Natural Product Research Formerly Natural Product Letters ISSN: 1478-6419 (Print) 1478-6427 (Online) Journal homepage: http://www.tandfonline.com/loi/gnpl20 Chemical composition of the essential oil from the aerial parts of Ononis reclinata L. (Fabaceae) grown wild in Sicily Simona Casiglia, Maurizio Bruno & Felice Senatore To cite this article: Simona Casiglia, Maurizio Bruno & Felice Senatore (2017) Chemical composition of the essential oil from the aerial parts of Ononis reclinata L. (Fabaceae) grown wild in Sicily, Natural Product Research, 31:1, 7-15, DOI: 10.1080/14786419.2016.1205054 To link to this article: http://dx.doi.org/10.1080/14786419.2016.1205054 Published online: 05 Jul 2016. Submit your article to this journal Article views: 119 View related articles View Crossmark data Full Terms & Conditions of access and use can be found at http://www.tandfonline.com/action/journalInformation?journalCode=gnpl20 Download by: [Jordan Univ. of Science & Tech] Date: 20 April 2017, At: 15:38 NATURAL PRODUCT RESEARCH, 2017 VOL. 31, NO. 1, 7–15 http://dx.doi.org/10.1080/14786419.2016.1205054 Chemical composition of the essential oil from the aerial parts of Ononis reclinata L. (Fabaceae) grown wild in Sicily Simona Casigliaa, Maurizio Brunoa and Felice Senatoreb aDepartment STEBICEF, University of Palermo, Palermo, Italy; bDepartment of Pharmacy, University of Naples “Federico II”, Naples, Italy ABSTRACT ARTICLE HISTORY In the present study, the chemical composition of the essential oil from Received 4 April 2016 aerial parts of Ononis reclinata L., a species not previously investigated, Accepted 2 June 2016 collected in Sicily was evaluated by GC and Gas chromatography- KEYWORDS Mass spectrometry. The main components of O. reclinata were Ononis reclinata; Fabaceae; menthone (43.6%), isopimpinellin (38.4%) and pulegone (11.2%). volatile components; The comparison with other studied oils of genus Ononis showed a menthone; isopimpinellin; peculiar and characteristic profile. pulegone 1. Introduction Genus Ononis L., commonly known as the ‘restharrow’, is a member of the temperate her- baceous belonging to family Fabaceae, subfamily Papilionoideae, tribe Trifolieae (APG III 2009). Its species are annual or perennial herbs, subshrubs or rarely shrubs, usually pubescent with eglandular or glandular, sticky hairs. The leaves are mostly trifoliate (sometimes unifo- liate), with the leaflets being edged with tiny teeth. The genus is distributed mainly in the Mediterranean area, although some species are present also in Macaronesia, Central Europe CONTACT Maurizio Bruno [email protected] © 2016 Informa UK Limited, trading as Taylor & Francis Group 8 S. CASIGLIA et AL. and Asia. Currently, the genus comprises the 86 accepted species grouped in two sections, Natrix and Ononis, and 22 subsections (Turini et al. 2010). It is represented in Sicily by 21 taxa (Giardina et al. 2007). Chemical investigations of the genus showed the presence of resorcinol derivatives characteristic of the genus Ononis (Yousaf et al. 2015) and their occurrence has been reviewed some years ago (Zarnowski et al. 2001). Moreover, anthranilic derivatives (Al-Khalil et al. 1995; Khouni et al. 2014), flavonoids (Wollenweber et al. 2003; Mezrag et al. 2013; Benabderahmane et al. 2014; Mhamdi et al. 2015), norphenyl propanoid (Abdel-Kader 1997), coumarins (San Feliciano et al. 1990; Barrero et al. 1994; Hussain et al. 2001; Yousaf et al. 2015), hydroxycinnamic acids (Spilkova et al. 2001), sterols and triterpenoids (Shaker et al. 2004; Daruhazi et al. 2008) were isolated from several Ononis species. Several different biological properties such as cytotoxic (Barrero et al. 1997; Kuete et al. 2013), antitumor (Talib & Mahasneh 2012) antiviral against Herpes simplex type 1 (Abdel- Kader 2001), antihypertensive (Marhuenda Requena et al. 1987), diuretic (Marhuenda Requena & Garcia Gimenez 1985; Marhuenda et al. 1986), antibacterial (Marhuenda Requena & Garcia Gimenez 1986; Diaz et al. 1989; Al-Bakri & Afifi 2007; Kuete et al. 2013), in vivo wound healing (Süntar et al. 2011), anti-inflammatory (Kassem 2007; Abdel-Kader 2010; Süntar et al. 2011), antifungal (Altuner et al. 2010), insecticide (Erler et al. 2009), antioxidant and antimicrobial (Mhamdi et al. 2015) have been reported for species of this genus. Some of them have been used for centuries as folk remedies in Turkey and Jordan as diuretic, anti- septic, antitumour and antimicrobial (Tabata et al. 1988; Baytop 1999; Mahasneh & El-Oqlah 1999; Talib & Mahasneh 2010). In the Moroccan traditional medicine, the infusions of the roots and flowers of Ononis natrix have been used for the treatment of certain disturbances of the urinary tract (Bellakhdar 1997). Ononis reclinata L. (small restharrow), belonging to section Natrix, sub-section Reclinatae (Turini et al. 2010), is native to the Mediterranean region, in north-west Africa (Algeria, Morocco, Egypt) and Europe up to England and Balkans (http://ww2.bgbm.org/euroPlusMed/). It is an herbaceous annual plant, drooping to the ground, 25 cm high. Stems are covered with long, shaggy hairs and glands, often seen as tiny dots. The leaves are oblanceolate to obovate-orbicular. Primary branches of the inflorescence are up to 10 mm, corolla 5–10 mm, pink or purple, about equalling the calyx. It grows in dry grassy places. No previous phytochemical research has been reported on O. reclinata L. Consequently, in this study, as a continuation of researches on Sicilian species (Casiglia et al. 2016; Maggio et al. 2016; Riccobono et al. 2016), we report the chemical composition of the essential oils from aerial parts of O. reclinata L., growing wild in Sicily. 2. Results and discussion Hydrodistillation of the aerial parts of O. reclinata, collected at Piana degli Albanesi, gave a yellow oil. Overall, 16 compounds were identified in the oil, representing 99.0% of the total components. The components are listed in Table 1 according to their retention indices on a HP 5MS column. The oil of O. reclinata is quite rich in oxygenated monoterpenes (58.4%) with menthone (43.6%), the main component of the oil and pulegone (11.2%) as the lone constituents. Apart from a small amount of hydrocarbons (5.8%) it is noteworthy the large quantity of isopimp- inellin (38.4%). Also other compounds were detected but they were present only in amounts less than 0.03% and therefore in Table 1 are reported as traces. Table 2 reports the compo- sition of the other essential oils of Ononis taxa studied so far. NatUral ProdUct Research 9 Table 1. Chemical components of the essential oil from aerial parts of Ononis reclinata L. (Fabaceae). a c d e Ki Ki Components Ident. % Hydrocarbons 5.8 2200 2200 Docosane 1, 2,3 t 2300 2200 Tricosane 1, 2,3 1.0 2500 2300 Pentacosane 1, 2, 3 0.3 2700 2500 Heptacosane 1, 2,3 1.0 2900 2700 Nonacosane 1, 2, 3 3.5 Oxygented monoterpenes 54.8 1148 1143 Menthone 1, 2 43.6 1141 1144 Camphor 1, 2,3 t 1174 1174 Terpinen-4-ol 1, 2,3 t 1233 1233 Pulegone 1, 2 11.2 Sesqiterpene hydrocarbons 1373 1374 α-Copaene 1, 2 t 1522 1522 δ-Cadinene 1, 2 t Oxygenated sesquiterpenes 1582 1582 Caryophyllene oxide 1, 2,3 t 1649 1649 β-Eudesmol 1, 2 t Ketones 1843 1843 Hexahydrofarnesyl acetone 1, 2 t Others 38.4 1942 1942 (Z)-Phytol 1, 2 t 2240b 2240 Isopimpinellin 1, 2 38.4 Total 99.0 aRetention index taken from literature (Adams 2007). b(Feger et al. 2006). cRetention index on a DB5 column. dIdentification, 1 = comparison of retention index; 2 = comparison of mass spectra with MS libraries identification; 3 = com- parison with authentic compounds. et = trace, less than 0.03%. The comparison of the composition of the essential oil of O. reclinata with those reported in Table 2 shows some interesting points. The oil of Ononis sicula, the only other taxa belonging to sub-sect. Reclinatae studied so far, differently from the oil of O. reclinata, is very rich of sesquiterpenes (81.5%), whereas oxygenated monoterpenes are present in very few amounts (1.2%) (Al-Qudah et al. 2014). On the other hand, discrete quantities of oxygenated monoterpenes were observed in the oils of two different populations of O. natrix (sub-sect. Natrix), collected in Morocco (25.5 and 19.3%, respectively) (Khallouki et al. 2002; Elamrani & Benaissa 2010), although their composition is totally different with respect to the oil of O. reclinata. As stated before, the oil of O. reclinata is completely devoid of sesquiterpenes, occurring in the other taxa, with the exception of Ononis viscosa L. subsp. breviflora (DC) (1.2%), in quite large amounts (81.5–9.0%) and of carbonylic compounds, present, apart from O. natrix L. collected in Morocco, in all the other oils studied so far (51.3–7.6%). On the other hand, the oil of O. reclinata is quite rich in coumarin isopimpinellin: this class of com- pounds being never detected previously in other oils of Ononis species. From a biological point of view, the occurrence of menthone, isompinellin and pulegone, as main components of the oil of O. reclinata, has to be considered remarkable. In fact, menthone has been proved to have good antimicrobial activities against Acinetobacter cal- coacetica, Clostridium sporogenes, Staphylococcus aureus (Dorman & Deans 2000), Clavibacter michiganense, Klebsiella trevisanii (Kotan et al. 2007), Staphylococcus epidermidis (İşcan et al. 2002) and a moderate one against Botrytis cinerea (Bouchra et al. 2003); pulegone showed a high anticandidal effect against Candida albicans (Duru et al. 2004) and Kleiner et al. (2002) demonstrated that the oral administration