Chemical Composition of Essential Oil of Tecurium mascatenses Bois Grown in Oman

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1 Journal of Essential Oil Bearing Plants ISSN Print: X Online: Jeobp 15 (5) 2012 pp Chemical Composition of Essential Oil of Tecurium mascatenses Bois Grown in Oman Marwa Mubarak AL Oraimi 1, Jamal Nasser Al-Sabahi 2, Afaf Mohammed Weli 1 *, Dina Selim 1, Mohammad Sohail Akhtar 1, Qasim Al-Riyami 1, Suliman Al-Khanjari 3 1 School of Pharmacy, College of Pharmacy and Nursing, University of Nizwa, Sultanate of Oman 2 Central Instrument Laboratory, college of Agricultural and Marine Sciences, Sultan Qaboos University, Sultanate of Oman 3 Research center, University of Nizwa, Sultanate of Oman Received 14 June 2011; accepted in revised form 25 November 2011 Abstract: Tecurium is a plant which belongs to the family Lamiaceae (Labiataea). This study was conducted in order to investigate the phytochemical composition of the leaves of Tuecrium mascatenses grown in Oman. The volume of the isolated oil was 1.2 ml 0.5 % w/w. Thirty two compounds were detected. The main constituents were limonene (17.2 %), linalool (12.4 %), α-pinene (10.1 %), β-eudesmol (10.1 %), unknown (7.6 %), linalyl acetate (4.3 %) bergamotene (4.3 %), β-pinene(3.5 %) and β-selinene (2.5 %). Key words: Teucrium mascatense, Limonene, Linalool, α-pinene, β-eudesmol. Introduction Herbal medication is important both traditionally and culturally and is a good source of raw materials for medication. Today most of the World s population depends on herbal medicines or alternative treatment for health care needs. The Sultanate of Oman is blessed with many useful trees and herbs due to the geographical diversity and climatic circumstances. Teucurium mascatense is indigenous to the Sultanate of Oman. There are more than 300 species of Teucurium all around the world 1. About 49 species are endemic to Europe mainly in the Mediterranean region and many of these species are used in the folk medicine of many countries as stimulants, tonics, and stomach ache remedy and also as anti-diabetic agents 2. Omani people have been aware of this herb for several ages and it has become popular and famous for a long time. The leaves are boiled in water for long time; the solution is cooled and taken as drink for stomach ache and colic. Dried leaves are burned and the smoke placed under bed covers for treating fevers. The leaves of Teucurium mascatense are also boiled in water with the leaves of Rhazya stricta, Fagonia indica, myrrh, sea salt and black salt (potassium chloride); the warm tea is taken for abdominal colic, fever and diabetes. Drinking the water in which leaves have been boiled is believed to reduce blood flow during menstruation. Endemic to northern Oman, in the rocky hills, above100 m flowering and fruiting in March to May 3. There are various reports related to the pharmacological properties of Teucurium species. They are commonly used in folk medicine for various types of pathological conditions as diabetes, inflammation, ulcer, *Corresponding author (Afaf Mohammed Weli) < afaf@unizwa.edu.om; afaf1954@yahoo.com > 2012, Har Krishan Bhalla & Sons

2 Marwa Mubarak AL Oraimi et al. / Jeobp 15 (5) hypertension, colic, and fever 4,5. Phytochemical investigations have shown that the herb contains various compounds such as flavonoids, iridoids and crisiol. However, many herbal medicinal plants including T. polium were found to induce fatal hepatic effects and severe acute liver failure with marked hematological and biochemical alterations after prolonged administration 6. Experimental Plant Material The plant was collected in month of May from Jabal al Akhdar area which is located in Nizwa town in Oman. The plant was identified at Daris Research Center, University of Nizwa. The identity was confirmed by the biology department at Sultan Qaboos University and a specimen of the plant was deposited at the herbarium of the same university. Isolation of essential oil The fresh leaves were separated from the plant and washed thoroughly with tap water to remove dirt then weighed (700 g) was subjected to hydrodistillation for about 3 hours in Clevengertype apparatus. The oil was separated from water by decantation and dried by filtration over anhydrous sodium sulphate. About 1.2 ml of the light yellow oil with pleasant and aromatic smell was obtained. The obtained oil was analyzed by GC-MS instrument. GC-MS: The analysis was done using GC-MS Perkin Elmer Model # Clarus 600 fitted with a HP-5MS capillary column (30 m x 0.25 mm i.d. x 0.25 μm film thickness) was used. The injection, transfer line and ion source were 290, 260 and 260 C respectively. The oven temperature was programmed from C (hold for 2 minutes) at a rate of 3 C/min. Helium (grade %) was used as carrier gas with a constant flow rate of 1ml/min. The injected volume of essential oil (EO) was 1 μl with a split ratio of 100:1. All data were obtained by collecting the full scan mass spectra within the range amu. The MS operating parameters were: ionization voltage of 70ev, scan rate of 500 amu/s. Each compound was identified by comparison of their spectral data with reference spectra in the data bases (Wiley AccessPak V7, May 2003 and NIST2005 version 2.1.0). A hydrocarbon standard mixture (C7-C24) was injected to calculate the kovat s indices of the EO components. Results and discussion Hydrodistillation of the leaves of T. mascatense produced 1.2 ml light yellow oil with pleasant and aromatic smell. Thirty two compounds were detected and the mass spectra of these compounds are shown below and they are listed in Table 1, in order of their elution on HP-5MS column. The composition of T. mascatense oil was found to be quite different from that of T. Polium with cases reported from the other regions Table 2. The essential oil of T.polium species has been studied in Iran, Yemen, Jordan, Turkey, and other countries Scientific study in Iran of T. polium essential oil found 28 compounds with (99.75 %). The major compounds of the oil were α-pinene (12.52 %), linalool (10.63 %), Caryophyllene oxide (9.69 %), β-pinene(7.09%) and β-caryophyllene (6.98 %) with percent constitute the highest percentage of essential oil 7. Hydro distillation of the leaves of Yemenes T. polium gave dark brown oil pleasant smell. The yield of oil was 0.45 % (w/w) and 12 Compounds were identified in the Oil (77.7 %) of the which the major compounds were γ-cadinene(34.9 %), β-caryophyllene(22.7 %), α-humulene(6.1 %), α- selinene(5.4 %)and two unidentified sesquiterpenes (16.5 %) 8. The chemical composition T. polium, grown in Jordan was determined by GC-MS. The oil obtained by hydro distillation was found to contain 39 components, of which 37 were identified. The major components determined were 8-cedren-13-ol (24.8 %), β-caryophllene (8.7 %), germacrene D (6.8 %)and sabinene (5.2 %) 9. Thirty seven components were detected in the oil obtained from the aerial parts of Turkish T. polium. The major components identified were β-pinene(18.0 %), β-caryophyllene (17.8 %), α- pinene(12 %), caryophyllene oxide (10.0 %), myrcene(6.8 %), germacrene D (5.3 %), limonene (3.5 %) and spathulenol(3.3 %) 13.

3 Marwa Mubarak AL Oraimi et al. / Jeobp 15 (5) Table 1. List of constituents of essential oil isolated from leaves of Tecrium mascatense Compound RI % α-thujene α-pinene β-pinene β-mycrene Limonene Linalool Verbbenol (trans) α-terpineol Carvone Linalyl acetate Unknown Geranayl acetate trans-caryophyllene Unknown trans-α-bergamotene Aromadendrene β-selinene Unknown Unknown δ-cadinene Unknown Nerolidol B (cis/trans) Unknown Caryophyllene oxide(-) Unknown Unknown tau-cadinol β-eudesmol α-eudesmol Torreyol Unknown Unknown Total 100 In the present study of T. mascatense leaf oil a total of 32 components were detected out of which 22 compounds were identified (table 1). limonene(17.3 %), linalool (12.4 %), limonene (17.2 %), α-pinene (10.1 %), β-eudesmol (10.1 %), linalyl acetate (4.3 %), bergamotene (4.3 %), β-pinene( 3.5 %) and β-selinene (2.5 %) were predominant compounds in this study. The other ten compounds could not be identified due to the lack of reference spectra in the library. The other study on the same species of Oman was also compared and found that most of the components were same but the major component limonene (17.3 %) was present in the current study and it was absent in other study 14. According to the previous studies, limonene has an antioxidant activity 15. Limonene also showed hepatic microsomal monooxygenase activity and paracetamol-induced glutathione depletion in mouse 16. Other major constituents present in this study like Linalool showed anticonvulsant activity in experimental models in mice an

4 Marwa Mubarak AL Oraimi et al. / Jeobp 15 (5) activity that was close to the diazepam 17. α- pinene and β-pinene have analgesic activity according to studies conducted on mice and rats. Therefore, based on these previous studies, it can be concluded that the essential oil of Omani T mascatense aerial parts contains lots of valuable constituents and can be used for therapeutic purposes in the future. Table 2. Comparison of T. mascatense grown in Oman with T. polium No. Compound Iran Yemene Jordan Turkish Oman T. Polium T. Polium T. Polium T. Polium T. mascatense 1 α-thujene β-pinene β-mycrene Limonene Linalool α-terpineol α-pinene Verbbenol(trans) Linalyl acetate trans-α-bergam otene Carvone Caryophyllene oxide Geranayl acetate β-eudesmol Aromadendrene α-pinene β-caryophyllene δ-cadinene γ-cadinene α-humulene α-selinen cedren-13-ol Germacrene D Sabinene Limonene β-selinene tau-cadinol α-eudesmol Torreyol Spathulenol References 1. Jackson, B.D. (1985). Index Kewensis. Oxonii E Prelo Clarendoniano, UK. 2. Ulubelen, A., Topcu, G., and, Sonmez,U. (2000). Chemical and biological evaluation of genus Teucrium. Studies in Natural Products Chemistry [Bioactive Natural Products (Part D)], Ghazanfar, S.A., and Al-Sabahi, A.M.A. ( 1993).Medicinal Plants of Northern and Central Oman (Arabia). Economic Botany, 47(1):

5 Marwa Mubarak AL Oraimi et al. / Jeobp 15 (5) Ajabnoor, M.A., Al-Yahya, M.A., Tariq,. Jayyab, A.A. (1984).Antidiabetic activity of Teucrium oliverianum. Fitoterapia, 75: Gharaibeh, M.N., Elayan, H.H., Salhab, A.S. ( 1988).Hypoglycemic effects of Teucrium polium. J. Ethnopharmacology.24: Khlleifat K., Shakhanbeh J., Tarawneh K. (2002).The Chronic Effects of Teucrium polium on Some Blood Parameters and Histopathology of Liver and Kidney in the Rat. Turk. J. Biol. 26: Mojab, F., Javidnia, K., Yazdanl, D., and Rustalyan, A. (2003). Essential oil of the aerial parts of Teucrium stocksianum Botss. subsp. stocksianum from Iran. Fasinamah-i Glyahan-i Oaruyl 2: Ali, N.A.A., Wurster, M., Arnold, N., Lindequist, U., and Wessjohan, L. (2008). Chemical Composition of the Essential Oil of Teucrium yemense Deflers Rec. Nat. Prod, 2: Aburjai, M., Hudaib, M. and Cavrini, V. (2006).Composition of the essential oil from Jordanian germander (Teucrium polium L.). J. Essent. Oil Res. 18: Al Yousuf, M.H., Bashir, A.K., Dobos, A., Veres, K., Nagy. Q., Mathe, I. and Blunden,G. (2002). The composition of the essential oil of Teucrium stocksianum from the United Arab Emirates. J. Essent. Oil Res, 4: Kovacevic, N.N., B.S. Lakusic, and Ristic, M.S. ( 2001).Composition of essential oils of seven Teucrium species from Serbia and Montenegro. J. Essent. Oil Res.13: Moghtader, M. (2009). Chemical Composition of the Essaetial Oil of Teucrium polium L. From Iran American-Eurasian J.Agric.& Environ.sci. 5(6): Yildirim, A., Cakir, A., Mavi, M., Yalcin, G., Fauler, Y., Taskesenligil, (2004). The variation of antioxidant activities and chemical composition of essential oils of Teucrium orientale L. var. orientale during harvesting stages. Flavour and Fragr. J. 19: Hisham, A., Pathare, N., Al-Saidi, S., Al-Salmi, (2006). A.Composition and Antimicrobial activity of leaf Essential Oil of Tecurium mascatenses Bioss. From Oman, J. Essent. Oil Res, (1): Roberto, D., Micucci, P., Sebastian, T., Graciela, F., Anesini, C. (2010). Antioxidant activity on normal murine lymphocytes: relation to H 2 O 2 modulation and cell proliferation. Basic Clinical Pharmacology Toxicology. 106(1): De Sousa, D.P., Nobrega, F.F., Santos, C.C., de Almeida, ( 2010).Anticonvulsant activity of the linalool enantiomers and racemate: investigation of chiral influence.natural Product Communication, 5(12): De Sousa, D.P. (2011). Analgesic-like Activity of Essential Oils Constituents. Molecules, 16:

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