Chemical Composition of the Essential Oil from the Aerial Parts of Ononis Reclinata L

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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.

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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 herbaceous 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 & Afifi2007 ; 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 ofOnonis 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 isopimpinellin (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 composition 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 = comparison 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 compounds 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 of isompinellin had chemopreventive effects on skin tumour initiation by DMBA. 10 S. Casiglia et al.

Table 2. Chemical composition of Ononis taxa studied so far. Compounds >0.9% were reported in the corresponding classes. A B C D E F G Hydrocarbons 3.5 0.3 0.2 1.7 Dodecane 1.5 Heptadecane 0.9 Octadecane 0.4 Monoterpene hydrocarbons 3.9 0.3 0.6 2.5 β-Pinene 0.3 1.8 Oxygented monoterpenes 0.9 1.0 25.6 18.3 1.6 1.2 11.1 Bornyl acetate 1.1 Camphor 16.2 5.5 Carvotanacetone 1.0 Terpinen-4-ol 0.9 1.0 2.8 0.1 Sesqiterpene hydrocarbons 24.9 5.8 39.1 8.0 15.4 20.1 0.6 Bicyclogermacrene 3.4 trans-cadina-1,4-diene 0.9 γ-Cadinene 3.4 0.7 0.9 δ-Cadinene 5.1 1.1 1.2 1.6 0.1 cis-calamenene 2.5 α-Calocorene 1.0 (E)-Caryophyllene 1.7 9.0 2.7 2.1 3.2 0.6 α-Copaene 2.4 0.7 0.2 β-Chamigrene 0.8 1.6 8,9-Dehydro-cycloisolongifolene 1.3 0.5 β-Elemene 1.7 α-Farnesene 3.4 (Z)-β-Farnesene 6.5 (E)-β-Farnesene 1.1 Germacrene D 3.6 β-Humulene 0.9 0.3

α-Longipinene 1.2 α-Muurolene 1.2 0.9 0.2 1.3 γ-Muurolene 1.1 6.6 α-Selinene 0.1 6.3 β-Selinene 2.7 1.2 2.7 1.8 5.2 β-Sesquiphellandrene 3.5 Valencene 5.0 0.3 Oxygenated sesquiterpenes 25.0 30.1 9.3 1.0 33.2 61.4 0.6 Aristolene epoxide 7.4 α-Bisabolol 0.1 1.9 α-Cadinol 0.7 1.2 0.3 t-Cadinol 1.2 epi-α-cadinol 1.0 1.9 Caryophyllene oxide 0.8 1.9 0.7 0.2 3.8 0.6 1-epi-cubenol 1.0 1,10-di-epi-cubenol 3.1 0.8 ar-Curcumen-15-al 2.5 Curcuphenol 0.9 10-epi-γ-eudesmol 2.3 α-Eudesmol 22.4 6.3 β-Eudesmol 7.5 3.7 γ-Eudesmol 1.4 1.4 (2E,6E)-Farnesal 2.6 (2E,6Z)-Farnesal 3.1 0.2 (2E,6E)-Farnesol 13.8 1.8 (2Z,6Z)-Farnesol 8.8 Guaiol 1.3 Intermedeol 10.7 Ledene oxide (ii) 0.6 α-Muurolol 4.1 0.5 0.5 (E)-Nerolidol 1.5 0.2 2.6 5.8 (continued) Natural Product Research 11

Table 2. (Continued). A B C D E F G 14-Oxy-alpha-muurolene 1.4 Selin-11-en-4-α-ol 2.2 12.8 Alcohols and phenols 2.4 2.7 2.9 17.1 5.3 1.1 13.4 (E)-Anethol 2.4 Carvavol 0.2 10.0 n-Decanol 1.9 Eugenol 1.1 0.9 1.0 (E)-2-Hexen-1-ol 1.2 Thymol 2.9 13.7 0.8 0.8 4-Vinylguaiacol 1.6 Aldehydes 8.4 1.6 17.2 2.4 17.9 Benzaldehyde 2.6 Decanal 0.2 3.2 Dodecanal 4.7 12.6 4.8 2-p-Methyl(phenyl)pentanal 1.0 n-Nonanal 2.5 0.4 5.5 Undecanal 1.1 0.9 2.2 Ketones 7.6 24.8 49.7 11.8 6.7 27.5 Acetophenone 1.4 7.4 0.1 (E,E)-Farnesylacetone 27.3 0.2 0.6 (E)-Geranylacetone 0.9 20.3 3.2 2.6 4.8 2-Heptadecanone 0.3 1.5 Hexahydrofarnesylacetone 3.0 3.5 5.0 0.8 12.5 (Z)-Jasmone 0.1 1.5 11-Methylundecan-2-one 3.1 2-Pentadecanone 1.0 0.6 1.7 2-Tridecanone 2.2 9.3 0.2 2.9 3.8 2-Undecanone 1.6 0.6 Carboxilic acids and esters 3.0 1.7 12.4 2.0 15.1 Capric acid 1.0 Caprylic acid 2.1 n-Hexanyl benzoate 1.2 1.8 3-Z-Hexenyl benzoate 1.8 Lauric acid 0.6 8.3 Myristic acid 1.7 2-Phenyl ethyl tiglate 5.2 2,2,4-Trimethylpentane-1,3-diol diisobutyrate 1.2 Tetradecanoic acid 1.2 Others 18.0 6.0 1.0 1.0 - - 1.6 (E)-β-Damascenone 1.4 Dimethyl-ionone 1.7 (E)-β-Ionone 2.9 Phytol 17.4 0.4 1.0 Prenyl-farnesene 1.0 A: O. angustissima (Lam.) Batt. et Trab. (sect. Natrix, sub-sect. Natrix), aerial parts, collected in Algeria (Youcef et al. 2014); B: O. angustissima L. (sect. Natrix, sub-sect. Natrix), aerial parts, collected in Tnisia (Ghribi et al. 2016); C: O. natrix L. (sect. Natrix, sub-sect. Natrix), aerial parts, collected in Morocco (Khallouki et al. 2002); D: O. natrix L. (sect. Natrix, sub-sect. Natrix), aerial parts, collected in Morocco (Elamrani & Benaissa 2010); E: O. natrix L. (sect. Natrix, sub-sect. Natrix), aerial parts, collected in Jordan (Al-Qudah et al. 2014); F: O. sicula Guss. (sect. Natrix, sub-sect. Reclinatae), aerial parts, collected in Jordan (Al-Qudah et al. 2014); G: O. viscosa L. subsp. breviflora (DC) (sect. Natrix, sub-sect. Viscosae), aerial parts, collected in Turkey (Erdemgil et al. 2002).

3. Experimental 3.1. Plant material Aerial parts (leaves, stems, and flowers) ofO. reclinata were collected 2 km west of Portella della Ginestra, Piana degli Albanesi, Palermo, Sicily, Italy (37°58′33″ N; 13°14′11″E; 790 m s/l) in the middle of May 2014, from plants at the full flowering stage. Typical specimens (PAL 12 S. Casiglia et al.

14/86), identified by Mr Emanuele Schimmenti, have been deposited in the Department STEBICEF, University of Palermo, Palermo, Italy.

3.2. Isolation of the essential oil The air-dried sample was ground in a Waring blender and then subjected to hydrodistillation for 3 h using n-hexane as solvent, according to the standard procedure previously described (Ben Jemia et al. 2013). The oil of O. reclinata was dried over anhydrous sodium sulphate and then stored in sealed vials, at −20 °C, ready for the GC and Gas chromatography-Mass spectrometry (GC-MS) analyses. The sample yielded 0.18% of oil (w/w) with a pleasant smell.

3.3. Qualitative and quantitative analyses The essential oil was analysed to determine the chemical components at the ‘Department of Pharmacy’ of the University of Naples ‘Federico II’ by GC and GC-MS. The GC analyses were carried out with a Perkin-Elmer Sigma 115 gas chromatograph fitted with a HP-5 MS and DB5 capillary columns (30 m × 0.25 mm i.d.; 0.25 μm film thickness) and equipped with a flame ionisation detector (FID. GC-MS was recorded on an Agilent 6850 Ser. II apparatus fitted with a fused silica HP-5 capillary column (30 m × 0.25 mm i.d.; 0.25 μm film thickness) and coupled to an Agilent Mass Selective Detector MSD 5973 as previously described (Loizzo et al. 2013). Identification of constituents was made as elsewhere reported (Zito et al.2013 ) by comparison of their retention indices (Ri) with either those of the literature (Jennings & Shibamoto 1980; Davies 1990). or with those of authentic compounds available in our laboratories. The retention indices were determined in relation to a homologous series of n-alkanes (C8–C30) under the same operating conditions. Further identification was made by comparison of their mass spectra with either those stored in NIST 02 and Wiley 275 libraries or with mass spectra from the literature (Jennings & Shibamoto 1980; Adams 2007) and our home-made library. Component relative concentrations were calculated based on GC peak areas without using correction factors

4. Conclusion In conclusion, with regard to O. reclinata essential oil, the results presented herein indicate a completely different chemical profile with respect to the other Ononis taxa studied so far. Although the environmental conditions such as soil composition, climate, etc. can drastically influence the composition of the secondary metabolites, the profile of the oil of O. reclinata shows some peculiar characteristics that should be considered in a possible botanical rec- ollocation. Further investigations on different population of this species from other geo- graphical contests should be necessary in order to clarify its botanical position.

Disclosure statement No potential conflict of interest was reported by the authors. Natural Product Research 13

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