Isolation and Structural Characterization of Two New Furanoditerpenes from Pterodon emarginatus (Fabaceae)

Leandra Oliveira,Gerlon Oliveira,Sérgio Albuquerque,Boniek Vaz,Wanderson Romão,Geralda Lemes,Luciano Lião,Maria Bara,Cristiana Gonçalez

doi:10.21577/0103-5053.20170029

Abstract

A furanoditerpene-enriched fraction was obtained from the fruits of Pterodon emarginatus and submitted to semipreparative high performance liquid chromatography (HPLC). Two new furanoditerpenes, 6α,19β-diacetoxy-7β,14β-dihydroxyvouacapan and 6α-acetoxy-7β,14β-dihydroxyvouacapan, in addition to the known compound methyl 6α-acetoxy-7β-hydroxyvouacapan-17β-oate were obtained. Compound structures were determined by 1D and 2D nuclear magnetic resonance (NMR) experiments and electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry (ESI-FTICR-MS). The major compound methyl 6α-acetoxy-7β-hydroxyvouacapan-17β-oate was evaluated against promastigote forms of Leishmania amazonensis and L. braziliensis, presenting the concentration which causes lysis on 50% of parasites IC50 < 30 µg mL-1.

Highlights

According to the website The Plant List,[1] Pterodon (Fabaceae) comprises two native Brazilian species, popularly known as “sucupira-branca” or “faveiro”: Pterodon abruptus (Moric.) Benth. and P. emarginatus Vogel
Vouacapan furanoditerpenes were obtained from an enriched sample (DHF) by semipreparative reversed phase (RP)-high performance liquid chromatography (HPLC)
The C14 stereochemistry in is agreement with that proposed for two furanoditerpenes voucapanes containing methyl and hydroxyl groups attached on C14.12 The proposed structure is in agreement with 6α,19β‐diacetoxy-7β,14β‐dihydroxyvouacapan (1)

Summary

Introduction

According to the website The Plant List,[1] Pterodon (Fabaceae) comprises two native Brazilian species, popularly known as “sucupira-branca” or “faveiro”: Pterodon abruptus (Moric.) Benth. (synonym: P. apparicioi) and P. emarginatus Vogel (synonyms: P. polygalaeflorus, P. polygaliflorus and P. pubescens). Mass spectra were acquired and processed using data analysis software (Bruker Daltonics, Bremen, Germany). Fractions amounting to shaded peaks 1, 2, and 3-4 (Figure 1) were collected from three injections, which produced white solids following concentration and freezedrying steps.

Results

Conclusion