Larvicidal activity of affinin and its derived amides from Heliopsis longipes A. Gray Blake against Anopheles albimanus and Aedes aegypti

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Highlights

  • Alkamides as natural insecticides

  • Alpha unsturation in alkamides bioactivity

  • H. longipes roots larvicidal activity against third larval stage of An. albimanus and Ae. aegypti.

  • Importance of omega conjugated double bonds for insecticidal properties against An. albimanus and Ae. aegypti.

  • Control of malaria and dengue vector transmitters

Abstract

Heliopsis longipes has been recognized as a potential source of insecticidal compounds called alkamides, which can be used to control populations of insect vector transmitters of several diseases that affect the human health. To determine the insecticidal activity of H. longipes against Anopheles albimanus and Aedes aegypti, crude extract of H. longipes roots and affinin were obtained. Catalytic reduction of affinin was performed to obtain two reduced amides, N-isobutil-2E-decenamide and N-isobutil-decanamide. Crude extract, affinin and its reduced amides were evaluated against third instar larvae of An. albimanus and Ae. aegypti. Results show that crude extract of H. longipes possess larvicidal activity against larval stage of An. albimanus and Ae. aegypti. This effect could be attributed to affinin, on which the conjugated double bonds present in the structure of the molecule are necessary to maintain larvicidal activity. This study demonstrated the potential of H. longipes to control larval stage of An. albimanus and Ae. aegypti, transmitter vectors of malaria and dengue fever, respectively.

Introduction

Mosquitoes are the most important agents in the transmission of several diseases such as encephalitis, dengue fever, filariasis and malaria which compromise the human health (Lounibos, 2002). There are approximately 3500 species of mosquitoes that belong to Culicidae family, among which find the genera Anopheles and Aedes, act as vectors of important illness worldwide (Reinert, 2001). Anopheles includes species that can transmit the four malaria-causing parasites, being Plasmodium falciparum the causal agent of the most aggressive malaria form (Bannister and Mitchell, 2003). Aedes comprises the species responsible for the transmission of arbovirus which causes both dengue and dengue hemorrhagic fever (San Martin et al., 2010). Malaria and dengue fever cause high levels of morbidity and mortality in poor countries, mainly in tropical regions of Africa, Asia and Latin America, where they inflict great economic losses and social disruption.

Strategies for reducing diseases-transmitted by vectors are focused mainly in preventive measures that control the development of insects. These involve the applications of chemical compounds such as organophosphates, including temephos, fenthion and insect growth regulators in their breeding sites (Roberts and Andre, 1994, San Martin et al., 2010). The mosquito larvae are the main developmental stage selected for the vectors control, as this strategy avoids the dispersion of adult mosquitoes and the diseases spread. Despite their effectiveness, these approaches often cause undesirable side effects that include environmental pollution and development of insecticide resistance (San Martin et al., 2010). This is now a major problem facing vector control programs in most countries where Anopheles albimanus and Aedes aegypti are showing resistance to one or more of the insecticide classes used in vector control (Cáceres et al., 2011, Lima et al., 2011, Marcombe et al., 2012). For this reason, the development of new strategies for selective mosquito larval control is necessary. Plants are an excellent alternative to search insecticides more efficient, cost effectiveness and eco-friendly. This has stimulated the investigation about natural insecticides as an alternative of control, focused on plant-derived compounds as potentially bioactive substances, some of which have showed to act as insecticides against larval stages and adult mosquitoes (Park et al., 2002, Maharaj et al., 2011).

Heliopsis longipes A. Gray Blake is a plant endemic to Central México, whose roots were described as a source of insecticide amide, the affinin (Pubmed CID: 6433895). Affinin is the main alkamide present in the H. longipes roots and considered responsible of the biological effects observed in this plant (Molina-Torres et al., 2004). Crude extracts of H. longipes roots exert paralyzing action and toxic effects against houseflies, codling moth larvae, and several leaf-eating insects (Acree et al., 1945, Jacobson, 1971). In respect to insecticidal properties against mosquitoes, it has been demonstrated that a sprayed petroleum ether extract of the H. longipes roots cause mortality on adult mosquitoes Ae. aegypti in 24 h (Jacobson, 1971). However, it has been reported that the efficiency of insecticidal activity of an extract varies depending on the development stage of the insect (Kalaivani et al., 2012). In this sense, little is known about the larvicidal activity of H. longipes and the affinin against the larval stage of mosquitoes: Ae. aegypti and An. albimanus. Only, the alkamides isolated from Piper nigrum fruits have been demonstrated to present insecticidal activity against the third instar larvae of three mosquito species; Cullens pipens pallens, Ae. aegypti and Aedes togoi (Park et al., 2002). The aim of this study was to evaluate the insecticidal effect of H. longipes against two mosquito species, An. albimanus and Ae. aegypti, in its larval stage, as possible control measure to prevent the incidence of vector-borne diseases such as malaria and dengue.

Section snippets

Plant material and extraction

H. longipes A. Gray Blake (Asteraceae) specimens were collected in Puerto de Tablas Xichú, Sierra Gorda in Guanajuato State, Central México. The plant material was authenticated by Jerzy Rzedowsky, and a voucher H. longipes JMT-IED was deposited at the Ecology Institute Pátzcuaro Michoacán. Dry roots of H. longipes (1 kg) were ground and extracted in 10 L of ethanol at room temperature during one week to obtain the alcoholic extract, which was concentrated to dryness in a rotatory evaporator

Ethanolic extract of H. longipes roots shows larvicidal activity against An. albimanus and Ae. aegypti

To determine whether H. longipes possess larvicidal effect against An. albimanus and Ae. aegypti, third instar larvae of each mosquito species were exposed to increasing concentrations of ethanolic extract of H. longipes roots during 48 h. The results showed that ethanolic extract causes larval mortality, whose effect is dependent of extract concentration. Concentrations from 7 mg/L of ethanolic extract of H. longipes roots cause approximately 100% of larval mortality for An. albimanus, and the

Conclusions

This work demonstrates that H. longipes could be a good candidate for its use in programs for control of vector transmitters of malaria and dengue because of its biocide effect against the larval stage of these mosquitoes and to the low concentrations required to carry out this effect, as this species is non-toxic to mammals as showed the use as traditional flavoring component by inhabitants of the Sierra Gorda in Guanajuato State, Central México. Ethanolic extract showed better larvicidal

Acknowledgments

We are grateful to Humberto Lanz-Mendoza and Jorge E. Ibarra for donating the eggs of mosquitoes used in this study. Authors greatly appreciate the expert technical assistance of Javier Luevano Borroel and Katia Teresa Flores Camarillo. This work was funded by grants from CONACYT to J M-T (Research grant IB 09 133309).

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