Synthesis and Antimicrobial Activity of Carbohydrate Based Schiff Bases: Importance of Sugar Moiety

Appelt, Helmoz R.; Oliveira, Julieta Saldanha de; Santos, Roberto C.V.; Rodrigues, Oscar E. D.; Santos, Maura Z.; Heck, Elisiane Frantz; Rosa, Líria C.

doi:10.1155/2013/320892

Cited by 17 publications

(9 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For a long time, carbohydrates have been very attractive field for scientists due to their immense importance in biological systems (Appelt et al, 2013;Taylor and Drickamer, 2011;Varki et al, 2009). They are the source of the metabolic energy supply but also for the fine-tuning of cell-cell interactions and other crucial processes.…”

Section: Results and Discussion Synthesismentioning

confidence: 99%

Synthesis, Characterization and Antibacterial Susceptibility of some Benzenesulfonyl and N-Acetylsulfanilyl Derivatives of Methyl α-D-Glucopyranoside

Kawsar¹,

Uddin²,

Nishat³

et al. 2015

Current Research in Chemistry

View full text Add to dashboard Cite

A novel regioselective benzenesulphonylation and N-acetylsulfanilylation series of methyl α-D-glucopyranoside derivative (1) has been carried out by direct method and afforded the 6-O-benzenesulfonyl derivative (2) and 6-O-N-acetylsulfanilyl derivative (7) in an excellent yields. In order to obtain newer products, the 6-O-glucopyranoside derivative was further transformed to a series of 2,3,4-tri-O-acyl derivatives (3-6 and 8-11) containing a wide variety of functionalities in a single molecular framework. The structures of the newly synthesized compounds were elucidated with the aid of FTIR, 1 H-NMR spectroscopy and elemental analysis. All the synthesized compounds were also tested for their antibacterial activity against some human pathogenic bacterial microorganisms. For comparative studies, antibacterial activity of standard antibiotics, ampicillin was also carried out against these microorganisms. The study revealed that the acylated products exhibit moderate to good antimicrobial activities. It was interesting to observe that the selected compounds were more sensitive against gram-negative bacteria than that of the gram-positive bacterial strains. We carried out the antibacterial activities of the tested chemicals in vitro. In vivo screening studies of the tested compounds showing promising results will be the subject of our future investigation.

show abstract

Section: Results and Discussion Synthesismentioning

confidence: 99%

Synthesis, Characterization and Antibacterial Susceptibility of some Benzenesulfonyl and N-Acetylsulfanilyl Derivatives of Methyl α-D-Glucopyranoside

Kawsar¹,

Uddin²,

Nishat³

et al. 2015

Current Research in Chemistry

View full text Add to dashboard Cite

show abstract

“…Specifically, both gastrodin and 4-HBA were widely investigated as antioxidants and neuroprotective agents [15,16,17]. The effectiveness of certain medicinal agents, such as gastrodin, was associated with the availability of sugar unit in their structures [18,19]. However, glycosides are more prone to be metabolized by intestinal microbiota than hepatic metabolic enzymes [20].…”

Section: Discussionmentioning

confidence: 99%

Role of Intestinal Microbiota in Metabolism of Gastrodin In Vitro and In Vivo

et al. 2019

View full text Add to dashboard Cite

Alteration in the number and composition of intestinal microbiota affects the metabolism of several xenobiotics. Gastrodin, isolated from Gastrodia elata, is prone to be hydrolyzed by intestinal microbiota. In the present study, the role of intestinal microbiota in gastrodin metabolism was investigated in vitro and in vivo. Gastrodin was incubated in an anaerobic condition with intestinal contents prepared from vehicle- and antibiotics-treated rats and the disappearance of gastrodin and formation of 4-hydroxybenzyl alcohol (4-HBA) was measured by liquid chromatography coupled to mass spectroscopy (LC-MS/MS). The results showed that almost all gastrodin incubated with control intestinal contents was metabolized to its aglycone in time- and concentration-dependent manners. In contrast, much less formation of 4-HBA was detected in intestinal contents from antibiotics-treated rats. Subsequently, in vivo pharmacokinetic study revealed that the antibiotic pretreatment of rats significantly affected the metabolism of gastrodin to 4-HBA. When administered orally, gastrodin was rapidly absorbed rapidly into plasma, metabolized to 4-HBA, and disappeared from the body within six hours. Interestingly, the pharmacokinetic parameters of 4-HBA were changed remarkably in antibiotics-treated rats, compared to control rats. The results clearly indicated that the antibiotics treatment of rats suppressed the ability of intestinal microbiota to metabolize gastrodin to 4-HBA and that, thereby, the pharmacodynamic action was significantly modulated.

show abstract

“…In general, aldehydes are most commonly used in the synthesis of a large range of interesting molecules, such as imines and benzodiazepines. Many preparations of various imines by the condensation of different aldehydes with aliphatic or aromatic amines are reported in the literature [ 16 , 17 ]. This kind of molecule is known to possess significant biological properties, such as antitumor, insecticidal, antibacterial, anti-tuberculosis, antimicrobial and anticonvulsant activities [ 18 ].…”

Section: Introductionmentioning

confidence: 99%

Hemi-Synthesis of Chiral Imine, Benzimidazole and Benzodiazepines from Essential Oil of Ammodaucus leucotrichus subsp. leucotrichus

et al. 2019

View full text Add to dashboard Cite

The hemi-synthesis of chiral imine, benzimidazole and benzodiazepine structures is reported by the condensation of (S)-(−)-perillaldehyde, the major phytochemical of Ammodaucus leucotrichus subsp. leucotrichus essential oil, with different amine derivatives of 2,3-diaminomaleonitrile, o-phenylenediamine and 3-[(2-aminoaryl)amino]dimedone. The reaction proceeds in situ at ambient temperature without prior isolation of the natural (S)-(−)-perillaldehyde. Final products precipitate in the ethanolic reaction medium. 2D NMR and single-crystal X-ray diffraction studies were used to unequivocally characterize the structures in solution and in the solid state, respectively. Chiral HPLC analysis confirms the formation of unique enantiomers and diastereomeric mixtures.

show abstract

Synthesis and Antimicrobial Activity of Carbohydrate Based Schiff Bases: Importance of Sugar Moiety

Cited by 17 publications

References 21 publications

Synthesis, Characterization and Antibacterial Susceptibility of some Benzenesulfonyl and N-Acetylsulfanilyl Derivatives of Methyl α-D-Glucopyranoside

Synthesis, Characterization and Antibacterial Susceptibility of some Benzenesulfonyl and N-Acetylsulfanilyl Derivatives of Methyl α-D-Glucopyranoside

Role of Intestinal Microbiota in Metabolism of Gastrodin In Vitro and In Vivo

Hemi-Synthesis of Chiral Imine, Benzimidazole and Benzodiazepines from Essential Oil of Ammodaucus leucotrichus subsp. leucotrichus

Contact Info

Product

Resources

About