Antifungals and acetylcholinesterase inhibitors from the stem bark of Croton heliotropiifolius

•C. heliotropiifolius EtOH extract showed antifungal and AChE inhibitory activities.•Dereplication and localization of active constituents was performed by HPLC-UV-MS.•Targeted isolation of the constituents enabled the identification of 9 compounds.•3 diterpenes showed anticandidal activity on TLC b...

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Bibliographic Details
Published in:	Phytochemistry letters Vol. 10; pp. lxxxviii - xciii
Main Authors:	Queiroz, M.M.F., Queiroz, E.F., Zeraik, M.L., Marti, G., Favre-Godal, Q., Simões-Pires, C., Marcourt, L., Carrupt, P.A., Cuendet, M., Paulo, M.Q., Bolzani, V.S., Wolfender, J.L.
Format:	Journal Article
Language:	English
Published:	Elsevier Ltd 01-12-2014
Subjects:	Acetylcholinesterase inhibition Antifungal Candida albicans Croton Croton heliotropiifolius Euphorbiaceae HPLC-PDA-ESI-MS HPLC-TOF-HRMS Acetylcholinesterase inhibition Candida albicans HPLC-TOF-HRMS HPLC-PDA-ESI-MS Antifungal Croton heliotropiifolius
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Summary:	•C. heliotropiifolius EtOH extract showed antifungal and AChE inhibitory activities.•Dereplication and localization of active constituents was performed by HPLC-UV-MS.•Targeted isolation of the constituents enabled the identification of 9 compounds.•3 diterpenes showed anticandidal activity on TLC bioautography assay.•5 alkaloids present an inhibition of acetylcholinesterase activity. The ethanolic extract of the stem bark of Croton heliotropiifolius Kunth (Euphorbiaceae) showed significant in vitro inhibition of acetylcholinesterase using a dilution spectrophotometric assay and antifungal activity against Candida albicans with a thin layer chromatography (TLC) bioautographic assay. In order to isolate the active compounds, bioassay-guided fractionation was undertaken using HPLC to localize the active compounds. Different zones of the HPLC-UV chromatogram were linked to acetylcholinesterase inhibition or to antifungal activities. In parallel to this HPLC-based activity profiling, HPLC-PDA-ESI-MS and HPLC-TOF-HRMS were used for the early identification of some of the compounds present. The targeted isolation of the active compounds was performed by medium pressure liquid chromatography (MPLC-UV) and further semi-preparative HPLC. Using this approach, nine compounds were isolated, one of them being a new indole alkaloid derivative. The structures of the isolated compounds were elucidated by spectroscopic methods including UV, NMR, MS and HRMS.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1874-3900 1876-7486
DOI:	10.1016/j.phytol.2014.08.013