Isovitexin (or homovitexin, saponaretin) is a flavone, namely the apigenin-6-C-glucoside. In this case, the prefix 'iso' does not imply an isoflavonoid (the position of the B-ring on the C-ring), but the position of the glucoside on the flavone, in comparison to vitexin.
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InChI=1S/C21H20O10/c22-7-14-17(26)19(28)20(29)21(31-14)16-11(25)6-13-15(18(16)27)10(24)5-12(30-13)8-1-3-9(23)4-2-8/h1-6,14,17,19-23,25-29H,7H2/t14-,17-,19+,20-,21+/m1/s1 |
MYXNWGACZJSMBT-VJXVFPJBSA-N |
OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)c1c(O)cc2oc(cc(=O)c2c1O)-c1ccc(O)cc1 |
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EC 3.2.1.20 (alpha-glucosidase) inhibitor
An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of alpha-glucosidase (EC 3.2.1.20).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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View more via ChEBI Ontology
(1S)-1,5-anhydro-1-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-6-yl]-D-glucitol
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6-C-Glucosylapigenin
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KEGG COMPOUND
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6-Glucosylapigenin
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ChemIDplus
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Apigenin 6-C-glucoside
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KEGG COMPOUND
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Apigenin-6-C-glucoside
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KEGG COMPOUND
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beta-D-isovitexin
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ChEBI
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Isovitexin
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KEGG COMPOUND
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Saponaretin
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KEGG COMPOUND
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29702-25-8
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CAS Registry Number
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KEGG COMPOUND
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38953-85-4
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CAS Registry Number
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KEGG COMPOUND
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66651
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Reaxys Registry Number
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Reaxys
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Senol FS, Tuzun CY, Toker G, Orhan IE (2012) An in vitro perspective to cholinesterase inhibitory and antioxidant activity of five Gentiana species and Gentianella caucasea. International journal of food sciences and nutrition 63, 802-812 [PubMed:22475010] [show Abstract] The dichloromethane (DCM), ethyl acetate (EtOAc), and methanol extracts from the leaves, roots, and flowers of the five species of Gentiana (Gentiana asclepiadea, Gentiana cruciata, Gentiana olivieri, Gentiana septemfida, and Gentiana verna) and Gentianella caucasea were investigated for their inhibitory activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) and antioxidant effect using 2,2-diphenyl-1-picrylhydrazyl radical scavenging, metal-chelation capacity, and ferric-reducing antioxidant power assays. Total phenol and flavonoid contents of the extracts were determined spectrophotometrically. The presence of some characteristic compounds found in Gentiana species (gentiopicroside, swertiamarin, isoorientin, isovitexin and vitexin) was analyzed in the extracts by thin layer chromatography. The flower DCM extract of G. verna exerted the highest inhibition against AChE (53.65 ± 1.03%), whereas the root EtOAc extract of G. cruciata was the most effective in BChE inhibition assay (50.72 ± 0.75%) at 100 μg ml⁻¹. The extracts of G. verna were also found to be more active in the antioxidant tests. | Ma X, Yan R, Yu S, Lu Y, Li Z, Lu H (2012) Enzymatic acylation of isoorientin and isovitexin from bamboo-leaf extracts with fatty acids and antiradical activity of the acylated derivatives. Journal of agricultural and food chemistry 60, 10844-10849 [PubMed:23057589] [show Abstract] This study enzymatically acrylates two flavonoids from bamboo-leaf extracts, isoorientin and isovitexin, with different fatty acids as acyl donors using Candida antarctica lipase B (CALB). The conversion yield ranged from 35 to 80% for fatty acids with different chain lengths. Higher isoorientin and isovitexin conversion yields (>75%) were obtained using lauric acid in tert-amyl-alcohol as the reaction medium. (1)H and (13)C nuclear magnetic resonance spectroscopy analysis showed that, in the presence of CALB, acylation occurred at the isoorientin and isovitexin primary hydroxyl group of glucose moiety and only monoesters were detected. Introducing an acyl group into isoorientin and isovitexin significantly improved their lipophilicity but reduced their antiradical activity. | Choo CY, Sulong NY, Man F, Wong TW (2012) Vitexin and isovitexin from the Leaves of Ficus deltoidea with in-vivo α-glucosidase inhibition. Journal of ethnopharmacology 142, 776-781 [PubMed:22683902] [show Abstract]
Ethnopharmacological relevanceThe leaves of Ficus deltoidea are used as a traditional medicine by diabetes patients in Malaysia.Aim of the studyThe objective of the study is to identify and evaluate bioactive constituents with in vivo α-glucosidase inhibition.Materials and methodsThe partitioned extracts, subfractions and pure bioactive constituents were subjected to α-glucosidase inhibition assay. The identified bioactive constituents were administered orally to sucrose loaded normoglycemic mice and induced diabetic rats. The postprandial blood glucose levels were monitored at 30 min interval. Acute toxicity was evaluated in both normoglycemic mice and induced diabetic rats.ResultsBioactivity guided fractionation led to the isolation of both vitexin (1) and isovitexin (2). Oral administration of 1mg/kg of either vitexin (1) or isovitexin (2) significantly (p<0.05) reduced the postprandial blood glucose level in sucrose loaded normoglycemic mice at 30 min. The percentage of postprandial blood glucose reduction was highest in sucrose loaded induced diabetic rats administered orally with 200mg/kg of vitexin (1) or 100mg/kg of isovitexin (2). Both vitexin (1) and isovitexin (2) did not exert any signs of toxicity at the highest dose of 2g/kg administered orally to normoglycemic mice and induced diabetic rats.ConclusionBoth the C-glycosyl bioflavonoids, namely, vitexin (1) and isovitexin (2) exhibited in vivo α-glucosidase inhibition. | Lin CM, Huang ST, Liang YC, Lin MS, Shih CM, Chang YC, Chen TY, Chen CT (2005) Isovitexin suppresses lipopolysaccharide-mediated inducible nitric oxide synthase through inhibition of NF-kappa B in mouse macrophages. Planta medica 71, 748-753 [PubMed:16142640] [show Abstract] Isovitexin exhibits potent antioxidant activities. In this study, the activity of nitric oxide synthase (iNOS) in lipopolysaccharide (LPS)-activated RAW264.7 macrophages after incubation with isovitexin was investigated. Isovitexin was able to reduce the production of hydrogen peroxide induced by LPS in mouse macrophage RAW264.7 cells. The cells incubated with isovitexin had markedly reduced LPS-stimulated NO production with an IC (50) value of 58.5 microM. The expression of iNOS was also inhibited when the cells were treated with isovitexin. A transient transfection experiment showed that isovitexin suppressed the iNOS promoter and NF-kappaB-dependent transcriptional activities. It was also found to inhibit IKK kinase activity and prevent the degradation of IkappaBalpha in activated RAW264.7 cells. Additionally, Western blotting analysis revealed that isovitexin prevented the translocation of NF-kappaB from the cytoplasm to the nucleus. Our results indicate that its ROS scavenger and IKK inhibitory activities also contribute to the suppression of ROS-mediated NF-kappaB activity. These results suggest that isovitexin, a food phytochemical contained in dietary rice products, might have biological significance. |
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