Mutagenic and cytotoxic effect of planifolin: A naphthopyranone dimer isolated from Paepalanthus planifolius

Varanda, Eliana Aparecida; Varella, Soraya Duarte; Rampazo, Raquel Aparecida; Kitagawa, Rodrigo Rezende; Raddi, Maria Stella Gonçalves; Vilegas, Wagner; Santos, Lourdes Campaner dos

doi:10.1016/j.tiv.2005.09.010

Cited by 20 publications

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“…Paepalanthus, with about 500 species, is one of its principal genus. A number of studies have demonstrated that almost all species of Paepalanthus subgenus Platycaulon possess naphthopyranone derivatives, including paepalantine and 8,8 -paepalantine dimer isolated from Paepalanthus bromelioides (Vilegas et al, 1990;Coelho et al, 2000), planifolin isolated from Paepalanthus planifolius (Santos et al, 2001;Varanda et al, 2006), and 5-methoxy-3,4-dehydroxanthomegnin isolated from Paepalanthus latipes Silveira, Eriocaulaceae, (Kitagawa et al, 2004(Kitagawa et al, , 2008.…”

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confidence: 99%

Evaluation of mutagenicity and metabolism-mediated cytotoxicity of the naphthoquinone 5-methoxy-3,4-dehydroxanthomegnin from Paepalanthus latipes

Kitagawa

Vilegas

Varanda

et al. 2015

Revista Brasileira de Farmacognosia

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Please cite this article in press as: Kitagawa, R.R., et al. Evaluation of mutagenicity and metabolism-mediated cytotoxicity of the naphthoquinone 5-methoxy-3,4-dehydroxanthomegnin from Paepalanthus latipes. Revista Brasileira de Farmacognosia (2015), http://dx.BJP 83 1-6 Revista Brasileira de Farmacognosia xxx (2015) xxx-xxx w w w . s b f g n o s i a . o r g . b r / r e v i s t aOriginal Article a b s t r a c t A large number of quinones have been associated with antitumor, antibacterial, antimalarial, and antifungal activities. Results of previous studies of 5-methoxy-3,4-dehydroxanthomegnin, a naphthoquinone isolated from Paepalanthus latipes Silveira, Eriocaulaceae, revealed antitumor, antibacterial, immunomodulatory, and antioxidant activities. In this study, we assessed the mutagenicity and metabolism-mediated cytotoxicity of 5-methoxy-3,4-dehydroxanthomegnin by using the Ames test and a microculture neutral red assay incorporating an S9 fraction (hepatic microsomal fraction and cofactors), respectively. We also evaluated the mutagenic activity in Salmonella typhimurium strains TA100, TA98, TA102, and TA97a, as well as the cytotoxic effect on McCoy cells with and without metabolic activation in both tests. Results indicated that naphthoquinone does not cause mutations by substitution or by addition and deletion of bases in the deoxyribonucleic acid sequence with and without metabolic activation. As previously demonstrated, the in vitro cytotoxicity of 5-methoxy-3,4-dehydroxanthomegnin to McCoy cells showed a significant cytotoxic index (CI 50 ) of 11.9 g/mL. This index was not altered by addition of the S9 fraction, indicating that the S9 mixture failed to metabolically modify the compound. Our results, allied with more specific biological assays in the future, would contribute to the safe use of 5-methoxy-3,4-dehydroxanthomegnin, compound that has showed in previous studies beneficial properties as a potential anticancer drug.

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Section: Introductionmentioning

confidence: 99%

Evaluation of mutagenicity and metabolism-mediated cytotoxicity of the naphthoquinone 5-methoxy-3,4-dehydroxanthomegnin from Paepalanthus latipes

Kitagawa

Vilegas

Varanda

et al. 2015

Revista Brasileira de Farmacognosia

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“…The 8-8' dimer of paepalantine had been tested in concentrations that varied from 8.0 up to 128.0 Pg/plate and had shown only negative results in all tested strains (9,10).…”

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“…These dimers were isolated respectively from P. planifolius and P.bromelioides (36,37). The mutagenicity of both dimers was also determined by the Ames test and the results showed that only planifolin possesses mutagenic potencial (9,10).…”

Section: Discussionmentioning

confidence: 99%

“…vellozioides and P. planifolius, other species of Eriocaulaceae, showed positive results in the Ames test (8)(9)(10). The mutagenicity of methanol and dichloromethane extracts of E. ligulatum has also been assessed in previous work and it was observed that the methanol extract exhibited mutagenic activity in the Salmonella/microsome assay, in strains TA100, TA97a and TA102, while the dichloromethane extract was mutagenic in strain TA98 (7).…”

Section: )mentioning

confidence: 99%

“…The establishment of the structure-activity relationship of certain flavonoids and naphthopyranones, in the S. typhimurium reversion assay, has made a great contribution to the improved understanding of the possible effects and mechanisms of action of those compounds and is very useful in making comparisons between similar compounds obtained from different species of plant (8)(9)(10)(16)(17)(18)(19)(20) The aim of this report was to determine the mutagenic effect of enriched fractions and substances isolated from E. ligulatum (Vell.) L.B.…”

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Mutagenicidade e estrogenicidade de plantas da família Eriocaulaceae e relação estrutura-atividade de algumas substâncias isoladas

Oliveira¹

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Agradeço a Profª Drª ElianaÀs técnicas do laboratório de Microbiologia, Néia, Marisa e especialmente à Sílvia, pela grande ajuda no dia-a-dia, pelos ensinamentos e pelas conversas nos momentos felizes e difíceis.Às funcionárias da pós-graduação, Cláudia, Sônia, Laura e Ângela, pela ajuda, dedicação, e por sempre me receberem com simpatia. .................................................................................................................... 134 6. Conclusões .................................................................................................................. 155 7. Referências Bibliográficas ................................................................................... foi o empregado para avaliação da estrogenicidade. Os resultados da atividade mutagênica demonstraram que apenas E. ligulatum foi considerado mutagênico e isso foi atribuído às isocumarinas e flavonóides agliconas. Os estudos de relação estrutura-atividade mutagênica mostraram que esta ação foi devida à presença de hidroxilas em posições estratégicas e à ausência de glicosilações, metoxilações, ou qualquer outro tipo de substituição. Para complementar os estudos de relação estrutura-atividade mutagênica com as isocumarinas, utilizou-se resultados já publicados de mutagenicidade de moléculas semelhantes à isocumarina eriocaulina, isolada de E. ligulatum. Verificou-se que os dímeros de isocumarinas têm a sua mutagenicidade influenciada pela conformação espacial, pela presença de grupos hidroxilas mais afastados de grupos volumosos, e pelo tipo de ligação que une os seus monômeros. Quando o potencial estrogênico foi avaliado, apenas a L. flavescens apresentou resultados positivos e que esses são devidos à presença de flavonas agliconas, como a luteolina e a metoxiluteolina. As mesmas isocumarinas, pertencentes a outras espécies da família Eriocaulaceae, avaliadas no teste de Ames, foram avaliadas no teste RYA. E seus resultados foram cruciais para o estabelecimento da relação estrutura-atividade estrogênica para as isocumarinas. Verificou-se que as isocumarinas têm a estrogenicidade favorecida pela presença de adições de açúcares e por AbstractEriocaulaceae family comprises around 1200 species, divided into 10 genera, and their plant species are known as "sempre-vivas" (everlasting flowers) for its durability and color. In this work the species Eriocaulon ligulatum, Leiothrix flavescens and Leiothrix spiralis were studied. These species were evaluated for the mutagenic and the estrogenic potential and some of their isolated compounds were used for a study of structuremutagenic and estrogenic activities. To assess mutagenicity we used Ames test and the Recombinant Yeast Assay (RYA test) was used for evaluation of estrogenicity. The results of mutagenic activity showed that only E. ligulatum presented mutagenicity and that these results were due to its naphthopyranones and flavonoid aglicons. The structuremutagenic activity studies shown that this action were due to the presence of hydroxyl groups in strategic pos...

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Rhodium(III)‐Catalyzed Formal Cycloaddition between Thienopyridine/Thienopyrazine Carboxylic Acids and Alkynes, Triggered by C−H Activation

et al. 2021

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In the last decade, a number of metal-catalyzed technologies for the functionalization of CÀ H bonds in carbonaceous aromatic substrates have been developed. However, similar reactions with aza-heteroaromatic precursors are more challenging and have been much less developed. Herein, we report for the first time catalytic formal cycloadditions of N,S-heterocycles featuring carboxylic acid substituents, with unsaturated partners (alkynes). The reaction, which works with different symmetrical and unsymmetrical alkynes, produces appealing tricyclic �-pyrones in a straightforward manner. The optimized conditions established for a model reaction employing thieno [2,3-b]pyridine-2-carboxylic acid as substrate, involved the use of Ag 2 CO 3 /AgSbF 6 as additives, and proved to be general for different alkynes. Moreover, analogous cycloadditions using thieno[3,2-b]pyridine-2-carboxylic acid and thieno [2,3-b] pyrazine-6-carboxylic acid were successfully developed. Overall, this catalytic technology allows to build, in a single step, an interesting variety of pharmaceutically relevant tricyclic �pyrones exhibiting nitrogen and sulfur heteroatoms.

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Mutagenic and cytotoxic effect of planifolin: A naphthopyranone dimer isolated from Paepalanthus planifolius

Cited by 20 publications

References 18 publications

Evaluation of mutagenicity and metabolism-mediated cytotoxicity of the naphthoquinone 5-methoxy-3,4-dehydroxanthomegnin from Paepalanthus latipes

Evaluation of mutagenicity and metabolism-mediated cytotoxicity of the naphthoquinone 5-methoxy-3,4-dehydroxanthomegnin from Paepalanthus latipes

Mutagenicidade e estrogenicidade de plantas da família Eriocaulaceae e relação estrutura-atividade de algumas substâncias isoladas

Rhodium(III)‐Catalyzed Formal Cycloaddition between Thienopyridine/Thienopyrazine Carboxylic Acids and Alkynes, Triggered by C−H Activation

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