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A kind of extract of Selaginella cuspidatum and its preparation method and application

A technology of Selaginella cuspidatum and extract, which is applied in the field of Selaginella cuspidatum extract and its preparation, can solve the problem that there is no research on PDE4 inhibitor, and achieve the effect of good inhibitory activity and selectivity

Active Publication Date: 2015-09-09
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, only perynylphenol selaginellin compounds are reported in Selaginella cuspidatum, and they are mostly used for antibacterial and antioxidation, and there is no research on them as PDE4 inhibitors.

Method used

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  • A kind of extract of Selaginella cuspidatum and its preparation method and application
  • A kind of extract of Selaginella cuspidatum and its preparation method and application
  • A kind of extract of Selaginella cuspidatum and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Preparation of Selaginella Cushion Extract

[0045] Take 1 kg of the whole herb of Selaginella cushion-like, and grind it into coarse powder. Add 8 times the volume of 95% ethanol, soak for 7 days, filter under reduced pressure, recover ethanol under reduced pressure, and concentrate the remaining liquid to a thick paste with a relative density of 1.25. The step of soaking and extracting was repeated more than two times to finally obtain 50 g of the ethanol extract of Selaginella cushion. The ethanol extract of Selaginella cuspidatum was dissolved in 1L of water, and extracted three times with equal amounts of petroleum ether and ethyl acetate respectively. The ethyl acetate extracts were combined and concentrated under reduced pressure to obtain 39 g of ethyl acetate extract.

Embodiment 2

[0047] Separation of monomeric compounds

[0048] According to Example 1, 39 g of ethyl acetate extract was obtained, and the ethyl acetate extract was initially segmented by MCI column, and eluted with methanol:water=3:7~10:0; then 200-300 mesh column chromatography silica gel was used to Petroleum ether: ethyl acetate or petroleum ether: acetone or chloroform: gradient elution in solvent systems such as methanol, and then repeatedly use gel column LH-20, ODS column purification, and finally through semi-preparative high performance liquid chromatography (acetonitrile: water) ) or (methanol: water) to further purify, and finally obtain 6 monomeric compounds, the specific separation process refers to figure 1 .

Embodiment 3

[0050]DZJB-1: Preparation of 4,4'-(7-hydroxy-2-hydroxymethyl-1-(4-hydroxyphenyl)ethynyl-9H-fluorene-9,9-disubstituted)biphenol

[0051] According to the method of Example 2, finally by gel (LH-20 chloroform:methanol=1:1) purification, recrystallization, obtain title compound, yellow bulk crystal, its structure is as follows:

[0052]

[0053] UV(MeOH)λ max (log ε)204(4.84)nm, 300(4.47)nm.

[0054] IR(KBr)ν max 3312, 2207, 1607, 1510, 1449, 1357, 1241, 1174 and 833cm -1 .

[0055] Negative ESIMSm / z511.2[M-H] - ,546.9[M+Cl] - ,556.7[M+HCOO] - ;HRESIMS m / z511.1543[M+H] + (calcd for C 34 h 24 o 5 , 511.1551).

[0056] 4,4'-(7-Hydroxy-2-hydroxymethyl-1-(4-hydroxyphenyl)ethynyl-9H-fluorene-9,9-disubstituted)biphenol spectral data (400MHz, Methanol-d4)

[0057]

[0058]

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Abstract

An in-depth study is performed on selaginella pulvinata extractives in the present invention, and it is found that the selaginella pulvinata extractives have a significant anti-inflammatory activity. Multiple column chromatography separation technologies and a semi-preparation high-performance liquid chromatography separation method are used to extract and separate a class of compounds (DZJB1-6) with a 9,9-diphenyl-1-(phenylethynyl)-9H-fluorene new skeleton structure, named as selaginpulvilinsA-F (structural formula (I)). The six compounds extracted and separated from selaginella pulvinata are subjected to structural modification, and then a series of compounds are obtained. These compounds can significantly inhibit the activity of type-4 phosphodiesterase (PDE4), and can be used for preparing PDE4 inhibitors, and treating asthma, chronic obstructive pneumonia, inflammations, and the like. According to the present invention, a new structure is provided for the development of PDE4 inhibitors.

Description

technical field [0001] The present invention relates to a natural extract and its modification, more specifically, to an extract of Selaginella custata and its preparation method and application. Background technique [0002] Cyclic nucleotide phosphodiesterases (PDEs) are an important family of super enzymes, through the hydrolysis of cAMP and cGMP, effectively control the concentration of cAMP and cGMP in cells, thereby regulating the transmission of second messengers in the body biochemical effect. PDEs are widely distributed in mammalian tissues, and their diversity leads to specific distribution of different PDE enzymes at the cellular and subcellular levels, which can selectively regulate a variety of cellular functions, and are good drug design and therapeutic targets. [0003] Phosphodiesterase type 4 (PDE4), as a PDE family enzyme that specifically catalyzes the hydrolysis of cAMP, is mainly distributed in inflammatory cells in the human body. In the inflammatory ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C27/26C07C39/23C07C37/70C07C45/78C07C47/57C07C41/34C07C43/23C07C47/575C07C51/42C07C65/28C07C65/19C07C67/48C07C69/21A61P29/00
CPCC07C39/23C07C43/23C07C47/57C07C47/575C07C65/19C07C65/28C07C69/21C07C2603/18A61P29/00C07C45/79C07C51/47C07C67/56C07C69/16
Inventor 尹胜罗海彬刘信黄仪有
Owner SUN YAT SEN UNIV
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