Dactyltronic acids from the sponge Dactylospongia elegans.
Two new cytotoxic tetronic acid derivatives with a rearranged drimane skeleton [1a and 1b], were isolated from the sponge Dactylospongia elegans, along with smenospongic acid [3], illimaquinone [4], dactylospongenones A, B, C, and D [5], and dictyoceratin C [6]. The structures of 1a and 1b were elucidated by spectroscopic and chemical methods. Treatment of 1 with base gave smenospongic acid [3], suggesting that this latter compound is an end-product of D. elegans metabolism. A biogenetic route from furoterpenes to the tetronic acids [1a and b] and smenospongic acid [3] is proposed.
Departamento de Química Orgánica, Facultad de Química, Universidad de Santiago, Spain.
M D
MD
López
E
E
Quiñoá
R
R
Riguera
D000818:Animals; D000970:Antineoplastic Agents / Q000302:isolation & purification* / Q000494:pharmacology; D005663:Furans / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D007941:Leukemia P388 / Q000188:drug therapy; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D011161:Porifera / Q000737:chemistry*; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D005663:Furans; C003422:tetronic acid