RESUMO
LC-DAD/MS-based dereplication of organic extract of a calcareous sponge Leucetta chagosensis afforded one new chiral aminoimidazole-containing alkaloid, (-)-calcaridine B (1), along with one achiral imidazole analog leucettamine E (2) as well as one known imidazole derivative (2E, 9E)-pyronaamidine-9-(N-methylimine) (3). Their structures were elucidated on the basis of NMR spectroscopic analyses, and comparing with the literature. The cytotoxic activities of all isolates were evaluated against three human cancer cell lines, and compounds 1 and 3 exhibited mild cytotoxicities toward the MCF-7 cell line with IC50 values of 25.3-24.2 µM, respectively.
Assuntos
Alcaloides , Antineoplásicos , Poríferos , Animais , Humanos , Células MCF-7 , Estrutura MolecularRESUMO
Five new imidazole derivatives (1-5), together with eight related known alkaloids, were isolated from a calcareous marine sponge, Leucetta chagosensis, collected from the South China Sea. Their structures were fully characterized by spectroscopic methods. Structurally, 1 possesses an unusual skeleton featuring imidazole and oxazolone rings linked via a nitrogen atom, whereas 2 bears an intriguing guanylurea-substituted imidazole ring. Compounds 4 and 5 were identified as zinc complexes; they represent the metal complex analogues of naamidine J (6) and pyronaamidine (7), respectively. Among the isolated compounds, 2 and 5 showed significant inhibitory activities toward the LPS-induced production of IL-6 in the human acute monocytic leukemia cell line THP-1, and 7 displayed cytotoxicity against MCF-7, PC9, A549, and breast cancer stem cells (MCF-7-Oct4-GFP) with IC50 values of 5.2, 5.6, 7.8, and 10 µM, respectively.
Assuntos
Alcaloides/farmacologia , Imidazóis/farmacologia , Poríferos/química , Zinco/metabolismo , Células A549 , Animais , Antifúngicos/farmacologia , Linhagem Celular Tumoral , China , Humanos , Interleucina-6/metabolismo , Células MCF-7 , Células THP-1RESUMO
Chemical investigation on CH2Cl2 extract of the marine sponge Leucandra sp. afforded two new compounds named leucanone A (1) and naamine J (2), together with eight known compounds (3-10). Their structures were elucidated on the basis of NMR spectroscopic analyses, and comparing with the literature. The cytotoxic activities of the compounds were evaluated against four cancer cell lines, and compound 2 showed mild cytotoxic activities against MCF-7, A549, HeLa, and PC9 cancer cell lines with IC50 values in the range of 20.1-45.3 µM.
Assuntos
Alcaloides/isolamento & purificação , Antineoplásicos/isolamento & purificação , Imidazóis/isolamento & purificação , Lipídeos/isolamento & purificação , Poríferos/química , Alcaloides/química , Alcaloides/farmacologia , Animais , Antineoplásicos/química , Antineoplásicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Éteres de Glicerila/química , Éteres de Glicerila/isolamento & purificação , Éteres de Glicerila/farmacologia , Células HeLa , Humanos , Imidazóis/química , Imidazóis/farmacologia , Concentração Inibidora 50 , Lipídeos/química , Lipídeos/farmacologia , Células MCF-7 , Biologia Marinha , Estrutura Molecular , Ressonância Magnética Nuclear BiomolecularRESUMO
Chemical investigation on CH2Cl2 extract of the marine sponge Leucetta chagosensis, collected from the South China Sea, afforded two new 5,6-epoxysterols, 5α,6α-epoxycholesta-8(14),22(E)-diene-3ß,7α-diol (1) and (24R)-24-ethyl-5α,6α-epoxycholesta-8(14),22(E)-diene-3ß,7α-diol (2) along with ten known related steroid analogs (3-12). Their structures were elucidated on the basis of NMR spectroscopic analyses, and comparison with the literature. All isolates were tested for cytotoxicity against three tumor cell lines only known compounds 11 and 12 exhibited notable cytotoxic activity against A549 (IC50: 3.0 and 5.6 µM), PC9 (2.0 and 15.6 µM), and MCF-7 (9.4 and 11.8 µM) cell lines, respectively.