Bioactive Pyridoacridine Alkaloids from the Micronesian SpongeOceanapiasp.

Abstract

The Micronesian sponge Oceanapia sp. afforded three pyridoacridine alkaloids: the known compounds kuanoniamine C (1) and kuanoniamine D (2), as well as the new N-deacyl derivative (3) of the kuanoniamines. Compounds 1 and 2 exhibited insecticidal activity toward neonate larvae of the polyphagous pest insect Spodoptera littoralis (LC50 of 156 and 59 ppm, respectively), when incorporated into artificial diet. Both compounds also showed toxicity in the brine shrimp lethality test with a LC50 of 37 micrograms/mL (compound 1) and 19 micrograms/mL (compound 2), respectively. The N-deacyl derivative did not show any remarkable effect in both bioassays. Cytotoxcity of the alkaloids was studied in vitro, using two human cell lines. The new derivative (3) appeared to be active in the same range of concentrations as kuanoniamine C (1) and D (2). The IC50 of 3 was 1.2 micrograms/mL toward HeLa cells and 2.0 micrograms/mL toward MONO-MAC 6 cells. In receptor binding assays compound 2 showed affinity to A1- and A2A-adenosine receptors with Ki values of 2.94 and 13.7 microM, respectively. Compound 1 was less active than compound 2, whereas compound 3 showed no affinity toward adenosine receptors. In addition, compounds 1-3 exhibited moderate affinity to benzodiazepine binding sites of GABAA receptors.

Marine pyridoacridine alkaloids and synthetic analogues as antitumor agents

“…Three shermilamines D (17), E (18) 9 and cycloshermilamine (19) 10 corresponding to the same biosynthetic pathway have recently been reported from Cystodytes violatinctus (Fig. 2).…”

Anticancer Activity Evaluation of Kuanoniamines A and C Isolated from the Marine Sponge Oceanapia sagittaria, Collected from the Gulf of Thailand

“…On the contrary, kuanoniamine C (7) has been reported later from Oceanapia sagittaria [9,11] and from the Micronesian sponge Oceanapia sp. [12] and was found to exhibit significant in vitro cytotoxicity to Hela and MONO-MAC 6 tumour cells [10]. On the other hand, 24α-methylcholestanol (1) is one of the common marine sterols while phydroxybenzaldehyde (2), p-hydroxybenzoic acid (3), phenylacetic acid (4) and 3-formylindole (5) are probably degradation products of the secondary metabolites and have been commonly found in many marine sponges.…”

“…While kuanoniamine C, together with sagitol, were found to be the major constituents of the marine sponge O. sagitaria from Palau [9], kuanoniamines C and D and their N-acetyl derivative were also isolated from the Micronesian sponge Oceanapia sp. [10]. Interestingly, kuanoniamine C was shown to be produced by the sponge cells and not by intracellular symbiotic organisms of O. sagittaria [11].…”

Chemical and bioactive diversities of marine sponge <i>Neopetrosia</i>

“…Previous reports showed that pyridoacridine alkaloids are produced by other marine sponge including Oceanapia sp. (Eder et al, 1998), Petrosia sp (Nukoolkarn et al, 2008) and from ascidian species such as Cystodytes dellechiajei (Torres et al, 2002) and Lissoclinum cf. Badium (Clement et al, 2008).…”