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Natural Product Research: Formerly Natural Product Letters Publication details, including instructions for authors and subscription information: http://www.tandfonline.com/loi/gnpl20
Chemical composition and antioxidant activity of essential oil from aerial parts of Teucrium flavum L. subsp. flavum growing spontaneously in Tunisia a
b
a
Saoussen Hammami , Ridha El Mokni , Khaled Faidi , Danilo cd
d
d
a
Falconieri , Alessandra Piras , Silvia Procedda , Zine Mighri & Mohamed Hédi El Aouni
Click for updates
b
a
Research Unit 13ES63, Applied Chemistry and Environment, Faculty of Sciences, 5000 Monastir, Tunisia b
Laboratory of Botany and Plant Ecology, Faculty of Sciences of Bizerta, 7021 Jarzouna, Bizerta, Tunisia c
Industrial Technical Institute “Michele Giua”, Via Montecassino, 09134 Cagliari, Italy d
Department of Chemical and Geological Science, University of Cagliari, Cittadella Universitaria di Monserrato, S.P. MonserratoSestu km 0, 700 - 09042 Monserrato (CA), Italy Published online: 17 Feb 2015.
To cite this article: Saoussen Hammami, Ridha El Mokni, Khaled Faidi, Danilo Falconieri, Alessandra Piras, Silvia Procedda, Zine Mighri & Mohamed Hédi El Aouni (2015): Chemical composition and antioxidant activity of essential oil from aerial parts of Teucrium flavum L. subsp. flavum growing spontaneously in Tunisia, Natural Product Research: Formerly Natural Product Letters, DOI: 10.1080/14786419.2015.1010162 To link to this article: http://dx.doi.org/10.1080/14786419.2015.1010162
PLEASE SCROLL DOWN FOR ARTICLE Taylor & Francis makes every effort to ensure the accuracy of all the information (the “Content”) contained in the publications on our platform. However, Taylor & Francis, our agents, and our licensors make no representations or warranties whatsoever as to the accuracy, completeness, or suitability for any purpose of the Content. Any opinions and views expressed in this publication are the opinions and views of the authors,
and are not the views of or endorsed by Taylor & Francis. The accuracy of the Content should not be relied upon and should be independently verified with primary sources of information. Taylor and Francis shall not be liable for any losses, actions, claims, proceedings, demands, costs, expenses, damages, and other liabilities whatsoever or howsoever caused arising directly or indirectly in connection with, in relation to or arising out of the use of the Content.
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This article may be used for research, teaching, and private study purposes. Any substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing, systematic supply, or distribution in any form to anyone is expressly forbidden. Terms & Conditions of access and use can be found at http://www.tandfonline.com/page/termsand-conditions
Natural Product Research, 2015 http://dx.doi.org/10.1080/14786419.2015.1010162
SHORT COMMUNICATION Chemical composition and antioxidant activity of essential oil from aerial parts of Teucrium flavum L. subsp. flavum growing spontaneously in Tunisia Saoussen Hammamia*, Ridha El Moknib, Khaled Faidia, Danilo Falconiericd, Alessandra Pirasd, Silvia Proceddad, Zine Mighria and Mohamed He´di El Aounib a
Research Unit 13ES63, Applied Chemistry and Environment, Faculty of Sciences, 5000 Monastir, Tunisia; Laboratory of Botany and Plant Ecology, Faculty of Sciences of Bizerta, 7021 Jarzouna, Bizerta, Tunisia; c Industrial Technical Institute “Michele Giua”, Via Montecassino, 09134 Cagliari, Italy; dDepartment of Chemical and Geological Science, University of Cagliari, Cittadella Universitaria di Monserrato, S.P. Monserrato-Sestu km 0, 700 - 09042 Monserrato (CA), Italy
Downloaded by [McMaster University] at 11:43 23 February 2015
b
(Received 2 October 2014; final version received 18 January 2015)
The objectives of this study were to chemically characterise and evaluate the antioxidant potential of the essential oil from Teucrium flavum L. subsp. flavum growing spontaneously in Tunisia. The volatile oil was extracted by hydrodistillation of the aerial parts in a Clevenger type apparatus. Forty constituents were identified via GC and GC-MS analysis. b-caryophyllene (32.5%) and a-humulene (17.8%) were the most abundant components. The evaluation of free radical scavenging activity using stable DPPH free radical showed that the volatile oil exhibits a moderate antioxidant activity and reduces DPPH to 50% at EC50 value of 1230 mg mL21. Keywords: Teucrium flavum L. subsp. flavum; Lamiaceae; essential oil; aerial parts; GC/MS; b-caryophyllene; a-humulene; antioxidant effects
1. Introduction Since ancient times, medicinal plants have been widely considered of vital economic benefits in the development of indigenous medicines and in preventing many degenerative diseases. Recently, the Lamiaceae has been classified as one of the most important plant families of aromatic interests in terms of ethno medicine and medicinal values. They provide a high amount of essential oils widely used in pesticide, pharmaceutical, flavouring, perfumery, fragrance and cosmetic industries (Venkatesshappa & Sreenath 2013). Teucrium is one of the most cultivated genera including more than 300 species belonging to this family widespread around the world and comprises about 31 spontaneous taxa (23 species and 8 subspecies) in Tunisia (Le Floc’h et al.
*Corresponding author. Email: [email protected] q 2015 Taylor & Francis
2
S. Hammami et al.
Downloaded by [McMaster University] at 11:43 23 February 2015
2011). In folk medicine, many biological properties have already been ascribed to the genus Teucrium and among them diuretic, antispasmodic, antidiabetic, antirheumatic, antelmintic and anticancer effects (Miri et al. 2012; Mahmoudi & Nosratpour 2013). Several previous studies were carried out on the chemical composition and biological properties of essential oils from Teucrium species, showing a wide spectrum of biological activities due to the presence of sesquiterpenes as major constituents (Bezie´ et al. 2011). To the best of our knowledge, there are no previous reports on the composition of essential oils from the wild-growing population in Tunisia. In continuation of our contribution to the chemical study of medicinal plants (Benzarti et al. 2013; Hammami et al. 2013), this study presents the essential oil chemical composition from aerial parts of Teucrium flavum L. subsp. flavum that grows spontaneously in Mogods region (Tunisia) by means of GC-MS and GC-FID. Our results were compared to those described in the literature in relation with T. flavum from other countries. The antioxidant activity of the essential oil was also assessed using DPPH free radical-scavenging activity. 2. Results and discussion 2.1. Chemical composition In the present study, hydrodistillation of aerial parts from T. flavum growing in Tunisia gave yellow coloured, pleasant smelling essential oil which was analysed qualitatively and quantitatively by means of GC-FID and GC-MS. Table 1 shows the chemical constituents of the volatile oil. As can be seen from this table, forty compounds representing about 93.3% of the essential oil were identified. The major components are as follows: b-caryophyllene (32.5%), ahumulene (17.8%) and germacrene D (6.0%). The quality of the Tunisian T. flavum essential oil had some differences and similarities comparing with essential oils from other countries (Baher & Mirza 2003; Formisano et al. 2012). In fact, our sample was characterised by a high sesquiterpenes fraction (79.9%) of which 68.0% were sesquiterpenes hydrocarbons dominated by caryophyllene (32.5%) and a-humulene (17.8%). Similarly, sesquiterpenes (49.1%) constituted the most abundant fraction of the oil collected in Zakynthos Greece with a prevalence of sesquiterpene hydrocarbons (41.3%) among which caryophyllene (13.5%) and a-humulene (5.0%) predominated (Formisano et al. 2012). bcaryophyllene (23.1%), germacrene D (15.3%) and a-pinene (10.5%) were identified as the main constituents in Croatian T. flavum species (Bezie´ et al. 2011). The chemotypes of Tunisian T. flavum essential oil were in full agreement with those already reported in Iranian species for which the major components were b-caryophyllene (30.7%), germacrene D (21.3%) and ahumulene (8.4%) (Baher & Mirza 2003). However, the percent differences can be justified by the fact that the content of essential oils from plants cultivated in a variety of microclimatic areas may be affected by the influence of the altitude, the cultivation area, the origin and the stage of the collected material. b-caryophyllene, identified as the chemotype of the most Teucrium species, have been previously reported to possess several biological effects such as insecticidal, antimicrobial, local anaesthetic, anticarginotic and anti-inflammatory activities (Leandro et al. 2012). This may explain the pharmacological important effects of medicinal Teucrium essential oils. 2.2. DPPH Free radical-scavenging activity The free radical-scavenging activity of T. flavum essential oil was determined using DPPH and was compared to that of quercetin. From the analysis of Figure 1, we can conclude that the radical-scavenging activity of both the essential oil and positive control increased with increasing concentration. Teucrium oil possessed only mild DPPH radical scavenging ability as the IC50 value (1230 mg mL21) was more than 1000 mg mL21.
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Table 1. Chemical composition of essential oil of Tunisian T. flavum subsp. flavum aerial parts.
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Sl. No. 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15. 16. 17. 18. 19. 20. 21. 22. 23. 24. 25. 26. 27. 28. 29. 30. 31. 32. 33. 34. 35. 36. 37. 38. 39. 40.
RI 1027 1100 1151 1253 1301 1367 1374 1383 1392 1400 1405 1419 1427 1435 1452 1458 1475 1479 1493 1494 1499 1512 1515 1522 1575 1580 1589 1592 1600 1606 1633 1640 1652 1793 1845 1993 2111 2194 2394 2594
Compound Limonene Linalool p-Vinylanisole Isopentylhexanoate Carvacrol 3,4-Dimethoxystyrene a-Copaene b-Bourbonene 1-Tetradecene Tetradecane Iso-Caryophyllene b-Caryophyllene b-Copaene a-Trans-Bergamotene a-Humulene (E) -b-Farnesene g-Muurolene Germacrene D Valencene Bicyclogermacrene a-Muurolene b-Curcumene (Z)- g-Bisabolene d-Cadinene Spathulenol Caryophyllene oxide Viridiflorol 1-Hexadecene Ledol Humulene epoxide II Caryophylla-4(14),8(15)-dien-5- a-ol a-Muurolol a-Cadinol 1-Octadecene Hexahydrofarnesylacetone 1-Eicosane Phytol 1-Docosene 1-Tetracosene 1-Hexacosene Total identified Hydrocarbon monoterpenes Oxygenated monoterpenes Hydrocarbon sesquiterpenes Oxygenated sesquiterpenes Oxygenated diterpenes Others
% Area 0.2 0.2 0.3 0.8 1.8 0.3 0.3 1.4 0.6 0.2 0.2 32.5 0.3 0.2 17.8 1.0 0.5 6.0 0.4 0.3 0.4 0.8 4.0 1.9 0.3 4.9 1.8 1.5 0.6 1.7 0.5 0.5 0.5 1.7 0.3 2.0 0.5 1.7 1.5 0.9 93.3 0.2 2.0 68.0 11.9 0.5 10.6
Identification MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS,
RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI
3. Conclusion The present work highlights the GC analysis of the chemical composition of T. flavum essential oil and its antioxidant effects. As a result, T. flavum growing in Tunisia biosynthesised essential oil rich in bioactive sesquiterpenes. b-caryophyllene, germacrene D and a-humulene are the main constituents. The volatile oil showed a mild antioxidant activity. This may be explained by
4
S. Hammami et al.
DPPH Scavenging activity(%)
100 80 60 40 Essential oil 20
Quercetin
0
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0
0.5
1
1.5
2
2.5
3
C (mg/ml)
Figure 1. DPPH radical scavenging activities of T. flavum essential oil and Quercetin.
the fact that it is composed by almost entirely of sesquiterpenes which are not capable of donating a hydrogen atom and have low solubility in the reaction medium of the radicalscavenging essay.
Supplementary material Experimental details relating to this paper are available online.
Acknowledgements The authors thank the Istituto Tecnico Industriale M. Giua, Cagliari, ITI-GIUA for allowing the use of analytical instrumentations and methods within the collaboration agreement between DSCG-UNICA and ITI-GIUA.
References Baher ZF, Mirza M. 2003. Volatile constituents of Teucrium flavum L. from Iran. J. Essent Oil Res. 15:106–107. doi:10. 1080/10412905.2003.9712082. Benzarti A, Hammami S, Piras A, Falconieri D, El Mokni R, M’henni MF, Marongiu B, Mighri Z. 2013. Effects of different ecological conditions and extraction techniques on the quality of volatile oils from flaxleaf fleabane (Erigeron bonariensis L.). JMPR. 7:3059–3065. Bezie´ N, Vuko E, Dunkie´ V, Ruseie´ M, Blasevie´ I, Bureul F. 2011. Antiphytoviral activity of sesquiterpenes rich essential oils from four Croatian Teucrium species. Molecules. 16:8119– 8129. Formisano C, Rigano D, Senatore F, Bruno M, Maggio A, Piozzi F. 2012. Chemical composition of the essential oil of Teucrium flavum ssp. flavum from Zakynthos, Greece. Rec Nat Prod. 6:306–310. Hammami S, Salem A, Ashour ML, Cheriaa J, Graziano G, Mighri Z. 2013. A novel methylated sesquiterpene from seagrass Posidonia oceanica (L.) Delile. Nat Prod Res. 27:1265–1270. doi:10.1080/14786419.2012.725401. Leandro LM, De sousa vargas FDS, Barbosa PCS, Neves JKO, Da silva JAD, Da veiga-junior VFD. 2012. Chemistry and biological activities of terpenoids from Copaiba (Copaifera spp.) Oleoresins. Molecules. 17:3866–3889. doi:10. 3390/molecules17043866. Le Floc’h E, Boulos L, Vela E. 2010. Catalogue synonymique commente´ de la flore de Tunisie. Tunis. e´d. 2. 500 pp. Tunisie; p. 225–228. Mahmoudi R, Nosratpour S. 2013. Teucrium polium L. essential oil: phytochemical component and antioxidant properties. Food Res Int. 20:1697–1701.
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Miri A, Monsef-Esfahani HR, Amini M, Amanzadeh Y, Hadjiakhoondi A, Hajiaghaee R, Ebrahimi A. 2012. Comparative chemical composition and antioxidant properties of the essential oils and aromatic water from Teucrium persicum Boiss. Iran. J Pharm Res. 11:573–581. Tian W, Lin Q, Liu GC. 2012. In vitro antioxidant capacities of rice residue hydrolysates from fermented broth of five mold strains. JMPR. 6:2396–2401. Venkatesshappa SM, Sreenath KP. 2013. Potential medicinal plants of Lamiaceae. AIJRFANS. 3:82–87.
Natural Product Research: Formerly Natural Product Letters Publication details, including instructions for authors and subscription information: http://www.tandfonline.com/loi/gnpl20
Chemical composition and antioxidant activity of essential oil from aerial parts of Teucrium flavum L. subsp. flavum growing spontaneously in Tunisia a
b
a
Saoussen Hammami , Ridha El Mokni , Khaled Faidi , Danilo cd
d
d
a
Falconieri , Alessandra Piras , Silvia Procedda , Zine Mighri & Mohamed Hédi El Aouni
Click for updates
b
a
Research Unit 13ES63, Applied Chemistry and Environment, Faculty of Sciences, 5000 Monastir, Tunisia b
Laboratory of Botany and Plant Ecology, Faculty of Sciences of Bizerta, 7021 Jarzouna, Bizerta, Tunisia c
Industrial Technical Institute “Michele Giua”, Via Montecassino, 09134 Cagliari, Italy d
Department of Chemical and Geological Science, University of Cagliari, Cittadella Universitaria di Monserrato, S.P. MonserratoSestu km 0, 700 - 09042 Monserrato (CA), Italy Published online: 17 Feb 2015.
To cite this article: Saoussen Hammami, Ridha El Mokni, Khaled Faidi, Danilo Falconieri, Alessandra Piras, Silvia Procedda, Zine Mighri & Mohamed Hédi El Aouni (2015): Chemical composition and antioxidant activity of essential oil from aerial parts of Teucrium flavum L. subsp. flavum growing spontaneously in Tunisia, Natural Product Research: Formerly Natural Product Letters, DOI: 10.1080/14786419.2015.1010162 To link to this article: http://dx.doi.org/10.1080/14786419.2015.1010162
PLEASE SCROLL DOWN FOR ARTICLE Taylor & Francis makes every effort to ensure the accuracy of all the information (the “Content”) contained in the publications on our platform. However, Taylor & Francis, our agents, and our licensors make no representations or warranties whatsoever as to the accuracy, completeness, or suitability for any purpose of the Content. Any opinions and views expressed in this publication are the opinions and views of the authors,
and are not the views of or endorsed by Taylor & Francis. The accuracy of the Content should not be relied upon and should be independently verified with primary sources of information. Taylor and Francis shall not be liable for any losses, actions, claims, proceedings, demands, costs, expenses, damages, and other liabilities whatsoever or howsoever caused arising directly or indirectly in connection with, in relation to or arising out of the use of the Content.
Downloaded by [McMaster University] at 11:43 23 February 2015
This article may be used for research, teaching, and private study purposes. Any substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing, systematic supply, or distribution in any form to anyone is expressly forbidden. Terms & Conditions of access and use can be found at http://www.tandfonline.com/page/termsand-conditions
Natural Product Research, 2015 http://dx.doi.org/10.1080/14786419.2015.1010162
SHORT COMMUNICATION Chemical composition and antioxidant activity of essential oil from aerial parts of Teucrium flavum L. subsp. flavum growing spontaneously in Tunisia Saoussen Hammamia*, Ridha El Moknib, Khaled Faidia, Danilo Falconiericd, Alessandra Pirasd, Silvia Proceddad, Zine Mighria and Mohamed He´di El Aounib a
Research Unit 13ES63, Applied Chemistry and Environment, Faculty of Sciences, 5000 Monastir, Tunisia; Laboratory of Botany and Plant Ecology, Faculty of Sciences of Bizerta, 7021 Jarzouna, Bizerta, Tunisia; c Industrial Technical Institute “Michele Giua”, Via Montecassino, 09134 Cagliari, Italy; dDepartment of Chemical and Geological Science, University of Cagliari, Cittadella Universitaria di Monserrato, S.P. Monserrato-Sestu km 0, 700 - 09042 Monserrato (CA), Italy
Downloaded by [McMaster University] at 11:43 23 February 2015
b
(Received 2 October 2014; final version received 18 January 2015)
The objectives of this study were to chemically characterise and evaluate the antioxidant potential of the essential oil from Teucrium flavum L. subsp. flavum growing spontaneously in Tunisia. The volatile oil was extracted by hydrodistillation of the aerial parts in a Clevenger type apparatus. Forty constituents were identified via GC and GC-MS analysis. b-caryophyllene (32.5%) and a-humulene (17.8%) were the most abundant components. The evaluation of free radical scavenging activity using stable DPPH free radical showed that the volatile oil exhibits a moderate antioxidant activity and reduces DPPH to 50% at EC50 value of 1230 mg mL21. Keywords: Teucrium flavum L. subsp. flavum; Lamiaceae; essential oil; aerial parts; GC/MS; b-caryophyllene; a-humulene; antioxidant effects
1. Introduction Since ancient times, medicinal plants have been widely considered of vital economic benefits in the development of indigenous medicines and in preventing many degenerative diseases. Recently, the Lamiaceae has been classified as one of the most important plant families of aromatic interests in terms of ethno medicine and medicinal values. They provide a high amount of essential oils widely used in pesticide, pharmaceutical, flavouring, perfumery, fragrance and cosmetic industries (Venkatesshappa & Sreenath 2013). Teucrium is one of the most cultivated genera including more than 300 species belonging to this family widespread around the world and comprises about 31 spontaneous taxa (23 species and 8 subspecies) in Tunisia (Le Floc’h et al.
*Corresponding author. Email: [email protected] q 2015 Taylor & Francis
2
S. Hammami et al.
Downloaded by [McMaster University] at 11:43 23 February 2015
2011). In folk medicine, many biological properties have already been ascribed to the genus Teucrium and among them diuretic, antispasmodic, antidiabetic, antirheumatic, antelmintic and anticancer effects (Miri et al. 2012; Mahmoudi & Nosratpour 2013). Several previous studies were carried out on the chemical composition and biological properties of essential oils from Teucrium species, showing a wide spectrum of biological activities due to the presence of sesquiterpenes as major constituents (Bezie´ et al. 2011). To the best of our knowledge, there are no previous reports on the composition of essential oils from the wild-growing population in Tunisia. In continuation of our contribution to the chemical study of medicinal plants (Benzarti et al. 2013; Hammami et al. 2013), this study presents the essential oil chemical composition from aerial parts of Teucrium flavum L. subsp. flavum that grows spontaneously in Mogods region (Tunisia) by means of GC-MS and GC-FID. Our results were compared to those described in the literature in relation with T. flavum from other countries. The antioxidant activity of the essential oil was also assessed using DPPH free radical-scavenging activity. 2. Results and discussion 2.1. Chemical composition In the present study, hydrodistillation of aerial parts from T. flavum growing in Tunisia gave yellow coloured, pleasant smelling essential oil which was analysed qualitatively and quantitatively by means of GC-FID and GC-MS. Table 1 shows the chemical constituents of the volatile oil. As can be seen from this table, forty compounds representing about 93.3% of the essential oil were identified. The major components are as follows: b-caryophyllene (32.5%), ahumulene (17.8%) and germacrene D (6.0%). The quality of the Tunisian T. flavum essential oil had some differences and similarities comparing with essential oils from other countries (Baher & Mirza 2003; Formisano et al. 2012). In fact, our sample was characterised by a high sesquiterpenes fraction (79.9%) of which 68.0% were sesquiterpenes hydrocarbons dominated by caryophyllene (32.5%) and a-humulene (17.8%). Similarly, sesquiterpenes (49.1%) constituted the most abundant fraction of the oil collected in Zakynthos Greece with a prevalence of sesquiterpene hydrocarbons (41.3%) among which caryophyllene (13.5%) and a-humulene (5.0%) predominated (Formisano et al. 2012). bcaryophyllene (23.1%), germacrene D (15.3%) and a-pinene (10.5%) were identified as the main constituents in Croatian T. flavum species (Bezie´ et al. 2011). The chemotypes of Tunisian T. flavum essential oil were in full agreement with those already reported in Iranian species for which the major components were b-caryophyllene (30.7%), germacrene D (21.3%) and ahumulene (8.4%) (Baher & Mirza 2003). However, the percent differences can be justified by the fact that the content of essential oils from plants cultivated in a variety of microclimatic areas may be affected by the influence of the altitude, the cultivation area, the origin and the stage of the collected material. b-caryophyllene, identified as the chemotype of the most Teucrium species, have been previously reported to possess several biological effects such as insecticidal, antimicrobial, local anaesthetic, anticarginotic and anti-inflammatory activities (Leandro et al. 2012). This may explain the pharmacological important effects of medicinal Teucrium essential oils. 2.2. DPPH Free radical-scavenging activity The free radical-scavenging activity of T. flavum essential oil was determined using DPPH and was compared to that of quercetin. From the analysis of Figure 1, we can conclude that the radical-scavenging activity of both the essential oil and positive control increased with increasing concentration. Teucrium oil possessed only mild DPPH radical scavenging ability as the IC50 value (1230 mg mL21) was more than 1000 mg mL21.
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Table 1. Chemical composition of essential oil of Tunisian T. flavum subsp. flavum aerial parts.
Downloaded by [McMaster University] at 11:43 23 February 2015
Sl. No. 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15. 16. 17. 18. 19. 20. 21. 22. 23. 24. 25. 26. 27. 28. 29. 30. 31. 32. 33. 34. 35. 36. 37. 38. 39. 40.
RI 1027 1100 1151 1253 1301 1367 1374 1383 1392 1400 1405 1419 1427 1435 1452 1458 1475 1479 1493 1494 1499 1512 1515 1522 1575 1580 1589 1592 1600 1606 1633 1640 1652 1793 1845 1993 2111 2194 2394 2594
Compound Limonene Linalool p-Vinylanisole Isopentylhexanoate Carvacrol 3,4-Dimethoxystyrene a-Copaene b-Bourbonene 1-Tetradecene Tetradecane Iso-Caryophyllene b-Caryophyllene b-Copaene a-Trans-Bergamotene a-Humulene (E) -b-Farnesene g-Muurolene Germacrene D Valencene Bicyclogermacrene a-Muurolene b-Curcumene (Z)- g-Bisabolene d-Cadinene Spathulenol Caryophyllene oxide Viridiflorol 1-Hexadecene Ledol Humulene epoxide II Caryophylla-4(14),8(15)-dien-5- a-ol a-Muurolol a-Cadinol 1-Octadecene Hexahydrofarnesylacetone 1-Eicosane Phytol 1-Docosene 1-Tetracosene 1-Hexacosene Total identified Hydrocarbon monoterpenes Oxygenated monoterpenes Hydrocarbon sesquiterpenes Oxygenated sesquiterpenes Oxygenated diterpenes Others
% Area 0.2 0.2 0.3 0.8 1.8 0.3 0.3 1.4 0.6 0.2 0.2 32.5 0.3 0.2 17.8 1.0 0.5 6.0 0.4 0.3 0.4 0.8 4.0 1.9 0.3 4.9 1.8 1.5 0.6 1.7 0.5 0.5 0.5 1.7 0.3 2.0 0.5 1.7 1.5 0.9 93.3 0.2 2.0 68.0 11.9 0.5 10.6
Identification MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS, MS,
RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI RI
3. Conclusion The present work highlights the GC analysis of the chemical composition of T. flavum essential oil and its antioxidant effects. As a result, T. flavum growing in Tunisia biosynthesised essential oil rich in bioactive sesquiterpenes. b-caryophyllene, germacrene D and a-humulene are the main constituents. The volatile oil showed a mild antioxidant activity. This may be explained by
4
S. Hammami et al.
DPPH Scavenging activity(%)
100 80 60 40 Essential oil 20
Quercetin
0
Downloaded by [McMaster University] at 11:43 23 February 2015
0
0.5
1
1.5
2
2.5
3
C (mg/ml)
Figure 1. DPPH radical scavenging activities of T. flavum essential oil and Quercetin.
the fact that it is composed by almost entirely of sesquiterpenes which are not capable of donating a hydrogen atom and have low solubility in the reaction medium of the radicalscavenging essay.
Supplementary material Experimental details relating to this paper are available online.
Acknowledgements The authors thank the Istituto Tecnico Industriale M. Giua, Cagliari, ITI-GIUA for allowing the use of analytical instrumentations and methods within the collaboration agreement between DSCG-UNICA and ITI-GIUA.
References Baher ZF, Mirza M. 2003. Volatile constituents of Teucrium flavum L. from Iran. J. Essent Oil Res. 15:106–107. doi:10. 1080/10412905.2003.9712082. Benzarti A, Hammami S, Piras A, Falconieri D, El Mokni R, M’henni MF, Marongiu B, Mighri Z. 2013. Effects of different ecological conditions and extraction techniques on the quality of volatile oils from flaxleaf fleabane (Erigeron bonariensis L.). JMPR. 7:3059–3065. Bezie´ N, Vuko E, Dunkie´ V, Ruseie´ M, Blasevie´ I, Bureul F. 2011. Antiphytoviral activity of sesquiterpenes rich essential oils from four Croatian Teucrium species. Molecules. 16:8119– 8129. Formisano C, Rigano D, Senatore F, Bruno M, Maggio A, Piozzi F. 2012. Chemical composition of the essential oil of Teucrium flavum ssp. flavum from Zakynthos, Greece. Rec Nat Prod. 6:306–310. Hammami S, Salem A, Ashour ML, Cheriaa J, Graziano G, Mighri Z. 2013. A novel methylated sesquiterpene from seagrass Posidonia oceanica (L.) Delile. Nat Prod Res. 27:1265–1270. doi:10.1080/14786419.2012.725401. Leandro LM, De sousa vargas FDS, Barbosa PCS, Neves JKO, Da silva JAD, Da veiga-junior VFD. 2012. Chemistry and biological activities of terpenoids from Copaiba (Copaifera spp.) Oleoresins. Molecules. 17:3866–3889. doi:10. 3390/molecules17043866. Le Floc’h E, Boulos L, Vela E. 2010. Catalogue synonymique commente´ de la flore de Tunisie. Tunis. e´d. 2. 500 pp. Tunisie; p. 225–228. Mahmoudi R, Nosratpour S. 2013. Teucrium polium L. essential oil: phytochemical component and antioxidant properties. Food Res Int. 20:1697–1701.
Natural Product Research
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