Synthesis, antimicrobial evaluation and QSAR studies of p-coumaric acid derivatives

Khatkar, Anurag; Nanda, Arun; Kumar, Pradeep; Narasimhan, Balasubramanian

doi:10.1016/j.arabjc.2014.05.018

Cited by 46 publications

(27 citation statements)

References 34 publications

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“…Khatkar et al [ 110 ] evaluated the inhibitory power of amide, anilide and ester derivatives of p -coumaric acid against Staphylococcus aureus , Bacillus subtilis , Escherichia coli , Aspergillus niger and Candida albicans , to confirm the viability of their use as preservatives in cosmeceutical formulations. The results showed that all derivatives of p -coumaric acid were very effective and displayed even better activity than the control, being interesting for the replacement of some of the currently-used cosmetic preservatives.…”

Section: Hydroxycinnamic Acidsmentioning

confidence: 99%

Hydroxycinnamic Acids and Their Derivatives: Cosmeceutical Significance, Challenges and Future Perspectives, a Review

et al. 2017

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Bioactive compounds from natural sources, due to their widely-recognized benefits, have been exploited as cosmeceutical ingredients. Among them, phenolic acids emerge with a very interesting potential. In this context, this review analyzes hydroxycinnamic acids and their derivatives as multifunctional ingredients for topical application, as well as the limitations associated with their use in cosmetic formulations. Hydroxycinnamic acids and their derivatives display antioxidant, anti-collagenase, anti-inflammatory, antimicrobial and anti-tyrosinase activities, as well as ultraviolet (UV) protective effects, suggesting that they can be exploited as anti-aging and anti-inflammatory agents, preservatives and hyperpigmentation-correcting ingredients. Due to their poor stability, easy degradation and oxidation, microencapsulation techniques have been employed for topical application, preventing them from degradation and enabling a sustained release. Based on the above findings, hydroxycinnamic acids present high cosmetic potential, but studies addressing the validation of their benefits in cosmetic formulations are still scarce. Furthermore, studies dealing with skin permeation are scarcely available and need to be conducted in order to predict the topical bioavailability of these compounds after application.

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Section: Hydroxycinnamic Acidsmentioning

confidence: 99%

Hydroxycinnamic Acids and Their Derivatives: Cosmeceutical Significance, Challenges and Future Perspectives, a Review

et al. 2017

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“…The methods reported for the synthesis of p -HCAM are lengthy and tedious procedures involving combination of chemical and enzymatic steps. The methods reported by Venkateswarlu et al (2006) , Stankova et al (2009) , and Khatkar et al (2014) have resulted in low yields of coumaric acid and cinnamic acid, and their derivatives. In contrast, a simple one-step synthesis of p -HCAM could be commercially attractive, in that, it would be a rapid and cost-effective procedure.…”

Section: Discussionmentioning

confidence: 99%

“…There are a number of reports on the synthesis cinnamic acid/ coumaric acid derivatives including the synthesis of p -HCAM ( Venkateswarlu et al, 2006 ; Stankova et al, 2009 ; Khatkar et al, 2014 ). However, the procedures for p -HCAM formation employed lengthy and time-consuming multi-step methods with resultant low yields.…”

Section: Introductionmentioning

confidence: 99%

“…However, the procedures for p -HCAM formation employed lengthy and time-consuming multi-step methods with resultant low yields. There is therefore a need to develop a simple and rapid procedure for the production of p -HCAM, which has recently been shown to exhibit antimicrobial, antiviral and antioxidant activity ( Proestos et al, 2006 ; Venkateswarlu et al, 2006 ; Stankova et al, 2009 ; Terpinc et al, 2011 ; Chochkova et al, 2013 ; McCarthy et al, 2013 ; Khatkar et al, 2014 ).…”

Section: Introductionmentioning

confidence: 99%

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Rhodotorula glutinis Phenylalanine/Tyrosine Ammonia Lyase Enzyme Catalyzed Synthesis of the Methyl Ester of para-Hydroxycinnamic Acid and its Potential Antibacterial Activity

et al. 2016

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Biotransformation of L-tyrosine methyl ester (L-TM) to the methyl ester of para- hydroxycinnamic acid (p-HCAM) using Rhodotorula glutinis yeast phenylalanine/tyrosine ammonia lyase (PTAL; EC 4.3.1.26) enzyme was successfully demonstrated for the first time; progress of the reaction was followed by spectrophotometric determination at 315 nm. The following conditions were optimized for maximal formation of p-HCAM: pH (8.5), temperature (37°C), speed of agitation (50 rpm), enzyme concentration (0.080 μM), and substrate concentration (0.50 mM). Under these conditions, the yield of the reaction was ∼15% in 1 h incubation period and ∼63% after an overnight (∼18 h) incubation period. The product (p-HCAM) of the reaction of PTAL with L-TM was confirmed using Nuclear Magnetic Resonance spectroscopy (NMR). Fourier Transform Infra-Red spectroscopy (FTIR) was carried out to rule out potential hydrolysis of p-HCAM during overnight incubation. Potential antibacterial activity of p-HCAM was tested against several strains of Gram-positive and Gram-negative bacteria. This study describes a synthetically useful transformation, and could have future clinical and industrial applications.

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“…The strains were initially subjected to screening for MDR against the antibiotics: levofloxacin, ampicillin, ciprofloxacin, and methicillin. The S. aureus strain (MDRSA - QSL2040) that showed resistance to methicillin as well as other tested antibiotics ( Table 1 ) was used as a test strain and the S. aureus (ATCC 25923) was used as reference strain ( Kumar et al, 2013 ; Khatkar et al, 2014 ). These strains were cultured in the cation-adjusted Mueller–Hinton broth (CAMHB) for the minimal drug dose response against the growth and bactericidal actions.…”

Section: Methodsmentioning

confidence: 99%

Antimicrobial and Antibiofilm Potential of Acyclic Amines and Diamines against Multi-Drug Resistant Staphylococcus aureus

et al. 2017

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Multi-drug resistant Staphylococcus aureus (MDRSA) remains a great challenge despite a decade of research on antimicrobial compounds against their infections. In the present study, various acyclic amines and diamines were chemically synthesized and tested for their antimicrobial as well as antibiofilm activity against MDRSA. Among all the synthesized compounds, an acyclic diamine, (2,2′-((butane-1,4-diylbis(azanediyl)bis(methylene))diphenol) designated as ADM 3, showed better antimicrobial activity (minimum inhibitory concentration at 50 μg/mL) and antibiofilm activity (MBIC50 at 5 μg/mL). In addition, ADM 3 was capable of reducing the virulence factors expression (anti-virulence). Confocal laser scanning microscope analysis of the in vitro tested urinary catheters showed biofilm reduction as well as bacterial killing by ADM 3. On the whole, our data suggest that acyclic diamines, especially ADM 3 can be a potent lead for the further studies in alternative therapeutic approaches.

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Synthesis, antimicrobial evaluation and QSAR studies of p-coumaric acid derivatives

Cited by 46 publications

References 34 publications

Hydroxycinnamic Acids and Their Derivatives: Cosmeceutical Significance, Challenges and Future Perspectives, a Review

Hydroxycinnamic Acids and Their Derivatives: Cosmeceutical Significance, Challenges and Future Perspectives, a Review

Rhodotorula glutinis Phenylalanine/Tyrosine Ammonia Lyase Enzyme Catalyzed Synthesis of the Methyl Ester of para-Hydroxycinnamic Acid and its Potential Antibacterial Activity

Antimicrobial and Antibiofilm Potential of Acyclic Amines and Diamines against Multi-Drug Resistant Staphylococcus aureus

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