In vitro biological activity of essential oils and isolated furanosesquiterpenes from the neglected vegetable Smyrnium olusatrum L. (Apiaceae) Luana Quassinti a , Massimo Bramucci a , Giulio Lupidi a , Luciano Barboni b , Massimo Ricciutelli c , Gianni Sagratini a , Fabrizio Papa a , Giovanni Caprioli a , Dezemona Petrelli d , Luca A. Vitali a , Sauro Vittori a , Filippo Maggi a,⇑ a School of Pharmacy, University of Camerino, Italy b School of Science and Technology, Chemistry Division, University of Camerino, Italy c HPLC–MS Laboratory, University of Camerino, Italy d School of Biosciences and Biotechnology, University of Camerino, Italy article info Article history: Received 17 September 2012 Received in revised form 27 October 2012 Accepted 12 November 2012 Available online 27 November 2012 Keywords: Smyrnium olusatrum Essential oils Furanosesquiterpenes Tumor cell lines Antioxidant activity abstract Smyrnium olusatrum, better known as Alexanders or wild celery, is a biennal herb used in cuisine for many centuries by Romans in many dishes, where it has now been replaced by celery. In order to provide additional evidences so that this forgotten vegetable can be reconsidered in the human diet, as well as in pharmaceutics, the essential oils obtained from different parts and its main isolated furanosesquiterp- enes were in vitro biologically assayed for antiproliferative activity on human tumor cell lines by MTT assay, for antioxidant potential by DPPH, ABTS and FRAP assays, and for antimicrobial activity by the agar disc diffusion method. The essential oils showed cytotoxic effects on tested human tumor cell lines, related to the furanosesquiterpenoid content; the IC 50 values on colon carcinoma, glioblastoma, and breast adenocarcinoma cells were 8.51, 13.35, and 14.81 lg/ml, respectively. Isofuranodiene and 1b-acet- oxyfuranoeudesm-4(15)-ene resulted the most active constituents. The essential oils possessed also rad- ical scavenging activity. Ó 2012 Elsevier Ltd. All rights reserved. 1. Introduction Smyrnium olusatrum L. (Apiaceae), better known as Alexanders or wild celery, is a celery-scented biennal herb with black ripe fruits, widespread in countries bordering the Mediterranean basin to its northern limit in Scotland and Ireland, where it is fully naturalised after its introduction during Roman age. Its name comes from the old city of Alexandria in Egypt, the site of origin of the plant, from which it has been brought to Europe (Randall, 2003). The species was extensively cultivated in antiquity, and, as mentioned by PLINIO, the stems were eaten by the Romans (Mattioli, 1984). This is today attested by the Alexanders popula- tions still growing at Fori Imperiali in Rome. Thus, Alexanders was cultivated all over European kitchen gardens for many centu- ries because of its culinary properties owing to the particular myrrh-like aroma. Its use as a vegetable was abandoned in the Middle Ages when it was replaced by celery (Apium graveolens L.) (Mölleken, Sinnwell, & Kubeczka, 1998a). Besides culinary uses, Alexanders was also used as medicinal plant during Greek and Roman ages; the leaves were regarded as antiscorbutic, the fruits as stomachic and antiasthmatic, and the juice of the root as aromatic, appetite stimulant, diuretic and laxa- tive (Fournier, 1947). Unlike common celery, whose aroma is mainly given by phta- lides, Alexanders volatile fraction is characterised by furanoger- macrane-type sesquiterpenes. Notably, these molecules isolated also from Rhizoma curcumae were subjected to many scientific investigations in recent years (Lu et al., 2012). In our previous study, the chemical compositions of essential oils from different parts of Alexanders were analysed by GC-FID, GC–MS and HPLC-DAD highlighting a high content of furanoses- quiterpenoids, with isofuranodiene (synonym: furanodiene) (19.5–45.8%), curzerene (2.6–10.5%), furanoeremophil-1-one (15.2–33.1%) and 1b-acetoxyfuranoeudesm-4(15)-ene (0.3–31.0%) as the main representatives of this fraction (Maggi et al., 2012) (Table 1). Not many investigations were made on Alexanders regarding its biological activity as well as on that of its main constituents. Nota- bly, only the antimicrobial and the antifungal activity of the essen- tial oils were reported, with inhibition on the growth of Bacillus rhurinziensis, Staphylococcus aureus, Cryptococcus neoformans, Aspergillus niger and dermatophyte strains (Daroui-Mokaddem et al., 2010; Marongiu et al., 2012). 0308-8146/$ - see front matter Ó 2012 Elsevier Ltd. All rights reserved. http://dx.doi.org/10.1016/j.foodchem.2012.11.075 ⇑ Corresponding author. Tel.: +39 0737404506; fax: +39 0737404508. E-mail address: filippo.maggi@unicam.it (F. Maggi). Food Chemistry 138 (2013) 808–813 Contents lists available at SciVerse ScienceDirect Food Chemistry journal homepage: www.elsevier.com/locate/foodchem