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(Synonyms: 2-(3,4-二羟基苯基)-2-((2-(3,4-二羟基苯基)-5,7-二氢色满-3-基)氧基)苯并二氢吡喃-3,4,5,7-四醇) 目录号 : GC32676 复制 一键复制产品信息

Proanthocyanidins是黄酮类生物合成途径的终产物,是单体黄烷-3-醇的低聚物或聚合物。Proanthocyanidins是具有多种药理特性的缩合单宁。

Proanthocyanidins Chemical Structure

Cas No.:20347-71-1

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Description

Proanthocyanidins are oligo- or polymers of monomeric flavan-3-ols produced as end products of the flavonoid biosynthetic pathway. Proanthocyanidins are condensed tannins with various pharmacological properties [1,2]. Proanthocyanidins are commonly used in research related to antioxidant, anticancer, antidiabetic, neuroprotective, and antimicrobial research.

In vitro, Proanthocyanidins (50μg/mL; 12h) reduced H2O2 level in 0.50mM H2O2-treated macrophage J774A.1 cells and neuronal PC-12 cells by 36% and 50%, respectively [3]. Proanthocyanidins (2.5, 5.0, 10.0, and 20.0μg/mL; 12h, 24h, and 48h) substantially reduced H2O2-induced cell apoptosis, oxidative stress and activation and translocation of NFκβ/p65 in cultured HLEB-3 cells [4].

In vivo, Proanthocyanidins (10mg/kg; oral; 6 weeks) reduced the serum concentrations of triglycerides (TG), total cholesterol (TC), and nonesterified fatty acids (NEFA), and reduced the serum level of glucose and glycosylated protein in a db/db type 2 diabetes model [5].

References:
[1]. Rauf, Abdur, et al. "Proanthocyanidins: A comprehensive review." Biomedicine & Pharmacotherapy 116 (2019): 108999.
[2]. Mizuno, Mirei, et al. "Synthesis and antioxidant activity of a procyanidin B3 analogue." Bioorganic & medicinal chemistry letters 27.4 (2017): 1041-1044.
[3]. Bagchi, D., et al. "Hydrogen peroxide‐induced modulation of intracellular oxidized states in cultured macrophage J774A. 1 and neuroactive PC‐12 cells, and protection by a novel grape seed proanthocyanidin extract." Phytotherapy Research: An International Journal Devoted to Pharmacological and Toxicological Evaluation of Natural Product Derivatives 12.8 (1998): 568-571.
[4]. Jia, Zhiyan, et al. "Grape seed proanthocyanidin extract protects human lens epithelial cells from oxidative stress via reducing NF-кB and MAPK protein expression." Molecular vision 17 (2011): 210.
[5]. Lee, Young A., Eun Ju Cho, and Takako Yokozawa. "Effects of proanthocyanidin preparations on hyperlipidemia and other biomarkers in mouse model of type 2 diabetes." Journal of Agricultural and Food Chemistry 56.17 (2008): 7781-7789.

Proanthocyanidins是黄酮类生物合成途径的终产物,是单体黄烷-3-醇的低聚物或聚合物。Proanthocyanidins是具有多种药理特性的缩合单宁[1,2]。Proanthocyanidins常用于抗氧化、抗癌、抗糖尿病、神经保护和抗微生物等研究领域。

在体外,Proanthocyanidins(50μg/mL;12h)可使0.50mM H2O2处理的巨噬细胞J774A.1和神经细胞PC-12中的H2O2水平分别降低36%和50%[3]。Proanthocyanidins (2.5, 5.0, 10.0, and 20.0μg/mL; 12h, 24h, and 48h)能显著降低过氧化氢诱导的HLEB-3细胞凋亡、氧化应激以及NFκβ/p65的活化和转位[4]

在体内,Proanthocyanidins(10mg/kg;口服;6周)可降低db/db型2型糖尿病模型小鼠血清中甘油三酯(TG)、总胆固醇(TC)和非酯化脂肪酸(NEFA)的浓度,并降低血清葡萄糖和糖化蛋白水平[5]

实验参考方法

Cell experiment [1]:

Cell lines

Macrophage J774A.1 cells and neuronal PC-12 cells

Preparation Method

Oxidative stress in these cells was induced by incubating with 0.50mM hydrogen peroxide for 24h. The concentration-dependent protective ability of Proanthocyanidins was assessed by pre-incubating the cells with 50 and 100μg/mL of Proanthocyanidins for 12h. The overall intracellular oxidized states of cells before and after exposure to hydrogen peroxide and/or selected concentrations of Proanthocyanidins were assessed at an excitation wavelength of 513nm using a Meridian ACS 570 Scanning Confocal Laser Microscope and 2,7-dichlorofluorescein diacetate (DCFD) as the fluorescent probe.

Reaction Conditions

50 and 100μg/mL; 12h.

Applications

H2O2-induced 5.8 and 4.5-fold increases in fluorescence intensity in J774A.1 and PC12 cells, while 50μg/mL Proanthocyanidins decreased H2O2-induced fluorescence intensity by 36% and 50%, respectively.
Animal experiment [2]:

Animal models

Male, 5-wk-old, C57BL/Ksj-db/db mice

Preparation Method

Male, 5-wk-old, C57BL/Ksj-db/db mice and their age-matched nondiabetic m/m littermates were kept in a plastic-bottomed cage and exposed to a 12h light/dark cycle. The room temperature (about 25°C) and humidity (about 60%) were controlled automatically. The mice were allowed free access to laboratory pellet chow (comprising 24.0% protein, 3.5% lipids, and 60.5% carbohydrate), and water was given ad libitum. After 10 days of adaptation, glucose and total cholesterol (TC) levels of blood taken from the tail vein were measured. Animals were divided into two groups (13∼14 mice/group, 3∼4 mice/cage). The db/db control group was given water (vehicle), while the other group wes administered Proanthocyanidins orally at a dose of 10mg/(kg body weight·day).

Dosage form

10mg/kg; oral; 6 weeks.

Applications

Proanthocyanidins reduced the serum concentrations of triglycerides (TG), total cholesterol (TC), and nonesterified fatty acids (NEFA).

References:
[1]. Bagchi, D., et al. "Hydrogen peroxide‐induced modulation of intracellular oxidized states in cultured macrophage J774A. 1 and neuroactive PC‐12 cells, and protection by a novel grape seed proanthocyanidin extract." Phytotherapy Research: An International Journal Devoted to Pharmacological and Toxicological Evaluation of Natural Product Derivatives 12.8 (1998): 568-571.
[2]. Lee, Young A., Eun Ju Cho, and Takako Yokozawa. "Effects of proanthocyanidin preparations on hyperlipidemia and other biomarkers in mouse model of type 2 diabetes." Journal of Agricultural and Food Chemistry 56.17 (2008): 7781-7789.

化学性质

Cas No. 20347-71-1 SDF
别名 2-(3,4-二羟基苯基)-2-((2-(3,4-二羟基苯基)-5,7-二氢色满-3-基)氧基)苯并二氢吡喃-3,4,5,7-四醇
Canonical SMILES OC1C(OC2C(C3=CC=C(O)C(O)=C3)OC4=CC(O)=CC(O)=C4C2)(C5=CC=C(O)C(O)=C5)OC6=CC(O)=CC(O)=C6C1O
分子式 C30H26O13 分子量 594.52
溶解度 Water: 5 mg/mL (8.41 mM; ultrasonic and adjust pH to 11 with Na2CO3) 储存条件 Store at -20°C
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储备液的保存方式和期限:-80°C 储存时,请在 6 个月内使用,-20°C 储存时,请在 1 个月内使用。
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1 mg 5 mg 10 mg
1 mM 1.682 mL 8.4101 mL 16.8203 mL
5 mM 336.4 μL 1.682 mL 3.3641 mL
10 mM 168.2 μL 841 μL 1.682 mL
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