Mutagenicity of paepalantine dimer and glycoside derivatives from Paepalanthus bromelioides.
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.
Varanda
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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
Devienne
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Raddi
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Furuya
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Vilegas
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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
D003374:Coumarins; D006027:Glycosides; D049934:Isocoumarins; D009153:Mutagens; D010936:Plant Extracts; C493827:isocoumarin 2; C493826:isocoumarin 3; C108025:paepalantine; D008752:Methylene Chloride