Comparative analysis of chemical components in different parts of Epimedium Herb

Zhou, Ming; Zheng, Wei; Sun, Xinguang; Yuan, Ming; Zhang, Jie; Chen, Xiaojuan; Yu, Kate; Guo, Baolin; B, Ma

doi:10.1016/j.jpba.2021.113984

Cited by 27 publications

(22 citation statements)

References 20 publications

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“…These Epimedium flavonols possess basic chemical structures with a prenyl group at C-8 position of ring A, and with the most common glycosylation pattern: a glucose at C-7, and a rhamnose initially at C-3 following the addition of glucose, xylose or rhamnose (1–2 linkage). However, the key difference is the presence or absence of hydroxyl group at C-3′ position of ring B. Depicted in Figure 1 are two key types of Epimedium flavonols, among which Type A Epimedium flavonols with the backbone of 8-prenylated kaempferol are widely found in Epimedium species, including subtypes of icaritin (4′-methoxyl) and demethylicaritin (4′-hydroxyl) ( Jian et al, 2015 ; Zhou et al, 2021 ). By contrast, Type B of Epimedium flavonols with the backbone of 8-prenylated quercetin are rarely isolated or detected, including subtypes of 3′-hydroxylicaritin (4′-methoxyl) ( Wang et al, 2007 ; Tu et al, 2011 ) and 3′-hydroxyldemethylicaritin (4′-hydroxyl) ( Li et al, 2017 ), shown in Figure 1 .…”

Section: Introductionmentioning

confidence: 99%

New 8-prenylated quercetin glycosides from the flowers of Epimedium acuminatum and their testosterone production-promoting activities

Zhang

Zeng

et al. 2022

Front. Chem.

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Phytochemical investigation was carried out for the flowers of Epimedium acuminatum Franchet. by first conducting LC-MS analysis, leading to the identification of 32 compounds. Furthermore, guided by LC-MS profiling, three new 8-prenylated quercetin glycosides (3′-hydroxylikarisoside C, 3′-hydroxylepimedoside E, 3′-hydroxyldiphylloside B), one new anthocyanin (delphinidin-3-O-p-coumaroyl-sophoroside) and six known compounds were isolated from the flowers of E. acuminatum for the first time, and their structures were characterized based on spectroscopic methods including 1D and 2D NMR, and HRESIMS. Combining our discoveries and literature survey, a revised classification of Epimedium flavonols was proposed as Type A (8-prenylated kaempferol based), which was further subdivided into subtype icaritin and subtype demethylicaritin, and Type B (8-prenylated quercetin based), which was further subdivided into subtype 3′-hydroxylicaritin and subtype 3′-hydroxyldemethylicaritin. The structure-activity relationship (SAR) study was carried out by comparing testosterone production-promoting activities of all the new compounds along with nine related Epimedium flavonols, revealing that the new 8-prenylated quercetin glycosides (subtype 3′-hydroxyldemethylicaritin in Type B) exhibited lower testosterone production-promoting activities in rat primary Leydig cells than Epimedium flavonols of subtype demethylicaritin in Type A, but possessed higher activities than the Epimedium flavonols of subtype icaritin in Type A. These results suggested that either methylation at C-4′ position or hydroxylation at C-3′ position of ring B could significantly reduce the testosterone production-promoting activities of Epimedium flavonols.

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Section: Introductionmentioning

confidence: 99%

New 8-prenylated quercetin glycosides from the flowers of Epimedium acuminatum and their testosterone production-promoting activities

Zhang

Zeng

et al. 2022

Front. Chem.

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“…The leaves of Epimedium have many beneficial effects on human and animal health as tonics, antirheumatics, antiosteoporotics, and aphrodisiacs in curing sexual dysfunction [ 2 ]. Flavonoids have been proven to be the major bioactive components in the leaves of Epimedium , which are mainly composed of prenylated flavonol glycosides, such as epimedin A, epimedin B, epimedin C, and icariin [ [2] , [3] , [4] ]. The stability and solubility of flavonols could be largely improved by glycosylation due to obvious changes in physicochemical properties, which greatly affects the accumulation of flavonol glycosides in plant cells [ 5 , 6 ].…”

Section: Introductionmentioning

confidence: 99%

Genome-wide analysis of UGT gene family identified key gene for the biosynthesis of bioactive flavonol glycosides in Epimedium pubescens Maxim.

Luo

et al. 2022

Synthetic and Systems Biotechnology

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“…Anhydroicaritin (AHI) is a flavonoid with antitumor biological and pharmacological effects (Nguyen et al, 2017). AHI is the primary metabolic product of Epimedium brevicornum after digestion and absorption (Zhou et al, 2021). Glutathione peroxidase 1 (GPX1) is a vital antioxidant enzyme that can catabolize the hydrogen oxide entering the human body and reduce peroxide's damage to the body (Huang et al, 2018).…”

Section: Introductionmentioning

confidence: 99%

Anhydroicaritin Inhibits EMT in Breast Cancer by Enhancing GPX1 Expression: A Research Based on Sequencing Technologies and Bioinformatics Analysis

Shi

Xiao

et al. 2022

Front. Cell Dev. Biol.

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Background: Breast cancer (BC) is the leading cause of cancer-related deaths among women worldwide. The application of advanced technology has promoted accurate diagnosis and treatment of cancer. Anhydroicaritin (AHI) is a flavonoid with therapeutic potential in BC treatment. The current study aimed to determine AHI’s mechanism in BC treatment via RNA sequencing, comprehensive bioinformatics analysis, and experimental verification.Methods: Network pharmacology and MTT (3-(4,5)-dimethylthiazolyl-3,5- diphenyltetrazolium bromide) experiments were conducted to first confirm AHI’s anti-BC effect. RNA sequencing was performed to identify the genes affected by AHI. Differential expression analysis, survival analysis, gene set enrichment analysis, and immune infiltration analysis were performed via bioinformatics analysis. Western blot analysis, reverse transcription–polymerase chain reaction (RT-PCR) experiment, molecular docking, and drug affinity responsive target stability (DARTS) experiments were also performed to confirm AHI’s direct effect on glutathione peroxidase 1 (GPX1) expression. Confocal immunofluorescence analysis was conducted to verify AHI’s effect on the occurrence and development of epithelial–mesenchymal transition (EMT). Finally, BC nude mouse xenografts were established, and AHI’s molecular mechanism on BC was explored.Results: Network pharmacology results demonstrated that AHI’s therapeutic targets on BC were related to the proliferation, invasion, and metastasis of BC cells. AHI significantly inhibited the proliferation of 4T1 and MDA-MB-231 BC cells in the MTT experiments. RNA sequencing results showed that AHI upregulated the GPX1 expression in the 4T1 and MDA-MB-231 BC cells. Next, bioinformatics analysis revealed that GPX1 is less expressed in BC than in normal breast tissues. Patients with high GPX1 expression levels tended to have prolonged overall survival and disease-free survival than patients with low GPX1 expression levels in BC. Western blot and RT-PCR experiments revealed that AHI increased the protein and mRNA levels of GPX1. Molecular docking and DARTS experiments confirmed the direct binding combination between AHI and GPX1. After the evaluation of the EMT scores of 1,078 patients with BC, we found a potential anti-BC role of GPX1 possibly via suppression of the malignant EMT. The confocal immunofluorescence analysis showed that AHI increased E-cadherin expression levels and reduced vimentin expression levels in BC cells. Animal experiments showed that AHI significantly inhibited tumor growth. AHI also inhibited EMT by enhancing GPX1 and caspase3 cleavage, hence inhibiting EMT markers (i.e., N-cadherin and vimentin) and Ki-67.Conclusion: GPX1 plays a critical role in BC, which may be a biomarker for the prognosis. In addition, AHI suppressed EMT by increasing GPX1 expression, which may serve as a potential therapy for BC treatment.

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Comparative analysis of chemical components in different parts of Epimedium Herb

Cited by 27 publications

References 20 publications

New 8-prenylated quercetin glycosides from the flowers of Epimedium acuminatum and their testosterone production-promoting activities

New 8-prenylated quercetin glycosides from the flowers of Epimedium acuminatum and their testosterone production-promoting activities

Genome-wide analysis of UGT gene family identified key gene for the biosynthesis of bioactive flavonol glycosides in Epimedium pubescens Maxim.

Anhydroicaritin Inhibits EMT in Breast Cancer by Enhancing GPX1 Expression: A Research Based on Sequencing Technologies and Bioinformatics Analysis

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