| Identification | Back Directory | [Name]
ailanthone | [CAS]
981-15-7 | [Synonyms]
ailanthone
Δ13-Dehydrochaparrinone
13,21-Didehydrochaparrinone
11β,20-Epoxy-1β,11,12α-trihydroxypicrasa-3,13(21)-diene-2,16-dione
(1β,11β,12α)-11,20-Epoxy-1,11,12-trihydroxypicrasa-3,13(21)-diene-2,16-dione
Picrasa-3,13(21)-diene-2,16-dione,11,20-epoxy-1,11,12-trihydroxy-, (1b,11b,12a)-
Picrasa-3,13(21)-diene-2,16-dione, 11,20-epoxy-1,11,12-trihydroxy-, (1β,11β,12α)- | [Molecular Formula]
C20H24O7 | [MDL Number]
MFCD01729487 | [MOL File]
981-15-7.mol | [Molecular Weight]
376.403 |
| Questions And Answer | Back Directory | [Preparation]
Take fresh bark or root bark of Ailanthus altissima, soak it in 5-10 times its weight of alkaline water with pH=9-13 for 24-72 hours, filter, adjust the pH of the filtrate to neutral with acid, concentrate, and pass the concentrate through a macroporous adsorption resin column for adsorption. Wash with water to remove impurities, elute with 60-85% ethanol, collect 3-8 times the column volume of eluent, recover the ethanol under reduced pressure, refrigerate for 12-36 hours to crystallize, filter, take the filter residue, add acetone to recrystallize, wash and dry to obtain ailanthone. |
| Chemical Properties | Back Directory | [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) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS06 | [Signal word ]
Danger | [Hazard statements ]
H300 | [Precautionary statements ]
P301+P330+P331+P310 | [WGK Germany ]
WGK 3 | [Storage Class]
6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials | [Hazard Classifications]
Acute Tox. 2 Oral |
| Hazard Information | Back Directory | [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. | [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]
Not only i.p. administration but also p.o. administration of Ailanthone has excellent efficiency for blocking the growth of CRPC xenografts. In pharmacokinetic studies, Ailanthone exhibits good solubility in water and good bioavailability (>20%). In addition, Ailanthone effectively suppresses CRPC tumour growth, despite not reaching a steady state of plasma drug concentration during the course of treatment[1]. | [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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