Antimicrobial Activity of Catechol and Pyrogallol as Allelochemicals

Kocaçalışkan, İsmail; Talan, Ismet; Terzi, İrfan

doi:10.1515/znc-2006-9-1004

Cited by 119 publications

(80 citation statements)

References 9 publications

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“…In the extract and fractions, the presence of pyrogallol and coniferyl acid is observed (Table 1). These compounds are probably responsible for the antibacterial activity, as the data are consistent with Kocacaliskan et al, (2006), who tested the antibacterial activity of pyrogallol against three bacteria (Pseudomonas putida, Pseudomonas pyocyanea, Corynebacterium xerosis) and found significant antibacterial activity. Pyrogallol showed activity against bacteria and fungi through inhibiting the function of the plasma membrane, altering its permeability, and is a good antioxidant (Muñoz et al, 2004).…”

Section: Discussionsupporting

confidence: 82%

Biological Properties and Chemical Composition of Jatropha Neopauciflora Pax

Hernández-Hernández¹,

Alarcón-Aguilar²,

Jiménez-Estrada³

et al. 2016

AJTCAM

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Background: Ethnopharmacological relevance. Jatropha neopauciflora (Pax) is an endemic species of the TehuacanCuicatlan Valley, Mexico. This species has long been used as a remedy to alleviate illnesses of bacterial, fungal and viral origin. Aim of the study. Experimentally test the traditional use of Jatropha neopauciflora in Mexican traditional medicine. Materials and methods. The methanol extract (MeOH1), of Jatropha neopauciflora (Euphorbiaceae) was obtained by maceration. Next, the methanol (MeOH2) and hexane (H) fractions were obtained. The essential oil was obtained by hydrodistillation. The extract, fractions and essential oil were analyzed by GC-MS. The antimicrobial activity was measured by the disc diffusion agar and radial inhibition growth methods. Results: The extract and fractions showed antibacterial activity against eleven strains (five Gram-positive and six Gramnegative) and a bacteriostatic effect in the survival curves for Staphylococcus aureus and Vibrio cholerae. The extract and fractions were also shown to have antifungal activity, particularly against Trichophyton mentagrophytes (CF 50 = MeOH1: 1.07 mg/mL, MeOH2: 1.32 mg/mL and H: 1.08 mg/mL). The antioxidant activity of MeOH1 (68.6 g/mL) was higher than for MeOH2 (108.1 g/mL). The main compounds of the essential oil were -pinene, 1,3,8-p-menthatriene, ledene, mmenthane, linalyl acetate and 3-carene. The main compounds of MeOH1 were β-sitosterol, lupeol and pyrogallol; the main compounds of MeOH2 were β-sitosterol, spathulenol, coniferyl alcohol and lupeol; and the main compounds of H were β-sitostenone, -sitosterol and stigmasterol. Conclusions: This study indicates that Jatropha neopauciflora is a potential antibacterial and antifungal agent.

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Section: Discussionsupporting

confidence: 82%

Biological Properties and Chemical Composition of Jatropha Neopauciflora Pax

Hernández-Hernández¹,

Alarcón-Aguilar²,

Jiménez-Estrada³

et al. 2016

AJTCAM

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“…S6 in the supplemental material), which are relatively resistant to adverse environments (43), and hence, the promotion of conidiation in response to compounds like catechol likely facilitates the survival of PS1-7. There seems to be a link between the metabolic and morphological responses, as shown by autoregulatory signals acting in concert with environmental cues in regulating a series of morphological events in filamentous fungi (21,44). The discovery of this chemical stress response sheds light on the link between carot-4-en-9,10-diol production and conidiation (Fig.…”

Section: Discussionmentioning

confidence: 99%

“…Potent resistance to tropolone, which is cytotoxic due to its iron-chelating properties, was set as the screening criterion for identification of candidate biocontrol agents for rice seedling blight. To screen for iron chelator-resistant microorganisms, we employed a simple analog of tropolone, catechol, which has relatively low cytotoxicity for bacteria and fungi (19)(20)(21). Catechol (Tokyo Chemical Industry, Tokyo, Japan) was added as a supplement to PDA at 0.2, 1, 5, 10, 15, and 20 mM.…”

Section: Methodsmentioning

confidence: 99%

Carot-4-en-9,10-Diol, a Conidiation-Inducing Sesquiterpene Diol Produced by Trichoderma virens PS1-7 upon Exposure to Chemical Stress from Highly Active Iron Chelators

Wang

Hashimoto

Hashidoko

2013

Appl Environ Microbiol

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To screen biocontrol agents against Burkholderia plantarii, the causative agent of rice seedling blight, we employed catechol, an analog of the virulence factor tropolone, to obtain chemical stress-resistant microorganisms. The fungal isolate PS1-7, identified as a strain of Trichoderma virens, showed the highest resistance to catechol (20 mM) and exhibited efficacy as a biocontrol agent for rice seedling blight. During investigation of metabolic traits of T. virens PS1-7 exposed to catechol, we found a secondary metabolite that was released extracellularly and uniquely accumulated in the culture. The compound induced by chemical stress due to catechol was subsequently isolated and identified as a sesquiterpene diol, carot-4-en-9,10-diol, based on spectroscopic analyses. T. virens PS1-7 produced carot-4-en-9,10-diol as a metabolic response to tropolone at concentrations from 0.05 to 0.2 mM, and the response was enhanced in a dose-dependent manner, similar to its response to catechol at concentrations from 0.1 to 1 mM. Some iron chelators, such as pyrogallol, gallic acid, salicylic acid, and citric acid, at 0.5 mM also showed activation of T. virens PS1-7 production of carot-4-en-9,10-diol. This sesquiterpene diol, formed in response to chemical stress, promoted conidiation of T. virens PS1-7, suggesting that it is involved in an autoregulatory signaling system. In a bioassay of the metabolic and morphological responses of T. virens PS1-7, conidiation in hyphae grown on potato dextrose agar (PDA) plates was either promoted or induced by carot-4-en-9,10-diol. Carot-4-en-9,10-diol can thus be regarded as an autoregulatory signal in T. virens, and our findings demonstrate that intrinsic intracellular signaling regulates conidiation of T. virens.

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“…Catechol and pyrogallol are allelo chemicals which belong to phenolic compounds synthesized in plants 18 . Both of these two compounds are reported to be associated with antibacterial 19,20 and anticancer 21,22 properties.…”

Section: Short Communicationmentioning

confidence: 99%

“…The compounds selected for the antimicrobial screening contain catechol and pyrogallol structural units in their structures. The rationale for this choice is the fact that catechol and pyrogallol are allelo chemicals belonging to phenolic compounds synthesized in plants 18 , and significant antibacterial activity is associated with them 19,20 . In the present study, it has been noticed that presence of nitro groups in phthalides considerably decrease the antifungal and antibacterial activity.…”

Section: Biological Activitymentioning

confidence: 99%