Antifungal properties of natural products from <i>Pterocarya tonkinensis</i> against phytopathogenic fungi

Ngo, Men Thi; Han, Jae Woo; Minh, Nguyen Van; Dang, Quang Le; Kim, Hun; Choi, Gyung Ja

doi:10.1002/ps.6211

Cited by 8 publications

(17 citation statements)

References 48 publications

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“…hordei ), and pepper anthracnose (PAN, caused by C. coccodes ). We performed the plant disease control efficacy assay as previously described ( Lee et al, 2007 ; Ngo et al, 2021 ). Briefly, rice ( Oryza sativa L, cv.…”

Section: Methodsmentioning

confidence: 99%

Biocontrol Potential of Aspergillus Species Producing Antimicrobial Metabolites

et al. 2021

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Microbial metabolites have been recognized as an important source for the discovery of new antifungal agents because of their diverse chemical structures with novel modes of action. In the course of our screening for new antifungal agents from microbes, we found that culture filtrates of two fungal species Aspergillus candidus SFC20200425-M11 and Aspergillus montenegroi SFC20200425-M27 have the potentials to reduce the development of fungal plant diseases such as tomato late blight and wheat leaf rust. From these two Aspergillus spp., we isolated a total of seven active compounds, including two new compounds (4 and 6), and identified their chemical structures based on the NMR spectral analyses: sphaeropsidin A (1), (R)-formosusin A (2), (R)-variotin (3), candidusin (4), asperlin (5), montenegrol (6), and protulactone A (7). Based on the results of the in vitro bioassays of 11 plant pathogenic fungi and bacteria, sphaeropsidin A (1), (R)-formosusin A (2), (R)-variotin (3), and asperlin (5) exhibited a wide range of antimicrobial activity. Furthermore, when plants were treated with sphaeropsidin A (1) and (R)-formosusin A (2) at a concentration of 500 μg/ml, sphaeropsidin A (1) exhibited an efficacy disease control value of 96 and 90% compared to non-treated control against tomato late blight and wheat leaf rust, and (R)-formosusin A (2) strongly reduced the development of tomato gray mold by 82%. Asperlin (5) at a concentration of 500 μg/ml effectively controlled the development of tomato late blight and wheat leaf rust with a disease control value of 95%. Given that culture filtrates and active compounds derived from two Aspergillus spp. exhibited disease control efficacies, our results suggest that the Aspergillus-produced antifungal compounds could be useful for the development of new natural fungicides.

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Section: Methodsmentioning

confidence: 99%

Biocontrol Potential of Aspergillus Species Producing Antimicrobial Metabolites

et al. 2021

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“…Each fraction was concentrated to dryness under reduced pressure using a Rotavapor R-300 rotary evaporator (Büchi) at 40 °C to yield an EtOAc fraction (46 g), BuOH fraction (35 g), and water fraction (18 g). Because the EtOAc fraction exclusively had effects on the disease development of rice blast and wheat leaf rust, the EtOAc fraction was used to identify the active components using various chromatographic processes [ 8 , 9 , 10 ]. The EtOAc fraction was loaded onto a silica gel column (70–230 mesh; Merck, Darmstadt, Germany) and successively eluted with a gradient of hexane/EtOAc (95:5 to 0:100, v / v ), yielding twelve fractions E1–E12.…”

Section: Methodsmentioning

confidence: 99%

“…hordei ), and pepper anthracnose (PAN; caused by C. coccodes ). The preparation of the plants, inoculation method, and evaluation of the control efficacy were performed as previously described [ 10 ]. Briefly, for the development of RCB, two or three-leaf stages of rice plants were inoculated by spraying with a spore suspension (5 × 10 5 conidia/mL) of M. oryzae .…”

Section: Methodsmentioning

confidence: 99%

“…Briefly, for the development of RCB, two or three-leaf stages of rice plants were inoculated by spraying with a spore suspension (5 × 10 5 conidia/mL) of M. oryzae . The inoculated plants were incubated at 25 °C for 5 days, and then the disease control efficacy was calculated with the following equation: control efficacy (%) = 100 × (1 − B/A), where A is the mean of lesion area (%) on the leaves of the control plants, and B is the mean of lesion area (%) on the leaves of the treated plants [ 10 ]. Developmental conditions for other plant diseases were described in Table S2 .…”

Section: Methodsmentioning

confidence: 99%

“…Moreover, considering that natural compounds isolated from plants are structurally diverse and complex, natural substances can exhibit a broad range of biological activities [ 6 ]. Based on antimicrobial activity, many plant extracts and their active compounds have been reported to have antifungal effects in vitro and in vivo [ 7 , 8 , 9 , 10 ]. In particular, plant species such as Azadirachta indica A. Juss.…”

Section: Introductionmentioning

confidence: 99%

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Plant Disease Control Efficacy of Platycladus orientalis and Its Antifungal Compounds

Bae

Han

Dang³

et al. 2021

Plants

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Plants contain a number of bioactive compounds that exhibit antimicrobial activity, which can be recognized as an important source of agrochemicals for plant disease control. In searching for natural alternatives to synthetic fungicides, we found that a methanol extract of the plant species Platycladus orientalis suppressed the disease development of rice blast caused by Magnaporthe oryzae. Through a series of chromatography procedures in combination with activity-guided fractionation, we isolated and identified a total of eleven compounds including four labdane-type diterpenes (1–4), six isopimarane-type diterpenes (5–10), and one sesquiterpene (11). Of the identified compounds, the MIC values of compounds 1, 2, 5 & 6 mixture, 9, and 11 ranged from 100 to 200 μg/mL against M. oryzae, whereas the other compounds were over 200 μg/mL. When rice plants were treated with the antifungal compounds, compounds 1, 2, and 9 effectively suppressed the development of rice blast at all concentrations tested by over 75% compared to the non-treatment control. In addition, a mixture of compounds 5 & 6 that constituted 66% of the P. orientalis ethyl acetate fraction also exhibited a moderate disease control efficacy. Together, our data suggest that the methanol extract of P. orientalis including terpenoid compounds has potential as a crop protection agent.

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Expedient discovery of novel oxime ester derivatives of piperine/piperine analogs as potent pesticide candidates and their mode of action against Tetranychus cinnabarinus Boisduval

Wen

et al. 2023

Pest Management Science

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BACKGROUNDNowadays, pest infestation and resistance have appeared as a consequence of repeated and extensive use of pesticides. Thus, development of new effective pesticide candidates in crop protection is highly desirable. Herein, a series of new piperine derivatives containing oxime ester scaffolds were regioselectively and stereoselectively prepared as pesticidal agents.RESULTSSteric configurations of compounds 2, 5z and 13e were definitively determined by single‐crystal X‐ray diffraction. Against Tetranychus cinnabarinus, notably, compounds 5f [median lethal concentration (LC50) = 0.14 mg mL−1] and 5v (LC50 = 0.13 mg mL−1) showed >107‐fold greater acaricidal activity than piperine (LC50 = 15.02 mg mL−1), which were comparable to the commercial acaricide spirodiclofen. Against Aphis citricola, compound 5d (LD50 = 19.12 ng aphid−1) exhibited 6.1‐fold more potent aphicidal activity than piperine (LD50 = 116.06 ng aphid−1). Additionally, through scanning electron microscopy, the toxicology study suggested that the acaricidal activity of piperine derivatives may be related to damage of the cuticle layer crest of T. cinnabarinus.CONCLUSIONThe structure–activity relationships suggested that 3,4‐dioxymethylene of piperine was crucial for its acaricidal activity; and introduction of a certain length of aliphatic chain at the C‐2 position was beneficial to the aphicidal and acaricidal activities. Compounds 5f and 5v are potential leads for further structural modification as acaricidal agents. © 2023 Society of Chemical Industry.

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Antifungal properties of natural products from Pterocarya tonkinensis against phytopathogenic fungi

Cited by 8 publications

References 48 publications

Biocontrol Potential of Aspergillus Species Producing Antimicrobial Metabolites

Biocontrol Potential of Aspergillus Species Producing Antimicrobial Metabolites

Plant Disease Control Efficacy of Platycladus orientalis and Its Antifungal Compounds

Expedient discovery of novel oxime ester derivatives of piperine/piperine analogs as potent pesticide candidates and their mode of action against Tetranychus cinnabarinus Boisduval

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