ailanthone Chemical Properties

Melting point:

235-237 °C

Boiling point:

641.0±55.0 °C(Predicted)

Density 

1.47

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

DMSO:100.0(Max Conc. mg/mL);265.67(Max Conc. mM)

form 

A crystalline solid

pka

11.85±0.70(Predicted)

color 

White to off-white

InChIKey

WBBVXGHSWZIJST-BIKIFPNSNA-N

SMILES

[C@]123CO[C@@]4(O)[C@H](O)C(=C)C1CC(=O)O[C@]2([H])C[C@@]1([H])C(C)=CC(=O)[C@@H](O)[C@]1(C)[C@]34[H] |&1:0,3,5,14,17,24,26,28,r|

LogP

-0.760 (est)

ailanthone Usage And Synthesis

Description

Ailanthone is a quassinoid that has been found in Ailanthus and has diverse biological activities. It is active against the P. falciparum strains HB-3 and Dd-2 in vitro (IC₅₀s = 0.003 and 0.037 μg/ml, respectively). Ailanthone is phytotoxic, inhibiting radish seed germination by 88% when used at a concentration of 1 mM. It inhibits dihydrotestosterone-induced androgen receptor transcriptional activity (IC₅₀ = 69 nM in a reporter assay), as well as the growth and colony formation of LNCaP and 22RV1 androgen receptor-expressing cells, but not androgen receptor-negative PC3 and DU145 cells, when used at a concentration of 0.1 μM. Ailanthone (2 mg/kg) reduces tumor volume in 22Rv1, LNCaP, and VCaP castration-resistant prostate cancer (CRPC) mouse xenograft models.

Uses

Ailanthone has potent antineoplastic activity against anti-hepatocellular carcinoma (HCC) and has been shown to inhibit Huh7 cancer cell growth through cell cycle arrest and apoptosis in vitro and in vivo.

Definition

ChEBI: Ailanthone is a triterpenoid.

in vivo

References

[1] ADEWOLE L OKUNADE. Antiplasmodial activity of extracts and quassinoids isolated from seedlings of Ailanthus altissima (Simaroubaceae).[J]. Phytotherapy Research, 2003, 17 6: 675-677. DOI: 10.1002/ptr.1336
[2] VINCENZO DE FEO. Isolation of Phytotoxic Compounds from Tree-of-Heaven (Ailanthus altissima Swingle)[J]. Journal of Agricultural and Food Chemistry, 2003, 51 5: 1177-1180. DOI: 10.1021/jf020686+
[3] YUNDONG HE. Ailanthone targets p23 to overcome MDV3100 resistance in castration-resistant prostate cancer[J]. Nature Communications, 2016, 7 1. DOI: 10.1038/ncomms13122

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