Ingenamine G and cyclostellettamines G-I, K, and L from the new Brazilian species of marine sponge Pachychalina sp.
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.
de Oliveira
Jaine H H L
JH
Instituto de Química de São Carlos, Universidade de São Paulo, CP 780, CEP 13560-970, Brazil.
Grube
Achim
A
Köck
Matthias
M
Berlinck
Roberto G S
RG
Macedo
Mario L
ML
Ferreira
Antonio G
AG
Hajdu
Eduardo
E
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000995:Antitubercular Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001938:Brazil; D004354:Drug Screening Assays, Antitumor; D004926:Escherichia coli / Q000187:drug effects; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D011161:Porifera / Q000737:chemistry*; D013211:Staphylococcus aureus / Q000187:drug effects; D014407:Tumor Cells, Cultured
D000470:Alkaloids; D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D000995:Antitubercular Agents; D006576:Heterocyclic Compounds, 4 or More Rings; C493695:ingenamine G