Insecticidal activity of Piper aduncum oil: variation in dillapiole content and chemical and toxicological stability during storage

Abstract

The insecticidal effect of the essential oil of Piper aduncum (EOPA), and of its constituent dillapiole [1-allyl-2,3-dimethoxy-4,5-(methylenedioxy) benzene] in particular, is well documented in the literature and can be associated with its interference with the enzymatic detoxification in arthropods. However, no data exist on the range of dillapiole content associated with insecticidal activity, which is necessary to establish reliable dose-activity parameters for a formulated product. The oil composition can also change during storage after distillation, mainly due to environmental factors such as light incidence, atmospheric oxygen and temperature, which can be deleterious to oil quality. In this study, EOPA subjected to different storage conditions over four years and its rectified fractions were submitted to bioassays to evaluate their insecticidal effect by topical contact and residual contact against Spodoptera frugiperda. Our objectives were to determine the relationship between dillapiole content and the insecticidal activity of EOPA, and to evaluate its chemical and toxicological properties over time under different conditions. Our results showed that EOPA was stable with respect to the dillapiole content and the toxicological effect against S. frugiperda under different storage conditions for four years. The overall chemical composition of the EOPA did not vary significantly among storage conditions. EOPA with dillapiole content ranging between 68% and 100% showed greater insecticidal toxicity by residual and topical contact against S. frugiperda larvae.

Development, validation and application of a gas chromatography method for the determination of dillapiole from Piper aduncum essential oil in skin permeation samples

“…DIL has also been reported in P. aduncum essential oil in concentrations ranging from 52 to 73% (Andrade & Faria, 2010). Finally, two recent studies reported a dillapiole content of 74–78% (Fazolin et al, 2022) or in the range 53–91% (Ferreira et al, 2022). In this sense, the DIL found in EOPA in this study is in agreement with the reports in the literature.…”

“…One of the most important substances in genus Piper is dillapiole (DIL; Figure 1), a phenylpropanoid found in abundance in Piper aduncum L. (30–90%; Arze et al, 2008; Fazolin et al, 2022; Ferreira et al, 2022; Gottlieb et al, 1981; Jantan et al, 1994; Rali et al, 2007; Smith & Kassim, 1979; Vila et al, 2005), which has been successfully tested as a fungicide (Ferreira et al, 2016; Guerrini et al, 2009; Lobato et al, 2007), insecticide (Volpe et al, 2016), bactericide (Brazão et al, 2014; Monzote et al, 2017) and anti‐inflammatory (Parise‐Filho et al, 2011). Despite the various activities reported for P. aduncum essential oil and its main compound DIL, and the traditional topical use (Taher et al, 2020) there is no report to date about the development and validation of an analytical and bioanalytical methodology in order to quantify DIL from the essential oil of P. aduncum (EOPA) and in biological matrices, such as skin samples.…”

Exploring the Efficacy of Four Apiaceae Essential Oils against Nine Stored-Product Pests in Wheat Protection

“…As with other monoterpenoids, γ -terpinene has been reported to be a competitive inhibitor of acetylcholinesterase (AChE) [ 125 ], but the exact mechanism of action is yet to be defined. The pesticidal action of C. maritimum EO could be ascribed to the action of γ -terpinene, as well as to the synergistic activity of this compound with β -phellandrene, dillapiole, thymol methyl ether, and p -cymene (14.7, 12.0, 11.2, and 10.1% of the total composition, respectively), all of which have demonstrated insecticidal and pesticidal properties [ 126 , 127 , 128 ].…”

UHPLC-HRMS/MS Chemical Fingerprinting of the Bioactive Partition from Cultivated Piper aduncum L.

“…The biological and pharmacological activities associated with P. aduncum extracts are extensive and noteworthy. Pharmacological studies have demonstrated the effectiveness of these extracts in antibacterial, antifungal, antiprotozoal, larvicidal, insecticidal, molluscicidal, cytotoxic, antidepressant, and anxiolytic activities [4][5][6]9,15]. The wide range of biological activities described highlights the multifunctionality of this species and warrants exploration to isolate specific bioactive small molecules.…”