Isoalantolactone

Isoalantolactone, one of the major sesquiterpene lactone compounds, is isolated from the roots of Anula helenium and possesses multiple biological activities including antifungal, anthelmintic, antimicrobial, anti-inflammatory, antitrypanosomal activities and antiproliferative effects on several cancer cell lines, such as colon, melanoma, ovary, prostate, lung, and leukemia. Isoalantolactone is an apoptosis inducer, which also acts as an alkylating agent.

Product information

CAS Number: 470-17-7

Molecular Weight: 232.32

Formula: C15H20O2

Synonym:

(+)-Isoalantolactone; Isohelenin

Chemical Name: 8a-methyl-3,5-dimethylidene-dodecahydronaphtho[2,3-b]furan-2-one

Smiles: C[C@@]12C[C@H]3OC(=O)C(=C)[C@H]3C[C@H]1C(=C)CCC2

InChiKey: CVUANYCQTOGILD-QVHKTLOISA-N

InChi: InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h11-13H,1-2,4-8H2,3H3/t11-,12+,13-,15-/m1/s1

Technical Data

Appearance: Solid Power

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

Solubility: DMSO : 50 mg/mL (215.22 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: ≥12 months 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:

Isoalantolactone inhibits growth and induces apoptosis in pancreatic cancer cells. Isoalantolactone increases the expression of phosphorylated p38 MAPK, Bax, and cleaved caspase-3 and decreases the expression of Bcl-2 in a dose-dependent manner. Isoalantolactone treatment in HeLa cancer cells exhibits cytotoxicity in a dose-dependent manner with a low IC50 value of 8.15 ± 1.16 μM.

In Vivo:

Isoalantolactone does not induce any acute or chronic toxicity in liver and kidneys of CD1 mice at dose of 100 mg/kg body weight. Isoalantolactone is distributed and eliminated rapidly possibly due to its low-polarity characteristic. A large apparent volume of distribution (138.44 ± 54.14 L) suggests that the lactones may accumulate in certain organs with high concentration after intravenous injection.

References:

1. Lawrence NJ, et al. Cytotoxic Michael-type amine adducts of alpha-methylene lactones alantolactone and isoalantolactone. Bioorg Med Chem Lett. 2001 Feb 12;11(3):429-31.
2. Khan M, et al. Isoalantolactone induces reactive oxygen species mediated apoptosis in pancreatic carcinoma PANC-1 cells. Int J Biol Sci. 2012;8(4):533-47.

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