Haouamines A and B: a new class of alkaloids from the ascidian Aplidium haouarianum.
The chemical study of the ascidian Aplidium haouarianum has led to the isolation of the new metabolites haouamines A (1) and B (2) which belong to a novel class of alkaloids. The structure of 1 was established by interpretation of its spectroscopic data and those of the N-methyl derivative 3, and confirmed by X-ray crystallographic analysis. The structure of 2 was deduced by spectroscopic study of its peracetyl derivative 2a. In solution each haouamine exists as an unseparable mixture of two interconverting isomers derived by the presence of a highly strained 3-aza-[7]-paracyclophane moiety in their structures. Compound 1 exhibits a selective cytotoxic activity against the HT-29 human colon carcinoma cell line.
Garrido
Leda
L
Departamento de Química Orgánica, Facultad de Ciencias del Mar y Ambientales, Universidad de Cádiz, Apdo. 40, 11510-Puerto Real, Spain.
Zubía
Eva
E
Ortega
María J
MJ
Salvá
Javier
J
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D003110:Colonic Neoplasms; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D004727:Endothelium / Q000187:drug effects; D006254:Hawaii; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D008175:Lung Neoplasms; D008297:Male; D051379:Mice; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011471:Prostatic Neoplasms; D013030:Spain; D014407:Tumor Cells, Cultured / Q000187:drug effects; D014561:Urochordata / Q000737:chemistry*; D000097566:Cyclophanes
D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; C474767:haouamine A; D000097566:Cyclophanes; C474768:haouamine B