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Novel steroidal saponins and their applications

A technology of steroidal saponins and compounds, applied in the field of medicine, can solve problems such as insufficient research on the chemical constituents of Solanum nigrum, chemical structure and anti-inflammatory and anti-tumor activities have not been reported, and achieve good in vitro anti-inflammatory activity, chemically defined effect

Active Publication Date: 2018-12-07
GUANGDONG PHARMA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing research on the chemical constituents of Solanum nigrum is still not thorough enough, so the chemical constituents of steroids in Solanum nigrum are worthy of further research and development.
We have systematically separated the steroidal saponins from Solanum nigrum and obtained a new class of steroidal saponins whose chemical structure and anti-inflammatory and anti-tumor activities have not been reported before.

Method used

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  • Novel steroidal saponins and their applications
  • Novel steroidal saponins and their applications
  • Novel steroidal saponins and their applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The extraction of embodiment 1 steroidal saponins

[0032] Take 6 kg of dried Solanum solanum fruit, extract twice with cyclohexane under reflux, and discard the cyclohexane extract. The medicinal material after degreasing treatment is heated and refluxed with 10 times the amount of 70% methanol and extracted three times for 2 hours each time, and the combined extracts are concentrated under reduced pressure to obtain the extract. Suspend the extract in water, pass through a D101 macroporous resin column (1300×100mm), and elute with water, 10% methanol, 30% methanol, 50% methanol, 70% methanol and 100% methanol, among which 50% methanol Compound 1-9 was isolated by repeated silica gel column chromatography, reverse-phase MPLC column chromatography, Sephadex LH-20 column chromatography and semi-preparative reverse-phase HPLC column chromatography.

Embodiment 2

[0033] Identification of Example 2 Compound 1

[0034] By means of physical and chemical constants and spectroscopy (HRESIMS, 1 H-NMR, 13 C-NMR, HSQC, HMBC and 1 H- 1 H COZY spectrum) to identify compound 1, the results are as follows:

[0035] Compound 1 is a white amorphous powder, The reaction to Anisaldehyde (A reagent) showed yellow color, but to Ehrlish (E reagent) showed no color, and acid hydrolysis detected D-glucose and D-galactose, suggesting that the compound was a spirosteroid saponin compound. HRESIMS (positive) gives the quasi-molecular ion peak [M+NH 4 ] + m / z 1128.5492 (calcd.for C 51 h 86 NO 26 1128.5438), suggesting that its molecular weight is 1110, combined with 1 H-NMR and 13 C-NMR (DEPT) can determine its molecular formula as C 51 h 82 o 26 .

[0036] exist 1 In the H-NMR spectrum, the high-field region gives four characteristic methyl signals on steroidal saponins, two of which are single peaks, and the other two are double peaks, resp...

Embodiment 3

[0042] Identification of Example 3 Compound 2

[0043] By means of physical and chemical constants and spectroscopy (HRESIMS, 1 H-NMR, 13 C-NMR, HSQC, HMBC and 1 H- 1 H COZY spectrum) to identify compound 2, the results are as follows:

[0044] Compound 2 is a white amorphous powder, The reaction to Anisaldehyde (A reagent) showed yellow color, but to Ehrlish (E reagent) showed no color, and acid hydrolysis detected D-glucose and D-galactose, suggesting that the compound was a spirosteroid saponin compound. HRESIMS (positive) gives the quasi-molecular ion peak [M+NH 4 ] + m / z 1128.5497 (calcd.forC 51 h 86 NO 26 1128.5438), suggesting that its molecular weight is 1110, combined with 1 H-NMR and 13 C-NMR (DEPT) can determine its molecular formula as C 51 h 82 o 26 .

[0045] exist 1 In the H-NMR spectrum, the high-field region gives four characteristic methyl signals on steroidal saponins, two of which are single peaks and the other two are double peaks, respec...

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Abstract

The invention belongs to the technical field of medicines and in particular relates to a type of novel steroid saponin compounds and an application thereof. The steroid saponin compounds are prepared by the steps: performing degreasing treatment on solanum nigrum green fruits, performing solvent extraction, eluting by using a D101 macroporous resin column, separating through repeated silica gel column chromatography, reversed-phase MPLC (Middle Pressure Liquid Chromatography), Sephadex LH-20 column chromatography, semi-preparative reversed phase HPLC (High Performance Liquid Chromatography) and other means, thereby obtaining the product. Nine compounds with clear chemical structures are identified by virtue of physico-chemical constants and modern spectroscopy means. Pharmacodynamic experiments prove that the nine novel steroid saponin compounds have excellent in-vitro anti-inflammatory activities and have different degrees of tumor inhibiting effects on three tumor strains of human acute myeloid leukemia cells HL-60, human tissue lymphoma cells U937 and human hepatoma cells HepG2. The novel steroid saponin compounds can be further taken as anti-inflammatory and antitumor drugs to be researched and developed.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a class of novel steroidal saponin compounds and applications thereof. Background technique [0002] Inflammation is a defense response of living tissue with vascular system to damaging factors. Most diseases are accompanied by inflammation, which can aggravate the occurrence and development of diseases, and some chronic inflammation can lead to the occurrence of tumors. Therefore, the control and treatment of inflammation is of great significance. [0003] Natural medicines, especially those derived from plants, have a variety of chemical structures and biological activities, and have always been the main source of human disease prevention and treatment. Many clinically used drugs are directly or indirectly derived from natural products. Natural products can not only be used as precursors for the semi-synthesis of drugs, but also as templates for the chemical synth...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J71/00A61K31/58A61P35/00
CPCA61K31/585C07J71/0005C07J71/0026
Inventor 何祥久向丽敏王宜海易晓敏
Owner GUANGDONG PHARMA UNIV
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