papuamine and haliclonadiamine

Four new haliclonadiamine analogues, (10Z,12E)-haliclonadiamine (1), (10E,12Z)-haliclonadiamine (2), and halichondriamines A (3) and B (4), were isolated from the Okinawan marine sponge Halichondria panicea together with haliclonadiamine (5) and papuamine (6). The structures of 1-4 were elucidated on the basis of their spectroscopic data by comparisons with those for 5 and 6. Further separation of the remaining fraction led to the isolation of a new bicyclic guanidine alkaloid, 6-epi-monanchorin (7), along with monanchorin (8). Compound 7 is the epimer of 8 at the 6 position. Compounds 1-6 inhibited the growth of Mycobacterium smegmatis with inhibition zones of 12, 7, 8, 7, 16, and 12 mm at 10 μg/disc, respectively. Compounds 2-4 exhibited weak cytotoxicities against the Huh-7 (hepatoma) human cancer cell line and were 2-fold less active than 5 and 6. Compounds 7 and 8 were not active against M. smegmatis at 20 μg/disc or the cancer cell line at 10 μM.

Topics: Alkaloids; Animals; Antineoplastic Agents; Bridged Bicyclo Compounds, Heterocyclic; Carcinoma, Hepatocellular; Drug Screening Assays, Antitumor; Guanidine; Guanidines; Humans; Japan; Marine Biology; Microbial Sensitivity Tests; Molecular Structure; Mycobacterium smegmatis; Porifera

Two new polycyclic alkaloids, neopetrocyclamines A and B (1 and 2), along with the known metabolites papuamine (3) and haliclonadiamine (4), were isolated from the Indonesian sponge Neopetrosia cf exigua. Neopetrocyclamine A contains a formamidinium moiety, a rare functional group. While these compounds share the same basic biosynthetic building blocks, the size of the ring system differs in 1 and 2 because of the formamidinium moiety. Biological evaluations of 1-4 revealed that papuamine is cytotoxic against glioblastoma SF-295 cells (GI50 = 0.8 μM).

Topics: Alkaloids; Animals; Antineoplastic Agents; Diamines; Drug Screening Assays, Antitumor; Humans; Indonesia; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Polycyclic Compounds; Porifera

The extract of an Indonesian marine sponge Haliclona sp. showed potent cytotoxicity against human solid cancer cell lines, MCF-7 (breast), LNCap (prostate), Caco-2 (colon) and HCT-15 (colon) cells. Study on nuclear morphological changes and flow cytometric analysis suggested that the component(s) in the extract would induce an apoptosis to these cancer cells. Bioassay-guided isolation yielded two pentacyclic alkaloids, papuamine (1) and haliclonadiamine (2), which inhibited cell proliferation of six human cancer cell lines with IC50 values of 0.93-1.50 and 1.00-4.44 µM, respectively. Compounds 1 and 2 accumulated lymphoma U937 cells at sub-G1 phase and induced a condensation of chromatin and fragmentation of nucleus.

Topics: Alkaloids; Animals; Antineoplastic Agents; Cell Line, Tumor; Humans; Porifera