Design, synthesis and identification of novel coumaperine derivatives for inhibition of human 5-LOX: Antioxidant, pseudoperoxidase and docking studies

Sundararaman, Muthuraman; Sinha, Sanjib; Vasavi, C. S.; Waidha, Kamran; Basu, Biswarup; Munussami, Punnagai; Balamurali, M. M.; Doble, Mukesh; Kumar, Rajendran Saravana

doi:10.1016/j.bmc.2018.12.043

Cited by 20 publications

(20 citation statements)

References 43 publications

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“…The spectral data matched with structural attributes for each individual compound are presented in the Supplementary Data File. We previously confirmed the structure of CP-155, CP-209 and CP-262-F2 by single-crystal X-ray diffraction [28].…”

Section: Synthesis Of Di-and Triconjugated Coumaperine Derivativessupporting

confidence: 63%

“…Although CP is characterized by important pharmacophores such as the Michael acceptor, phenolic and amide moieties, its bioactivity has not been properly explored, probably due to its low bioavailability and long synthetic protocols. Recently, we reported a simple and a robust methodology for the synthesis of CP and its derivatives [28,29]. Following that synthetic process, CP derivatives depicted in Figures 2-4, were synthesized, and characterized for the present study.…”

Section: Discussionmentioning

confidence: 99%

“…In short, coumaperine derivatives with one alkene bond between the aromatic ring and piperidine are termed monoconjugated coumaperine derivatives and those with two and three alkene bonds are termed diand triconjugated coumaperine derivatives respectively (Figure 9). The monoconjugated coumaperine derivatives were synthesized in two steps [28,29]. Knoevenagel condensation of aldehyde and malonic acid in presence of base yields cinnamic acid derivatives.…”

Section: Synthesis Methodsmentioning

confidence: 99%

“…Demethylation was achieved with AlCl 3 at room temperature (Figure 10). Di-and triconjugated derivatives were prepared from the corresponding aldehyde and crotonic/sorbic acid according to our synthetic procedure reported earlier [28,29]. Crotonic/sorbic acid was converted to acid chloride by reacting with thionyl chloride and subsequently reacted with piperidine to obtain crotonyl/sorbyl piperidine.…”

Section: Synthesis Methodsmentioning

confidence: 99%

“…An additional natural product, Coumaperine, an amide alkaloid found in white pepper (Piper Nigrum), structurally similar to Piperine whose bioactivity has also been explored [27]. Recently, our group reported the 5-LOX inhibitory activity [28] and antiproliferative activity of coumaperine derivatives against two cancer cell lines, L428 and A549, and the inhibition of A549 cell migration [29]. However, the anti-QS activity of coumaperine and its derivatives are still unexplored.…”

Section: Introductionmentioning

confidence: 99%

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Quorum Sensing and NF-κB Inhibition of Synthetic Coumaperine Derivatives from Piper nigrum

et al. 2021

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Bacterial communication, termed Quorum Sensing (QS), is a promising target for virulence attenuation and the treatment of bacterial infections. Infections cause inflammation, a process regulated by a number of cellular factors, including the transcription Nuclear Factor kappa B (NF-κB); this factor is found to be upregulated in many inflammatory diseases, including those induced by bacterial infection. In this study, we tested 32 synthetic derivatives of coumaperine (CP), a known natural compound found in pepper (Piper nigrum), for Quorum Sensing Inhibition (QSI) and NF-κB inhibitory activities. Of the compounds tested, seven were found to have high QSI activity, three inhibited bacterial growth and five inhibited NF-κB. In addition, some of the CP compounds were active in more than one test. For example, compounds CP-286, CP-215 and CP-158 were not cytotoxic, inhibited NF-κB activation and QS but did not show antibacterial activity. CP-154 inhibited QS, decreased NF-κB activation and inhibited bacterial growth. Our results indicate that these synthetic molecules may provide a basis for further development of novel therapeutic agents against bacterial infections.

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Section: Synthesis Of Di-and Triconjugated Coumaperine Derivativessupporting

confidence: 63%

Section: Discussionmentioning

confidence: 99%

Section: Synthesis Methodsmentioning

confidence: 99%

Section: Synthesis Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Quorum Sensing and NF-κB Inhibition of Synthetic Coumaperine Derivatives from Piper nigrum

et al. 2021

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Expedient discovery of novel oxime ester derivatives of piperine/piperine analogs as potent pesticide candidates and their mode of action against Tetranychus cinnabarinus Boisduval

Wen

et al. 2023

Pest Management Science

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BACKGROUNDNowadays, pest infestation and resistance have appeared as a consequence of repeated and extensive use of pesticides. Thus, development of new effective pesticide candidates in crop protection is highly desirable. Herein, a series of new piperine derivatives containing oxime ester scaffolds were regioselectively and stereoselectively prepared as pesticidal agents.RESULTSSteric configurations of compounds 2, 5z and 13e were definitively determined by single‐crystal X‐ray diffraction. Against Tetranychus cinnabarinus, notably, compounds 5f [median lethal concentration (LC50) = 0.14 mg mL−1] and 5v (LC50 = 0.13 mg mL−1) showed >107‐fold greater acaricidal activity than piperine (LC50 = 15.02 mg mL−1), which were comparable to the commercial acaricide spirodiclofen. Against Aphis citricola, compound 5d (LD50 = 19.12 ng aphid−1) exhibited 6.1‐fold more potent aphicidal activity than piperine (LD50 = 116.06 ng aphid−1). Additionally, through scanning electron microscopy, the toxicology study suggested that the acaricidal activity of piperine derivatives may be related to damage of the cuticle layer crest of T. cinnabarinus.CONCLUSIONThe structure–activity relationships suggested that 3,4‐dioxymethylene of piperine was crucial for its acaricidal activity; and introduction of a certain length of aliphatic chain at the C‐2 position was beneficial to the aphicidal and acaricidal activities. Compounds 5f and 5v are potential leads for further structural modification as acaricidal agents. © 2023 Society of Chemical Industry.

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Pseudomonas aeruginosa quorum sensing and biofilm attenuation by a di-hydroxy derivative of piperlongumine (PL-18)

Schlichter Kadosh,

Muthuraman,

Nisaa

et al. 2024

Biofilm

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Design, synthesis and identification of novel coumaperine derivatives for inhibition of human 5-LOX: Antioxidant, pseudoperoxidase and docking studies

Cited by 20 publications

References 43 publications

Quorum Sensing and NF-κB Inhibition of Synthetic Coumaperine Derivatives from Piper nigrum

Quorum Sensing and NF-κB Inhibition of Synthetic Coumaperine Derivatives from Piper nigrum

Expedient discovery of novel oxime ester derivatives of piperine/piperine analogs as potent pesticide candidates and their mode of action against Tetranychus cinnabarinus Boisduval

Pseudomonas aeruginosa quorum sensing and biofilm attenuation by a di-hydroxy derivative of piperlongumine (PL-18)

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