Abstract

Dragon’s blood (Sangre de drago), a viscous red sap derived from Croton lechleri Muell-Arg (Euphorbiaceae), is extensively used by indigenous cultures of the Amazonian basin for its wound healing properties. The aim of this study was to identify the minor secondary metabolites and test the antioxidant activity of this sustance. A bio-guided fractionation of the n-hexane, chloroform, n-butanol, and aqueous extracts led to the isolation of 15 compounds: three megastigmanes, four flavan-3-ols, three phenylpropanoids, three lignans, a clerodane, and the alkaloid taspine. In addition to these known molecules, six compounds were isolated and identified for the first time in the latex: blumenol B, blumenol C, 4,5-dihydroblumenol A, erythro-guaiacyl-glyceryl-β-O-4’-dihydroconiferyl ether, 2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]-propane-1,3-diol and floribundic acid glucoside. Combinations of spectroscopic methods (1H-, 13C- NMR and 2D-NMR experiments), ESI-MS, and literature comparisons were used for compound identification. In vitro antioxidant activities were assessed by DPPH, total antioxidant capacity and lipid peroxidation assays. Flavan-3-ols derivatives (as major phenolic compounds in the latex) exhibited the highest antioxidant activity.

Highlights

  • Croton lechleri (Muell-Arg) (Euphorbiaceae), is a tree which grows in the low mountainous areas of the Peruvian Andean regions, as well as in Colombia, Ecuador and Bolivia and it is known for its therapeutic properties

  • Chromatographic separation by Sephadex® LH-20 was followed by Droplet counter-current chromatography (DCCC), which is a key step in the purification of complex mixtures of natural compounds

  • We have revealed for the first time the presence in C. lechleri latex, of minor secondary metabolites as megastigmane, lignan, and clerodane derivatives

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Summary

Introduction

Croton lechleri (Muell-Arg) (Euphorbiaceae), is a tree which grows in the low mountainous areas of the Peruvian Andean regions, as well as in Colombia, Ecuador and Bolivia and it is known for its therapeutic properties. The blood-red latex or sap is a common household remedy in Peru and in other Latin American countries, where indigenous tribes use it internally and externally to stop bleeding, help heal wounds, and treat intestinal ailments [1]. The results of in vitro and in vivo studies support the use the viscous latex, which exhibits antioxidant [2, 3] antiviral [4] and anti-inflammatory [5] activities, in addition to being efficacious in the treatment of different types of diarrhoea, including cholera [6]. The oral administration of a compound, termed SP-303, isolated from the bark latex by Ubillas et al [4], leads to positive results in the treatment of traveller’s diarrhoeas [7]. Since free radicals may participate in the early stages of carcinogenesis, recently antioxidant activity was evaluated against the oxidative damages induced by apomorfine in Saccaromices cerevisiae [16]

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