Ailanthus

 Simaroubaceae

Tree-of-Heaven

The World Botanical Associates Web Page
Prepared by Richard W. Spjut
August 2006

Ailanthus altissima
Kern River, Bakersfield, CA
May 2006

 
   

Trees and Shrubs of Kern County (Jan 2013)

 

Anderson L.A., A. Harris and J. D. Phillipson.  1983. Production of cytotoxic canthin-6-one alkaloids by Ailanthus altissima plant cell cultures.  J. Nat. Prod. 46(3): 374378. Ailanthus altissima (Mill.) Swingle was established as callus- and cell-suspension cultures. Canthin-6-one and 1-methoxycanthin-6-one were isolated by a combination of preparative tlc and preparative hplc. The two alkaloids were identified by their uv, ms, and 1H-nmr spectra. The combined yield of the two alkaloids was 1.38% of dry weight from callus and 1.27% of dry weight from cell suspensions. The cytotoxicities of canthin-6-one, 1-methoxycanthin-6-one, 5-methoxycanthin-6-one, and canthin-6-one-3-N-oxide to guinea pig ear keratinocytes have been compared, and the IC50 values range from 1.11 to 5.76 micrograms/ml. There is no significant difference in activity among these four cytotoxic alkaloids.

Kubota K, N. Fukamiya, H. Tokuda, H. Nishino, K. Tagahara, K. H. Lee and M. Okano. 1997. Quassinoids as inhibitors of Epstein-Barr virus early antigen activation. Cancer Lett. 113 (1-2): 165168. Short-term in vitro assays for tumor promoters and antitumor promoters (Epstein-Barr virus activation test) were carried out for 14 quassinoids isolated from Ailanthus altissima. Some quassinoids, including ailantinol B, ailantinol C, ailanthone, and shinjulactone A, showed moderate activity at a molar ratio of 1:100 (TPA/quassinoids), and the results led to the elucidation of structure-activity relationships.

Ogura M, G. A. Cordell, A. D. Kinghorn and N. R. Farnsworth. 1977. Potential anticancer agents vi. Constituents of Ailanthus excelsa (Simaroubaceae). Lloydia 40(6): 579584. Ailanthione (1), glaucarubinone (2) and a mixture of glaucarubol 15-isovalerate (3) and 13,18-dehydroglaucarubol 15-isovalerate (4) were found to be the compounds responsible for the antitumor and cytotoxic activities of extracts of the root bark of Ailanthus excelsa (Simaroubaceae). The latter compound, 4, is new.

Rahman S., N. Fukamiya, M. Okano, K. Tagahara and K. H. Lee. 1997. Anti-tuberculosis activity of quassinoids. Chem. Pharm. Bull. (Tokyo) 45(9): 15271529. In vitro evaluation of anti-tuberculosis activity was conducted for fifty-six quassinoids isolated in our laboratory from Simaroubaceous plants, Ailanthus altissima (= Aa, 10 compounds), Brucea antidysenterica (= Ba, 16 compounds), Picrasma ailanthoides (= Pa, 14 compounds), and Brucea javanica (= Bj, 16 compounds). Of the compounds tested, shinjulactone K (1), ailanthone (2), shinjudilactone (3), and dehydrobruceantin (4) were the most potent. Although the activities were very low (0-19%), the resulting data provided a picture of structure-activity relationships.

Seida A. A., A. D. Kinghorn, G. A. Cordell and N. R. Farnsworth. 1978. Potential anticancer agents IX. Isolation of a new simaroubolide, 6alpha-tigloyloxychaparrinone, from Ailanthus integrifolia ssp. calycina (Simaroubaceae). Lloydia 41(6): 584587.