Metabolism of the tomato saponin α-tomatine by phytopathogenic fungi

Ruiz-Rubio, Manuel; Pérez-Espinosa, Alonso; Lairini, Khalid; Roldán-Arjona, Teresa; Dipietro, Antonio; Anaya, Nuria

doi:10.1016/s1572-5995(01)80010-7

Cited by 15 publications

(8 citation statements)

References 99 publications

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“…It has also been shown that adding sugars (glucose and sucrose) stimulated the spore germination and mycelial growth of F. oxysporum in a concentration dependent pattern (Wang, Wu, & Han, 2007). Moreover, microorganisms have the ability to change their metabolic processes and generate molecules that contribute to stress adaptation such as degradation and detoxifying enzymes (Ruiz-Rubio et al, 2001). IC 50 and IC 100 values of inclusion complexes for F. oxysporum and B. cinerea were illustrated in Fig.…”

Section: Mycelium Growth Assaymentioning

confidence: 99%

Solubility, photostability and antifungal activity of phenylpropanoids encapsulated in cyclodextrins

et al. 2016

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Section: Mycelium Growth Assaymentioning

confidence: 99%

Solubility, photostability and antifungal activity of phenylpropanoids encapsulated in cyclodextrins

et al. 2016

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“…Tomatidine (TO) is a steroidal alkaloid produced by the Solanaceae plant family such as the tomato [ 17 , 18 ]. We showed previously the antibacterial activity of TO against S. aureus SCVs and also documented a strong synergic activity of TO in combination with aminoglycoside antibiotics against prototypic S. aureus [ 19 , 20 ].…”

Section: Introductionmentioning

confidence: 99%

Tomatidine and analog FC04–100 possess bactericidal activities against Listeria, Bacillus and Staphylococcus spp

Guay

Boulanger

Isabelle

et al. 2018

BMC Pharmacol Toxicol

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BackgroundTomatidine (TO) is a plant steroidal alkaloid that possesses an antibacterial activity against the small colony variants (SCVs) of Staphylococcus aureus. We report here the spectrum of activity of TO against other species of the Bacillales and the improved antibacterial activity of a chemically-modified TO derivative (FC04–100) against Listeria monocytogenes and antibiotic multi-resistant S. aureus (MRSA), two notoriously difficult-to-kill microorganisms.MethodsBacillus and Listeria SCVs were isolated using a gentamicin selection pressure. Minimal inhibitory concentrations (MICs) of TO and FC04–100 were determined by a broth microdilution technique. The bactericidal activity of TO and FC04–100 used alone or in combination with an aminoglycoside against planktonic bacteria was determined in broth or against bacteria embedded in pre-formed biofilms by using the Calgary Biofilm Device. Killing of intracellular SCVs was determined in a model with polarized pulmonary cells.ResultsTO showed a bactericidal activity against SCVs of Staphylococcus aureus, Bacillus cereus, B. subtilis and Listeria monocytogenes with MICs of 0.03–0.12 μg/mL. The combination of an aminoglycoside and TO generated an antibacterial synergy against their normal phenotype. In contrast to TO, which has no relevant activity by itself against Bacillales of the normal phenotype (MIC > 64 μg/mL), the TO analog FC04–100 showed a MIC of 8–32 μg/mL. Furthermore, FC04–100 showed a strong bactericidal activity against L. monocytogenes SCVs in kill kinetics experiments, while TO did not. The addition of FC04–100 (4 μg/mL) to a cefalexin:kanamycin (3:2) combination improved the activity of the combination by 32 fold against cefalexin and kanamycin-resistant MRSA strains. In combination with gentamicin, FC04–100 also exhibited a strong bactericidal activity against biofilm-embedded S. aureus. Also, FC04–100 and TO showed comparable intracellular killing of S. aureus SCVs.ConclusionsChemical modifications of TO allowed improvement of its antibacterial activity against prototypical S. aureus and of its bactericidal activity against L. monocytogenes. Antibacterial activities against such prominent pathogens could be useful to prevent Listeria contamination in the food chain or as treatment for MRSA infections.

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“…Many tomato fungal pathogens produce extracellular enzymes, commonly referred to as tomatinases, that are able to detoxify the ␣-tomatine (23,35,36). As an example, Fusarium oxysporum f. sp.…”

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confidence: 99%

“…As an example, Fusarium oxysporum f. sp. lycopersici was reported to cleave ␣-tomatine into its aglycon (tomatidine) and tetrasaccharide moieties (lycotetraose), the by-products of which have little to no antifungal activity against the pathogen (36,41). Some of our recent work on bacteria exposed to plant products shed light on the bioactivity of tomatidine against S. aureus and suggested a possible application for this molecule as a virulence attenuator for typical S. aureus strains (6) and, more recently, for SCVs (28).…”

mentioning

confidence: 99%

Tomatidine Inhibits Replication of Staphylococcus aureus Small-Colony Variants in Cystic Fibrosis Airway Epithelial Cells

Mitchell

Gattuso

Grondin

et al. 2011

Antimicrob Agents Chemother

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Small-colony variants (SCVs) often are associated with chronic Staphylococcus aureus infections, such as those encountered by cystic fibrosis (CF) patients. We report here that tomatidine, the aglycon form of the plant secondary metabolite tomatine, has a potent growth inhibitory activity against SCVs (MIC of 0.12 g/ml), whereas the growth of normal S. aureus strains was not significantly altered by tomatidine (MIC, >16 g/ml). The specific action of tomatidine was bacteriostatic for SCVs and was clearly associated with their dysfunctional electron transport system, as the presence of the electron transport inhibitor 4-hydroxy-2-heptylquinoline-N-oxide (HQNO) caused normal S. aureus strains to become susceptible to tomatidine. Inversely, the complementation of SCVs' respiratory deficiency conferred resistance to tomatidine. Tomatidine provoked a general reduction of macromolecular biosynthesis but more specifically affected the incorporation of radiolabeled leucine in proteins of HQNO-treated S. aureus at a concentration corresponding to the MIC against SCVs. Furthermore, tomatidine inhibited the intracellular replication of a clinical SCV in polarized CF-like epithelial cells. Our results suggest that tomatidine eventually will find some use in combination therapy with other traditional antibiotics to eliminate persistent forms of S. aureus.

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Metabolism of the tomato saponin α-tomatine by phytopathogenic fungi

Cited by 15 publications

References 99 publications

Solubility, photostability and antifungal activity of phenylpropanoids encapsulated in cyclodextrins

Solubility, photostability and antifungal activity of phenylpropanoids encapsulated in cyclodextrins

Tomatidine and analog FC04–100 possess bactericidal activities against Listeria, Bacillus and Staphylococcus spp

Tomatidine Inhibits Replication of Staphylococcus aureus Small-Colony Variants in Cystic Fibrosis Airway Epithelial Cells

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