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Biological activities of extracts from Chenopodium ambrosioides Lineu and Kielmeyera neglecta Saddi.

Sousa ZL, de Oliveira FF, da Conceição AO, Silva LA, Rossi MH, Santos Jda S, Andrioli JL - Ann. Clin. Microbiol. Antimicrob. (2012)

Bottom Line: Extracts from C. ambrosioides (Hex, DCM and EtOH) and K. neglecta (EtOAc and EtOH) showed high bioactivity against A. salina (LD50 < 1000 μg/mL), which might be associated with cytotoxic activity against cancer cells.C. ambrosioides Hex and DCM showed specific activity against yeasts, highlighting the activity of hexanic extract against Candida krusei (MIC = 100 μg/mL).Generally speaking, extracts from C. ambrosioides and K. neglecta showed biological activities that have made the search for bioactive substances in these plants more attractive, illustrating the success of their use in the Brazilian folk medicine.

View Article: PubMed Central - HTML - PubMed

Affiliation: Programa de Pós-graduação em Biologia e Biotecnologia de Microrganismos, Universidade Estadual de Santa Cruz, Campus Prof, Soane Nazaré de Andrade, Km 16 - Rodovia Ilhéus/Itabuna, 45662-900, Ilhéus, Brazil.

ABSTRACT

Background: Chenopodium ambrosioides and Kielmeyera neglecta are plants traditionally used in Brazil to treat various infectious diseases. The study of the biological activities of these plants is of great importance for the detection of biologically active compounds.

Methods: Extracts from these plants were extracted with hexane (Hex), dichloromethane (DCM), ethyl acetate (EtOAc) and ethanol (EtOH) and assessed for their antimicrobial properties, bioactivity against Artemia salina Leach and antifungal action on the cell wall of Neurospora crassa.

Results: Extracts from C. ambrosioides (Hex, DCM and EtOH) and K. neglecta (EtOAc and EtOH) showed high bioactivity against A. salina (LD50 < 1000 μg/mL), which might be associated with cytotoxic activity against cancer cells. C. ambrosioides Hex and DCM showed specific activity against yeasts, highlighting the activity of hexanic extract against Candida krusei (MIC = 100 μg/mL). By comparing the inhibitory concentration of 50% growth (IC 50%) with the growth control, extracts from K. neglecta EtOAc and EtOH have shown activities against multidrug-resistant bacteria (Enterococcus faecalis ATCC 51299 and Staphylococcus aureus ATCC 43300), with IC 50% of 12.5 μg/mL The assay carried out on N. crassa allowed defining that extracts with antifungal activity do not have action through inhibition of cell wall synthesis.

Conclusions: Generally speaking, extracts from C. ambrosioides and K. neglecta showed biological activities that have made the search for bioactive substances in these plants more attractive, illustrating the success of their use in the Brazilian folk medicine.

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Related in: MedlinePlus

Chemical structures identified from K. neglecta: friedelan-3-one (A), friedelan-3-β-ol (B), β-sitosterol (C), stigmasterol (D), 1,8-dihydroxy-6,6-dimethylpyrano(2,3;5,6)-4′,4′,5′-trimethyldihydrofuran(2′,3′;2,3)xanthone (E), 1,7-dihydroxyxanthone (F). With permission of the author. (Oliveira, unpublished results).
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Figure 2: Chemical structures identified from K. neglecta: friedelan-3-one (A), friedelan-3-β-ol (B), β-sitosterol (C), stigmasterol (D), 1,8-dihydroxy-6,6-dimethylpyrano(2,3;5,6)-4′,4′,5′-trimethyldihydrofuran(2′,3′;2,3)xanthone (E), 1,7-dihydroxyxanthone (F). With permission of the author. (Oliveira, unpublished results).

Mentions: A preliminary chemical study of extracts of roots and branches from K. neglecta resulted in the isolation of 24 substances which identification and determination of structures by spectrometric methods (UV, IR, ¹H NMR, ¹³C NMR, NOESY) and comparison with data from the literature were done. Isolated substances were the triterpenes friedelan-3-one (friedelin) (Figure 2A) and friedelan-3-β-ol (friedelinol) (Figure 2B); the steroids β-sitosterol (Figure 2C) and stigmasterol (Figure 2D); and the xanthones 1,8-dihydroxy-6,6-dimethylpyrano(2,3;5,6)-4′,4′,5′-trimethyldihydrofuran(2′,3′;2,3)xanthone (Figure 2E) and 1,7-dihydroxyxanthone (Figure 2F) [43]. The analysis of biological activities with the isolated compounds was not performed, but it might be possible that the xanthones present in K. neglecta are synergistically responsible for the antifungal activity presented in this study, as some xanthones isolated from K. coriacea have proven to have antifungal activity against Cladosporium cucumerinum and C. albicans, whereof some have shown a fungicidal effect against the latter [44]. Antimicrobial activity against Candida species can also be explained by the compound friedelin, which has been shown to have activity against C. albicans, C. krusei and C. glabrata[45]. In addition, friedelin has shown to have microbicidal activity against E. faecalis[45] and S. aureus[46], whereas friedelinol has shown to have microbicidal activity against S. aureus[46].


Biological activities of extracts from Chenopodium ambrosioides Lineu and Kielmeyera neglecta Saddi.

Sousa ZL, de Oliveira FF, da Conceição AO, Silva LA, Rossi MH, Santos Jda S, Andrioli JL - Ann. Clin. Microbiol. Antimicrob. (2012)

Chemical structures identified from K. neglecta: friedelan-3-one (A), friedelan-3-β-ol (B), β-sitosterol (C), stigmasterol (D), 1,8-dihydroxy-6,6-dimethylpyrano(2,3;5,6)-4′,4′,5′-trimethyldihydrofuran(2′,3′;2,3)xanthone (E), 1,7-dihydroxyxanthone (F). With permission of the author. (Oliveira, unpublished results).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3475072&req=5

Figure 2: Chemical structures identified from K. neglecta: friedelan-3-one (A), friedelan-3-β-ol (B), β-sitosterol (C), stigmasterol (D), 1,8-dihydroxy-6,6-dimethylpyrano(2,3;5,6)-4′,4′,5′-trimethyldihydrofuran(2′,3′;2,3)xanthone (E), 1,7-dihydroxyxanthone (F). With permission of the author. (Oliveira, unpublished results).
Mentions: A preliminary chemical study of extracts of roots and branches from K. neglecta resulted in the isolation of 24 substances which identification and determination of structures by spectrometric methods (UV, IR, ¹H NMR, ¹³C NMR, NOESY) and comparison with data from the literature were done. Isolated substances were the triterpenes friedelan-3-one (friedelin) (Figure 2A) and friedelan-3-β-ol (friedelinol) (Figure 2B); the steroids β-sitosterol (Figure 2C) and stigmasterol (Figure 2D); and the xanthones 1,8-dihydroxy-6,6-dimethylpyrano(2,3;5,6)-4′,4′,5′-trimethyldihydrofuran(2′,3′;2,3)xanthone (Figure 2E) and 1,7-dihydroxyxanthone (Figure 2F) [43]. The analysis of biological activities with the isolated compounds was not performed, but it might be possible that the xanthones present in K. neglecta are synergistically responsible for the antifungal activity presented in this study, as some xanthones isolated from K. coriacea have proven to have antifungal activity against Cladosporium cucumerinum and C. albicans, whereof some have shown a fungicidal effect against the latter [44]. Antimicrobial activity against Candida species can also be explained by the compound friedelin, which has been shown to have activity against C. albicans, C. krusei and C. glabrata[45]. In addition, friedelin has shown to have microbicidal activity against E. faecalis[45] and S. aureus[46], whereas friedelinol has shown to have microbicidal activity against S. aureus[46].

Bottom Line: Extracts from C. ambrosioides (Hex, DCM and EtOH) and K. neglecta (EtOAc and EtOH) showed high bioactivity against A. salina (LD50 < 1000 μg/mL), which might be associated with cytotoxic activity against cancer cells.C. ambrosioides Hex and DCM showed specific activity against yeasts, highlighting the activity of hexanic extract against Candida krusei (MIC = 100 μg/mL).Generally speaking, extracts from C. ambrosioides and K. neglecta showed biological activities that have made the search for bioactive substances in these plants more attractive, illustrating the success of their use in the Brazilian folk medicine.

View Article: PubMed Central - HTML - PubMed

Affiliation: Programa de Pós-graduação em Biologia e Biotecnologia de Microrganismos, Universidade Estadual de Santa Cruz, Campus Prof, Soane Nazaré de Andrade, Km 16 - Rodovia Ilhéus/Itabuna, 45662-900, Ilhéus, Brazil.

ABSTRACT

Background: Chenopodium ambrosioides and Kielmeyera neglecta are plants traditionally used in Brazil to treat various infectious diseases. The study of the biological activities of these plants is of great importance for the detection of biologically active compounds.

Methods: Extracts from these plants were extracted with hexane (Hex), dichloromethane (DCM), ethyl acetate (EtOAc) and ethanol (EtOH) and assessed for their antimicrobial properties, bioactivity against Artemia salina Leach and antifungal action on the cell wall of Neurospora crassa.

Results: Extracts from C. ambrosioides (Hex, DCM and EtOH) and K. neglecta (EtOAc and EtOH) showed high bioactivity against A. salina (LD50 < 1000 μg/mL), which might be associated with cytotoxic activity against cancer cells. C. ambrosioides Hex and DCM showed specific activity against yeasts, highlighting the activity of hexanic extract against Candida krusei (MIC = 100 μg/mL). By comparing the inhibitory concentration of 50% growth (IC 50%) with the growth control, extracts from K. neglecta EtOAc and EtOH have shown activities against multidrug-resistant bacteria (Enterococcus faecalis ATCC 51299 and Staphylococcus aureus ATCC 43300), with IC 50% of 12.5 μg/mL The assay carried out on N. crassa allowed defining that extracts with antifungal activity do not have action through inhibition of cell wall synthesis.

Conclusions: Generally speaking, extracts from C. ambrosioides and K. neglecta showed biological activities that have made the search for bioactive substances in these plants more attractive, illustrating the success of their use in the Brazilian folk medicine.

Show MeSH
Related in: MedlinePlus