1,3,6,7-tetrahydroxyxanthone

Names

[ Name ]:
1,3,6,7-tetrahydroxyxanthone

[Synonym ]:
Norathyriol
magniferitin
1,3,6,7-Tetrahydroxyxanthen-9-one
1,3,6,7-Tetrahydroxyxantone
1,3,6,7-tetrahydroxyxanthone
2,4,6,7-Tetrahydroxyxanthone
1,3,6,7-Tetrahydroxy-9H-xanthen-9-one
9H-Xanthen-9-one, 1,3,6,7-tetrahydroxy-

Biological Activity

[Description]:

Norathyriol (Mangiferitin) is a natural metabolite of Mangifera. Norathyriol inhibits α-glucosidase in a noncompetitive manner with an IC50 of 3.12 μM[1]. Norathyriol inhibits PPARα, PPARβ, and PPARγ with IC50s of 92.8 µM, 102.4 µM, and 153.5 µM, respectively[2]. Antioxidant, anticancer, antimicrobial, anti-inflammatory, anti-bacterial activities.

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Cell Cycle/DNA Damage >> PPAR

Research Areas >> Inflammation/Immunology

[Target]

PPARα:92.8 μM (IC50)

PPARβ:102.4 μM (IC50)

PPARγ:153.5 μM (IC50)

[In Vitro]

Norathyriol (1-25 µM) inhibits growth by inducing cell cycle arrest in JB6 P+ cells. Norathyriol inhibits JB6 cell growth by inducing G2-M arrest[3]. Norathyriol suppresses UVB-induced phosphorylation of ERKs, AP-1 and NF-κB activation in JB6 P+ cells[3]Cell Growth Assay WB Cell Viability Assay[3] Cell Line: Mouse skin epidermal JB6 P+ cells Concentration: 0, 1, 10, or 25 µM Incubation Time: 24 or 72 hours Result: Inhibited cell growth in a dose- as well as time-dependent manner but does not cause cell death. Western Blot Analysis[3] Cell Line: JB6 P+ cells Concentration: 0, 1, 10, or 25 µM Incubation Time: 2 hours Result: Inhibited UVB-induced phosphorylation of ERKs and p90RSK.

[In Vivo]

Norathyriol is a natural metabolite of Mangifera in the human intestine with the oral availability and safety[1]. Norathyriol (0.92, 1.85 and 3.7 mg/kg) dose dependently decreased the serum urate levels by 27.0, 33.6 and 37.4%, respectively[4]. Animal Model: Adult Kunming mice weighing 18-22 g[4] Dosage: 0.92, 1.85 and 3.7 mg/kg Administration: Administered intragastrically; twice daily for five times Result: The serum uric acid levels were decreased by 27.0%, 33.6% and 37.4%.

[References]

[1]. Zhi-Long Shi, et al. In Vitro and In Vivo Effects of Norathyriol and Mangiferin on α-Glucosidase. Biochem Res Int. 2017;2017:1206015.

[2]. Ashley S Wilkinson,et al. Effects of the mango components mangiferin and quercetin and the putative mangiferin metabolite norathyriol on the transactivation of peroxisome proliferator-activated receptor isoforms. J Agric Food Chem. 2008 May 14;56(9):3037-42.

[3]. Jixia Li, et al. Norathyriol suppresses skin cancers induced by solar ultraviolet radiation by targeting ERK kinases. Cancer Res. 2012 Jan 1;72(1):260-70.

[4]. Yanfen Niu, et al. Hypouricaemic action of mangiferin results from metabolite norathyriol via inhibiting xanthine oxidase activity. Pharm Biol. 2016 Sep;54(9):1680-6.

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Boiling Point ]:
595.1±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₃H₈O₆

[ Molecular Weight ]:
260.20

[ Flash Point ]:
237.8±23.6 °C

[ Exact Mass ]:
260.032074

[ PSA ]:
111.13000

[ LogP ]:
0.95

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.801

Safety Information

[ Hazard Codes ]:
Xi

[ HS Code ]:
2932999099

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%