Three New Cyclic Peroxides from the Marine Sponge Plakortis aff simplex

• Published in: Journal of natural products (Washington, D.C.) Vol. 66; no. 5; pp. 682 - 685
• Main Authors: Rudi, Amira, Afanii, Rania, Gravalos, Lola Garcia, Aknin, Maurice, Gaydou, Emile, Vacelet, Jean, Kashman, Yoel
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01-05-2003; Glendale, AZ American Society of Pharmacognosy
• Subjects: 1,2-dioxane peroxylactone; 1,2-dioxolane; andavadoic acid; animal products; Animals; Antineoplastic Agents - chemistry; Antineoplastic Agents - isolation & purification; Antineoplastic Agents - pharmacology; Biological and medical sciences; carbon; cell lines; chemical structure; cytotoxicity; Drug Screening Assays, Antitumor; General pharmacology; Heterocyclic Compounds, 1-Ring - chemistry; Heterocyclic Compounds, 1-Ring - isolation & purification; Heterocyclic Compounds, 1-Ring - pharmacology; Heterocyclic Compounds, 2-Ring - chemistry; Heterocyclic Compounds, 2-Ring - isolation & purification; Heterocyclic Compounds, 2-Ring - pharmacology; Humans; Inhibitory Concentration 50; lactones; Madagascar; Medical sciences; Molecular Structure; n-methyladenine; natural products; Nuclear Magnetic Resonance, Biomolecular; peroxide; peroxides; Peroxides - chemistry; Peroxides - isolation & purification; Peroxides - pharmacology; peroxylactone; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Plakortis aff simplex; plakortolide H; plakortolide I; plakortolides; Porifera; Porifera - chemistry; protons; spectral analysis; stereochemistry; Tumor Cells, Cultured - drug effects; vinylbenzene; Madagascar; Malagasy Republic; Africa; ISW, Madagascar; Antineoplastic agent; Human; Pharmacognosy; Animal origin; Cytotoxicity; Lactone; Oxygen heterocycle; Screening test; In vitro; Biological activity; Marine environment; Cell line; Porifera; Carboxylic acid; Bicyclic compound; Isolation; Invertebrata; Tumor cell; Organic peroxide; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np020589a

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 GI50 values in the submicromolar range.