Dehydrobruceantin

Chem Pharm Bull (Tokyo). 1997 Sep;45(9):1527-9.

Anti-tuberculosis activity of quassinoids.[Pubmed: 9332005]

METHODS AND RESULTS:
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).
CONCLUSIONS:
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.

J. Org. Chem.,1975,40(5):648–654.

The isolation and structural elucidation of bruceantin and bruceantinol, new potent antileukemic quassinoids from Brucea antidysenterica[Reference: WebLink]

METHODS AND RESULTS:
The isolation and structural elucidation of the new potent antileukemic principles, bruceantin (1) and bruceantinol (3), and the new companion quassinoids, bruceantarin (2), Dehydrobruceantin (8), dehydrobruceantarin (9), dehydrobruceine B (10), dehydrobruceantol (11), and isobruceine B (12), are reported. Bruceantin (1), bruceantinol (3), and bruceantarin (2) were shown by hydrolysis to be trans-3,4-dimethyl-2-pentenoate, trans-4-hydroxy-3,4-dimethyl-2-pentenoate, and benzoate esters, respectively, of bruceolide (5).
CONCLUSIONS:
The dehydro compounds were shown to have a 2-hydroxy-3-keto-4-methylcyclohexa-1,4-diene A ring, a feature new to the quassinoids. Isobruceine B (12) was shown to be an A-ring isomer of the known bruceine B (4).