Cadinane sesquiterpene compounds, preparation method and use thereof in medicine preparation

A technology for sesquiterpenoids and compounds, applied in the field of juniperane-type sesquiterpenoids and their preparation, can solve the problems of chemical composition and pharmacological activity without any reports and the like

Active Publication Date: 2017-12-12
FUDAN UNIV
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Problems solved by technology

At present, there is no report on its chemical composition and pharmacological activity.

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  • Cadinane sesquiterpene compounds, preparation method and use thereof in medicine preparation

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Embodiment 1

[0020] Example 1 Preparation of juniperane-type sesquiterpenes (manglietone B)

[0021] Take 1.2 kg of Mangosteen leaves, crush them and extract them by cold-soaking with 95% ethanol at room temperature for 3 times, combine the extracts, concentrate under reduced pressure, and obtain 47.5 grams of extract. The extract was dispersed with methanol aqueous solution (15%, v / v), loaded on the MCI resin column, and gradient eluted with methanol-water solution (from 50% to 100%, v / v). The fraction eluted with 60%~70% (v / v) methanol was further separated by silica gel column chromatography, and gradient eluted with petroleum ether-acetone (4:1-1:0, v / v) solution, Six subfractions (Fr. A–Fr. F) were obtained. Subcomponent Fr. A was subjected to Sephadex LH-20 (eluent: methanol) and semi-preparative HPLC (MeOH / H 2 0,60:40, v / v, 3.0 mL / min) was further separated and purified to obtain the compound manglietone B (1.1 mg, t R =27.0 min);

[0022] The obtained compound manglietone B i...

Embodiment 2

[0024] Example 2: Determination of protein tyrosine phosphatase 1B inhibitory activity

[0025] Using the method of molecular biology, construct the recombinant hGST-PTP1B-BL21 E. coli Human PTP1B engineering bacteria, the purified hGST-PTP1B recombinant protein can hydrolyze the substrate para -Nitrophenyl Phosphate (pNPP) phospholipid bond, the obtained dephosphorylated product pNP has a strong light absorption at a wavelength of 405 nm, so the change of the enzyme activity and the effect of the compound on the enzyme activity can be observed by directly detecting the change of the light absorption at 405 nm Inhibition situation; initial screening selects described compound concentration as 20 µ The percentage inhibition rate of PTP1B enzyme activity was investigated at g / ml, and the test results showed that the inhibition rate of manglietone B was higher than 60%; further determination of IC 50 Value: the sample was dissolved in DMSO to make a suitable concentration be...

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Abstract

The invention belongs to the field of traditional Chinese medicine preparation, and specifically relates to cadinane sesquiterpene compounds extracted and separated from branches and leaves of Manglietia aromatic Dandy. The preparation method provided by the invention uses technologies of infrared, ultraviolet, mass spectrum (high and low resolution), 1D/2D nulcear magnetic resonance (NMR) and the like to confirm the structures of the cadinane sesquiterpene compounds, and uses a method of calculating circular dichroism (ECD) to confirm the absolute configurations of the cadinane sesquiterpene compounds. An in vitro inhibitory activity test is performed, and the result shows that the compounds have notable protein tyrosine phosphatase 1B(PTP1B) inhibitory activity, can be used as an inhibitor of the protein tyrosine phosphatase 1B and an insulin sensitizer, and can be further used for preparing medicines for preventing or curing the PTP1B mediated diseases, especially II-type diabetes, obesity and complications of the PTP1B mediated diseases, or lead compounds of the medicines.

Description

technical field [0001] The invention belongs to the field of traditional Chinese medicine pharmacy, and relates to a juniperane-type sesquiterpene compound, a preparation method thereof and a new application in preparation of medicines. specifically related to the Manglietia aromatic Dandy) and its preparation method. The compound can be used as an inhibitor of protein tyrosine phosphatase 1B (PTP1B) and an insulin sensitizer, and further used in the preparation of drugs for preventing or treating diseases mediated by PTP1B, especially type II diabetes, obesity and its complications Or lead compounds of such drugs. Background technique [0002] The prior art discloses that protein tyrosine phosphatase (protein tyrosine phosphatase, PTP) is an enzyme family that regulates the phosphorylation level of protein tyrosine residues in cells, and is closely related to cell proliferation and various intracellular signal transduction processes ( Fischer et al, Science 1991, 253: 40...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/733C07C45/78A61P5/50A61P3/10A61P3/04
CPCC07B2200/07C07C45/78C07C49/733
Inventor 胡金锋王立军熊娟唐宇麻光磊
Owner FUDAN UNIV
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