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Diterpene compound, pharmaceutical composition for treatment or prevention of viral infectious diseases including same

A virus infection and compound technology, applied in health functional food and compositions for enhancing the production of interferon-γ, in the field of treatment or prevention of virus infection diseases, can solve the problems that the use of virus infection diseases has not been reported, and achieve treatment or The effect of preventing viral infection diseases

Inactive Publication Date: 2014-08-27
KOREA RES INST OF BIOSCIENCE & BIOTECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the use for the treatment of viral infection diseases has not been reported

Method used

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  • Diterpene compound, pharmaceutical composition for treatment or prevention of viral infectious diseases including same
  • Diterpene compound, pharmaceutical composition for treatment or prevention of viral infectious diseases including same
  • Diterpene compound, pharmaceutical composition for treatment or prevention of viral infectious diseases including same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] Example 1: Materials and methods

[0083] General Experimental Procedure

[0084] Optical rotation was determined using a Jasco P-2000 polarimeter (Jasco, Japan). UV data were obtained on a UV-VIS Spectrometer 2400 (Shimadzu Co. Ltd., Japan) and on a Varian UNITY 400 (Varian, Inc., Palo Alto). ), CA) using tetramethylsilane as the internal standard material to record NMR spectra. HRESIMS was performed on a Waters Q-Tof Premier spectrometer (Micromass UK Ltd., Manchester, UK). Silica gel (230-400 mesh, SiliCycle Inc., Quebec, Canada), RP-C18 (Cosmosil 75C18-PREP, Kyoto, Japan), and Sephadex LH-20 (25-100 μm, Sigma-Aldrich ), Steinheim (Steinheim, Germany) for column chromatography. In pre-coated Kiesel-gel 60F254 (0.25mm, Merck (Merck), Darmstadt, Germany) and Kiesel-gel 60RP-18F254s (0.25mm, Merck (Merck), Steinham ( Steinheim), Germany) for TLC.

[0085] plant material

[0086] The tung tree leaves used were collected in Seogwipo, Jejudo.

[0087] cell cu...

Embodiment 2

[0089] Embodiment 2: extraction and separation

[0090] 2.9 kg of air-dried tung tree leaves were ground and extracted three times with MeOH at room temperature to obtain 449.6 g of solid extract. Suspend the MeOH extract in H 2 O, then partitioned successively between n-hexane, EtOAc, and n-BuOH to afford 96.3 g, 53.9 g, and 85.9 g of residue, respectively. The hexane extract showed higher IFN-γ inducing activity compared to other solvent extracts. Therefore, the hexane extract was subjected to column chromatography (CC) on silica gel (230-400 mesh) with hexane / EtOAc (50:1 to 1:5) as eluent, and then again on silica gel using CHCl 3 / MeOH (10:1 to 1:1), resulting in 38 fractions (LH1 to LH38). The active fractions LH30 and LH31 were mixed together because they showed similarity on the TLC chromatograms, and then the resulting material was in RP-C18 (75C 18 -PREP) medium pressure liquid chromatography (MPLC) column chromatographic separation, using MeOH-H 2 A stepwise co...

Embodiment 3

[0091] Embodiment 3: compound identification

[0092] Compound 1 was isolated as a non-crystalline solid. 673.3953 [M-H] by High Resolution Electron Spray Ion Mass Spectrometry (HRESIMS) - Molecular ion peak whose molecular formula was identified as C 38 h 58 o 10 ( figure 1 ). Compound 1 1 H, 13 C and DEPT spectra show 2 doublets, 4 carbonyl groups, 5 methyl groups, 2 oxymethylene groups, 5 methine groups and 4 quaternary carbon atoms (3 oxidized) ( Figure 2 to Figure 4 ). from 1 δ of H spectrum H The large broad peak of 1.24 indicates the presence of long carbon chain units in this compound. In the HMBC spectrum, the olefin proton δ at 6.86(H-5) H Exhibited with δ C Oxygenated carbon atoms and δ at 61.3 (C-20) C The two carbonyls at 205.1(C-3) and 202.6(C-7) are related, and the other alkene proton δ at 7.61(H-1) H Shows methyl and carbonyl resonances at 10.6 (C-19) and 205.1 (C-3). This indicates the presence of two α,β-unsaturated ketone skeletons in this...

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PUM

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Abstract

The present invention relates to a fluidic phorbol type diterpene compound, a pharmaceutical composition for treatment or prevention of viral infectious diseases including the same, a health functional food for prevention or improvement of the viral infectious diseases, and a composition for enhanced production of interferon-gamma. Furthermore, the present invention relates to a method for prevention or treatment of the viral infectious diseases including a step of injecting the composition into an entity having an occurrence or risk of the viral infectious diseases with a therapeutically effective dose.

Description

technical field [0001] The present invention relates to a diterpene compound obtained from Aleurites fordii, and a pharmaceutical composition containing the diterpene compound for treating or preventing viral infection diseases, a health functional food and a medicine for preventing or improving viral infection diseases Compositions for enhancing interferon-gamma production. In addition, the present invention relates to a method for treating or preventing a viral infection disease, comprising administering a therapeutically effective dose of the composition to a patient who has a viral infection disease or is at risk thereof. Background technique [0002] The production of interferon-γ (IFN-γ) in immune cells is an important step in early self-defense against viral and bacterial infections and tumor control (Biron, C.A. et al., Annu.Rev.Immunol. 1999, 17 , 189-220). IFN-γ is produced in natural killer cells (NK) and natural killer T cells (NKT), which generally serve as ef...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/738C07C69/013A61K31/015A23L33/00
CPCA23L1/29A23V2002/00C07C69/753A61K31/215C07C69/33C07C2103/40C07C2603/40A23L33/00A61P31/12C07C69/738A61K31/015
Inventor 吴世湸金载和裴艺花李炯圭姜虎范金斗英安璄燮池多情
Owner KOREA RES INST OF BIOSCIENCE & BIOTECHNOLOGY
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