scholarly journals Macrooxazoles A–D, New 2,5-Disubstituted Oxazole-4-Carboxylic Acid Derivatives from the Plant Pathogenic Fungus Phoma macrostoma

Molecules ◽  
2020 ◽  
Vol 25 (23) ◽  
pp. 5497
Author(s):  
Blondelle Matio Kemkuignou ◽  
Laura Treiber ◽  
Haoxuan Zeng ◽  
Hedda Schrey ◽  
Rainer Schobert ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
High Resolution Mass Spectrometry ◽  
Pathogenic Fungus ◽  
Antimicrobial Activities ◽  
Moderate Activity ◽  
Fungal Metabolites ◽  
Plant Pathogenic Fungus ◽  
Tetramic Acids ◽  
Bacteria And Fungi ◽  
New Compounds

In our ongoing search for new bioactive fungal metabolites, four previously undescribed oxazole carboxylic acid derivatives (1–4) for which we proposed the trivial names macrooxazoles A–D together with two known tetramic acids (5–6) were isolated from the plant pathogenic fungus Phoma macrostoma. Their structures were elucidated based on high-resolution mass spectrometry (HR-MS) and nuclear magnetic resonance (NMR) spectroscopy. The hitherto unclear structure of macrocidin Z (6) was also confirmed by its first total synthesis. The isolated compounds were evaluated for their antimicrobial activities against a panel of bacteria and fungi. Cytotoxic and anti-biofilm activities of the isolates are also reported herein. The new compound 3 exhibited weak-to-moderate antimicrobial activity as well as the known macrocidins 5 and 6. Only the mixture of compounds 2 and 4 (ratio 1:2) showed weak cytotoxic activity against the tested cancer cell lines with an IC50 of 23 µg/mL. Moreover, the new compounds 2 and 3, as well as the known compounds 5 and 6, interfered with the biofilm formation of Staphylococcus aureus, inhibiting 65%, 75%, 79%, and 76% of biofilm at 250 µg/mL, respectively. Compounds 5 and 6 also exhibited moderate activity against S. aureus preformed biofilm with the highest inhibition percentage of 75% and 73% at 250 µg/mL, respectively.

scholarly journals Synthesis and DFT Study of Newly Schiff Base and Fused Heterocyclic Compounds as Antibacterial Agent

2019 ◽  
Vol 16 ◽  
pp. 5395-5403
Author(s):  
Sameh Rizk ◽  
Ismail M. Awheda ◽  
Fathi A. Smida
Keyword(s):  
Schiff Base ◽  
Antibacterial Agent ◽  
Heterocyclic Compounds ◽  
Excellent Result ◽  
Antimicrobial Activities ◽  
Rate Of Reaction ◽  
Bacteria And Fungi ◽  
Bridgehead Nitrogen ◽  
Nitrogen Nucleophiles ◽  
New Compounds

Treatment of 2,3-di-(4-chlorophenyl) oxirane-2,3-dicarbonitriles(1) with nitrogen nucleophiles, e.g. N2H4, NH2OH afforded pyrazole 2, 1.2oxazole 3 derivatives respectively The 3-amino pyrazole-4-one derivatives 2 can be used as a key starting materials to synthesize some important Schiff base 4 and fused heterocyclic compounds e.g. Imidazolo-[4,5-c]pyrazole 5, Pyrazolo[3,4-e]1,2,4-triazine 6, pyrazol[1,2-a] 1,3,5-triazine 7, 8 and 9. The electromeric effect of the halogen atom in the aryl moieties can be controlled upon the rate of reaction and the yield of the product. The structures of synthesized new compounds were characterized by spectral data and screened for their antimicrobial activities against various bacteria and fungi strains. The heterocyclic compounds 7, 8 and 9 that contained bridgehead nitrogen gave an excellent result. 

scholarly journals Synthesis of new pyrazolone and pyrazole-based adamantyl chalcones and antimicrobial activity

2020 ◽  
Vol 40 (9) ◽  
Author(s):  
Rawan Al-Saheb ◽  
Sami Makharza ◽  
Feras Al-battah ◽  
Rajab Abu-El-Halawa ◽  
Tawfeq Kaimari ◽  
...  
Keyword(s):  
High Dose ◽  
Moderate Activity ◽  
Dependent Manner ◽  
H Nmr ◽  
Ft Ir ◽  
Bacteria And Fungi ◽  
New Compounds ◽  
Dose Dependent ◽  
Ft Ir Spectroscopy ◽  
C Nmr

Abstract Chalcones and their derivatives are becoming increasingly popular due to their various pharmacological effects. Chalcone molecules may be extracted from natural resources, entirely synthesised, or biosynthesised by modifying the natural ones. In the present study, five pyrazole-based adamantyl heterocyclic compounds were synthesised by condensation of 1-adamantyl chalcone with substituted phenylhydrazine. The products were characterised by using ¹H NMR, ¹³C NMR and FT-IR spectroscopy. The microbiological activity of these compounds was investigated against bacteria and fungi. The new compounds showed good to moderate activity against the microbial species used for screening. All developed molecules showed antibacterial activity against Gram-negative and Gram-positive. These molecules showed antifungal activities against Fusarium oxysporum fungus and in a dose-dependent manner, apart from RS-1 molecules which showed compromised antifungal activity and even at a high dose.

scholarly journals Isolation and characterization of new phenolic siderophores with antimicrobial properties from Pseudomonas sp. UIAU-6B

2021 ◽  
Vol 17 ◽  
pp. 2390-2398
Author(s):  
Emmanuel Tope Oluwabusola ◽  
Olusoji O Adebisi ◽  
Fernando Reyes ◽  
Kojo S Acquah ◽  
Mercedes De La Cruz ◽  
...  
Keyword(s):  
High Resolution Mass Spectrometry ◽  
Antimicrobial Properties ◽  
2D Nmr ◽  
Culture Broth ◽  
Moderate Activity ◽  
North Central ◽  
Isolation And Characterization ◽  
Antimicrobial Evaluation ◽  
New Compounds

Five new phenolic siderophores 1–5 were isolated from the organic extract of a culture broth in a modified SGG medium of Pseudomonas sp. UIAU-6B, obtained from sediments collected from the Oyun river in North Central Nigeria. The structure of the new compounds, pseudomonin A–C (1–3) and pseudomobactin A and B (4 and 5) isolated alongside two known compounds, pseudomonine (6) and salicylic acid (7), were elucidated based on high-resolution mass spectrometry, 1D and 2D NMR analyses. The absolute configuration of the threonine residue in compounds 1–5 was determined by Marfey analysis. The antimicrobial evaluation of compound 4 exhibited the most potent activity against vancomycin-sensitive Enterococcus faecium VS144754, followed by 3 and 5, with MIC values ranging from 8 to 32 µg/mL. Compounds 2 and 3 exhibited moderate activity against Mycobacterium tuberculosis H37Rv, with MIC values of 7.8 and 15.6 µg/mL, respectively. Plausible biosynthetic hypotheses toward the new compounds 1–5 were proposed.

scholarly journals Bacillamidins A–G from a Marine-Derived Bacillus pumilus

Marine Drugs ◽  
2018 ◽  
Vol 16 (9) ◽  
pp. 326
Author(s):  
Si-Yu Zhou ◽  
Yi-Jie Hu ◽  
Fan-Cheng Meng ◽  
Shen-Yue Qu ◽  
Rui Wang ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Bacillus Pumilus ◽  
High Resolution Mass Spectrometry ◽  
Antimicrobial Activities ◽  
Nmr Data ◽  
Extensive Analysis ◽  
New Compounds ◽  
Long Chain ◽  
Resolution Mass

Seven long-chain amides, including five previously undescribed bacillamidins A–E (1–5) and two previously reported synthetic analogs, bacillamidins F (6) and G (7), were isolated from extracts of the marine-derived Bacillus pumilus strain RJA1515. The structures of the new compounds were established by extensive analysis of 1D and 2D nuclear magnetic resonance (NMR) data as well as high resolution mass spectrometry (HRMS), and the absolute configurations of the stereogenic carbons of 1–4 were established by comparison of the calculated and the experimental electronic circular dichroism (ECD) spectra. The cytotoxic and antimicrobial activities of 1–7 were evaluated.

Novel ammonium phosphinates containing peptide moiety: Synthesis, structure, and in vitro antimicrobial activity

2012 ◽  
Vol 66 (8) ◽  
Author(s):  
Khodayar Gholivand ◽  
Niloufar Dorosti
Keyword(s):  
Antimicrobial Activity ◽  
Compound Viii ◽  
Moderate Activity ◽  
Gram Negative Bacteria ◽  
Orthorhombic System ◽  
Peptide Moiety ◽  
Excess Amount ◽  
Bacteria And Fungi ◽  
New Compounds

AbstractFive new ammonium phosphinates with formula [XC6H4NHC(O)NHP(O)YO]−[H2Y]+ (Y = N(CH3)(CH2C6H5), X = H (IV), CH3 (V), NO2 (VI); Y = NH(CH2C6H5), X = H (VII), NO2 (VIII)) were synthesised by the reaction of N-arylureidophoshoryl dichlorides with N-methylbenzylamine or benzylamine in the presence of an excess amount of the corresponding amine. All new compounds were characterised by NMR and IR spectral data and elemental analysis. Their antimicrobial activity was tested against some Gram-positive and Gram-negative bacteria and fungi. Compounds IV and VIII exhibited moderate activity in vitro against Bacillus subtilis. In addition, compound VIII moderately inhibited Pseudomonas aeruginosa. The crystal structure of benzylmethylammonium(3-phenylureido)(benzylmethylamino)phosphinate (IV) was also determined. This compound crystallises in the orthorhombic system.

scholarly journals Secondary Metabolites with Antimicrobial Activities from Chamaecyparis obtusa var. formosana

Molecules ◽  
2022 ◽  
Vol 27 (2) ◽  
pp. 429
Author(s):  
Ming-Der Wu ◽  
Ming-Jen Cheng ◽  
Jih-Jung Chen ◽  
Nanthaphong Khamthong ◽  
Wen-Wei Lin ◽  
...  
Keyword(s):  
Spectroscopic Analysis ◽  
High Resolution Mass Spectrometry ◽  
Chamaecyparis Obtusa ◽  
Antibacterial Activities ◽  
Antimicrobial Activities ◽  
The Past ◽  
Nmr Data ◽  
The Mean ◽  
New Compounds ◽  
First Time

Seven new compounds, including one dimer novel skeleton, chamaecyformosanin A (1); three diterpenes, chamaecyformosanins B–D (2-4); one sesquiterpene, chamaecyformosanin E (5); and two monoterpenes, chamaecyformosanins F and G (6 and 7) were isolated from the methanol extract of the bark of Chamaecyparis obtusa var. formosana. Their structures were established by the mean of spectroscopic analysis and the comparison of NMR data with those of known analogues. Their structures were elucidated on the basis of physicochemical evidence, in-depth NMR spectroscopic analysis, and high-resolution mass spectrometry. Furthermore, the isolated compounds were subjected to an evaluation of their antimicrobial activity. Metabolites 1, 3, and 4 present antibacterial activities. It is worth mentioning that the chemical composition of the bark of C. obtusa var. formosana has never been studied in the past. This is the first time the barks from C. obtusa var. formosana were studied and two new skeleton compounds, 1 and 7, were obtained.

scholarly journals Microwave Synthesis, Characterization, and Antimicrobial Activity of Some Novel Isatin Derivatives

2015 ◽  
Vol 2015 ◽  
pp. 1-8 ◽  
Author(s):  
Ayman El-Faham ◽  
Wael N. Hozzein ◽  
Mohammad A. M. Wadaan ◽  
Sherine N. Khattab ◽  
Hazem A. Ghabbour ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Carboxylic Acid ◽  
Fungal Pathogens ◽  
Biologically Active ◽  
Moderate Activity ◽  
Gram Positive ◽  
X Ray Crystallography ◽  
Gram Positive Bacteria ◽  
Bacteria And Fungi ◽  
Isatin Derivatives

Three series of isatin derivatives [3-hydrazino, 3-thiosemicarbazino, and 3-imino carboxylic acid derivatives] were synthesized employing microwave irradiation. The prepared compounds were characterized by FT-IR, NMR, elemental analysis, and X-ray crystallography for derivatives5b. The synthesized compounds were screened for antimicrobial activity against selected bacteria and fungi. The results revealed that theN-alkyl isatin derivatives were biologically active with different spectrums activity. Most of the 3-hydrazino and 3-thiosemicarbazino isatin derivatives were biologically inactive and generally the active derivatives showed weak to moderate activity mainly against Gram-positive bacteria. The imino isatin carboxylic acid derivatives (2-[4-(1-benzyl-5-bromo-2-oxoindolin-3-ylideneamino) phenyl]acetic acid,5d) showed promising activity against all tested Gram-positive bacteria and against fungal pathogens.

Antimalarials from an unidentified plant pathogenic fungus isolated from Torreya taxifolia

Planta Medica ◽  
2012 ◽  
Vol 78 (11) ◽  
Author(s):  
M Kumarihamy ◽  
S Khan ◽  
D Ferreira ◽  
E Croom Jr ◽  
S Duke ◽  
...  
Keyword(s):  
Pathogenic Fungus ◽  
Plant Pathogenic Fungus

Biological Evaluation of 1, 4-Disubstituted 1,2,3-Triazole Derivatives as Plant Pathogenic Fungus Inhibitors

2011 ◽  
Vol 4 (8) ◽  
pp. 685-688
Author(s):  
H.Ighachane H.Ighachane ◽  
◽  
H.El ayadi H.El ayadi ◽  
My.H.Sedra My.H.Sedra ◽  
H.B.Lazrek H.B.Lazrek
Keyword(s):  
Pathogenic Fungus ◽  
Biological Evaluation ◽  
Triazole Derivatives ◽  
Plant Pathogenic Fungus

Synthesis and Antimicrobial activities of Some Polyphenol compounds by Nano ZnO-TBAB as a Heterogeneous Catalytic Media

2020 ◽  
Vol 17 ◽  
Author(s):  
Rahele Bargebid ◽  
Ali Khalafi-Nezhad ◽  
Kamiar Zomorodian ◽  
Leila Zamani ◽  
Ali Ahmadinejad ◽  
...  
Keyword(s):  
Antibacterial Activities ◽  
Antimicrobial Activities ◽  
Reusable Catalyst ◽  
Nano Zno ◽  
Antifungal Activities ◽  
Chemical Structures ◽  
Heterogeneous Catalytic ◽  
Solvent Free Conditions ◽  
New Compounds ◽  
Derivatives Of

Introduction: Mannich reaction is a typical example of a three-component condensation reaction and the chemistry of Mannich bases has been the matter of search by researchers. Here an efficient procedure for the synthesis of some new Mannich derivatives of simple phenols is described. Methods: In this procedure a microwave-assisted and solvent less condensation were done between different phenols, secondary amines and paraformaldehyde. The reactions proceed in the presence of catalytic amount of nano ZnO and tetrabutylammonium bromide (TBAB) in excellent yields. 10 new compounds were synthesized (A1-A10). Chemical structures of all new compounds were confirmed by different spectroscopic methods. We optimized the chemical reactions in different conditions. Optimization reactions were done in the presence of different mineral oxides, different amount of TBAB and also different solvents. Nano ZnO and TBAB in catalytic amounts and solvent free conditions were the best conditions. All the synthesized compounds were screened for their antimicrobial activities. Antifungal and antibacterial activities of the synthesized compounds were evaluated against some Candida, filaments fungi, gram positive and gram negative bacteria by broth micro dilution method as recommended by CLSI. Results: The result showed that compounds A2, A3 and A4 against most of the tested Candida species and compounds A5 and A7 against C. parapsilosis and C. tropicalis, exhibited considerable antifungal activities. Also Compounds A8 and A10 showed desirable antifungal activities against C. neoformance and C. parapsilosis, respectively. The antibacterial activities of the synthesized compounds were also evaluated. Compounds A6 - A10 against E. Fecalis and compounds A5, A7, A9 and A10 against P. aeruginosa showed desirable antibacterial activities. Discussion: We have synthesized some new Mannich adducts of poly-hydroxyl phenols in the presence of nano-ZnO as a reusable catalyst, with the hope of discovering new lead compounds serving as potent antimicrobial agents. The advantages of this method are generality, high yields with short reaction times, simplicity, low cost and matching with green chemistry protocols. The antimicriobial studies of Mannich derivatives of phenols showed desirable results in vitro.

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