Three New Pseudodistomins, Piperidine Alkaloids from the Ascidian Pseudodistoma megalarva

• Published in: Journal of natural products (Washington, D.C.) Vol. 60; no. 10; pp. 986 - 990
• Main Authors: Freyer, Alan J, Patil, Ashok D, Killmer, Lew, Troupe, Nelson, Mentzer, Mary, Carte, Brad, Faucette, Leo, Johnson, Randall K
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.10.1997; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: ADN; AGENTES ANTINEOPLASTICOS; ALCALOIDE; ALCALOIDES; ALKALOIDS; Alkaloids - isolation & purification; Alkaloids - pharmacology; ANIMAL AQUATIQUE; ANIMALES ACUATICOS; Animals; ANTINEOPLASTIC AGENTS; AQUATIC ANIMALS; BELAU; Biological and medical sciences; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; Chemistry, Medicinal; Chromatography, Thin Layer; COMPOSE ORGANOAZOTE; COMPOSICION QUIMICA; COMPOSITION CHIMIQUE; COMPUESTO ORGANICO DEL NITROGENO; DNA; DNA MODIFICATION; DNA REPAIR; DNA Repair - drug effects; DNA, Fungal - biosynthesis; ESPECTROMETRIA; ESTRUCTURA QUIMICA; General pharmacology; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; MARINE ANIMALS; Medical sciences; MEDICAMENT CYTOSTATIQUE; Mutagenicity Tests; Mutagens - isolation & purification; Mutagens - pharmacology; OCEANIA; OCEANIE; ORGANIC NITROGEN COMPOUNDS; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Piperidines - isolation & purification; Piperidines - pharmacology; Plant Sciences; Science & Technology; SPECTRAL ANALYSIS; SPECTROMETRIE; SPECTROMETRY; STRUCTURE CHIMIQUE; Urochordata - chemistry; Yeasts - drug effects; Yeasts - genetics; Micronesia; Oceania; CAMPTOTHECIN; TOPOISOMERASE-I; KANOKO; Aminoalcohol; Yeast; Aliphatic compound; Nitrogen heterocycle; Epimer; Animal origin; Prochordata; Biological activity; Urochordata; Marine environment; Alkaloid; Double stranded DNA; Polyenic compound; Conjugated dienic compound; Isolation; Invertebrata; Repair; Structural analysis
• DOI: 10.1021/np9701438
• ISSN: 0163-3864

Bioassay-guided fractionation of the MeOH−CH2Cl2 extract of the Micronesian ascidian Pseudodistoma megalarva yielded three new piperidine alkaloids, pseudodistomins D−F (3−5) and the previously reported pseudodistomins B and C (1 and 2). The structure and stereochemistry of these compounds were established by interpretation of spectral data. Pseudodistomins B−F were found to be active in a cell-based assay for DNA damage induction, but the activity was due to an alternative mechanism.