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Fructose glycosylated curcumin as well as preparation method and application thereof

A technology of curcumin and glycosylation, which is applied in the direction of medical preparations containing active ingredients, organic chemistry, sugar derivatives, etc., to achieve the effect of industrialization advantages, low production costs, and good bioavailability

Pending Publication Date: 2022-07-26
上海龙殷生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, curcumin derivatized by glucose monosaccharide groups, that is, curcumin-4'-O-β-D-glucoside (Curcumin-4'-O-β-D-glucoside,) has a solubility of only 7.0× 10-3μmol / mL

Method used

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  • Fructose glycosylated curcumin as well as preparation method and application thereof
  • Fructose glycosylated curcumin as well as preparation method and application thereof
  • Fructose glycosylated curcumin as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1 Heterologous expression and purification of fructansucrase.

[0032] The fructansucrase LS used in this example is from Clavibactermichiganensis, and the nucleic acid and protein sequences of the enzyme are from the public NCBI gene database (https: / / www.ncbi.nlm.nih .gov / ), the nucleic acid and protein sequences of the enzyme can be obtained from the NCBI database with reference number (NCBI Reference Sequence: WP_011931834.1). According to the codon preference of Escherichia coli, it was codon-optimized, and a 6X His tag sequence was added to the end of its sequence, and the final sequence was sequence 1. The codon-optimized fructansucrase LS gene sequence was synthesized and subcloned into the E. coli expression vector pET30a(+) (Suzhou Jinweizhi Company, pET30a(+) is a published commercial E. coli expression vector). The recombinant plasmid pET30a-LS carrying the fructansucrase gene was transformed into E. coli BL21(DE3) host and screened overnight on LB-...

Embodiment 2

[0036] Example 2 Enzymatic fructoglycosylation of curcumin.

[0037] Taking the fructansucrase prepared in Example 1 as a catalyst, using curcumin (CAS: 458-37-7, purity 98%, Dingrui Chemical (Shanghai) Co., Ltd.) as a glycosyl acceptor, and using sucrose as a sugar The alkylation donor undergoes an enzymatic glycosylation reaction. In addition, several

[0038] The enzyme-catalyzed reaction conditions are as follows: 0.2M citrate sodium acetate buffer (pH 4.5-5.5) or 0.2M PBS (pH6.5-8.5) is used as the catalytic solvent system. The reaction was added with 0.5g curcumin (1.36mmol) as a glycosyl acceptor, 10g sucrose as a glycosyl donor, 1g fructansucrase, and 1g sophorolipid as a solubilizer to dissolve and disperse in a 100mL catalytic dissolving system, and The reaction was carried out in a constant temperature shaking water bath at 35°C for 6h.

[0039] The content of glycosylated curcumin in the catalytic solution after the reaction was analyzed by HPLC-MS / MS. The chro...

Embodiment 3

[0047] Example 3 Fructose glycosylated curcumin solubility

[0048] The reaction solution obtained by the reaction after proportional amplification of the fructose glycosylated curcumin sample preparation conditions described in Example 2 was used to prepare fructose glycosylated curcumin. Fructose glycosylated curcumin was separated and purified by Isolera rapid preparative chromatography, and the separation was carried out using SNAP KP-Sil (340 g) column. The separation process is to evenly add a sufficient amount of reaction solution to the sample cup, then place it in a vacuum drying oven at 60°C to evaporate the solvent, and then directly install the sample cup instead of the flow guide on the SNAP KP-Sil chromatographic column. Then proceed according to the chromatographic elution conditions: the elution flow rate is 8mL / min, the elution mobile phase is a binary mixture of methanol-0.1% acetic acid aqueous solution, and the elution gradient is 0-30min: methanol 15%→30...

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Abstract

The invention discloses curcumin subjected to fructose glycosylation, a preparation method and application, levan sucrase is used as a catalyst, curcumin is used as a glycosylation acceptor, cane sugar is used as a glycosylation donor to carry out enzymatic glycosylation reaction, the curcumin subjected to fructose glycosylation is obtained, the solubility of the curcumin subjected to fructose glycosylation is far higher than that of the curcumin subjected to glucose glycosylation, and the curcumin subjected to fructose glycosylation can be used for preparing the curcumin subjected to fructose glycosylation. Therefore, the better bioavailability is achieved.

Description

technical field [0001] The invention relates to glycosylated curcumin, in particular to a fructose glycosylated curcumin, a preparation method and application. Background technique [0002] Curcuminoids are phenolic pigments extracted from the roots and stems of the traditional Chinese medicine turmeric, mainly including curcumin, demethoxycurcumin and demethoxycurcumin. (bisdemethoxycurcumin), mainly curcumin. [0003] Curcumin compounds are important active components of traditional Chinese medicine turmeric, which have been found to have anti-cancer, anti-inflammatory, antioxidant, hypolipidemic, anti-atherosclerotic, anti-depressant, anti-Parkinson's disease and other pharmacological activities. , and non-toxic, no side effects, a wide range of applications. [0004] However, curcumin has poor water-solubility and fat-solubility, and its structure is unstable and easily degraded in the body, resulting in its low bioavailability. derivatization method. [0005] Patent...

Claims

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Application Information

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IPC IPC(8): C12P19/44C07H15/203A61K31/7034A61P35/00A61P29/00A61P25/28
CPCC12P19/44C07H15/203A61K31/7034A61P35/00A61P29/00A61P25/28Y02A50/30
Inventor 张鹏李庆廷强耀锋樊冰
Owner 上海龙殷生物科技有限公司
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