Abstract

Esenbeckia leiocarpa Engl. (Rutaceae), popularly known as guarantã, goiabeira, is a native tree from Brazil. Bioactivity-guided fractionation of the ethanol stems extract afforded the isolation of six alkaloids: leiokinine A, leptomerine, kokusaginine, skimmianine, maculine and flindersiamine. All isolated compounds were tested for acetyl cholinesterase inhibition, in vitro and displayed anticholinesterasic activity. The alkaloid leptomerine showed the highest activity (IC50 = 2.5 μM), similar to that of the reference compound galanthamine (IC50 = 1.7 μM). The results showed for the first time the presence of alkaloids leptomerine and skimmianine in E. leiocarpa (Engl.) with potent anticholinesterasic activity.

Highlights

  • IntroductionChemical studies of Esenbeckia spp. showed that they synthesize a variety of secondary metabolites, quinolinic, quinolonic and indolic alkaloids and furocoumarins, and these compounds were considered chemical markers of this genus [2,3,4]

  • The genus Esenbeckia comprises 30 species distributed in Tropical America [1]

  • Previous studies on E. leiocarpa have been reported in the literature, and various compounds have been isolated from it, such as the alkaloids kokusaginine, flindersiamine, maculine, dictamnine, 4methoxy-2-(3 ́-pentyl)quinoline, 1,4-dihydro-1-methyl-2-(3 ́-pentyl)quinolin-4-one, leiokinine A and leiokinine B, twelve indole derivatives, three lignans, one coumarin, two amides and the methyl 4isoprenyloxy-trans-cinnamate [3,6,7]

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Summary

Introduction

Chemical studies of Esenbeckia spp. showed that they synthesize a variety of secondary metabolites, quinolinic, quinolonic and indolic alkaloids and furocoumarins, and these compounds were considered chemical markers of this genus [2,3,4]. Previous studies on E. leiocarpa have been reported in the literature, and various compounds have been isolated from it, such as the alkaloids kokusaginine, flindersiamine, maculine, dictamnine, 4methoxy-2-(3 ́-pentyl)quinoline, 1,4-dihydro-1-methyl-2-(3 ́-pentyl)quinolin-4-one, leiokinine A and leiokinine B, twelve indole derivatives, three lignans, one coumarin, two amides and the methyl 4isoprenyloxy-trans-cinnamate [3,6,7]. In a screening of 58 extracts from native Brazilian plants, the ethanolic crude extract of the stems of Esenbeckia leiocarpa showed a strong acetylcholinesterase inhibition and was chosen for bioassay-guided fractionation in order to isolate the biologically active compounds and evaluate the acetylcholinesterase inhibition of these compounds

Results and Discussion
Chromatographic profile of alkaloid fraction
Anticholinesterasic activity of alkaloids
Plant material
Extraction and isolation
General methods for compounds identification
Anticholinesterasic assay
Conclusions
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