Sesquiterpenoids and preparation method and application thereof

A technology for sesquiterpenoids and compounds, applied in the field of caryophyllene-type new sesquiterpenoids and their preparation, can solve the problems of unsuitability for industrial production and preparation, low yield and the like

Inactive Publication Date: 2014-05-14
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the yields of (+)-pestalotiopsin A and (+)-pestalotiopsin C in Pestalotiopsis sp. are low, 1.2mg / L and 1.0mg / L respectively, and the fermentation needs to be cultured at low temperature (25°C) under dark conditions 21 to 46 days, and its production is also very accidental and unstable (Phytochemistry, 1997, 46: 313-319), not suitable for industrial production

Method used

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  • Sesquiterpenoids and preparation method and application thereof
  • Sesquiterpenoids and preparation method and application thereof
  • Sesquiterpenoids and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0043] Example 1: R is H and R is CH 3 Preparation of the compound of formula I:

[0044] Pick the spores of the fungus of the genus Ascotricha (Ascotricha sp.ZJ-M-5, the preservation number is CGMCC No.8278), and directly inoculate them into a liquid medium for 7 days on a shaker, wherein the medium is made of distilled water and contains sucrose 3%, NaNO 3 0.3%, KCl0.05%, FeSO 4 ·7H 2 O0.001%, K 2 HPO 4 0.1%, the culture temperature is 28°C, the shaker speed is 180 rpm, the fermentation broth is filtered to remove the mycelia, the filtrate is extracted 3 times with an equal volume of n-butanol, and the n-butanol extract is doubled for 200~ 300 mesh silica gel column chromatographic separation, gradient elution with a volume ratio (5:1-1:1) of petroleum ether-acetone mixed solvent, of which the volume ratio of 3:1 petroleum ether-acetone mixed solvent eluted part, After recrystallization, R is CH 3 The yield of the compound of formula I was 5 mg / L, and the fraction elu...

Embodiment 2

[0045] Embodiment 2: The growth inhibition test of the compound of formula I to human acute promyelocytic leukemia HL-60 cell line, human leukemia K562 cell line and mouse lymphocytic leukemia P388 cell line in vitro:

[0046] HL-60, K562 or P388 cells were cultured in RPMI1640 medium containing 10% heat-inactivated fetal bovine serum, 100 IU / mL penicillin, 100 μg / mL streptomycin and 1 mmol / L L-glutamine, and placed at 37 °C, 5% CO 2 Incubate in a saturated humidity incubator until the cells are 70%-80% confluent. Weigh trypan blue, add a small amount of distilled water to grind, add double distilled water to dilute to 4% storage concentration, filter with filter paper, and store at 4°C. When used, this stock solution was diluted to a working concentration of 0.4% with PBS. Take HL-60, K562 or P388 cells in 3×10 4 Cells / mL density, 1 mL per well was inoculated in a 24-well plate, and then added different concentrations of drugs (final concentrations were 0.1, 0.5, 1, 3, 10,...

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Abstract

The invention belongs to the technical field of medicines, and relates to two caryophyllene type sesquiterpenoids with anti-tumor activity, which are separated from Ascotricha sp., and a preparation method of the sesquiterpenoids. The structure of the sesquiterpenoids is described in the specification. The sesquiterpenoids related in the invention are novel in structure, and remarkable in anti-tumor activity in vitro, can be easily massively obtained by liquid fermentation and a simple and convenient extraction and separation method, and can be an active lead compound for developing a novel anti-leukemia medicine. The general formula is described in the specification, wherein R is H or CH3.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a new caryophyllene-type sesquiterpene compound with antitumor effect isolated from a fungus fermentation product of the genus Ascotricha sp.ZJ-M-5 and a preparation method thereof . Background technique [0002] Microorganisms can produce secondary metabolites with novel structures and diverse biological activities such as anti-tumor and anti-infection. Therefore, finding drug lead compounds from microorganisms has always been a hot spot in innovative drug research. Traditional microbial culture adopts the method of providing rich nutrients to promote its production. However, under this condition, the genes for the synthesis of secondary metabolites of most microorganisms are in a silent state, resulting in a small number and low content of secondary metabolites produced , and often produce many inactive substances such as fatty acids and cyclic dipeptides that interfere with ex...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/08A61K31/34A61P35/02C12P17/04C12R1/645
CPCC07D493/08C12P17/181
Inventor 李占林华会明王文静李丹毅
Owner SHENYANG PHARMA UNIVERSITY
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