26791-73-1

26791-73-1 structure

Name: Xanthatin
Chemical 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
CAS Number: 26791-73-1
Molecular Formula: C₁₅H₁₈O₃
Molecular Weight: 246.302
Catalog: Natural product Moss
Create Date: 2018-09-27 22:36:43
Modify Date: 2024-01-03 01:31:10
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].

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
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)-

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	Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer Research Areas >> Infection Research Areas >> Inflammation/Immunology Signaling Pathways >> Metabolic Enzyme/Protease >> 5-Lipoxygenase Signaling Pathways >> Protein Tyrosine Kinase/RTK >> VEGFR Signaling Pathways >> Anti-infection >> Bacterial
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.

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℃

Hazard Codes	Xi