Ingenamine G and Cyclostellettamines G−I, K, and L from the New Brazilian Species of Marine Sponge Pachychalina sp

• Published in: Journal of natural products (Washington, D.C.) Vol. 67; no. 10; pp. 1685 - 1689
• Main Authors: de Oliveira, Jaine H. H. L, Grube, Achim, Köck, Matthias, Berlinck, Roberto G. S, Macedo, Mario L, Ferreira, Antonio G, Hajdu, Eduardo
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.10.2004; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: Alkaloids - chemistry; Alkaloids - isolation & purification; Alkaloids - pharmacology; Animals; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - isolation & purification; Anti-Bacterial Agents - pharmacology; Antineoplastic Agents - chemistry; Antineoplastic Agents - isolation & purification; Antineoplastic Agents - pharmacology; Antitubercular Agents - chemistry; Antitubercular Agents - isolation & purification; Antitubercular Agents - pharmacology; Biological and medical sciences; Brazil; Chemistry, Medicinal; Drug Screening Assays, Antitumor; Escherichia coli - drug effects; General pharmacology; Heterocyclic Compounds, 4 or More Rings - chemistry; Heterocyclic Compounds, 4 or More Rings - isolation & purification; Heterocyclic Compounds, 4 or More Rings - pharmacology; Humans; Life Sciences & Biomedicine; Medical sciences; Microbial Sensitivity Tests; Molecular Structure; Mycobacterium tuberculosis - drug effects; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Plant Sciences; Porifera - chemistry; Science & Technology; Staphylococcus aureus - drug effects; Tumor Cells, Cultured; South America; Brazil; America; NATURAL-PRODUCTS; RENIERA-SARAI; ALKALOIDS; Antineoplastic agent; Pentacyclic compound; Angular nitrogen heterocycle; Nitrogen heterocycle; Escherichia coli; Leukemia; Cytotoxicity; Macrocycle; Marine environment; Alkaloid; Bacteria; Micrococcales; Micrococcaceae; Antituberculous agent; Colon; Mammary gland; Tumor cell; Staphylococcus aureus; Enterobacteriaceae; Human; Iminium compounds; Pharmacognosy; Animal origin; Tricyclic compound; In vitro; Biological activity; Cell line; Mycobacterium tuberculosis; Mycobacteriales; Porifera; Mycobacteriaceae; Isolation; Actinomycetes; Invertebrata; Antibacterial agent; Organic dication; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np0498713

The chemical investigation of the cytotoxic and antituberculosis active MeOH crude extract of the marine sponge Pachychalina sp. led to the isolation of six new nitrogenous metabolites, including ingenamine G (1), as well as a mixture of new cyclostellettamines G, H, I, K, and L (10−14) with the known cyclostellettamines A−F (4−9). Structural assignments of compound 1 were based on the analysis of MS and NMR data, while the structures of compounds 10−14 could be established by HPLC-MS/MS analysis. Ingenamine G displayed cytotoxic activity against HCT-8 (colon), B16 (leukemia), and MCF-7 (breast) cancer cell lines, antibacterial activity against Staphylococcus aureus (ATCC 25923), Escherichia coli (ATCC 25922), and four oxacilin-resistant S. aureus strains, and antimycobacterial activity against Mycobacterium tuberculosis H37Rv.