• Title/Summary/Keyword: antifungal compounds

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Synthesis and Antimicrobial Activities of Some New Nitroimidazole Derivatives

  • Benkli, Kadriye;Karaburun, Ahmet-Cagrl;Gundogdu-Karaburun, Nalan;Demirayak, Seref;Guven, Klymet
    • Archives of Pharmacal Research
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    • v.26 no.10
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    • pp.773-777
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    • 2003
  • In this study, some new nitroimidazole derivatives were obtained from 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethylamine dihydrochloride (4) and 1-(2-bromoethyl)-2-methyl-5-nitroimidazole (5), which were prepared using metronidazole. Compound 4 was reacted with arylisothiocyanates (6) to obtain 1-[2-(2-methyl-5-nitroimidazol-1-yl)ethyl]-3-arylthioureas (7) and the latter with $\alpha$-bromoacetophenones (8) to give -3-[2-(2-methyl-5-nitroimidazol-1-yl)ethyl]-2-arylimino-4-aryl-4-thiazolines (9). Also 1-[2-(2-methyl-5-nitroimidazol-1-yl)ethyl]-2-phenyl-4-arylideneimidazolin-5-ones (11) were prepared by reaction of 4 with 2-phenyl-4-arylidene-5-oxazolones (10). The reaction of the other starting material 5 with 5-arylidenethiazolidin-2,4-dione (12) gave 3-[2-(2-methyl-5-nitroimidazol-1-yl)ethyl]-5-arylidenethiazolidin-2,4-dione (13) derivatives. Structural elucidation of the compounds was performed by IR, $^1H-NMR$ and MASS spectroscopic data and elemental analysis results. Antimicrobial activities of the compounds were examined and moderate activity was obtained.

Synthesis, Spectroscopic Studies and Biological Applications of Organotin(IV) Derivatives of 3-[N-(4-Nitrophenyl)-amido]propenoic Acid and 3-[N-(4-Nitrophenyl)-amido]propanoic Acid

  • Shahid, Khadija;Shahzadi, Saira;Ali, Saqib;Mazhar, M.
    • Bulletin of the Korean Chemical Society
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    • v.27 no.1
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    • pp.44-52
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    • 2006
  • New organotin(IV) derivatives with general formulae R_2SnL_2 and R_3SnL, where R = methyl, n-butyl, n-octyl and phenyl and HL is either 3-[N-(4-nitrophenyl)amido]-propenoic acid or 3-[N-(4-nitrophenyl)amido] propanoic acid have been synthesized in 1 : 2 and 1 : 1 molar ratio by different methods. The FTIR spectra clearly demonstrated that the organotin(IV) moieties react with [O,O] atoms of the ligands. The bonding and coordination behavior in these complexes are discussed on the basis of multinuclear (^1H,\,^{13}C,\,^{119}Sn) NMR and mass spectrometric studies. Antibacterial, and antifungal screening tests were performed for these compounds and reported here. These values were compared to those of the precursors and it was found that diorganotin(IV) complexes exhibit less activity as compared to triorganotin(IV) complexes . LD_{50} data were obtained by Brine Shrimp assay method. Insecticidal activity was performed for selective compounds by contact toxicity method.

Screening and Evaluation of Yeast Antagonists for Biological Control of Botrytis cinerea on Strawberry Fruits

  • Chen, Pei-Hua;Chen, Rou-Yun;Chou, Jui-Yu
    • Mycobiology
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    • v.46 no.1
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    • pp.33-46
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    • 2018
  • Gray mold (Botrytis cinerea) is one of the most common diseases of strawberries (Fragaria${\times}$ananassa Duchesne) worldwide. Although many chemical fungicides are used for controlling the growth of B. cinerea, the risk of the fungus developing chemical resistance together with consumer demand for reducing the use of chemical fungicides have necessitated an alternative method to control this pathogen. Various naturally occurring microbes aggressively attack plant pathogens and benefit plants by suppressing diseases; these microbes are referred to as biocontrol agents. However, screening of potent biocontrol agents is essential for their further development and commercialization. In this study, 24 strains of yeast with antagonistic ability against gray mold were isolated, and the antifungal activity of the volatile and diffusible metabolites was evaluated. Putative mechanisms of action associated with the biocontrol capacity of yeast strains against B. cinerea were studied through in vitro and in vivo assays. The volatile organic compounds produced by the Galactomyces candidum JYC1146 could be useful in the biological control of plant pathogens and therefore are potential alternative fungicides with low environmental impact.

Antifungal Activity of Korean Radish (Raphanus sativaus L) Extracts Against Pathogenic Plant (한국산 무 추출물의 곰팡이 병균에 대한 항진균성)

  • Won, Hwang-Cher-
    • Journal of Life Science
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    • v.13 no.2
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    • pp.223-229
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    • 2003
  • A study of the anti-fungal properties in Korean radish was conducted using a variety of purification procedures such as Extrelut column, RP(Reverse Phase) Cl8 Column Chromatography, HPLC etc. to separate anti-fungal substances from Korean radish juices to test them against a common gray mold called Botrytis cenerea. Dialysis tube operation showed that these substances were presumably thermostable compounds with low molecular mass (less than 3.5 kDa). Differences of anti-fungal activities depending upon types of radishes used did not show any noticeable variation. The antifungals were presumably composed of more than 5 compounds. Among these, the most anti-fungal fraction was analyzed by HPLC in which one peak was obtained. Disease-affected plants were inoculated with 10mg of Extrelut fraction and results showed similar anti-fungal activity to pesticides suggesting possible usage of these substances as environmentally friendly antibiotics.

Chemical Composition and Antimicrobial Activity of Cone Volatile oil of Cupressus macrocarpa Hartwig from Nilgiris, India

  • Manimaran, S.;Themozhil, S.;Nanjan, M.J.;Suresh, B.
    • Natural Product Sciences
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    • v.13 no.4
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    • pp.279-282
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    • 2007
  • The aim of the present study was to investigate the various chemical components present in the cone volatile oil of Cupressus macrocarpa and also determine its antimicrobial activity. Totally 13 compounds were identified with 99.99% by GC-MS analysis. The major compounds identified were terpinene-4-ol (19.42%), dinopol (15.63%), ${\alpha}$-pinene (13.58%), and ${\beta}$-pinene (12.16%). The antimicrobial activity was carried out for the oil and a 2% cream formulation using cup plate method by measuring the zone of inhibition. The gram positive organisms used were Bacillus subtilis, Staphylococcus aureus, Bacillus megaterium, and Bacillus cogulans. The gram negative organisms used were Escherichia coli, Kleibseilla pneumonia, Pseudomonas aeruginosa and Salmonella typhi. In vitro antifungal studies were also carried out by using organisms, Candida albicans, Aspergillus flavus, Trichoderma lignorum and Cryptococcus neoformans. The standard drugs used were penicillin ($100{\mu}g/mL$), gentamycin ($100{\mu}g/mL$) and griseofulvin ($100{\mu}g/mL$) for gram positive bacteria, gram negative bacteria and fungi respectively. Both oil and cream formulation showed good activity against fungi than bacteria. This study is being reported for the first time on cone volatile oil of this plant.

The Wound Healing Potential of Lignosus rhinocerus and Other Ethno-myco Wound Healing Agents

  • Hui-Yeng Y. Yap;Mohammad Farhan Ariffeen Rosli;Soon-Hao Tan;Boon-Hong Kong;Shin-Yee Fung
    • Mycobiology
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    • v.51 no.1
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    • pp.1-15
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    • 2023
  • Wound care has become increasingly important over the years. Various synthetic products for wound care treatment have been reported to cause toxic side effects and therefore natural products are in significant demand as they have minimal side effects. The presence of bioactive compounds in medicinal mushrooms contributes to various biological activities which assist in the early inflammatory phase, keratinocyte proliferation, and its migration enhancement which are pertinent to wound rehabilitation. Lignosus rhinocerus (tiger milk mushroom) can reduce the inflammation phase in wound healing by fighting off bacterial infection and modulating pro-inflammatory cytokines expression in the early stage to avoid prolonged inflammation and tissue damage. The antibacterial, immunomodulating, and anti-inflammatory activities exhibited by most macrofungi play a key role in enhancing wound healing. Several antibacterial and antifungal compounds sourced from traditional botanicals/-products may prevent further complications and reoccurrence of injury to a wounded site. Scientific studies are actively underway to ascertain the potential use of macrofungi as a wound healing agent.

Useful Applications Decursinol Derivatives as Biochemical Fungicides (데커시놀 파생물질들의 항징균제로서의 활용)

  • Yun-Jeong Shin;Jiyoung Shin;Hyewon Jang;Hokyoung Son;Yonghoon Kwon
    • Proceedings of the Plant Resources Society of Korea Conference
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    • 2022.09a
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    • pp.30-30
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    • 2022
  • Natural products decursin and decursinol angelate were recently reported as benign fungicides for controlling rice blast. Inspired by the structural similarity of the cumarin compounds and gained hint from the skeletal motifs, we designed and prepared synthetic compounds to increase the natural product efficacy and evaluated their antifungal activities against various plant disease pathogens in vitro. Synthetically prepared compound 4 and 5 indeed suppressed the mycelial growth of B. cinerea, F. oxysporum, P. italicum, and R. quercus-mongolicae. Additionally, compound 5 effectively prevents the growth of C. coccodes and C. parasitica. Furthermore, both 4 and 5 possess better inhibitory activities on spore germination of F. oxysporum and M. oryzae than the natural product decursin. These results suggest that the effect of the lead compound for plant disease protection can be improved by tuning the structure of the original natural product and decursinol chloroacrylates 4 and 5 are candidates for the control of F. oxysporum and M. oryzae.

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Decursinol Derivatives Useful as Fungicides (데커시놀 파생물질들의 항징균제로서의 활용)

  • Yun-Jeong Shin;Jiyoung Shin;Hyewon Jang;Hokyoung Son;Yonghoon Kwon
    • Proceedings of the Plant Resources Society of Korea Conference
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    • 2022.09a
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    • pp.98-98
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    • 2022
  • Natural products decursin and decursinol angelate were recently reported as benign fungicides for controlling rice blast. Inspired by the structural similarity of the cumarin compounds and gained hint from the skeletal motifs, we designed and prepared synthetic compounds to increase the natural product efficacy and evaluated their antifungal activities against various plant disease pathogens in vitro. Synthetically prepared compound 4 and 5 indeed suppressed the mycelial growth of B. cinerea, F. oxysporum, P. italicum, and R. quercus-mongolicae. Additionally, compound 5 effectively prevents the growth of C. coccodes and C. parasitica. Furthermore, both 4 and 5 possess better inhibitory activities on spore germination of F. oxysporum and M. oryzae than the natural product decursin. These results suggest that the effect of the lead compound for plant disease protection can be improved by tuning the structure of the original natural product and decursinol chloroacrylates 4 and 5 are candidates for the control of F. oxysporum and M. oryzae.

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Inhibitory Effect Against Akt by Cyclic Dipeptides Isolated from Bacillus sp.

  • Hong, Sung-Won;Moon, Byoung-Ho;Yong, Yeon-Joong;Shin, Soon-Young;Lee, Young-Han;Lim, Yoong-Ho
    • Journal of Microbiology and Biotechnology
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    • v.18 no.4
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    • pp.682-685
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    • 2008
  • Among thirteen strains of the genus Bacillus isolated from Shrimp-jeotkal in our laboratory, a strain BA34 showing good antifungal activity against Phytophthora infestans in a previous experiment was tested for the inhibitory effect against Akt, protein kinase B. Since Akt is known to play an important role in controlling apoptosis, its inhibitors can be used as potential apoptosis-inducing agents in the treatment of cancer. Two active compounds were isolated and their structures were determined. They have similar structures, despite showing different inhibitory effects. In order to elucidate the reasons for these different effects, three-dimensional studies were carried out.

Synthesis, Reactions and Antimicrobial Activity of 2-Amino-4-(8-quinolinol-5-yl)-1-(p-tolyl)-pyrrole-3-carbonitrile

  • Abdel-Mohsen, Shawkat A.
    • Bulletin of the Korean Chemical Society
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    • v.26 no.5
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    • pp.719-728
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    • 2005
  • A novel 2-amino-4-(8-quinolinol-5-yl)-1- (p-tolyl)-pyrrole-3-cabonitrile (2) was obtained by the reaction of 2-[2-bromo-1-(8-hydroxyquinolin-5-yl)-ethylidene]-malononitrile (1) with p-toluidene. The new synthon compound (2) could be annelated to the corresponding pyrrolo[2,3-d]pyrimidines (4, 6, 7, 26-28), triazolo[1,5-c]pyrrolo[3,2-e]pyrimidines (10, 29, 30), pyrrolo[2,3-c]pyrazoles (11-15), pyrrolo[1,2-a]pyrrolo[3,2-e] pyrimidine (17) and imidazo[1,2-c]pyrrolo[3,2-e]pyrimidines (18-25) via the reaction with some reagents such as acetic anhydride, formamide, triethyl orthoformate, hydrazine hydrate, hydroxylamine, ethylenediamine, carbon disulfide and phosphorus oxychloride. Chemical and spectroscopic evidences for the structures of these compounds are presented. The antifungal and antibacterial activity of the newly synthesized comounds were evaluated.