The larvicidal activity of natural inspired piperine-based dienehydrazides against Culex pipiens

Tantawy, A. O.; Farag, Shaimaa M.; Hegazy, Lamees; Jiang, Hong; Wang, Man‐Qun

doi:10.1016/j.bioorg.2019.103464

Cited by 23 publications

(18 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The natural product piperine (Figure , I ) and its derivatives have been reported to have medicinal properties, including antitumor, , antimicrobial, , and anti-inflammatory activities. , In addition, these compounds exhibit good insecticidal properties (Figure ) against various agricultural pests, such as Ascia monuste orseis Latr (Lepidoptera: Pieridae), Brevicoryne brassicae L (Homoptera: Aphididae), Mythimna separata Walker (Oriental armyworm), , Plutella xylostella Linnaeus (diamondback moth), and Culex pipiens (Diptera) . Stemofoline (Figure , II ), isolated from the roots of Stemona collinsiae Craib, , exhibits a variety of agriculture-related activities as follows: toxicity and growth inhibition toward the neonate larvae of Spodoptera littoralis, , insecticidal and antifeedant activities against diamondback moth larvae, and oral toxicity toward silkworm larvae (B.…”

Section: Introductionmentioning

confidence: 99%

A Piperine-Based Scaffold as a Novel Starting Point to Develop Inhibitors against the Potent Molecular Target OfChtI

Han

et al. 2021

J. Agric. Food Chem.

View full text Add to dashboard Cite

The insect chitinase Of ChtI from the agricultural pest Ostrinia furnacalis (Asian corn borer) is a promising target for green insecticide design. Of ChtI is a critical chitinolytic enzyme for the cuticular chitin degradation at the stage of molting. In this study, piperine, a natural amide compound isolated from black pepper, Piper nigrum L., was discovered for the first time to have inhibitory activity toward Of ChtI. The compound−enzyme interaction was presumed to take place between the piperine benzo [d][1,3] dioxole skeleton and subsite −1 of the substrate-binding pocket of Of ChtI. Hence, on the basis of the deduced inhibitory mechanism and crystal structure of the substrate-binding cavity of Of ChtI, compounds 5a−f were designed and synthesized by introducing a butenolide scaffold into the lead compound piperine. The enzymatic activity assay indicated that compounds 5a−f (K i = 1.03−2.04 μM) exhibited approximately 40−80-fold higher inhibitory activity than the lead compound piperine (I) (K i = 81.45 μM) toward Of ChtI. The inhibitory mechanism of the piperonyl butenolide compounds was elucidated by molecular dynamics, which demonstrated that the introduced butenolide skeleton improved the binding affinity to Of ChtI. Moreover, the in vivo activity assay indicated that these compounds also displayed moderate insecticidal activity toward O. furnacalis. This work introduces the natural product piperine as a starting point for the development of novel insecticides targeting Of ChtI.

show abstract

Section: Introductionmentioning

confidence: 99%

A Piperine-Based Scaffold as a Novel Starting Point to Develop Inhibitors against the Potent Molecular Target OfChtI

Han

et al. 2021

J. Agric. Food Chem.

View full text Add to dashboard Cite

show abstract

“…The spectroscopic analysis matched with those previously our work published 35 and included in appendix A.…”

Section: Methodsmentioning

confidence: 65%

“…According to Scheme 1 , piperic acid 2 was formed by hydrolyzing piperine (1) with alcoholic KOH, 34 followed by a reaction with oxalyl chloride in the presence of DMF as a catalyst to yield piperic acid chloride 3. 35 Carbonyl compounds were treated with hydrazine hydrate to yield the corresponding hydrazones 4a–h, which were then reacted with piperic acid chloride to yield the corresponding compounds 5a–h. The synthesized compounds were elucidated by 1 H, 13 C and 19 F NMR.…”

Section: Resultsmentioning

confidence: 99%

“…Compounds 2 and 3 were prepared according to our previous research work 35 and the experimental details are recorded in Appendix A.…”

Section: Methodsmentioning

confidence: 99%

“…General details and crystallographic data (Table S1): see ESI † and Appendix A. prepared according to our previous research work 35 and the experimental details are recorded in Appendix A. 4.1.2.…”

Section: Chemistrymentioning

confidence: 99%

See 2 more Smart Citations

Structure-based design, synthesis, and biological evaluation of novel piperine–resveratrol hybrids as antiproliferative agents targeting SIRT-2

et al. 2021

Self Cite

View full text Add to dashboard Cite

show abstract

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

View full text Add to dashboard Cite

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.

show abstract

The larvicidal activity of natural inspired piperine-based dienehydrazides against Culex pipiens

Cited by 23 publications

References 34 publications

A Piperine-Based Scaffold as a Novel Starting Point to Develop Inhibitors against the Potent Molecular Target OfChtI

A Piperine-Based Scaffold as a Novel Starting Point to Develop Inhibitors against the Potent Molecular Target OfChtI

Structure-based design, synthesis, and biological evaluation of novel piperine–resveratrol hybrids as antiproliferative agents targeting SIRT-2

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

Contact Info

Product

Resources

About