CN116284037A - New skeleton guaiane sesquiterpene in daphne neroli, and preparation method and application thereof - Google Patents

New skeleton guaiane sesquiterpene in daphne neroli, and preparation method and application thereof Download PDF

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CN116284037A
CN116284037A CN202310255151.0A CN202310255151A CN116284037A CN 116284037 A CN116284037 A CN 116284037A CN 202310255151 A CN202310255151 A CN 202310255151A CN 116284037 A CN116284037 A CN 116284037A
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daphne
neroli
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guaiane
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宋少江
黄肖霄
董舒卉
连美雅
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Shenyang Pharmaceutical University
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Abstract

A new skeleton guaiane sesquiterpene in daphne neroli, a preparation method and application thereof belong to the technical field of medicines, and in particular relates to 6 new guaiane sesquiterpene derivatives extracted and separated from daphne neroli (Daphne aurantiaca) which is a daphne plant in daphne of daphnaceae, wherein the new compounds have good neuroprotective activity and cholinesterase inhibiting activity. The preparation method is simple and easy to implement, and has better reproducibility and higher purity.
Figure DDA0004130778650000011

Description

New skeleton guaiane sesquiterpene in daphne neroli, and preparation method and application thereof
Technical Field
The invention belongs to the technical field of medicines, and particularly relates to 6 guaiane sesquiterpene derivatives prepared from daphne nervosa and application of the compounds in neuroprotective activity and cholinesterase inhibition activity.
Background
Daphne genus: daphne belongs to Daphne [ Thymelaeaceae ], has more than 90 species and is mainly distributed in Asia, europe and northern part of the world. In recent years, research shows that the plant belongs to the genus plant has abundant and various secondary metabolites and has better biological activities such as neuroprotection, cholinesterase inhibition, bacteriostasis and the like.
Orange flower daphne: orange daphne [ Daphne aurantiaca ] is a dwarf shrub of daphne, and is mainly distributed in northwest and northwest regions of Yunnan and Sichuan of China. At present, little report about the chemical components and pharmacological activity of daphne neroli is made. The compounds and the activity thereof related to the invention have not been reported in patents or documents so far.
Disclosure of Invention
The invention aims to provide 6 sesquiterpenoids and a preparation method thereof.
The invention also provides application of the sesquiterpenoids in neuroprotective activity and cholinesterase inhibitory activity.
The 6 sesquiterpenoids separated from daphne neroli [ Daphne aurantiaca ] of daphne of daphnaceae have the following structures:
Figure BDA0004130778610000011
the preparation technical scheme of the invention comprises the following steps:
extracting dried daphne neroli whole plant with ethanol, mixing the extracting solutions, concentrating to obtain an extract, extracting the extract with ethyl acetate, subjecting the obtained components to silica gel column chromatography, performing gradient elution with a dichloro-methanol system 1:0-0:1, and collecting 10 components Fr.A-J;
performing gradient elution on the component Fr.C by using HP20 and ODS column chromatography in an ethanol-water system of 20:80-100:0 to obtain 12 components Fr.C1-Fr.C12;
eluting with a petroleum ether-ethyl acetate system 100:1-1:1 by silica gel column chromatography and separating Fr.C5, fr.C6 and Fr.C7 on preparative reverse phase high performance liquid chromatography using acetonitrile-water mobile phase gives compounds 1-6.
The preparation method of the guaiane sesquiterpene derivative in the daphne neroli is characterized in that the daphne neroli is daphne neroli [ Daphne aurantiaca ] which is a daphne plant in daphne of daphnaceae.
The preparation method of the guaiane sesquiterpene derivative in the daphne neroli is characterized by taking a dried daphne neroli whole plant, and extracting the daphne neroli whole plant with 80% industrial ethanol under reflux for 3 times, each time for 2-3 hours.
The preparation method of the guaiane sesquiterpene derivative in the daphne neroli is characterized by comprising the following steps of: 30-30:70, fr.c5, fr.c6 and fr.c7 are separated by an acetonitrile-water mobile phase.
The results of the system structure identification of the obtained compound are as follows:
the structure of the compounds 1-6 is identified by high resolution mass spectrometry, one-dimensional NMR, two-dimensional NMR, nuclear magnetism calculation, ECD calculation and X single crystal diffraction method, the corresponding spectrograms are shown in figures 1-10, 1 h NMR 13 The C NMR data are shown in tables 1 and 2.
Daphaulide A (1) yellow oily;
Figure BDA0004130778610000023
HRESIMS(m/z247.13217[M+H] + calcd 247.13287) to determine the molecular formula as C 15 H 18 O 3 The method comprises the steps of carrying out a first treatment on the surface of the By analysis of daphaulide A 1 HNMR、 13 CNMR, HSQC spectra, HMBC spectra, NMR calculationsECD calculation determines the structure of daphaulide A as a new compound.
Daphaulide B (2) as pale yellow oil;
Figure BDA0004130778610000022
HRESIMS(m/z271.1296[M+Na] + calcd 271.1305) to determine the molecular formula as C 15 H 20 O 3 The method comprises the steps of carrying out a first treatment on the surface of the By analysis of daphaulide B 1 HNMR、 13 CNMR, HSQC spectrum, HMBC spectrum, NMR calculation and ECD calculation, the structure of the daphaulide B is determined, and the structure is a novel compound.
Daphaulide C (3) as pale yellow oil;
Figure BDA0004130778610000024
HRESIMS(m/z217.1198[M+Na] + calcd 217.1204) to determine the molecular formula as C 12 H 18 O 2 The method comprises the steps of carrying out a first treatment on the surface of the By analysis of daphaulide C 1 HNMR、 13 CNMR, HSQC spectrum, HMBC spectrum, NMR calculation and ECD calculation, the structure of the daphaulide C is determined, and the structure is a novel compound.
Daphaulide D (4) yellow oil;
Figure BDA0004130778610000025
HRESIMS(m/z261.10910[M+Na] + calcd 261.10973) to determine the molecular formula as C 13 H 18 O 4 The method comprises the steps of carrying out a first treatment on the surface of the By analysis of daphaulide D 1 HNMR、 13 CNMR, HSQC spectrum, HMBC spectrum, NMR calculation and ECD calculation, the structure of the daphaulide D is determined, and the structure is a novel compound.
Daphaulide (5) yellow oil;
Figure BDA0004130778610000026
HRESIMS(m/z265.14316[M+H] + calcd 265.14344) to determine the molecular formula as C 15 H 20 O 4 The method comprises the steps of carrying out a first treatment on the surface of the By analysis of daphaulide E 1 HNMR、 13 CNMR, HSQC spectrum, HMBC spectrum, NMR calculation and ECD calculation, the structure of the daphaulide is determined, and the daphaulide is a novel compound.
Daphaulide F (6) is colorless needle crystal;
Figure BDA0004130778610000031
HRESIMS(m/z 271.1296[M+Na]++, calcd 271.1305) determines the molecular formula as C 15 H 20 O 3 The method comprises the steps of carrying out a first treatment on the surface of the By analysis of daphaulide F 1 H NMR、 13 C NMR, HSQC, HMBC, NMR and ECD calculations, the structure of the daphaulide F is determined as a new compound.
The neuroprotective activity and cholinesterase activity of the 6 novel compounds are examined, and the compounds 2 and 3 show good neuroprotective activity and cholinesterase inhibitory activity, so that the novel guaiane sesquiterpene derivative has the prospect of further developing medicaments for preventing and treating Alzheimer disease.
A pharmaceutical composition comprising a guaiane sesquiterpene derivative prepared from daphne neroli or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier or excipient.
The invention also provides application of the guaiane sesquiterpene derivative prepared from daphne nervosa or the pharmaceutical composition containing the compound in preparation of neuroprotective activity and cholinesterase inhibition activity medicines.
The invention has the advantages that the compounds are novel compounds, have novel structures, are optical pure compounds with determined three-dimensional configuration, and have good neuroprotective activity and cholinesterase inhibiting activity of the compounds 2 and 3, and have further development value.
Figure BDA0004130778610000041
Figure BDA0004130778610000051
Drawings
HRESIMS of Compound 1 of FIG. 1, 1 H、 13 C-NMR and HMBC spectra;
FIG. 2 Compound 2HRESIMS of (1), 1 H、 13 C-NMR and HMBC spectra;
FIG. 3 HRESIMS of Compound 3, 1 H、 13 C-NMR and HMBC spectra;
HRESIMS of Compound 4, 1 H、 13 C-NMR and HMBC spectra;
HRESIMS of Compound 5, 1 H、 13 C-NMR and HMBC spectra;
FIG. 6 HRESIMS of Compound 6, 1 H、 13 C-NMR and HMBC spectra;
FIG. 7X single crystal data for Compound 6;
FIG. 8 Compounds 1-6 1 H- 1 H COSY and HMBC correlation;
FIG. 9 actual measurement and calculation of 3a-3d of Compound 3 13 C NMR chemical shift linear correlation spectrum;
FIG. 10 shows measured and calculated ECD spectra for compounds 1-6;
FIG. 11 dose-dependent inhibition of acetylcholinesterase activity by Compound 2 (a) and Compound 3 (b) (positive drug: donepezil; IC) 50 ＝0.190±0.047μM)；
FIG. 12 dose-dependent inhibition of butyrylcholine ester activity by Compound 2 (a) and Compound 3 (b) (positive drug: donepezil; IC) 50 ＝3.553±0.091μM)；
Figure 13 neuroprotective activity of compound 2 and compound 3.
Detailed Description
The examples set forth below are presented to aid one skilled in the art in a better understanding of the present invention and are not intended to limit the invention in any way.
Example 1
Preparation of Compounds 1-6:
extracting dried daphne neroli whole plant with ethanol, mixing the extracting solutions, concentrating to obtain an extract, extracting the extract with ethyl acetate, subjecting the obtained components to silica gel column chromatography, performing gradient elution with a dichloro-methanol system 1:0-0:1, and collecting 10 components Fr.A-J;
the fraction fr.c was subjected to pigment removal by means of HP20 column chromatography in an ethanol-water system 20:80-100:0.
Performing gradient elution on the component Fr.C by using an ODS column chromatography with an ethanol-water system of 20:80-100:0 to obtain 12 components Fr.C1-Fr.C12;
elution by silica gel column chromatography with petroleum ether-ethyl acetate system 100:1-1:1 and use 70 on preparative reverse phase high performance liquid chromatography: 30-30:70 acetonitrile-water mobile phase to separate Fr.C5, fr.C6 and Fr.C7 to give compounds 1-6.
Example 2
Examination of acetylcholinesterase inhibitory Activity of Compounds 1-6:
the compound was dissolved in DMSO, and buffered with potassium phosphate buffer (KH 2 PO 4 /K 2 HPO 4 0.1m, ph 7.4) to 5 series of concentrations. The reaction system contained 25. Mu.l of the test compound, 12.5. Mu.l of the enzyme, 125. Mu.l of DTNB and 50. Mu.l of ATCI. After the enzyme is added, the reaction starts. The absorbance was measured 3 times at 412nm for 10min after enzyme addition. Nonlinear regression analysis of response concentration (log) curves was performed using Graph-Pad Prism program to calculate IC 50 Values. The experimental results are shown in FIG. 11.
Example 3
Butyrylcholinesterase inhibitory activity of Compounds 1-6 studied:
the compound was dissolved in DMSO, and buffered with potassium phosphate buffer (KH 2 PO 4 /K 2 HPO 4 0.1m, ph 7.4) to 5 series of concentrations. The reaction system contained 25. Mu.l of the test compound, 10. Mu.l of the enzyme, 125. Mu.l of DTNB, and 50. Mu.l of BTCI. After the enzyme is added, the reaction starts. The absorbance was measured 3 times at 412nm for 10min after enzyme addition. Nonlinear regression analysis of response concentration (log) curves was performed using Graph-Pad Prism program to calculate IC 50 Values. The experimental results are shown in FIG. 12.
Example 4
Neuroprotective Activity investigation of Compounds 1-6:
primary rat cortical neuronal cells were placed in DMEM medium containing 10% fbs and cultured under conditions of 100 μg/ml streptomycin and 100U/ml penicillin. When the cell confluency reaches 60% -80%, primary rat cortical nerve cells are planted in a 96-well plate, and the density of the plate is 1 multiplied by 10 6 /ml，100 μl per well, placed at 37deg.C, 5% CO 2 Culturing in the environment.
Primary rat cortical neurons were divided into three groups, control group, glycogen deprivation/reoxygenation (OGD/R), glycogen deprivation/reoxygenation + treatment. By placing primary rat cortical neuron cells in sugarless DMEM medium, and further culturing with 94% N 2 、5％CO 2 、1％O 2 Culturing in a three-gas incubator to establish an in vitro ischemia model (OGD). Afterwards, the OGD model cells were re-placed in complete medium for a further 24 hours to build the OGD/R model.
Cell viability was measured using CCK8 colorimetry. Treatment groups were added with 10 μl CCK8 per well and incubated for 1 hour at 37 ℃; control cells did not require treatment. Absorbance was measured at 450nm using a microplate reader, cell viability (%) = (treatment group OD value-control group OD value)/(OGD/R group OD value-control group OD value). The experimental results are shown in FIG. 13.
It will be apparent to those skilled in the art that various modifications and variations can be made to the present invention without departing from the spirit or scope of the invention. Thus, it is intended that the present invention also include such modifications and alterations insofar as they come within the scope of the appended claims or the equivalents thereof.

Claims (10)

1. A guaiane sesquiterpene derivative in daphne neroli, which is characterized by being any one of the following structures:
Figure FDA0004130778590000011
2. the guaiane sesquiterpene derivative in daphne neroli according to claim 1, wherein the daphne neroli is daphne neroli [ Daphne aurantiaca ] which is a plant of daphne in daphnaceae.
3. A process for the preparation of guaiane sesquiterpene derivatives in daphne neroli according to claim 1 or 2, characterized in that it comprises the following steps:
extracting dried daphne neroli whole plant with ethanol, mixing the extracting solutions, concentrating to obtain an extract, extracting the extract with ethyl acetate, subjecting the obtained components to silica gel column chromatography, and performing gradient elution with a dichloro-methanol system 1:0-0:1 to obtain 10 components Fr.A-J;
performing gradient elution on the component Fr.C by using HP20 and ODS column chromatography in an ethanol-water system of 20:80-100:0 to obtain 12 components Fr.C1-Fr.C12;
eluting with a petroleum ether-ethyl acetate system 100:1-1:1 by silica gel column chromatography and separating Fr.C5, fr.C6 and Fr.C7 on preparative reverse phase high performance liquid chromatography using acetonitrile-water mobile phase gives compounds 1-6.
4. A process for the preparation of guaiane sesquiterpene derivatives in daphne neroli according to claim 3, characterized in that daphne neroli is used as a plant of daphne in daphnaceae, daphne neroli [ Daphne aurantiaca ].
5. A process for the preparation of guaiane sesquiterpene derivatives in daphne nereistolonifera according to claim 3, characterized in that the dried whole daphne nereistolonifera plant is extracted 3 times with 80% industrial ethanol under reflux for 2-3h each time.
6. A process for the preparation of guaiane sesquiterpene derivatives in daphne neroli according to claim 3, characterized in that it comprises the steps of: 30-30:70, fr.c5, fr.c6 and fr.c7 are separated by an acetonitrile-water mobile phase.
7. A pharmaceutical composition comprising a guaiane sesquiterpene derivative or a pharmaceutically acceptable salt thereof in daphne neroli according to claim 1 or 2 and a pharmaceutically acceptable carrier or excipient.
8. Use of a guaiane sesquiterpene derivative or a pharmaceutically acceptable salt thereof in daphne neroli according to claim 1 or 2 for the preparation of a medicament with neuroprotective activity and cholinesterase inhibitory activity.
9. Use of the pharmaceutical composition of claim 7 for the preparation of a medicament having neuroprotective activity and cholinesterase inhibitory activity.
10. Use of a guaiane sesquiterpene derivative or a pharmaceutically acceptable salt thereof in daphne neroli according to claim 1 or 2 or a pharmaceutical composition according to claim 7 in the preparation of a medicament for preventing or treating alzheimer's disease.
CN202310255151.0A 2023-03-15 2023-03-15 New skeleton guaiane sesquiterpene in daphne neroli, and preparation method and application thereof Pending CN116284037A (en)

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