title: Mutagenicity of paepalantine dimer and glycoside derivatives from Paepalanthus bromelioides.
abstract: 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.
authors: Department of Biological Sciences, Faculty of Pharmaceutical Sciences of Araraquara, Estadual Paulist University,UNESP- Rodovia Araraquara-Jaú Km 1, 14801-902, SP, Brazil. varandae@fcfar.unesp.br
authors: E A
authors: EA
authors: Varanda
authors: K F
authors: KF
authors: Devienne
authors: M S G
authors: MS
authors: Raddi
authors: E M
authors: EM
authors: Furuya
authors: W
authors: W
authors: Vilegas
mesh_terms: D000818:Animals; D003374:Coumarins / Q000009:adverse effects* / Q000737:chemistry / Q000302:isolation & purification; D006224:Cricetinae; D019281:Dimerization; D004305:Dose-Response Relationship, Drug; D004353:Drug Evaluation, Preclinical; D039262:Eriocaulaceae; D006027:Glycosides / Q000009:adverse effects* / Q000737:chemistry / Q000302:isolation & purification; D049934:Isocoumarins; D008752:Methylene Chloride / Q000737:chemistry; D009152:Mutagenicity Tests; D009153:Mutagens / Q000009:adverse effects / Q000737:chemistry / Q000302:isolation & purification*; D010936:Plant Extracts / Q000009:adverse effects / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry; D012486:Salmonella typhimurium / Q000187:drug effects / Q000235:genetics; D013045:Species Specificity; D008941:Spindle Apparatus / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D003374:Coumarins; D006027:Glycosides; D049934:Isocoumarins; D009153:Mutagens; D010936:Plant Extracts; C493827:isocoumarin 2; C493826:isocoumarin 3; C108025:paepalantine; D008752:Methylene Chloride