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Structure, preparation and biological activity of A type procyanidine biopolymer and acetone condensation compound

A technology of acetone condensate and proanthocyanidin, applied in the field of chemistry, can solve the problems of complex changes in structure, high irritation and toxicity, etc., and achieve the effects of strong free radical scavenging activity, low irritation and toxicity, and increased lipophilicity

Inactive Publication Date: 2014-11-05
INNER MONGOLIA UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the structure of proanthocyanidin polymers is susceptible to complex changes under the influence of reaction conditions. So far, proanthocyanidin polymers, including acetone condensates of dimers, have not been reported
In addition, the reported synthesis method of catechin acetone condensate uses p-toluenesulfonic acid, boron trifluoride ether or trimethylsilicone trifluoromethanesulfonate as catalysts, which are highly irritating and toxic

Method used

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  • Structure, preparation and biological activity of A type procyanidine biopolymer and acetone condensation compound
  • Structure, preparation and biological activity of A type procyanidine biopolymer and acetone condensation compound
  • Structure, preparation and biological activity of A type procyanidine biopolymer and acetone condensation compound

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preparation example Construction

[0014] The following specific embodiments will further describe the preparation method and activity assay method of the present invention in detail.

[0015] A preparation method and structure of proanthocyanidin acetone condensate, comprising the following steps:

[0016] 1) Preparation of Proanthocyanidin Acetone Condensate

[0017] Dissolve proanthocyanidins in acetone. After the mixture was cooled in ice water, a catalytic amount of concentrated sulfuric acid was added dropwise, and after reacting at room temperature, sodium carbonate was added to neutralize.

[0018] 2) Purification of Proanthocyanidin Acetone Condensate

[0019] The above reaction solution was diluted with ice water and subjected to reverse phase silica gel C18 chromatographic separation with water-methanol gradient elution to obtain proanthocyanidin acetone condensate.

Embodiment 1

[0020] Embodiment 1: the preparation of catechin acetone condensate

[0021] Catechin (60 mg, 0.2 mmol) was dissolved in acetone (1.4 ml). The mixture was cooled in ice water, and concentrated sulfuric acid (0.012 ml) was added dropwise. React at room temperature for 70 min. The reaction solution was neutralized to pH=5-6 by adding sodium carbonate (0.12 g). Add 20-fold dilution with ice water, use reversed-phase silica gel C18 column separation, and obtain 43 mg of compound from the elution fraction of 30% methanol 1 (Yield 65%). compound 1 The NMR spectrum data are consistent with the planar derivatives of catechin reported in the literature.

Embodiment 2

[0022] Embodiment 2: the preparation of proanthocyanidin A1 acetone condensate

[0023] Procyanidin A1 (95 mg, 0.16 mmol) (Zhang H, Yerigui, Yang Y, Ma C. Structures and antioxidant and intestinal disaccharidase inhibitory activities of A-typeproanthocyanidins from peanut skin. J Agric Food Chem , 2013, 61: 8814-8820) was dissolved in acetone (1.75 ml), the mixture was cooled in ice water, and concentrated sulfuric acid (0.012 ml) was added dropwise. React at room temperature for 70 min. The reaction solution was neutralized to pH=5-6 by adding sodium carbonate (0.12 g). Add 20 times of ice water to dilute, use reverse phase silica gel C18 chromatography column to separate, obtain 30.9 mg compound 2 , yield 33% ( Attachment 1 ). This compound is a new compound that has not been reported in the literature. Through comprehensive analysis of various spectral data ( Figure 3-7 ) determines the structure. compound 2 of 1 H and 13 CNMR data such as attached Figure 9...

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Abstract

The invention discloses a simple synthetic method of a procyanidine-acetone condensation compound and provides a novel procyanidine biopolymer and acetone condensation compound. The structure of the novel compound is analyzed through nuclear magnetic resonance and mass spectrum and optical spectrum technologies. The procyanidine biopolymer and acetone condensation compound has high activity of scavenging free radicals and the obviously enhanced activity of inhibiting alpha-glucosaccharase compared with that of procyanidine. The condensation compound can serve as antioxidants of foods, cosmetics and other products and also can serve as medicine or health-care product additives for inhibiting obesity and II type diabetes with the activity of inhibiting alpha-glucosaccharase.

Description

technical field [0001] The invention belongs to the field of chemical technology, and relates to the structure, preparation and activity of proanthocyanidin and acetone condensate, especially the preparation, structure, anti-oxidation activity and alafa-glucosidase activity of novel A-type proanthocyanidin acetone condensate. Background technique [0002] Proanthocyanidins are a class of compounds with strong biological activity, such as protecting the cardiovascular system, lowering blood sugar, and anticancer activities (Nagao, T., Hase, T., Tokimitsu, I. A green tea extract high in catechins reduces body fat and cardiovascular risks in humans. Obesity , 2007, 15: 1473-1483; Yang, C. S., Wang, X., Lu G., et al. C. Cancer prevention by tea: animal studies, molecular mechanisms and human relevance. Nat. Rev. Cancer , 2009, 9: 429-439; Katiyar, S.K., Mukhta, H. Tea antioxidants in cancer chemoprevention. J. Cell Biochem Suppl , 1997, 27: 59-67.). Such components are divi...

Claims

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Application Information

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IPC IPC(8): C07D493/22A61K31/353A61K8/49A61Q19/00A61P3/04A61P3/10A61P39/06A23L1/29A23L33/00
CPCC07D493/22
Inventor 马超美张慧文张玉
Owner INNER MONGOLIA UNIVERSITY
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