PeerJ
·
2019
·
IF 2.353
Hongli Yin,Ji Ma,Jichun Han,Maoru Li,Jing Shang
Background Quercetin (Qr), isoquercitrin (IQ), and quercetin-3-O-β-D-glucuronide (QG) are powerful phytochemicals that have been shown to exhibit disease prevention and health promotion properties. However, there may exist transformations between Qr, IQ, and QG in vivo . And the pharmacokinetic profiles of Qr, IQ, and QG have not been systematically compared. The pharmacokinetics study would be helpful to better understand the pharmacological actions of them. Methods Herein, we developed a reliable HPLC-MS method to compare the pharmacokinetics of Qr, IQ, and QG after separate (50 mg/kg) oral administration of them in rats, using puerarin as internal standard. The detection was performed using negative selected ion monitoring. This method was validated in terms of selectivity, linearity, precision, accuracy, extraction recovery, matrix effect, and stability; and shows reliabilities in monitoring the pharmacokinetic behaviors of these three compounds. Results Our results showed that after separate oral administration of Qr, IQ, and QG, all of the compounds could be detected in plasma. In addition, QG could be detected in the Qr group; Qr and QG could be measured in the IQ group; and Qr could be found in rat plasma after 1.5 h of QG administration. Moreover, the AUC 0− t of Qr in the; Qr group (2,590.5 ± 987.9 mg/L*min), IQ group (2,212.7 ± 914.1 mg/L*min), and QG group (3,505.7 ± 1,565.0 mg/L*min) was larger than the AUC 0− t of QG in the; Qr group (1,550.0 ± 454.2 mg/L*min), IQ group (669.3 ± 188.3 mg/L*min), and QG group (962.7 ± 602.3 mg/L*min). The AUC 0− t of IQ was the lowest among all groups. Discussion Quercetin, IQ, and QG can all be absorbed into plasma. A mutual transformation exists between Qr and QG, and IQ can be metabolized into Qr and QG in SD rats. These results would provide a meaningful basis for understanding the pharmacological actions of these three compounds.
研究领域:
药理学
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分析化学
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DOI
PubMed
高影响因子
MOLECULES
·
2016
·Vol. 21
·期 9
·1246
·
IF 2.465
Xican Li,Qian Jiang,Tingting Wang,Jingjing Liu,Dongfeng Chen
The role of the 6″-OH (ω-OH) group in the antioxidant activity of flavonoid glycosides has been largely overlooked. Herein, we selected quercitrin (quercetin-3-O-rhamnoside) and isoquercitrin (quercetin-3-O-glucoside) as model compounds to investigate the role of the 6″-OH group in several antioxidant pathways, including Fe2+-binding, hydrogen-donating (H-donating), and electron-transfer (ET). The results revealed that quercitrin and isoquercitrin both exhibited dose-dependent antioxidant activities. However, isoquercitrin showed higher levels of activity than quercitrin in the Fe2+-binding, ET-based ferric ion reducing antioxidant power, and multi-pathways-based superoxide anion-scavenging assays. In contrast, quercitrin exhibited greater activity than isoquercitrin in an H-donating-based 1,1-diphenyl-2-picrylhydrazyl radical-scavenging assay. Finally, in a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl assay based on an oxidatively damaged mesenchymal stem cell (MSC) model, isoquercitrin performed more effectively as a cytoprotector than quercitrin. Based on these results, we concluded that (1) quercitrin and isoquercitrin can both indirectly (i.e., Fe2+-chelating or Fe2+-binding) and directly participate in the scavenging of reactive oxygen species (ROS) to protect MSCs against ROS-induced oxidative damage; (2) the 6″-OH group in isoquercitrin enhanced its ET and Fe2+-chelating abilities and lowered its H-donating abilities via steric hindrance or H-bonding compared with quercitrin; and (3) isoquercitrin exhibited higher ROS scavenging activity than quercitrin, allowing it to improve protect MSCs against ROS-induced oxidative damage.Keywords:quercitrin;isoquercitrin;Q3G;6″-OH;ω-OH;flavonoid glycoside;antioxidant mechanisms;mesenchymal stem cells
研究领域:
药理学
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生物化学
·
细胞生物学
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产品关联
DOI
PubMed
高影响因子
RSC Advances
·
2018
·Vol. 8
·期 27
·14967-14974
·
IF 2.936
Lei Zhang,Shi-Tao Zhang,Yan-Chun Yin,Shu Xing,Wan-Nan Li,Xue-Qi Fu
Glucagon-like peptide (GLP)-1 is a potent glucose-dependent insulinotropic gut hormone released from intestinal L cells. The aim of this study was to investigate isoquercitrin as an inhibitor of dipeptidyl peptidase IV (DPP-IV) and determine whether it affects GLP-1 release in normal mice and NCI-H716 cells. In vitro, we used chromogenic substrate method detection methods to measure DPP-IV. We found that isoquercitrin was a competitive inhibitor, with IC50 and Ki values of 96.8 and 236 μM, respectively. Isoquercitrin and sitagliptin also stimulated GLP-1 release in NCI-H716 cells. In vivo, a type 2 diabetic mouse model was established, and oral treatment with different concentration of isoquercitrin and sitagliptin for 8 weeks significantly decreased the fasting blood glucose level. The weight and the levels of serum GLP-1 and insulin of the mice in the isoquercitrin group were higher than those in the model group (P < 0.001). An oral glucose tolerance test showed that the isoquercitrin significantly inhibited postprandial blood glucose changes in a dose-dependent manner. These findings demonstrated the hypoglycemic effects of isoquercitrin and indicated that isoquercitrin improved insulin sensitivity by targeting DPP-IV.
研究领域:
药理学
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内分泌学
·
分子生物学
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DOI
PubMed
高影响因子
FOOD CHEMISTRY
·
2024
·
IF 8.5
Yu-Fan Zhan,Zhuo-Hao Meng,Cheng-Hai Yan,Min Tan,Marriam Khurshid,Yi-Jiangcheng Li,Shao-Jun Zheng,Jun Wang
Enzymatically modified isoquercitrin (EMIQ) is a glyco-chemically modified flavonoid exhibiting notably high biological activity, such as antioxidant, anti-inflammatory and anti-allergic properties. However, the utilization of expensive substrates such as isoquercitrin and cyclodextrin in the conventional approach has hindered the industrial-scale production of EMIQ due to high cost and low yields. Hence, the development of a cost-effective and efficient method is crucial for the biological synthesis of EMIQ. In this study, a natural cascade catalytic reaction system was constructed with α -L-rhamnosidase and amylosucrase using the inexpensive substrates rutin and sucrose. Additionally, a novel approach integrating gradient temperature regulation into biological cascade reactions was implemented. Under the optimal conditions, the rutin conversion reached a remarkable 95.39% at 24 h. Meanwhile, the productivity of quercetin-3- O -tetraglucoside with the best bioavailability reached an impressive 41.69%. This study presents promising prospects for future mass production of EMIQ directly prepared from rutin and sucrose.
研究领域:
生物技术
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生物化学
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药学
·
食品科学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES
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2017
·
IF 2.603
Hongjuan Li,Ying Liu,Yuetao Yi,Qin miao,Sujing Liu,Feng Zhao,Wei Cong,Chunhua Wang,Chuanhai Xia
In China, Poacynum hendersonii is frequently used as a substitute for Apoacynum venetum L (Luobuma), which is a famous traditional Chinese medicine. Quercetin-3- O -sophoroside and isoquercitrin are two major flavonoids in Poacynum hendersonii leaves. In this work, a suitable method was established for the large-scale preparation of quercetin-3- O -sophoroside (QOS) and isoquercitrin (ISO) from Poacynum hendersonii leaves using macroporous resin combined with Sephadex LH-20 column chromatography. The adsorption/desorption capacities and desorption ratios of six macroporous resins were evaluated using static experiments. The HPD-300 resin had the best adsorption performance because it had the largest surface area, and was selected for further study. Compared with pseudo-first-order and intraparticle diffusion kinetics models, the pseudo-second-order model could better fit the adsorption kinetics of both QOS and ISO on the HPD-300 resin. In addition, the adsorption isotherms of the two compounds on the HPD-300 resin were fitted well to the Langmuir model. Under optimal conditions, the purities of QOS and ISO in the product were increased from 2.16% and 1.26% to 21.34% and 10.70% with recovery yields of 82.1% and 77.3%, respectively. Subsequently, Sephadex LH-20 column chromatography was employed for improving the purities of the two compounds. After separation by Sephadex LH-20 column chromatography, the purities of QOS and ISO achieved 93.5% and 95.6%, respectively.
研究领域:
药学
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化学工程
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天然产物化学
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中药学
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DOI
PubMed
高影响因子
FOOD CHEMISTRY
·
2026
·
IF 9.8
Ruo-Xi Mei,Tian Xia,Ji-Ming Guo,Ding Wang,Zhi-Ang Zhang,Yan Xu,Richard Ansah Herman,Jun Wang
Enzymatically modified isoquercitrin (EMIQ), a natural compound known for its antioxidant, anti-proliferative, and anti-inflammatory properties, exhibits remarkable bioavailability and low toxicity, making it a promising therapeutic agent for diabetic kidney disease. However, conventional chemical synthesis of EMIQ is hampered by inefficiency, high reagent consumption, and substantial by-product formation. In this study, EMIQ was produced from rutin and sucrose using a novel Heteropeptide Self-Assembly-Cascaded Dual-Enzyme (HSC-DE) system, which co-immobilized α -L-rhamnosidase and amylosucrase via SpyTag/SpyCatcher pairs. This system significantly enhances reaction efficiency by adding the substrate and gradient temperature, achieving a sucrose conversion rate of 98.3% within 24 h, which was increased by 5.7% compared to previous (92.6%). Notably, the yield of quercetin-3- O -tetraglucoside, the form with optimal bioavailability, reached 62.1%, an increase of 12% over previous methods. This study presents a novel, sustainable, and highly effective bioengineering strategy for the synthesis of EMIQ, highlighting its potential for scalable and environmentally friendly production.
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DOI
PubMed
高影响因子
PHYTOTHERAPY RESEARCH
·
2026
·
IF 8.1
Qi Wu,Yupeng Tao,Chenchen Sun,Yijing Li,Tianyu Liu,Buhui Liu,Wei Li,Kun Gao,Yao Zhou
Isoquercitrin (IQ) is a natural flavonoid compound with potent anti-inflammatory and antioxidant effects; its role and mechanism of action in diabetic kidney disease (DKD) are unclear. This study clarified the role of IQ in delaying DKD and regulating tubular epithelial cell lipid metabolism. db/db mice were randomly divided into DKD, low-dose IQ, high-dose IQ, and dapagliflozin groups. C57BL/6J mice were used as controls. NRK-52E cells and connexin 43 (Cx43) knockdown ( Cx43 +/− ) cells were incubated with IQ and bovine serum albumin (BSA) in vitro. A cell counting kit-8 (CCK-8) was used to assess cell viability and a reactive oxygen species (ROS) detection kit was used to detect oxidative stress levels. Mitochondrial function was assessed using transmission electron microscopy, fluorescence staining, and an ATP assay. Western blotting was used to assess the levels of relevant proteins. IQ ameliorated renal dysfunction in db/db mice, and proteomic analysis indicates its mechanism involves the regulation of lipid metabolism and mitochondrial function. BSA increased ROS generation, enhanced fluorescence, decreased ATP content, and increased the expression of phosphorylated extracellular signal-regulated kinase (p-ERK), Cx43, and cluster of differentiation 36 (CD36) in NRK-52E cells; these effects were ameliorated by IQ. After Cx43 +/− NRK cells were incubated with BSA, the ROS/O 2 – fluorescence intensity and p-ERK expression were lower than those in wildtype NRK-52E cells. IQ delayed the occurrence and development of DKD by modulating mitochondrial lipid metabolism through the inhibition of Cx43 expression and ERK phosphorylation. This study provides valuable insights for the pharmacological treatment of DKD.
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产品关联
DOI
PubMed
高影响因子
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