Jaine H. H. L. de Oliveira, Achim Grube, Matthias Köck, Roberto G. S. Berlinck, Mario L. Macedo, Antonio G. Ferreira, Eduardo Hajdu, “Ingenamine G and Cyclostellettamines G-I, K, and L from the New Brazilian Species of Marine Sponge Pachychalina sp.”, J. Nat. Prod. , 2004, 67, 1685-1689.

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.

Jaine H. H. L. de Oliveira, Mirna, H. R. Seleghim, C. Timm, Achim Grube, Matthias Köck, Gislene G. F. Nascimento, A. C. T. Martins, E. G. O. Silva, Ana O. de Souza, Fabio C. S. Galetti, Paulo R. R. Minarini, Celio L. Silva, Eduardo Hajdu, Roberto G. S. Berlinck, “Antimicrobial and Antimycobacterial Activity of Cyclostellettamine Alkaloids from Sponge Pachychalina sp.”, Marine Drugs, 2006, 4, 1-8.

Abstract: Cyclostellettamines A – F (1 – 6) isolated from the sponge Pachychalina sp. and cyclostellettamines G – I, K and L (7 – 11) obtained by synthesis were evaluated in bioassays of antimicrobial activity against susceptible and antibiotic-resistant Staphylococcus aureus, Pseudomonas aeruginosa and antibiotic-susceptible Escherichia coli and Candida albicans, as well as in antimycobacterial activity against Mycobacterium tuberculosis H37Rv bioassays. The results obtained indicated that cyclostellettamines display different antimicrobial activity depending on the alkyl-chain size, suggesting that, if a mechanism-of action is implied, it is dependent on the distance between the two pyridinium moieties of cyclostellettamines.

Ulisses S. Pinheiro, Roberto G. S. Berlinck, Eduardo Hajdu, “Shallow-water Niphatidae (Haplosclerina, Haplosclerida, Demospongiae)from the São Sebastião Channel and its environs (tropical southwestern Atlantic), with the description of a new species.”, Contributions to Zoology, 2005, 74, 271-278.

Abstract: Two niphatids are described here: Amphimedon viridis and Pachychalina alcaloidifera sp. nov. Amphimedon viridis is a common and conspicuous species in most of the tropical western Atlantic. Pachychalina alcaloidifera sp. nov. has this far been found only in the coasts of Rio de Janeiro and São Paulo states. Both species are described on the basis of series of specimens observed alive.

Jaine H. H. L. de Oliveira, Andréa M. Nascimento, Hiriam H. Kossuga, Bruno C. Cavalcanti, Claudia Pessoa, Manoel O. Moraes, Mario L. Macedo, Antonio G. Ferreira, Eduardo Hajdu, Ulisses S. Pinheiro, Roberto G. S. Berlinck, “Cytotoxic Alkylpiperidine Alkaloids from the Brazilian Marine Sponge Pachychalina alcaloidifera”, Journal of Natural Products, 2007, 70, 538-543.

Abstract: 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.

Bruno C. Cavalcanti, C. M. L. Sombra, Jaine H. H. L. de Oliveira, Roberto G. S. Berlinck, Manoel O. Moraes, Claudia Pessoa, “Cytotoxicity and genotoxicity of ingenamine G isolated from the Brazilian marine sponge Pachychalina alcaloidifera” . Comparative Biochemistry and Physiology , 2008, 147, 409-415.

Abstract: Marine sponges belonging to the order Haplosclerida are one of the more prolific sources of new natural products possessing various biological activities. The present study examined the cytotoxic and genotoxic potential of ingenamine G, an alkaloid isolated from the Brazilian marine sponge Pachychalina alcaloidifera. Ingenamine G displayed a moderate cytotoxic activity against human proliferating lymphocytes evaluated by the MTT assay (IC50 15 μg/mL). The hemolytic assay showed that ingenamine G cytotoxic activity was not related to membrane disruption. The comet assay and chromosome aberration analysis were applied to determine the genotoxic and clastogenic potential of ingenamine G, respectively. Cultured human lymphocytes were treated with 5, 10, 15 and 20 μg/mL of ingenamine G during the G1, G1/S, S (pulses of 1 and 6 h), and G2 phases of the cell cycle. All tested concentrations were cytotoxic, reduced significantly the mitotic index, and were clastogenic in all phases of the cell cycle, especially in S phase. While an increase in DNA-strand breaks was observed starting with the concentration corresponding to the IC50. The presence of genotoxicity and polyploidy during interphase and mitosis, respectively, suggests that ingenamine G at high concentrations is clastogenic and indirectly affects the construction of mitotic fuse.