UBC Theses and Dissertations

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UBC Theses and Dissertations

Biologically active secondary metabolites from tropical marine invertebrates Dewi, Ariyanti Suhita


In our effort to discover promising anticancer agents, we have screened a series of compounds for their activities as indoleamine-2,3-dioxygenase (IDO) inhibitor and SHcontaining inositol 5-phosphatase (SHIP1) activator. In comparison to aaptamine (2.1) and demethylaaptamine (2.2), isoaaptamine (2.4) from Aaptos cf. suberitoides appears to be the most promising IDO inhibitor with an IC₅₀ of 0.00215 mg/mL, owing to the presence of hydroxyl group at C9 position and the methylation at N1 position. A study on the sponge extract of RJA 55275 for its SHIP activator yielded theonellapeptolide Id (3.4), the first peptide that enhanced the SHIP with 25% activity at concentration 124 μM, thus makes it the most potent SHIP activator known to date. The third project studied the crystals of a novel eunicellin-based diterpenoid (4.39) with a modest SHIP activity from an unidentified Micronesian soft coral RJA 47686. The X-ray analysis illustrated that the crystals are monoclinic, space group P21/b, with a = 9.3711(14) A; α = 90⁰; b = 13.5349(17) A; β = 99.142(7)⁰; c = 10.9891(17) A; γ = 90⁰; V = 1376.1 (3) ų; Z value = 2; Dcalc 1.189. 10-³ g/cm³; F₀₀₀ 536.00; Cu (MoKα) 0.84 cm-¹. Based on the NMR and x–ray data 4.39 was shown to possess (1R*, 2R*, 3R*, 6R*, 7S*, 10R*, 14R*, 18R*)-configuration with an ether linkage connecting C2 and C6.

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