Shipping to United States We Offer Worldwide Shipping
Login Wishlist

Quercetin 3-O-β-D-glucuronide

$431

  • Brand : BIOFRON

  • Catalogue Number : BD-P0645

  • Specification : 98.0%(HPLC)

  • CAS number : 22688-79-5

  • PUBCHEM ID : 5274585

  • Volume : 25mg

Available on backorder

Quantity
Checkout Bulk Order?

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

Applications

Miquelianin (Quercetin 3-O-glucuronide) is a metabolite of quercetin and a type of natural flavonoid.

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.

PMID

27257013

Abstract

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.

KEYWORDS

ERK; JNK; Lipopolysaccharide; Quercetin; Quercetin-3-O-β-D-glucuronide; RAW264.7 cells.

Title

Quercetin-3- O- β-D-Glucuronide Suppresses Lipopolysaccharide-Induced JNK and ERK Phosphorylation in LPS-Challenged RAW264.7 Cells

Author

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

Publish date

2016 Nov 1

PMID

27987489

Abstract

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.

KEYWORDS

ERK; JNK; Lipopolysaccharide; Quercetin; Quercetin-3-O-β-D-glucuronide; RAW264.7 cells.

Title

Enrichment and Separation of quercetin-3-O-β-d-glucuronide From Lotus Leaves (Nelumbo Nucifera Gaertn.) and Evaluation of Its Anti-Inflammatory Effect

Author

Fei Li 1 , Xiao-Yue Sun 1 , Xiao-Wei Li 1 , Tong Yang 1 , Lian-Wen Qi 2

Publish date

2017 Jan 15

PMID

30941276

Abstract

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.

KEYWORDS

Biotransformation; Isoquercitrin; Pharmacokinetic; Quercetin; Quercetin-3-O-β-D-glucuronide.

Title

Pharmacokinetic Comparison of Quercetin, Isoquercitrin, and quercetin-3-O-β-D-glucuronide in Rats by HPLC-MS

Author

Hongli Yin # 1 2 , Ji Ma # 2 , Jichun Han 1 , Maoru Li 3 , Jing Shang 1 2 3

Publish date

2019 Mar 26