Three alkaloid compounds in purslane and extraction and separation method thereof

A technology of alkaloids and separation methods, applied in the field of three alkaloid compounds and their extraction and separation, can solve the problem of low structural novelty, and achieve the effect of environmentally friendly process methods, simple and fast operation methods

Active Publication Date: 2021-08-31
LIAONING UNIV OF TRADITIONAL CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, most of the chemical components isolated from purslane are known, and the structural novelty is low. Therefore, the development and isolation of compounds in purslane are urgently needed

Method used

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  • Three alkaloid compounds in purslane and extraction and separation method thereof
  • Three alkaloid compounds in purslane and extraction and separation method thereof
  • Three alkaloid compounds in purslane and extraction and separation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0059] The present invention provides three kinds of alkaloid compounds, molecular formula is C 16 h 15 NO 5 (1), C 13 h 11 NO 3 (2), C 14 h 13 NO 3 (3), and named according to its structure 4,9,10-trihydroxy-2-methoxy-6,7-dihydrodibenzo[b,e]azocin-12(5H)-one(1), 9,10-dihydroxy- 5,6-dihydro-11H-benzo[d]pyrrolo[1,2-a]azepin-11-one (2), 8,9-dihydroxy-6,11-dihydro-5H-benzo[d]pyrrolo[1 ,2-a]azepine-3-carbaldehyde (3), the chemical structural formula is:

[0060] .

[0061] The NMR data of the three alkaloid compounds are shown in Table 1: 1 H-NMR with 13 C-NMR in MeOD.

[0062] Table 1: NMR data of three alkaloid compounds of the present invention

[0063] .

[0064] The alkaloid compound 1 of the present invention is named 4,9,10-trihydroxy-2-methoxy-6,7-dihydrodibenzo[b,e]azocin-12(5H)-one according to the structure identification and derivation, Table 1 is NMR data of the alkaloid compound.

[0065] 4,9,10-trihydroxy-2-methoxy-6,7-dihydrodibenzo[b,e]azocin-1...

Embodiment 2

[0079] Example 2 Anti-inflammatory effects of three alkaloid compounds of the present invention.

[0080] 1. Main materials.

[0081] 1.1. Drugs and reagents: The compounds used in the experiment were prepared by the above method with a purity of ≥98%, weighed accurately, and diluted with DMSO to the required solutions for the following dosage groups. Fetal bovine serum (U.S. Hyclone Company); penicillin and streptomycin (Hangzhou Sijiqing Company); DMSO (U.S. Sigma Company); CCK-8 kit (Wuhan Boster Bioengineering Co., Ltd.); DMEM high glucose medium, LPS , IL-1 β , TNF- α ELISA kit (Soleibao Technology Co., Ltd.); cell lysate.

[0082] 1.2 Cell line: RAW264.7 macrophages (US ATCC cell bank).

[0083] 1.3 Grouping: control group, LPS group and experimental group, each group.

[0084] 2 Experimental methods.

[0085] 2.1 Cell culture, DMEM high-glucose medium, add 10% fetal bovine serum, 1% antibiotics (100U / mL penicillin and 100μg / mL streptomycin), place at 37°C, 5% CO ...

Embodiment 3

[0098] Example 3 Anticholinesterase effect of three compounds of the present invention.

[0099] 1. Main materials.

[0100] Drugs and reagents: The alkaloid compounds used in the experiment were prepared by the above method with a purity of ≥98%, sodium dihydrogen phosphate, disodium hydrogen phosphate (Sinopharm Chemical Reagent Co., Ltd.), physostigmine (Hanxiang Biotechnology), phosphorus 5 , 5'-dithiobisnitrobenzoic acid (Dithiobisnitrobenzoic acid, DTNB, Shanghai Jinsui Biotechnology Co., Ltd.), acetylcholinesterase (AChE) and iodide thioacetylcholine (Acetylthiocholine iodide, ATCI, Dalian Meilun Biotechnology Co., Ltd.).

[0101] 2. Grouping: divided into blank group, control group and sample group.

[0102] 3 Experimental methods.

[0103] 3.1 Sample preparation

[0104] Precisely weigh the sample and 0.11 mg of physostigmine, respectively, and use methanol as a solvent to prepare five gradient concentrations of 2.5 μM, 5.0 μM, 10.0 μM, 20.0 μM and 40.0 μM. Accur...

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Abstract

The invention relates to the field of traditional Chinese medicine extraction and separation, in particular to three alkaloid compounds extracted, separated and identified from purslane and an extraction and separation method thereof. The molecular formulas of the three alkaloid compounds are respectively C16H15NO5, C13H11NO3 and C14H13NO3, and the three alkaloid compounds are respectively named as 4,9,10-trihydroxy-2-methoxy-6,7-dihydrodibenzo [b,e]azocin-12(5H)-one, 9,10-dihydroxy-5,6-dihydro-11H-benzo[d]pyrrolo[1,2-a]azepin-11-one, and 8,9-dihydroxy-6,11-dihydro-5H-benzo[d] pyrrolo[1,2-a]azepine-3-carbaldehyde. The invention further provides an extraction and separation method of the alkaloid compounds. The extraction and separation method sequentially comprises the steps of ethanol reflux extraction, silica gel column chromatography, ODS medium-pressure column and hydroxypropyl dextran column chromatography purification and HPLC separation and preparation. The structures of the novel alkaloid compounds are determined by adopting methods of 1H-NMR, 13C-NMR and UHPLC-ESI-TOF-MS. The three compounds have potential anti-inflammatory and anti-cholinesterase activities and the like, a preparation method is provided, and a primer and a theoretical basis are provided for developing new drugs and new components.

Description

technical field [0001] The invention relates to the field of extraction and separation of traditional Chinese medicines, in particular to three alkaloid compounds extracted, separated and identified from purslane medicinal material and an extraction and separation method thereof. Background technique [0002] purslane( Portulaca oleracea L.), also known as long-lived vegetable and horse amaranth, is a plant of the family Portulaca oleracea. Purslane likes fertile soil, is resistant to drought and waterlogging, has strong vitality, is widely distributed, and is rich in resources, and it is more common in Northeast my country. Purslane can be used as both medicine and food, and it is one of the wild plants with the same origin of medicine and food designated by the Ministry of Health of my country. The 2020 edition of "The Pharmacopoeia of the People's Republic of China" records that the dried aerial part of purslane is used as medicine. It has the effects of clearing away ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D225/08C07D487/04A61P29/00A61P43/00
CPCC07D225/08C07D487/04A61P29/00A61P43/00Y02A50/30
Inventor 英锡相崔馨予英哲铭兰秀娟
Owner LIAONING UNIV OF TRADITIONAL CHINESE MEDICINE
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