CN1513828A - P-benzoquinone compound and its preparation method and use - Google Patents
P-benzoquinone compound and its preparation method and use Download PDFInfo
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- CN1513828A CN1513828A CNA021601534A CN02160153A CN1513828A CN 1513828 A CN1513828 A CN 1513828A CN A021601534 A CNA021601534 A CN A021601534A CN 02160153 A CN02160153 A CN 02160153A CN 1513828 A CN1513828 A CN 1513828A
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- China
- Prior art keywords
- chain hydrocarbon
- benzoquinone compound
- under reduced
- extraction
- reduced pressure
- Prior art date
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Abstract
A p-phenylquinone compound which is a novel protein tyrosine phosphatase (PTP1B) inhibitor for treating B-type diabetes and obesity, and its preparing process are disclosed.
Description
Technical field
The present invention relates to from plant, extract the compound of biologically active, more specifically refer to the right-benzoquinone compound that from the plant Japanese Ardisia Herb, extracts.
Background technology
Diabetes are a kind of metabolic diseases that are reduced to feature with insulin deficit in the body or insulin sensitivity, get the patient of this kind disease, therefore meeting uncontrollable sugar, protein and metabolism of fat of body, and its essential characteristic is long-term hyperglycemia.Present about 100,014,000 people of whole world diabetic subject according to statistics, wherein about 90% diabetic subject is a type ii diabetes, the prevailing disease generaI investigation confirms that type ii diabetes is one of modal chronic disease in the world.To pathogenetic the discovering of type ii diabetes is a kind of proteohormone, its a series of effects all at first be with cytolemma on receptors bind and cause intracellular a series of variation by the second messenger.
And to the more further investigation of the signal transduction pathway of insulin action behind its acceptor, disclosed some and sought the novel targets of grain urine disease medicines; Up-to-date some protein tyrosine-phosphatase (the Protein Tyrsoine Phosphatase) PTPase that studies show that plays important down regulation in the signal pathway of insulin action, wherein the effect of PTP1B is especially obvious, and PTP1B is the novel targets that up-to-date of developing is used to screen treatment diabetes and obesity drug.This enzyme in vivo with external can both with the insulin receptor combination of direct phosphorylation, make it that phosphorylation take place, thereby regulating the effect of Regular Insulin in vivo, the mouse of PTP1B disappearance has confirmed this viewpoint (Science, 1999, vol283,1544-1548), thereby explanation PTP1B is treatment type ii diabetes and the good action target spot of obesity.
The inhibitor of present known PTP1B all obtains by general sieve from chemosynthesis, or lead compound obtains through the structural modification screening, still belong to the first time and from natural phant, obtain the PTP1B inhibitor, obtain little, the active strong compound of toxicity through structural modification with prestige again through separating the effective PTP1B inhibitor of acquisition through separation.
Regular Insulin is in relative deficiency state in the type ii diabetes patient body, needn't rely on insulinize fully.In the diabetic subject, type ii diabetes has accounted for great majority.Diabetes are second in modern diseases " killer ", and its harm to human body is only second to cancer, have become a kind of disease of serious threat human health.
Summary of the invention
The object of the invention provides a class to extract the biologically active compound from plant, more particularly is meant to extract right-benzoquinone compound from the plant Japanese Ardisia Herb.
Another purpose of the present invention is to extract the method for right-benzoquinone compound.
A further object of the present invention is the purposes of such right-quinone compounds.
Of the present invention right-quinone compounds structure or its equilibrium isomer be
R
1, R
2Be hydrogen, chain hydrocarbon or ring chain hydrocarbon; R
3, R
4Be hydrogen, chain hydrocarbon or ring chain hydrocarbon or aryl substituent or substituted indolyl and physiologically acceptable salt thereof, hydrate.
The present invention implements as follows:
The present invention obtains four kinds of different compounds by the extraction separation to the natural phant Japanese Ardisia Herb.
Japanese Ardisia Herb herb is fully pulverized, with 95% extraction using alcohol for several times, and united extraction liquid, concentrating under reduced pressure is removed ethanol, adds the water suspendible, with the chlorine extraction of walking back and forth, chloroform extract distributes with 90% methyl alcohol and sherwood oil, the ligroin extraction that obtains, last polyamide column is with the ethanol elution of different ratios, get the different concentration ethanol elutriant respectively, with 80% ethanol elution stream part concentrating under reduced pressure, extract separates with TSK HW-40 column chromatography chromatogram through silica gel Shephadex, gets compd A respectively
1, A
3, A
4Through NMR, IR, its structure of MS analytical proof be:
A
1 R
1＝OCH
3， R
2＝H，R
3＝(CH
2)
9CH＝CH(CH
2)
3CH
3， R
4＝OH
A
3 R
1＝OCH
2CH
3， R
2＝H，R
3＝(CH
2)
7CH＝CH(CH
2)
3CH
3， R
4＝OH
A
4R
1=OCH
2CH
3, R
2=H, R
3=(CH
2)
9CH=CH (CH
2)
3CH
3, R
4=OH70% ethanol elution flow point concentrating under reduced pressure, silicagel column Shephadex LH-20 column chromatography is separated on the oily matter, and repurity gets compd A 2, is A2 through NMR, IR, its structure of MS analytical proof
A
2 R
1＝OH，R
2＝H，R
3＝(CH
2)
9CH＝CH(CH
2)
3CH
3，R
4＝OH
Such right-quinone compounds wherein A1, A2, A3, A4 carries out external protein-tyrosine-phosphatase and suppresses to experimental results show that they have very strong inhibition activity that its result is as follows:
A
1?IC
50＝4.56μM， A
2?IC
50＝19.15μM，
A
3?IC
50＝3.01μM， A
4?IC
50＝15.55μM，
Beneficial effect of the present invention
1, the invention provides the novel targets that PTP1B is screening treatment diabetes and obesity drug.
2, utilization of the present invention obtains a class new compound in chemical extraction, separation from natural phant, and this compound is the PTP1B inhibitor.
3, available of the present invention right-benzoquinone compound modifies to hope more active compound produce it as lead compound.
Embodiment
Below by specific embodiment the present invention is further described
Get Japanese Ardisia Herb herb 2kg, pulverize the back and extract 3 times with 95% ethanol cold soaking, extracting solution merges, and being evaporated to does not have the alcohol flavor, adds the water suspendible, uses chloroform extraction.Chloroform extract distributes with 90% methyl alcohol and sherwood oil again, and polyamide column is with 70%, 80%, 90% and 95% ethanol elution on the petroleum ether part that obtains.80% ethanol elution stream part is separated through silica gel, Shephadex LH-20 and TSK LW-40 column chromatography chromatogram again, and purifying obtains compd A
1, A
3, A
4Separate through silica gel Shephadex LH-20 column chromatography at 70% wash-out position, and purifying gets compd A
2
Claims (3)
1, the following right-benzoquinone compound of a class formation
R wherein
1, R
2Be hydrogen, chain hydrocarbon or ring chain hydrocarbon;
R
3, R
4Be hydrogen, chain hydrocarbon or ring chain hydrocarbon or aryl substituent or substituted indolyl and physiologically acceptable salt thereof or hydrate.
2, a class as claimed in claim 1 right-preparation method of benzoquinone compound, it is characterized in that, extraction using alcohol broken by plant Japanese Ardisia Herb grass meal, extracting solution concentrating under reduced pressure, enriched material add the water suspendible, distribute with 90% methyl alcohol and sherwood oil with chloroform extraction, chloroform extract, obtain ligroin extraction, polyamide column on this extract, ethanol elution with different ratios, get the elutriant of different concns respectively, get stream part concentrating under reduced pressure of 80% ethanol eluate, concentrated solution through silica gel Shephadex with TSK HW-40 column chromatography, separate, respectively compd A
1, A
3, A
4Silicagel column Shephadex separates on the 70% ethanol elution stream part concentrating under reduced pressure oily matter, and repurity gets A
2
3, a class as claimed in claim 1 right-benzoquinone compound, it is characterized in that it has inhibition
The activity of PTP1B is used in treatment diabetes or obesity drug.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA021601534A CN1513828A (en) | 2002-12-31 | 2002-12-31 | P-benzoquinone compound and its preparation method and use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA021601534A CN1513828A (en) | 2002-12-31 | 2002-12-31 | P-benzoquinone compound and its preparation method and use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1513828A true CN1513828A (en) | 2004-07-21 |
Family
ID=34237796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA021601534A Pending CN1513828A (en) | 2002-12-31 | 2002-12-31 | P-benzoquinone compound and its preparation method and use |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1513828A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008002641A3 (en) * | 2006-06-28 | 2008-05-29 | Cleveland Clinic Foundation | Protein phosphatase inhibitors |
-
2002
- 2002-12-31 CN CNA021601534A patent/CN1513828A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008002641A3 (en) * | 2006-06-28 | 2008-05-29 | Cleveland Clinic Foundation | Protein phosphatase inhibitors |
| US7939554B2 (en) | 2006-06-28 | 2011-05-10 | The Cleveland Clinic Foundation | Protein phosphatase inhibitors |
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|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |