A new cytotoxic naphthopyrone dimer from Paepalanthus bromelioides

Coelho, Roberta Gomes; Vilegas, Wagner; Devienne, Karina F.; Raddi, Maria Stella Gonçalves

doi:10.1016/s0367-326x(00)00159-3

Cited by 25 publications

(20 citation statements)

References 6 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.…”

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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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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“…Planifoline, a dimer with an ethereal bond between two OH groups at position 9, was isolated from Paepalanthus planifolius, 12) whereas a dimer linked through a C-C bond was isolated from P. bromelioides. 13) Chemical constituents have previously proved to be an important taxonomic character in Eriocaulaceae. Naphthopyranones and flavonols are the major compounds of many Paepalanthus species.…”

Section: Resultsmentioning

confidence: 99%

“…General Experimental Procedure Structural identification of the compounds using NMR spectra in DMSO-d 6 (compounds 1-4) were obtained using a Varian INOVA 500 operating at 500 MHz for 1 H-NMR and 125 MHz for 13 C-NMR using 1-D and 2-D experiments (inverse detection 1 H-13 C HSQC and HMBC). For compounds 1-4, samples were dissolved in methanol and injected directly into the mass spectrometer through a Rheodyne injector.…”

Section: Methodsmentioning

confidence: 99%

Flavonoids and a Naphthopyranone from Eriocaulon ligulatum and Their Mutagenic Activity

et al. 2007

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“…5) In previous works we have described some biological activity (cytotoxicity, antimicrobial and antioxidant) from naphthopyrones isolated from the capitula of P. bromelioides. [6][7][8] In this work we describe the isolation, structure determination and the cytotoxic effect in vitro of a new 1,4-naphthoquinone isolated from the capitula of Paepalanthus latipes. …”

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A New Cytotoxic Naphthoquinone from Paepalanthus latipes.

et al. 2005

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Quinones are widely distributed in nature and constitute an important class of naturally occurring compounds. They are found in plants, fungi and bacteria. 1) These compounds are aromatic rings with two ketone substitutions. 2) Large number of quinones has been associated with antitumor, antibacterial, antimalarial and antifungal activities.3) The antitumor activity is exhibited predominantly by three main groups of naturally occurring quinones such as benzoquinone, naphthoquinone and anthraquinone. Mitomycin and streptonigrin possess p-benzoquinone moiety with heterocyclic groups whereas anthracyclines, doxorubicin and daunorubicin consist of anthraquinone moiety. Some naphthaquinone antibiotics such as lapachol and lapinone are also found to be cytotoxic to tumor cells. 4) Plants of the Eriocaulaceae family are widespread in the region of the Serra do Cipó, State Minas Gerais, Brazil. Several plants from this family are known as 'everlasting plants' because they appear to be alive even for years after being haversted. Paepalanthus is the largest genus of this family with approximately 500 species. Among there more than 400 species are endemic in Brazil. 5) In previous works we have described some biological activity (cytotoxicity, antimicrobial and antioxidant) from naphthopyrones isolated from the capitula of P. bromelioides. [6][7][8] In this work we describe the isolation, structure determination and the cytotoxic effect in vitro of a new 1,4-naphthoquinone isolated from the capitula of Paepalanthus latipes. Results and DiscussionCompound 1 was obtained as a red powder. The ES-MS spectrum of 1 (positive mode) exhibited protonated molecular ion [MϩH] ] ϩ were also observed. The IR spectrum showed absorptions for hydroxyl (3300 cm Ϫ1 ) and carbonyl groups (1680, 1620 cm Ϫ1 ) indicating a para-quinone system. 9,10) The complete structure of 1 was elucidated by 1D and 2D NMR experiments at 500 MHz. The 13 C-NMR spectrum showed 16 signals. The 1 H-NMR spectrum displayed singlets of aromatic protons at d 6.60 (1H) and 6.05 (1H). Also evident were signals at d 3.86 and 3.81 typical of aromatic methoxyl groups. Another signal at d 2.28 (3H) corresponds to a methyl group. Assignments of 1 H-and 13 C-NMR data were based on HMBC and HSQC experiments (Table 1). In the HMBC spectrum we observed diagnostic long-range correlations between the proton signal at d 6.60 (H-4) and the carbon resonances at d 167.0 (C-1), 161.4 (C-10), 113.0 (C-10a), 148.0 (C-5) and 20.3 (C-11); the proton at d 6.08 (H-8) and the carbonyl carbon resonances at d 177.9 (C-6) and at d 189.2 (C-9) and the carbon resonances at 160.9 (C-7) and 111.2 (C-9a); the proton at d 3.86 (OCH 3 -7) and the carbon resonance at d 160.9 (C-7); the proton signal at d 3.81 (OCH 3 -5) and the carbon resonance at d 147.9 (C-5); the methyl group at d 2.28 (CH 3 -11) and the carbon signals at d 160.7 (C-3) and d 98.2 (C-4). NOESY experiment displayed correlations between the signal at d 6.60 (H-4) and the signals at d 2.28 (CH 3 -11) and at d 3.81 (OCH 3 -5), and betw...

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A new cytotoxic naphthopyrone dimer from Paepalanthus bromelioides

Cited by 25 publications

References 6 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

Flavonoids and a Naphthopyranone from Eriocaulon ligulatum and Their Mutagenic Activity

A New Cytotoxic Naphthoquinone from Paepalanthus latipes.

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