Abstract
Leishmaniasis is a complex of diseases caused by protozoa of the genus Leishmania and affects millions of people around the world. Several species of plants are used by traditional communities for the treatment of this disease, among which is Carapa guianensis Aubl. (Meliaceae), popularly known as andiroba. The objective of the present work was to conduct a chemical study of C. guianensis seed oil and its limonoid-rich fractions, with the aim of identifying its secondary metabolites, particularly the limonoids, in addition to investigating its anti-Leishmania potential. The chemical analyses of the C. guianensis seed oil and fractions were obtained by electrospray ionization mass spectrometry (ESI-MS). The cytotoxic activity was tested against peritoneal macrophages, and antileishmanial activity was evaluated against promastigotes and intracellular amastigotes of Leishmania amazonensis. All the C. guianensis seed oil samples analyzed exhibited the same pattern of fatty acids, while the limonoids 7-deacetoxy-7-hydroxygedunin, deacetyldihydrogedunin, deoxygedunin, andirobin, gedunin, 11β-hydroxygedunin, 17-glycolyldeoxygedunin, 6α-acetoxygedunin, and 6α,11β-diacetoxygedunin were identified in the limonoid-rich fractions of the oil. The C. guianensis seed oil did not exhibit antileishmanial activity, and cytotoxicity was higher than 1000 μg/mL. Three limonoid-rich oil fractions demonstrated activity against promastigotes (IC50 of 10.53±0.050, 25.3±0.057, and 56.9±0.043μg/mL) and intracellular amastigotes (IC50 of 27.31±0.091, 78.42±0.086, and 352.2±0.145 μg/mL) of L. amazonensis, as well as cytotoxicity against peritoneal macrophages (CC50 of 78.55±1.406, 139.0±1.523, and 607.7±1.217 μg/mL). The anti-Leishmania activity of the limonoid-rich fractions of C. guianensis can be attributed to the limonoids 11β-hydroxygedunin and 6α,11β-diacetoxygedunin detected in the chemical analysis.
Highlights
Leishmaniasis is characterized as zoonotic disease in which humans can be involved in a secondary or accidental manner
As a result of the medicinal properties already reported for this species, the common treatments used for leishmaniasis in the Amazon region, and the reports in literature, the present study proposed to evaluate the chemical compounds present in the oil and limonoid-rich fractions of C. guianensis seed oil and to verify which compounds are involved in their anti-Leishmania activity
The five samples of C. guianensis seed oil had their phytochemical profiles compared by mass spectrometry using the direct infusion technique (ESI/MS)
Summary
Leishmaniasis is characterized as zoonotic disease in which humans can be involved in a secondary or accidental manner. They are noncontagious, infectious-parasitic diseases, caused by several species of protozoa of the genus Leishmania. Leishmaniasis is classified as neglected disease, and the treatment recommended by the World Health Organization still has many side effects, making patient adherence difficult and contributing to increased cases of resistance to several strains of Leishmania. For this reason, new therapeutic alternatives have been sought, including the use of natural products [2] New therapeutic alternatives have been sought, including the use of natural products [2].
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