Mode of action of 3-butylidene phthalide as a competent natural pesticide

Abbod, Mohsen; Safaie, Naser; Gholivand, Khodayar; Mehrabadi, Mohammad; Bonsaii, Mahyar

doi:10.1016/j.pestbp.2020.02.003

Cited by 8 publications

(5 citation statements)

References 52 publications

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“…However, these compounds have been described as inhibitors of the DNA topoisomerase type II in Leishmania genus( Mishra et al, 2014 ). On the other hand, anti-acetylcholinesterase properties have been also recently stated in some fungi species( Abbod et al, 2020 ).…”

Section: Discussionmentioning

confidence: 86%

The therapeutic potential of novel isobenzofuranones against Naegleria fowleri

Rizo-Liendo

Arberas-Jiménez

Sifaoui

et al. 2021

International Journal for Parasitology: Drugs and Drug Resistan

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The Free-Living Amoeba species, Naegleria fowleri is the causative agent of a lethal encephalitis known as Primary Amoebic Encephalitis (PAM). Moreover, most of the reported cases are often related to swimming and/or diving in aquatic environments. In addition, the current therapeutic options against PAM are not fully effective and hence, there is an urgent need to develop novel therapeutic agents against this disease. Previously isobenzofuranones compounds have been reported to present antiprotozoal and antifungal activity among others. However, to the best of our knowledge, these molecules have not been previously tested against N. fowleri . Therefore, the aim of this study was to evaluate the activity of 14 novel isobenzofuranones against this pathogenic amoeba. The most active and less toxic molecules, were assayed in order to check induction of Programmed Cell Death (PCD) in the treated amoebae. The obtained results showed that these molecules were able to eliminate N. fowleri trophozoites and also induced PCD. Therefore, the tested isobenzofuranones could be potential therapeutic candidates for the treatment of PAM.

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Section: Discussionmentioning

confidence: 86%

The therapeutic potential of novel isobenzofuranones against Naegleria fowleri

Rizo-Liendo

Arberas-Jiménez

Sifaoui

et al. 2021

International Journal for Parasitology: Drugs and Drug Resistan

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“…The 3-butylidene phthalide exhibited phytotoxicity against the plant Lemna minor but non-toxic at concentration that inhibited the fungus M. phaseolina. 49) Additionally, 5,7-dihydroxy-3(R)-methylphthalide isolated from the endophytic fungus Xylaria brevipes was also found to be phytotoxic. 52) The effectiveness of 4,6-dimethoxyphthalide and 5,7-dimethoxyphthalide against fungal pathogens serves as baseline information for future studies aiming to elucidate the possible mode of action of these phthalide compounds.…”

Section: Discussionmentioning

confidence: 99%

“…A study regarding the phthalide compound, 3-butylidene phthalide reported that its mode of action is the inhibition of melanin biosynthesis in the fungus Macrophomina phaseolina . 49 ) Plant pathogenic fungi protect themselves against ultraviolet light, toxins, and other environmental factors through the production of melanin. 50 ) Additionally, bacteria can produce several types of melanin important for their pathogenesis, survival in different types of environments, and interactions with other organisms.…”

Section: Discussionmentioning

confidence: 99%

Identification of two phthalide derivatives and an oxindole compound isolated from the edible mushroom <i>Pleurotus ostreatus</i> and their inhibitory activities against plant pathogenic microorganisms

Cabutaje,

Ueno,

Osaki-Oka

et al. 2023

J. Pestic. Sci.

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The excessive use of chemical pesticides in agricultural fields for controlling plant pathogenic microorganisms harms human health, the environment, and other beneficial microorganisms in the soil and plants. To address this challenge, it is essential to isolate and discover bioactive compounds from biological resources that could inhibit plant pathogenic microorganisms. In this study, the culture filtrate of the edible mushroom Pleurotus ostreatus was subjected to bioassay-guided isolation, and two phthalide derivatives-4,6-dimethoxyphthalide (1) and 5,7-dimethoxyphthalide (2)-were identified, along with an oxindole compound-3-hydroxy-3-methyloxindole (3). The inhibitory activities of the three compounds were evaluated against four fungal and five bacterial pathogens. Remarkably, 1 and 2 exhibited the lowest IC 50 values against the conidial germination and germ tube elongation of the rice blast fungus Pyricularia oryzae. However, their effectiveness against bacterial pathogens was relatively low. The (S) and (R)-enantiomers of 3-hydroxy-3-methyloxindole showed different activities against plant fungal pathogens and bacterial plant pathogens.

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“…It has been reported that butylidenephthalide has a high affinity for trihydroxy naphthalene reductase in Macrophomina phaseolina, a key enzyme for melanin biosynthesis in pathogens. 63 Sclerotia is an important life stage of S. rolfsii and plays an important role in the disease cycle. 7 The melanin on sclerotia can resist adverse factors such as UV light, toxic metals and antagonistic microorganisms.…”

Section: Discussionmentioning

confidence: 99%

Antifungal activity of Ligusticum chuanxiong essential oil and its active composition butylidenephthalide against Sclerotium rolfsii

Cui,

He,

Wang

et al. 2023

Pest Management Science

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BACKGROUNDPeanut stem rot caused by Sclerotium rolfsii is an epidemic disastrous soil‐borne disease. Recently, natural products tend to be safe alternative antifungal agents to combat pathogens.RESULTSThis work determined the preliminary antifungal activity of 29 essential oils against S. rolfsii and found that Ligusticum chuanxiong essential oil (LCEO) showed the best antifungal activity, with an EC50 value of 81.79 mg/L. Sixteen compositions (98.78%) were identified in LCEO by GC‐MS analysis, the major compositions were five phthalides (93.14%). Among these 5 phthalides, butylidenephthalide was the most effective compound against S. rolfsii. Butylidenephthalide not only exhibited favorable in vitro antifungal activity against the mycelial growth, sclerotia production and germination of S. rolfsi, but also presented efficient in vivo efficacy in the control of peanut stem rot. Seven days after application in greenhouse, the protective and curative efficacy of butylidenephthalide at 300 mg/L (52.02%, 44.88%) and LCEO at 1,000 mg/L (49.60%, 44.29%) against S. rolfsii were similar to that of the reference fungicide polyoxin at 300 mg/L (54.61%, 48.28%). Butylidenephthalide also significantly decreased the oxalic acid and polygalacturonase content of S. rolfsii, suggesting a decreased infection ability on plants. Results of biochemical actions indicated that butylidenephthalide did not have any effect on the cell membrane integrity and permeability but significantly decreased nutrient contents, disrupted the mitochondrial membrane, inhibited energy metabolism and induced reactive oxygen species (ROS) accumulation of S. rolfsii.CONCLUSIONOur results could provide an important reference for understanding the application potential and mechanisms of butylidenephthalide in the control of S. rolfsii.This article is protected by copyright. All rights reserved.

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Mode of action of 3-butylidene phthalide as a competent natural pesticide

Cited by 8 publications

References 52 publications

The therapeutic potential of novel isobenzofuranones against Naegleria fowleri

The therapeutic potential of novel isobenzofuranones against Naegleria fowleri

Identification of two phthalide derivatives and an oxindole compound isolated from the edible mushroom <i>Pleurotus ostreatus</i> and their inhibitory activities against plant pathogenic microorganisms

Antifungal activity of Ligusticum chuanxiong essential oil and its active composition butylidenephthalide against Sclerotium rolfsii

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