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. 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.

Product information

CAS Number: 26791-73-1

Molecular Weight: 246.30

Formula: C15H18O3

Chemical Name: (3aR, 7S, 8aS)-7-methyl-3-methylidene-6-[(1E)-3-oxobut-1-en-1-yl]-2H, 3H, 3aH, 4H, 7H, 8H, 8aH-cyclohepta[b]furan-2-one

Smiles: CC(=O)/C=C/C1=CC[C@H]2[C@H](C[C@@H]1C)OC(=O)C2=C

InChiKey: RBRPTFMVULVGIC-ZTIIIDENSA-N

InChi: InChI=1S/C15H18O3/c1-9-8-14-13(11(3)15(17)18-14)7-6-12(9)5-4-10(2)16/h4-6,9,13-14H,3,7-8H2,1-2H3/b5-4+/t9-,13+,14-/m0/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : 250 mg/mL (1015.02 mM; Need ultrasonic)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

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. Xanthatin (0-40 μM; 24 hours) has obscure inhibition effect on the proliferation of HUVEC in the absence of VEGF. 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. 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.

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.

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.

Products are for research use only. Not for human use.