scholarly journals Novel Inulin Derivatives Modified with Schiff Bases: Synthesis, Characterization, and Antifungal Activity

Polymers ◽  
2019 ◽  
Vol 11 (6) ◽  
pp. 998 ◽  
Author(s):  
Yuan Chen ◽  
Yingqi Mi ◽  
Xueqi Sun ◽  
Jingjing Zhang ◽  
Qing Li ◽  
...  

In this paper, we report chemical modifications of inulin by seven kinds of aromatic Schiff bases, which are different from their substituent groups. The obtained inulin derivatives were confirmed by FTIR, 1H NMR, and 13C NMR. Then, we studied their antifungal activity against four kinds of plant pathogens involving Botrytis cinerea, Fusarium oxysporum f. sp. cucumerium Owen, Fusarium oxysporum f. sp. niveum, and Phomopsis asparagi by the mycelium growth rate method. The results revealed that all inulin derivatives were endowed with significant antifungal activity compared to inulin. Among them, 6-amino-(N-4-chlorobenzylidene)-6-deoxy-3,4-di-O-acetyl inulin (4CBSAIL) and 6-amino-(N-3,4-dichlorobenzylidene)-6-deoxy-3,4-di-O-acetyl inulin (3,4DCBSAIL), which were synthesized from p-chlorobenzaldehyde and 3,4-dichlorobenzaldehyde, could completely inhibit the growth of the test fungi at 1.0 mg/mL. The inhibitory indices of the inulin derivatives were related to the type, position, and number of substituent groups (halogens) on the Schiff bases. The results confirmed that it was feasible to chemically modify inulin with Schiff bases to confer high antifungal activity to inulin. The products described in this paper have great potential as alternatives to some harmful pesticides used for plant disease control.

2012 ◽  
Vol 59 (2) ◽  
pp. 51-58 ◽  
Author(s):  
Alicja Saniewska ◽  
Anna Jarecka ◽  
Zbigniew Biały ◽  
Marian Jurzysta

Antifungal activity of total saponins originated from roots of <i>Medicago hybrida</i> (Pourret) Trautv. were evaluated <i>in vitro</i> against six pathogenic fungi and eight individual major saponin glycosides were tested against one of the most susceptible fungi. The total saponins showed fungitoxic effect at all investigated concentrations (0.01%, 0.05% and 0.1%) but their potency was different for individual fungi. The highest saponin concentration (0.1%) was the most effective and the inhibition of <i>Fusarium oxysporum</i> f. sp. <i>callistephi</i>, <i>Botrytis cinerea</i>, <i>Botrytis tulipae</i>, <i>Phoma narcissi</i>, <i>Fusarium oxysporum</i> f. sp. <i>narcissi</i> was 84.4%, 69.9%, 68.6%, 57.2%, 55.0%, respectively. While <i>Fusarium oxysporum</i> Schlecht., a pathogen of <i>Muscari armeniacum</i>, was inhibited by 9.5% only. Eight major saponin glycosides isolated from the total saponins of <i>M. hybrida</i> roots were tested against the mycelium growth of <i>Botrytis tulipae</i>. The mycelium growth of the pathogen was greatly inhibited by hederagenin 3-O-<i>β</i>-D-glucopyranoside and medicagenic acid 3-O-<i>β</i>-D-glucopyranoside. Medicagenic acid 3-O-<i>β</i>-D-glucuronopyranosyl-28-O-<i>β</i>-D-glucopyranoside and oleanolic acid 3-O-[<i>β</i>-D-glucuronopyranosyl(1→2)-<i>α</i>-L-galactopyranosyl]-28-O-<i>β</i>-D-glucopyranoside showed low fungitoxic activity. Medicagenic acid 3-O-a-D-glucopyranosyl- 28-O-β-D-glucopyranoside, hederagenin 3-O-[α-L- hamnopyranosyl(1→2)-β-D-glucopyranosyl(1→2)-β-D-glucopyranosyl]- 28-O-α-D-glucopyranoside and hederagenin 3-O-<i>β</i>-D-glucuronopyranosyl-28-O-<i>β</i>-D- lucopyranoside did not limit or only slightly inhibited growth of the tested pathogen. While 2<i>β</i>, 3<i>β</i>-dihydroxyolean-12 ene-23-al-28-oic acid 3-O-<i>β</i>-D-glucuronopyranosyl-28-O-<i>β</i>-D-glucopyranoside slightly stimulated mycelium growth of <i>B. tulipae</i>.


Polymers ◽  
2019 ◽  
Vol 11 (2) ◽  
pp. 371 ◽  
Author(s):  
Lijie Wei ◽  
Wenqiang Tan ◽  
Jingjing Zhang ◽  
Yingqi Mi ◽  
Fang Dong ◽  
...  

As a renewable, biocompatible, and biodegradable polysaccharide, inulin has a good solubility in water and some physiological functions. Chemical modification is one of the important methods to improve the bioactivity of inulin. In this paper, based on 6-amino-6-deoxy-3,4-acetyl inulin (3), three kinds of Schiff bases of inulin bearing pyridine rings were successfully designed and synthesized. Detailed structural characterization was carried out using FTIR, 13C NMR, and 1H NMR spectroscopy, and elemental analysis. Moreover, the antifungal activity of Schiff bases of inulin against three plant pathogenic fungi, including Botrytis cinerea, Fusarium oxysporum f.sp.niveum, and Phomopsis asparagi, were evaluated using in vitro hypha measurements. Inulin, as a natural polysaccharide, did not possess any antifungal activity at the tested concentration against the targeted fungi. Compared with inulin and the intermediate product 6-amino-6-deoxy-3,4-acetyl inulin (3), all the synthesized Schiff bases of inulin derivatives with >54.0% inhibitory index at 2.0 mg/mL exhibited enhanced antifungal activity. 3NS, with an inhibitory index of 77.0% exhibited good antifungal activity against Botrytis cinerea at 2.0 mg/mL. The synthesized Schiff bases of inulin bearing pyridine rings can be prepared for novel antifungal agents to expand the application of inulin.


2017 ◽  
Vol 10 (1) ◽  
pp. 10-20 ◽  
Author(s):  
Mohammed H. Abass

Objective:The profound negative impact of chemical fungicides on human and animal health, as well as, the whole agroecosystem encouraged tremendous efforts to find alternative approaches to suppress the growth of plant pathogens.Method:Recently, plant hormones have been considered to reduce fungal severity. Five different plant hormones namely 2, 4-D (2,4-Dichlorophenoxyacetic acid); BAP (6- Benzylaminopurine); Dicamba (3,6- Dichloro-2-methoxybenzoic acid, 3,6-Dichloro-o-anisic acid); IAA (Indole-2-acetic acid) and SA (Salicylic acid) were selected to examine their antifungal activity against the growth of two species of date palm fungal pathogenNigrosporaspp.Results:Results showed that SA at 50 ppm was sufficient to inhibit the mycelium growth ofN. oryzaecompletely, while withN. sphaerica; the treatments of 2, 4-D (40-50 ppm) and SA (40-50 ppm) led to similar complete inhibition results of mycelium growth. The data of BAP and IAA indicated no toxic effect toward mycelium growth of the pathogens. Similar trends of results have been obtained for phytotoxicity bioassay which performed on detached date palm leaves, 2, 4-D and SA at 30 ppm led to a complete inhibition for the production of toxins in the culture ofN. oryzaeandN. sphaerica.Conclusion:58% significant reduction in toxin production was obtained with Dicamba 30 ppm. Results presented here reveal the antifungal activity of different plant hormones inin vitroexperiments, and are important to examine their efficiency in farther field studies on date palm.


2020 ◽  
Vol 0 (0) ◽  
Author(s):  
Zhongfu Luo ◽  
Yu Deng ◽  
Bilan Luo ◽  
Yong Li ◽  
Qing Lan ◽  
...  

AbstractIn order to obtain novel botanical fungicides, three series of novel 6-substituted n-butyphthalide derivatives have been designed and synthesized via nucleophilic addition, reduction, nitrification, amination, sulfonation, Sandmeyer and Suzuki reaction. The mycelium growth rate method was used to evaluate the inhibition activity against eight phytopathogenic fungi in vitro. Preliminary bioassay tests showed that compounds 6f, 6n, 6p, 6r and 7a exhibited better activity for some fungi at 50 μg/mL than the positive drug hymexazol and lead compound n-butyphthalide (NBP). The preliminary structure–activity relationships indicated that the antifungal activity is significantly affected by the substituents on the benzene ring.


2020 ◽  
Vol 4 (1) ◽  
pp. 20-26
Author(s):  
Oktira Roka Aji ◽  
Yuni Rohmawati

Fusarium oxysporum is an important disease that causes wilt disease in plants. Fungal pathogen control using synthetic fungicides can cause negative impacts on the environment. Morinda citrifolia is one of the herbs that is known for many benefits. M. citrifolia leaf contains anthraquinone which have potential as antifungal agents. In this study, in vitro anti-fungal assay was conducted against F. oxysporum to analyze the antifungal activity of ethanol extract of M. citrifolia leaves. In vitro evaluation was carried out using poisoned food technique at four different concentrations i.e., 20%, 40%, 60% and 80%. The results showed concentration 60% gave the highest inhibitory effect (21,82%) on F. oxysporum mycelium growth.


2021 ◽  
Author(s):  
Kavita Negi ◽  
Preeti Chaturvedi

Tomato, a high valuevegetable crop, suffers huge production losses in tropics due to a wilt disease caused by Fusarium oxysporum f. sp. lycopersici . Present study was undertaken to find an effective biocontrol method to check fusarium wilt in order to curb the losses suffered by the crop growers. Organic extracts(acetone, methanol/ethanol) of thalloid bryophytes ( Conocephalumconicum (L.) Dumort. and Marchantiapapillata Raddi subsp. grossibarba (Steph.) Bischl. ) were tested against F. oxysporum f. sp. lycopersici using disc diffusion and micro broth dilution assay.Methanol extract of C.conicum (L.) Dumort. (CCDM) showed significantly high antifungal activity (85.5% mycelial inhibition; 31.25µg/mL MIC and 125µg/mL MFC).Potential of methanol extract was und, Riccardin C constituting 50% of the total number of compoundstested in a glasshouse experiment on tomato, which illustrated the efficacy of the plant extract to control the fusarial wilt. Morphological and ultrastructural alterationsin CCDM treated fusarium myceliawere observed in scanning electron microscopy. GC-MS analysis of CCDM extract showed the presence of51 constituents, and the dominant compounds werebis (bibenzyl), acyclic alkanes, fatty acids, sesquiterpenpoids and steroids. The study suggested that C. conicum being an efficient source of Riccardin C like antifungal compounds provides a potent and eco-friendly alternative to conventional fungicides in vegetables.


2013 ◽  
Vol 647 ◽  
pp. 548-553 ◽  
Author(s):  
Yong Gang Li ◽  
Qi Xin Xi ◽  
Sheng Yan Wen ◽  
Ying Mei Li

Botrytis cinerea is a necrotrophic fungus that affects many plant species requiring new methods of control. In the present investigation, efficacy of potash alum, a traditionally known double salt in Indian and Chinese medicine system, was tested against fourteen plant pathogenic fungi, inhibition mechanism and field efficacy of 5% potash alum water solution (M1) against tomato gray mold caused by B. cinerea. The inhibition spectrum tests showed that M1 had some inhibition effect against fourteen pathologic fungi by adopting mycelium growth rate method. M1 had an inhibition rate of 81.5%, 100%, 100% and 93.58% against B. clnerea, P. aphanidermatum, F. equiset and S. sclerotiorum respectively. M1 could effectively inhibit mycelial growth, spores production and germination of B. cinerea. The results preliminary showed that M1 had no effect on tomato growth. Tomato gray mold caused by B. cinerea had effectively been prevented by using M1 with field efficacy, which control effect was 78.66%. So the study lay the groundwork for further research and application.


Author(s):  
Anna Biernasiuk ◽  
Anna Berecka-Rycerz ◽  
Anna Gumieniczek ◽  
Maria Malm ◽  
Krzysztof Z. Łączkowski ◽  
...  

Abstract Recently, the occurrence of candidiasis has increased dramatically, especially in immunocompromised patients. Additionally, their treatment is often ineffective due to the resistance of yeasts to antimycotics. Therefore, there is a need to search for new antifungals. A series of nine newly synthesized thiazole derivatives containing the cyclopropane system, showing promising activity against Candida spp., has been further investigated. We decided to verify their antifungal activity towards clinical Candida albicans isolated from the oral cavity of patients with hematological malignancies and investigate the mode of action on fungal cell, the effect of combination with the selected antimycotics, toxicity to erythrocytes, and lipophilicity. These studies were performed by the broth microdilution method, test with sorbitol and ergosterol, checkerboard technique, erythrocyte lysis assay, and reversed phase thin-layer chromatography, respectively. All derivatives showed very strong activity (similar and even higher than nystatin) against all C. albicans isolates with minimal inhibitory concentration (MIC) = 0.008–7.81 µg/mL Their mechanism of action may be related to action within the fungal cell wall structure and/or within the cell membrane. The interactions between the derivatives and the selected antimycotics (nystatin, chlorhexidine, and thymol) showed additive effect only in the case of combination some of them and thymol. The erythrocyte lysis assay confirmed the low cytotoxicity of these compounds as compared to nystatin. The high lipophilicity of the derivatives was related with their high antifungal activity. The present studies confirm that the studied thiazole derivatives containing the cyclopropane system appear to be a very promising group of compounds in treatment of infections caused by C. albicans. However, this requires further studies in vivo. Key points • The newly thiazoles showed high antifungal activity and some of them — additive effect in combination with thymol. • Their mode of action may be related with the influence on the structure of the fungal cell wall and/or the cell membrane. • The low cytotoxicity against erythrocytes and high lipophilicity of these derivatives are their additional good properties. Graphical abstract


Author(s):  
César A. C. de Medeiros ◽  
Ânderson de V. Pinto ◽  
Josenildo C. de Oliveira ◽  
Gezaíldo S. Silva ◽  
Juliana M. M. Arrua ◽  
...  

2021 ◽  
Vol 3 (4) ◽  
Author(s):  
Ilgin Akpinar ◽  
Muammer Unal ◽  
Taner Sar

AbstractFusarium species are the primary fungal pathogen affecting agricultural foodstuffs both in crop yield and economic loss. Due to these problems, control of phytopathogenic fungi has become one of the critical problems around the World. Nanotechnology is a new technology with potential in many fields, including agriculture. This study focused on determining potential effects of silver nanoparticles (AgNPs) with different nanosizes (3, 5, 8 and 10 nm) and at different concentrations (12.5–100 ppm) against phytopathogenic Fusarium oxysporum f. sp. radicis-lycopersici (FORL) strains. The maximum antifungal activity was achieved by decreasing nanosize and increasing concentration of AgNPs. Mycelium growth abilities were decreased about 50%, 75% and 90% by AgNPs treatment with 3 nm sizes at 25 ppm, 37.5 ppm and 50 ppm concentrations, respectively. The productivity of fungal biomass in the liquid growth media was found to be too limited at the 25–37.5 ppm of AgNPs concentrations with all sizes. In addition, both septation number and dimensions of micro- and macroconidia were found to be gradually decreased with the application of silver nanoparticles. This work showed that the low concentration of AgNPs could be used as potential antifungal agents and applied for control of phytopathogens.


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