Antimicrobial Activity of 6-Oxophenolic Triterpenoids. Mode of Action against<i>Bacillus subtilis</i>

Leon, L.; Beltrán, Beatriz; Moujir, Laila

doi:10.1055/s-2005-864096

Cited by 43 publications

(39 citation statements)

References 14 publications

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“…2003) effects. Furthermore, in a previous work, we demonstrated the antimicrobial action of zeylasteral and demethylzeylasteral (de León et al. 2005).…”

Section: Introductionmentioning

confidence: 74%

Activity and mechanism of the action of zeylasterone against Bacillus subtilis

Leon

Moujir

2008

J Appl Microbiol

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Aims: To investigate the antimicrobial properties of 6‐oxophenolic triterpenoids isolated from Maytenus blepharodes against different micro‐organisms and the mode of action on Bacillus subtilis. Methods and Results: The activity of zeylasterone and demethylzeylasterone was evaluated by microdilution method. Zeylasterone showed a higher activity, being active against Gram‐positive bacteria (minimum inhibitory concentration 3–20 μg ml−1) and Candida albicans (10 μg ml−1). Killing curves revealed a bacteriostatic effect on B. subtilis that was dependent on the growth phase and inoculum size. Zeylasterone caused cell membrane alterations in B. subtilis, as shown by potassium leakage and formation of mesosome‐like structures. However, membrane disruption was not revealed by either LIVE/DEAD Baclight assay or measurement of intracellular constituent efflux. Zeylasterone showed an early effect on N‐acetyl‐glucosamine and uridine incorporation and later on that of thymidine and leucine. Conclusions: Diverse micro‐organisms exhibit sensitivities towards compounds studied. The permeability changes in the cytoplasmic membrane and nonsimultaneous ceasing of macromolecular synthesis suggest that zeylasterone could act on multiple targets on B. subtilis. Significance and Impact of the Study: The activity showed against B. subtilis as a model of spore‐forming bacteria would provide valuable information for further studies in the development of 6‐oxophenolic triterpenoids as antiseptic and disinfectant properties.

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“…2003) effects. Furthermore, in a previous work, we demonstrated the antimicrobial action of zeylasteral and demethylzeylasteral (de León et al. 2005).…”

Section: Introductionmentioning

confidence: 74%

Activity and mechanism of the action of zeylasterone against Bacillus subtilis

Leon

Moujir

2008

J Appl Microbiol

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“…It has been postulated that zeylasteral and demethylzeylasteral, triterpenoids which exhibited antimicrobial activity against Gram-positive bacteria, block cell division by inhibiting DNA synthesis and macromolecular synthesis in Bacillus subtilis . The inhibition of macromolecular synthesis could be due to the damage to the cell membrane [6]. …”

Section: Resultsmentioning

confidence: 99%

Synergistic antimicrobial activity between pentacyclic triterpenoids and antibiotics against Staphylococcus aureus strains

Chung

Parasakthi

Chung

2011

Ann Clin Microbiol Antimicrob

148

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BackgroundThere has been considerable effort to discover plant-derived antibacterials against methicillin-resistant strains of Staphylococcus aureus (MRSA) which have developed resistance to most existing antibiotics, including the last line of defence, vancomycin. Pentacyclic triterpenoid, a biologically diverse plant-derived natural product, has been reported to show anti-staphylococcal activities. The objective of this study is to evaluate the interaction between three pentacyclic triterpenoid and standard antibiotics (methicillin and vancomycin) against reference strains of Staphylococcus aureus.Methods and ResultsThe activity of the standard antibiotics and compounds on reference methicillin-sensitive and resistant strains of S. aureus were determined using the macrodilution broth method. The minimum inhibitory concentration (MIC) of the compounds was compared with that of the standard antibiotics. The interaction between any two antimicrobial agents was estimated by calculating the fractional inhibitory concentration (FIC index) of the combination. The various combinations of antibiotics and compounds reduced the MIC to a range of 0.05 to 50%.ConclusionPentacyclic triterpenoids have shown anti-staphylococcal activities and although individually weaker than common antibiotics produced from bacteria and fungi, synergistically these compounds may use different mechanism of action or pathways to exert their antimicrobial effects, as implicated in the lowered MICs. Therefore, the use of current antibiotics could be maintained in their combination with plant-derived antibacterial agents as a therapeutic option in the treatment of S. aureus infections.

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“…Treating B. subtilis with a series of 6-oxophenolic triterpenoids (zeylasteral, demethylzeylasteral and zeylasterone) isolated from Maytenus blepharodes Lundell resulted in abnormally long cells (De León et al, 2005;De León and Moujir, 2008) and multiseptate filaments (De León et al, 2005). The compounds were found to damage the cytoplasmic membrane and compromise cell wall synthesis, leading to loss of cytoplasmic material.…”

Section: Discussionmentioning

confidence: 99%

“…Previously, several antibacterial compounds from natural products had been reported to cause cell elongation or filamentation in B. subtilis (Beuria et al, 2005;De León et al, 2005;Jaiswal et al, 2007;De León and Moujir, 2008). Treating B. subtilis with a series of 6-oxophenolic triterpenoids (zeylasteral, demethylzeylasteral and zeylasterone) isolated from Maytenus blepharodes Lundell resulted in abnormally long cells (De León et al, 2005;De León and Moujir, 2008) and multiseptate filaments (De León et al, 2005).…”

Section: Discussionmentioning

confidence: 99%

Effect of the derivatives of andrographolide on the morphology of Bacillus subtilis

et al. 2011

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Andrographis paniculata has been reported to have antiviral, antipyretic and anticancer activities. Andrographolide, an ent-labdane diterpene, is an active constituent in this plant. In this study, andrographolide (1) and its natural derivative 14-deoxy-11,12-didehydroandrographolide (2) and 5 other semisynthetic derivatives were tested for their activity against Gram-positive and Gram-negative bacteria and Candida albicans. Only derivatives bearing a 14-acetyl group showed activity, and this activity was only against Gram-positive bacteria. 14-Acetylandrographolide showed the highest potency against Bacillus subtilis; the other 14-acetylandrographolides with additional substitution at the 3- and 19-hydroxyl groups showed lower activity against Gram-positive bacteria. The morphology of B. subtilis after being treated with 14-acetylandrographolide was investigated with TEM. This is the first report on 14-acetylandrographolide's quantified antibacterial activity, and the crucial functional group of this ent-labdane that plays an important role in perturbing the morphogenesis of B. subtilis leading to cell death.

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Antimicrobial Activity of 6-Oxophenolic Triterpenoids. Mode of Action againstBacillus subtilis

Cited by 43 publications

References 14 publications

Activity and mechanism of the action of zeylasterone against Bacillus subtilis

Activity and mechanism of the action of zeylasterone against Bacillus subtilis

Synergistic antimicrobial activity between pentacyclic triterpenoids and antibiotics against Staphylococcus aureus strains

Effect of the derivatives of andrographolide on the morphology of Bacillus subtilis

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