Gnetol

Names

[ Name ]:
Gnetol

[Synonym ]:
2-[(E)-2-(3,5-Dihydroxyphenyl)vinyl]-1,3-benzenediol
Thieno[3,4-b]-1,4,7-trioxonin,2,3,5,6-tetrahydro
2,3',5',6-tetrahydroxy-trans-stilbene
1,3-Benzenediol, 2-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-
2,3,5,6-tetrahydrothieno[3,4-b][1,4,7]trioxonin

Biological Activity

[Description]:

Gnetol is a phenolic compound isolated from the root of Gnetum ula Brongn. Gnetol potently inhibits COX-1 (IC50 of 0.78 μM) and HDAC. Gnetol is a potent tyrosinase inhibitor with an IC50 of 4.5 μM for murine tyrosinase and suppresses melanin biosynthesis. Gnetol has antioxidant, antiproliferative, anticancer and hepatoprotective activity. Gnetol also possesses concentration-dependent α-Amylase, α-glucosidase, and adipogenesis activities[1][2][3].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Immunology/Inflammation >> COX

Signaling Pathways >> Metabolic Enzyme/Protease >> Tyrosinase

Research Areas >> Metabolic Disease

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

Signaling Pathways >> Epigenetics >> HDAC

[Target]

COX-1:0.78 μM (IC50)

Tyrosinase:4.5 μM (IC50)

HDAC

[In Vitro]

The antiproliferative activities of Gnetol are tested in HCT-116, Hep-G2, MDA-MB-231, and PC-3 cell lines by measuring cell viability after treatment with 4.1 μM, 40.9 μM, 204.7 μM, 409.4 μM, and 1023.6 μM. Gnetol shows concentration-dependent reductions in cell viability in cancer cell lines with greatest activity in colorectal cancer[1]. Gnetol at 200 µg/mL significantly offers the highest protection of 54.3% against the toxicant. A lower dose of Gnetol (50 µg/mL) also shields the cell line from the toxic effects of CCl4[3]. The ligand molecule TGF-β and PPARα protein show that Gnetol has the binding affinity of 7.0 and 8.4, respectively[3].

[In Vivo]

Male Sprague-Dawley rats were cannulated and dosed either intravenously with Gnetol (10 μg/kg) or orally (100 mg/kg). After oral and intravenous administration, Gnetol is detected in both serum and urine as the parent compound and as a glucuronidated metabolite. The bioavailability of Gnetol is determined to be 6%. Gnetol is rapidly glucuronidated and is excreted in urine and via nonrenal routes[1]. Pretreatment of Male NIH Swiss mice (20-35 g) with Gnetol (50mg/kg, SC) is able to increase the latency period to response in analgesia models[1].

[References]

[1]. Remsberg CM, et al. Preclinical Pharmacokinetics and Pharmacodynamics and Content Analysis of Gnetol in Foodstuffs. Phytother Res. 2015 Aug;29(8):1168-79.

[2]. Ohguchi K, et al. Gnetol as a potent tyrosinase inhibitor from genus Gnetum. Biosci Biotechnol Biochem. 2003 Mar;67(3):663-5.

[3]. Jinadatta P, et al. In silico, in vitro: antioxidant and antihepatotoxic activity of gnetol from Gnetum ula Brongn. Bioimpacts. 2019;9(4):239-249.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
540.8±30.0 °C at 760 mmHg

[ Melting Point ]:
87 - 90ºC

[ Molecular Formula ]:
C₁₄H₁₂O₄

[ Molecular Weight ]:
244.243

[ Flash Point ]:
269.7±19.2 °C

[ Exact Mass ]:
244.073563

[ PSA ]:
80.92000

[ LogP ]:
3.73

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.801

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
Xn

[ HS Code ]:
2907299090

Customs

[ HS Code ]: 2907299090

[ Summary ]:
2907299090 polyphenols; phenol-alcohols。supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward)。VAT:17.0%。tax rebate rate:9.0%。MFN tariff:5.5%。general tariff:30.0%