New nitrogenous eudesmane-type compounds isolated from the Caribbean sponge Axinyssa ambrosia.
Fractionation of an acetone-methanol (1:1) extract of the Caribbean marine sponge Axinyssa ambrosia yielded three new sesquiterpenes whose structures were established by spectroscopic methods as (4R*,5R*,7S*,10R*)-eudesm-11-en-4-ylamine hydrochloride (1), axinyssamine hydrochloride, (4R*,5R*,7S*,10R*)-4-isocyanatoeudesm-11-ene (3), and (4R*,5R*,7S*,10R*)-formamidoeudesm-11-ene (4). Compound 1 exhibited significant cytotoxic activity against cancer cells and was also active in a lethality test using polyps of the scleractinian coral Madracis mirabilis.
Petrichtcheva
Natalia V
NV
Departamento de Química, Universidad Nacional de Colombia, AA 14490, Bogotá, Colombia.
Duque
Carmenza
C
Dueñas
Adriana
A
Zea
Sven
S
Hara
Noriyuki
N
Fujimoto
Yoshinori
Y
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D003063:Cnidaria / Q000187:drug effects; D003105:Colombia; D003110:Colonic Neoplasms; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007941:Leukemia P388; D008175:Lung Neoplasms; D051379:Mice; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D045787:Sesquiterpenes, Eudesmane; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured / Q000187:drug effects
C464611:(4R*,5R*,7S*,10R*)-eudesm-11-en-4-ylamine hydrochloride; D012717:Sesquiterpenes; D045787:Sesquiterpenes, Eudesmane; C464613:axinyssamine hydrochloride, (4R*,5R*,7S*,10R*)-4-isocyanato-eudesm-11-ene; C464612:formamidoeudesm-11-ene