Stilbene Derivatives from <i>Photorhabdus temperata</i> SN259 and Their Antifungal Activities against Phytopathogenic Fungi

Shi, Danshu; An, Ran; Zhang, Wenbo; Zhang, Guilong; Yu, Zhiguo

doi:10.1021/acs.jafc.6b04303

Cited by 52 publications

(38 citation statements)

References 28 publications

(33 reference statements)

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“…Xenorhabdus produced xenocoumacin derivatives [37] and amicoumacin derivatives [38], were found to be potent antibiotics against S. aureus [8], while all the Photorhabdus spp. produced isopropylstilbene [39,40], which had multiple biological activities, including antibiotic activity against S. aureus and E. coli [24]. Based on the MIC and MBC, the ability to inhibit the growth of antibiotic-resistant bacteria varied on each isolate of Xenorhabdus and Photorhabdus.…”

Section: Plos Onementioning

confidence: 99%

“…These bacteria produce a broad range of secondary metabolites, including antimicrobial, insecticidal, and cytotoxic activities [8]. Antimicrobial compounds include benzaldehyde [12], 1-carbapen-2-em-3-carboxylic acid [10], 3, 5-dihydroxy-4-isopropystilbene [9], 3-hydroxy-2-isopropyl-5-phenethylphenyl carbamate [24], 2-isopropyl-5-(3-phenyl-2-oxiranyl0-benzene-1,3diol [25], and chaiyaphumine [26]. In the recent year, antibiotic-resistant bacteria are emerging with global spread leads to difficulties for the control of the disease.…”

Section: Introductionmentioning

confidence: 99%

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Antibacterial activity of Xenorhabdus and Photorhabdus isolated from entomopathogenic nematodes against antibiotic-resistant bacteria

et al. 2020

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Xenorhabdus and Photorhabdus, symbiotically associated with entomopathogenic nematodes (EPNs), produce a range of antimicrobial compounds. The objective of this study is to identify Xenorhabdus and Photorhabdus and their EPNs hosts, which were isolated from soil samples from Saraburi province, and study their antibacterial activity against 15 strains of drug-resistant bacteria. Fourteen isolates (6.1%), consisting of six Xenorhabdus isolates and eight Photorhabdus isolates, were obtained from 230 soil samples. Based on the BLASTN search incorporating the phylogenetic analysis of a partial recA gene, all six isolates of Xenorhabdus were found to be identical and closely related to X. stockiae. Five isolates of Photorhabdus were found to be identical and closely related to P. luminescens subsp. akhurstii. Two isolates of Photorhabdus were found to be identical and closely related to P. luminescens subsp. hainanensis. The remaining isolate of Photorhabdus was found to be identical to P. asymbiotica subsp. australis. The bacterial extracts from P. luminescens subsp. akhurstii showed strong inhibition the growth of S. aureus strain PB36 (MSRA) by disk diffusion, minimal inhibitory concentration, and minimal bactericidal concentration assay. The combination between each extract from Xenorhabdus/Photorhabdus and oxacillin or vancomycin against S. aureus strain PB36 (MRSA) exhibited no interaction on checkerboard assay. Moreover, killing curve assay of P. luminescens subsp. akhurstii extracts against S. aureus strain PB36 exhibited a steady reduction of 10 5 CFU/ml to 10 3 CFU/ml within 30 min. This study demonstrates that Xenorhabdus and Photorhabdus, showed antibacterial activity. This finding may be useful for further research on antibiotic production.

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Section: Plos Onementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Antibacterial activity of Xenorhabdus and Photorhabdus isolated from entomopathogenic nematodes against antibiotic-resistant bacteria

et al. 2020

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“…Some RSV natural derivatives revealed antifungal and antimicrobial activity; in Figure are depicted the structures of two natural RSV derivatives with antifungal properties, Pterostilbene and Pinosylin (Lee et al, ; López‐Nicolás, Rodríguez‐Bonilla, & García‐Carmona, ; van Baarlen et al, ). Pathogenic insects such as Photorhabdus luminescens (Bong Park & Crawford, ) or Photorhabdus temperata SN259 (Shi et al, ) biosynthesize metabolites containing SLB moiety, for example, 2‐amino‐1,4‐benzoquinone (Lumiquinone A, Figure ) and related compound 3,5‐dihydroxy‐4‐isopropyl‐ trans ‐stilbene ( 1 , Figure ). They showed reduction of the mycelial growth against phytopathogenic fungi Pythium aphanidermatum , Rhizoctonia solani Kuhn , Exserohilum turcicum , and Fusarium oxysporum and the yeast strain Saccharomyces cerevisiae using test phytopathogens measured by agar medium assay and test phytopathogens measured by microdilution broth assay, referring to Chlorothalonil as positive control (Bong Park & Crawford, ).…”

Section: Natural and Synthetic Antifungal Slb Derivativesmentioning

confidence: 99%

“…| NATURAL AND SYNTHETIC ANTIFUNGAL SLB DERIVATIVES Some RSV natural derivatives revealed antifungal and antimicrobial activity; in Figure 1 are depicted the structures of two natural RSV derivatives with antifungal properties, Pterostilbene and Pinosylin (Lee et al, 2005; López-Nicolás, Rodríguez-Bonilla, & García-Carmona, 2009; van Baarlen et al, 2004). Pathogenic insects such as Photorhabdus luminescens (BongPark & Crawford, 2015) or Photorhabdus temperata SN259(Shi et al, 2017) biosynthesize metabolites containing SLB moiety, for example, 2-amino-1,4-benzoquinone (Lumiquinone A,Figure 2)and related compound 3,5-dihydroxy-4-isopropyl-trans-stilbene…”

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confidence: 99%

Stilbene derivatives as new perspective in antifungal medicinal chemistry

Filippis

Ammazzalorso

Amoroso

et al. 2019

Drug Development Research

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The high incidence and mortality of invasive fungal infections and serious drug resistance have become a global public health issue. There is an urgent need for alternative antimicrobials to control fungal infections and targeting it by antifungal substances from the natural sources represents a promising new strategy for the development of novel antifungal agents. Resveratrol (3,5,4′‐trihydroxy‐trans‐stilbene) is a phytoalexin produced by plant species in response to environmental stress or pathogenic attacks. It has many known and potential therapeutic applications in human general homeostasis; it mediates a great number of biological responses relevant for human health such as anticancer, cardio and neuroprotective, antioxidant, and antimicrobial activities. Resveratrol is a natural antifungal agent, therefore it can be considered as a scaffold for designing structural relatives potentially capable of mediating more intense responses in a more specific way. Also, stilbenes produced by several plants may be useful lead structure for the chemical synthesis of antifungal. Their antifungal potential represents a useful solution to the drug resistance and side effect complications that occur after pharmacological treatment of infectious diseases. The purpose of this review is to present an overview on resveratrol derivatives, both natural and synthetic, with antifungal activity and summarize the chemical structure and the therapeutic versatility of stilbene‐containing compounds.

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“…Both weeds and plant fungal diseases have always been thought as big agricultural and environmental problems [ 1 , 2 , 3 ]. Organic synthetic herbicides and fungicides are widely used to control these issues.…”

Section: Introductionmentioning

confidence: 99%

Phytotoxic and Antifungal Metabolites from Curvularia crepinii QTYC-1 Isolated from the Gut of Pantala flavescens

et al. 2018

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Four metabolites (1–4), including a new macrolide, O-demethylated-zeaenol (2), and three known compounds, zeaenol (1), adenosine (3), and ergosta-5,7,22-trien-3b-ol (4) were isolated and purified from Curvularia crepinii QTYC-1, a fungus residing in the gut of Pantala flavescens. The structures of isolated compounds were identified on the basis of extensive spectroscopic analysis and by comparison of the corresponding data with those reported in the literature previously. The new compound 2 showed good phytotoxic activity against Echinochloa crusgalli with an IC50 value of less than 5 µg/mL, which was comparable to that of positive 2,4-dichlorophenoxyacetic acid (2,4-D). Compound 1 exhibited moderate herbicidal activity against E. crusgalli with an IC50 value of 28.8 μg/mL. Furthermore, the new metabolite 2 was found to possess moderate antifungal activity against Valsa mali at the concentration of 100 µg/mL, with the inhibition rate of 50%. These results suggest that the new macrolide 2 and the known compound 1 have potential to be used as biocontrol agents in agriculture.

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Stilbene Derivatives from Photorhabdus temperata SN259 and Their Antifungal Activities against Phytopathogenic Fungi

Cited by 52 publications

References 28 publications

Antibacterial activity of Xenorhabdus and Photorhabdus isolated from entomopathogenic nematodes against antibiotic-resistant bacteria

Antibacterial activity of Xenorhabdus and Photorhabdus isolated from entomopathogenic nematodes against antibiotic-resistant bacteria

Stilbene derivatives as new perspective in antifungal medicinal chemistry

Phytotoxic and Antifungal Metabolites from Curvularia crepinii QTYC-1 Isolated from the Gut of Pantala flavescens

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