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Rubiaceae type cyclic peptide diglycoside and its preparation method and application

A technology of Rubiaceae and Rubia genus, applied in the field of extraction and separation of natural organic compounds, can solve the problems that have not yet been reported on Rubiaceae type cyclic peptide diglycosides, and achieve good application prospects and good technical application prospects

Active Publication Date: 2021-12-28
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 cyclic peptide diglycoside and its preparation method and application
  • Rubiaceae type cyclic peptide diglycoside and its preparation method and application
  • Rubiaceae type cyclic peptide diglycoside and its preparation method and application

Examples

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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 a rubiaceae type cyclic peptide diglucoside as well as its preparation method and application. The preparation method of the Rubiaceae type cyclic peptide diglycoside is as follows: using the stem and / leaf of the Rubiaceae Rubio genus Arthropodium as raw materials to obtain its extract, and the obtained extract is sequentially passed through a macroporous resin column, a silica gel column, a reversed-phase Silica gel column separation and purification, namely; when separated and purified by a macroporous resin column, the eluent is a mixed solvent composed of methanol or ethanol and water; when separated and purified by a silica gel column, the eluent is composed of chloroform and methanol mixed solvent; when separated and purified by a reverse-phase silica gel column, the eluent is a mixed solvent composed of methanol or acetonitrile and water. The applicant's experimental results show that the above-mentioned Rubiaceae type cyclic peptidoside has inhibitory activity of NF-κB signaling pathway and can be used as an inhibitor of NF-κB signaling pathway. The Rubiaceae type cyclic peptidoside has a structure shown in the 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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Patent Type & Authority Patents(China)
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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