Chemical Components of the Essential Oil of Lantana camara L. Found in North Central Sudan Region of Nigeria

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1 American Chemical Science Journal 12(1): 1-7, 2016, Article no.acsj ISSN: SCIENCEDOMAIN international Chemical Components of the Essential Oil of Lantana camara L. Found in North Central Sudan Region of Nigeria Egharevba Henry Omoregie 1*, Ibrahim Jemilat Aliyu 1, Ebere Uchechukwu Doris 2, Okhale Samuel Ehiabhi 1 and Kunle Oluyemisi Folashade 1 1 Department of Medicinal Plant Research and Traditional Medicine, National Institute for Pharmaceutical Research and Development (NIPRD), Abuja, Nigeria. 2 Department of Chemistry, Faculty of Science, Imo State University, Owerri, Imo State, Nigeria. Authors contributions This work was carried out in collaboration between all authors. Author EHO designed the study, managed literature search, interpreted results and drafted manuscript. Author IJA supervised plant collection, identification and proof reading of draft manuscript. Authors EUD and OSE managed the lab analysis. Author KOF contributed to interpreting results and proof reading of the manuscript. Article Information DOI: /ACSJ/2016/22944 Editor(s): (1) Nagatoshi Nishiwaki, Kochi University of Technology, Japan. (2) Francisco Marquez-Linares, Full Professor of Chemistry, Nanomaterials Research Group, School of Science and Technology, University of Turabo, USA. Reviewers: (1) Ameen O. Mubarak, University of Ilorin, Ilorin, Nigeria. (2) Anonymous, Lagos State University Badagry, Lagos, Nigeria. (3) Saraswati Nandan Ojha, National Bureau of Plant Genetic Resources (ICAR), Uttarakhand, India. Complete Peer review History: Original Research Article Received 5 th November 2015 Accepted 12 th December 2015 Published 22 nd December 2015 ABSTRACT The essential oils of medicinal and aromatic plants remain a veritable tool in the management of ailments in ethnomedicine. Essential oils from medicinal plants had also been reported to possess various pharmacological activities, and have found relevance in food and industrial applications. Lantana camara L. is a well-known poisonous plant in ethnomedicine with proven numerous biological activities. The essential oil of the Nigerian species which has not been well studied was extracted by hydro-distillation and analyzed using a Shimadzu GC-MS QP2010 SE. The major chemical components of the oil were found to be Davanone (15.54%), Eucalyptol (12.72%), *Corresponding author: omoregieegharevba@yahoo.com;

2 β-phellandrene (10.58%), α-pinene (9.30%), Caryophyllene (6.99%), and (6E)-Nerolidol (5.68%). This is the first time Davanone has been reported from the species, and the species may present an alternative source for natural davanone. Keywords: Lantana camara; essential oil; davanone; β-phellandrene. 1. INTRODUCTION Lantana camara Linn. is a well-known tropical and subtropical poisonous plant belonging to the Verbenaceae family. The plant, which is commonly called wild sage, red sage, yellow sage or lantana, is locally called Kimbamahalba (Hausa), Anya nnunu (Igbo) and Ewonadele (Yoruba) [1,2]. The plant is widely used in ethnomedicine due to its numerous pharmacological benefits. It has been used to manage fevers, cold, rheumatisms, ulcers, catarrhal infection, malaria, tumour, cancer, asthma, high blood pressure, eczema, measles, bilious fever, abdominal viscera pains, sores, and a number of other ailments. The leaf of the plant had been reported to contain essential oils and other constituents some of which are responsible for its poisonous effect on livestocks like sheep and goats [2,3]. Also, the plant had been reported to exhibit numerous biological activities such as antibacterial, antifungal, antifilerial, antihypertensive, hemolitic, antiulcerogenic, antihelmentic, anti-inflammatory, antiproliferative, antifertility, antimotily activity, antipyretic activity, anti-cancer activity, anti-mutagenic activity, antihyperglycemic activity, hepatic protective activity, larvicidal activity, termiticidal activity and antioxidant activtities [2-4]. Researchers who worked on the plant also reported secondary metabolites such as phenolic, flavonoids, carbohydrates, proteins, alkaloids, glycosides, oligosaccharides, anthraquinone, saponins, steroids, terpenes and tannins [2,5]. The essential oil of the leaves had been reported to possess adulticidal activity against Aedes aegypti, Culex quinquefasciatus, Anopheles culicifacies, An. fluvialitis and An. stephensi mosquitoes. The major constituents of the essential oil reported were bicyclogermacrene (19.42%), isocaryphyllene (16.70%), valecene (12.94%), and germacrene D (12.34%) [2,6-8]. Zandi-Sohani et al. [9] also reported the essential oil of L. camara rich in α- humelene (23.3%) and cis-caryophyllene (16.2%) with strong repellent activity against adults of C. maculatus. However, much work has not been reported on the species growing locally in Nigeria. This study aims to undertake the GC- MS analysis of the essential oil of the leaves of the local invasive species with the view to establish and document its chemical profile, chemotype, and potential for beneficial biological activity. 2. MATERIALS AND METHODS 2.1 Materials All reagent used were of analytical grade and according to equipment specification. Other materials include mortar and pestle, Clevenger s type hydro-distillation apparatus and Shimadzu GC-MS QP2010 SE (Japan). 2.2 Plant Collection and Preparation Fresh leaves of Lantana camara was collected from Chazza Suleja, Niger state in July, The plant was identified at the NIPRD Herbarium with the voucher specimen number 5619 of The fresh leaves were separated from the stock and air-dried for seven days. The dried leaves were pulverized with the aid of mortar and pestle. The pulverized material was kept in airtight container until required. 2.3 Essential oil Extraction The pulverized dried leaf of L. camara (450 g) was subjected to hydro distillation using the Clevenger-type apparatus. The extracted essential oil was dried over anhydrous sodium sulphate and collected in sterile airtight glass sample bottle for GC-MS analysis. The percentage yield was calculated based on the dry weight of the leaf. 2.4 GC-MS Analysis The analysis of the hydro-distilled essential oil was carried out using a Shimadzu GC-MS model QP2010 SE (Japan) at the Shimadzu Training Centre for Analytical Instruments (STC) Lagos on 23 rd September GC-MS analysis was carried out using helium as carrier gas at a flow rate of 6.2 ml min -1 on Optima 5ms column of length, 30 m, internal diameter, 0.25 mm, and film thickness 0.25 µm. The conditions for analysis were set as follows; column oven temperature was programmed from C (i.e. temperature at 60 C was raised to 180 C at 2

3 10 C/min and held for 2 min, and then finally to 280 C at 15 C/min and held for 4 min). The Injection mode was split (1.0). The temperatures of the Injector and the detector were 250 and 280 C, respectively. The MS parameters were: m/z range was Da, and ion source temperature was 200 C. Essential oil compounds were identified and confirmed by matching their mass spectra with NIST11 mass spectral library collection. 3. RESULTS AND DISCUSSION The essential oil yield was 0.01%, and the result of GC-MS is as presented in Table 1. The GC chromatogram is as presented in Fig. 1. Table 1 revealed that 39 peaks were resolved and identified as constituting 100% of the oil. The percentage peak area was taken as percentage composition of the constituents. The major (above 5%) compounds in the oil were Davanone (15.54%), Eucalyptol (12.72%), β-phellandrene (10.58%), α-pinene (9.30%), Caryophyllene (6.99%) and (6E)-Nerolidol (5.68%) (Figs. 2 & 3). Though 39 components were also identified from the leaf essential oil of a Nigerian species by Kasali et al., the composition were however different from that obtained in this study. Kasali and coworkers reported major components of the essential oil of L. camara leaves in their study to be sabinene (19.6%), 1,8-cineole (12.6%), β- caryophyllene (12.7%) and α-humulene (5.8%) [10]. On the other hand, Oyedeji et al. reported 56 components with β-caryophyllene (24.6%), α- humulene (19.5%), sabinene (8.8%), germacrene D (5.7%) and cubebol (5.7%) as major identified constituents from the South Western region of Nigeria [11]. The components of their report also markedly differ from what was obtained in this study, suggesting the existence of a different chemotype rich in davanone in Nigeria. The essential oil in this study was also different from that reported by Seth et al. from Uttarakhand, India, where trans-caryophyllene (13.95%), bicyclogermacrene (9.77%), ±- curcumene (8.57%), sabinene (8.28%), (E)-citral (6.90%), 1,8 cineole (5.06%), ±-pinene (4.03%), γ-terpinene (3.83%) and germacrene D (3.13%) were the major components [12]. The essential oil from Seth et al. study was active against Micrococcus luteus, Escherichia coli, Staphylococcus aureus and Bacillus cereus but not against Pseudomonas aeruginosa. Similarly, Khan et al. reported germacrene-d (20.5%), γ-elemene (10.3%), β-caryophyllene (9.4%), β-elemene (7.3%), α-copaene (5.0%) and α-cadinene (3.3%) from Indian Lantana camara leaf oil [13]. In Brazil, a commercial lantana oil rich in bisabolene derivatives (about 65%) had been reported [14]. However, da Silva et al. [15] found different compositions from three different samples from different locations in Brazil. The major components in da Silva s work include limonene (16.5%), α-phellandrene (16.4%), germacrene-d (13.2%), β-caryophyllene (10.8%) and sabinene (8.9%), for sample A; germacrene- D (28.4%), germacrene-b (9.1%) and β- caryophyllene (5.6%) for sample B; and γ- curcumene/ar-curcumene (27.6%), α-zingiberene (19.2%) and α-humulene (10.7%) for sample C [15]. A comparison of all the components of the reported essential oils of L. camara with those obtained in this study showed a marked difference. The oil in this study is rich in davanone, eucalyptol, β-phellandrene and α- Pinene. Davana oil and essential oil of Artemisia herbaalba, which are rich in davanone (>40%) had been reported to exhibit antibacterial, antioxidant and insecticidal activities, although components of essential oils had been known to act in synergies [16]. Since the L. camara in this study contained appreciable amount of davano, it may be an alternative source of natural davanone. Cineole (eucalyptol) had been reported to exhibit antimicrobial activity including anti-trypanosomal activity [17]. Boehme et al. also reported that Zanthoxylum setulosum (Rutaceae) leaves oil rich in β-phellandrene (37.5%), Caryophyllene (13.7%), α-pinene (11.9%), germacrene D (10.9%), myrcene (5.9%), and nerolidol (5.4%) exhibited activity against Artemia salina (brine shrimp) but has neither cytotoxicity against Hep G2, MCF-7, and PC-3 human tumor cell lines nor antibacterial activity against Bacillus cereus, Staphylococcus aureus, Pseudomonas aeruginosa, and Escherichia coli [18]. Most insect repelling essential oil contains more than 10% caryophyllene and its analogues. Caryophyllene and its oxide are used as food, drug and cosmetic preservatives, as well as in flavor and fragrance. Caryophyllene oxides had been reported to possess antimicrobial, inhibitor of photosynthesis and plant growth enhancer [19-21]. Thus the relative balance in the constituents (no single component 20%) of the essential oil of the Nigeria species, which is rich in davanone, caryophellene, phellandrene, pinene and nerolidol may exhibit a range of activities such as antibacterial, antioxidant, insecticidal, insect repellant, and antitrypanosomal due to synergistic actions of its numerous bioactive components. 3

4 Table 1. Result of GC-MS analysis of the essential oil of L. camara S/N RT % MW Name (min) Composition (Da) R-α-Pinene β-phellandrene Carene Eucalyptol (Cineole) (Z)-3,7-dimethyl-1,3,6-Octatriene (1α,2β,5α)-2-methyl-5-(1-methylethyl)- Bicyclo[3.1.0]hexan-2-ol (+)-4-Carene (1α, 2β,5α)-2-methyl-5-(1-methylethyl)- Bicyclo[3.1.0]hexan-2-ol Camphor Isoborneol (R)-4-methyl-1-(1-methylethyl)-3-Cyclohexen-1-ol α-terpineol ethenyl-1-methyl-2-(1-methylethenyl)-4-(1- methylethylidene)- Cyclohexane α-copaene [1S-(1α,2β,4β)]-(1-ethenyl-1-methyl-2,4-bis(1- methylethenyl)-cyclohexane Caryophyllene ⅟-Muurolene Z,Z,Z-1,5,9,9-tetramethyl-1,4,7,-Cycloundecatriene octahydro-7-methyl-1hcyclopenta[1,3]cyclopropa[1,2]benzene ethenyl-1-methyl-2-(1-methylethenyl)-4-(1- methylethylidene) Cyclohexane Cubedol (6E)-Nerolidol Davanone Guaiol Caryophyllene oxide ,6-Dimethylbicyclo[3.2.1]octane beta.-Guaiene (-)-Spathulenol Ledol (3,3-Dimethyloxiran-2-yl)-2,7-dimethylnona-2,6- dien-1-ol (2-ethyl-1-methyl-1-butenyl)-Cyclohexane Lilac alcohol B (-)-Spathulenol [2S-[2.alpha.(R*),5.alpha.]]- 2-(5-ethenyltetrahydro- 5-methyl-2-furanyl)-6-methyl 5-Hepten-3-one (3-hydroxy-6,6-dimethyl-2-methylenecyclohexyl 3- Buten-2-one (1,3-Dimethyl-buta-1,3-dienyl)-1,5,5-trimethyl-7- oxa-bicyclo[4.1.0] hept-2-ene ,10,14-trimethyl-2-Pentadecanone (E,E)-3,7,11,15-tetramethyl-1,6,10,14- Hexadecatetraen-3-ol, Phytol RT = Retention Time, MW =Molecular weight 4

5 Fig. 1. Gas Chromatogram of the essential oil of L. camara species found in Northern Nigeria O H 2 C alpha-pinene CH 2 beta-phellandrene Eucalyptol Caryophyllene H 2 C OH C H 2 O O (6E)-Nerolidol Davanone Fig. 2. Chemical structures of major compounds in the essential oil of L. camara species in Nigeria (a) (b) (c) 5

6 (d) (e) (f) Fig. 3. Mass spectral of resolved compounds: (a) α-pinene, (b) β-phellandrene, (c) Eucalyptol, (d) Caryophyllene, (e) (6E)-Nerolidol, (f) Davanone 4. CONCLUSION The hydro-distilled essential oil of the leaf of L. camara species in North-central Nigeria is rich in davanone, β-phellandrene, caryophyllene, α- pinene, and (6E)-nerolidol. The essential oil may possess antimicrobial, insect repellent, and cytotoxic activity as reported for most davanone and phellandrene rich oils. This is the first time davanone is reported from the species and suggests that it could be an alternative source of natural davanone through genetic modification. The wide spectrum of volatiles in the oil may be of good industrial application as insect repellant, antimicrobial in food preservatives, and as fragrance or flavoring agent in cosmetics and pharmaceutical products. COMPETING INTERESTS Authors have declared that no competing interests exist. REFERENCES 1. Gabi B, Adewumi AAJ, Aina VO. Phytochemical characterization and in-vivo anti-malaria activity of Lantana camara leaf extract. Br. J. Pharmacol. Toxicol. 2011;2: Kalita S, Kumar G, Logonathan K, Venkata K, Rao B. Review of medicinal properties of Lantana camara Linn. Res J Pharma Technol. 2012;5(6): Kumarasamyraja D, Jeganathan NS, Manavana R. Pharmacological review of Lantana camara L. Int J Pharm Ind Res. 2012;2(1): Barreto FS, Sousa EO, Campos, AR, Costa JG, Rodrigues FF. Antibacterial activity of Lantana camara Linn and Lantana montevidensis brig extracts from Cariri-Ceará. Braz J Young Pharm. 2010; 2: Sousa EO, Costa JGM. Genus Lantana: chemical aspects and biological activities. Braz J Pharmacogn. 2012;22(5): Sousa EO, Silvia NF, Rodriguez FFG, Campos AR, Lima SG, Costa IJGM. Chemical composition and resistance modifying effect of the essential oil of Lantana camara Linn. Pharmacogn magazine. 2010;6(22): DOI: / Jawonisi IO, Adoga GI. Chemical constituents of essential oil of Lantana camara Linn. leaves. British J Pharmacol Toxicol. 2013;4(4): Reddy NM. A review on Lantana Camara Linn, chemical constituents and medicinal properties. Sch Acad J Pharm. 2013;2(6): Zandi-Sohani N, Hojjati M, Carbonell- Barrachina AA. Bioactivity of Lantana camara L. essential oil against Callosobruchus maculatus (Fabricius). Chilean J Agri Res. 2012;72(4):

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