(Z,E)-5-OH-3-(phenyl-derivative-methylene)-dihydroflavone-7-O-glucoside and preparation and application thereof

A dihydroflavonoid, -5-OH-3- technology, applied in the fields of chemistry, cosmetics and medicine, can solve the problems of application limitation and unstable properties, and achieve the effects of single reaction site, easy purification and mild reaction conditions

Active Publication Date: 2017-05-10
YICHUN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

And epigallocatechin gallate (EGCG) and epicatechin gallate (ECG) among the catechols with strong activity are unstable because of the ester bond in the molecule, so the application is limited

Method used

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  • (Z,E)-5-OH-3-(phenyl-derivative-methylene)-dihydroflavone-7-O-glucoside and preparation and application thereof
  • (Z,E)-5-OH-3-(phenyl-derivative-methylene)-dihydroflavone-7-O-glucoside and preparation and application thereof
  • (Z,E)-5-OH-3-(phenyl-derivative-methylene)-dihydroflavone-7-O-glucoside and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1: Preparation of 3-(4-hydroxyphenylmethine)-hesperidin:

[0040]Weigh 1.0 g of hesperidin with a content of 95%, 0.20 g of p-hydroxybenzaldehyde, add 137 μL of DMSO 3.0 mL tetrahydropyrrole, 100 μL of glacial acetic acid, stir and react at 70 ° C for 24 h, add silica gel to mix the sample, wash with chloroform-methanol gradient After removal, 775 mg of yellow powder was obtained, which was 3-(4-hydroxybenzylmethine)-hesperidin (cpd 1). 1 H NMR (400 MHz, DMSO) δ12.63 (d, 1H: 5-OH), 10.27 (s, 1H: 3'-OH), 9.17 (s, 1H: 15-OH), [8.32+7.94 (d ,1H:11-H)], 7.27-7.31(2H:13-H+17-H), 6.75-7.00(m,5H:14-H+16-H+2'-H+5'-H+ 6'-H), 6.66 (d, 1H: 2-H), 6.05-6.12 (dd, J=2.0, 2H: H-6+H-8), 3.74 (s, 3H: 4'-OCH 3 ), 5.36 (1H: Gly-1"), 4.90 (1H: Rha-1"'), 1.10 (dd,3H: Rha-6"'); 13 C NMR (100 MHz, DMSO-d6) δ185.81 (d, C-4), 165.97 (d, C-7), 164.34 (C-9), 160.46 (C-5), 148.55 (C-4' ), 147.75(C-3'), 133.42(C-1'), 130.38(C-3), 118.93(C-6'), 115.01(C-2'), 112.85(C-5'), 103.94 (C-10...

Embodiment 2

[0042] Example 2: Preparation of 3-(3,4-hydroxyphenylmethine)-hesperidin:

[0043] Weigh 1.5 g of hesperidin with a content of 95%, add 200 μL of tetrahydropyrrole and 4.0 mL of DMSO to dissolve, add 150 μL of glacial acetic acid, stir and react at 60°C for 3 h, then add 0.25 g of 3,4-hydroxybenzaldehyde in portions, The addition was completed within 8 hours, and the reaction was continued for 3 hours. The sample was mixed with silica gel and eluted with a gradient of chloroform-methanol to obtain 803 mg of yellow powder, which was 3-(3,4-hydroxybenzylmethine)-hesperidin (cpd 2). 1 H NMR (400 MHz, DMSO) δ12.63 (d, 1H: 5-OH), 9.17 (s, 1H: 3'-OH), [8.31+7.85 (d, 1H: 11-H)], 6.99– 6.70(m,6H:2'-H+5'-H+6'-H+13-H+16-H+17-H), 6.56(d,1H:2-H), 6.09(d,2H : 6-H+8-H), 5.37(s, 1H: 2-H), 3.74(s, 3H: 4'-OCH 3 ); 5.37 (s, 1H: Gly-1"'-H), 4.95 (d, 1H: Rha-1"'-H), 1.10 (d, 3H: Rha-6"'). 13 C NMR (100 MHz, DMSO-d6) δ185.79 (C-4), 165.92 (C-7), 164.34 (C-9), 160.20 (C-5), 149.21 (C-4'), 148.51...

Embodiment 3

[0045] Example 3: Preparation of 3-(3,4-hydroxyphenylmethine)-naringin

[0046] Weigh 1.5 g of naringin with a content of 98%, add 200 μL of tetrahydropyrrole and 4.0 mL of DMSO to dissolve, add 150 μL of glacial acetic acid, stir and react at 60°C for 3 hours, then add 0.30 g of 3,4-hydroxybenzaldehyde in portions, The addition was completed within 8 hours, and the reaction was continued for 3 hours. The sample was mixed with silica gel and eluted with a gradient of chloroform-methanol to obtain 845 mg of yellow powder, which was 3-(3,4-hydroxybenzylmethine)-naringin (cpd 3). 1H NMR (400 MHz, DMSO) δ12.70(d,1H:5-OH), 9.65(br,1H:15-OH), 9.13(br,1H:14-OH), [8.31+7.85(d, 1H: 11-H)], 7.17-7.30 (2H: 13-H+17-H), 6.68-6.90 (m, 5H: 2'-H+3'-H+5'-H+6'-H +16-H), 6.50-6.65(d,1H:2-H), 5.32(1H:2-H); 5.0-5.20(2H:Gly-1"'-H+Rha-1"'-H) 1.17 (d,3H:Rha-6"'). 13 C NMR (100 MHz, DMSO-d6) δ185.76 (C-4), 165.27 (C-7), 164.14 (C-9), 160.12 (C-5), 158.24 (C-4'), 133.48 C -3), 129.23(C-1'), 128.93(...

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Abstract

The invention provides (Z,E)-5-OH-3-(phenyl-derivative-methylene)-dihydroflavone-7-O-glucoside and a preparation method and application thereof; a structural general formula of the (Z,E)-5-OH-3-(phenyl-derivative-methylene)-dihydroflavone-7-O-glucoside is shown as in formula (I) shown in the description, wherein R1 may be -glucose, -[[6-O-(6-deoxy-alpha-L0mannopyranosyl)-beta-D-glucopyranosyl]oxy], -[[2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy], or 7-beta-D-glucopyranose acid, R2 may be -H, -OH, or -OCH3, R3 may be single group or multiple groups of -H, -OH, -OCH3, -O-glucose, -O-glucuronic, -O-neohesperidose, -F, -Cl, and -Br, and R4 may be single group or multiple groups of -H, -OH, -OCH3, -Cl, -Br, -NO2, -COOH, and methylenedioxy. Such compound has good antioxidant, anti-inflammatory, antibacterial, antivirus, anticancer and cardiovascular protection effects, and is widely applicable to the industries, such as food, cosmetics, and drugs.

Description

[0001] Technical field: [0002] The invention belongs to the fields of chemistry, cosmetics and medicine, and relates to a flavonoid compound and its preparation method and application, especially a (Z, E)5-OH-3-(phenyl derivative-methine)- Dihydroflavone-7-O-glucoside and its preparation method and application. [0003] Background technique: [0004] There are many kinds of flavonoids in nature, the content is abundant, the extraction and preparation process is simple, and the price is low. Due to the secondary metabolites of natural flavonoids plant enzymes, they mostly contain phenolic hydroxyl groups. Due to the uneven distribution of phenolic hydroxyl groups, which occupy two benzene rings, no o-diphenol OH is formed, and the antioxidant effect is weak. Representative compounds such as hesperidin, naringin, neohesperidin, and diosmin , Rhodorin, apigenin, hesperetin, naringenin, methyl hesperidin. Even if it contains o-diphenolic hydroxyl groups, due to the good coplan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/07C07H1/00A61K31/7048A61P29/00A61P39/06A61P31/04A61P31/10A61P31/12A61P35/00A61P9/00A61K8/60A61Q19/08A23L33/10
CPCA23V2002/00A61K8/602A61Q19/08C07H1/00C07H17/07A23V2200/32A23V2200/326A23V2200/308
Inventor 申秀丽郭孟萍闻永举
Owner YICHUN UNIVERSITY
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