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Pelargonidin
Food & Function · 2020 ·Vol. 11 ·期 6 ·5156-5165 · IF 4.171

Pelargonidin ameliorates CCl4-induced liver fibrosis by suppressing the ROS-NLRP3-IL-1β axis via activating the Nrf2 pathway

Yu-Sheng Shi,Xiao-Xing Li,Hao-Tian Li,Yan Zhang

Liver fibrosis is a histological change that often occurs due to hepatic stellate cell (HSC) activation and excessive formation of an extracellular matrix in the liver. Pelargonidin (PEL) is a natural anthocyanidin existing in blueberries, berries, strawberries, and red radishes and has been demonstrated to possess health beneficial effects. Herein, we investigated the effect of PEL on liver fibrosis induced by CCl4 and hepatic stellate cells induced by transforming growth factor-β (TGF-β). We found that PEL administration prevented liver injury and liver fibrosis induced by CCl4 in a dose-dependent manner. Further data revealed that PEL increased liver nuclear factor E2-related factor 2 (Nrf2) and reduced liver oxidative stress and the expression levels of NLRP3, caspase-1 and IL-1β. In TGF-β-challenged HSCs (LX-2 cells), PEL effectively inhibited the LX-2 cell activation. In addition, the anti-fibrosis effects of PEL in LX-2 cells were abolished by Nrf2 knockdown. In summary, our study demonstrated that PEL ameliorated CCl4-induced liver fibrosis and HSC activation induced by TGF-β. The possible molecular mechanisms of PEL in liver fibrosis may be attributed to its suppression of ROS-NLRP3-IL-1β signaling by Nrf2 activation.

CAS / MDL: 56-23-5 134-04-3
研究领域: 药理学 · 肝病学 · 分子生物学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES · 2017 · IF 2.603

An effective method for preparation of high-purity pelargonidin-3-O-glucoside from strawberry and its protective effect on cellular oxidative stress

Yang Xu,Dongwen Hu,Yuting Li,Chongde Sun,Wei Chen

Accumulating evidence indicates that consumption of berries may exert beneficial effects against oxidative stress mediated diseases. Pelargonidin -3-O- glucoside (Pg3G), a bioactive ingredient in strawberry, has been reported to possess a potent antioxidant capacity. This study was therefore designed to develop an effective method to prepare pure Pg3G from strawberry and investigate its protective effect against H 2 O 2 -induced oxidative stress. According to our results, Pg3G occupied 85.55% of total anthocyanin content in strawberry. 240   mg of Pg3G with the purity of 97.26% was finally isolated from 320   g of strawberry lyophilized powder (SLP) by combination of AB-8 macroporous resin and high-speed counter-current chromatography (HSCCC) technologies. Further study unveiled that Pg3G significantly inhibited H 2 O 2 -induced ROS generation, GSH depletion and mitochondrial dysfunction, thereby ameliorating H 2 O 2 -induced oxidative stress. Overall, this study suggests that pelargonidin -3-O- glucoside can be used as a natural bioactive agent to prevent cellular oxidative stress.

研究领域: 食品科学 · 生物化学 · 药理学
✓ 已验证 DOI PubMed 高影响因子
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JOURNAL OF FOOD BIOCHEMISTRY · 2022 ·Vol. 46 ·期 8 ·e14192 · IF 3.654

Antioxidant activity of delphinidin and pelargonidin: Theory and practice

Hongan Li,Chengyue Zhang,Zeyuan Deng,Bing Zhang,Hongyan Li

The quantum chemical density functional theory and in vitro chemical-based antioxidant assays were used to research the reaction mechanism of delphinidin/pelargonidin with free radicals including superoxide anion radicals (O 2 − ∙) and hydroperoxide radicals (OOH∙). The geometric configuration, bond dissociation energy, PCM (polarizable continuum model) solvent model reaction enthalpy changes were studied to explain the transition states, and the reaction enthalpy change value was calculated to determine the active site. From the results of spatial configuration, delphinidin showed a stronger conjugation effect than that of pelargonidin. The dihedral angle between the three rings of delphinidin was almost 180°, and the angle between the B and C rings was only −2.81868°. Both coplanar and antioxidant activity of delphinidin was better than pelargonidin. The consequences of reaction enthalpy change in PCM were consistent with the bond dissociation energy. The phenolic hydroxyl bond dissociation energy of delphinidin was slightly smaller than that of pelargonidin. Moreover, the C4' site of delphinidin and the C3 site of pelargonidin were the active sites for scavenging free radicals. The free radical scavenging ability of delphinidin was marginally higher than that of pelargonidin. On the other hand, in vitro antioxidant results proved the scavenging ability of delphinidin and pelargonidin on superoxide anions, DPPH, and ABTS ∙+ free radicals. It was shown that the chemical-based antioxidant activity was consistent with the theoretical calculation results, with delphinidin showing greater antioxidant activity. These results could explain the antioxidant mechanism of delphinidin/pelargonidin in scavenging free radicals from chemical reactions. Practical applications This manuscript explained the antioxidant mechanism of delphinidin/pelargonidin in scavenging free radicals through the analysis of the geometric configuration of delphinidin/pelargonidin and the theoretical calculation of the reaction transition state. It could also speculate on the possible reaction sites, and provide a basis for judging how to efficiently select antioxidants with great antioxidant activity.

CAS / MDL: 1898-66-4
研究领域: 化学 · 生物化学 · 分子生物学 · 药理学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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FOOD CHEMISTRY · 2022 · IF 9.231

Improvement of stability and lipophilicity of pelargonidin-3-glucoside by enzymatic acylation with aliphatic dicarboxylic acid

Jiahong Xie,Xin Hao,Yiqiu Shang,Wei Chen

Dicarboxylic acids derived acylated-anthocyanins are common in nature, which can also be obtained by enzymatic acylation of anthocyanins. However, little research have focused on the properties of anthocyanins with dicarboxylic acid derivatives due to the complexity of isolation, detection, and identification. In this work, pelargonidin-3-glucoside (Pg3G) was acylated with various dicarboxylic acids. The conversion yields of acylated Pg3G were positively associated with carbon chain lengths of dicarboxylic acids. The primary acylated products were identified as pelargonidin- 3 -(6″-malonyl) glucoside, pelargonidin- 3 -(6″-succinyl) glucoside, and pelargonidin- 3 -(6″-glutaryl) glucoside using LC-MS and NMR. Furthermore, the three acylated Pg3G derivatives exhibited improved thermostability and enhanced lipophilicity compared with Pg3G. The improved thermostability was attributed to the influence of dicarboxylic acids substituent on the distribution of flavylium cation, quinoidal base, hemiketal, cis -chalcone, and trans -chalcone at the equilibrium condition. Overall, our research provided insights about the improved stability and lipophilicity of pelargonidin-3-glucoside following enzymatic acylation with aliphatic dicarboxylic acids.

✓ 已验证 DOI 高影响因子
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MOLECULES · 2016 ·Vol. 21 ·期 9 ·1109 · IF 2.465

Stability, Antioxidant Capacity and Degradation Kinetics of Pelargonidin-3-glucoside Exposed to Ultrasound Power at Low Temperature

Jianxia Sun,Zhouxiong Mei,Yajuan Tang,Lijun Ding,Guichuan Jiang,Chi Zhang,Aidong Sun,Weibin Bai

As an alternative preservation method to thermal treatment, ultrasound is a novel non-thermal processing technology that can significantly avoid undesirable nutritional changes. However, recently literature indicated that anthocyanin degradation occurred when high amplitude ultrasound was applied to juice. This work mainly studied the effect of ultrasound on the stability and antioxidant capacity of pelargonidin-3-glucoside (Pg-3-glu) and the correlation between anthocyanin degradation and •OH generation in a simulated system. Results indicated that the spectral intensities of Pg-3-glu decreased with increasing ultrasound power (200–500 W) and treatment time (0–60 min). The degradation trend was consistent with first-order reaction kinetics (R2> 0.9100). Further study showed that there was a good linear correlation between Pg-3-glu degradation and •OH production (R2= 0.8790), which indicated the important role of •OH in the degradation of anthocyanin during ultrasound exposure. Moreover, a decrease in the antioxidant activity of solution(s) containing Pg-3-glu as evaluated by the DPPH and FRAP methods was observed after ultrasound treatment.Keywords:ultrasound;cavitation;degradation;pelargonidin-3-glucoside;antioxidant activity;mechanism

CAS / MDL: 64-18-6 67-56-1 76-05-1
研究领域: 食品科学 · 化学 · 生物技术
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2021 · IF 5.279

Bioavailability, Absorption, and Metabolism of Pelargonidin-Based Anthocyanins Using Sprague–Dawley Rats and Caco-2 Cell Monolayers

Yang Xu,Yuting Li,Jiahong Xie,Lianghua Xie,Jianling Mo,Wei Chen

The present study is aimed to clarify the absorption and metabolism properties of pelargonidin-based anthocyanins. Results showed that pelargonidin-3-O-rutinoside (Pg3R) was absorbed in its intact form after oral administration and reached a maximum plasma concentration of 175.38 ± 55.95 nM at 60 min. Three main metabolites were identified in plasma, including Pg3R-monoglucuronide (m/z 755.2046), Pg3R-hydroxylated (m/z 595.1644), and Pg3R-demethylated (m/z 565.1569) metabolites. The plasma concentration of the Pg3R-demethylated metabolite (57.04 ± 23.15 nM) was much higher than that of other two metabolites, indicating that demethylation was the main metabolic pathway for Pg3R, while the glucuronide conjugate was detected as the dominant metabolic form of pelargonidin-3-O-glucoside (Pg3G). The bioavailability of Pg3R (1.13%) was fourfold higher than that of Pg3G (0.28%), demonstrating that anthocyanins linked to the rutinoside may exhibit higher bioavailability than that of glucoside. In vitro transport study unveiled that passive diffusion and active efflux were involved in the absorption of Pg3R and Pg3G.

CAS / MDL: 75-05-8 64-18-6 67-56-1
研究领域: 药理学 · 营养学 · 生物化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Food & Function · 2024 · IF 5.1

Acetylated pelargonidin-3-O-glucoside alleviates hepatocyte lipid deposition through activating the AMPK-mediated lysosome-autophagy pathway and redox state

Lianghua Xie,Xin Hao,Jiahong Xie,Jianling Mo,Changzheng Yuan,Wei Chen

Nonalcoholic fatty liver disease (NAFLD) is a worldwide public health issue, but a widely accepted therapy is still lacking until now. Anthocyanins are natural flavonoid compounds that possess various bioactivities, but their applications are limited due to their low bioavailability and stability. Acylated anthocyanins are reported to show higher stability, whereas their effects on NAFLD are still unclear. Herein, pelargonidin-3-O-(6′′-acetyl)-glucoside (Ace Pg3G) was found to dose-dependently reduce intracellular lipid droplets and triglycerides, and improve cellular oxidative stress that accompanied lipid deposition. Besides, Ace Pg3G was proved to activate AMPK phosphorylation, thus stimulating AMPK-mediated lysosome-autophagy pathway to eliminate overloaded lipid. Further study unveiled that Ace Pg3G regulated genes related to lipid metabolism downstream of AMPK to inhibit lipid synthesis and accelerate lipid oxidation. Overall, this study provided the first evidence, to our best knowledge, that Ace Pg3G ameliorated free fatty acid-induced lipid deposition in hepatocytes through regulating AMPK-mediated autophagy pathways and redox state.

研究领域: 营养学 · 分子生物学 · 药理学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Food & Function · 2022 ·Vol. 13 ·期 5 ·2618-2630 · IF 6.317

Acetylated pelargonidin-3-O-glucoside exhibits promising thermostability, lipophilicity, and protectivity against oxidative damage by activating the Nrf2/ARE pathway

Xin Hao,Jiahong Xie,Yuting Li,Wei Chen

Anthocyanins are natural products that display diverse bioactivities but are limited in their applications by low stability and bioavailability. Acylated anthocyanins are found to possess higher stability, while their bioactivities are still obscure. In this study, acetylation of pelargonidin-3-O-glucoside (Pg3G) was catalyzed by Candida antarctica lipase B (CALB) for the first time, with a conversion rate up to 88.77% over 48 h. The acetylated product was identified as pelargonidin-3-O-(6′′-acetyl)-glucoside and its properties were detected. Notably, acetylated Pg3G (Ace Pg3G) possessed better thermostability and lipophilicity than Pg3G, indicating a longer retention time at physiological pH and facilitating penetration into the lipophilic medium as well as the cell membrane. Most importantly, Ace Pg3G exerted better alleviation effects against H2O2-induced oxidative hepatic damage than parent Pg3G via activating the Nrf2/ARE signaling pathway and upregulating the expressions of the downstream phase II detoxification enzymes GCLC and HO-1, thereby reversing redox imbalance and enhancing cell survival. Overall, our research unveiled the better health benefits of Ace Pg3G and also provided new insights about the applications of acetylated anthocyanins in food, cosmetic, and pharmaceutical products.

CAS / MDL: 75-85-4 75-05-8 67-68-5
研究领域: 食品科学 · 药理学 · 生物化学 · 分子生物学
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2020 · IF 5.162

In vitro study of bioaccessibility, antioxidant, and α-glucosidase inhibitory effect of pelargonidin-3-O-glucoside after interacting with beta-lactoglobulin and chitosan/pectin

Vemana Gowd,Naymul Karim,Lianghua Xie,Mohammad Rezaul Islam Shishir,Yang Xu,Wei Chen

Polysaccharides and fruit extracts are applied in dairy products to enhance their nutritional property, but the effects of such formulations on the functions and biological activities are yet to be explored. Therefore, this study was aimed at evaluating the effect of interactions among milk protein (beta-lactoglobulin; BLG), polysaccharides (pectin, P; chitosan, CH), and anthocyanin (pelargonidin-3- O -glucoside; P3G) in improving the bioavailability and biological activity of P3G. After gastrointestinal digestion (GID), the content of free P3G in different model solutions were as follows: P3G-alone (73.59 μg/mL), P3G-P (66.59 μg/mL), P3G-CH (36.72 μg/mL), P3G-BLG (64.92 μg/mL), P3G-P-BLG (64.92 μg/mL), and P3G-CH-BLG (39.61 μg/mL). Less amount of free P3G in model solutions indicated increased complex formation of P3G with protein and/or polysaccharides during GID. These complexes resulted in protection and progressive release of P3G in the gastrointestinal tract. Chitosan exhibited more protection to P3G compared with P and BLG. In addition, α-glucosidase inhibitory activity and ROS scavenging activities of conjugated-P3G samples were potentially augmented after GID. However, the presence of polysaccharides and protein in the model solutions did not show any negative effect on the biological activity of P3G. Thus, pure P3G can be used as a nutritional ingredient in dairy industries.

研究领域: 食品科学 · 营养学 · 生物化学 · 药理学
✓ 已验证 DOI PubMed 高影响因子
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