Mutagenicity of paepalantine dimer and glycoside derivatives from Paepalanthus bromelioides

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Varanda, Eliana Aparecida [UNESP]
Devienne, K. F.
Raddi, MSG
Furuya, E. M.
Vilegas, Wagner [UNESP]

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Elsevier B.V.


The first isocoumarin isolated from the methylene chloride extract of Paepalanthus bromelioides, named paepalantine (isocoumarin 1), was found to have antimicrobial activity; but, it is mutagenic clastogenic and cytotoxic. Two other isocoumarins, paepalantine-9-O-beta-D-glucopyranoside (isocoumarin 2) and paepalantine-9-O-beta-D-allopyranosyl(1-->6) glucopyranoside (isocoumarin 3) were isolated from the ethanolic extract. A fourth new isocoumarin, also isolated from the methylene chloride extract of the capitula of P. bromelioides, was characterized as an 8-8' dimer of paepalantine and denominated isocoumarin 4. The abilities of isocoumarins 2, 3 and 4 to induce mutations in Salmonella typhimurium strains TA97a, TA98, TA100 and TA102 were investigated. Mutagenic activity was observed in strain TA97a treated with isocoumarin 2 in the presence of S9 mixture. The substitution of H at position 9 by glucose or glucose-allose caused reductions in the mutagenic activities of paepalantine, indicating this to be an important site for these properties. (C) 2003 Elsevier Ltd. All rights reserved.



isocoumarins, mutagenicity, Salmonella typhimurium

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Toxicology In Vitro. Oxford: Pergamon-Elsevier B.V., v. 18, n. 1, p. 109-114, 2004.