Orientin is a flavone, a chemical flavonoid-like compound. It is the 8-C glucoside of luteolin.
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InChI=1S/C21H20O11/c22-6-14-17(28)18(29)19(30)21(32-14)16-11(26)4-10(25)15-12(27)5-13(31-20(15)16)7-1-2-8(23)9(24)3-7/h1-5,14,17-19,21-26,28-30H,6H2/t14-,17-,18+,19-,21+/m1/s1 |
PLAPMLGJVGLZOV-VPRICQMDSA-N |
OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)c1c(O)cc(O)c2c1oc(cc2=O)-c1ccc(O)c(O)c1 |
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antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
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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
2-(3,4-dihydroxyphenyl)-8-β-D-glucopyranosyl-5,7-dihydroxy-4H-chromen-4-one
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8-β-D-glucosylluteolin
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ChEBI
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Luteolin 8-C-glucoside
Note: (2007-02-13) Misnomer: IUPAC strongly discourages the use of names based on 'C-glycoside' terminology. |
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KEGG COMPOUND
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Lutexin
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HMDB
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Orientin
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KEGG COMPOUND
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28608-75-5
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CAS Registry Number
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ChemIDplus
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69376
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Reaxys Registry Number
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Reaxys
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Simirgiotis MJ, Schmeda-Hirschmann G, Bórquez J, Kennelly EJ (2013) The Passiflora tripartita (Banana Passion) fruit: a source of bioactive flavonoid C-glycosides isolated by HSCCC and characterized by HPLC–DAD–ESI/MS/MS. Molecules (Basel, Switzerland) 18, 1672-1692 [PubMed:23358325] [show Abstract] The banana passion fruit (Passiflora tripartita Breiter, Passifloraceae) known as "tumbo" is very appreciated in tropical and subtropical countries of South America. Methanolic extracts from peel and the fruit juice of P. tripartita growing in Chile were analyzed for antioxidant capacity as well as for flavonoid and phenolic content. A chromatographic method was developed for the rapid identification of the main phenolics in the samples by HPLC-DAD and HPLC-MS. The fast fingerprint analysis allowed the detection of eighteen flavonoid C-glycosides and four flavonoid O-glycoside derivatives which were characterized by UV spectra and ESI-MS-MS analysis. Several of the C-glycosides detected are structurally related to the orientin derivative 4'-methoxy-luteolin-8-C-(6"acetyl)-b-D-glucopyranoside (31), fully elucidated by spectroscopic methods. The antioxidant derivative 31 along with schaftoside, vicenin II, orientin and vitexin were isolated from the fruit extract by high-speed countercurrent chromatography (HSCCC). A suitable method for the preparative isolation of flavonol C-glycosides from "tumbo" extracts by HSCCC is reported. The pulp of the fruits showed good antioxidant capacity (12.89 ± 0.02 mg/mL in the DPPH assay). The peel presented the highest content of flavonoids (56.03 ± 4.34 mg quercetin/100 g dry weight) which is related to the highest antioxidant power (10.41 ± 0.01 mg/mL in the DPPH assay). | Khan RA (2012) Evaluation of flavonoids and diverse antioxidant activities of Sonchus arvensis. Chemistry Central journal 6, 126 [PubMed:23107458] [show Abstract]
UnlabelledBackgroundSonchus arvensis is used in the treatment of various human aliments as a traditional medicine in Pakistan. In the study its various fractions are characterized for scavenging of diverse free radicals.ResultsResults of the present study revealed that various fractions of Sonchus arvensis significantly scavenged the free radicals (DPPH·, ABTS·+, ·OH, superoxide), however its methanolic fraction is more potent than other fractions. Significant correlation was found between DPPH·, ABTS·+, superoxide radical and total antioxidant activity with total flavonoids and phenolics contents. Phytochmical analysis revealed the presence kaempferol, quercetin, orientin, rutin, hyperoside, catechin and myricetin.ConclusionFrom the present data it is concluded that various fractions of Sonchus arvensis significantly scavenged the free radical, which might be due the presence of polyphenolic constituent. | Mali VR, Mohan V, Bodhankar SL, Bodhankar SL (2012) Antihypertensive and cardioprotective effects of the Lagenaria siceraria fruit in NG-nitro-L-arginine methyl ester (L-NAME) induced hypertensive rats. Pharmaceutical biology 50, 1428-1435 [PubMed:22994444] [show Abstract]
ContextLagenaria siceraria (Molina) Standl. (Cucurbitacae) (LS) has been reported to possess cardioprotective, antihyperlipidemic, and diuretic activities.ObjectiveTo evaluate antihypertensive and cardioprotective effects of the Lagenaria siceraria fruit powder in N(G)-nitro-L-arginine methyl ester (L-NAME) induced hypertension in rats.Materials and methodsMale Wistar rats were divided in four groups. Control 2% gum acacia p.o., L-NAME (40 mg/kg p.o.), LS (500 mg/kg p.o.) + L-NAME (40 mg/kg p.o.), L-arginine (100 mg/kg p.o.) + L-NAME (40 mg/kg p.o.). Treatment period was 4 weeks. On day 29 serum marker enzymes, cholesterol and heamodynamic parameters were measured. Histology of heart was performed. LS powder was characterized by HPLC.ResultSystolic blood pressures were increased by L-NAME (p < 0.001). In both drug treated groups systolic and diastolic blood pressures were reduced significantly (p < 0.001) compared to L-NAME. In L-NAME group significantly (p < 0.01) elevated cholesterol which was reduced (p < 0.05) by LS treatment. In L-NAME group inflammation and necrosis (0-35%) was present in heart whereas there was no change in myocardium of LS and L-arginine treated rats. Vitexin, orientin and isoorientin were detected in methanol extract of LS powder.Discussion and conclusionL-NAME induced hypertension in rats was reduced by treatment with LS. The absence of necrosis, inflammation in the heart and significant reduction in serum cholesterol in LS and L-arginine treated rats indicated cardioprotective activity. Antioxidant activity of orientin and isoorientin appears to reduce the L-NAME induced damage. It is concluded that LS fruit possess antihypertensive and cardioprotective activity. | Kim HJ, Park KJ, Lim JH (2011) Metabolomic analysis of phenolic compounds in buckwheat (Fagopyrum esculentum M.) sprouts treated with methyl jasmonate. Journal of agricultural and food chemistry 59, 5707-5713 [PubMed:21417394] [show Abstract] The effects of exogenous methyl jasmonate (MeJA) on phytochemical production in buckwheat sprouts cultivated under dark conditions (0, 1, 3, 5, and 7 d) were investigated by metabolomic analysis, using ultra performance liquid chromatography-quadrupole-time-of-flight (UPLC-Q-TOF) mass spectroscopy (MS) and partial least-squares-discriminant analysis (PLS-DA). MeJA-treated and control groups showed no differences in growth but were clearly discriminated from each other on PLS-DA score plots. The metabolites contributing to the discrimination were assigned as chlorogenic acid, catechin, isoorientin, orientin, rutin, vitexin, and quercitrin, which have various health effects. Moreover, isoorientin, orientin, rutin, and vitexin were assigned as the main phytochemicals of sprouts cultivated under dark conditions. The accumulation of these metabolites caused the phenolic compound content and antioxidant activity of the sprouts to increase. Further, this study revealed that their accumulation resulted from the stimulation of the phenylpropanoid pathway by MeJA treatment. Therefore, these metabolites may be useful for better understanding the effects of MeJA on buckwheat sprout phytochemicals and contribute to improving the functional quality of the sprouts. | Lu N, Sun Y, Zheng X (2011) Orientin-induced cardioprotection against reperfusion is associated with attenuation of mitochondrial permeability transition. Planta medica 77, 984-991 [PubMed:21283956] [show Abstract] In this study, we provide new evidence that orientin from bamboo leaves (Phyllostachys nigra) protect H9c2 cardiomyocytes against ischemia/reperfusion (I/R) injury through the mitochondrial apoptotic pathway. A previous work has identified that orientin could protect myocardium against ischemia/reperfusion injury. Mitochondria are both critical determinants of cardioprotection and crucial targets of cardioprotective signaling. Their role during reperfusion is conspicuously critical because the conditions promote apoptosis through the mitochondrial pathway and necrosis though irreversible damage to mitochondria, which is in association with mitochondrial permeability transition (MPT). After myocardial ischemia, opening of the mPTP is a critical determinant of cell death. The relationship of orientin and mPTP in mediating reperfusion-induced cardiomyocytes injury is still elusive. Here, our results indicate that the protective effect of orientin in H9c2 cells subjected to I/R injury is associated with depression of the mPTP opening, resultant mitochondrial dysfunction, and apoptosis. Further investigation of cellular mechanisms revealed that these effects were associated with inhibition of reactive oxygen species (ROS) generation, repolarization of mitochondrial membrane potential (Δψ(m)), suppression of mitochondrial cytochrome C release, enhancement of the Bcl-2 level, and inhibition of Bax and Smac/DIABLO levels. Furthermore, these beneficial effects of orientin were blocked by the phosphatidylinositol 3-kinase (PI3K) inhibitor wortmannin, and orientin could enhance Akt phosphorylation. In summary, we demonstrate that orientin protects H9c2 cardiomytocytes against I/R-induced apoptosis by modulating the mPTP opening, and this role of orientin may involve the PI3K/Akt signaling pathway. |
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