Natural products as sources of new fungicides (IV): Synthesis and biological evaluation of isobutyrophenone analogs as potential inhibitors of class-II fructose-1,6-bisphosphate aldolase

Li, Ding; Luong, Tuong Thi Mai; Dan, Wenjia; Ren, Yanliang; Nien, Hoang Xuan; Zhang, Anling; Gao, Jin‐Ming

doi:10.1016/j.bmc.2017.10.046

Cited by 19 publications

(24 citation statements)

References 32 publications

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“…Natural products have been a strong lead in the discovery and development of novel fungicides (Daoubi et al, 2005;Li et al, 2018;Musso et al, 2012). In the present study, we demonstrate that both t-CA and p-CA are potentially useful anti-FON agents and possible lead compounds for the development of new synthetic fungicides.…”

Section: Handling Editor : Junhyun Jeonsupporting

confidence: 56%

Inhibition of Fusarium oxysporum f. sp. nicotianae Growth by Phenylpropanoid Pathway Intermediates

et al. 2020

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Fusarium wilt in tobacco caused by the fungus Fusarium oxysporum f. sp. nicotianae is a disease-management challenge worldwide, as there are few effective and environmentally benign chemical agents for its control. This challenge results in substantial losses in both the quality and yield of tobacco products. Based on an in vitro analysis of the effects of different phenylpropanoid intermediates, we found that the early intermediates trans-cinnamic acid and para-coumaric acid effectively inhibit the mycelial growth of F. oxysporum f. sp. nicotianae strain FW316F, whereas the downstream intermediates quercetin and caffeic acid exhibit no fungicidal properties. Therefore, our in vitro screen suggests that trans-cinnamic acid and para-coumaric acid are promising chemical agents and natural lead compounds for the suppression of F. oxysporum f. sp. nicotianae growth.

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Section: Handling Editor : Junhyun Jeonsupporting

confidence: 56%

Inhibition of Fusarium oxysporum f. sp. nicotianae Growth by Phenylpropanoid Pathway Intermediates

et al. 2020

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“…The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By column chromatography purification of the crude product obtained (ethyl acetate/heptane gradient), 1-[1,1'-bi(cyclopropyl)-2-yl]-6-nitro-3,4dihydroquinolin-2(1H)-one (480 mg, 86 %) was isolated as a colorless solid, 1 ). In the next step, 1-[1,1'-bi(cyclopropyl)-2-yl]-6nitro-3,4-dihydroquinolin-2(1H)-one (480 mg, 1.76 mmol) was added together with tin(II) chloride dihydrate (1591 mg, 7.05 mmol) to abs.…”

Section: Methodsmentioning

confidence: 99%

“…Substituents [a] In vitro activity ABI1-In vivo efficacy vs. drought stress R 1 R 2 (AtRCAR11) [b] [ [a] c-Pr = cyclopropyl, c-Bu = cyclobutyl, n-Pr = n-propyl, c-Pent = cyclopentyl, c-Hexyl; [b] a final expert assessment of target affinity was made according to the following classification: "-" = activity < 30 %, " + " = 30 % < activity < 50 %, " + + " = 50 % < activity < 70 %, " + + + " = 70 % < activity < 90 %" " + + + + " = activity > 90 %; [c] standard application rate for crop protection greenhouse trials; [d] a final expert assessment of efficacies was made according to the following classification: "0" = no effect, " + " = slight beneficial effect, " + + " = significant beneficial effect, " + + + " = strong beneficial effect against drought stress, " + + + + " = very strong effect superior to internal standard ABA (comparative visual assessment of greenmass).…”

Section: Entrymentioning

confidence: 99%

Synthesis and Exploration of Abscisic Acid Receptor Agonists Against Dought Stress by Adding Constraint to a Tetrahydroquinoline‐Based Lead Structure

et al. 2021

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New oxotetrahydroquinolinyl-and oxindolinyl sulfonamides interacting with RCAR/(PYR/PYL) receptor proteins were identified as lead structures against drought stress in crops starting from protein docking studies of a sulfonamide lead structure, followed by in-depth SAR studies. Optimized five to six step synthetic approaches via substituted amino oxo-tetrahydroquinolines and amino oxo-indolines as essential intermediates gave access to the envisaged oxo-tetrahydroquinolinyl and oxindolinyl sulfonamides. Whilst oxo-tetrahydroquinolinyl sulfonamides with additional carbon substituents or spiro-cycloalkyl groups exhibited only low to moderate target affinities, the corresponding spiro-oxindolinyl and oxo-tetrahydroquinolinyl sulfonamides carrying optimized N-substituents revealed strong interactions with RCAR/(PYR/PYL) receptor proteins in Arabidopsis thaliana. Remarkably, the in vitro activity observed for these new compounds was on the same level as observed for the naturally occurring plant hormone in line with strong efficacy against drought stress in-vivo (canola and wheat as broad-acre crops).

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“…Recent studies have shown that natural compounds from plants and other organisms or their derivatives can be used as fungicides (Li et al 2018;Akbar et al 2020). Various studies revealed that crude plant extracts and pure compounds are effective in controlling M. phaseolina.…”

Section: Introductionmentioning

confidence: 99%

Bioassays Guided Fractionation of Ageratum conyzoides Extract for the Identification of Natural Antifungal Compounds against Macrophomina phaseolina

Banaras¹

2021

IJAB

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Macrophomina phaseolina (Tassi) Goid. is a soil-borne fungal pathogen causing diseases in more than 500 plant species. The present study aimed to identify possible antifungal constituents in different parts of billygoat-weed (Ageratum conyzoides L.) through bioassays guided fractionation for the control of M. phaseolina. Extracts of different parts of the weed were made in methanol and antifungal bioassays were conducted using 1, 2, 3, 4 and 5% concentrations of the extract. Stem extract caused the highest inhibition in fungal biomass (20–83%) followed by leaf extract (16–67%). Methanolic stem extract was partitioned using four organic solvents namely n-hexane, chloroform, ethyl acetate and n-butanol. Bioassays carried out with different concentrations (3.125, 6.25, 12.5, 25, 50, 100 and 200 mg mL-1) of the sub-fractions of stem extract revealed the highest antifungal potential of chloroform sub-fraction with 56–93% reduction in the fungal biomass followed by n-butanol, ethyl acetate and n-hexane sub-fractions causing 24–76%, 7–75% and 5–70% reduction in fungal biomass over control, respectively. Chloroform sub-fraction with the highest antifungal potential was analyzed by GC-MS. Out of 10 compounds identified in this sub-fraction, 2H-1-benzopyran, 7-dimethoxy-2,2-dimethyl- (27.58%) was the most abundant followed by hexadecanoic acid, methyl ester (18.85%); 11-octadecenoic acid, methyl ester (15.28%) and 1,2-benzenedicarboxylic acid, mono(2-ethylhexyl) ester (10.88%), which could be responsible for antifungal activity. © 2021 Friends Science Publishers

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Natural products as sources of new fungicides (IV): Synthesis and biological evaluation of isobutyrophenone analogs as potential inhibitors of class-II fructose-1,6-bisphosphate aldolase

Cited by 19 publications

References 32 publications

Inhibition of Fusarium oxysporum f. sp. nicotianae Growth by Phenylpropanoid Pathway Intermediates

Inhibition of Fusarium oxysporum f. sp. nicotianae Growth by Phenylpropanoid Pathway Intermediates

Synthesis and Exploration of Abscisic Acid Receptor Agonists Against Dought Stress by Adding Constraint to a Tetrahydroquinoline‐Based Lead Structure

Bioassays Guided Fractionation of Ageratum conyzoides Extract for the Identification of Natural Antifungal Compounds against Macrophomina phaseolina

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