Ailanthone

Herbicidal effects under field conditions of Ailanthus altissima bark extract, which contains ailanthone.[Reference: WebLink]

Plant & Soil, 2003, 256(1):85-99.

METHODS AND RESULTS:
These application rates provided herbicidal activity equivalent to 4.5, 2.2, 1.1, 0.6, 0.3, and 0.0 kg of pure Ailanthone per hectare, based on the results of a laboratory bioassay of extract and pure Ailanthone. Strong herbicidal effects were observed within several days. Even the lowest rate caused mortality and injury in excess of 50% for nine of the 17 species, and a significant reduction in shoot biomass for 13 species. The second field trial tested the ability of bark extract to control weeds under field conditions with horticultural crops (bush bean, cauliflower, sweet corn, tomato). A. altissima bark extract was sprayed post-emergence at rates of 99, 50, 26, 13, and 0 kg ha–1, providing herbicidal activity equivalent to 1.1, 0.6, 0.3, 0.14, and 0.0 kg of pure Ailanthone per hectare. Extract treatment provided partial weed control (greatest reduction in weed biomass was 40%), but also caused serious crop injury. Bush bean was the only crop that showed a significant increase in shoot biomass and fruit yield, compared to the non-weeded control.
CONCLUSIONS:
None of the crops, regardless of application rate, showed a level of shoot biomass or fruit yield comparable to the hand-weeded control. The herbicidal effects of A. altissima bark extract declined within the first few weeks after application, supporting previous evidence that Ailanthone is rapidly degraded under field conditions.

Antitumor activity of novel ailanthone derivatives in vitro and in vivo.[Pubmed: 3178149]

Anticancer Res. 1988 Jul-Aug;8(4):573-9.

The antitumor activities of two Ailanthone derivatives with 15 beta-acyloxy side chains were investigated.
METHODS AND RESULTS:
The cytotoxic activity of 11 beta, 20-epoxy-1 beta, 11 alpha, 12 alpha-trihydroxy-15-beta-[E)-3-methyl-2-octenoyl) oxypicras-3,13(21)-diene-2,16-dione (SUN2071) and 11 beta, 20-epoxy-1 beta, 11 alpha, 12 alpha-trihydroxy-15 beta-[E)-2-undecenoyl) oxypicras-3,13(21)-diene-2,16-dione (SUN0237) was close to that of bruceantin and vincristine. SUN2071 was shown to be a potent inhibitor of protein synthesis in L1210 cultured cells. When administered i.p. to i.p. inoculated P388 leukemia mice, daily treatment with SUN2071 and SUN0237 significantly increased the lifespan (increases in lifespan in excess of 100% were achieved). These increases were comparable to those achieved with vincristine. The therapeutic ratio of SUN2071 was also close to that of vincristine. However, the compounds were ineffective when administered as a single injection. Daily i.p. treatment with SUN2071 demonstrated significant tumor growth inhibition in mice inoculated s.c. with colon-38 and moderate activity against i.p. L1210 leukemia and i.p. B16 melanoma. The compounds were ineffective when tested against the Lewis lung carcinoma and colon-26.
CONCLUSIONS:
In a preliminary toxicological study, SUN2071 at a therapeutic dose in daily consecutive i.p. injection produced leucopenia.

Antiamebic properties of some derivatives of ailantone and quassin.[Pubmed: 7227501]

Farmaco Sci. 1981 Feb;36(2):116-22.

Owing to its high toxicity, Ailanthone, one of the most potent in vivo amoebicidal drugs of natural origin, cannot be safely employed in clinical trials. With the aim of obtaining a compound with a better therapeutic index and of studying possible relationships between biological activity and chemical structure, many derivatives of Ailanthone and of the chemically related, although biologically inactive, quassin have been prepared and tested.

Ailanthone Inhibits Huh7 Cancer Cell Growth via Cell Cycle Arrest and Apoptosis In Vitro and In Vivo.[Pubmed: 26525771]

Sci Rep. 2015; 5: 16185.

While searching for natural anti-hepatocellular carcinoma (HCC) components in Ailanthus altissima, we discovered that Ailanthone had potent antineoplastic activity against HCC. However, the molecular mechanisms underlying the antitumor effect of Ailanthone on HCC have not been examined. In this study, the antitumor activity and the underlying mechanisms of Ailanthone were evaluated in vitro and in vivo.
METHODS AND RESULTS:
Mechanistic studies showed that Ailanthone induced G0/G1-phase cell cycle arrest, as indicated by decreased expression of cyclins and CDKs and increased expression of p21 and p27. Our results demonstrated that Ailanthone triggered DNA damage characterized by activation of the ATM/ATR pathway. Moreover, Ailanthone-induced cell death was associated with apoptosis, as evidenced by an increased ratio of cells in the subG1 phase and by PARP cleavage and caspase activation. Ailanthone-induced apoptosis was mitochondrion-mediated and involved the PI3K/AKT signaling pathway in Huh7 cells. In vivo studies demonstrated that Ailanthone inhibited the growth and angiogenesis of tumor xenografts without significant secondary adverse effects, indicating its safety for treating HCC.
CONCLUSIONS:
In conclusion, our study is the first to report the efficacy of Ailanthone against Huh7 cells and to elucidate its underlying molecular mechanisms. These findings suggest that Ailanthone is a potential agent for the treatment of liver cancer.

Nat Prod Commun. 2011 May;6(5):593-6.

Herbicide activity of extracts from Ailanthus altissima (Simaroubaceae).[Pubmed: 21615014]

The purpose of the present study was to isolate and characterize Ailanthone-rich materials from the bark of the deciduous tree Ailanthus altissima (Mill.) Swingle and to assess their herbicide activity on selected herbaceous species.
METHODS AND RESULTS:
Ailanthone-rich fractions were obtained from A. altissima bark by extraction with dichloromethane and ethyl acetate and subsequent purification of these crude extracts, and of the remaining water mixture after solvent extraction, by means of gel permeation chromatography. A number of fractions were isolated and characterized for Ailanthone content. A dichloromethane fraction was shown to contain 92% w/w of Ailanthone, as demonstrated by HPLC and NMR analysis. A significant pre-emergence herbicide activity was found for most of the extracts which was directly correlated to Ailanthone concentration. A remarkable combined pre- and post-emergence herbicide activity was found for a specific fraction.
CONCLUSIONS:
These results indicate that the bark of A. altissima may represent an interesting source for the production of natural herbicides for use in agriculture.