JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2017
·
IF 3.154
Fujie Yan,Yunyun Yang,Lushuang Yu,Xiaodong Zheng
Main components of Apios americana leaves extract (ALE) were flavonoid C-glycosides, including vitexin (46.7%), schaftoside (18.9%), and orientin (4.32%). In vitro, ALE restored glucose consumption, glucose uptake, and glycogen content in glucose-induced hepatic cells. Exposure of HepG2 cells to high glucose resulted in reactive oxygen species and O2– accumulation, while ALE alleviated these increases by 47 ± 0.68 and 68 ± 0.74%, respectively. Glucose increased c-Jun N-terminal kinase (JNK) and decreased extracellular signal-regulated kinases 1 and 2 (ERK1/2) and p38 phosphorylation, while ALE reduced p-JNK and p-p38 but not p-ERK1/2, accompanied by nuclear factor erythroid 2-related factor 2 (Nrf2), heme oxygenase-1, and NAD(P)H quinine oxidoreductase 1 downregulation. In vivo, the lifespan of Caenorhabditis elegans was more violently shortened by paraquat under hyperglycemia, while ALE protected this damage in N2 worms (2.6 times extension) but not in daf-16 mutants. Furthermore, p38/PMK-1 and Nrf2/SKN-1 expressions in worms were suppressed by glucose, which were reversed by ALE treatment. These results suggest that ALE prevents glucose-induced damage via regulating specific mitogen-activated protein kinases and Nrf2 pathways.
研究领域:
药理学
·
分子生物学
✓ 已验证
DOI
PubMed
高影响因子
CHEMISTRY OF NATURAL COMPOUNDS
·
2023
·Vol. 59
·期 6
·1067-1074
·
IF 0.8
Chen Yi-Fang,Luo Ji-Feng,Zhang Yan-Ni,Wang Yue-Hu
Four flavonoid C -glycosides, including two new diglycosides, dendrodiglycosides A ( 1 ) and B ( 2 ), along with known isoviolanthin ( 3 ) and apigenin 6- C - β -D-glucopyranosyl-(1→2)-α-L-arabinopyranoside ( 4 ), were isolated from the leaves of Dendrobium officinale (Orchidaceae). Their structures were elucidated by NMR and MS. Apigenin 6- C - β -D-glucopyranosyl-(1→2)-α-L-arabinopyranoside exhibited an inhibitory effect against tyrosinase with an IC 50 value of 146.5 μg/mL.
研究领域:
植物化学
·
药理学
✓ 已验证
DOI
高影响因子
MICROCHEMICAL JOURNAL
·
2018
·
IF 2.746
Li Duan,Wei-Hong Zhang,Zhan-Hui Zhang,E-Hu Liu,Long Guo
Nowadays, deep eutectic solvents (DESs) are emerging as a new type of green and sustainable solvents for efficient extraction of bioactive compounds from natural products . In the present study, to evaluation of DESs for the extraction of flavone C -glycosides, a total of twelve choline chloride based DESs were tailored for simultaneous extraction three main bioactive flavone C -glycosides (2″‑ O ‑galactopyranosylorientin, orientin and vitexin) from Flos Trollii. The DES composed of choline chloride and zinc bromide showed the best extraction efficiency for the flavone C -glycosides compared with conventional organic solvents (methanol and 50% methanol). Subsequent, the extraction parameters for the three flavone C -glycosides, including liquid-solid ratios, water content (%) in the selected DESs, and extraction time were optimized using response surface methodology and the optimal extraction condition are liquid-solid ratio, 42 mL/g; water content, 48%; extraction time, 28 min. In addition, the three flavone C -glycosides were recovered from DESs by macroporous resin (D101) with a satisfactory yield between 75.4% and 80.5%. The present research indicated that DESs were efficient and sustainable for extraction main flavone C -glycosides from Flos Trollii and the data acquired in this study could contribute to further DESs application in extraction of bioactive compounds from natural products.
研究领域:
植物化学
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天然产物开发
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药物化学
✓ 已验证
产品关联
DOI
高影响因子
PLANT JOURNAL
·
2021
·Vol. 106
·期 2
·351-365
·
IF 6.486
Cheng-Yong Feng,Shan-Shan Li,Goro Taguchi,Qian Wu,Dan-Dan Yin,Zhao-Yu Gu,Jie Wu,Wen-Zhong Xu,Cheng Liu,Liang-Sheng Wang
SUMMARY Lotus plumule, the embryo of the seed of the sacred lotus ( Nelumbo nucifera ), contains a high accumulation of secondary metabolites including flavonoids and possesses important pharmaceutical value. Flavonoid C -glycosides, which accumulate exclusively in lotus plumule, have attracted considerable attention in recent decades due to their unique chemical structure and special bioactivities. As well as mono- C -glycosides, lotus plumule also accumulates various kinds of di- C -glycosides by mechanisms which are as yet unclear. In this study we identified two C -glycosyltransferase (CGT) genes by mining sacred lotus genome data and provide in vitro and in planta evidence that these two enzymes (NnCGT1 and NnCGT2, also designated as UGT708N1 and UGT708N2, respectively) exhibit CGT activity. Recombinant UGT708N1 and UGT708N2 can C -glycosylate 2-hydroxyflavanones and 2-hydroxynaringenin C -glucoside, forming flavone mono- C -glycosides and di- C -glycosides, respectively, after dehydration. In addition, the above reactions were successfully catalysed by cell-free extracts from tobacco leaves transiently expressing NnCGT1 or NnCGT2. Finally, enzyme assays using cell-free extracts of lotus plumule suggested that flavone di- C -glycosides (vicenin-1, vicenin-3, schaftoside and isoschaftoside) are biosynthesized through sequentially C -glucosylating and C -arabinosylating/ C -xylosylating 2-hydroxynaringenin. Taken together, our results provide novel insights into the biosynthesis of flavonoid di- C -glycosides by proposing a new biosynthetic pathway for flavone C -glycosides in N. nucifera and identifying a novel uridine diphosphate-glycosyltransferase (UGT708N2) that specifically catalyses the second glycsosylation, C -arabinosylating and C -xylosylating 2-hydroxynaringenin C -glucoside.
研究领域:
植物生物化学
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分子生物学
·
药理学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
Foods
·
2022
·Vol. 11
·期 6
·882
·
IF 5.561
Liangqin Xie,Zeyuan Deng,Jie Zhang,Huanhuan Dong,Wei Wang,Banghuai Xing,Xiaoru Liu
Flavonoids are well known for their extensive health benefits. However, few studies compared the differences between flavonoid O-glycoside and C-glycoside. In this work, flavonoid O-glycoside (isoquercitrin), C-glycoside (orientin), and their aglycones (quercetin and luteolin) were chosen to compare their differences on antioxidant activities and metabolism during in vitro digestion and in vivo. In vitro digestion, the initial antioxidant activity of the two aglycones was very high; however, they both decreased more sharply than their glycosides in the intestinal phase. The glycosidic bond of flavonoid O-glycoside was broken in the gastric and intestinal stage, while the C-glycoside remained unchanged. In vivo, flavonoid O-glycoside in plasma was more elevated than C-glycoside on the antioxidant activity; however, flavonoid C-glycoside in urine was higher than O-glycoside. These results indicate that differences of flavonoid glycosides and their aglycones on antioxidant activity are closely related to their structural characteristics and metabolism in different samples. Aglycones possessed higher activity but unstable structures. On the contrary, the sugar substituents reduced the activity of flavonoids while improving their stability and helping to maintain antioxidant activities after digestion. Especially the C-glycoside was more stable because the stability of the C–C bond is higher than that of the C–O bond, which contributes to the difference between flavonoid O-glycoside and C-glycoside on the absorption and metabolism in vivo. This study provided a new perspective for comparing flavonoid O-glycoside, flavonoid C-glycoside, and their aglycones on their structure–activity relationship and metabolism.Keywords:flavonoid;O-glycoside;C-glycoside;aglycones;in vitro digestion;antioxidant activity
研究领域:
营养学
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药理学
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生物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
Journal of Chemistry
·
2020
·
IF 1.79
Yueyuan Chen,Jiaoyang Dang,Xiaojie Yan,Fenglai Lu,Dianpeng Li
Deep eutectic solvents (DESs) are emerging as new extraction solvents for the extraction of bioactive compounds from natural plants. In this work, a total of thirteen choline chloride-based DESs were synthesized and evaluated for the simultaneous extraction of five bioactive flavone di-C-glycosides from Premna fulva Craib. DES-F, which was composed of choline chloride and 1,3-propanediol, showed the best extraction efficiency for the flavone di-C-glycosides, exceeding that of the conventional industrial solvent (40% ethanol). Subsequently, the extraction parameters for ultrasonic-assisted extraction (liquid-solid ratio, water content (%) in the selected DES, and extraction time) were optimized using response surface methodology. Furthermore, the microstructural alterations in the samples after extraction were evaluated using scanning electron microscopy. In addition, we further verified the recovery of flavone di-C-glycosides from the DESs using macroporous resins and evaluated the reusability of the DESs as solvents. The results indicated that DES-F was an efficient and sustainable solvent for the extraction of bioactive flavone di-C-glycosides from Premna fulva Craib. Therefore, this novel strategy may represent a sustainable approach for the extraction of bioactive products and could make phytochemistry more attractive and environmentally friendly.
研究领域:
植物化学
·
环境科学
✓ 已验证
DOI
高影响因子
Chinese Journal of Natural Medicines
·
2014
·
IF 0
Pei-Pei WANG,Guo-Wei ZHAO,Wen XIA,En-Ji HAN,Lan XIANG
This study was conducted to investigate the chemical constituents of Piper wallichii (Miq.) Hand.-Mazz. and evaluate their biological activity. Compounds were isolated by various column chromatographic methods, and their structures were elucidated on the basis of physical characteristics and spectral data. The 1, 1-diphenyl-2-picrylhydrazyl (DPPH)-scavenging activity and acetylcholinesterase (AChE)-inhibitory activity of the compounds were evaluated. Five compounds were obtained and identified as 8- C -β-D-glucopyranosylkaempferol-3- O -β-D-glucopyranoside ( 1 ), 1, 2-dihydro-6,8-dimethoxy-7-hydroxy-1-(3, 5-dimethoxy-4-hydroxyphenyl)- N 1 , N 2 -bis-[2-(4-hydroxyphenyl)ethyl]-2, 3-naphthalene dicarboxamide ( 2 ), goniothalactam ( 3 ), aristololactam A IIIa ( 4 ) and piperlonguminine ( 5 ). Compound 1 was a new flavonol C -glycoside, 2 was a rare lignanamide, which was isolated from the family Piperaceae for the first time, and compound 3 was isolated from this plant for the first time. Among them, 2 showed potent DPPH-scavenging activity, with IC 50 of 31.38 ± 0.97 μmol·L −1 ; Compounds 2 , 3 , and 4 showed AChE inhibitory activity at 100 μmol·L −1 , with inhibition rates of 28.57% ± 1.47%, 18.48% ± 2.41% and 17.4% ± 3.03%, respectively.
研究领域:
植物化学
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药理学
✓ 已验证
产品关联
DOI
PubMed
Nature Communications
·
2024
·Vol. 15
·期 1
·1-13
·
IF 14.7
Li Min,Zhou Yang,Wen Zexing,Ni Qian,Zhou Ziqin,Liu Yiling,Zhou Qiang,Jia Zongchao,Guo Bin,Ma Yuanhong,Chen Bo,Zhang Zhi-Min,Wang Jian-bo
Despite the broad potential applications of C -glycosides, facile synthetic methods remain scarce. Transforming glycosyltransferases with promiscuous or natural O -specific chemoselectivity to C -glycosyltransferases is challenging. Here, we employ rational directed evolution of the glycosyltransferase MiCGT to generate MiCGT-QDP and MiCGT-ATD mutants which either enhance C- glycosylation or switch to O -glycosylation, respectively. Structural analysis and computational simulations reveal that substrate binding mode govern C -/ O -glycosylation selectivity. Notably, directed evolution and mechanism analysis pinpoint the crucial residues dictating the binding mode, enabling the rational design of four enzymes with superior non-inherent chemoselectivity, despite limited sequence homology. Moreover, our best mutants undergo testing with 34 substrates, demonstrating superb chemoselectivities, regioselectivities, and activities. Remarkably, three C -glycosides and an O -glycoside are produced on a gram scale, demonstrating practical utility. This work establishes a highly selective platform for diverse glycosides, and offers a practical strategy for creating various types of glycosylation platforms to access pharmaceutically and medicinally interesting products.
研究领域:
生物化学
·
酶工程
·
药物化学
✓ 已验证
DOI
PubMed
高影响因子
FOOD RESEARCH INTERNATIONAL
·
2019
·
IF 3.579
Xinfeng Zhang,Sijie Zhang,Beibei Gao,Zheng Qian,Jingjing Liu,Shihua Wu,Jinping Si
Recently, the flowers of Dendrobium catenatum ( D. officinale ) have been approved as new food ingredient. This study aimed to investigate the herb-markers and their antioxidant activities in methanolic extracts of D. catenatum flowers, and to establish the quality evaluation methods for raw materials and their products of flower by HPLC. The methanolic extract of 11 strains of D. catenatum flowers were found to contain a high content of total phenol and flavonoids, and they possessed potential antioxidant capacities based on DPPH radical scavenging assay. A total of 21 phenolic herb-markers were selected according to the similarity and principal component analysis of the chromatographic fingerprinting profiles. Their structures were further elucidated by UV, HPLC-DAD-ESI-QTOF-MS/MS and NMR analyses. The identified compounds included 2 phenylpropanoids, 11 C -glycosylflavones and 6 O -glycosylflavones, which could be employed as the indicators for quantitative evaluation of the quality and authenticity of the flowers. Based on the pre-column DPPH/ABTS + -HPLC analysis, the major compounds contributed to the antioxidative activity were identified as 1- O -caffeoyl- β -D-glucoside, rutin and isoquercitrin, all of which, were also the most abundant constituents in the methanolic extract. The results suggest the potential of D. catenatum flowers as a new antioxidant resources for medicinal and food products.
研究领域:
生药学
·
分析化学
·
食品科学
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药学
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植物学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
Nutrients
·
2025
·Vol. 17
·期 15
·2456
·
IF 5
Ming Chu,Yingying Tong,Lei Zhang,Yu Zhang,Jun Dang,Gang Li
Background: The metabolic dysfunction-associated steatotic liver disease (MASLD) represents an escalating global health concern, with effective treatments still lacking. Given its complex pathogenesis, multi-targeted strategies are highly desirable. Methods: This study reports the isolation of four flavone C-glycosides (FCGs) from Dianthus superbus L. and explores their potential in treating MASLD. The bioactivity and underlying mechanisms of FCGs were systematically evaluated by integrating network pharmacology, molecular docking, and zebrafish model validation. Results: Network pharmacology analysis revealed that FCGs may modulate multiple MASLD-related pathways, including lipid metabolism, insulin signaling, inflammation, and apoptosis. Molecular docking further confirmed strong binding affinities between FCGs and key protein targets involved in these pathways. In the zebrafish model of MASLD induced by egg yolk powder, FCGs administration markedly attenuated obesity, hepatic lipid accumulation, and liver tissue damage. Furthermore, FCGs improved lipid metabolism and restored locomotor function. Molecular analyses confirmed that FCGs upregulated PPARγ expression to promote lipid metabolism, restored insulin signaling by enhancing INSR, PI3K, and AKT expression, and suppressed inflammation by downregulating TNF, IL-6 and NF-κB. Additionally, FCGs inhibited hepatocyte apoptosis by elevating the BCL-2/BAX ratio. Conclusions: These findings highlight the multi-pathway regulatory effects of FCGs in MASLD, underscoring its potential as a novel therapeutic candidate for further preclinical development.
研究领域:
药理学
·
生物化学
·
分子生物学
·
药用植物研究
·
药物开发
✓ 已验证
产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）