Cytotoxic Alkylpiperidine Alkaloids from the Brazilian Marine Sponge Pachychalina alcaloidifera

• Published in: Journal of natural products (Washington, D.C.) Vol. 70; no. 4; pp. 538 - 543
• Main Authors: de Oliveira, Jaine H. H. L, Nascimento, Andréa M, Kossuga, Miriam H, Cavalcanti, Bruno C, Pessoa, Claudia O, Moraes, Manoel O, Macedo, Mario L, Ferreira, Antonio G, Hajdu, Eduardo, Pinheiro, Ulisses S, Berlinck, Roberto G. S
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.04.2007; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: alkaloids; Alkaloids - chemistry; Alkaloids - isolation & purification; Alkaloids - pharmacology; Animals; anticarcinogenic activity; Antineoplastic Agents - chemistry; Antineoplastic Agents - isolation & purification; Antineoplastic Agents - pharmacology; arenosclerin; Biological and medical sciences; Brazil; chemical structure; Chemistry, Medicinal; cultured cells; cytotoxicity; Drug Screening Assays, Antitumor; Female; General pharmacology; haliclonacyclamine; Haplosclerida; Humans; Life Sciences & Biomedicine; madangamine; Marine Biology; Medical sciences; Molecular Structure; Pachychalina; Pachychalina alcaloidifera; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; piperidine alkaloids; Piperidines - chemistry; Piperidines - isolation & purification; Piperidines - pharmacology; Plant Sciences; Porifera; Porifera - chemistry; pyridine alkaloids; Science & Technology; stereochemistry; Brazil; South America; America; METABOLITES; INVASION; MOIETY; ABSOLUTE-CONFIGURATION; MOTUPORAMINES; A-C; Antineoplastic agent; Pentacyclic compound; Aminoalcohol; Angular nitrogen heterocycle; Pharmacognosy; Animal origin; Cytotoxicity; Tetracyclic compound; In vitro; Biological activity; Marine environment; Alkaloid; Cell line; Porifera; Piperidine derivatives; Isolation; Invertebrata; Tumor cell; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np060450q

Four bis-piperidine alkaloids, madangamine F (1), haliclonacyclamine F (2). and arenosclerins D (3) and E (4), have been isolated from the marine sponge Pachychalina alcaloidifera and have been identified by analysis of spectroscopic data. The alkaloids displayed cytotoxic activity against different cancer cell lines. These results support the hypothesis of a common biogenetic origin for the Haplosclerida bis-piperidine and bis-pyridine alkaloids.