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Antifungal Compounds Isolated from Smyrnium olusatrum L. Essential Oil, Growing Wild in Cephalonia, Greece. Chemical Analysis and Structure Elucidation

Gerasimia Tsasi, Marina Soković, Ana Cirić, Effimia Eriotou, Eleni Sakadani, Yiannis Samaras and Helen Skaltsa

Department of Pharmacognosy and Chemistry of Natural Products, School of Pharmacy, University of Athens, Panepistimiopolis, Zografou, 15771 Athens, Greece

Department of Plant Physiology, Mycological Laboratory, Institute for Biological Research, University of Belgrade, Bulevar despota Stefana 142, 11 000 Belgrade, Serbia

Department of Organic Farming and Food Technology, Technological Educational Institute (T.E.I.) of Ionian Islands, Vergotis’ Ave, 28100 Argostoli, Cephalonia, Greece

Abstract: The essential oils (EOs) from the leaves and the flowers of Smyrnium olusatrum L. , growing wild in the island of Cephalonia (Greece), were analyzed by GC-FID and GC-MS. Fifty nine constituents, which accounted for 90.3% (fl) and 97.1% (lvs) of the oils, were identified. Furanodiene, g ermacrone and furanoeremophil-1-one were the major constituents in both essential oils; they were also isolated from the flowers essential oil and identified using spectroscopic methods, ie. 1D and 2D NMR, GC-MS . In addition b -myrcene ( 11.7%) and b -phellandrene (5.2%) were main constituents in the essential oil of the leaves. The essential oils and the pure isolates were evaluated for antifungal activity against Aspergillus fumigatus , A. versicolor, A. ochraceus, A. niger, Trichoderma viride, Penicillium funiculosum, P. ochrochloron, P. verucosum var. cyclopium by using the microdilution method and proved to possess significant antifungal effect. Among them, (+) furanoeremophil-1-one was particularly active with MIC values in the range of 0.0008-0.125 mg/mL and MFC values of 0.025-0.050 mg/mL and proved more effective than the commercial mycotics ketoconazole and bifonazole used as positive controls.

Keywords: Smyrnium olusatrum ; essential oil; isolation; (+) furanoeremophil-1-one; furanodiene; (-) germacrone, antifungal activity . © 2015 ACG Publications. All rights reserved.