Three new cyclic peroxides from the marine sponge Plakortis aff simplex.
In our continuing program to identify bioactive compounds from marine invertebrates, the MeOH-EtOAc (1:1) extract of the sponge Plakortis aff simplex, collected in Madagascar, was found to be cytotoxic to a series of human tumor cells. From this sponge, three new compounds and one known one, two new 1,2-dioxane peroxylactones named plakortolides H (1) and I (2), and one new 1,2-dioxolane, designated andavadoic acid (3), have been isolated and their structures elucidated. In addition, the known N(3)-methyladenine (4) was isolated, to the best of our knowledge, for the first time from a marine source. Andavadoic acid (3) showed significant activity against 13 tumor cells with GI(50) values in the submicromolar range.
Rudi
Amira
A
School of Chemistry, Tel-Aviv University, Ramat Aviv 69978, Israel.
Afanii
Rania
R
Gravalos
Lola Garcia
LG
Aknin
Maurice
M
Gaydou
Emile
E
Vacelet
Jean
J
Kashman
Yoel
Y
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006573:Heterocyclic Compounds, 1-Ring / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006574:Heterocyclic Compounds, 2-Ring / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D008270:Madagascar; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010545:Peroxides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D011161:Porifera / Q000737:chemistry*; D014407:Tumor Cells, Cultured / Q000187:drug effects
D000970:Antineoplastic Agents; D006573:Heterocyclic Compounds, 1-Ring; D006574:Heterocyclic Compounds, 2-Ring; D010545:Peroxides; C478291:andavadoic acid; C478289:plakortolide H; C478290:plakortolide I