Isolation and Chemotaxonomic Implications of Tenelloside, a Novel Unusual C-Glycosyl Flavanone from Phyllanthus tenellus Roxb. in Tenerife Island DOI Creative Commons
Antonio Francioso,

Ignacio Antonio Jiménez Díaz,

Carolina P. Reyes

et al.

Separations, Journal Year: 2023, Volume and Issue: 11(1), P. 15 - 15

Published: Dec. 31, 2023

Phyllanthus is a large genus of the Euphorbiaceae family, which has been widely used in traditional medicine. The current study reports isolation an unusual C-glycosyl flavonoid, named tenelloside, from tenellus Roxb., non-endemic plant present Canary Islands. chemical structure this secondary metabolite was established employing combined spectrometric and spectroscopic techniques, including 1D 2D NMR experiments mass spectrometry. absolute stereochemical configuration determined via comparison experimental calculated electronic circular dichroism spectra. In our previous work, another C-glycosylated bioactive product isolated species, suggesting that class compounds can be produced genus-specific manner different geographic regions. This work represents important report for direct future studies on biological chemotaxonomic potential products genus.

Language: Английский

Activity-based protein profiling in drug/pesticide discovery: Recent advances in target identification of antibacterial compounds DOI
Kunlun Chen, Ling Zhang, Yue Ding

et al.

Bioorganic Chemistry, Journal Year: 2024, Volume and Issue: 151, P. 107655 - 107655

Published: July 17, 2024

Language: Английский

Citations

4
Novel D-Ribofuranosyl Tetrazoles: Synthesis, Characterization, In Vitro Antimicrobial Activity, and Computational Studies DOI Creative Commons

Riham Sghyar,

Mouad Lahyaoui,

Yassine Rhazi

et al.

ACS Omega, Journal Year: 2025, Volume and Issue: 10(2), P. 2116 - 2129

Published: Jan. 7, 2025

The goal of this study was to synthesize and evaluate new antimicrobial compounds. We specifically focused on the development 2,5-disubstituted tetrazole derivatives containing O-methyl-2,3-O-isopropylidene-(D)-ribofuranoside groups through N-alkylation reactions. synthesized compounds were characterized using 1H 13C nuclear magnetic resonance (NMR) spectroscopy. Their antibacterial activity tested against Pseudomonas aeruginosa, Escherichia coli, Streptococcus fasciens, Staphylococcus aureus. Density functional theory (DFT) applied examine electronic properties, including highest occupied molecular orbital (HOMO)–least unoccupied (LUMO) gap, hardness, softness, density states (DOS), electrostatic potential. Additionally, crystal structure modeling protein 7AZ5 performed binding affinities hydrophobic interactions hydrogen bonding. Molecular dynamics simulations carried out for 100 ns OPLS_2005 force field re investigate stability 3c 5c into site. Root-mean-square deviation (RMSD), root mean square fluctuation (RMSF), intermolecular analysis showed that these two may gave relative Several N-ribofuranosyl displayed a strong activity. Compounds 1c particularly effective, with minimum inhibitory concentration (MIC) 15.06 μM 13.37 μM, respectively, E. coli S. aureus both surpassing efficacy chloramphenicol (19.34 μM) ampicillin (28.62 μM). These also energies in modeling, indicating DNA polymerase sliding clamp coli. show promise as potent agents notable chemical favorable profiles. findings suggest serve valuable leads drugs.

Language: Английский

Citations

0
Stereoselective Synthesis of Aromatic Polyketide Prealnumycin DOI Open Access
Kei Kitamura,

Tomoteru Yamasaki,

Hiroto Kaku

et al.

Chemical and Pharmaceutical Bulletin, Journal Year: 2025, Volume and Issue: 73(2), P. 86 - 93

Published: Feb. 5, 2025

Prealnumycin (1), a benzoisochromanequinone compound, produces biologically active exfoliamycin or alnumycin through hybridization with D-ribose oxidation. We report herein concise and stereoselective synthesis of 1. The anionic annulation phthalide 5 enone 6, prepared via transition metal-catalyzed enantioselective route, afforded tricyclic lactone 4. This intermediate then underwent highly diastereoselective introduction an n-propyl group nucleophilic addition followed by silane reduction. Subsequent regioselective arene oxidation 18 using cerium(IV) ammonium nitrate (CAN) naphthoquinone 2. Further manipulations, including acidic deprotection elimination, yielded prealnumycin in 8 steps.

Language: Английский

Citations

0
Biotechnological synthesis of nucleoside analogs: recent progress and perspectives DOI Creative Commons
Qiang Wang, Kewei Chen, Yujue Wang

et al.

Green Synthesis and Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: May 1, 2025

Language: Английский

Citations

0
Phosphorylation-condensation cascade for biocatalytic synthesis of C-nucleosides DOI Creative Commons

Andrej Ribar,

Martin Pfeiffer, Bernd Nidetzky

et al.

Chem Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 101127 - 101127

Published: Oct. 1, 2024

Language: Английский

Citations

1
Expression, purification and characterization of non-heme iron-dependent mono-oxygenase OzmD in oxazinomycin biosynthesis DOI
Daan Ren, Yu‐Hsuan Lee, Hung‐wen Liu

et al.

Methods in enzymology on CD-ROM/Methods in enzymology, Journal Year: 2024, Volume and Issue: unknown, P. 113 - 142

Published: Jan. 1, 2024

Language: Английский

Citations

0
The chemistry of Formycin biosynthesis DOI Creative Commons
Nigel G. J. Richards, James H. Naismith

Frontiers in Chemical Biology, Journal Year: 2024, Volume and Issue: 3

Published: July 12, 2024

Remarkable progress has been made to elucidate the structural and mechanistic enzymology of biosynthetic pathways that give rise naturally occurring C-nucleosides. These compounds are generally cytotoxic exhibit interesting antiviral, antibiotic anti-parasitic activity. Here we review current knowledge concerning formycin biosynthesis highlight deficiencies in our understanding key chemical transformations pathway.

Language: Английский

Citations

0
Isolation and Chemotaxonomic Implications of Tenelloside, a Novel Unusual C-Glycosyl Flavanone from Phyllanthus tenellus Roxb. in Tenerife Island DOI Creative Commons
Antonio Francioso,

Ignacio Antonio Jiménez Díaz,

Carolina P. Reyes

et al.

Separations, Journal Year: 2023, Volume and Issue: 11(1), P. 15 - 15

Published: Dec. 31, 2023

Phyllanthus is a large genus of the Euphorbiaceae family, which has been widely used in traditional medicine. The current study reports isolation an unusual C-glycosyl flavonoid, named tenelloside, from tenellus Roxb., non-endemic plant present Canary Islands. chemical structure this secondary metabolite was established employing combined spectrometric and spectroscopic techniques, including 1D 2D NMR experiments mass spectrometry. absolute stereochemical configuration determined via comparison experimental calculated electronic circular dichroism spectra. In our previous work, another C-glycosylated bioactive product isolated species, suggesting that class compounds can be produced genus-specific manner different geographic regions. This work represents important report for direct future studies on biological chemotaxonomic potential products genus.

Language: Английский

Citations

0