add reaction substrate 4-nitrophenol-α-D-glucopyranoside 20 μ L (5mM) again.After 37 ℃ of water-bath 15min, in each sample well, add the NaCO of 80 μ L
3(0.2M) termination reaction, in the place's colorimetric estimation of 405nm wavelength.The phosphoric acid buffer of same volume replaces enzyme solution.Compound inhibiting rate is calculated for blank and contrast OD value by sample OD value, and calculation formula is as follows: inhibiting rate (%)=(OD
control– OD
neg)-(OD
test– OD
test control)/(OD
control– OD
neg) * 100%.Wherein test compounds 2, and olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, the half-inhibition concentration (IC of 20 (29)-diene-28-acid to alpha-glucosidase
50) by dose effect curve, obtained.
4.3 experimental datas are referring to table 2:
Table 2.2, olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, and the a-Glucosidase inhibitor of 20 (29)-diene-28-acid is active
4.4 experiment conclusion:
Experimental result shows, new compound 2, and olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, and 20 (29)-diene-28-acid has the activity of the inhibition a-glucuroide more potent than the ofhypoglycemic medicine acarbose of first-line treatment diabetes.Thereby compound 2, olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, and 20 (29)-diene-28-acid has to further develop becomes the potential quality of preventing and treating type II diabetes medicine, has stronger application and development potential quality.
Claims (7)
1. compound 2, and olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, 20 (29)-diene-28-acid, its pharmaceutically useful salt or its esterified derivative, and its structural formula is as shown in formula I:
2. a compound 2 claimed in claim 1, olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, the preparation method of 20 (29)-diene-28-acid, it is characterized in that, compound 2, olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, 20 (29)-diene-28-acid is from akebi (Akebia quinata (Thumb.) Decne.), threeleaf akebia (Akebia trifolia (Thumb.) Koidz), long order akebi (Akebia longeracemosa Matsumura), the stem of Caulis Akebiae (Akebia trifolia (Thumb.) Koidz.Var.australis (Diels) Rehd) and long calyx threeleaf akebia (Akebia trifolia (Thumb.) Koidz..subsp.Longisepala H.N.Qin), in leaf or fruit, preparation separation obtains.
3. preparation method according to claim 2, is characterized in that, concrete steps are:
A, prepare total medicinal extract: will akebi, stem, leaf or the fruit of threeleaf akebia, Caulis Akebiae or long order akebi pulverize after with aqueous ethanolic solution, ethanol, aqueous acetone solution or acetone extraction, concentrated ethanol or the acetone removed of extracting solution, obtain total medicinal extract crude extract, total medicinal extract crude extract is suspended in water, with petroleum ether extraction, petroleum ether extract obtains the total medicinal extract of sherwood oil after concentrated;
B, separation and purification: the total medicinal extract of sherwood oil is through purification on normal-phase silica gel column chromatography, take sherwood oil/acetone as eluent, from volume ratio 90:10,85:15,7:3,6:4,0:100 gradient elution, collects sherwood oil/acetone 6:4v/v eluting fraction, through MCI column chromatography, decolour, by methanol-eluted fractions, collect methanol-eluted fractions part, then through purification on normal-phase silica gel column chromatography purification, with chloroform/methanol 98:2v/v wash-out, must be as shown in formula I 2, olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, 20 (29)-diene-28-acid.
4. preparation method according to claim 3, is characterized in that, described aqueous ethanolic solution or aqueous acetone solution are that volume fraction is more than or equal to 70% aqueous ethanolic solution or aqueous acetone solution.
5. claimed in claim 12, olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, 20 (29)-diene-28-acid, its pharmaceutically useful salt or the application of its esterified derivative in preparing alpha-glucosidase inhibitor medicament.
6. an alpha-glucosidase inhibitor medicament, it is characterized in that, the compound claimed in claim 12 that contains significant quantity, olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, 20 (29)-diene-28-acid or its pharmacologically acceptable salt or its esterified derivative, and pharmaceutically commonly use auxiliary material or carrier.
7. stem, leaf or the fruit of akebi, threeleaf akebia, long order akebi, Caulis Akebiae and long calyx threeleaf akebia are at preparation compound 2 claimed in claim 1, and olea-12 fall in 3-dihydroxyl-23-aldehyde radical-30-, the application in 20 (29)-diene-28-acid.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106265681A (en) * | 2016-07-20 | 2017-01-04 | 中国科学院华南植物园 | Compound 2 α, 3 β dihydroxy 23 aldehyde radical olive 12 alkene 28 acid application in preparing glycosidase inhibitor |
| CN109810084A (en) * | 2019-03-02 | 2019-05-28 | 中国科学院昆明植物研究所 | Paeonilactiflorol and its pharmaceutical composition and preparation method and application |
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| CN103404514A (en) * | 2013-08-27 | 2013-11-27 | 中国科学院华南植物园 | Preparation method of 2alpha, 3beta-dihydroxyl oleanane-13(18)-ene-28-acid and application of 2alpha, 3beta-dihydroxyl oleanane-13(18)-ene-28-acid in preparing antibacterial agent |
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| JPS608224A (en) * | 1983-06-29 | 1985-01-17 | Takuo Kosuge | Carcinostatic agent |
| CN103404514A (en) * | 2013-08-27 | 2013-11-27 | 中国科学院华南植物园 | Preparation method of 2alpha, 3beta-dihydroxyl oleanane-13(18)-ene-28-acid and application of 2alpha, 3beta-dihydroxyl oleanane-13(18)-ene-28-acid in preparing antibacterial agent |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106265681A (en) * | 2016-07-20 | 2017-01-04 | 中国科学院华南植物园 | Compound 2 α, 3 β dihydroxy 23 aldehyde radical olive 12 alkene 28 acid application in preparing glycosidase inhibitor |
| CN109810084A (en) * | 2019-03-02 | 2019-05-28 | 中国科学院昆明植物研究所 | Paeonilactiflorol and its pharmaceutical composition and preparation method and application |
| CN109810084B (en) * | 2019-03-02 | 2022-04-19 | 中国科学院昆明植物研究所 | Paeonilactiflorol, pharmaceutical composition thereof, preparation method and application thereof |
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