Apigenin-7-glucuronide
(Synonyms: 芹菜素-7-葡萄糖醛酸,Apigenin 7-O-glucuronide) 目录号 : GC35369Apigenin-7-O-glucuronide (Apigenin-7-glucuronide) is the major flavonoid found in milk thistle. Apigenin 7-o-glucuronide inhibits tumor necrosis factor alpha (TNF-α) and total nitrite release in lipopolysaccharide-activated macrophages.
Cas No.:29741-09-1
Sample solution is provided at 25 µL, 10mM.
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Apigenin-7-O-glucuronide (Apigenin-7-glucuronide) is the major flavonoid found in milk thistle. Apigenin 7-o-glucuronide inhibits tumor necrosis factor alpha (TNF-α) and total nitrite release in lipopolysaccharide-activated macrophages.
[1] Carla Marrassini, et al. Evid Based Complement Alternat Med . 2020 Dec 2;2020:6638764.
Cas No. | 29741-09-1 | SDF | |
别名 | 芹菜素-7-葡萄糖醛酸,Apigenin 7-O-glucuronide | ||
Canonical SMILES | O[C@H]([C@H]([C@@H]([C@@H](C(O)=O)O1)O)O)[C@@H]1OC2=CC(O)=C3C(C=C(C4=CC=C(O)C=C4)OC3=C2)=O | ||
分子式 | C21H18O11 | 分子量 | 446.36 |
溶解度 | DMSO: 65 mg/mL (145.62 mM) | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg | |
1 mM | 2.2403 mL | 11.2017 mL | 22.4034 mL |
5 mM | 0.4481 mL | 2.2403 mL | 4.4807 mL |
10 mM | 0.224 mL | 1.1202 mL | 2.2403 mL |
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Apigenin-7-glucuronide from Urera aurantiaca Inhibits Tumor Necrosis Factor Alpha and Total Nitrite Release in Lipopolysaccharide-Activated Macrophages
Evid Based Complement Alternat Med 2020 Dec 2;2020:6638764.PMID:33343677DOI:10.1155/2020/6638764.
Urera aurantiaca is an Argentinean medicinal and edible species traditionally used to treat symptoms of inflammation. The aim of this study was to evaluate the anti-inflammatory activity of a methanol extract and its major compound. U. aurantiaca aerial parts were extracted with methanol by maceration. A phytochemical analysis was performed, and the extract's major component, Apigenin-7-glucuronide (A7G), was identified by spectroscopic and HPLC methods. The analysis of the inflammatory mediators nitric oxide (NO) and tumor necrosis factor alpha (TNF-α) in lipopolysaccharide- (LPS-) stimulated macrophages were used in the evaluation of the extract and the major compound anti-inflammatory effects. The extract reduced LPS-augmented NO release from 100 μg/mL (27%), reaching the highest inhibition at 1000 μg/mL (96.3%), while A7G reduced it 30.7% at 1 μg/mL, and its maximum effect was 97.1% at 10 μg/mL. In the TNF-α model, the extract at 500 and 1000 μg/mL reduced LPS-augmented TNF-α by 13.5% and 93.9%, respectively; meanwhile, A7G reduced it by 26.2% and 83.8% at 5 and 10 μg/mL, respectively. U. aurantiaca popular use was validated. In the present study, for the first time, A7G was isolated from U. aurantiaca; furthermore, A7G showed anti-inflammatory effect in the macrophage cell line RAW264.7 (ATCC) and seems to be responsible for the extract anti-inflammatory effect.
Absorption, distribution, metabolism and excretion of apigenin and its glycosides in healthy male adults
Free Radic Biol Med 2022 May 20;185:90-96.PMID:35452808DOI:10.1016/j.freeradbiomed.2022.04.007.
The bioavailability of apigenin and its O-glycosides in humans was investigated with apigenin-4'-glucuronide (Ap-4'-GlcUA), Apigenin-7-glucuronide and apigenin-7-sulfate being identified as in vivo metabolites. Apigenin per se was poorly absorbed with metabolites equivalent to 0.5% of intake excreted in urine 0-24 h post-intake. Consumption of a parsley drink containing apigenin-7-O-(2″-O-apiosyl)glucoside resulted in the peak plasma concentration (Cmax) of Ap-4'-GlcUA occurring after 4 h, indicative of absorption in the lower gastrointestinal tract (GIT). Urinary excretion of the three metabolites corresponded to 11.2% of intake. Ingestion of dried powdered parsley leaves with yogurt extended the Cmax of Ap-4'-GlcUA to 6 h. Consumption of chamomile tea containing apigenin-7'-O-glucoside resulted in a 2 h Cmax of Ap-4'-GlcUA, in keeping with absorption in the upper GIT. Urinary excretion was equivalent to 34% of intake. Intake of the parsley drink provided information on intra- and inter-individual variations in the level of excretion of the apigenin metabolites. CLINICAL TRAIL REGISTRATION NUMBER: This trail was registered at clinicaltrials.gov as NCT03526081.
Comparative antioxidant activity and HPLC profiles of some selected Korean thistles
Arch Pharm Res 2008 Jan;31(1):28-33.PMID:18277604DOI:10.1007/s12272-008-1116-7.
As yet, no comparative analyses have been conducted regarding the comparative antioxidant activities and HPLC profiles of thistles distributed in Korea. Thus, this study was performed in order to evaluate the antioxidant potentials of seven Korean thistles: Cirsium lineare, Cirsium chanroenicum, Cirsium setidens, Cirsium japonicum var. ussuriense, Cirsium nipponicum, Cirslum pendulum and Carduus crispus, via peroxynitrite and DPPH free radical assays. Among seven Korean thistles, Carduus crispus exhibited the most significant antioxidant activity in both DPPH assay and peroxynitrite. In order to characterize the compounds contained in Korean thistles, we conducted HPLC analyses on the following ten flavonoids: luteolin-5-glucoside (1), luteolin-7-glucoside (2), apigenin-7-glucoside (3), hispidulin-7-neohesperidoside (4), Apigenin-7-glucuronide (5), cirsimarin (6), pectolinarin (7), luteolin (8), apigenin (9) and acacetin (10). The results of our HPLC analyses indicated the presence of pectolinarin in the whole plants of C. setidens, C. lineare, C. nipponicum, C. pendulum, the aerial and underground parts of C. japonicum var. ussuriense, and the aerial parts of C. chanroenicum. Moreover, we were able to identify hispidulin-7-neohesperidoside and luteolin-7-glucoside in the whole plants of Carduus crispus, acacetin in the aerial parts of C. chanroenicum, cirsimarin in C. lineare.
Metabolomics-based profiling of 4 avocado varieties using HPLC-MS/MS and GC/MS and evaluation of their antidiabetic activity
Sci Rep 2022 Mar 23;12(1):4966.PMID:35322072DOI:10.1038/s41598-022-08479-4.
Seven avocado "Persea americana" seeds belonging to 4 varieties, collected from different localities across the world, were profiled using HPLC-MS/MS and GC/MS to explore the metabolic makeup variabilities and antidiabetic potential. For the first time, 51 metabolites were tentatively-identified via HPLC-MS/MS, belonging to different classes including flavonoids, biflavonoids, naphthodianthrones, dihydrochalcones, phloroglucinols and phenolic acids while 68 un-saponified and 26 saponified compounds were identified by GC/MS analysis. The primary metabolic variabilities existing among the different varieties were revealed via GC/MS-based metabolomics assisted by unsupervised pattern recognition methods. Fatty acid accumulations were proved as competent, and varietal-discriminatory metabolites. The antidiabetic potential of the different samples was explored using in-vitro amylase and glucosidase inhibition assays, which pointed out to Gwen (KG) as the most potent antidiabetic sample. This could be attributed to its enriched content of poly-unsaturated fatty acids and polyphenolics. Molecular docking was then performed to predict the most promising phytoligands in KG variety to be posed as antidiabetic drug leads. The highest in-silico α-amylase inhibition was observed with chrysoeriol-4'-O-pentoside-7-O-rutinoside, Apigenin-7-glucuronide and neoeriocitrin which might serve as potential drug leads for the discovery of new antidiabetic remedies.
Antimicrobial activity and molecular docking screening of bioactive components of Antirrhinum majus (snapdragon) aerial parts
Heliyon 2022 Aug 27;8(8):e10391.PMID:36072262DOI:10.1016/j.heliyon.2022.e10391.
Background: Antirrhinum majus (Snapdragon) is a perennial Mediterranean-native plant that is commonly used for mass display. Few reports acknowledged the traditional use of A. majus for its medicinal and therapeutic effects. Herein, we assess the impact of A. majus's sample preparation and extraction methods on the plant-aerial parts' phytochemical contents and antimicrobial activity. Furthermore, the microbial targets of the extracts' secondary metabolites are inspected using molecular docking simulations. Methods: The leaves and flowers of A. majus were prepared as fresh and air-dried samples, then extracted using cold maceration and hot reflux, respectively. Extracts with the best phytochemical profiles were selected to test their antimicrobial activities against Bacillus subtilis, Staphylococcus aureus, Enterobacter aerogenes, Escherichia coli and Candida albicans. Besides, molecular docking of 66 reported isolated compounds was conducted against various microbial targets. Results: The dried-refluxed samples revealed a massive deterioration in their phytochemical profiles, whereas the macerated flowers extract exhibited the highest total phenolic content and antimicrobial activity against all tested bacterial strains. However, both flowers and leaves extracts showed similar minimum inhibitory and lethal concentrations against C. albicans. Molecular docking studies revealed that chlorogenic acid, chalcononaringenin 4'-glucoside, 3,4,2',4',6'-pentahydroxy-chalcone 4'-glucoside, Apigenin-7-glucuronide, and luteolin-7-glucuronide were the lead compounds in expressing the antimicrobial activity. Yet, A. majus's compounds could neither inhibit the 30S ribosomal subunit nor muramyl ligase E. Conclusion: Our results suggest that cold maceration of A. majus fresh aerial parts gave higher flavonoid and phenolic content contributing to its antimicrobial properties. These flavonoids and phenolic compounds are predicted to have a crucial role in inhibiting fungal sterol 14-demethylase, and bacterial dihydropteroate synthase and gyrase B subunit proteins.