Monocyclic diterpene compound cassipourol, and preparation method and pharmaceutical application thereof

A compound and monocyclic technology, applied in the direction of active ingredients of hydroxyl compounds, organic chemistry, drug combination, etc., can solve the problems that the chemical composition has not been reported yet

Active Publication Date: 2018-03-27
FUDAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

It is mainly distributed in Jinxiu, Guangxi, Wuzhishan, Hainan, and northern Guangdong in China, on the steep slopes and valleys of mountain ridges with an altitude of 700-1600 meters (Zheng et al., In Flora of China; Science Press: Beijing, 1978; Vol.7, pp32-211), its chemical composition has not been reported yet

Method used

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  • Monocyclic diterpene compound cassipourol, and preparation method and pharmaceutical application thereof
  • Monocyclic diterpene compound cassipourol, and preparation method and pharmaceutical application thereof
  • Monocyclic diterpene compound cassipourol, and preparation method and pharmaceutical application thereof

Examples

Experimental program
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Embodiment 1

[0020] Embodiment 1: Preparation of diterpene compound cassipourol

[0021] Take 300 g of dried branches and leaves of Pinus chinensis, crush them, and extract them by cold soaking with 90% methanol at room temperature for 5 times, combine the extracts, concentrate under reduced pressure, and obtain about 30 g of extract. The extract was dispersed with water and extracted with petroleum ether (PE) and ethyl acetate (EtOAc) successively to obtain 7.0 g of the ethyl acetate part, which was subjected to 100-200 mesh silica gel column chromatography, and the mixture was separated by petroleum ether: ethyl acetate 30:1-0:1 and ethyl acetate:methanol 15:1-0:1 gradient elution to obtain 6 components (Fr.1-Fr.6). Component Fr.1 was further separated by semi-preparative HPLC and eluted isocratically with 90% methanol (flow rate: 3mL / min) to obtain the compound cassipourol (8.0mg, t R = 15.0 min). The NMR and physicochemical data of the compound cassipourol are as follows:

[0022] C...

Embodiment 2

[0023] Example 2: Determination of protein tyrosine phosphatase 1B inhibitory activity

[0024] Experimental method: The genetically recombined hGST-PTP1B-BL21E.coli human PTP1B engineering bacteria was constructed by using the method of molecular biology. The purified hGST-PTP1B recombinant protein can hydrolyze the phospholipid bond of the substrate para-Nitrophenyl Phosphate (pNPP), The obtained dephosphorylated product pNP has a strong light absorption at a wavelength of 405nm, so the change of light absorption at 405nm can be directly detected to observe the change of enzyme activity and the inhibition of the compound to the enzyme activity;

[0025] The percentage inhibition rate of the PTP1B enzyme activity was investigated when the concentration of the compound selected for the primary screening was 20 μg / ml, and the test results showed that the compound cassipourol inhibition rate was higher than 90%;

[0026] Further determination of IC 50 Value: The sample is disso...

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Abstract

The invention specifically relates to the vitamin A type monocyclic diterpene compound cassipourol and a preparation method thereof, belonging to the technical field of Chinese pharmaceutical manufacturing. The vitamin A type monocyclic diterpene compound cassipourol is extracted and separated from the branches and leaves of the Pinus plant Pinus kwangtungensis Chun ex Tsiang (Pinaceae), and has astructure as shown in a formula I which is described in the specification. In-vitro biological activity testing results prove that the compound has substantial inhibitory activity on protein-tyrosine-phosphatase 1B (PTP1B) and is used for preparing drugs for preventing, delaying or treating diabetes, obesity and complications thereof, and other PTP1B-mediated diseases.

Description

technical field [0001] The invention relates to the technical field of traditional Chinese medicine pharmacy, in particular to cassipourol, a vitamin A-type monocyclic diterpene compound extracted and separated from Pinus kwangtungensis, its preparation method and its use in pharmacy; especially for the preparation of protein tyramine Use in a medicament of an acid phosphatase 1B (PTP1B) inhibitor. 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 intracellular protein tyrosine residues, and is closely related to cell proliferation and various intracellular signal transduction processes ( Fischer et al,Science 1991,253:401-406); protein tyrosine phosphatase 1B (proteintyrosine phosphatase 1B, PTP1B) is widely distributed in a variety of human tissues, with a total length of about 50KDa, is the earliest purified and identified biological O...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C403/08A61K31/07A61P3/10A61P3/04
CPCC07C403/08
Inventor 胡金锋胡长玲熊娟杨国勋
Owner FUDAN UNIV
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