CN106983763A - Single galactosyl diacylglycerol ester and preparation method thereof and purposes - Google Patents
Single galactosyl diacylglycerol ester and preparation method thereof and purposes Download PDFInfo
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- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7032—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a polyol, i.e. compounds having two or more free or esterified hydroxy groups, including the hydroxy group involved in the glycosidic linkage, e.g. monoglucosyldiacylglycerides, lactobionic acid, gangliosides
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Abstract
Have the invention discloses one kind such as formula（Ⅰ）Single galactosyl diacylglycerol ester of shown structure and preparation method thereof and for preparing PPARαActivator and PPARα/γThe purposes of double agonists.（Ⅰ）Wherein：R1And R2Acyl moieties are represented, the acyl moieties are the straight or branched aliphatic acid containing 1 30 carbon atoms；And containing 0 15 cis or trans double bonds in acyl moieties.Present invention firstly discovers that single galactosyl diacylglycerol ester is to PPARαAgonism and to PPARα/γDouble excitations effect, disclose such compound preventing and treating PPARs relevant diseases in application value.In addition, present invention discover that and separated marine alga and be beneficial to the active component of cardiovascular health, provide effective substance and function factor for exploitation marine alga medicine, health food, food.
Description
Technical field
The present invention relates to a kind of preparation method and purposes of single galactosyl diacylglycerol ester, specifically, it is related to one
Plant the preparation method and its use as PPAR alfa agonists and PPAR alpha/gamma double agonists of single galactosyl diacylglycerol ester
On the way.
Background technology
Peroxisome proliferation-activated receptors (peroxisome proliferator-activated
Receptors, abbreviation PPARs) be nuclear receptor superfamily a member, including PPAR α, PPAR β (or PPAR δ) and PPAR γ tri-
Plant hypotype.PPARs is first formed different dimerization after ligand activation with retinoid acceptor X (retinoidX receptor, RXR)
Body, then with Peroxisome proliferators responsive element (the peroxisome proliferator of target gene promoters upstream
Response element, PPRE) combine, lipid-metabolism, fat generation, insulin are regulated and controled by the transcriptional regulatory of target gene
The important biochemical reaction process such as sensitivity, inflammatory reaction, cell growth and differentiation.A series of metabolic syndromes are all related to PPARs,
Including insulin resistance, impaired glucose tolerance, obesity, hyperlipidemia, high blood pressure, atherosclerosis and Microalbuminuria
Deng.Therefore, PPARs receives much concern always as the important target spot of mankind's metabolism related diseases protective agents.
Compound and PPAR binding site are ligand binding domain (LBD), are the active region of ligand-dependent, X-ray monocrystalline
Diffraction confirms that 3 kinds of PPAR LBD possesses similar three-dimensional structure, but the internal structure of ligand binding pocket is different.PPAR β's
There is the place of obvious stenosis in binding pocket, this prevent many relatively large PPAR α and PPAR γ part from
PPAR β are combined.In PPAR α and PPAR γ, after part is combined with LBD, mutual configuration can change, the acid head of part
Hydrogen bond is formed between some specific amino acid residues on portion's group (c-terminus of such as aliphatic acid) and LBD, this hydrogen bond is exactly
The switch of PPAR receptor activations.Therefore, in compound contain carboxyl or similar structures (carbonyl or ester group), be likely to
LBD formation hydrogen bonds, so as to activate PPARs.Due to the position in LBD with the amino acid residue of ligand binding formation hydrogen bond and species
And differ, therefore, different compounds may only activate a kind of PPAR acceptors, it is also possible to while activating two kinds of PPAR acceptors.Institute
With again PPAR activator has single activator, point of double agonists.
PPAR alfa agonists can promote lipid metabolism, increase the synthesis of HDL.Gemfibrozil, fenofibrate,
The medicines such as Clofibrate are PPAR alfa agonists, clinically for treating dyslipidemia, with preferable effect for reducing fat.PPAR α by
Body activator can also suppress various transcription factors, inflammatory mediator and adhesion molecule, alleviate albuminuria, prevent glomerulus loose, right
Treat obesity, hypertension, atherosclerosis, NASH and diabetic nephropathy effective.
PPAR gamma agonists improve insulin sensitivity by promoting aliphatic acid to store and suppress Fatty synthesis.Thiophene
Oxazolidinedione class (TZD) medicine such as Pioglitazone, Rosiglitazone etc. are all PPAR gamma agonists, clinically as insulin sensitivity enhancing
Agent is used for the treatment of diabetes B.But, PPAR gamma agonists also promote glucose to be transported to adipose tissue simultaneously, and this may
Weight in patients can be caused to increase.
Currently, can hypoglycemic again can lipid-loweringing PPAR alpha/gamma double agonists discovery turn into focus.PPAR alfa agonists energy
Animal ingestion and fat deposition, the oxidative metabolism for promoting Liver lipids are reduced, so as to mitigate body weight caused by PPAR gamma agonists
Increase side effect.Research shows that PPAR α/γ dual agonists can not only reduce triacylglycerol and increasing high density lipoprotein,
Treatment is fat and improvement angiocardiopathy aspect has preferable effect, such as dyslipidemia, atherosclerosis, hypertension, cardiac muscle
Plumpness, ischemical reperfusion injury, autoimmune myocarditis；And insulin sensitivity can also be improved, adiponectin is adjusted, is played
The effect of anti-diabetic, also has therapeutic action to NASH and diabetic nephropathy.With single PPAR gamma agonists
Compare, PPAR α/γ dual agonists have more preferable security.
Single galactosyl diacylglycerol ester (monogalactosyldiacylglycerol, MGDG), is plant leaf green
The important composition composition of body film fat, chemical name is the-O- fatty acyl group -3-O- β-D- galactopyranose-sn- glycerine of 1,2- bis-.
MGDG is not only plant and microorganism photosynthetic membrane important composition composition, also with diversified physiologically active：It can participate in thin
Born of the same parents recognize, the activity such as signal transduction, and with antitumor, AntiHIV1 RT activity, anti-inflammatory, anti-oxidant, fouling resistance isoreactivity.At present, have no
MGDG is used as PPAR alfa agonists, the document report of especially PPAR α/γ dual agonists purposes.
The content of the invention
In view of the above-mentioned problems, first purpose of the present invention is to provide a kind of single galactosyl diacylglycerol ester compounds
It is used as the purposes of PPAR alfa agonists or PAR alpha/gamma double agonists.
It is a further object to provide the preparation method of above-mentioned single galactosyl diacylglycerol ester.
Single galactosyl diacylglycerol ester with the structure as shown in formula (I) is used to prepare PPAR alfa agonists or PPAR
The purposes of alpha/gamma double agonists.
Wherein：R1And R2Acyl moieties are represented, the acyl moieties are the straight or branched fat containing 1-30 carbon atom
Acid；And containing 0-15 cis or trans double bond in acyl moieties.
Further, single galactosyl diacylglycerol ester with the structure as shown in formula (I) prepare be used to improving with
PPAR alpha associated disorders, such as dyslipidemia, obesity, hypertension, atherosclerosis, NASH, diabetic nephropathy
Purposes in medicine.
Further, it is used as PPAR α/γ bidifly with single galactosyl diacylglycerol ester of structure as shown in formula (I)
Dynamic agent treatment PPARs relevant diseases, such as diabetes B is fat, dyslipidemia, hypertension, atherosclerosis, non-alcoholic
Purposes in fatty liver, diabetic nephropathy, myocardial hypertrophy, ischemical reperfusion injury, the medicine of autoimmune myocarditis.
It is preferred that, the acyl moieties are the straight chain fatty acid containing 6-24 carbon atom, and suitable containing 1-6 in acyl moieties
Formula double bond.
It is furthermore preferred that the acyl moieties are the straight chain fatty acid containing 16-20 carbon atom, and contain 1-5 in acyl moieties
Individual cis-double bonds.
One of most preferred embodiment, formula (I) compound has the structure as shown in formula (II), and its is entitled：(2S)-
1-O- (5Z, 8Z, 11Z, 14Z- Eicosatetraenoic acyl group) -2-O- (6Z, 9Z, 12Z, 15Z- stearidonic acyl group) -3-O- β -
D- galactopyranosyl glycosyl-sn- glycerine, the purposes for preparing PPAR alfa agonists and PPAR alpha/gamma double agonists.
Further, single galactosyl diacylglycerol ester with the structure as shown in formula (II) prepare be used to improving with
PPAR alpha associated disorders, such as dyslipidemia, obesity, hypertension, atherosclerosis, NASH, diabetic nephropathy
Purposes in medicine.
Further, it is used as PPAR α/γ bidifly with single galactosyl diacylglycerol ester of structure as shown in formula (II)
Dynamic agent treatment PPARs relevant diseases, such as diabetes B is fat, dyslipidemia, hypertension, atherosclerosis, non-alcoholic
Purposes in fatty liver, diabetic nephropathy, myocardial hypertrophy, ischemical reperfusion injury, the medicine of autoimmune myocarditis.
Further, the invention provides a kind of pharmaceutical composition, it contains the structuring as shown in formula (I) or formula (II)
Compound is used as PPAR alfa agonists or PPAR α/γ dual agonists, and pharmaceutically acceptable carrier.
In the present invention, described pharmaceutical composition can be prepared according to method known in the art, can by activity into
Divide and conventional excipients, flavor enhancement, disintegrant, preservative, lubricant, wetting agent, adhesive, solvent, thickener or solubilising
The excipient substances such as agent are mixed, and are made any formulation for being suitable for Clinical practice, such as pulvis, tablet, capsule, granule,
Injection, oral liquid etc..
It is preferred that, described pharmaceutical composition contains the 1-99.9wt% chemical combination having as shown in formula (I) or formula (II)
Thing.
In addition, present invention also offers a kind of preparation method of single galactosyl diacylglycerol ester, it includes following step
Suddenly：
1) using marine alga as raw material, with the aqueous alcohol solutions refluxing extraction 2~5 times of 5-15 times of volume, extract solution, concentration are merged
To without alcohol taste, organic solvent extraction is concentrated to give crude extract；
2) crude extract is purified by silica gel column chromatography repeatedly, Sephadex LH-20 gel filtration chromatographies, obtains single galactolipin
The acyl of base two
The mixture of base glycerol ester type compound；Separated again through high pressure liquid chromatography, obtaining multiple structures as shown in formula (I)
Single half
Lactose base diacylglycerol ester compounds.
Advantages of the present invention：Present invention firstly discovers that agonism of single galactosyl diacylglycerol ester to PPAR α
And PPAR α/γ double excitations is acted on, disclose application value of such compound in preventing and treating PPARs relevant diseases.
In addition, present invention discover that and separated marine alga and be beneficial to the active component of cardiovascular health, for exploitation marine alga medicine, health care food
Product, food provide effective substance and function factor.
Brief description of the drawings
Fig. 1 is MGDG's1H-NMR is composed.
Fig. 2 is MGDG's13C-NMR is composed.
Embodiment
Describe the present invention in detail below in conjunction with the accompanying drawings and by specific embodiment.
Embodiment 1：The extraction preparation of single galactosyl diacylglycerol ester and Structural Identification
Sargassum fusifome 2000g is taken, 2h is extracted with 75% alcohol reflux of 10 times of volumes, is repeated 3 times.Merge extract solution, filter,
No alcohol taste is concentrated into, is extracted 3 times using isometric ethyl acetate, combining extraction liquid, concentration obtains medicinal extract 33.26g.Medicinal extract is through second
Acetoacetic ester is dissolved, and sample is mixed with 41g 200-300 mesh silica gel Hs, and silica gel column chromatography carries out gradient by solvent of methylene chloride-methanol
Elution, wherein methylene chloride-methanol (v/v 95:5) obtained component is eluted, then through Sephadex LH-20 gel filtration chromatographies (two
Chloromethanes-methanol 1:1) mixture of single galactosyl diacylglycerol ester type compound (MGDG) and silica gel column chromatography, is obtained, is surveyed
Its1H-NMR compose and13C-NMR is composed (as illustrated in fig. 1 and 2).
According to Fig. 1's1H-NMR(500MHz,CDCl3):4.21 (1H, dd, J=6.5,11.9Hz, H-1a), 4.39 (1H,
Dd, J=1.9,11.8Hz, H-1b), 5.30 (1H, m, H-2), 3.72 (1H, dd, J=6.2,10.9Hz, H-3a), 3.91 (1H,
M, H-3b), 4.26 (1H, d, J=7.4Hz, H-1'), 3.65 (1H, m, H-2'), 3.54 (1H, m, H-3'), 4.01 (1H, br
S, H-4'), 3.59 (1H, br d, J=9.7Hz, H-5'), 3.84 (1H, dd, J=11.3,3.7Hz, H-6'a), 3.94 (1H,
m,H-6'b),1.27[22H,m,(CH2)n], 0.97 (3H, t, J=7.5Hz, CH3), 0.88 (3H, t, J=7.0Hz, CH3) with
And Fig. 213C-NMR(125MHz,CDCl3):δ62.9(C-1),70.3(C-2),68.4(C-3),104.1(C-1'),71.7
(C-2'),73.6(C-3'),69.5(C-4'),74.7(C-5'),62.7(C-6'),173.9(-CO),173.6(-CO),
29.2-34.4[(CH2)n],14.4(-CH3),14.3(-CH3), it is accredited as single galactosyl diacylglycerol ester (MGDG) chemical combination
The mixture of thing.
MGDG mixtures are separated through Semi-PHPLC again, methanol-water (v/v 95:5→100:0) gradient elution is obtained successively
Compound MD1~MD6.According to HR-MS/MS (as shown in table 1), with reference to GC-MS data, identification of M D1~MD6 structure is successively
For：(2S) -1-O- (6Z, 9Z, 12Z, 15Z- stearidonic acyl group) -2-O- (6Z, 9Z, 12Z, 15Z- stearidonic acyls
Base) -3-O- β-D- galactopyranosyl glycosyl-sn- glycerine (MD1, tR 15.16min)、(2S)-1-O-(5Z,8Z,11Z,14Z,
17Z- eicosapentaenoics acyl group) -2-O- (6Z, 9Z, 12Z, 15Z- stearidonic acyl group) -3-O- β-D- galactopyranosyls glycosyl -
Sn- glycerine (MD2, tR16.74min), (2S) -1-O- (enoyl- of 18 carbon of 9Z, 12Z, 15Z- three) -2-O- (6Z, 9Z, 12Z,
15Z- stearidonics acyl group) -3-O- β-D- galactopyranosyl glycosyl-sn- glycerine (MD3, tR 17.85min)、(2S)-1-O-
(5Z, 8Z, 11Z, 14Z, 17Z- eicosapentaenoic acyl group) -2-O- (enoyl- of 18 carbon of 9Z, 12Z, 15Z- three) -3-O- β-D- pyrroles
Mutter galactosyl-sn- glycerine (MD4, tR19.52min), (2S) -1-O- (5Z, 8Z, 11Z, 14Z- Eicosatetraenoic acyl group) -
2-O- (6Z, 9Z, 12Z, 15Z- stearidonic acyl group) -3-O- β-D- galactopyranosyl glycosyl-sn- glycerine (MD5, tR
19.99min), (2S) -1-O- (enoyl- of 18 carbon of 9Z, 12Z, 15Z- three) -2-O- (the carbon triolefin acyls of 9Z, 12Z, 15Z- 18
Base) -3-O- β-D- galactopyranosyl glycosyl-sn- glycerine (MD6, tR20.73min), wherein MD5 is noval chemical compound.
1 MD1 of table~MD6 HRMS/MS data analyses
Embodiment 2：Activations of the MGDG to PPAR α and PPAR γ
Utilize Relative luciferase activity assay technology for detection PPAR α and PPAR γ transcriptional activation.By 293T
Cell is seeded in 96 orifice plates, DMEM training liquid (10%FBS, without antibiotic), and cell grows to 60% or so after 8-12 hours, no
Liquid is changed, by lipo2000 specifications, direct transfection plasmid.Plasmid total amount is 0.075g/well (0.05 μ g PPRE, 0.005 μ g
Internal reference pRL-TK and 0.02 μ g PPAR α/γ).Lipo2000 consumptions are 2.5 times of (2.5*0.075L=of transfected plasmids quality
0.1875μL/well).Plasmid and lipo2000 are respectively mixed in 25 μ L/well optim medium in advance.After transfection 12 hours
Plus (PPAR γ positive drug is Rosiglitazone to positive drug, and concentration is 1 μM, and PPAR α positive drug is WY14643, and concentration is 10 μ
M), and the gained of embodiment 1 MGDG.After dosing 24 hours, detection Luciferase activity.As a result show, MGDG is at 100 μM
Under concentration, PPAR α and PPAR γ (P ＜ 0.001) extremely can be significantly activated, activation multiple is respectively 1.89 ± 0.05 and 1.87 ±
0.05, it is strong PPAR alpha/gamma double agonists.
Embodiment 3：Activations of the MD1~MD6 to PPAR α and PPAR γ
Using Relative luciferase activity assay technology for detection PPAR α and PPAR γ transcriptional activation, specific side
Method be the same as Example 2.Added medicine is MD1~MD6 prepared by embodiment 1.It the results are shown in Table 2.
Activations of 2 MD1 of the table~MD6 to PPAR α/γ
Note：Compared with blank group, " * " P ＜ 0.05；" * * " P ＜ 0.01；" * * * " P ＜ 0.001.
As a result show, activation PPAR α and/or the PPAR γ that above compound can be different degrees of.Particularly, MD5 (formulas
(II) compound) show the double agonisms of significant PPAR α/γ.
The foregoing is only a specific embodiment of the invention, but protection scope of the present invention is not limited thereto, any
The change or replacement expected without creative work, should all be included within the scope of the present invention.Therefore, it is of the invention
Protection domain should be determined by the scope of protection defined in the claims.
Claims (9)
1. one kind have as shown in formula (I) structure single galactosyl diacylglycerol ester be used for prepare PPAR alfa agonists or
The purposes of PPAR alpha/gamma double agonists：
Wherein：R1And R2Acyl moieties are represented, the acyl moieties are the straight or branched aliphatic acid containing 1-30 carbon atom；
And containing 0-15 cis or trans double bond in acyl moieties.
2. purposes as claimed in claim 1, it is characterised in that the acyl moieties of formula (I) compound are former containing 6-24 carbon
The straight chain fatty acid of son, and containing 1-6 cis-double bonds in acyl moieties.
3. purposes as claimed in claim 1, it is characterised in that the acyl group of formula (I) compound is that fragment is containing 16-20
The straight chain fatty acid of carbon atom, and containing 1-5 cis-double bonds in acyl moieties.
4. purposes as claimed in claim 1, it is characterised in that formula (I) compound has a structure as shown in formula (II)：
5. single galactosyl diacylglycerol ester of structure is preparing prevention and/or treatment PPAR as shown in claim 1 formula (I)
Purposes in the medicine of alpha associated disorders.
6. single galactosyl diacylglycerol ester of structure is preparing prevention and/or treatment PPAR as shown in claim 1 formula (I)
Purposes in the medicine of α/γ relevant diseases.
7. a kind of pharmaceutical composition, it is characterised in that single galactosyl diacyl containing the structure as shown in formula (I) or formula (II)
Glyceride is used as PPAR alfa agonists or PPAR α/γ dual agonists, and pharmaceutically acceptable carrier.
8. pharmaceutical composition as claimed in claim 7, it is characterised in that described pharmaceutical composition contains 1-99.9wt%'s
With the compound as shown in formula (I) or formula (II).
9. a kind of preparation method of single galactosyl diacylglycerol ester of structure as shown in formula (I), it is characterised in that including such as
Lower step：
1) using marine alga as raw material, with the aqueous alcohol solutions refluxing extraction 2~5 times of 5-15 times of volume, merge extract solution, be concentrated into nothing
Alcohol taste, organic solvent extraction, is concentrated to give crude extract；
2) crude extract is purified by silica gel column chromatography repeatedly, Sephadex LH-20 gel filtration chromatographies, obtains single galactosyl two
The mixture of acylglycerol esters compound；Separated again through high pressure liquid chromatography, obtain single gala of multiple structures as shown in formula (I)
Glycosyl diacylglycerol ester compounds.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004359637A (en) * | 2003-06-06 | 2004-12-24 | Spirulina Biological Lab Ltd | Glyceroglycolipid compound and lipase activity inhibitor containing the same |
| CN1606563A (en) * | 2001-11-21 | 2005-04-13 | 丹麦农业科学学院 | Use of glycosides of mono- and diacylglycerol as anti-inflammatory agents |
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2017
- 2017-04-25 CN CN201710279114.8A patent/CN106983763B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1606563A (en) * | 2001-11-21 | 2005-04-13 | 丹麦农业科学学院 | Use of glycosides of mono- and diacylglycerol as anti-inflammatory agents |
| JP2004359637A (en) * | 2003-06-06 | 2004-12-24 | Spirulina Biological Lab Ltd | Glyceroglycolipid compound and lipase activity inhibitor containing the same |
Non-Patent Citations (6)
| Title |
|---|
| ARJUN H.BANSKOTA等: "Pancreatic lipase inhibitory activity of monogalactosyldiacylglycerols isolated from the freshwater microalga Chlorella sorokiniana", 《JOURNAL OF APPLIED PHYCOLOGY》 * |
| BUI THI THUY LUYEN等: "Chemical constituents of Triticum aestivum and their effects on adipogenic differentiation of 3T3-L1 preadipocytes", 《ARCH. PHARM. RES.》 * |
| HARRY MARTIN等: "A PPARγ ligand present in Actinidia fruit (Actinidia chrysantha) is identified as dilinolenoyl galactosyl glycerol", 《BIOSCI. REP.》 * |
| JOSHUA KELLOGG等: "Alaskan seaweeds lower inflammation in RAW 264.7 macrophages and decrease lipid accumulation in 3T3-L1 adipocytes", 《JOURNAL OF FUNCTIONAL FOODS》 * |
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