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Phenylacetamide compounds as well as preparation method and use thereof

A compound, phenethyl technology, applied in the field of phytochemistry, can solve problems that have not been reported yet

Active Publication Date: 2018-12-18
CHINA TOBACCO YUNNAN IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the present invention, a phenethyl cinnamamide-linked glycoside compound is isolated from the plant Ganqing Qinglan for the first time, and no relevant reports have been seen on this compound so far

Method used

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  • Phenylacetamide compounds as well as preparation method and use thereof
  • Phenylacetamide compounds as well as preparation method and use thereof
  • Phenylacetamide compounds as well as preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] The raw material is Ganqing Qinglan collected from Kunming, Yunnan Province. Dry the whole herb of Ganqing Qinglan and crush it to 80 meshes to obtain 9.5 kg of Ganqing Qinglan coarse powder, extract 6 times with 95v / v% ethanol ultrasonically, extract for 3 days each time, combine the extracts, filter, and concentrate under reduced pressure to obtain Ointment, about 1.2kg of extractum was obtained. After dissolving the extract with 1.5 times the amount of pure methanol by weight, mix the sample with 1.5kg of 100-200 mesh silica gel, take 6.0kg of 100-200 mesh silica gel dry method for silica gel column chromatography, and use a volume ratio of 50: 1, 40:1, 30:1, 20:1, 10:1, 1:1 and 0:1 ethyl acetate:methanol solution carried out gradient elution, TLC monitoring merged the same part, obtained 7 parts, wherein The elution fraction that the volume ratio is 10:1 uses Sephadex LH-20 type Sephadex column chromatography, carries out elution with pure methanol as mobile phase,...

Embodiment 2

[0046] The raw material is Ganqing Qinglan collected from Yuxi area of ​​Yunnan Province. Dry the whole herb of Ganqing Qinglan and crush it to 80 meshes to obtain 6.5 kg of Ganqing Qinglan coarse powder, extract 6 times with 95v / v% ethanol ultrasonically, extract 3 days each time, combine the extracts, filter, and concentrate under reduced pressure to obtain paste, about 800g of extract. The extract is dissolved in pure methanol with a weight ratio of 1.5 times, and then mixed with 1.2kg of 100-200 mesh silica gel, and 4.0kg of 100-200 mesh silica gel is dry-packed for silica gel column chromatography, with a volume ratio of 50 :1, 40:1, 30:1, 20:1, 10:1, 1:1 and 0:1 ethyl acetate:methanol solution for gradient elution, TLC monitoring and merging of the same parts to obtain 7 parts, Wherein the elution part that volume ratio is 10:1 uses Sephadex LH-20 type Sephadex column chromatography, carries out elution with pure methanol as mobile phase, collects eluent, then above elu...

Embodiment 3

[0048] The compound prepared in Example 1 is a light yellow oil; the determination method is: use nuclear magnetic resonance in combination with other spectral techniques to identify the structure.

[0049] (1) UV spectrum (solvent is methanol), λ max (logε)203(3.70), 215(3.59), 254(3.32)nm;

[0050] (2) Infrared Spectrum (Potassium Bromide Tablet) ν max 3393, 2920, 2849, 1646, 1509, 1469, 1420, 1229, 1073, 1024, 774, 696cm -1 ;

[0051] (3) High-resolution mass spectrometry HRESI-MS shows that its quasi-molecular ion peak is 598.2259[M+Na] + (computed value 598.2259), combined with 1 H NMR and DEPT spectra confirmed its molecular formula as C 29 h 37 NO 11 , with an unsaturation of 12. The hydroxyl group (3393cm -1 ), carbonyl (1646cm -1 ) and aromatic rings (1509, 1469 and 1420cm -1 ) resonance absorption peak.

[0052] From 1 H and 13 C NMR spectrum (see Table-1 for data affiliation) signals can be seen that the 29 carbons of the compound include 1 methyl gro...

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Abstract

The invention discloses phenylethyl cinnamamide compounds; the structural formula of the compounds is described in the description; the compounds are named as (Z) 4-O-[beta-D-glucopyranosyl-(1-3)-alpha-L-pyran rhamnosyl]phenylethyl cinnamamide, and the molecular formula of the compounds is C29H37NO11. The invention also discloses a preparation method of the phenylethyl cinnamamide compounds and use of the phenylethyl cinnamamide compounds in preparation of a diabetes inhibitor.

Description

technical field [0001] The invention belongs to the technical field of phytochemistry, and specifically relates to a novel phenethyl cinnamic amide compound extracted from Ganqing Qinglan, its preparation method and application. Background technique [0002] Labiatae (Labiatae) Dracocephalum plants are perennial herbaceous plants. There are about 60 species distributed in the world. This genus is rich in resources in my country. There are about 32 species and 7 varieties, mainly distributed in North China, Northeast China, In Southwest and Northwest regions, plants of the genus Qinglan are mostly used as Tibetan medicine among the people. Tibetan medicine Dracocephalum tanguticum Maxim., also known as Tanguticum Maxim., has the effects of clearing away heat and dampness, dispelling wind and relieving the exterior, soothing the liver and harmonizing the stomach. It is used to treat dizziness, hepatitis, gastritis, arthritis, boils and other diseases. This genus is rich in phy...

Claims

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Application Information

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IPC IPC(8): C07H1/08C07H15/203A61P3/10
CPCA61P3/10C07H1/08C07H15/203
Inventor 雷声段焰青刘秀明张翼鹏李源栋郭青杨乾栩何靓李干鹏马恩广
Owner CHINA TOBACCO YUNNAN IND
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