Chinonin
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MedKoo CAT#: 584420

CAS#: 4773-96-0

Description: Chinonin, also known as Mangiferin, is the main active substance of the mango tree bark (Mangifera indica L.). The antinociceptive effects induced by mangiferin are mediated by the peripheral opioidergic system involving the activation of δ, κ, and probably µ, receptors, but not serotonergic receptors. This compound may prove to be effective in treating inflammatory pain in humans.

Chemical Structure

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Chinonin
CAS# 4773-96-0
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 584420
Name: Chinonin
CAS#: 4773-96-0
Chemical Formula: C19H18O11
Exact Mass: 422.08
Molecular Weight: 422.342
Elemental Analysis: C, 54.03; H, 4.30; O, 41.67

Price and Availability

Size Price Availability Quantity
10mg USD 257
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Synonym: Chinonin; Mangiferin; Alpizarin; Alpizarine; Aphloiol; Chinomin

IUPAC/Chemical Name: 9H-Xanthen-9-one, 2-beta-D-glucopyranosyl-1,3,6,7-tetrahydroxy- (9CI)

InChi Key: AEDDIBAIWPIIBD-ZJKJAXBQSA-N

InChi Code: InChI=1S/C19H18O11/c20-4-11-15(25)17(27)18(28)19(30-11)12-8(23)3-10-13(16(12)26)14(24)5-1-6(21)7(22)2-9(5)29-10/h1-3,11,15,17-23,25-28H,4H2/t11-,15-,17+,18-,19+/m1/s1

SMILES Code: O=C1C2=C(OC3=C1C=C(O)C(O)=C3)C=C(O)C([C@H]4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)O)=C2O

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

Shelf Life: >2 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: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
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Biological target: Mangiferin is a Nrf2 activator. Mangiferin suppresses nuclear translocation of the NF-κB subunits p65 and p50.
In vitro activity: Mangiferin showed inhibitory effects on A549, H1299, and H2030 cells, and the inhibition rate increased with increasing concentration. In addition, as the exposure time increased, the cell inhibition rate also showed an upward trend, which suggests that the inhibitory effect of mangiferin on LUAD cells is dose- and time-dependent (Figure 2). Reference: Evid Based Complement Alternat Med. 2021 Jul 12;2021:2822950. https://pubmed.ncbi.nlm.nih.gov/34335801/
In vivo activity: As shown in Figures 5(a) and 5(b), the IVD height was diminished after needle puncture, while mangiferin treatment largely attenuated this degeneration change of IVD, as assayed using X-ray measurements. As shown in Figures 5(c) and 5(d), MRI-T2WI detected a higher signal intensity in the rat IVD after mangiferin treatment than in the IVD of the needle puncture group, which proved that mangiferin plays an active role in the process of IVDD. Reference: Oxid Med Cell Longev. 2021; 2021: 6632786. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8216826/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 63.0 149.17
DMF 2.0 4.74

Preparing Stock Solutions

The following data is based on the product molecular weight 422.34 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. Chi XJ, Meng JJ, Lin CY, Su QS, Qin YY, Wei RH, Lan D, Huang C. Mangiferin Inhibits Human Lung Adenocarcinoma by Suppressing MiR-27b and MiR-92a. Evid Based Complement Alternat Med. 2021 Jul 12;2021:2822950. doi: 10.1155/2021/2822950. PMID: 34335801; PMCID: PMC8292060. 2. Qin ZZ, Ruan J, Lee MR, Sun K, Chen P, Chen Y, Hong M, Xia LH, Fang J, Tang H. Mangiferin Promotes Bregs Level, Activates Nrf2 Antioxidant Signaling, and Inhibits Proinflammatory Cytokine Expression in Murine Splenic Mononuclear Cells In Vitro. Curr Med Sci. 2021 Jun;41(3):454-464. doi: 10.1007/s11596-021-2371-9. Epub 2021 Jun 15. PMID: 34129203. 3. Yu H, Hou G, Cao J, Yin Y, Zhao Y, Cheng L. Mangiferin Alleviates Mitochondrial ROS in Nucleus Pulposus Cells and Protects against Intervertebral Disc Degeneration via Suppression of NF-κB Signaling Pathway. Oxid Med Cell Longev. 2021 Jun 11;2021:6632786. doi: 10.1155/2021/6632786. PMID: 34234886; PMCID: PMC8216826. 4. Zhang C, Yuan Y, Ou M. Mangiferin attenuates cigarette smoke-induced chronic obstructive pulmonary disease in male albino rats. Microvasc Res. 2021 Jun 15;138:104208. doi: 10.1016/j.mvr.2021.104208. Epub ahead of print. PMID: 34139206.
In vitro protocol: 1. Chi XJ, Meng JJ, Lin CY, Su QS, Qin YY, Wei RH, Lan D, Huang C. Mangiferin Inhibits Human Lung Adenocarcinoma by Suppressing MiR-27b and MiR-92a. Evid Based Complement Alternat Med. 2021 Jul 12;2021:2822950. doi: 10.1155/2021/2822950. PMID: 34335801; PMCID: PMC8292060. 2. Qin ZZ, Ruan J, Lee MR, Sun K, Chen P, Chen Y, Hong M, Xia LH, Fang J, Tang H. Mangiferin Promotes Bregs Level, Activates Nrf2 Antioxidant Signaling, and Inhibits Proinflammatory Cytokine Expression in Murine Splenic Mononuclear Cells In Vitro. Curr Med Sci. 2021 Jun;41(3):454-464. doi: 10.1007/s11596-021-2371-9. Epub 2021 Jun 15. PMID: 34129203.
In vivo protocol: 1. Yu H, Hou G, Cao J, Yin Y, Zhao Y, Cheng L. Mangiferin Alleviates Mitochondrial ROS in Nucleus Pulposus Cells and Protects against Intervertebral Disc Degeneration via Suppression of NF-κB Signaling Pathway. Oxid Med Cell Longev. 2021 Jun 11;2021:6632786. doi: 10.1155/2021/6632786. PMID: 34234886; PMCID: PMC8216826. 2. Zhang C, Yuan Y, Ou M. Mangiferin attenuates cigarette smoke-induced chronic obstructive pulmonary disease in male albino rats. Microvasc Res. 2021 Jun 15;138:104208. doi: 10.1016/j.mvr.2021.104208. Epub ahead of print. PMID: 34139206.

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1: Zajac D, Stasinska A, Delgado R, Pokorski M. Mangiferin and its traversal into the brain. Adv Exp Med Biol. 2013;756:105-11. doi: 10.1007/978-94-007-4549-0_14. PubMed PMID: 22836625.

2: Na L, Zhang Q, Jiang S, Du S, Zhang W, Li Y, Sun C, Niu Y. Mangiferin supplementation improves serum lipid profiles in overweight patients with hyperlipidemia: a double-blind randomized controlled trial. Sci Rep. 2015 May 19;5:10344. doi: 10.1038/srep10344. PubMed PMID: 25989216; PubMed Central PMCID: PMC4437311.

3: Kawakami CM, Gaspar LR. Mangiferin and naringenin affect the photostability and phototoxicity of sunscreens containing avobenzone. J Photochem Photobiol B. 2015 Oct;151:239-47. doi: 10.1016/j.jphotobiol.2015.08.014. Epub 2015 Aug 15. PubMed PMID: 26318281.

4: Andreu GL, Maurmann N, Reolon GK, de Farias CB, Delgado R, Roesler R. Effect of mangiferin, a naturally occurring glucoxylxanthone, on fear memory in rats. Arzneimittelforschung. 2011;61(7):382-5. PubMed PMID: 21899205.

5: Wang HL, Li CY, Zhang B, Liu YD, Lu BM, Shi Z, An N, Zhao LK, Zhang JJ, Bao JK, Wang Y. Mangiferin facilitates islet regeneration and β-cell proliferation through upregulation of cell cycle and β-cell regeneration regulators. Int J Mol Sci. 2014 May 20;15(5):9016-35. doi: 10.3390/ijms15059016. PubMed PMID: 24853132; PubMed Central PMCID: PMC4057772.

6: Sellamuthu PS, Arulselvan P, Fakurazi S, Kandasamy M. Beneficial effects of mangiferin isolated from Salacia chinensis on biochemical and hematological parameters in rats with streptozotocin-induced diabetes. Pak J Pharm Sci. 2014 Jan;27(1):161-7. PubMed PMID: 24374436.

7: Jangra A, Lukhi MM, Sulakhiya K, Baruah CC, Lahkar M. Protective effect of mangiferin against lipopolysaccharide-induced depressive and anxiety-like behaviour in mice. Eur J Pharmacol. 2014 Oct 5;740:337-45. doi: 10.1016/j.ejphar.2014.07.031. Epub 2014 Jul 23. PubMed PMID: 25064341.

8: Zhang B, Zhao J, Li S, Zeng L, Chen Y, Fang J. Mangiferin activates the Nrf2-ARE pathway and reduces etoposide-induced DNA damage in human umbilical cord mononuclear blood cells. Pharm Biol. 2015 Apr;53(4):503-11. doi: 10.3109/13880209.2014.927890. Epub 2014 Nov 7. PubMed PMID: 25380307.

9: Cai F, Sun L, Gao S, Zhan Q, Wang W, Chen W. An improved LC-MS/MS method for the determination of mangiferin in rat plasma and its application in nonlinear pharmacokinetics. Pharmazie. 2014 Mar;69(3):168-72. PubMed PMID: 24716404.

10: Sampaio Cde G, Frota LS, Magalhães HS, Dutra LM, Queiroz DC, Araújo RS, Becker H, de Souza JR, Ricardo NM, Trevisan MT. Chitosan/mangiferin particles for Cr(VI) reduction and removal. Int J Biol Macromol. 2015 Jul;78:273-9. doi: 10.1016/j.ijbiomac.2015.03.038. Epub 2015 Apr 1. PubMed PMID: 25841368.

11: Zhang X, Su B, Li J, Li Y, Lu D, Zhu K, Pei H, Zhao M. Analysis by RP-HPLC of mangiferin component correlation between medicinal loranthus and their mango host trees. J Chromatogr Sci. 2014 Jan;52(1):1-4. doi: 10.1093/chromsci/bms196. Epub 2012 Dec 17. PubMed PMID: 23247031.

12: Fan S, Gu Y, Li G, Zhang M, Li B, Zhang H, Hou Y. [Determination of mangiferin in rat plasma and aqueous humor by HPLC]. Zhongguo Zhong Yao Za Zhi. 2011 Mar;36(5):598-602. Chinese. PubMed PMID: 21657080.

13: Xing X, Li D, Chen D, Zhou L, Chonan R, Yamahara J, Wang J, Li Y. Mangiferin treatment inhibits hepatic expression of acyl-coenzyme A:diacylglycerol acyltransferase-2 in fructose-fed spontaneously hypertensive rats: a link to amelioration of fatty liver. Toxicol Appl Pharmacol. 2014 Oct 15;280(2):207-15. doi: 10.1016/j.taap.2014.08.001. Epub 2014 Aug 11. PubMed PMID: 25123789.

14: Liu H, Wu B, Pan G, He L, Li Z, Fan M, Jian L, Chen M, Wang K, Huang C. Metabolism and pharmacokinetics of mangiferin in conventional rats, pseudo-germ-free rats, and streptozotocin-induced diabetic rats. Drug Metab Dispos. 2012 Nov;40(11):2109-18. doi: 10.1124/dmd.112.045849. Epub 2012 Aug 2. PubMed PMID: 22859782.

15: Zhang BP, Zhao J, Li SS, Yang LJ, Zeng LL, Chen Y, Fang J. Mangiferin activates Nrf2-antioxidant response element signaling without reducing the sensitivity to etoposide of human myeloid leukemia cells in vitro. Acta Pharmacol Sin. 2014 Feb;35(2):257-66. doi: 10.1038/aps.2013.165. Epub 2013 Dec 30. PubMed PMID: 24374812; PubMed Central PMCID: PMC4651226.

16: Huh JE, Koh PS, Seo BK, Park YC, Baek YH, Lee JD, Park DS. Mangiferin reduces the inhibition of chondrogenic differentiation by IL-1β in mesenchymal stem cells from subchondral bone and targets multiple aspects of the Smad and SOX9 pathways. Int J Mol Sci. 2014 Sep 11;15(9):16025-42. doi: 10.3390/ijms150916025. PubMed PMID: 25216336; PubMed Central PMCID: PMC4200868.

17: Hou S, Wang F, Li Y, Li Y, Wang M, Sun D, Sun C. Pharmacokinetic study of mangiferin in human plasma after oral administration. Food Chem. 2012 May 1;132(1):289-94. doi: 10.1016/j.foodchem.2011.10.079. Epub 2011 Nov 2. PubMed PMID: 26434292.

18: Louisa M, Soediro TM, Suyatna FD. In vitro modulation of P-glycoprotein, MRP-1 and BCRP expression by mangiferin in doxorubicin-treated MCF-7 cells. Asian Pac J Cancer Prev. 2014;15(4):1639-42. PubMed PMID: 24641381.

19: Liu YW, Zhu X, Yang QQ, Lu Q, Wang JY, Li HP, Wei YQ, Yin JL, Yin XX. Suppression of methylglyoxal hyperactivity by mangiferin can prevent diabetes-associated cognitive decline in rats. Psychopharmacology (Berl). 2013 Aug;228(4):585-94. doi: 10.1007/s00213-013-3061-5. Epub 2013 Mar 26. PubMed PMID: 23529380.

20: Izquierdo T, Espinosa de los Monteros-Zuñiga A, Cervantes-Durán C, Lozada MC, Godínez-Chaparro B. Mechanisms underlying the antinociceptive effect of mangiferin in the formalin test. Eur J Pharmacol. 2013 Oct 15;718(1-3):393-400. doi: 10.1016/j.ejphar.2013.08.004. Epub 2013 Aug 23. PubMed PMID: 23973647.