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Novel terpene compound with aldehyde group and preparation method and application thereof

A technology based on terpenoids and aldehyde groups, which can be used in medical preparations containing active ingredients, organic chemistry, drug combinations, etc., can solve problems that have not been seen before, and achieve low toxic and side effects, novel structure, and simple extraction and separation methods Effect

Active Publication Date: 2016-04-20
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The new terpenoids with aldehyde groups involved in the present invention have not yet seen relevant patents or literature reports on compounds and activities similar to this at home and abroad so far

Method used

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  • Novel terpene compound with aldehyde group and preparation method and application thereof
  • Novel terpene compound with aldehyde group and preparation method and application thereof
  • Novel terpene compound with aldehyde group and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1: the preparation of formula (I) compound:

[0029] Using 0.8kg of dried baobab fruit as raw material, according to the solid-liquid ratio of 1:8 (kg / L), reflux extraction with 70% ethanol three times, each time for one hour, concentrate to obtain 75g of extract-like ethanol extract, and concentrate to obtain The ethanol extract was suspended in water, extracted with ethyl acetate (3 times, 750ml / time), and the extracted part of the extract extracted with ethyl acetate was separated by medium and low pressure preparative chromatography (C18 packing, 50um) and separated using methanol-water ( Methanol volume content is 10%, 60%, 100%) gradient elution successively, wherein the elution part of 100% methanol is separated by semi-preparative high-performance liquid chromatography (AgilentXDB-C18reversed-phasecolumn-5μm, 250×10mm) again, with Acetonitrile-water (30:70 by volume) was eluted to obtain the compound of formula I (10 mg).

[0030] The obtained compou...

Embodiment 2

[0038] Embodiment 2: Formula (I) compound is to the growth inhibitory experiment of human breast cancer MDA-MB-231 cell in vitro: MDA-MB-231 cell monolayer is inoculated in containing mass concentration 2% glutamine, 1.5% sodium bicarbonate , 10% fetal bovine serum in RPMI-1640 culture medium. And added 100 units / ml of penicillin and 100 μg / ml of streptomycin. At a temperature of 37°C, CO 2 Cultured in a cell culture incubator at a concentration of 5%. Cells in the logarithmic growth phase were prepared as 1 × 10 4 Inoculate the concentration of cell / mL on a 96-well plate, 0.1mL per well, and then add medium containing different concentrations into the wells, each concentration has 3 parallel groups, add the same amount of solvent to the control group, and place in a 37°C carbon dioxide incubator Culture in medium for 72h, then centrifuge (1000rpm, 20min), discard the supernatant, add 0.20mg / mL MTT serum-free medium to each well, continue to culture at 37°C for 3h, centrifu...

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Abstract

The invention discloses a novel terpene compound with an aldehyde group and a preparation method and application thereof. The structure of the novel terpene compound with the aldehyde group is shown as a formula (I). The method for preparing the novel terpene compound with the aldehyde group comprises the following steps that 1, dry fruit of monkey bread is taken as a raw material, and an extract-shaped ethanol extract is obtained through ethanol extraction and concentration; 2, the extract-shaped ethanol extract is mixed and suspended in water and then extracted by ethyl acetate, and an organic phase is obtained; 3, The organic phase is separated through middle-low-pressure preparative chromatography, and gradient elution is performed with methanol-water containing 10%-100% of methanol by volume content, wherein the eluted portion of 100% methanol is eluted by acetonitrile-water with the volume ratio of 10:90-50:50 through semi-preparative efficient liquid-phase chromatographic separation, and then the novel terpene compound which has the aldehyde group and is shown in the formula (I) is obtained. The invention further provides the application of the compound (I) in preparation of antineoplastic drugs especially for human breast cancer MDA-MB-231 cells, and the certain inhibiting action is shown.

Description

(1) Technical field [0001] The invention belongs to the technical field of medicine, and relates to a new terpenoid compound with aldehyde group, its preparation method and its application in the preparation of antitumor drugs. (2) Background technology [0002] Baobab (Adansonia digitata) is native to tropical Africa. In addition to Africa, the Mediterranean, Atlantic and Indian Ocean islands, baobabs can also be seen in northern Australia. Cultivated in small quantities in tropical areas of Fujian, Guangdong, and Yunnan in China. The fruit of the African baobab has more than 50% more calcium than spinach, higher antioxidant content, and three times the vitamin C content of a single orange, so it is sometimes called a superfruit. It also has anti-inflammatory, antipyretic and antimalarial effects. [0003] There are few reports on terpenoids with aldehyde groups in the literature. S.J.Jacson et al. have reported that Norviburtinal has the effect of inhibiting melanoma, a...

Claims

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Application Information

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IPC IPC(8): C07D311/94A61K31/352A61P35/00
CPCC07D311/94
Inventor 李行诺颜继忠
Owner ZHEJIANG UNIV OF TECH
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