In vitro Anticancer Activities of Some Triterpene Glycosides from Holothurians of Cucumariidae, Stichopodidae, Psolidae, Holothuriidae and Synaptidae families.

Triterpene glycosides isolated from holothurians are natural products known to possess cytotoxic properties against cancer cells. However, their anticancer prophylactic activity has not been studied sufficiently. The anticancer prophylactic; cytotoxic, and pro-apoptotic properties of 18 triterpene glycosides, as well as their effects on the transcriptional activities of activator protein-I (AP-1) and nuclear factor-KB (NF-KB), were examined using methods that included EGF-induced JB6 C141 P' cell transformation in soft agar, flow cytometry, MTS assessment of cell viability, and a luciferase activity assay. The compounds inhibited EGF-induced neoplastic JB6 C141 P' cell transformation in soft agar and caused apoptosis and necrosis of human HL-60 and THP-I leukemia cells. AP- and NF-KB were involved in the cellular response to the treatment by the compounds. Conclusion: glycosides isolated from holothurians of Cucumariidae, Stichopodidae, Psolidae, Holothuriidae and Synaptidae families have potential for development as new antitumor agents and as instruments to study AP-I and NF-kB.

Absolute Configuration and Body Part Distribution of the Alkaloid 6-epi-Monanchorin from the Marine Polychaete Chaetopterus variopedatus.

As a result of the first study on secondary metabolites from the cosmopolitan bioluminescent marine tube polychaete Chaetopterus variopedatus, a new bicyclic guanidine alkaloid, 6-epi-monanchorin (1), along with the previously known monanchorin (2) were isolated. The structure of 1 was elucidated by spectroscopic and chemical methods, including a cleavage of the C1-07 bond to obtain a secondary alcohol (3), which was used to determine the absolute configurations by Mosher's method. It was found that 1 and 2 were mainly accumulated in a secreted mucus special organ of the worm (food net), where green and blue-green microalgae were detected. A biosynthetic pathway to 6-epi-monanchorin and monanchorin from dietary polyeic fatty acid precursors was proposed.

Monanchomycalin C, a new pentacyclic guanidine alkaloid from the far-eastern marine sponge Monanchora pulchra.

A new pentacyclic guanidine alkaloid, monanchomycalin C (1), along with the earlier known ptilomycalin A (2), were isolated from the Far-Eastern marine sponge Monanchora pulchra. The structure of 1 was elucidated using 1D and 2D NMR spectroscopic and ma ss spectrometric da ta. Compounds 1 and 2 exhibited cytotoxic activities against human breast cancer MDA-MB-231 cells with IC50 values of 8.2 microM and 4.3 pM, respectively.

A new antimicrobial and anticancer peptide producing by the marine deep sediment strain "Paenibacillus profundus" sp. nov. Sl 79.

A new linear glyceryl acid derived heptapeptide (1), together with known isocoumarin antibiotic, Y-05460M-A (2), were isolated from the culture of the deep sea sediment strain SI 79 classified as "Paenibacillus profundus" sp. nov. Their structures were determined by 1D- and 2D- NMR techniques and ESI-MS/MS experiments. HPLC analysis of the Marfey derivatives in comparison to their analogs of authentic amino acids revealed that all amino acids in peptide 1, with an exception of Val, have the D-configuration. The compound 1 showed inhibitory activity against Staphylococcus aureus, Staphylococcus epidermidis, Bacillus subtilis, Enterococcus faecium as well as cytotoxic and moderate colony growth inhibitory activity against SK-MEL-28 cell line.

New meroterpenoids from the marine sponge Aka coralliphaga.

Three new sulfated meroterpenoids containing sesquiterpene and hydroquinone moieties, namely siphonodictyal A sulfate (1), akadisulfate A (2) and akadisulfate B (3), along with the known siphonodictyal B3 and bis(sulfato)-cyclosiphonodictyol A were isolated from the sponge Aka coralliphaga. Their structures were elucidated on the basis of spectroscopic data. Akadisulfate B and siphonodictyal B3 showed a radical-scavenging activity comparable with that of the known lipophylic antioxidant BHT.

Three new aaptamines from the marine sponge Aaptos sp. and their proapoptotic properties.

Three new aaptamine-type alkaloids, 2,3-dihydro-2,3-dioxoaaptamine (1), 6-(N-morpholinyl)-4,5-dihydro-5-oxo-demethyl(oxy)aaptamine (2) and 3-(methylamino)demethyl(oxy)aaptamine (3), along with known aaptamines were isolated from the sponge Aaptos sp. Their structures were determined on the basis of detailed analysis of their 1D and 2D NMR spectroscopic and mass spectral data. The isolated compounds induced apoptosis in human leukemia THP-1 cells.

Aaptamine alkaloids from the Vietnamese sponge Aaptos sp.

A series of aaptamines, including one new alkaloid (1), were isolated from the marine sponge Aaptos sp. collected in Vietnamese waters. The structure of 1 was elucidated using NMR and HRESIMS, as well as by chemical transformation of 1 to the previously known aaptamine and established as 3-N-morpholinyl-9-demethyl(oxy)aaptamine. The isolated compounds showed a potential cancer preventive activity.