CN106995475B - The preparation method and purposes of single galactosyl monoacylglycerol ester - Google Patents
The preparation method and purposes of single galactosyl monoacylglycerol ester Download PDFInfo
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- CN106995475B CN106995475B CN201710279123.7A CN201710279123A CN106995475B CN 106995475 B CN106995475 B CN 106995475B CN 201710279123 A CN201710279123 A CN 201710279123A CN 106995475 B CN106995475 B CN 106995475B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- C07H15/06—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical being a hydroxyalkyl group esterified by a fatty acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
Abstract
The invention discloses a kind of preparation method of single galactosyl monoacylglycerol ester with the structure as shown in formula (I) and it is used to prepare PPARαAgonist or PPARγAgonist and PPARα/γThe purposes of double agonists.(I) wherein: R1And R2Acyl moieties are represented, the acyl moieties are the linear chain or branched chain fatty acid containing 1-30 carbon atom；And contain 0-15 cis or trans double bond in acyl moieties.Present invention finds single galactosyl monoacylglycerol esters to PPARα、PPARγAgonism and PPARα/γDouble excitations effect, disclose such compound prevention and treatment PPARs related disease in application value.In addition, present invention discover that and separated the active constituent that seaweed is beneficial to cardiovascular health, provide effective substance and function factor for exploitation seaweed drug, health food, food.
Description
Technical field
The present invention relates to the preparation methods and purposes of a kind of single galactosyl monoacylglycerol ester, specifically, being related to one
It plants the preparation method of single galactosyl monoacylglycerol ester and its is moved as PPAR α or PPAR gamma agonist and PPAR α/γ bidifly
The purposes of agent.
Background technique
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-
Kind hypotype.PPARs is first formed different dimerization with retinoid receptor X (retinoidX receptor, RXR) after ligand activation
Body, then with the Peroxisome proliferators responsive element of target gene promoters upstream (peroxisome proliferator
Response element, PPRE) it combines, lipid-metabolism is regulated and controled by the transcriptional regulatory of target gene, fat generates, insulin
The important biochemical reaction processes 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, important target spot of the PPARs as mankind's metabolism related diseases protective agents, has been a concern.
Binding site, that is, ligand binding domain (LBD) of compound and PPAR is the active region of ligand-dependent, X-ray monocrystalline
Diffraction confirms that the LBD of 3 kinds of PPAR possesses similar three-dimensional structure, but the internal structure of ligand binding pocket is different.PPAR β's
Binding pocket there are the place of an obvious stenosis, this prevent the ligand of many relatively large PPAR α and PPAR γ from
PPAR β is combined.In PPAR α and PPAR γ, after ligand is in conjunction with LBD, mutual configuration can change, the acid head of ligand
Hydrogen bond is formed between certain specific amino acid residues on portion's group (c-terminus of such as fatty acid) and LBD, this hydrogen bond is exactly
The switch of PPAR receptor activation.Therefore, in compound contain carboxyl or similar structures (carbonyl or ester group), be likely to
LBD forms hydrogen bond, to activate PPARs.Since position and the type of the amino acid residue of hydrogen bond are formed in LBD with ligand binding
Not identical, therefore, different compounds may only activate a kind of PPAR receptor, it is also possible to while activating two kinds of PPAR receptors.Institute
With again the agonist of PPAR has single agonist, point of double agonists.
PPAR alfa agonists can promote lipid metabolism, increase the synthesis of high-density lipoprotein.Gemfibrozil, fenofibrate,
The drugs such as Clofibrate are PPAR alfa agonists, clinically for treating dyslipidemia, have preferable effect for reducing fat.PPAR α by
Body agonist can also inhibit various transcription factors, inflammatory mediator and adhesion molecule, alleviate albuminuria, prevent glomerulus loose, right
It is effective to treat obesity, hypertension, atherosclerosis, nonalcoholic fatty liver and diabetic nephropathy.
PPAR gamma agonist improves insulin sensitivity by promoting fatty acid storage and inhibiting Fatty synthesis.Thiophene
Oxazolidinedione class (TZD) drug such as Pioglitazone, Rosiglitazone etc. are all PPAR gamma agonists, are clinically used as insulin sensitivity enhancing
Agent is used for the treatment of diabetes B.But PPAR gamma agonist also promotes glucose to transport to adipose tissue simultaneously, this may
It will lead to patient's weight increase.
Currently, can the discovery of PPAR alpha/gamma double agonists of hypoglycemic but also lipid-loweringing have become hot spot.PPAR alfa agonists energy
Animal ingestion and fat deposition, the oxidative metabolism for promoting Liver lipids are reduced, to mitigate weight caused by PPAR gamma agonist
Increase side effect.Studies have shown that PPAR α/γ dual agonists can not only reduce triacylglycerol and increasing high density lipoprotein, In
Treatment is fat and improvement cardiovascular disease 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 effect to nonalcoholic fatty liver and diabetic nephropathy.With single PPAR gamma agonist
It compares, PPAR α/γ dual agonists have better safety.
Single galactosyl monoacylglycerol ester (monogalactosylmonoacylglycerol, MGMG) is glyceroglycolipid
(glyceroglycolipid) one kind has antibacterial, antitumor, anti-inflammatory, anti-platelet aggregation, inhibition accumulation of lipid etc. living
Property.According to the position of substitution of acyl group on the glycerol backbone, MGMG has two kinds of position isomers of sn-1 type and sn-2 type.Currently, not
See document report of the MGMG as the dual agonists purposes of PPAR α or PPAR gamma agonist, especially PPAR α/γ.
Summary of the invention
In view of the above-mentioned problems, the first purpose of the invention is to provide a kind of single galactosyl monoacylglycerol ester compounds
Purposes as the mono- agonist of PPAR α or PPAR γ and PPAR alpha/gamma double agonists.
It is a further object to provide the preparation methods of above-mentioned single galactosyl monoacylglycerol ester.
Single galactosyl monoacylglycerol ester with the structure as shown in formula (I) is used to prepare PPAR α, PPAR gamma agonist
Or the purposes of PPAR alpha/gamma double agonists.
Wherein: R1And R2Acyl moieties are represented, the acyl moieties are the linear chain or branched chain fat containing 1-30 carbon atom
Acid；And contain 0-15 cis or trans double bond in acyl moieties.
Further, with the structure as shown in formula (I) single galactosyl monoacylglycerol ester preparation for improve with
PPAR alpha associated disorders, such as dyslipidemia, obesity, hypertension, atherosclerosis, nonalcoholic fatty liver, diabetic nephropathy
Purposes in drug.
Further, with the structure as shown in formula (I) single galactosyl monoacylglycerol ester preparation for improve with
PPAR γ related disease, such as diabetes B, hypertension, atherosclerosis, myocardial hypertrophy, ischemical reperfusion injury, itself exempts from
Purposes in epidemic disease myocarditis drug.
Further, single galactosyl monoacylglycerol ester with the structure as shown in formula (I) is as PPAR α/γ bidifly
PPARs related disease is treated in dynamic agent, and such as diabetes B is fat, dyslipidemia, hypertension, atherosclerosis, non-alcoholic
Fatty liver, diabetic nephropathy, myocardial hypertrophy, ischemical reperfusion injury, the purposes in the drug of autoimmune myocarditis.
Preferably, 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 1-4 in acyl moieties
A cis-double bonds.
One of most preferred embodiment, formula (I) compound have the structure as shown in formula (II), be used to prepare PPAR α,
The purposes of PPAR gamma agonist or PPAR alpha/gamma double agonists.
One of most preferred embodiment, formula (I) compound have the structure as shown in formula (III), be used to prepare PPAR α,
The purposes of PPAR gamma agonist or PPAR alpha/gamma double agonists.
Further, single galactosyl monoacylglycerol ester with the structure as shown in formula (II) or formula (III) is used in preparation
Improvement and PPAR alpha associated disorders, such as dyslipidemia, obesity, hypertension, atherosclerosis, nonalcoholic fatty liver, diabetes
Purposes in the drug of nephrosis.
Further, single galactosyl monoacylglycerol ester with the structure as shown in formula (II) or formula (III) is used in preparation
In improvement and PPAR γ related disease, such as diabetes B, hypertension, atherosclerosis, myocardial hypertrophy, ischemia-reperfusion damage
Hurt, the purposes in the drug of autoimmune myocarditis.
Further, single galactosyl monoacylglycerol ester with the structure as shown in formula (II) or formula (III) is as PPAR
Alpha/gamma double agonists treat PPARs related disease, and such as diabetes B is fat, dyslipidemia, hypertension, atherosclerosis,
Nonalcoholic fatty liver, diabetic nephropathy, myocardial hypertrophy, ischemical reperfusion injury, in the drug of autoimmune myocarditis
Purposes.
Further, the present invention provides a kind of pharmaceutical composition, contain such as formula (I), formula (II) or formula (III) institute
Show structural compounds as PPAR α, PPAR gamma agonist or PPAR alpha/gamma double 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 at
Divide and conventional excipients, flavoring agent, disintegrating agent, preservative, lubricant, wetting agent, adhesive, solvent, thickener or solubilising
Any dosage form for being suitable for clinical use is made in the mixing of the excipient substances such as agent, as pulvis, tablet, capsule, granule,
Injection, oral liquid etc..
Preferably, the pharmaceutical composition contain 1-99.9wt% have as shown in formula (I), formula (II) or formula (III)
Compound.
In addition, the present invention also provides a kind of preparation methods of single galactosyl monoacylglycerol ester comprising following step
It is rapid:
1) using seaweed as raw material, with aqueous alcohol solutions refluxing extraction 2~5 times of 5-15 times of volume, combined extract is concentrated
To no alcohol taste, organic solvent extraction is concentrated to give crude extract；
2) by crude extract by silica gel column chromatography repeatedly, the purifying of Sephadex LH-20 gel filtration chromatography obtains single galactolipin
The mixture of base monoacylglycerol ester type compound, then separated through high pressure liquid chromatography, obtain the list of multiple structures as shown in formula (I)
Galactosyl monoacylglycerol ester compounds.
Advantages of the present invention: present invention firstly discovers that single galactosyl monoacylglycerol ester swashs PPAR α, PPAR γ
Movement is used and the effect of the double excitations of PPAR α/γ, discloses application of such compound in prevention and treatment PPARs related disease
Value.In addition, present invention discover that and separated the active constituent that seaweed is beneficial to cardiovascular health, for exploitation seaweed drug, protect
Health food, food provide effective substance and function factor.
Detailed description of the invention
Fig. 1 is MGMG's1H-NMR spectrum.
Fig. 2 is MGMG's13C-NMR spectrum.
Specific embodiment
With reference to the accompanying drawing and by specific embodiment come the present invention will be described in detail.
Embodiment 1: the extraction preparation of single galactosyl monoacylglycerol 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.Combined extract, filtering,
It is concentrated into no alcohol taste, is extracted 3 times using isometric ethyl acetate, combining extraction liquid, concentration obtains medicinal extract 33.26g.Medicinal extract is through second
Acetoacetic ester dissolution mixes sample with 41g 200-300 mesh silica gel H, and silica gel column chromatography carries out gradient by solvent of methylene chloride-methanol
Elution, wherein methylene chloride-methanol (v/v 90:10) elutes obtained component, then through Sephadex LH-20 gel filtration chromatography (two
Chloromethanes-methanol 1:1) and silica gel column chromatography, the mixture of single galactosyl monoacylglycerol ester type compound (MGMG) is obtained, is surveyed
Its1H-NMR spectrum and13C-NMR composes (as illustrated in fig. 1 and 2).
According to Fig. 1's1H-NMR(500MHz,in CD3OD): 4.15 (2H, m, H-1), 3.99 (1H, m, H-2), 3.67
(1H, dd, J=4.5,10.5Hz, H-3a), 3.92 (1H, dd, J=5.1,10.5Hz, H-3b), 4.24 (1H, d, J=7.5Hz,
), H-1' 3.54 (1H, m, H-2'), 3.48 (1H, dd, J=3.1,9.8Hz, H-3'), 3.84 (1H, d, J=2.7Hz, H-4'),
3.51 (1H, m, H-5'), 3.75 (2H, m, H-6'), 2.36 (2H, dd, J=7.3,14.7Hz, COCH2),1.31[10H,m,
(CH2)n], 0.97 (2H, t, J=7.5Hz, CH3),0.90(1H,m,CH3) and Fig. 213C NMR(125MHz,CD3OD):
66.6(C-1),69.6(C-2),71.9(C-3),105.2(C-1'),72.5(H-2'),74.8(H-3'),70.3(H-4'),
76.7(H-5'),62.5(H-6'),175.5(CO),30.2-34.9[(CH2)n],14.7(CH3),14.4(CH3).It is accredited as list
The mixture of galactosyl monoacylglycerol ester (MGMG).
MGMG mixture is isolated and purified through Semi-PHPLC again, and methanol-water (v/v 84:16) perseverance gradient elution successively obtains
Compound MM1~MM7.Through HR-MS/MS (as shown in table 1), in conjunction with GC-MS data, the acyl group of identification of M M1~7 composition are as follows: 18
Four enoyl- of carbon (MM1 and 2), 18 carbon, three enoyl- (MM3 and 4), Eicosatetraenoic acyl group (MM5), 18 carbon dienoyls
(MM6), 18 carbon monoene acyl group (MM7).
1 MM1 of table~MM7 HRESI-MS/MS data
Activation of the embodiment 2:MGMG to PPAR α and PPAR γ
Utilize the transcriptional activation of Relative luciferase activity assay technology detection PPAR α and PPAR γ.By 293T
Cell inoculation is in 96 orifice plates, and DMEM trains liquid (10%FBS is free of antibiotic), and cell grows to 60% or so after 8-12 hours, no
Liquid is changed, by lipo2000 specification, 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 dosage is 2.5 times of (2.5*0.075L=of transfected plasmids quality
0.1875μL/well).Plasmid and lipo2000 are respectively mixed in advance in the optim medium of 25 μ L/well.After transfection 12 hours
Adding positive drug, (positive drug of PPAR γ is Rosiglitazone, and concentration is 1 μM, and the positive drug of PPAR α is WY14643, and concentration is 10 μ
) and the resulting MGMG of embodiment 1 M.After dosing 24 hours, detection Luciferase activity.The result shows that MGMG is at 100 μM
Under concentration, extremely can significantly it activate PPAR α and PPAR γ (P < 0.01), activation multiple is respectively 1.37 ± 0.03 and 1.11 ±
0.02, it is PPAR alpha/gamma double agonists.
Activation of the embodiment 3:MM1~MM7 to PPAR α and PPAR γ
Using the transcriptional activation of Relative luciferase activity assay technology detection PPAR α and PPAR γ, specific side
Method is the same as embodiment 2.Added drug is MM1~MM7 prepared by embodiment 1.It the results are shown in Table 2.
2 MM1 of table~MM7 is to PPAR α/γ activation
Note: " * " compared to the blank group, P < 0.05；" * * ", P < 0.01；" * * * ", P < 0.001.
The result shows that the above compound different degrees of activation PPAR α and/or the PPAR γ of energy.In particular, MM5 (formula
(II) compound) and MM6 (formula (III) compound) show the significant bis- agonisms of PPAR α/γ.
The above description is merely a specific embodiment, but scope of protection of the present invention is not limited thereto, any
The change or replacement expected without creative work, should be covered by the protection scope of the present invention.Therefore, of the invention
Protection scope should be determined by the scope of protection defined in the claims.
Claims (9)
1. there is one kind single galactosyl monoacylglycerol ester of the structure as shown in formula (I) to be used to prepare PPAR alfa agonists, PPAR
The purposes of gamma agonist or PPAR alpha/gamma double agonists:
Wherein: R1And R2Acyl moieties are represented, the acyl moieties are the linear chain or branched chain fatty acid containing 1-30 carbon atom；
And contain 1-15 cis or trans double bond in acyl moieties.
2. purposes as described 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 contain 1-6 cis-double bonds in acyl moieties.
3. purposes as described in claim 1, it is characterised in that the acyl group of formula (I) compound is that segment is containing 16-20
The straight chain fatty acid of carbon atom, and contain 1-4 cis-double bonds in acyl moieties.
4. purposes as described in claim 1, it is characterised in that formula (I) compound has the structure as shown in formula (II):
5. purposes as described in claim 1, it is characterised in that formula (I) compound has the structure as shown in formula (III):
6. single galactosyl monoacylglycerol ester of the structure as shown in claim 1 formula (I) is in preparation prevention and/or treatment PPAR
Purposes in the drug of α or PPAR γ related disease.
7. a kind of pharmaceutical composition, it is characterised in that contain formula as described in claim 1 (I), formula as claimed in claim 4
(II) or single galactosyl monoacylglycerol ester of structure shown in formula described in claim 5 (III) as PPAR alfa agonists,
PPAR gamma agonist or PPAR α/γ dual agonists and pharmaceutically acceptable carrier.
8. pharmaceutical composition as claimed in claim 7, it is characterised in that the pharmaceutical composition contains 1-99.9wt%'s
With shown in formula (III) described in formula as described in claim 1 (I), formula as claimed in claim 4 (II) or claim 5
Compound.
9. a kind of preparation method of single galactosyl monoacylglycerol ester of structure shown in formula as described in claim 1 (I),
It is characterized in that including the following steps:
1) using seaweed as raw material, with aqueous alcohol solutions refluxing extraction 2~5 times of 5-15 times of volume, combined extract is concentrated into nothing
Alcohol taste, organic solvent extraction, is concentrated to give crude extract；
2) by crude extract by silica gel column chromatography repeatedly, the purifying of Sephadex LH-20 gel filtration chromatography obtains single galactosyl list
The mixture of acylglycerol esters compound, then separated through high pressure liquid chromatography, obtain multiple formulas as described in claim 1 (I)
Single galactosyl monoacylglycerol ester compounds of shown structure.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101037458A (en) * | 2007-04-12 | 2007-09-19 | 上海水产大学 | Isolation method of natural compound with fibrinolysis accelerating function |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101037458A (en) * | 2007-04-12 | 2007-09-19 | 上海水产大学 | Isolation method of natural compound with fibrinolysis accelerating function |
Non-Patent Citations (2)
| Title |
|---|
| A PPARγ ligand present in Actinidia fruit (Actinidia chrysantha) is identified as dilinolenoyl galactosyl glycerol;H. Martin, et al.;《Biosci. Rep.》;20130402;第33卷(第3期);第387-394页 * |
| Enzymatic Transformation of Glyceroglycolipids into sn-1 and sn-2 Lysoglyceroglycolipids by Use of Rhizopus arrhizus Lipase;Nobutoshi Murakamiz,et al.;《Tetrahedron》;19941231;第50卷(第7期);第1993-2002页 * |
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