Ingenamine G and Cyclostellettamines G−I, K, and L from the New Brazilian Species of Marine SpongePachychalinasp.

Abstract

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.

Natural Products from Marine Invertebrates and Microorganisms in Brazil between 2004 and 2017: Still the Challenges, More Rewards

“…Ingenamine G (89) displayed cytotoxic activity against HCT-8 (colon), B16 (leukemia) and MCF-7 (breast) at 8.6, 9.8 and 11.3 µg mL -1 , respectively. 51 Investigation on the cytotoxic mechanismof-action of compound 89 indicated that it promotes DNA-damage, especially in S-phase of the cell-cycle. The n-BuOH extract of P. alcaloidifera yielded a mixture of eleven 3-alkylpyridine compounds, cyclostellettamines A-I, K and L (90-100), among which alkaloids 96-100 are new representatives of this class.…”

Total Synthesis of (±)‐Haliclonacyclamine C

“…Fontana and co-workers were able to feed the mollusc Haminoea orbignyana with radio-labelled [2-14 C]-acetic acid and nicotinic acid-carboxy- 14 C. After injection of the labeled precursors they detected significant levels of radioactivity in the isolated haminol-2 (1.69). They also administered to the mollusc d 4 .…”

Metabólitos secundários das esponjas Aplysina fistularis e Dysidea sp. e atividade antituberculose da 11-cetofistularina-3

“…A fração Dv-hex-5B (0,011 g) apresentou composto majoritário ainda impuro, e foi purificada por CLAE (coluna: Waters m-Porasil sílica gel 5 mm, 19 x 300 mm; eluente: n-hexano/AcOEt/MeOH 80:18:2; fluxo: 1 mL/min; detecção: UV l max 254 nm). Obteve-se 1,4 mg da lactona da furodisinina (14). 40 As outras frações obtidas do extrato hexânico apresentaram somente esteróis, esteroides, ésteres do glicerol e ácidos graxos e não foram investigadas.…”

“…por partição líquido-líquido e por uma série de separações cromatográficas (ver Parte Experimental) levou ao isolamento da lactona da furodisinina (14) e ao esterol 9a,11a-epoxicolest-7-eno-3b,5a,6a,10-tetrol-6-acetato (15). A lactona da furodisinina 14 foi originalmente isolada da esponja Dysidea etheria.…”

“…Além disso, a investigação química do extrato ativo contra M. tuberculosis da esponja Dysidea sp., também realizado pela primeira vez, levou-nos a obter a lactona da furodisinina (14) e o esterol altamente oxigenado 15, dos quais o último mostrou ser inativo no teste de atividade antituberculose.…”