Assessment of Insecticidal Activity of Benzylisoquinoline Alkaloids from Chilean Rhamnaceae Plants against Fruit-Fly Drosophila melanogaster and the Lepidopteran Crop Pest Cydia pomonella

Abstract

The Chilean plants Discaria chacaye, Talguenea quinquenervia (Rhamnaceae), Peumus boldus (Monimiaceae), and Cryptocarya alba (Lauraceae) were evaluated against Codling moth: Cydia pomonella L. (Lepidoptera: Tortricidae) and fruit fly Drosophila melanogaster (Diptera: Drosophilidae), which is one of the most widespread and destructive primary pests of Prunus (plums, cherries, peaches, nectarines, apricots, almonds), pear, walnuts, and chestnuts, among other. Four benzylisoquinoline alkaloids (coclaurine, laurolitsine, boldine, and pukateine) were isolated from the above mentioned plant species and evaluated regarding their insecticidal activity against the codling moth and fruit fly. The results showed that these alkaloids possess acute and chronic insecticidal effects. The most relevant effect was observed at 10 µg/mL against D. melanogaster and at 50 µg/mL against C. pomonella, being the alteration of the feeding, deformations, failure in the displacement of the larvae in the feeding medium of D. melanogaster, and mortality visible effects. In addition, the docking results show that these type of alkaloids present a good interaction with octopamine and ecdysone receptor showing a possible action mechanism.

Cyclopeptide Alkaloids from Discaria chacaye (Rhamnaceae) as Result of Symbiosis with Frankia (Actinomycetales)

“…In previous work, the insecticidal effect of alkaloids with benzylisoquinoline skeletons obtained from the Chilean plants Talguenea quinquenervia , Peumus boldo , and Cryptocarya alba was studied. The results showed that these alkaloids possess acute and chronic insecticidal effects and the docking results show that these types of alkaloids present a good interaction with octopamine and ecdysone receptors showing a possible action mechanism [55] . On the other hand, cyclopeptide alkaloids have been reported to show different biological properties such as antibacterial activity, [56,57] antiplasmodial activity, [58,59] cytotoxicity, and recently as inhibitors of calmodulin‐induced activation of Ca 2+ ATPase [60] .…”

“…The bioassays according to Quiroz‐Carreño et al [55] . Artificial diet was mixed with ethanol‐diluted alkaloids extracts at concentrations of 10, 50 and 100 ug ml −1 .…”

“…The bioassays according to Quiroz-Carreño et al [55] Artificial diet was mixed with ethanol-diluted alkaloids extracts at concentrations of 10, 50 and 100 ug ml À 1 . Two negative controls were performed: one control containing only the artificial diet (control 1) and another one containing 600 μl of ethanol (control 2).…”

“…The results showed that these alkaloids possess acute and chronic insecti-cidal effects and the docking results show that these types of alkaloids present a good interaction with octopamine and ecdysone receptors showing a possible action mechanism. [55] On the other hand, cyclopeptide alkaloids have been reported to show different biological properties such as antibacterial activity, [56,57] antiplasmodial activity, [58,59] cytotoxicity, and recently as inhibitors of calmodulin-induced activation of Ca 2 + ATPase. [60] Thus, we think that insecticidal activity is a consequence of the additive effect of both types of compounds on calcium metabolism, as benzylisoquinoline alkaloids inhibit Ca 2 + transport by blocking L-type Ca 2 + channels.…”

Status and Prospects of Botanical Biopesticides in Europe and Mediterranean Countries

“…Quiroz-Carreño et al [ 118 ] reported that the benzylisoquinoline alkaloids coclaurine, laurolitsine, boldine and pukateine could interact with the heterodimer ecdysone receptor. Endocrine disturbance could also be found in non-emergent adults or deformed adults (adultoids), probably triggered by plant extracts containing phytoecdysteroids or terpenoids that act as JHAs [ 119 ].…”