title: Antioxidant activity of zyzzyanones and makaluvamines from the marine sponge Zyzzya fuliginosa.
abstract: Antioxidant activities of zyzzyanones A-D (1-4) and makaluvamines C (8), E (5), G (6), H (9), and L (7) isolated from the marine sponge Zyzzya fuliginosa (Carter, 1879) were evaluated using 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) (ABTS) scavenging assay and AAPH (2,2'-azobis(2-amidinopropane) dihydrochloride) induced autoxidation of linoleic acid. Zyzzyanones A, B (1, 2; TE = 0.3), C, D (3, 4; TE = 0.24) and makaluvamines 5-7 (TE = 0.6) displayed moderate activities in the ABTS assay and in the autoxidation of linoleic acid (61-66% inhibition at concentrations of 0.1 mM). Makaluvamines C (8) and H (9) were essentially inactive in the both assays. Structure-activity relationships showed that antioxidant activities of tested compounds depended on the presence of a phenolic function in molecules. Makaluvamines 5-7 possessing a p-hydroxystyryl moiety were more active than zyzzyanones 1-4 possessing a p-hydroxyphenyl fragment. The presence of a charged side chain in 1 and 2 slightly increases their ABTS scavenging activity in comparison with compounds 3 and 4. Structural variations in a pyrroloquinoline skeleton of 5-7 and in a dipyrroloquinone core of 1-4 have no effect on activities.
authors.affiliation: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect Stoletia Vladivostoka 159, Vladivostok 690022, Russian Federation. utkinan@mail.ru
authors.forename: Natalia K
authors.initials: NK
authors.lastname: Utkina
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000494:pharmacology; D011161:Porifera / Q000737:chemistry*; D011758:Pyrroles / Q000494:pharmacology*; D015363:Quinolones / Q000494:pharmacology; D011809:Quinones / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000975:Antioxidants; D016166:Free Radical Scavengers; D011758:Pyrroles; D015363:Quinolones; D011809:Quinones; C119051:makaluvamine H; C505320:zyzzyanone B; C505321:zyzzyanone C; C505322:zyzzyanone D