The essential oil obtained by hydrodistillation from the aerial parts of Brachyapium dichotomum (L.) Maire
(Apiaceae), was analyzed by GC-MS for the first time. Sixty-two compounds were detected, accounting for 96.1% of
the total oil, which is characterized by a high content of hydrocarbons derivatives of mono- and sesquiterpenes
(80.3%). The main constituents were α-pinene (36.5%), germacrene D (17.9%), dill apiole (6.7%) and myristicin
(3.5%)

Belkassam, A.

FLAMINI, GUIDO

Rebbas, K.

Smaili, T.

English

Flamini, Guido

Archivio della Ricerca - Università di Pisa

Chemical composition of the essential oil of Brachyapium dichotomum (L.) Maire

www.scholarsresearchlibrary.comt Available online a       Scholars Research Library  Der Pharmacia Lettre,  2016, 8 (10):32-36 (http://scholarsresearchlibrary.com/archive.html)   ISSN 0975-5071 USA CODEN: DPLEB4  32 Scholar Research Library Chemical composition of the essential oil of Brachyapium dichotomum (L.) Maire  Tahar Smailia*, Khellaf Rebbasa, Guido Flaminib and Abdelwahab Belkassama  aDepartment of Life Science and Nature, Faculty of Science, Mohamed Boudiaf University of M’sila, 28000, Algeria bDipartimento di Farmacia, Via Bonanno 6, 56126 Pisa, Italy _____________________________________________________________________________________________  ABSTRACT  The essential oil obtained by hydrodistillation from the aerial parts of Brachyapium dichotomum (L.) Maire (Apiaceae), was analyzed by GC-MS for the first time. Sixty-two compounds were detected, accounting for 96.1% of the total oil, which is characterized by a high content of hydrocarbons derivatives of mono- and sesquiterpenes (80.3%). The main constituents were α-pinene (36.5%), germacrene D (17.9%), dill apiole (6.7%) and myristicin (3.5%).  Keywords: Brachyapium dichotomum, Apiaceae, Essential oil, GC-MS, α-pinene _____________________________________________________________________________________________  INTRODUCTION  The family Apiaceae, or carrot family, is one of the most widely studied families of flowering plants, comprising about 450 genera with 3540 species [1,2].This large family is a well known producer of essential oil endowed with therapeutic properties, namely antibacterial, antioxidant and antifungal activities, therefore it is used as natural preservatives for food products [3,4]. Belonging to this family, Brachyapium, subfamily Apioideae, is represented by three species: B. dichotomum, distributed in North Africa and in the Western Mediterranean basin, especially in Spain [5,6], B.pomelianum, endemic of Algeria [7] and B. hanotei, which can be found only in Morocco [8].  According to the Flora of Algeria [7], the genus Brachyapium is constituted by two species: B. dichotomum (L.) Maire and B. pomelianum Maire. B. dichotomum (L.) Maire (syn. = Stoibrax dichotoma (L.) Rafin.L.) [5,9,10,11] is a small, annual herb that grows in mountain forests, dichotomous and branched from the base, with a celery odor and white flowers. The fruit is very small, about 1 mm, globular with hispid short capitates hairs [7].  To the best of our knowledge, there are no previous phytochemical reports concerning the whole Brachyapium genus. Therefore, the present investigation is reporting for the first time the composition of the essential oil obtained from Brachyapium dichotomum growing wild in Algeria.  MATERIALS AND METHODS  Plant material  The aerial parts of B. dichotomum were collected in May 2011 at M'sila (Algeria). Plants were identified by Dr Errol Vela, University of Montpellier 2 (French) and a voucher sample was deposited at the ddepartment of natural and life sciences, faculty of sciences, Mohamed Boudiaf University of M'sila, Algeria, plate number (ST/RK N°01) (Fig 1).  Tahar Smaili et al Der Pharmacia Lettre, 2016, 8 (10):32-36 ______________________________________________________________________________ 33 Scholar Research Library   Figure 1: Brachyapium dichotomum (L.) Maire of M’sila (Photo: K. Rebbas, 20.7.2015)  Essential oil extraction The dried plant material (200 g) was coarsely cut and hydrodistilled in a Clevenger-type apparatus for 2 h.  Chemical analysis  Gas chromatography – mass spectrometry analyses were performed with a Varian CP-3800 gas chromatograph equipped with a DB-5 capillary column (30m × 0.25 mm; coating thickness 0.25 µm) and a Varian Saturn 2000 ion trap mass detector. Analytical conditions: injector and transfer line temperatures 220 and 240°C,respectively; oven temperature programmed from 60°C to240°C at 3°C/min; carrier gas helium at 1 mL/min; injection 0.2 µL (10% n-hexane solution); split ratio 1:30.  Identification of volatile components The identification of the volatile constituents was based on comparison of the retention times with those of authentic samples, comparing their linear retention indices relative to the series of n-hydrocarbons, and by computer matching against commercial [12] and homemade library mass spectra built up from pure substances and components of known oils and MS literature data [12,13,14,15,16,17].  RESULTS AND DISCUSSION  The yield of the essential oil obtained from the aerial parts of B. dichotomum was 0.06% (w/w) and its composition is reported in Table 1. Sixty two compounds were characterized, representing 96.1% of the whole oil. The essential oil was mainly composed by monoterpene (50.1%), with hydrocarbon derivatives (48%) as the major group. Quite high amounts of α-pinene (36.5%) were detected. Oxygenated monoterpenes were found in lower percentages (2.1%), while sesquiterpenes (34.5%) constituted the second most abundant chemical class, largely represented by hydrocarbon derivatives (32.3%), with germacrene D (17.9%) as the major constituent. Oxygenated sesquiterpenes accounted for only 2.1%. Phenylpropanoids (11.6%) were another important class of volatiles in B. dichotomum essential oil. They were mainly represented by dill apiole (6.6%) and myristicin (3.5%). Trace amounts of non-terpene derivatives were also detected (Table 1).    Tahar Smaili et al Der Pharmacia Lettre, 2016, 8 (10):32-36 ______________________________________________________________________________ 34 Scholar Research Library Table 1: composition (%) of the essential oils of the aerial parts of Brachyapium dichotomum growing in Algeria Compound name RIa Content(%)b α-Thujene 931 trc α-Pinene 939 36.4 Camphene 954 0.4 Sabinene 977 0.7 β-Pinene 980 3.5 Myrcene 992 2.4 Octanal 1002 tr α-Terpinene 1018 tr p-Cymene 1027 0.6 Limonene 1031 1.1 1,8-Cineole 1034 0.3 (Z)-β-Ocimene 1041 tr (E)-β-Ocimene 1051 tr γ-Terpinene 1062 2.9 cis-Sabinene hydrate 1070 tr Terpinolene 1089 tr Linalool 1100 0.3 Nonanal 1103 tr cis-p-Menth-2-en-1-ol 1123 tr cis-Verbenol 1142 tr 4-Terpineol 1178 tr α-Terpineol 1190 tr Methyl thymol ether 1135 tr Methyl carvacrol ether 1244 tr cis-Chrysanthenyl acetate 1263 tr Thymol 1291 1.5 α-Cubebene 1351 0.5 α-Copaene 1376 0.9 β-Bourbonene 1384 0.8 β-Cubebene 1390 1.7 β-Elemene 1392 tr Methyl eugenol 1403 tr Dodecanal 1407 tr β-Caryophyllene 1418 0.5 β-Gurjunene 1432 0.2 Aromadendrene 1440 0.2 α-Humulene 1455 0.3 (E)-β-Farnesene 1459 tr Alloaromadendrene 1461 0.1 cis-Muurola-4(14),5-diene 1463 tr γ-Muurolene 1477 tr Germacrene D 1480 17.9 trans-Muurola-4(14),5-diene 1492 tr Bicyclogermacrene 1494 3.2 Epizonarene 1497 tr α-Bulnesene 1505 0.2 β-Bisabolene 1509 4.3 trans-γ-Cadinene 1513 0.3 Myristicin 1520 3.5 δ-Cadinene 1524 1.2 Elemicin 1554 tr Spathulenol 1576 0.8 Globulol 1583 0.2 Gleenol 1585 0.2 Isoaromadendrene  epoxide 1595 0.1 Humulene oxide II 1606 0.1 1,10-di-epi-Cubenol 1614 tr Dill apiole 1622 6.6 α-Acorenol 1631 tr T-Cadinol 1641 0.3 α-Cadinol 1654 0.4 Apiole 1680 1.5 Essential oils Yield (%, w/w)  0.06 Number of compounds  62 Class   Monoterpene hydrocarbons  48.0 Oxygenated monoterpenes  2.1 Sesquiterpene hydrocarbons  32.3 Tahar Smaili et al Der Pharmacia Lettre, 2016, 8 (10):32-36 ______________________________________________________________________________ 35 Scholar Research Library Oxygenated sesquiterpenes  2.1 Phenylpropanoids  11.6 Non-terpene derivatives  tr Total  96.1 a Retention index (RI) determined relatively to the retention time of a series of n-alkanes                                                                                                                                 b Content (%): Relative percentage calculated by GC/MS on an apolar capillary column HP-5                                                                                                                                                                                    c tr: traces (<0.1%)  In the literature, α-pinene which is the principal constituent in the volatile oils of B. dichotomum in our analyses is a common compound of the essential oils of several species of Apiaceae, such as Elaeoselinum asclepium subsp. meoides (60.8-92.2%) [18].                                                                                                                                                                                                                                                 On otherhand, it has been hypothesized that a Carum species, C. pimpinelloides from the Socotran Archipelago, could be closely correlated to B.dichotomum [19]. Chemical data could help to verify its correct placement within the Carum genus. In fact, in C.carvi the main constituents of the essential oil are limonene (7.6-18.2%) and carvone (23.3-86.4%) [20,21,22], sometimes together with other compounds such as trans-dihydrocarvone (14.0%), carvacrol (6.7%) and β−caryophyllene (6.1%) [23].  Carum copticum has thymol (54.5-64.5%) as main constituent, together with its biosynthetic precursors γ-terpinene (13.8-23.0%) and p-cymene (16.2-21.4%) [24,25,26]. Other Carum species produce very high percentages of phenylpropanoids. This is the case of C. montanum and C. nigrum, with nothoapiole (62.8 and 5.8%, respectively) and dill apiole (8.5 and 29.9%) [27,28]. Unfortunately, at present no data are available for C. pimpinelloides.  CONCLUSION  This is the first report on secondary metabolites of the Brachyapium genus. The study of the essential oil of Brachyapium dichotomum permitted us to identify 62 compounds. The plant biosynthesizes different chemical classes, mainly monoterpenes, sesquiterpenes and phenylpropanoids. The essential oil was characterized by a high content of monoterpene hydrocarbons, in particular α-pinene. Therefore, it is evident that the essential oil chemistry of this plant is quite different from that of the Carum genus.   Acknowledgments The authors are grateful to Dr Errol Vela of the University of Montpellier 2, France, for the plant description and identification and to the financial support of the Ministry of Higher Education and Scientific Research, Algeria.      REFERENCES  [1] Judd, W.S.; Camphell, C.S.; Kellogg, E.K.; Stevens, P.F. Plant systematics: A phylogenetic approach. Sunderland Sinauer Associates, 2008. [2] Mabberley, D.J. ; Mabberley’s Plant-Book: A portable dictionary of plants, their classification and uses. NewYork Cambridge University Press, 2008.   [3] De Martinoa, L.;  De Feoa, V.;  Fratiannib, F.; Nazzaro, F. Nat Prod Commun., 2009, 4,  1741-50. [4] Glisic, S.B.; Misic, D.R.; Stamenic, M.D.; Zizovic, I.T.; Asanin, R.M.;  Skala, D.U. Food Chem., 2007,  105, 346-52. [5] Arenas, J.A.; Garcia, F. Atlas carpologico y corologico de la subfamilia Apioideae Drude (Umbelliferae) en Espana peninsular y baleares. Ruizia Real Jardín Botánico (CSIC) Madrid. 1993. [6] Pottier-Alapetite, G. Flore de la Tunisie, Imprimerie officielle de la république Tunisienne, 1979. [7] Quezel, P.; Santa, S. Nouvelle flore de l'Algérie et des régions désertiques méridionales. Centre national de la recherche scientifique, Paris, 1963. [8]  Jahandiez, E. ; Maire, R. Catalogue des plantes du Maroc. Le chevalier, Paris, 1931. [9] Burtt, B.L. The adoption of Stoibrax for Tragiopis and Brachyapium (Umbelliferae), and its N-S African disjunction. In: Tan K. (ed): The davis and hedge festchrift plant taxonomy, phytogeography and related subjects. Edinburgh, 1989. [10] Le Floc’h, E.; Boulos, L.;  Vela, E. Catalogue synonymique commenté de la flore de Tunisie. République Tunisienne, Ministère de l’environnement  durable, Tunisie, 2010. [11] Valdés, B. ; Talavera, S. ; Fernandez-Galiano, E.Flora vascular de Andalucia occidental. Editora SA Ketres Barcelona, 1987.   [12] Adams, R.P. Identification of essential oil components by gas chromatography/mass spectrometry. 4 th Edition, Allured, Carol Stream IL USA, 2007. [13]  Davies, N.W. J Chromat. 1990, 50, 1-24. [14] Jennings, W.; Shibamoto T. Qualitative analysis of flavour and fragrance volatiles by glass capillary chromatography. Academic Press New York USA, 1980. Tahar Smaili et al Der Pharmacia Lettre, 2016, 8 (10):32-36 ______________________________________________________________________________ 36 Scholar Research Library [15] Massada, Y. Analysis of essential oils by gas chromatography and mass spectrometry. J Wiley & Sons New York USA, 1976. [16] Stenhagen, E.; Abrahamsson, S.; McLafferty, F.W.  Registry of mass spectral data. J Wiley & Sons New York USA, 1974. [17] Swigar, A.A.; Silverstein, R.M. Monoterpenes. Aldrich Chem Comp Milwaukee USA, 1981. [18] Bader, A.; Cioni, P.L.; Flamini,  G. Nat prod Commun, 2010, 5, 1111-4. [19] Barclay, E.L. ; Watson, M.F. Kew Bull. 1998, 53, 897-907. [20] Laribi, B.; Kouki, K.; Sahli, A.; Mougou, A.; Marzouk,  B.  Adv Environ Biol, 2011,  5, 257-64.   [21] Rolim De Almeida, L.F. ; Frei, F. ; Mancini, E. ; De Martino, L. ; De Feo,  V. Molecules, 2010, 15,  4309-23.   [22] Samojlik, I.; Lakic, N.; Mimica-Dukic, N.; Dakovic-Svajcer, K.; Bozin,  B. J Agric food chem., 2010,  58, 8848-53. [23] Acobellis, N.S.; Lo Cantore, P.; Capasso, F.;  Senatore,  F. J Agric Food Chem, 2005, 53, 57-61. [24] Marandi, R.J.;  Hassani, A.; Ghosta, Y.; Abdollahi, A.; Pirzad, A.; Sefidkon, F. J Med Plants Res, 2010, 4, 2424-30. [25] Mohagheghzadeh, A.; Faridi, P.; Ghasemi, Y. Food Chem, 2010, 100, 1217-19. [26] Shojaaddini, M.; Moharrami, S. J Plant Prot Res, 2008, 48, 411-9. [27] Laouer,  H.; El Kolli, M.; Prado, S.; Baldovini, N. Phytother Res, 2009, 23, 1726-30.   [28] Singh, G.; Marimuthu, P.; De Heluani, C.S.  J Agric food chem., 2006, 54, 174-81.      

https://arpi.unipi.it/bitstream/11568/796205/1/Brachyapium-DPL%202016.pdf

Chemical composition of the essential oil of Brachyapium dichotomum (L.) Maire

Abstract

Similar works

Full text

Available Versions

Archivio della Ricerca - Università di Pisa

Archivio della Ricerca - Università di Pisa