Rubiaceae-type cyclopeptide bioside, method for preparing same and application of rubiaceae-type cyclopeptide bioside

A technology of Rubiaceae and Rubiaceae, which is applied in the field of extraction and separation of natural organic compounds, can solve problems such as no reports of Rubiaceae type cyclopeptide diglycosides, and achieves good application prospects and good technical application prospects.

Active Publication Date: 2019-01-04
GUANGXI INST OF BOTANY THE CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] So far, there are no relevant reports on Rubiaceae type cyclic peptidosides and their application as NF-κB signaling pathway inhibitors.

Method used

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  • Rubiaceae-type cyclopeptide bioside, method for preparing same and application of rubiaceae-type cyclopeptide bioside
  • Rubiaceae-type cyclopeptide bioside, method for preparing same and application of rubiaceae-type cyclopeptide bioside
  • Rubiaceae-type cyclopeptide bioside, method for preparing same and application of rubiaceae-type cyclopeptide bioside

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Take the dried stems and leaves (2.0kg) of Rubia hangii (Rubia hangii), after pulverization, reflux extraction with 100v / v% methanol for 3 times (20L×3 times), the time is 3 hours each time, The extract was concentrated under reduced pressure to obtain 263 g of methanol extract; after the methanol extract was suspended in 5 L of methanol / water (the volume ratio of methanol and water was 50:50), it was extracted 3 times with petroleum ether, and the amount of each extraction solvent was 5L. After the extraction is complete, take the methanol / water phase (lower phase), filter it, remove the organic solvent under reduced pressure, add 3L of water, and put it on an XAD-16 macroporous resin column (φ50×1000mm). / v% methanol for elution, and finally 100 v / v% methanol for elution. Collect the fraction eluted with 100v / v% methanol and concentrate under reduced pressure to obtain Fr.2, which is mixed with silica gel and subjected to silica gel column chromatography, and eluted ...

Embodiment 2

[0052] Take the dried stems and leaves (2.0kg) of Rubia hangii (Rubia hangii), after pulverization, reflux extraction with 95v / v% ethanol for 3 times (20L×3 times), the time is 3 hours each time, The extract was concentrated under reduced pressure to obtain 237g of ethanol extract; after the ethanol extract was suspended in 5L of methanol / water (the volume ratio of methanol and water was 50:50), it was extracted 3 times with petroleum ether, and the amount of each extraction solvent was 5L. After the extraction is complete, take the methanol / water phase (lower phase), filter it, remove the organic solvent under reduced pressure, add 3 L of water, and extract 3 times with ethyl acetate, and the amount of solvent used for each extraction is 5 L. After the extraction is complete, take the water phase (lower phase) and put it on a DA101 macroporous resin column (φ 50×1000mm). After loading, the column is first washed with water, then eluted with 50v / v% methanol, and finally eluted...

Embodiment 3

[0055] Take the stems and leaves (3.0kg) of Rubia hangii (Rubia hangii), dry and pulverize them, boil them with water for 3 times (20L x 3 times) for 30 minutes each time, filter them, and collect them separately The three extractions are applied to the X-5 macroporous resin column (φ50×1000mm), the third extraction is applied first, then the second extraction, and finally the first extraction. After loading, first wash the column with water, then elute with 20v / v% methanol, and finally elute with 80v / v% methanol. Collect the fraction eluted with 80v / v% methanol and concentrate under reduced pressure to obtain Fr.2, which is mixed with silica gel and subjected to silica gel column chromatography, and eluted with a gradient of chloroform / methanol with a volume ratio of 100:0~0:100 (100:0 , 95:5, 90:10, 80:20, 70:30, 60:40, 50:50, 40:60, 0:100), combined with the TLC detection method of cyclic peptide, to determine the 80:20 elution Part of it is the part containing cyclic pept...

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Abstract

The invention discloses rubiaceae-type cyclopeptide bioside, a method for preparing the same and application of the rubiaceae-type cyclopeptide bioside. The method for preparing the rubiaceae-type cyclopeptide bioside includes acquiring extract from stems and / or leaves of rubiaceae rubia plants rubia hangii; sequentially separating and purifying the obtained extract by macroporous resin columns, silica gel columns and reverse phase silica gel columns to obtain the rubiaceae-type cyclopeptide bioside. Eluents are mixed solvents with methanol or ethyl alcohol and water when the extract is separated and purified by the macroporous resin columns; eluents are mixed solvents with chloroform and methanol when the extract is separated and purified by the silica gel columns; eluents are mixed solvents with methanol or acetonitrile and water when the extract is separated and purified by the reverse phase silica gel columns. The rubiaceae-type cyclopeptide bioside, the method and the applicationhave the advantages that as shown by experimental results obtained by the inventor, the rubiaceae-type cyclopeptide bioside has NF-kB signal pathway inhibitory activity and can be used as an NF-kB signal pathway inhibitor; the rubiaceae-type cyclopeptide bioside is provided with a structure shown as a following formula (I).

Description

technical field [0001] The invention relates to the extraction and separation of natural organic compounds in plants, in particular to a rubiaceae type cyclic peptide diglycoside and its preparation method and application. Background technique [0002] Cyclic peptides are a class of cyclic compounds mainly composed of amino acids connected by peptide bonds. At present, there are about 500 kinds of cyclic peptide compounds found in nature, and many cyclic peptides have good biological activities. Rubiaceae-type cyclic peptides are a class of bicyclic or monocyclic cyclohexyl peptides discovered from Rubiaceae. At present, about 40 Rubiaceae-type cyclic peptide compounds have been discovered, including monoglycosides and dimers. [0003] NF-κB signaling pathway is one of the classic and important signaling pathways in cells. Ranjan Sen and David Baltimore first discovered the nuclear transcription factor NF-κB in 1986. It is a protein factor that can specifically bind to the...

Claims

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Application Information

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IPC IPC(8): C07K11/02C07K1/20C07K1/02A61K38/12A61P29/00A61P37/00A61P35/00
CPCA61P29/00A61P35/00A61P37/00C07K11/02A61K38/00
Inventor 谢运昌宾祝芳刘演张强蒋小华梁勇诗
Owner GUANGXI INST OF BOTANY THE CHINESE ACAD OF SCI
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