Aplysfistularine: a novel dibromotyrosine derivative isolated from Aplysina fistularis

Abstract

Recebido em 7/3/12; aceito em 31/7/12; publicado na web em 15/10/12The new dibromotyrosine derivative 3,5-dibromo-4-[3'dimethylamonium]propoxyphenyl]-N,N,N-trimethylethanamonium, here referred to as aplysfistularine (1), was isolated from the marine sponge Aplysina fistularis along with 2-(3,5-dibromo-4-methoxyphenyl)-N,N,N-trimethylethanamonium (2), aplysterol (3) and 24,28-didehydroaplysterol (4). Their identification was performed by mass spectrometry, infrared, 1 H and 13 C NMR, and by comparison with literature data. Compound 2 and the mixture of 3 and 4 were tested in vitro (inhibitory activity) with supercoiled DNA relaxation techniques, and showed inhibitory activity on human DNA topoisomerase II-α. Compound 1 was not tested due to paucity of the material.

Isolation and structure elucidation of natural products of three soft corals and a sponge from the coast of Madagascar

“…76,77 Aplysterol (13) was previously isolated from other marine sponges, e.g. Aplysina aerophoba 78 and Aplysina fistularis, 77,79 and also from terrestrial plants, such as Mussaenda macrophylla, 80 but not from P. arabica. Further fractionation of the dichloromethane extract (F-2) of P. arabica followed by column chromatography over silica gel afforded additional aplysterol (13) and a mixture of the dibromotyrosine metabolites 14a and 14b (Fig.…”

Natural Products from Marine Invertebrates and Microorganisms in Brazil between 2004 and 2017: Still the Challenges, More Rewards

“…The salt 131 inhibited human DNA topoisomerase II-a at concentration of 100 µM. 78 Investigation of the MeOH extract of Petromica citrina provided halistanol (167, Figure 19) and halistanol sulfate C (168, Figure 19). 79 Compounds 167 and 168 presented inhibitory effects on the replication of the Herpes Simplex Virus type 1 (HSV-1, KOSstrain), with IC 50 at 5.63 µg mL -1 (selectivity index (SI) = 2.46) and 6.09 µg mL -1 (SI = 1.95), respectively, while the fraction that contained these compounds as the major constituents displayed antiviral activity with IC 50 at 2.87 µg mL -1 (SI = 15.33), suggesting that the anti-HSV-1 activity of the fraction is possibly related to the synergistic effects of compounds 167 and 168.…”