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Isoquinoline tricyclic alkaloid compound as well as preparation method and application thereof

A technology of alkaloids and compounds, applied in the fields of botanical equipment and methods, chemicals for biological control, applications, etc., to achieve the effects of large biological yield, high alkaloid content and wide distribution

Active Publication Date: 2019-11-22
CHINA TOBACCO YUNNAN IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The present invention obtains a new isoquinoline tricyclic alkaloid compound through the research and activity screening of the chemical constituents of Saccharomyces auricosa. This compound has not been reported so far. It is worth mentioning that this compound Possesses significant activity against tobacco black shank virus

Method used

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  • Isoquinoline tricyclic alkaloid compound as well as preparation method and application thereof
  • Isoquinoline tricyclic alkaloid compound as well as preparation method and application thereof
  • Isoquinoline tricyclic alkaloid compound as well as preparation method and application thereof

Examples

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Effect test

Embodiment 1

[0038] Preparation of isoquinoline tricyclic alkaloid compound C 16 h 15 NO 2 , including extracting extract, silica gel column chromatography, and high-pressure liquid chromatography separation, specifically adopting the following steps:

[0039] (1) Extraction of extract: take the whole plant of Sargassum aureus, dry it in the sun, and crush it to 30-50 mesh. Weigh 3.0-4.5kg of the pulverized sample, put it in a 20L glass reaction kettle, add 10-15L of 95% ethanol, reflux for 30-50min, and filter out the extract; add 95% ethanol 10L to the filter residue again ~15L, reflux extraction for 30~50min, filter the extract. The two extracts were combined and concentrated to a small volume, then diluted with 5-8L of 3% tartaric acid solution, and extracted twice with 5-8L of ethyl acetate. After the extraction, the aqueous phase was saturated with sodium carbonate, extracted twice again with 5-8 L of ethyl acetate, the ethyl acetate phase extracted for the second time was combin...

Embodiment 2

[0044] The sample of horsetail lotus came from Heqing County, Dali, Yunnan. Get the whole plant of Saccharomyces japonicus and dry it in the sun, and crush it to 35 meshes. Weigh 3.0kg of the pulverized sample, place it in a 20L glass reactor, add 12L of 95% ethanol, reflux for extraction for 40min, and filter the extract; add 12L of 95% ethanol to the filter residue again, reflux for 40min, filter Remove the extract. The two extracts were combined and concentrated to a small volume, then diluted with 6L of 3% tartaric acid solution, and extracted twice with 6L of ethyl acetate. After the extraction, the aqueous phase was saturated with sodium carbonate, extracted twice with 6 L of ethyl acetate, and the extracted ethyl acetate phases were combined and concentrated under reduced pressure to obtain 48.2 g of alkaloid part extract. The extract is mixed with 60g (80-100 mesh) thick silica gel, dried, and 180g silica gel (150-200 mesh) column chromatography, chloroform: acetone ...

Embodiment 3

[0046] The samples of horsetail lotus came from Binchuan County, Dali, Yunnan. Get the whole plant of Saccharomyces japonicus and dry it in the sun, and crush it to 40 mesh. Weigh 3.8kg of crushed sample, put it in a 20L glass reaction kettle, add 14L of 95% ethanol, reflux for extraction for 30min, and filter out the extract; add 14L of 95% ethanol to the filter residue again, reflux for 30min, filter Remove the extract. The two extracts were combined and concentrated to a small volume, then diluted with 8 L of 3% tartaric acid solution, and extracted twice with 8 L of ethyl acetate. After the extraction, the aqueous phase was saturated with sodium carbonate, extracted twice again with 8 L of ethyl acetate, and the extracted ethyl acetate phases were combined and concentrated under reduced pressure to obtain 46.7 g of alkaloid part extract. The extract is mixed with 60g (80-100 mesh) thick silica gel, dried, and 220g silica gel (150-200 mesh) column chromatography, chlorofo...

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Abstract

The invention discloses an isoquinoline tricyclic alkaloid compound as well as a preparation method and application thereof. The compound is obtained by taking a whole plant of Thalictrum glandulosissimum as a raw material and by steps of extraction with ethyl acetate, silica gel column chromatography and high-pressure liquid chromatography separation and purification. The structural formula of the compound is C16H15NO2, and the compound has the following structural formula shown in the specification. The compound is named as 1-(2,2-dimethyl-2H-pyrano[2,3-g]isoquinolin-6-yl)ethanone. The inhibitory effect of the compound on Phytophthora nicotianae is remarkably superior to that of agricultural streptomycin, and the control effect on tobacco black shank reaches (71.5 + / - 3.2)%. The raw material is widely distributed, high in biological yield and high in alkaloid content. The compound preparation process is simple, the production cost is low and the compound is prone to industrial application.

Description

technical field [0001] The invention belongs to the technical field of biopesticides, and in particular relates to an isoquinoline tricyclic alkaloid compound obtained by extracting and separating for the first time from the horsetail lotus. At the same time, the invention also relates to the preparation method of the compound and the application of the compound in the prevention and treatment of tobacco black shank. Background technique [0002] Thalictrum L. (Latin scientific name: Thalictrum L.) is a perennial herb of the family Ranunculaceae. There are about 200 species of this genus in the world, which are widely distributed in Asia, Europe, Africa, North America and South America; among them, there are about 67 species in China, which are distributed in all provinces and regions of the country, and most of them are distributed in the southwest. About 29 species of plants in this genus are available for medicinal purposes, and many plants in this genus have the effects...

Claims

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Application Information

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IPC IPC(8): C07D491/052A01N43/90A01P1/00
CPCA01N43/90C07D491/052
Inventor 李雪梅黄海涛高茜杨光宇李晶孔维松王晋许永胡秋芬刘欣宋春满
Owner CHINA TOBACCO YUNNAN IND
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