A New Source of (R)-Limonene and Rotundifolone from Leaves of Lippia pedunculosa (Verbenaceae) and their Trypanocidal Properties

Abstract

Investigation by GC-FID and GC-MS of the essential oil (LPOE) from the leaves of Lippia pedunculosa revealed, as the major compounds, the monoterpenes rotundifolone (71.7%) and (R)-limonene (21.8%). These two compounds and the minor constituent piperitenone (1.2%) were also isolated from the leaves and identified by spectrometric analysis. LPOE and isolated compounds were evaluated for their trypanocidal activity against epimastigote and trypomastigote forms of Trypanosoma cruzi. Significant results with IC 50 values lower than 34.0 μg.mL-1 were observed against these forms of T. cruzi for LPOE and isolated compounds. Rotundifolone was the most active compound with an IC 50 lower than 10.0 μg.mL-1 for both forms of T. cruzi. The effects of LPOE and isolated compounds were also evaluated in cultures of macrophages infected with T. cruzi. Treatment with (R)-limonene and rotundifolone caused a moderate reduction in the percentage of macrophages infected by T. cruzi and in the number of intracellular parasites at concentrations non-toxic to macrophages.

Mentha suaveolens Ehrh. (Lamiaceae) Essential Oil and Its Main Constituent Piperitenone Oxide: Biological Activities and Chemistry

“…According to recent investigations, the plant species Lippia pedunculosa (Verbenaceae) may be considered as the new important source of PO since it is a predominant constituent (≈72%) in its essential oil [118]. For sure, PO is not characteristic of the genus Lippia , but some of the other species also contains it as a minor or significant constituent [119].…”

“…PO was the most active compound. The effects of the oil and isolated compounds on the intracellular form of the parasite were also evaluated in cultures of macrophages infected with T. cruzi , but the treatment with ( R )-limonene and PO caused a moderate reduction in the percentage of macrophages [118].…”

Trypanocidal Essential Oils: A Review

“…, Lippia citriodora Kunth., Lippia dulcis Trev., Lippia micromera Schauer and Lippia origanoides Kunth. [ 31 ] showed in vitro trypanocidal activity against T. cruzi , with L. pedunculosa at concentrations of 11.3 and 15.1 µg/mL, L. sidoides at 10.3 and 28.9 µg/mL, L. alba at 5.5 and 12.5 µg/mL, L. citriodora at 24.3 and 75 µg/mL, L. dulcis at 32.8 and 51.7 µg/mL, and L. micromera at 50.6 and 60.7 µg/mL. Finally, L. origanoides obtained values of 9.9 and 50.5 µg/mL.…”

“…During apoptosis, there are alterations such as cytoplasmic blebbing, cell volume reduction, loss of mitochondrial membrane potential, condensation of nuclear chromatin, and DNA fragmentation [ 71 ]. Such characteristics were observed from the essential oils of Cinnamodendron dinisii [ 14 ], Siparuna guianensis [ 14 ], Cinnamomum verum [ 19 ], Lippia dulcis [ 30 ], Achyrocline satureioides [ 61 , 62 ], Lippia sidoides [ 13 ], Lippia origanoides [ 13 , 30 , 65 ], Chenopodium ambrosioides [ 13 ], Justicia pectorales [ 13 ], Lippia citriodora [ 30 ], Lippia pedunculosa [ 31 ] and Lippia alba [ 30 ]. However, due to the large number of components and potential synergistic and/or antagonistic interactions between them, it is likely that in addition to membranes, essential oils can also act against other cellular targets ( Figure 2 ).…”

Response of Orchid Cut Flowers as Affected by Floral Preservatives on the Postharvest Quality

“…It is a volatile monoterpene used as a flavoring agent and a preservative . The ubiquitous colorless and 10 carbon compound is found in numerous other plant genera such as Lippia, Artemisia(sagewort) and Cannabis also (Fraternale et al, 2015;Gómez et al, 2013;Gurgel do Vale et al, 2002;Khan et al, 2012;Menezes et al, 2014;Russo, 2011;Zhou et al, 2019). Limonene has been found to show herbicide properties and acts as an attraction for pollinators (Erasto & Viljoen, 2008).…”