Xanthatin

Modify Date: 2024-01-03 01:31:10

Xanthatin Structure
Xanthatin structure
Common Name Xanthatin
CAS Number 26791-73-1 Molecular Weight 246.302
Density 1.1±0.1 g/cm3 Boiling Point 444.3±45.0 °C at 760 mmHg
Molecular Formula C15H18O3 Melting Point 114.5-115°
MSDS N/A Flash Point 199.1±28.8 °C

 Use of Xanthatin


Xanthatin is isolated from Xanthium strumarium leaves. Xanthatin exhibits strong antitumor activities against a variety of cancer cells through apoptosis persuasion and shows anti-inflammatory activities by inhibiting PGE2 synthesis and 5-lipoxygenase activity[1]. Xanthatin is a potent and orally active inhibitor of VEGFR2 kinase activity with an IC50 of 3.8 μM and prominently blocks the phosphorylation of VEGFR2 at Tyr951 site. Xanthatin inhibits angiogenesis and has the potential for the investigation of breast cancer[2].

 Names

Name (3aR,7S,8aS)-7-methyl-3-methylidene-6-[(E)-3-oxobut-1-enyl]-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one
Synonym More Synonyms

 Xanthatin Biological Activity

Description Xanthatin is isolated from Xanthium strumarium leaves. Xanthatin exhibits strong antitumor activities against a variety of cancer cells through apoptosis persuasion and shows anti-inflammatory activities by inhibiting PGE2 synthesis and 5-lipoxygenase activity[1]. Xanthatin is a potent and orally active inhibitor of VEGFR2 kinase activity with an IC50 of 3.8 μM and prominently blocks the phosphorylation of VEGFR2 at Tyr951 site. Xanthatin inhibits angiogenesis and has the potential for the investigation of breast cancer[2].
Related Catalog
Target

IC50: apoptosis; 3.8 μM (VEGFR2 kinase); 2.63 µg/mL (T. b. brucei)[1]

In Vitro Xanthatin is against T. b. brucei with an IC50 value of 2.63 µg/mL and exhibits weak irreversible inhibition of parasite specific trypanothione reductase[1]. Xanthatin (0-40 μM; 24 hours) has obscure inhibition effect on the proliferation of HUVEC in the absence of VEGF[2]. Xanthatin (5-40 μM; 24 hours) inhibits breast cancer cell proliferation in a dose responsive manner. Xanthatin inhibits HCC1937, MDA-MB-415, SK-BR-3, MCF-7 and MDA-MB-231 with IC50 values of 81 μM, 31 μM, 38 μM, 30 μM, and 17 μM, respectively[2]. Xanthatin (0-10 μM; 24 hours) dose dependently suppresses the phosphorylation of STAT3 (Ser727), at the same time, it also results in a rapid dephosphorylation of down-stream kinases of STAT3, including PI3K and Akt, including PI3K (p-PI3K p85 tyr458) and Akt[2]. Cell Proliferation Assay[2] Cell Line: HUVEC cells Concentration: 0 μM, 5 μM, 10 μM, 15 μM, 20 μM, 30 μM, 40 μM Incubation Time: 24 hours Result: Inhibited cell growth from dose 10 μM in the presence of vEGF. Cell Viability Assay[2] Cell Line: HCC1937, MDA-MB-415, SK-BR-3, MCF-7 and MDA-MB-231 cells Concentration: 5, 10, 15, 20, 30, and 40 μM Incubation Time: 24 hours Result: Inhibited breast cancer cell growth. Western Blot Analysis[2] Cell Line: HUVEC cells Concentration: 0, 3, and 10 μM Incubation Time: 24 hours Result: Inhibited VEGFR2 downstream signaling pathways and blocked VEGF-induced STAT3 activation in HUVEC.
In Vivo Xanthatin (intragastric administration; 20 mg/kg; once daily; 25 days) leads to significant inhibition of tumor volume. And this compound is well-tolerated and exhibits no significant difference in weight compares to the vehicle group[2]. Animal Model: Transplanted MDA-MB-231 cells into mice and constucted human breast cancer xenograft mouse model[2]  Dosage: 20 mg/kg; once daily; 25 days Administration: Intragastric administration Result: Supressed tumor growth and tumor angiogenesis in vivo.
References

[1]. Nibret E, et al. Biological activities of xanthatin from Xanthium strumarium leaves.Phytother Res. 2011 Dec;25(12):1883-90.

[2]. Yu Y, et al. Xanthatin, a novel potent inhibitor of VEGFR2 signaling, inhibits angiogenesis and tumor growth in breast cancer cells.Int J Clin Exp Pathol. 2015 Sep 1;8(9):10355-64.

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 444.3±45.0 °C at 760 mmHg
Melting Point 114.5-115°
Molecular Formula C15H18O3
Molecular Weight 246.302
Flash Point 199.1±28.8 °C
Exact Mass 246.125595
PSA 43.37000
LogP 1.58
Vapour Pressure 0.0±1.1 mmHg at 25°C
Index of Refraction 1.528
Storage condition 2-8℃

 Safety Information

Hazard Codes Xi

 Synonyms

(3aR,7S,8aS)-7-Methyl-3-methylene-6-[(1Z)-3-oxo-1-buten-1-yl]-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one
(3aR,7S,8aS)-7-Methyl-3-methylene-6-[(1Z)-3-oxobut-1-en-1-yl]-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one
[3aR-(3aa,7b,8ab)]-3,3a,4,7,8,8a-Hexahydro-7-methyl-3-methylene-6-(3-oxo-1-butenyl)-2H-cyclohepta[b]furan-2-one
(3aR,7S,8aS)-7-methyl-3-methylidene-6-[(1Z)-3-oxobut-1-en-1-yl]-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one
8-epi-Xanthatin
Xanthatin
2H-Cyclohepta[b]furan-2-one, 3,3a,4,7,8,8a-hexahydro-7-methyl-3-methylene-6-[(1Z)-3-oxo-1-buten-1-yl]-, (3aR,7S,8aS)-
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