Catalogue Number
BD-P0645
Analysis Method
HPLC,NMR,MS
Specification
98.0%(HPLC)
Storage
-20℃
Molecular Weight
Appearance
Yellow powder
Botanical Source
Structure Type
Flavonoids
Category
Standards;Natural Pytochemical;API
SMILES
C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)C(=O)O)O)O)O)O)O
Synonyms
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3-(β-D-glucopyranuronosyloxy)-5,7-dihydroxy-/Querciturone/Quercetin-3-O-glucuronide/Quercetin-3-O-β-D-glucuronopyranoside/Miquelianin/quercetin 3-O-glucuronide/Quercetin 3-O-β-D-glucuronide/Quercetin-3-Glucuronide/2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl β-D-glucopyranosiduronic acid/Quercetin 3-glucuronide/Miquelianin (Quercetin 3-O-glucuronide)
IUPAC Name
(2S,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
Density
2.0±0.1 g/cm3
Solubility
Methanol; DMF
Flash Point
325.8±27.8 °C
Boiling Point
927.8±65.0 °C at 760 mmHg
Melting Point
InChl
InChI=1S/C21H18O13/c22-7-4-10(25)12-11(5-7)32-17(6-1-2-8(23)9(24)3-6)18(13(12)26)33-21-16(29)14(27)15(28)19(34-21)20(30)31/h1-5,14-16,19,21-25,27-29H,(H,30,31)/t14-,15-,16+,19-,21+/m0/s1
InChl Key
DUBCCGAQYVUYEU-ZUGPOPFOSA-N
WGK Germany
RID/ADR
HS Code Reference
2938900000
Personal Projective Equipment
Correct Usage
For Reference Standard and R&D, Not for Human Use Directly.
Meta Tag
provides coniferyl ferulate(CAS#:22688-79-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate
No Technical Documents Available For This Product.
27257013
Quercetin, a flavonol, has been reported to exhibit a wide range of biological properties including anti-oxidant and anti-inflammatory activities. However, pharmacological properties of quercetin-3-O-β-D-glucuronide (QG), a glycoside derivative of quercetin, have not been extensively examined. The objective of this study is to elucidate the anti-inflammatory property and underlying mechanism of QG in lipopolysaccharide (LPS)-challenged RAW264.7 macrophage cells in comparison with quercetin. QG significantly suppressed LPS-induced extracellular secretion of pro-inflammatory mediators such as nitric oxide (NO) and PGE₂, and pro-inflammatory protein expressions of iNOS and COX-2. To elucidate the underlying mechanism of the anti-inflammatory property of QG, involvement of MAPK signaling pathways was examined. QG significantly attenuated LPS-induced activation of JNK and ERK in concentration-dependent manners with a negligible effect on p38. In conclusion, the present study demonstrates QG exerts anti-inflammatory activity through the suppression of JNK and ERK signaling pathways in LPS-challenged RAW264.7 macrophage cells.
ERK; JNK; Lipopolysaccharide; Quercetin; Quercetin-3-O-β-D-glucuronide; RAW264.7 cells.
Quercetin-3- O- β-D-Glucuronide Suppresses Lipopolysaccharide-Induced JNK and ERK Phosphorylation in LPS-Challenged RAW264.7 Cells
Jin-Young Park 1 , Man-Sup Lim 1 , Song-In Kim 1 , Hee Jae Lee 1 , Sung-Soo Kim 1 , Yong-Soo Kwon 2 , Wanjoo Chun 1
2016 Nov 1
27987489
This work aimed to establish a systematic strategy to enrich and separate quercetin-3-O-β-d-glucuronide (Q3GA) from lotus leaves with macroporous resin and semi-preparative HPLC. Six resins were tested, and LX-5 was chosen as the appropriate resin for Q3GA based on the adsorption and desorption performances. After one-step enrichment, the content of Q3GA increased from 2.15% in crude extract to 52.25% in 30% ethanol fraction with yield of 11.97%. The Q3GA was then isolated from the 30% ethanol fraction by semi-preparative HPLC, and the purity of Q3GA was above 98.00% with yield of 19.76%. These results suggested that the aforementioned strategy was a useful and economic method to enrich and separate Q3GA from lotus leaves. Additionally, the anti-inflammatory effect of Q3GA was evaluated in lipopolysaccharide-treated RAW264.7 macrophages, and the result demonstrated that Q3GA could significantly inhibit LPS-induced NO release in vitro in a dose-dependent manner compared with control group.
ERK; JNK; Lipopolysaccharide; Quercetin; Quercetin-3-O-β-D-glucuronide; RAW264.7 cells.
Enrichment and Separation of quercetin-3-O-β-d-glucuronide From Lotus Leaves (Nelumbo Nucifera Gaertn.) and Evaluation of Its Anti-Inflammatory Effect
Fei Li 1 , Xiao-Yue Sun 1 , Xiao-Wei Li 1 , Tong Yang 1 , Lian-Wen Qi 2
2017 Jan 15
30941276
Background: Quercetin (Qr), isoquercitrin (IQ), and quercetin-3-O-β-D-glucuronide (QG) are powerful phytochemicals that have been shown to exhibit disease prevention and health promotion properties. However, there may exist transformations between Qr, IQ, and QG in vivo. And the pharmacokinetic profiles of Qr, IQ, and QG have not been systematically compared. The pharmacokinetics study would be helpful to better understand the pharmacological actions of them.
Methods: Herein, we developed a reliable HPLC-MS method to compare the pharmacokinetics of Qr, IQ, and QG after separate (50 mg/kg) oral administration of them in rats, using puerarin as internal standard. The detection was performed using negative selected ion monitoring. This method was validated in terms of selectivity, linearity, precision, accuracy, extraction recovery, matrix effect, and stability; and shows reliabilities in monitoring the pharmacokinetic behaviors of these three compounds.
Results: Our results showed that after separate oral administration of Qr, IQ, and QG, all of the compounds could be detected in plasma. In addition, QG could be detected in the Qr group; Qr and QG could be measured in the IQ group; and Qr could be found in rat plasma after 1.5 h of QG administration. Moreover, the AUC0-t of Qr in the; Qr group (2,590.5 ± 987.9 mg/L*min), IQ group (2,212.7 ± 914.1 mg/L*min), and QG group (3,505.7 ± 1,565.0 mg/L*min) was larger than the AUC0-t of QG in the; Qr group (1,550.0 ± 454.2 mg/L*min), IQ group (669.3 ± 188.3 mg/L*min), and QG group (962.7 ± 602.3 mg/L*min). The AUC0-t of IQ was the lowest among all groups.
Discussion: Quercetin, IQ, and QG can all be absorbed into plasma. A mutual transformation exists between Qr and QG, and IQ can be metabolized into Qr and QG in SD rats. These results would provide a meaningful basis for understanding the pharmacological actions of these three compounds.
Biotransformation; Isoquercitrin; Pharmacokinetic; Quercetin; Quercetin-3-O-β-D-glucuronide.
Pharmacokinetic Comparison of Quercetin, Isoquercitrin, and quercetin-3-O-β-D-glucuronide in Rats by HPLC-MS
Hongli Yin # 1 2 , Ji Ma # 2 , Jichun Han 1 , Maoru Li 3 , Jing Shang 1 2 3
2019 Mar 26
