Aaptamine (1) and isoaaptamine (2) were isolated from the marine sponge Aaptos aaptos; 6-bromo-2′-de-N-methylaplysinopsin (3) from the marine sponge Hyrtios sp. Alkaloids 1–3 were tested for the ability to trap 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical, to reduce Folin–Ciocalteau reagent (FCR), and to inhibit oxidation of linoleic acid (LA) induced by peroxide radicals. Compounds 1 (IC50 18 μM), 2 (IC50 16 μM), and 3 (IC50 18 μM) reacted strongly with DPPH, comparable with trolox (IC50 16 μM) and showed high reducing ability for FCR. The inhibition of LA oxidation by 1–3 was comparable with that of ionol (BHT). It was shown that the antioxidant activity of 1–3 was related to their ability to release both electrons and H atoms.
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The work was supported by grants 09-III-A-05-145 (FEB RAS), NSh-2813.2008.4 (State Foundation for Support of Leading Scientific Schools of the RF), and the RAS Presidium Program “Molecular and Cellular Biology.”
Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 712–715, November–December, 2009.
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Utkina, N.K. Antioxidant activityofaromatic alkaloids from the marine sponges Aaptos aaptos and Hyrtios SP.. Chem Nat Compd 45, 849–853 (2009). https://doi.org/10.1007/s10600-010-9490-z