Pinocembrin - CAS 480-39-7

Pinocembrin - CAS 480-39-7 Catalog number: BADC-00308

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Pinocembrin is a flavanoid with antioxidant activity found in damiana, honey, and propolis. Recent studies show that Pinocembrin maybe be a therapeutic option in reducing cerebral ischemia/reperfusion injury as a result of its anti-oxidative and anti-apoptotic effects.

Category
ADCs Cytotoxin
Product Name
Pinocembrin
CAS
480-39-7
Catalog Number
BADC-00308
Molecular Formula
C15H12O4
Molecular Weight
256.25
Pinocembrin

Ordering Information

Catalog Number Size Price Quantity
BADC-00308 10 mg $398
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Description
Pinocembrin is a flavanoid with antioxidant activity found in damiana, honey, and propolis. Recent studies show that Pinocembrin maybe be a therapeutic option in reducing cerebral ischemia/reperfusion injury as a result of its anti-oxidative and anti-apoptotic effects.
Synonyms
5,7-DIHYDROXYFLAVANONE; 5,7-DIHYDROXY-3'4'5'-FLAVANONE; 5,7-DIHYDROXY-2-PHENYL-CHROMAN-4-ONE; PINOCEMBRIN; (s)-2,3-dihydro-5,7-dihydroxy-2-phenyl-4h-1-benzopyran-4-one; 3-dihydro-5,7-dihydroxy-2-phenyl-(s)-4h-1-benzopyran-4-on; dihydrochrysin; galanginflavanone
IUPAC Name
(2S)-5,7-dihydroxy-2-phenyl-2,3-dihydrochromen-4-one
Canonical SMILES
C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=CC=C3
InChI
InChI=1S/C15H12O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-7,13,16-17H,8H2/t13-/m0/s1
InChIKey
URFCJEUYXNAHFI-ZDUSSCGKSA-N
Solubility
Chloroform, methanol, ethanol, acetone, not in water and hexane
Melting Point
194-195 °C
In Vitro
Pinocembrin inhibited LPS-induced productions of NO and PGE2, and also markedly inhibited TNF-α, IL-1β, iNOS, and COX-2 production in a concentration-dependent manner. In addition, TNF-α and IL-1β mRNA expression levels decreased significantly, while IL-10 mRNA expression increased (P < 0.05) with pinocembrin pre-treatment. RT-PCR and western blot analysis showed that pinocembrin decreased both the mRNA and protein expression levels of LPS-induced iNOS and COX-2 in HK macrophages. Pinocembrin suppressed the phosphorylation of MAPK in LPS-stimulated HK macrophages. Further, pinocembrin significantly inhibited LPS-induced NF-κB transcriptional activity via the attenuation of IκBα degradation.
In Vivo
Protection by pinocembrin was studied at the in vivo level using a model of middle cerebral artery occlusion and reperfusion in rats. Pinocembrin was administrated at the start of reperfusion. Pinocembrin markedly increased rat viability, reduced infarct volumes and neurological deficit scores in all treatment groups. Primary cortical neuronal cultures were subjected to oxygen-glucose deprivation/reoxygenation, a model of ischemia/reperfusion-like injury, and treated with pinocembrin at the start of reoxygenation. Neuronal survival rates were increased, LDH release was decreased and both neurite length and apoptosis were alleviated when pinocembrin was present during reoxygenation, and this protection was associated with the reduction of reactive oxygen species, nitric oxide and neuronal nitric oxide synthase (nNOS) and inducible NOS (iNOS), and an increase of glutathione. Moreover, DNA laddering was decreased in treatment groups of pinocembrin. Caspase-3 protein was down-regulated and PARP degradation was alleviated after pinocembrin treatments.
Clinical Trial Information
NCT NumberCondition Or DiseasePhaseStart DateSponsorStatus
NCT02059785Ischemic StrokePhase 22016-06-20CSPC ZhongQi Pharmaceutical Technology Co., Ltd.Suspended
Application
ADCs Cytotoxin
Appearance
Solid powder
Purity
≥ 95 % (HPLC).
Quantity
Milligrams-Grams
Quality Standard
Enterprise Standard
Shipping
Room temperature
Storage
Store at +4 °C, in dark place.
1.Dichloromethane extracts of propolis protect cell from oxygen-glucose deprivation-induced oxidative stress via reducing apoptosis.
Sun LP;Xu X;Hwang HH;Wang X;Su KY;Chen YL Food Nutr Res. 2016 Jun 20;60:30081. doi: 10.3402/fnr.v60.30081. eCollection 2016.
BACKGROUND: ;Bee propolis, a mixture of the secretion from bee tongue gland and wax gland, was collected from the tree bud and barked by bees. The components were rich in terpenes, phenolics, and flavonoids, and had anti-cancer, anti-bacterial, anti-inflammatory, hepatoprotective, and neuroprotection abilities. However, the potential anti-oxidative stress of propolis was not well documented. This study aimed to study the protective effect of propolis on high-incident nonfatal diseases, such as stroke and cerebral infarction caused by ischemia.;OBJECTIVE: ;Oxidative stress caused by acute stroke results in inflammation and injury followed by cell damage and apoptosis. Clarification of the anti-oxidative stress effect of propolis may contribute to stroke prevention and damage reduction.;DESIGN: ;Propolis was separated and purified into 70% ethanol and dichloromethane extracts systematically. The fraction three (Fr.3) of dichloromethane was further separated into pinocembrin, pinobanksin, pinobanksin-3-acetate, chrysin, and galangin by chromatography. Compounds extracted from propolis were tested for cell-protection effects in an oxygen-glucose deprivation (OGD) N2a cell model. MTT assay, oxidative stress markers measurement, flow cytometry, and QPCR were used to evaluate cell viability and apoptosis.
2.Main flavonoids, DPPH activity, and metal content allow determination of the geographical origin of propolis from the Province of San Juan (Argentina).
Lima B;Tapia A;Luna L;Fabani MP;Schmeda-Hirschmann G;Podio NS;Wunderlin DA;Feresin GE J Agric Food Chem. 2009 Apr 8;57(7):2691-8. doi: 10.1021/jf803866t.
The chemical characterization as well as the assessment of geographical origin of propolis from several areas of the Provincia de San Juan (Argentina) is reported. Chemical characterization of propolis was performed by measuring total phenolic (TP), total flavonoids (FL), free radical scavenging capacity (DPPH bleaching), and metal content in samples of six different districts. Methanolic propolis extracts (MEP) showed TP ranging from 25.7 to 39.3 g of gallic acid equivalents per 100 g of MEP, whereas flavonoids ranged from 6.6 to 13.3 g of quercetin equivalents per 100 g of MEP. Six main flavonoids were isolated and identified from the propolis samples, comprising the flavanones 7-hydroxy-8-methoxyflavanone (1), pinocembrin (2), and pinobanksin (3), the flavones chrysin (4) and tectochrysin (5), and the flavonol galangin (6). Compounds 1-6 were quantified by HPLC-PDA. Free radical scavenging activity, measured as percent DPPH bleaching, ranged from 46.6 to 89.5 at 10 mug/mL. Moreover, propolis samples presented high contents of Ca, K, Fe, Na, and Mg, but low amounts of Mn and Zn. Linear discriminant analysis affords eight descriptors, galangin, pinocembrin, pinobanksin, chrysin, tectochrysin, DPPH, K, and Na, allowing a clear distinction with 100% accuracy among different origins within the Provincia de San Juan.
3.Chemical characterization and cytotoxic activity evaluation of Lebanese propolis.
Noureddine H;Hage-Sleiman R;Wehbi B;Fayyad-Kazan H;Hayar S;Traboulssi M;Alyamani OA;Faour WH;ElMakhour Y Biomed Pharmacother. 2017 Nov;95:298-307. doi: 10.1016/j.biopha.2017.08.067. Epub 2017 Sep 12.
Chemical composition, anti-proliferative and proapoptotic activity as well as the effect of various fractions of Lebanese propolis on the cell cycle distribution were evaluated on Jurkat leukemic T-cells, glioblastoma U251 cells, and breast adenocarcinoma MDA-MB-231 cells using cytotoxic assays, flow cytometry as well as western blot analysis. Liquid chromatography-tandem mass spectrometry (LC-MS/MS) analysis revealed that ferulic acid, chrysin, pinocembrin, galangin are major constituents of the ethanolic crude extract of the Lebanese propolis, while the hexane fraction mostly contains chrysin, pinocembrin, galangin but at similar levels. Furthermore chemical analysis was performed using gas chromatography-mass spectrometry (GC-MS) to identify major compounds in the hexane fraction. Reduction of cell viability was observed in Jurkat cells exposed to the ethanolic crude extract and the hexane fraction, while viability of U251 and MDA-MB-231 cells was only affected upon exposure to the hexane fraction; the other fractions (aqueous phase, methylene chloride, and ethyl acetate) were without effect. Maximum toxic effect was obtained when Jurkat cells were cultivated with 90μg/ml of both the crude extract and hexane faction.

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