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Curcumolide-like derivatives with antitumor activity and preparation method thereof

A technology of curcuma and lactone is applied in the field of curcumoid derivatives with anti-tumor activity and preparation thereof, and can solve the problems of low water solubility and the like

Inactive Publication Date: 2015-09-09
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

(Hou et al., 2010) but the chemical structure of curcumadione determines its low water solubility, the characteristics of being easily soluble in organic solvents such as ethanol, ether, chloroform, acetone, etc., but insoluble in water, which limits its application

Method used

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  • Curcumolide-like derivatives with antitumor activity and preparation method thereof
  • Curcumolide-like derivatives with antitumor activity and preparation method thereof
  • Curcumolide-like derivatives with antitumor activity and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Embodiment 1: Preparation of 3α-hydroxycurcumolactone by biotransformation method:

[0059] 1: culture medium

[0060] A: Incline medium

[0061] Potato 20g, glucose 2g, agar 2g, distilled water 100mL.

[0062] B: liquid medium

[0063] Peptone 5g, glucose 15g, sucrose 15g, K 2 HPO 4 1.0g, KCl 0.5g, MgSO 4 0.5g, FeSO 4 ·7H 2 O0.01g, distilled water 1000mL, pH 7.0.

[0064] All the above media were steam sterilized at 115°C for 30 min.

[0065] 2: The process of biotransformation

[0066] Two-stage fermentation method (two-stage process):

[0067] A: The first stage of fermentation culture: inoculate the strain Aspergillus niger AS 3.739 on the slant of solid slant medium, culture at 28°C for 7 days, after producing abundant conidia, add 5mL sterile liquid medium to prepare spore suspension. The spore suspension was transferred into a 250 mL Erlenmeyer flask containing 50 mL of liquid medium, and cultured with shaking at 200 rpm at 28° C. for 72 hours to obtai...

Embodiment 2

[0073]Embodiment 2: the product of chemical transformation, then carry out biotransformation method to prepare 9,10-dihydroxylated curcumolactone:

[0074] Add 1% volumetric concentrated hydrochloric acid to 20 mL of chloroform, then add 20 mg of curcumadione, mix well and place at 20° C. for 24 hours to react. The solvent was removed by drying under reduced pressure to obtain a crude product, which was separated by column chromatography and eluted with a mixed solvent of n-hexane ethyl acetate, and concentrated under reduced pressure to obtain 15 mg of curcumolactone. By the biotransformation method described in Example 1, the product curcumolactone (dissolved in ethanol, sterilized through a sterile 0.22 μm filter) in step 3 is used as a substrate, with a final concentration of 0.1g / L, and then passed through the column Chromatography, eluting with a mixed solvent of n-hexane ethyl acetate, separated the converted product.

[0075] Structural identification of the transform...

Embodiment 3

[0077] Embodiment 3: the intermediate product of biotransformation, then carry out chemical transformation and prepare 3α-hydroxycurcumolactone:

[0078] 60 mg of curedione was converted by the biotransformation method in Example 1, and 18 mg of the intermediate product 3α-hydroxycuredione was isolated, which was added to 20 mL of chloroform containing 1% by volume concentrated hydrochloric acid, and reacted at 20° C. for 24 hours , dried under reduced pressure to remove the solvent, separated and purified by silica gel column chromatography to obtain white needle crystals. Structural identification of the product:

[0079] TOF-MS m / z: 275[M+Na] + , suggesting that the molecular weight is 252, consistent with the molecular weight of the substrate, and the molecular formula is C 15 h 24 o 3 . The NMR data were consistent with the NMR data of product 1, and the product 3 was identified as 3α-hydroxycurcumolactone.

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Abstract

The invention relates to the field of medicine. Curcumalactone derivatives with antitumor activity and the process for their preparation are disclosed. The said curcumalactone derivatives and their oxidized derivatives have a spironolactone structure as in formula (I). The preparation process for these compounds are also provided, wherein biotransformation is used. The intermediates of the process as in formula (II) are disclosed. The present compounds have antitumor activity.

Description

Technical field: [0001] The present invention relates to curcumolide derivatives with anti-tumor activity and a preparation method thereof. The preparation method relates to a new method for structural modification of sesquiterpenoids, that is, using biotransformation or chemical transformation or both The combination of these compounds can be used to obtain new compounds, and the structural modification involves the transformation of the core structure from gemane type to spironolactone type. Background technique: [0002] The traditional Chinese medicine Zedoary is the dried rhizome of Curcumaphaeocaulis Val., Curcumakwangsiensis S.G.Lee et C.F.Liang and Curcuma wenyujin Y H.Chen et C.ling. Zedoary oil is the volatile oil component extracted from the traditional Chinese medicine Zedoary. Zedoary oil has anti-tumor (Sun et al., 2009; Wu et al., 2000), anti-oxidation (Loc et al., 2008; Mau et al., 2003 ), antibacterial (Lai et al., 2004; Wilson et al., 2005) and other pharm...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/94C07D407/04C07D493/10C12P17/04C12P17/16C12P17/18A61K31/365A61P35/00
CPCC12P17/162C12P7/26C12P17/04A61P35/00
Inventor 贾娴游松陈奕南秦斌马小双吴英良万晓辉徐慰倬银月
Owner SHENYANG PHARMA UNIVERSITY
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