Larvicidal Activity of Isobutylamides Identified in Piper nigrum Fruits against Three Mosquito Species

Abstract

The insecticidal activity of materials derived from the fruits of Piper nigrum against third instar larvae of Culex pipiens pallens, Aedes aegypti, and A. togoi was examined and compared with that of commercially available piperine, a known insecticidal compound from Piper species. The biologically active constituents of P. nigrum fruits were characterized as the isobutylamide alkaloids pellitorine, guineensine, pipercide, and retrofractamide A by spectroscopic analysis. Retrofractamide A was isolated from P. nigrum fruits as a new insecticidal principle. On the basis of 48-h LC(50) values, the compound most toxic to C. pipiens pallens larvae was pipercide (0.004 ppm) followed by retrofractamide A (0.028 ppm), guineensine (0.17 ppm), and pellitorine (0.86 ppm). Piperine (3.21 ppm) was least toxic. Against A. aegypti larvae, larvicidal activity was more pronounced in retrofractamide A (0.039 ppm) than in pipercide (0.1 ppm), guineensine (0.89 ppm), and pellitorine (0.92 ppm). Piperine (5.1 ppm) was relatively ineffective. Against A. togoi larvae, retrofractamide A (0.01 ppm) was much more effective, compared with pipercide (0.26 ppm), pellitorine (0.71 ppm), and guineensine (0.75 ppm). Again, very low activity was observed with piperine (4.6 ppm). Structure-activity relationships indicate that the N-isobutylamine moiety might play a crucial role in the larvicidal activity, but the methylenedioxyphenyl moiety does not appear essential for toxicity. Naturally occurring Piper fruit-derived compounds merit further study as potential mosquito larval control agents or as lead compounds.

A biodegradable device for the controlled release of Piper nigrum (Piperaceae) standardized extract to control Aedes aegypti (Diptera, Culicidae) larvae

“…This difference was likely associated with differences in the methods used to obtain the extract (21) (31) (32) . The lack of standardization hampers the comparison between different piperine content rates; however, Ik and colleagues have found LC 50 values of 3.21ppm for isolated piperine (33) , which is similar to the LC50 determined for PnE containing only 60% piperine. These fi ndings indicate that PnE activity cannot be attributed solely to piperine but also to other isobutylamide compounds found in this species such as retrofractamide A and pellitorine, piperine derivatives that have shown LC 50 values of 0.028ppm and 0.86, respectively (34) .…”

The combined action of phytolarvicides for the control of dengue fever vector, Aedes aegypti

“…For example, because piperine is an amide that lacks the isobutyl substituent. the previous studies have suggested the presence of several other bioactive compounds in P. nigrum; such compounds could include the isobutylamides retrofractamide A, pipercide, guineensine and pellitorine (Park et al, 2002).…”

“…Acetogenins act as pesticides on several arthopodes what is based on a specifi c mechanism that blocks energy generation in the mitochondrial complex I. Another species, Piper nigrum L., Piperaceae, which is commonly used as black pepper, contains a series of amides also possessing insecticidal potential such as piperine, pipercide, guineensine, pellitorine, pipgulzarine and pipzorine (Park et al, 2002;Siddiqui et al, 2004;Siddiqui et al, 2003). Ilex paraguariensis A.…”

Naturally Occurring Plant Compounds with Larvicidal Activity AgainstAedes aegypti

“…Este conjunto de substâncias pode ser dividido em dois: amidas que possuem a parte relativa ao ácido carboxílico originada da rota biossintética mista (ácido chiquímico/policetídica, 1 a 6) 52,53,54 e as amidas que têm esta parte da molécula originada diretamente de ácidos graxos (substâncias 7 a 9). 51,52,54 Estas rotas coocorrem, visto que ambos os tipos foram obtidos da mesma planta. O nitrogênio da amida, nestes compostos, é substituído pelo grupo isobutila (2, 4 a 8), além de piperidina (1 e 3) e por um homólogo de isobutila (9).…”