CN106967016A - There is acetylcholinesteraseinhibition inhibition compound and separation preparation and use in hypericum perforatum secondary metabolite - Google Patents
There is acetylcholinesteraseinhibition inhibition compound and separation preparation and use in hypericum perforatum secondary metabolite Download PDFInfo
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- CN106967016A CN106967016A CN201710277708.5A CN201710277708A CN106967016A CN 106967016 A CN106967016 A CN 106967016A CN 201710277708 A CN201710277708 A CN 201710277708A CN 106967016 A CN106967016 A CN 106967016A
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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Abstract
The invention belongs to pharmaceutical technology field, there is provided the compound with acetylcholinesteraseinhibition inhibition that from hypericum perforatum secondary metabolite prepared by separation, simultaneously there is provided the method for separating and preparing and purposes of these compounds, disclose the structure of hypericum perforatum secondary metabolite phloroglucinol derivatives noval chemical compound 1-15, isolate and purify, preparation method and Structural Identification, and the evaluation to the inhibiting activity of acetylcholinesterase of compound 1-15.The present invention is that the new acetylcholinesteraseinhibitors inhibitors of exploitation and medicine resisting Alzheimer disease provide compound candidate.Had very important significance for the comprehensive development and utilization of Garcinia maingayii.
Description
Technical field
The invention belongs to pharmaceutical technology field, it is related to the method for separating and preparing and purposes of compound 1-15.Specifically related to divide
From purge process, structural identification, acetylcholinesteraseinhibition inhibition etc..
Background technology
Alzheimer disease (Alzheimer ' s disease, AD) is senile dementia, be with dementia be characterized it is big
Cerebral retrogressive degenerative disease, have a strong impact on the cognitive function of patient, memory function, social-life ability, personal lifestyle ability and
Emotion personality etc..With the rapidly growth of world's elderly population, AD number of the infecteds also increase year by year, tight as modern society
One of disease of the elderly's life is threatened again.Although the pathogenesis and symptom for AD develop various medicines at present
Thing, but be clinically used to treat the most successful medicines of AD or acetylcholinesteraseinhibitors inhibitors
(Acetylcholinesterase inhibitors, AChEIs).
Hypericum perforatum (Hypericum perforatum)：Also known as Herba Hyperici Monogyni, the entitled " St.John ' s in Europe
Wort ", is commonly called as St. john's wort, is Guttiferae Hypericum herbaceos perennial.Hypericum perforatum is among the people existing 2,400
The medicinal history in remaining year.Traditional chinese medicine thinks that its is mild-natured, pungent bitterness, with the improving eyesight that clears away heart-fire, relaxes and is given birth to through promoting blood circulation, hemostasis
The effect of flesh, detoxicating, relieving inflammation, dampness removing.At present, the preparation being made of Hypericum Perforatum P.E is in American-European a large amount of listings, main use
In treatment depression, A type and hepatitis B and AIDS etc..In recent years, constantly increase with the patient of alzheimer disease
Plus, AD has become endangers one of principal disease of human health after heart disease and cancer.But the disease therapeuticing medicine is few,
Unsatisfactory curative effect, currently researches and develops the anti-AD new drugs of single target spot and baffles repeatedly, it would be highly desirable to new control strategy.Natural products, particularly spy
The natural products of different three-dimensional structure is the important source of drug development.In recent years, increasing medicament research and development personnel starts to cause
Power is in searching structure is novel from medicinal plant and has the compound of good inhibitory activity to acetylcholinesterase.Therefore, from passing through
New natural products of the screening with inhibiting activity of acetylcholinesterase has very important significance in the leaf capsule of weeping forsythia.
The content of the invention
It is an object of the invention to provide the compound with inhibiting activity of acetylcholinesterase and its isolation and purification method and
Using.
The phloroglucinol derivatives compound of the present invention, its structural formula such as formula (1)；Its Chinese and English name such as table (1).
Table (1) is named the Chinese and English of compound 1-15 in formula (1)：
| Chinese name | English name | |
| Compound 1 | St. john's wort element A | Hyperforatin A |
| Compound 2 | 32- epimerisms St. john's wort element A | 32-epi-hyperforatin A |
| Compound 3 | St. john's wort element B | Hyperforatin B |
| Compound 4 | St. john's wort element C | Hyperforatin C |
| Compound 5 | St. john's wort element D | Hyperforatin D |
| Compound 6 | 15- epimerisms St. john's wort element D | 15-epi-hyperforatin D |
| Compound 7 | St. john's wort element E | Hyperforatin E |
| Compound 8 | 32- epimerisms St. john's wort element E | 32-epi-hyperforatin E |
| Compound 9 | St. john's wort element F | Hyperforatin F |
| Compound 10 | St. john's wort element G | Hyperforatin G |
| Compound 11 | St. john's wort element H | Hyperforatin H |
| Compound 12 | St. john's wort element I | Hyperforatin I |
| Compound 13 | 15- epimerisms St. john's wort element I | 15-epi-hyperforatin I |
| Compound 14 | St. john's wort element J | Hyperforatin J |
| Compound 15 | St. john's wort element K | Hyperforatin K |
The present inventor is carried out by the ethanol extract to medicinal plant hypericum perforatum (Hypericum perforatum)
Isolate and purify, obtain 15 noval chemical compounds.The a variety of analysis method by use of spectrum of integrated use and other means, determine that it is phloroglucin
Class compound, shown in concrete structure such as formula (1).By the inhibiting activity of acetylcholinesterase evaluation to compound 1-15, find
1-15 pair of acetylcholinesterase of compound has inhibitory action, and wherein 3,5,6,8 and 9 pairs of acetylcholinesterases of compound have well
Inhibitory action.
A further object of the present invention is to provide compound shown in formula (1) in acetylcholinesterase inhibitor thing is prepared
Application.
Brief description of the drawings
Fig. 1：The crystal structure of compound 2；
Fig. 2：The crystal structure of compound 6；
Fig. 3：The crystal structure of compound 7.
Embodiment
Embodiment 1：The preparation of compound 1-15 and Structural Identification.
(1) as shown in formula (1) compound 1-15 preparation
1. plant information
The cauline leaf of this plant is plucked from Hubei Province of People's Republic of China (PRC) Shennongjia in August, 2014, by Central China section
Skill university longbow professor is accredited as hypericum perforatum (Hypericum perforatum).It is big that plant specimen deposits in Central China science and technology
Tongji Medical Institute's pharmaceutical college's Natural Medicine Chemistry and resource assessment key lab Specimen Room are learned, sample number is HP20140826.
2. extract separation
The drying cauline leaf (105kg) of hypericum perforatum is extracted 3 times after crushing with 95% ethanol, is soaked 4-5 days at room temperature every time,
Total medicinal extract 8.3kg is obtained after being concentrated under reduced pressure.Total medicinal extract is suspended in water, extracted with dichloromethane, dichloromethane is finally given
Position 3.8kg.Dichloromethane position carries out silica gel column chromatography (100-200 mesh), petroleum ether：Acetone gradient elution (100:0–0:
100), with the similar part of TLC combining data detections, 7 components (I-VII) are obtained.Component III is after the decolouring of MCI posts, except discoloration
Element, then by anti-phase C18Column chromatography (methanol-water, 50% -100%) obtains 8 components：Component III 1-III 8.
Component III 5 therein carries out silica gel column chromatography, petroleum ether again：Acetone gradient elution (30:0–0:1) it is, final to obtain
To 11 components：Ⅲ5a–Ⅲ5k.III 5d therein is purified by gel filtration chromatography and RPLC (HPLC)
Compound 10 has been arrived, and compound 5 and 6 has been obtained by Chiral HPLC Method.Meanwhile, we apply side same as described above
Method isolated compound 7 and 8 from another component III 5f.Afterwards, we have been carried out further to the 5g of component III
Reversed phase column chromatography (methanol-water, 50% -85%) simultaneously obtains 5 components：Ⅲ5g1–Ⅲ5g5.Then, we prepare by half
HPLC methods isolated compound 1 and 2 from III 5g3, the isolated compound 12 and 13 from III 5g4.
And component III 6 passes through silica gel column chromatography, petroleum ether：Ethyl acetate gradient (30:0–0:1) 8 groups, are obtained
Point：Ⅲ6a–Ⅲ6h.The 6d of component III therein has obtained compound 3,4 using column chromatography separation method identical with above-mentioned III 5g,
14, and 15.And compound 9 and 11 are to pass through reversed phase column chromatography (methanol-water, 60% -90%) by another component III 6c
And half to prepare HPLC isolated.
(2) as shown in formula (1) compound 1-15 Structural Identification
To the high resolution mass spectrum of compound 1-15, ultraviolet spectra, infrared spectrum, optically-active, nuclear magnetic resonance, circular dichroism spectra and X
The data such as ray single crystal diffraction carry out comprehensive analysis, so that it is determined that the structure of compound 1-15.
Compound 1：Colorless oil；[α]26 D+80(c 1.6,CH3OH)；UV(CH3OH)λmax(log ε)=203
(4.10)and 281(4.04)nm；ECD(CH3OH)λmax(Δε)205(-7.45),276(+30.04),305(-13.11)nm；
IR(KBr)vmax3440,2973,2929,1722,1643,1616,1446,1383,1236cm–1；HRESIMS:m/z
569.3860[M+H]+(calcd for C35H53O6, 569.3842) nuclear magnetic resonance (NMR) data such as tables (2) of compounds 1 and
Shown in table (4).
Compound 2：Colorless crystals；mp 163–165℃；[α]19 D+81(c 1.2,CH3OH)；UV
(CH3OH)λmax(log ε)=202 (4.20) and 281 (4.06) nm；ECD(CH3OH)λmax(Δε)203(-7.31),277(+
28.95),305(-12.23)nm；IR(KBr)vmax 3445,2976,2925,1725,1662,1620,1454,1383,
1236cm–1；HRESIMS:m/z 569.3851[M+H]+(calcd for C35H53O6, 569.3842) and the nuclear-magnetisms of compounds 2 is total to
Shown in (NMR) data of shaking such as table (2) and table (4), crystal structure is as schemed shown in (1).
Compound 3：Colorless oil；[α]29 D+85(c 2.5,CH3OH)；UV(CH3OH)λmax(log ε)=202
(4.23)and 273(3.97)nm；ECD(CH3OH)λmax(Δε)207(-8.84),269(+29.05),299(-7.95)nm；
IR(KBr)vmax 3437,2974,2929,1724,1642,1616,1446,1384,1226cm–1；HRESIMS:m/z
569.3846[M+H]+(calcd for C35H53O6, 569.3842) nuclear magnetic resonance (NMR) data such as tables (2) of compounds 3 and
Shown in table (4).
Compound 4：Colorless oil；[α]30 D+16(c 2.4,CH3OH)；UV(CH3OH)λmax(log ε)=203
(4.54)and 272(4.29)nm；ECD(CH3OH)λmax(Δε)205(-9.69),269(+24.88),299(-11.44)nm；
IR(KBr)vmax3434,2974,2929,1725,1648,1616,1445,1384,1234cm–1；HRESIMS:m/z
569.3838[M+H]+(calcd for C35H53O6, 569.3842) nuclear magnetic resonance (NMR) data such as tables (2) of compounds 4 and
Shown in table (4).
Compound 5：Colorless oil；[α]26 D+12(c 0.5,CH3OH)；UV(CH3OH)λmax(log ε)=202
(4.41)and 280(4.21)nm；ECD(CH3OH)λmax(Δε)207(-6.24),275(+17.08),304(-10.51)nm；
IR(KBr)vmax3437,2975,2930,1722,1656,1621,1445,1383,1243cm–1；HRESIMS:m/z
605.3828[M+Na]+(calcd for C36H54O6Na, 605.3818) compounds 5 nuclear magnetic resonance (NMR) data such as table
(2) and shown in table (4).
Compound 6：Colorless crystals；mp 108–110℃；[α]26 D+54(c 0.6,CH3OH)；UV
(CH3OH)λmax(log ε)=202 (4.31) and 280 (4.29) nm；ECD(CH3OH)λmax(Δε)205(-11.40),276(+
34.12),305(-14.21)nm；IR(KBr)vmax 3442,2975,2929,1724,1655,1620,1446,1382,
1238cm–1；HRESIMS:m/z 583.3992[M+H]+(calcd for C36H55O6, 583.3999) and the nuclear-magnetisms of compounds 6 is total to
Shown in (NMR) data of shaking such as table (2) and table (5), crystal structure is as schemed shown in (2).
Compound 7：Colorless crystals；mp 108–109℃；[α]26 D+66(c 0.3,CH3OH)；UV
(CH3OH)λmax(log ε)=203 (4.42) and 273 (4.29) nm；ECD(CH3OH)λmax(Δε)227(+12.73),248(-
4.16),273(+13.80),302(-4.92)nm；IR(KBr)vmax 3437,2970,2926,1731,1626,1449,1377,
1237,1212cm–1；HRESIMS:m/z 569.3857[M+H]+(calcd for C35H53O6,569.3842).Compound 7
Shown in nuclear magnetic resonance (NMR) data such as table (2) and table (5), crystal structure is as schemed shown in (3).
Compound 8：Colorless oil；[α]26 D+71(c 0.8,CH3OH)；UV(CH3OH)λmax(log ε)=202
(4.27)and 273(4.20)nm；ECD(CH3OH)λmax(Δε)227(+13.92),248(-4.30),273(+14.36),
302(-4.76)nm；IR(KBr)vmax 3438,2973,2927,1730,1627,1451,1365,1237,1212cm–1；
HRESIMS:m/z 569.3836[M+H]+(calcd for C35H53O6, 569.3842) and the nuclear magnetic resonance (NMR) of compounds 8
Shown in data such as table (2) and table (5)
Compound 9：Colorless oil；[α]22 D+52(c 0.4,CH3OH)；UV(CH3OH)λmax(log ε)=202
(4.20)and 273(4.01)nm；ECD(CH3OH)λmax(Δε)225(+7.40),247(-1.90),271(+9.70),301
(-2.86)nm；IR(KBr)vmax 3449,2971,2925,1730,1622,1451,1366,1237,1209cm–1；HRESIMS:
m/z 525.3547[M+H]+(calcd for C33H49O5, 525.3580) and nuclear magnetic resonance (NMR) the data such as tables of compounds 9
(3) and shown in table (5)
Compound 10：Colorless oil；[α]29 D+48(c 0.6,CH3OH)；UV(CH3OH)λmax(log ε)=202
(4.05)and273(3.93)nm；ECD(CH3OH)λmax(Δε)227(+6.47),248(-2.63),273(+7.23),302(-
2.60)nm；IR(KBr)vmax 3441,2972,2927,1731,1624,1452,1366,1237,1213cm–1；HRESIMS:m/
z 569.3866[M+H]+(calcd for C35H53O6,569.3842)。
Shown in nuclear magnetic resonance (NMR) data such as table (3) and table (5) of compound 10.
Compound 11：Colorless oil；[α]28 D+34(c 0.5,CH3OH)；UV(CH3OH)λmax(log ε)=202
(4.10)and 283(4.00)nm；ECD(CH3OH)λmax(Δε)242(-5.64),276(+15.73),302(-12.03)nm；
IR(KBr)vmax 3442,2972,2929,1729,1623,1408,1384,1236,1182cm–1；HRESIMS:m/z
569.3851[M+H]+(calcd for C35H53O6, 569.3842) and nuclear magnetic resonance (NMR) data such as tables (3) of compounds 11
With table (6) Suo Shi
Compound 12：Colorless oil；[α]21 D+23(c 0.4,CH3OH)；UV(CH3OH)λmax(log ε)=202
(4.12)and 282(3.93)nm；ECD(CH3OH)λmax(Δε)243(-4.16),277(+13.37),302(-9.97)nm；
IR(KBr)vmax 3434,2972,2927,1727,1614,1447,1409,1382,1236cm–1；HRESIMS:m/z
591.3660[M+Na]+(calcd for C35H52O6Na, 591.3662) compounds 12 nuclear magnetic resonance (NMR) data such as table
(3) and shown in table (6)
Compound 13：Colorless oil；[α]21 D-28(c 0.3,CH3OH)；UV(CH3OH)λmax(log ε)=202
(4.20)and 282(4.03)nm；ECD(CH3OH)λmax(Δε)244(-4.79),276(+10.41),301(-10.55)nm；
IR(KBr)vmax 3435,2960,2925,1726,1617,1451,1408,1382,1230cm–1；HRESIMS:m/z
591.3657[M+Na]+(calcd for C35H52O6Na, 591.3662) compounds 13 nuclear magnetic resonance (NMR) data such as table
(3) and shown in table (6)
Compound 14：Colorless oil；[α]28 D+42(c 4.3,CH3OH)；UV(CH3OH)λmax(log ε)=202
(4.49)and 272(4.30)nm；ECD(CH3OH)λmax(Δε)242(-4.07),269(+12.90),294(-6.81)nm；
IR(KBr)vmax 3435,2972,2928,1730,1621,1446,1411,1383,1214cm–1；HRESIMS:m/z
569.3860[M+H]+(calcd for C35H53O6, 569.3842) and nuclear magnetic resonance (NMR) data such as tables (3) of compounds 14
With table (6) Suo Shi
Compound 15：Colorless oil；[α]28 D-10(c 2.4,CH3OH)；UV(CH3OH)λmax(log ε)=202
(4.35)and 273(3.97)nm；ECD(CH3OH)λmax(Δε)243(-3.74),270(+8.89),296(-5.05)nm；IR
(KBr)vmax 3435,2973,2928,1728,1620,1446,1412,1384,1215cm–1；HRESIMS:m/z 569.3832
[M+H]+(calcd for C35H53O6, 569.3842) and nuclear magnetic resonance (NMR) data such as tables (3) of compounds 15 and table (6) institute
Show
Table (2) compounds 1-813C NMR datas (Record in CD3OD).
Table (3) compounds 9-1513C NMR datas (Record in CD3OD).
Table (4) compounds 1-51H NMR datas (Record in CD3OD；J in Hz).
Table (5) compounds 6-101H NMR datas (Record in CD3OD；J in Hz).
Table (6) compounds 11-151H NMR datas (Record in CD3OD；J in Hz).
Embodiment 2：The inhibitory action of 1-15 pair of acetylcholinesterase of compound.
The inhibitory action of 1-15 pair of acetylcholinesterase of compound is determined by Ellman methods, as a result such as table (7)
It is shown.
The inhibitory action of 1-15 pair of acetylcholinesterase of table (7) compounds
Experiment conclusion：1-15 pair of acetylcholinesterase of compound has inhibitory action.Wherein, compound 3,5,6,8,9 pairs
Acetylcholinesterase has an obvious inhibitory action, compound Isosorbide-5-Nitrae, and 11,15 have preferable inhibiting activity of acetylcholinesterase.
Claims (6)
1. the phloroglucinol derivatives compound 1-15 with structure shown in formula (1),
2. the preparation method of the phloroglucinol derivatives compound described in claim 1, it is characterised in that described phloroglucinol derivatives
Compound 1 to 15 is to isolate and purify to obtain from hypericum perforatum.
3. preparation method according to claim 2, it is characterised in that isolated and purified from hypericum perforatum and obtain claim
The specific method of phloroglucinol derivatives compound described in 1, comprises the following steps：
S1. dry hypericum perforatum cauline leaf, with 95% ethanol extraction 3 times in multi-function extractor after crushing, every time at room temperature
Immersion 4-5 days, obtains total medicinal extract after being concentrated under reduced pressure；
S2. total medicinal extract resulting in S1 is suspended in water, is extracted with dichloromethane, solvent is recovered under reduced pressure, finally give two
The total extract at chloromethanes position；
S3. dichloromethane total extract dichloromethane position resulting in S2 is subjected to silica gel column chromatography (100-200 mesh), oil
Ether：Acetone gradient elution (100:0–0:100), with the similar part of TLC combining data detections, 7 components (I-VII) are obtained.Component III
After the decolouring of MCI posts, except depigmentaton, then by anti-phase C18Column chromatography (methanol-water, 50% -100%) obtains 8 components：Group
Divide III 1-III 8；Component III 5 therein carries out silica gel column chromatography, petroleum ether again：Acetone gradient elution (30:0–0:1), finally
Obtain 11 components：Ⅲ5a–Ⅲ5k；III 5d therein is purified by gel filtration chromatography and RPLC (HPLC)
Compound 10 has been obtained, and compound 5 and 6 has been obtained by Chiral HPLC Method；Meanwhile, using method same as described above
The isolated compound 7 and 8 from another component III 5f；Afterwards, further reversed-phase column has been carried out to the 5g of component III
Chromatography (methanol-water, 50% -85%) simultaneously obtains 5 components：Ⅲ5g1–Ⅲ5g5；Then, HPLC methods are prepared from III by half
Isolated compound 1 and 2 in 5g3, the isolated compound 12 and 13 from III 5g4；And component III 6 passes through silica gel column layer
Analysis, petroleum ether：Ethyl acetate gradient (30:0–0:1) 8 components, are obtained：Ⅲ6a–Ⅲ6h；The 6d of component III applications therein
Column chromatography separation method identical with above-mentioned III 5g has obtained compound 3,4,14, and 15；And compound 9 and 11 are by another
It is isolated that the individual 6c of component III prepares HPLC by reversed phase column chromatography (methanol-water, 60% -90%) and half.
4. application of any of the compound 1-15 in acetylcholinesterase inhibitor thing is prepared described in claim 1.
5. application of the compound 3,5,6,8 or 9 described in claim 1 in acetylcholinesterase inhibitor thing is prepared.
6. any of compound 1-15 described in claim 1 is preparing the application in being used to treat alzheimer medicine.
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Cited By (2)
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| CN110551139A (en) * | 2018-05-31 | 2019-12-10 | 华中科技大学 | Compound with anti-Alzheimer disease activity and preparation method and application thereof |
| CN111718359A (en) * | 2019-03-23 | 2020-09-29 | 中国医学科学院药物研究所 | Hyperterpnoid A compound and application thereof in neuroprotection |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110551139A (en) * | 2018-05-31 | 2019-12-10 | 华中科技大学 | Compound with anti-Alzheimer disease activity and preparation method and application thereof |
| CN110551139B (en) * | 2018-05-31 | 2020-08-04 | 华中科技大学 | Compound with anti-Alzheimer disease activity and preparation method and application thereof |
| CN111718359A (en) * | 2019-03-23 | 2020-09-29 | 中国医学科学院药物研究所 | Hyperterpnoid A compound and application thereof in neuroprotection |
| CN111718359B (en) * | 2019-03-23 | 2022-07-19 | 中国医学科学院药物研究所 | Hyperterpnoid A compound and application thereof in neuroprotection |
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