Chemical composition of essential oils fromAnnona vepretorumMart. andAnnona squamosaL. (Annonaceae) leaves and their antimalarial and trypanocidal activities

Abstract

Here, we describe the trypanocidal and antimalarial activities from essential oils extracted from Annona vepretorum (AVOE) and Annona squamosa (ASOE) (Annonaceae) leaves. The essential oils were obtained by hydrodistillation and analyzed by gas chromatography-mass spectrometry (GC-MS) and GC-flame ionization detection (GC-FID). A total of twenty-one compounds were identified in AVOE and twenty-three in ASOE. The sesquiterpenes are more abundant in the both essential oils. ASOE contained significant quantities of (E)-caryophyllene (27.4%), germacrene D (17.1%) and bicyclogermacrene (10.8%). The major compounds in AVOE were bicyclogermacrene (39.0%), spathulenol (14.0%) and α-phellandrene (11.5%). The essential oils demonstrated potent trypanocidal and antimalarial activities with values of IC 50 lower than 20 μg/mL, and a strong inhibition of the proliferation of amastigotes, the clinically relevant forms of Trypanosoma cruzi. In addition, through ultrastructural studies and flow cytometry analysis with trypomastigotes of T. cruzi, we identified significant ultrastructural alterations induced by the essential oils, especially in the cell membrane and mitochondria, which ultimately results in necrotic parasite death.

Characterization of the Leaf Essential Oil Composition of Annona squamosa L. from Foothills of North India

“…Noteworthy observation is the fact that compounds such as carvone, diacetyl, cadina-1,4-diene, β-cedrene, β-gurjunene, bicyclogermacrene, which were the major constituents in previous studies [15,16,18,23,24] could not be detected in this investigation. Moreover, germacrene D, a major constituent of various previous studies on A. squamosa leaf oil [12,15,18] was present in only trace amount in the examined oil. This may be attributed to several factors such as climatic condition, season, and age of the plant, genotype, and processing procedures.…”

“…Major constituents of the Brazilian oil were (E)-caryophyllene (27.4%), germacrene D (17.1%), bicyclogermacrene (10.8%), (Z)-caryophyllene (7.3%), β-elemene (6.2%) and α-humulene (5.7%) [12]. Two distinct compositions were described from Egypt.…”

“…To compare the composition of the investigated A. squamosa essential oil with earlier reported oil compositions [12,15,16,18,23,24], twenty-four selected components (amount ≥ 5.0%) of different oils were subjected to the hierarchical cluster analysis. The derived dendrogram clearly showed dissimilarity based on the percentages of (Figure 4).…”

“…A fraction of total root alkaloids is reported to be antihypertensive, antispasmodic, antihistaminic and a bronchodilator [11]. The leaf essential oil of the plant has been demonstrated potent trypanocidal and antimalarial activities [12].…”

“…The leaf essential oil from Benin possessed isocaryophyllene, camphene, β-caryophyllene, epi-α-cadinol and epi-α-muurolol as major constituents [14]. The leaf essential oil rich in (E)-caryophyllene, germacrene D, bicyclogermacrene, (Z)-caryophyllene, β-elemene and α-humulene is reported from Brazil [12]. Major constituents of the leaf essential oil of A. squamosa from north Indian plains are (E)-caryophyllene, germacrene D, bicyclogermacrene, β-elemene, γ-cadinene, α-muurolol and aromadendrene [15].…”