Quercitrin
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MedKoo CAT#: 461290

CAS#: 522-12-3

Description: Quercitrin is an antibacterial agent and has been shown to inhibit the oxidation of low-density lipoproteins and prevent an allergic reaction.

Chemical Structure

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Quercitrin
CAS# 522-12-3
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 461290
Name: Quercitrin
CAS#: 522-12-3
Chemical Formula: C21H20O11
Exact Mass: 448.10
Molecular Weight: 448.380
Elemental Analysis: C, 56.25; H, 4.50; O, 39.25

Price and Availability

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25mg USD 700
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Synonym: Quercitrin; Thujin;

IUPAC/Chemical Name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

InChi Key: OXGUCUVFOIWWQJ-HQBVPOQASA-N

InChi Code: InChI=1S/C21H20O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-18,21-26,28-29H,1H3/t7-,15-,17+,18+,21-/m0/s1

SMILES Code: O=C1C(O[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)O)O)=C(C3=CC=C(O)C(O)=C3)OC4=CC(O)=CC(O)=C14

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, DMF, and ethanol

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Product Data:
Product Data
Instruction:
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Biological target: Quercitrin is a quercetin O-glycoside, quercetin substituted by a alpha-L-rhamnosyl moiety at position 3 via a glycosidic linkage. It has a role as an antioxidant, an antileishmanial agent, a carbonyl reductase (NADPH) inhibitor, an aldehyde reductase inhibitor, an tyrosinase inhibitor, and a plant metabolite.
In vitro activity: Purified quercitrin inhibited the polymerisation of isolated HbS and stabilized sickle erythrocytes membranes in cell cultures with sickle cells. Metabolomic comparisons of blood samples using flow-infusion electrospray-high resolution mass spectrometry indicated that quercitrin could convert HbSS erythrocyte metabolomes to be like HbAA. Sickling was associated with changes in antioxidants, anaerobic bioenergy, and arachidonic acid metabolism, all of which were reversed by quercitrin. This points to the development of an anti-sickling drug or quality control assessments of A. cordifolia preparations. Reference: J Clin Med. 2022 Apr 13;11(8):2177. https://pubmed.ncbi.nlm.nih.gov/35456270/
In vivo activity: Diets rich in quercitrin show a neuroprotective effect, and the objective of this study was to explore the effect and mechanism of quercitrin in the treatment of alzheimer's disease (AD). Quercitrin improved 5XFAD transgenic mice cognitive impairment through alleviating the intensity of inflammatory response and is a promising medicinal plant extract in the treatment of AD. Reference: . Neuroreport. 2022 May 18;33(8):327-335. https://pubmed.ncbi.nlm.nih.gov/35594435/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 30.0 66.91
DMF 15.0 33.45
Ethanol 1.0 2.23

Preparing Stock Solutions

The following data is based on the product molecular weight 448.38 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Adeniyi O, Baptista R, Bhowmick S, Cookson A, Nash RJ, Winters A, Shen J, Mur LAJ. Isolation and Characterisation of Quercitrin as a Potent Anti-Sickle Cell Anaemia Agent from Alchornea cordifolia. J Clin Med. 2022 Apr 13;11(8):2177. doi: 10.3390/jcm11082177. PMID: 35456270; PMCID: PMC9024604. 2. Tang J, Diao P, Shu X, Li L, Xiong L. Quercetin and Quercitrin Attenuates the Inflammatory Response and Oxidative Stress in LPS-Induced RAW264.7 Cells: In Vitro Assessment and a Theoretical Model. Biomed Res Int. 2019 Oct 28;2019:7039802. doi: 10.1155/2019/7039802. PMID: 31781635; PMCID: PMC6855062. 3. Wang L, Sun J, Miao Z, Jiang X, Zheng Y, Yang G. Quercitrin improved cognitive impairment through inhibiting inflammation induced by microglia in Alzheimer's disease mice. Neuroreport. 2022 May 18;33(8):327-335. doi: 10.1097/WNR.0000000000001783. Epub 2022 Apr 8. PMID: 35594435; PMCID: PMC9223515. 4. Xiong W, Yuan Z, Wang T, Wu S, Xiong Y, Yao Y, Yang Y, Wu H. Quercitrin Attenuates Acetaminophen-Induced Acute Liver Injury by Maintaining Mitochondrial Complex I Activity. Front Pharmacol. 2021 May 5;12:586010. doi: 10.3389/fphar.2021.586010. PMID: 34025394; PMCID: PMC8131832.
In vitro protocol: 1. Adeniyi O, Baptista R, Bhowmick S, Cookson A, Nash RJ, Winters A, Shen J, Mur LAJ. Isolation and Characterisation of Quercitrin as a Potent Anti-Sickle Cell Anaemia Agent from Alchornea cordifolia. J Clin Med. 2022 Apr 13;11(8):2177. doi: 10.3390/jcm11082177. PMID: 35456270; PMCID: PMC9024604. 2. Tang J, Diao P, Shu X, Li L, Xiong L. Quercetin and Quercitrin Attenuates the Inflammatory Response and Oxidative Stress in LPS-Induced RAW264.7 Cells: In Vitro Assessment and a Theoretical Model. Biomed Res Int. 2019 Oct 28;2019:7039802. doi: 10.1155/2019/7039802. PMID: 31781635; PMCID: PMC6855062.
In vivo protocol: 1. Wang L, Sun J, Miao Z, Jiang X, Zheng Y, Yang G. Quercitrin improved cognitive impairment through inhibiting inflammation induced by microglia in Alzheimer's disease mice. Neuroreport. 2022 May 18;33(8):327-335. doi: 10.1097/WNR.0000000000001783. Epub 2022 Apr 8. PMID: 35594435; PMCID: PMC9223515. 2. Xiong W, Yuan Z, Wang T, Wu S, Xiong Y, Yao Y, Yang Y, Wu H. Quercitrin Attenuates Acetaminophen-Induced Acute Liver Injury by Maintaining Mitochondrial Complex I Activity. Front Pharmacol. 2021 May 5;12:586010. doi: 10.3389/fphar.2021.586010. PMID: 34025394; PMCID: PMC8131832.

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1: Cincin ZB, Unlu M, Kiran B, Bireller ES, Baran Y, Cakmakoglu B. Apoptotic Effects of Quercitrin on DLD-1 Colon Cancer Cell Line. Pathol Oncol Res. 2015 Apr;21(2):333-8. doi: 10.1007/s12253-014-9825-3. Epub 2014 Aug 6. PubMed PMID: 25096395.

2: Córdoba A, Monjo M, Hierro-Oliva M, González-Martín ML, Ramis JM. Bioinspired Quercitrin Nanocoatings: A Fluorescence-Based Method for Their Surface Quantification, and Their Effect on Stem Cell Adhesion and Differentiation to the Osteoblastic Lineage. ACS Appl Mater Interfaces. 2015 Aug 5;7(30):16857-64. doi: 10.1021/acsami.5b05044. Epub 2015 Jul 24. PubMed PMID: 26167954.

3: Cincin ZB, Unlu M, Kiran B, Bireller ES, Baran Y, Cakmakoglu B. Molecular mechanisms of quercitrin-induced apoptosis in non-small cell lung cancer. Arch Med Res. 2014 Aug;45(6):445-54. doi: 10.1016/j.arcmed.2014.08.002. Epub 2014 Sep 2. PubMed PMID: 25193878.

4: Zhi K, Li M, Bai J, Wu Y, Zhou S, Zhang X, Qu L. Quercitrin treatment protects endothelial progenitor cells from oxidative damage via inducing autophagy through extracellular signal-regulated kinase. Angiogenesis. 2016 Jul;19(3):311-24. doi: 10.1007/s10456-016-9504-y. Epub 2016 Mar 26. PubMed PMID: 27017346.

5: Gómez-Florit M, Monjo M, Ramis JM. Identification of quercitrin as a potential therapeutic agent for periodontal applications. J Periodontol. 2014 Jul;85(7):966-74. doi: 10.1902/jop.2014.130438. Epub 2014 Feb 18. PubMed PMID: 24548116.

6: Gómez-Florit M, Monjo M, Ramis JM. Quercitrin for periodontal regeneration: effects on human gingival fibroblasts and mesenchymal stem cells. Sci Rep. 2015 Nov 12;5:16593. doi: 10.1038/srep16593. PubMed PMID: 26558438; PubMed Central PMCID: PMC4642307.

7: Ma JQ, Luo RZ, Jiang HX, Liu CM. Quercitrin offers protection against brain injury in mice by inhibiting oxidative stress and inflammation. Food Funct. 2016 Jan;7(1):549-56. doi: 10.1039/c5fo00913h. PubMed PMID: 26510118.

8: Li X, Jiang Q, Wang T, Liu J, Chen D. Comparison of the Antioxidant Effects of Quercitrin and Isoquercitrin: Understanding the Role of the 6″-OH Group. Molecules. 2016 Sep 19;21(9). pii: E1246. PubMed PMID: 27657022.

9: Li J, Liu QT, Chen Y, Liu J, Shi JL, Liu Y, Guo JY. Involvement of 5-HT1A Receptors in the Anxiolytic-Like Effects of Quercitrin and Evidence of the Involvement of the Monoaminergic System. Evid Based Complement Alternat Med. 2016;2016:6530364. doi: 10.1155/2016/6530364. Epub 2016 May 19. PubMed PMID: 27298626; PubMed Central PMCID: PMC4889836.

10: Truong VL, Ko SY, Jun M, Jeong WS. Quercitrin from Toona sinensis (Juss.) M.Roem. Attenuates Acetaminophen-Induced Acute Liver Toxicity in HepG2 Cells and Mice through Induction of Antioxidant Machinery and Inhibition of Inflammation. Nutrients. 2016 Jul 15;8(7). pii: E431. doi: 10.3390/nu8070431. PubMed PMID: 27428996; PubMed Central PMCID: PMC4963907.

11: Li W, Li H, Zhang M, Wang M, Zhong Y, Wu H, Yang Y, Morel L, Wei Q. Quercitrin ameliorates the development of systemic lupus erythematosus-like disease in a chronic graft-versus-host murine model. Am J Physiol Renal Physiol. 2016 Jul 1;311(1):F217-26. doi: 10.1152/ajprenal.00249.2015. Epub 2016 Feb 24. PubMed PMID: 26911849.

12: Verjee S, Brügger D, Abdel-Aziz H, Butterweck V. Permeation Characteristics of Hypericin across Caco-2 Monolayers in the Absence or Presence of Quercitrin - A Mass Balance Study. Planta Med. 2015 Aug;81(12-13):1111-20. doi: 10.1055/s-0035-1546034. Epub 2015 May 27. PubMed PMID: 26018919.

13: Dai X, Ding Y, Zhang Z, Cai X, Li Y. Quercetin and quercitrin protect against cytokine induced injuries in RINm5F β-cells via the mitochondrial pathway and NF-κB signaling. Int J Mol Med. 2013 Jan;31(1):265-71. doi: 10.3892/ijmm.2012.1177. Epub 2012 Nov 8. PubMed PMID: 23138875.

14: Satué M, Arriero Mdel M, Monjo M, Ramis JM. Quercitrin and taxifolin stimulate osteoblast differentiation in MC3T3-E1 cells and inhibit osteoclastogenesis in RAW 264.7 cells. Biochem Pharmacol. 2013 Nov 15;86(10):1476-86. doi: 10.1016/j.bcp.2013.09.009. Epub 2013 Sep 20. PubMed PMID: 24060614.

15: Hasan S, Singh K, Danisuddin M, Verma PK, Khan AU. Inhibition of major virulence pathways of Streptococcus mutans by quercitrin and deoxynojirimycin: a synergistic approach of infection control. PLoS One. 2014 Mar 12;9(3):e91736. doi: 10.1371/journal.pone.0091736. eCollection 2014. PubMed PMID: 24622055; PubMed Central PMCID: PMC3951425.

16: Yin Y, Li W, Son YO, Sun L, Lu J, Kim D, Wang X, Yao H, Wang L, Pratheeshkumar P, Hitron AJ, Luo J, Gao N, Shi X, Zhang Z. Quercitrin protects skin from UVB-induced oxidative damage. Toxicol Appl Pharmacol. 2013 Jun 1;269(2):89-99. doi: 10.1016/j.taap.2013.03.015. Epub 2013 Mar 29. PubMed PMID: 23545178; PubMed Central PMCID: PMC3700335.

17: Jiang S, Yang J, Qian D, Guo J, Shang EX, Duan JA, Xu J. Rapid screening and identification of metabolites of quercitrin produced by the human intestinal bacteria using ultra performance liquid chromatography/quadrupole-time-of-flight mass spectrometry. Arch Pharm Res. 2014 Feb;37(2):204-13. doi: 10.1007/s12272-013-0172-9. Epub 2013 Jun 11. PubMed PMID: 23754166.

18: Gomez-Florit M, Pacha-Olivenza MA, Fernández-Calderón MC, Córdoba A, González-Martín ML, Monjo M, Ramis JM. Quercitrin-nanocoated titanium surfaces favour gingival cells against oral bacteria. Sci Rep. 2016 Mar 1;6:22444. doi: 10.1038/srep22444. PubMed PMID: 26925553; PubMed Central PMCID: PMC4772538.

19: Liu B, Chen F, Bi C, Wang L, Zhong X, Cai H, Deng X, Niu X, Wang D. Quercitrin, an inhibitor of Sortase A, interferes with the adhesion of Staphylococcal aureus. Molecules. 2015 Apr 13;20(4):6533-43. doi: 10.3390/molecules20046533. PubMed PMID: 25871372.

20: Choi EM. Protective effect of quercitrin against hydrogen peroxide-induced dysfunction in osteoblastic MC3T3-E1 cells. Exp Toxicol Pathol. 2012 Mar;64(3):211-6. doi: 10.1016/j.etp.2010.08.008. Epub 2010 Sep 6. PubMed PMID: 20822887.