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

A furanoditerpene-enriched fraction was obtained from the fruits of Pterodon emarginatus and submitted to semipreparative high performance liquid chromatography (HPLC). Two new furanoditerpenes, 6 alpha, 19 beta-diacetoxy-7 beta, 14 beta-dihydroxyvouacapan and 6 alpha-acetoxy-7 beta, 14 beta-dihydro...

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Published inJournal of the Brazilian Chemical Society Vol. 28; no. 10; pp. 1911 - 1916
Main Authors Oliveira, Leandra A. R., Oliveira, Gerlon A. R., Lemes, Geralda F., Romao, Wanderson, Vaz, Boniek G., Albuquerque, Sergio, Goncalez, Cristiana, Liao, Luciano M., Bara, Maria Teresa F.
Format Journal Article
LanguageEnglish
Portuguese
Published SAO PAULO Soc Brasileira Quimica 01.10.2017
Sociedade Brasileira de Química
Subjects
Chemistry
CHEMISTRY, MULTIDISCIPLINARY
Physical Sciences
Science & Technology
Pterodon
PUBESCENS BENTH
furanoditerpenes
Leishmania
vouacapan
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Summary:A furanoditerpene-enriched fraction was obtained from the fruits of Pterodon emarginatus and submitted to semipreparative high performance liquid chromatography (HPLC). Two new furanoditerpenes, 6 alpha, 19 beta-diacetoxy-7 beta, 14 beta-dihydroxyvouacapan and 6 alpha-acetoxy-7 beta, 14 beta-dihydroxyvouacapan, in addition to the known compound methyl 6 alpha-acetoxy-7 beta-hydroxyvouacapan- 17 beta-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 6 alpha-acetoxy-7 beta-hydroxyvouacapan-17 beta-oate was evaluated against promastigote forms of Leishmania amazonensis and L. braziliensis, presenting the concentration which causes lysis on 50% of parasites IC50 < 30 mu g mL(-1).
ISSN:0103-5053
1678-4790
1678-4790
DOI:10.21577/0103-5053.20170029