A quassinoid with diverse biological activities
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Ailanthone

Item No. 29194

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1β,11β,12α)-11,20-epoxy-1,11,12-trihydroxy-picrasa-3,13(21)-diene-2,16-dione
CAS Number
981-15-7
Synonyms
  • Δ13-Dehydrochaparrinone
Molecular Formula
C20H24O7
Formula Weight
376.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
λmax
238 nm
SMILES
C=C1[C@]([C@@]2([C@]3([H])[C@@](O)(OC2)[C@@H]1O)[C@@](O4)([H])C[C@@]([C@]3(C)[C@@H]5O)([H])C(C)=CC5=O)([H])CC4=O
InChi Code
InChI=1S/C20H24O7/c1-8-4-12(21)16(24)18(3)10(8)5-13-19-7-26-20(25,17(18)19)15(23)9(2)11(19)6-14(22)27-13/h4,10-11,13,15-17,23-25H,2,5-7H2,1,3H3/t10-,11-,13+,15+,16+,17+,18+,19+,20-/m0/s1
InChi Key
WBBVXGHSWZIJST-RLQYZCPESA-N
Origin
Plant/Ailanthus altissima
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $41

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    5 mg

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    10 mg

    $235

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    25 mg

    $534

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    Cayman Chemical
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    Product Description

    Ailanthone is a quassinoid that has been found in Ailanthus and has diverse biological activities.1,2,3 It is active against the P. falciparum strains HB-3 and Dd-2 in vitro (IC50s = 0.003 and 0.037 μg/ml, respectively).1 Ailanthone is phytotoxic, inhibiting radish seed germination by 88% when used at a concentration of 1 mM.2 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.3 Ailanthone (2 mg/kg) reduces tumor volume in 22Rv1, LNCaP, and VCaP castration-resistant prostate cancer (CRPC) mouse xenograft models.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Okunade, A.L., Bikoff, R.E., Casper, S.J., et al. Antiplasmodial activity of extracts and quassinoids isolated from seedlings of Ailanthus altissima (Simaroubaceae). Phytother. Res. 17(6), 675-677 (2003).

    2. De Feo, V., De Martino, L., Quaranta, E., et al. Isolation of phytotoxic compounds from tree-of-heaven (Ailanthus altissima swingle). J. Agric. Food Chem. 51(5), 1177-1180 (2003).

    3. He, Y., Peng, S., Wang, J., et al. Ailanthone targets p23 to overcome MDV3100 resistance in castration-resistant prostate cancer. Nat. Commun. 7:13122, (2016).