Natural Product Research Formerly Natural Product Letters
ISSN: 1478-6419 (Print) 1478-6427 (Online) Journal homepage: http://www.tandfonline.com/loi/gnpl20
Essential oil composition, antioxidant activity and phenolic content of endemic Teucrium alyssifolium Staph. (Lamiaceae) Gürkan Semiz, Gurbet Çelik, Erhan Gönen & Aslı Semiz To cite this article: Gürkan Semiz, Gurbet Çelik, Erhan Gönen & Aslı Semiz (2016): Essential oil composition, antioxidant activity and phenolic content of endemic Teucrium alyssifolium Staph. (Lamiaceae), Natural Product Research, DOI: 10.1080/14786419.2016.1149703 To link to this article: http://dx.doi.org/10.1080/14786419.2016.1149703
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Published online: 26 Feb 2016.
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Date: 28 February 2016, At: 17:39
Natural Product Research, 2016 http://dx.doi.org/10.1080/14786419.2016.1149703
SHORT COMMUNICATION
Essential oil composition, antioxidant activity and phenolic content of endemic Teucrium alyssifolium Staph. (Lamiaceae) Gürkan Semiza, Gurbet Çelika, Erhan Gönena and Aslı Semizb Faculty of Arts & Sciences, Department of Biology, Pamukkale University, Denizli, Turkey; bMedical Laboratory Techniques, Vocational School of Health Services, Pamukkale University, Denizli, Turkey
Downloaded by [La Trobe University] at 17:39 28 February 2016
a
ABSTRACT
The present study was designed to examine the chemical composition of the essential oil, in vitro antioxidant activity and total phenolic and flavonoid content of extracts from plant parts (leaf, flower and stem) of Teucrium alyssifolium. The principle components of the essential oil were trans-β-caryophyllene (16.87%), ar-curcumene (11.43%) and bisabolene (11.06%), representing 39.36% of the oil. The total phenolic contents ranged between 13.99 and 41.54 mg of GAE/g of extract. The concentrations of flavonoids varied from 16.82 to 49.52 mg of Ru/g of extract. Antioxidant activity was determined in vitro using DPPH reagent and expressed as concentration of each extract required to inhibit radical by 50% (IC50) values that ranged from 13.52 to 132.55 μg/ml. Our results have indicated that water extract of T. alyssifolium (part leaf ) with a total content of polyphenols (41.54 mg of GAE/g) and an IC50 of 13.52 μg/ml is more antioxidant.
ARTICLE HISTORY
Received 3 November 2015 Accepted 9 January 2016 KEYWORDS
Antioxidant activity; total phenolic; total flavonoid; essential oil; GC-MS; Teucrium alyssifolium
1. Introduction Teucrium species are commonly used in traditional folk medicine for various types of pathological conditions as anti-diabetic (Ajabnoor et al. 1984), anti-inflammatory (Capasso et al. 1983), anti-ulcer (Twaij et al.1987), anti-bacterial (Ozkan et al. 2007) and insect feeding deterrent (Bruno et al. 2003). Many species of this genus are used in food industry and they show antimicrobial, antioxidant and antifungal activities rendering them useful as natural CONTACT Aslı Semiz [email protected] Supplemental data for this article can be accessed at http://dx.doi.org/10.1080/14786419.2016.1149703. © 2016 Taylor & Francis
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preservative ingredients (Ulubelen et al. 2000; Ozkan et al. 2007). Teucrium has 34 species (with 46 taxa) in Turkey, and 16 of these taxa are endemic (Dirmenci 2012). Teucrium alyssifolium Staph. is a narrowly distributed endemic species (Figure S1) classified as ‘Conservation Dependent (LR/cd)’ category of IUCN and taxonomically belongs to sect. Teucrium (Ekim et al. 2000). This study was designed to specifically investigate the distribution of phenolic compounds, as the carriers of antioxidant activity, in the essential oil and different vegetative parts of T. alyssifolium. Separate examination of plant parts allows a significant contribution to medicinal plant study and their pharmaceutical applications (Siddique et al. 2010). In addition, the extraction was done with water in order to correspond to human use. As far as we know, this work is the first report on the chemical composition of essential oil and the antioxidant activity and phenolic contents of T. alyssifolium.
2. Results and discussion 2.1. Chemical composition of the essential oil The GC-MS analysis of the essential oil of T. alyssifolium was resulted in detection of 27 components representing 93.11% of the oil (Table S1). These compounds included 6 monoterpene hydrocarbons (7.59%), 4 oxygenated monoterpenes (9.46%), 12 sesquiterpenes (61.40%) and 6 oxygenated sesquiterpenes (16.32%). The essential oil was characterised by a high amount of sesquiterpenes, of which trans-β-caryophyllene (16.87%) and ar-curcumene (11.43%) were the major compounds. It has been found that the sesquiterpenes were present as dominant constituents (especially caryophyllene and caryophyllene oxide) in the essential oil of Teucrium species (Formisano et al. 2009; Bagci et al. 2010). In some Teucrium species (e.g., Teucrium pestalozzae Boiss., Teucrium orientale L., Teucrium chamaedrys L., Teucrium scordium L., Teucrium quadrifarium Buch.-Ham., Teucrium flavum L. subsp. flavum), trans-β-caryophyllene was a major compounds in their essential oil composition (Başer et al. 1997; Morteza-Semnani et al. 2007; Mohan et al. 2010; Sagratini et al. 2012; Hammami et al. 2015). According to Dunkić et al. (2011), caryophyllene-oxide is a main compound (14.6%) of T. arduini essential oil from Croatia. In our study, caryophyllene-oxide was represented in 5.12% of the oil. In the literature, α-pinene was found the most abundant component in genus Teucrium (Moghtader 2009; Lograda et al. 2014; Casiglia et al. 2015; Purnavab et al. 2015), in our study, we found that α-pinene in very little amount (0.45%) which was supported by Nasser et al. (2008) from Yemen and Bagci et al. (2010) from Turkey have also found α-pinene in 0.96% and 0.2%, respectively. Some differences in the quantity and quality of the oil composition can be explained by environmental factor which are known to strongly influence the chemical composition of essential oils. As a result of these findings, the chemical composition of essential oil is compatible with the previous literature in terms of qualification of compounds in essential oil.
2.2. Total phenolic and flavonoid contents Total phenolic contents of the water extracts from plant parts (leaf, flower, and stem) and essential oil are presented in Figure S2. The total phenolic contents ranged between 13.99 and 41.54 mg of GAE/g of extract. As shown in Figure S2, the leaf extract of T. alyssifolium
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had the highest total phenolic content (41.54 mg GAE/g), while the essential oil showed the lowest (13.99 mg GAE/g). Total flavonoid contents of the water extracts from plant parts are presented in Figure S3. The concentrations of flavonoids varied from 16.82 to 49.52 mg of Ru/g of extract and essential oil. The leaf extract showed higher amount of flavonoid content (49.52 mg of Ru/g) than the other examined parts.
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2.3. Free radical scavenging activity using DPPH The DPPH free radical scavenging activities of T. alyssifolium water extracts and essential oil are shown in Table S2. Antioxidant activity was determined in vitro using DPPH reagent and expressed as concentration of each extract required to inhibit radical by 50% (IC50) values that ranged from 13.52 to 132.55 μg/ml. When compared to the activity of reference antioxidant rutin (IC50 = 9.28 μg/ml) (Stankovic et al. 2012), DPPH scavenging activity of leaf extract is high (IC50 = 13.52 μg/ml). The free radical scavenging activity of essential oil in compared with rutin was very low (IC50 = 132.55 μg/ml). These results have shown that phenolic extracts from T. alyssifolium have antioxidant power and the ability to scavenge free radicals. Additionally, we have found that there is a positive correlation between antioxidant activity and the total phenolic content of the extract from T. alyssifolium (Figure S4). In the Figure S4, it is important that an increase in the phenol content of extract decreases the IC50 value, i.e. increases their scavenging DPPH free-radical activity (negative correlation, r = −0.77). It was well reported that the antioxidant activity of plant materials was well correlated with the content of their phenolic compounds (Moein & Moein 2010; Stankovic et al. 2012; Zorzetto et al. 2015). In our study the weakest radical scavenging activity was exhibited by the essential oil and determined as 132.55 μg/ml (IC50). Numerous investigations of the antioxidant activity of plant extracts have confirmed a high linear correlation between the values of phenolic content and antioxidant activity (Sengul et al. 2009; Leccese et al. 2011; Stankovic et al. 2012; Chedia et al. 2013; Riahi et al. 2013; Alimpic et al. 2014). Phenolic compounds exhibit considerable free radical-scavenging activities (Rice-Evans et al. 1995). It is well known that phenolic substances such as flavonoids, phenolic acids and tannins contribute directly to the antioxidant capacity of plants (Hayase & Kato 1984). Flavonoids are widespread plant secondary metabolites and they have been shown to be highly effective scavengers of most oxidizing molecules, including singlet oxygen, and various free radicals (Bravo 1998; Chedia et al. 2013) implicated in several diseases. Epidemiological studies suggest that the consumption of flavonoid-rich foods protects against human diseases associated with oxidative stress (Enujiugha et al. 2012). Generally, plant materials rich in phenolics are increasingly being used in food industry because they retard oxidative degradation of lipids and improve the quality and nutritional value of food (Kähköne et al. 1999; Chedia et al. 2013).
3. Conclusions Our results showed that T. alyssifolium can be a source of polyphenols and flavonoids, confirm its antioxidant activities and underline its potential either as natural preservatives or in pharmaceutical applications. A comparison between vegetative plant parts and oil can
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G. Semiz et al.
be useful in estimating the efficacy of T. alyssifolium extracts as valuable plant materials to be used as natural antioxidants in phytotherapy. Additional in vivo antioxidant assays are needed to confirm the potential use of this species in disease treatment.
Acknowledgements The authors are grateful to Dr Gürçay Kıvanç AKYILDIZ who prepared the figures.
Disclosure statement
Downloaded by [La Trobe University] at 17:39 28 February 2016
The authors declare that there are no conflicts of interest. These authors contributed equally to this work.
Funding This work was supported by TUBITAK [grant number 110T976]; Pamukkale University, Scientific Research Project Unit [grant number 2014FBE042] to collect plant samples and laboratory analysis.
References Ajabnoor MA, Al-Yahya MA, Tariq M, Jayyab AA. 1984. Antidiabetic activity of Teucrium oliverianum. Fitoter. 75:227–230. Alimpić A, Oaldje M, Matevski V, Marin PD, Duletić-Laušević S. 2014. Antioxidant activity and total phenolic and flavonoid contents of Salvia amplexicaulis Lam. extracts. Arch Biol Sci . 66:307–316. Bagci E, Yazgın A, Hayta S, Cakılcıoglu U. 2010. Composition of the essential oil of Teucrium chamaedrys L. (Lamiaceae) from Turkey. J Med Plants Res. 4:2583–2587. Başer KHC, Demircakmak B, Duman H. 1997. Composition of the essential oil of three Teucrium species from Turkey. J Essent Oil Res. 9:545–549. Bravo L. 1998. Polyphenols: chemistry, dietary sources, metabolism and nutritional significance. Nutr Rev. 56:317–333. Bruno M, Maggio AM, Piozzi F, Puech S, Rosselli S, Simmonds MSJ. 2003. Neoclerodane diterpenoids from Teucrium polium subsp. polium and their antifeedant activity. Biochem Syst Ecol. 31:1051–1056. Capasso F, Cerri R, Morrica P, Senatore F. 1983. Chemical composition and anti-inflammatory activity of an alcoholic extract of Teucrium polium L. Boll Soc Ital Biol Sper. 59:1639–1643. Casiglia S, Jemia MB, Riccobono L, Bruno M, Scandolera E, Senatore F. 2015. Chemical composition of the essential oil of Moluccella spinosa L. (Lamiaceae) collected wild in Sicily and its activity on microorganisms affecting historical textiles. Nat Prod Res. 29:1201–1206. Chedia A, Ghazghazi H, Brahim H, Abderrazak M. 2013. Secondary metabolite, antioxidant and antibacterial activities of Teucrium polium L. methanolic extract. Int J Agron Plant Prod. 4:1790–1797. Dirmenci T. 2012. Teucrium L. In: Güner A, Aslan S, Ekim T, Vural M, Babaç MT, editors. List of Turkish flora (vascular plants). İstanbul: Nezahat Gökyiğit Botanic Garden and Flora Research Association Series; p. 595–598 (in Turkish). Dunkić V, Bezić N, Vuko E. 2011. Antiphytoviral activity of essential oil from endemic species Teucrium arduini L. Nat Prod Commun. 6:1385–1388. Ekim T, Koyuncu M, Vural M, Duman H, Aytaç Z, Adıgüzel N. 2000. Red data book of Turkish plants (Pteridophyta and Spermatophyta). Ankara: TTKD-Van Yüzüncü Yıl University, Barışcan Ofset (in Turkish). Enujiugha VN, Talabi JY, Malomo SA, Olagunju AL. 2012. DPPH radical scavenging capacity of phenolic extracts from African yam bean (Sphenostylis stenocarpa). Food Nutr Sci. 03:7–13. Formisano C, Rigano D, Senatore F, Al-Hillo MRY, Piozzi F, Rosselli S. 2009. Analysis of essential oil from Teucrium maghrebinum Greuter et Burdet growing wild in Algeria. Nat Prod Commun. 5:411–414.
Downloaded by [La Trobe University] at 17:39 28 February 2016
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Hammami S, El-Mokni R, Faidi K, Falconieri D, Piras A, Procedda S, Mighri Z, El-Aouni MH. 2015. Chemical composition and antioxidant activity of essential oil from aerial parts of Teucrium flavum L. subsp. flavum growing spontaneously in Tunisia. Nat Prod Res. 29:2336–2340. Hayase F, Katoi H. 1984. Antioxidative components of sweet potatoes. J Nutr Sci Vitaminol. 30:37–46. Kähköne MP, Hopia AI, Vuorela HJ, Rauha JP, Pihlaja K, Kujala TS, Heinonen M. 1999. Antioxidant activity of plant extracts containing phenolic compounds. J Agri Food Chem. 47:3954–3962. Leccese A, Viti R, Bartolini S. 2011. The effect of solvent extraction on antioxidant properties of apricot fruit. Cent Eur J Biol. 6:199–204. Lograda T, Ramdani M, Chalard P, Figueredo G, Deghar A. 2014. Chemical analysis and antimicrobial activity of Teucrium polium L. essential oil from eastern Algeria. AJAAD. 2:697–710. Moein S, Moein RM. 2010. Relationship between antioxidant properties and phenolics in Zhumeria majdae. J Med Plants Res. 4:517–521. Moghtader M. 2009. Chemical composition of the essential oil of Teucrium polium L. from Iran. AmEurasian J Agric Environ Sci. 5:843–846. Mohan L, Pant CC, Melkani AB, Dev V. 2010. Terpenoid composition of the essential oils of Teucrium royleanum and T. quadrifarium. Nat Prod Commun. 5:939–942. Morteza-Semnani K, Saeed M, Akbarzade M. 2007. Essential oil composition of Teucrium scordium L. Acta Pharm. 57:499–504. Nasser AAA, Wurster M, Arnold N, Lindequist U, Wessjohan L. 2008. Chemical composition of the essential oil of Teucrium yemense Deflers. Rec Nat Prod. 2:25–32. Özkan G, Kuleaşan H, Çeli̇k S, Göktürk RS, Ünal O. 2007. Screening of Turkish endemic Teucrium montbretii subsp. pamphylicum extracts for antioxidant and antibacterial activities. Food Control. 18:509–512. Purnavab S, Ketabchi S, Rowshan V. 2015. Chemical composition and antibacterial activity of methanolic extract and essential oil of Iranian Teucrium polium against some of phytobacteria. Nat Prod Res. 29:1376–1379. Riahi L, Chograni H, Elferchichi M, Zaouali Y, Zoghlami N, Mliki A. 2013. Variations in Tunisian wormwood essential oil profiles and phenolic contents between leaves and flowers and their effects on antioxidant activities. Ind Crops Prod. 46:290–296. Rice-Evans CA, Miller NJ, Bolwell PG, Bramley PM, Pridham JB. 1995. The relative antioxidant activities of plant-derived polyphenolic flavonoids. Free Rad Res. 22:375–383. Sagratini G, Maggi F, Bílek T, Papa F, Vittori S. 2012. Analysis of the volatile compounds of Teucrium flavum L. subsp. flavum (Lamiaceae) by headspace solid-phase microextraction coupled to gas chromatography with flame ionisation and mass spectrometric detection. Nat Prod Res. 26:1339– 1347. Sengul M, Yildiz H, Gungor N, Cetin B, Eser Z, Ercisli S. 2009. Total phenolic content, antioxidant and antimicrobial activities of some medicinal plants. Pak J Pharm Sci. 22:102–106. Siddique AN, Mujeeb M, Najmi AK, Akram M. 2010. Evaluation of antioxidant activity, quantitative estimation of phenols and flavonoids in different parts of Aegle marmelos. Af J Plant Sci. 4:1–5. Stankovic MS, Niciforovic N, Mihailovic V, Topuzovic M, Solujic S. 2012. Antioxidant activity, total phenolic content and flavonoid concentrations of different plant parts of Teucrium polium L. subsp. polium. Acta Soc Bot Pol. 81:117–122. Twaij HA, Albadr AA, Abul-Khail A. 1987. Anti-ulcer activity of Teucrium polium. Int J Crude Drug Res. 25:125–128. Ulubelen A, Topu G, Sönmez U. 2000. Chemical and biological evaluation of genus Teucrium. Stud Nat Prod Chem. 23:591–648. Zorzetto C, Sánchez-Mateo CC, Rabanal RM, Lupidi G, Bramucci M, Quassinti L, Iannarelli R, Papa F, Maggi F. 2015. Antioxidant activity and cytotoxicity on tumour cells of the essential oil from Cedronella canariensis var. canariensis (L.) Webb & Berthel. (Lamiaceae). Nat Prod Res. 29:1641–1649.
ISSN: 1478-6419 (Print) 1478-6427 (Online) Journal homepage: http://www.tandfonline.com/loi/gnpl20
Essential oil composition, antioxidant activity and phenolic content of endemic Teucrium alyssifolium Staph. (Lamiaceae) Gürkan Semiz, Gurbet Çelik, Erhan Gönen & Aslı Semiz To cite this article: Gürkan Semiz, Gurbet Çelik, Erhan Gönen & Aslı Semiz (2016): Essential oil composition, antioxidant activity and phenolic content of endemic Teucrium alyssifolium Staph. (Lamiaceae), Natural Product Research, DOI: 10.1080/14786419.2016.1149703 To link to this article: http://dx.doi.org/10.1080/14786419.2016.1149703
View supplementary material
Published online: 26 Feb 2016.
Submit your article to this journal
View related articles
View Crossmark data
Full Terms & Conditions of access and use can be found at http://www.tandfonline.com/action/journalInformation?journalCode=gnpl20 Download by: [La Trobe University]
Date: 28 February 2016, At: 17:39
Natural Product Research, 2016 http://dx.doi.org/10.1080/14786419.2016.1149703
SHORT COMMUNICATION
Essential oil composition, antioxidant activity and phenolic content of endemic Teucrium alyssifolium Staph. (Lamiaceae) Gürkan Semiza, Gurbet Çelika, Erhan Gönena and Aslı Semizb Faculty of Arts & Sciences, Department of Biology, Pamukkale University, Denizli, Turkey; bMedical Laboratory Techniques, Vocational School of Health Services, Pamukkale University, Denizli, Turkey
Downloaded by [La Trobe University] at 17:39 28 February 2016
a
ABSTRACT
The present study was designed to examine the chemical composition of the essential oil, in vitro antioxidant activity and total phenolic and flavonoid content of extracts from plant parts (leaf, flower and stem) of Teucrium alyssifolium. The principle components of the essential oil were trans-β-caryophyllene (16.87%), ar-curcumene (11.43%) and bisabolene (11.06%), representing 39.36% of the oil. The total phenolic contents ranged between 13.99 and 41.54 mg of GAE/g of extract. The concentrations of flavonoids varied from 16.82 to 49.52 mg of Ru/g of extract. Antioxidant activity was determined in vitro using DPPH reagent and expressed as concentration of each extract required to inhibit radical by 50% (IC50) values that ranged from 13.52 to 132.55 μg/ml. Our results have indicated that water extract of T. alyssifolium (part leaf ) with a total content of polyphenols (41.54 mg of GAE/g) and an IC50 of 13.52 μg/ml is more antioxidant.
ARTICLE HISTORY
Received 3 November 2015 Accepted 9 January 2016 KEYWORDS
Antioxidant activity; total phenolic; total flavonoid; essential oil; GC-MS; Teucrium alyssifolium
1. Introduction Teucrium species are commonly used in traditional folk medicine for various types of pathological conditions as anti-diabetic (Ajabnoor et al. 1984), anti-inflammatory (Capasso et al. 1983), anti-ulcer (Twaij et al.1987), anti-bacterial (Ozkan et al. 2007) and insect feeding deterrent (Bruno et al. 2003). Many species of this genus are used in food industry and they show antimicrobial, antioxidant and antifungal activities rendering them useful as natural CONTACT Aslı Semiz [email protected] Supplemental data for this article can be accessed at http://dx.doi.org/10.1080/14786419.2016.1149703. © 2016 Taylor & Francis
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G. Semiz et al.
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preservative ingredients (Ulubelen et al. 2000; Ozkan et al. 2007). Teucrium has 34 species (with 46 taxa) in Turkey, and 16 of these taxa are endemic (Dirmenci 2012). Teucrium alyssifolium Staph. is a narrowly distributed endemic species (Figure S1) classified as ‘Conservation Dependent (LR/cd)’ category of IUCN and taxonomically belongs to sect. Teucrium (Ekim et al. 2000). This study was designed to specifically investigate the distribution of phenolic compounds, as the carriers of antioxidant activity, in the essential oil and different vegetative parts of T. alyssifolium. Separate examination of plant parts allows a significant contribution to medicinal plant study and their pharmaceutical applications (Siddique et al. 2010). In addition, the extraction was done with water in order to correspond to human use. As far as we know, this work is the first report on the chemical composition of essential oil and the antioxidant activity and phenolic contents of T. alyssifolium.
2. Results and discussion 2.1. Chemical composition of the essential oil The GC-MS analysis of the essential oil of T. alyssifolium was resulted in detection of 27 components representing 93.11% of the oil (Table S1). These compounds included 6 monoterpene hydrocarbons (7.59%), 4 oxygenated monoterpenes (9.46%), 12 sesquiterpenes (61.40%) and 6 oxygenated sesquiterpenes (16.32%). The essential oil was characterised by a high amount of sesquiterpenes, of which trans-β-caryophyllene (16.87%) and ar-curcumene (11.43%) were the major compounds. It has been found that the sesquiterpenes were present as dominant constituents (especially caryophyllene and caryophyllene oxide) in the essential oil of Teucrium species (Formisano et al. 2009; Bagci et al. 2010). In some Teucrium species (e.g., Teucrium pestalozzae Boiss., Teucrium orientale L., Teucrium chamaedrys L., Teucrium scordium L., Teucrium quadrifarium Buch.-Ham., Teucrium flavum L. subsp. flavum), trans-β-caryophyllene was a major compounds in their essential oil composition (Başer et al. 1997; Morteza-Semnani et al. 2007; Mohan et al. 2010; Sagratini et al. 2012; Hammami et al. 2015). According to Dunkić et al. (2011), caryophyllene-oxide is a main compound (14.6%) of T. arduini essential oil from Croatia. In our study, caryophyllene-oxide was represented in 5.12% of the oil. In the literature, α-pinene was found the most abundant component in genus Teucrium (Moghtader 2009; Lograda et al. 2014; Casiglia et al. 2015; Purnavab et al. 2015), in our study, we found that α-pinene in very little amount (0.45%) which was supported by Nasser et al. (2008) from Yemen and Bagci et al. (2010) from Turkey have also found α-pinene in 0.96% and 0.2%, respectively. Some differences in the quantity and quality of the oil composition can be explained by environmental factor which are known to strongly influence the chemical composition of essential oils. As a result of these findings, the chemical composition of essential oil is compatible with the previous literature in terms of qualification of compounds in essential oil.
2.2. Total phenolic and flavonoid contents Total phenolic contents of the water extracts from plant parts (leaf, flower, and stem) and essential oil are presented in Figure S2. The total phenolic contents ranged between 13.99 and 41.54 mg of GAE/g of extract. As shown in Figure S2, the leaf extract of T. alyssifolium
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had the highest total phenolic content (41.54 mg GAE/g), while the essential oil showed the lowest (13.99 mg GAE/g). Total flavonoid contents of the water extracts from plant parts are presented in Figure S3. The concentrations of flavonoids varied from 16.82 to 49.52 mg of Ru/g of extract and essential oil. The leaf extract showed higher amount of flavonoid content (49.52 mg of Ru/g) than the other examined parts.
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2.3. Free radical scavenging activity using DPPH The DPPH free radical scavenging activities of T. alyssifolium water extracts and essential oil are shown in Table S2. Antioxidant activity was determined in vitro using DPPH reagent and expressed as concentration of each extract required to inhibit radical by 50% (IC50) values that ranged from 13.52 to 132.55 μg/ml. When compared to the activity of reference antioxidant rutin (IC50 = 9.28 μg/ml) (Stankovic et al. 2012), DPPH scavenging activity of leaf extract is high (IC50 = 13.52 μg/ml). The free radical scavenging activity of essential oil in compared with rutin was very low (IC50 = 132.55 μg/ml). These results have shown that phenolic extracts from T. alyssifolium have antioxidant power and the ability to scavenge free radicals. Additionally, we have found that there is a positive correlation between antioxidant activity and the total phenolic content of the extract from T. alyssifolium (Figure S4). In the Figure S4, it is important that an increase in the phenol content of extract decreases the IC50 value, i.e. increases their scavenging DPPH free-radical activity (negative correlation, r = −0.77). It was well reported that the antioxidant activity of plant materials was well correlated with the content of their phenolic compounds (Moein & Moein 2010; Stankovic et al. 2012; Zorzetto et al. 2015). In our study the weakest radical scavenging activity was exhibited by the essential oil and determined as 132.55 μg/ml (IC50). Numerous investigations of the antioxidant activity of plant extracts have confirmed a high linear correlation between the values of phenolic content and antioxidant activity (Sengul et al. 2009; Leccese et al. 2011; Stankovic et al. 2012; Chedia et al. 2013; Riahi et al. 2013; Alimpic et al. 2014). Phenolic compounds exhibit considerable free radical-scavenging activities (Rice-Evans et al. 1995). It is well known that phenolic substances such as flavonoids, phenolic acids and tannins contribute directly to the antioxidant capacity of plants (Hayase & Kato 1984). Flavonoids are widespread plant secondary metabolites and they have been shown to be highly effective scavengers of most oxidizing molecules, including singlet oxygen, and various free radicals (Bravo 1998; Chedia et al. 2013) implicated in several diseases. Epidemiological studies suggest that the consumption of flavonoid-rich foods protects against human diseases associated with oxidative stress (Enujiugha et al. 2012). Generally, plant materials rich in phenolics are increasingly being used in food industry because they retard oxidative degradation of lipids and improve the quality and nutritional value of food (Kähköne et al. 1999; Chedia et al. 2013).
3. Conclusions Our results showed that T. alyssifolium can be a source of polyphenols and flavonoids, confirm its antioxidant activities and underline its potential either as natural preservatives or in pharmaceutical applications. A comparison between vegetative plant parts and oil can
4
G. Semiz et al.
be useful in estimating the efficacy of T. alyssifolium extracts as valuable plant materials to be used as natural antioxidants in phytotherapy. Additional in vivo antioxidant assays are needed to confirm the potential use of this species in disease treatment.
Acknowledgements The authors are grateful to Dr Gürçay Kıvanç AKYILDIZ who prepared the figures.
Disclosure statement
Downloaded by [La Trobe University] at 17:39 28 February 2016
The authors declare that there are no conflicts of interest. These authors contributed equally to this work.
Funding This work was supported by TUBITAK [grant number 110T976]; Pamukkale University, Scientific Research Project Unit [grant number 2014FBE042] to collect plant samples and laboratory analysis.
References Ajabnoor MA, Al-Yahya MA, Tariq M, Jayyab AA. 1984. Antidiabetic activity of Teucrium oliverianum. Fitoter. 75:227–230. Alimpić A, Oaldje M, Matevski V, Marin PD, Duletić-Laušević S. 2014. Antioxidant activity and total phenolic and flavonoid contents of Salvia amplexicaulis Lam. extracts. Arch Biol Sci . 66:307–316. Bagci E, Yazgın A, Hayta S, Cakılcıoglu U. 2010. Composition of the essential oil of Teucrium chamaedrys L. (Lamiaceae) from Turkey. J Med Plants Res. 4:2583–2587. Başer KHC, Demircakmak B, Duman H. 1997. Composition of the essential oil of three Teucrium species from Turkey. J Essent Oil Res. 9:545–549. Bravo L. 1998. Polyphenols: chemistry, dietary sources, metabolism and nutritional significance. Nutr Rev. 56:317–333. Bruno M, Maggio AM, Piozzi F, Puech S, Rosselli S, Simmonds MSJ. 2003. Neoclerodane diterpenoids from Teucrium polium subsp. polium and their antifeedant activity. Biochem Syst Ecol. 31:1051–1056. Capasso F, Cerri R, Morrica P, Senatore F. 1983. Chemical composition and anti-inflammatory activity of an alcoholic extract of Teucrium polium L. Boll Soc Ital Biol Sper. 59:1639–1643. Casiglia S, Jemia MB, Riccobono L, Bruno M, Scandolera E, Senatore F. 2015. Chemical composition of the essential oil of Moluccella spinosa L. (Lamiaceae) collected wild in Sicily and its activity on microorganisms affecting historical textiles. Nat Prod Res. 29:1201–1206. Chedia A, Ghazghazi H, Brahim H, Abderrazak M. 2013. Secondary metabolite, antioxidant and antibacterial activities of Teucrium polium L. methanolic extract. Int J Agron Plant Prod. 4:1790–1797. Dirmenci T. 2012. Teucrium L. In: Güner A, Aslan S, Ekim T, Vural M, Babaç MT, editors. List of Turkish flora (vascular plants). İstanbul: Nezahat Gökyiğit Botanic Garden and Flora Research Association Series; p. 595–598 (in Turkish). Dunkić V, Bezić N, Vuko E. 2011. Antiphytoviral activity of essential oil from endemic species Teucrium arduini L. Nat Prod Commun. 6:1385–1388. Ekim T, Koyuncu M, Vural M, Duman H, Aytaç Z, Adıgüzel N. 2000. Red data book of Turkish plants (Pteridophyta and Spermatophyta). Ankara: TTKD-Van Yüzüncü Yıl University, Barışcan Ofset (in Turkish). Enujiugha VN, Talabi JY, Malomo SA, Olagunju AL. 2012. DPPH radical scavenging capacity of phenolic extracts from African yam bean (Sphenostylis stenocarpa). Food Nutr Sci. 03:7–13. Formisano C, Rigano D, Senatore F, Al-Hillo MRY, Piozzi F, Rosselli S. 2009. Analysis of essential oil from Teucrium maghrebinum Greuter et Burdet growing wild in Algeria. Nat Prod Commun. 5:411–414.
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Hammami S, El-Mokni R, Faidi K, Falconieri D, Piras A, Procedda S, Mighri Z, El-Aouni MH. 2015. Chemical composition and antioxidant activity of essential oil from aerial parts of Teucrium flavum L. subsp. flavum growing spontaneously in Tunisia. Nat Prod Res. 29:2336–2340. Hayase F, Katoi H. 1984. Antioxidative components of sweet potatoes. J Nutr Sci Vitaminol. 30:37–46. Kähköne MP, Hopia AI, Vuorela HJ, Rauha JP, Pihlaja K, Kujala TS, Heinonen M. 1999. Antioxidant activity of plant extracts containing phenolic compounds. J Agri Food Chem. 47:3954–3962. Leccese A, Viti R, Bartolini S. 2011. The effect of solvent extraction on antioxidant properties of apricot fruit. Cent Eur J Biol. 6:199–204. Lograda T, Ramdani M, Chalard P, Figueredo G, Deghar A. 2014. Chemical analysis and antimicrobial activity of Teucrium polium L. essential oil from eastern Algeria. AJAAD. 2:697–710. Moein S, Moein RM. 2010. Relationship between antioxidant properties and phenolics in Zhumeria majdae. J Med Plants Res. 4:517–521. Moghtader M. 2009. Chemical composition of the essential oil of Teucrium polium L. from Iran. AmEurasian J Agric Environ Sci. 5:843–846. Mohan L, Pant CC, Melkani AB, Dev V. 2010. Terpenoid composition of the essential oils of Teucrium royleanum and T. quadrifarium. Nat Prod Commun. 5:939–942. Morteza-Semnani K, Saeed M, Akbarzade M. 2007. Essential oil composition of Teucrium scordium L. Acta Pharm. 57:499–504. Nasser AAA, Wurster M, Arnold N, Lindequist U, Wessjohan L. 2008. Chemical composition of the essential oil of Teucrium yemense Deflers. Rec Nat Prod. 2:25–32. Özkan G, Kuleaşan H, Çeli̇k S, Göktürk RS, Ünal O. 2007. Screening of Turkish endemic Teucrium montbretii subsp. pamphylicum extracts for antioxidant and antibacterial activities. Food Control. 18:509–512. Purnavab S, Ketabchi S, Rowshan V. 2015. Chemical composition and antibacterial activity of methanolic extract and essential oil of Iranian Teucrium polium against some of phytobacteria. Nat Prod Res. 29:1376–1379. Riahi L, Chograni H, Elferchichi M, Zaouali Y, Zoghlami N, Mliki A. 2013. Variations in Tunisian wormwood essential oil profiles and phenolic contents between leaves and flowers and their effects on antioxidant activities. Ind Crops Prod. 46:290–296. Rice-Evans CA, Miller NJ, Bolwell PG, Bramley PM, Pridham JB. 1995. The relative antioxidant activities of plant-derived polyphenolic flavonoids. Free Rad Res. 22:375–383. Sagratini G, Maggi F, Bílek T, Papa F, Vittori S. 2012. Analysis of the volatile compounds of Teucrium flavum L. subsp. flavum (Lamiaceae) by headspace solid-phase microextraction coupled to gas chromatography with flame ionisation and mass spectrometric detection. Nat Prod Res. 26:1339– 1347. Sengul M, Yildiz H, Gungor N, Cetin B, Eser Z, Ercisli S. 2009. Total phenolic content, antioxidant and antimicrobial activities of some medicinal plants. Pak J Pharm Sci. 22:102–106. Siddique AN, Mujeeb M, Najmi AK, Akram M. 2010. Evaluation of antioxidant activity, quantitative estimation of phenols and flavonoids in different parts of Aegle marmelos. Af J Plant Sci. 4:1–5. Stankovic MS, Niciforovic N, Mihailovic V, Topuzovic M, Solujic S. 2012. Antioxidant activity, total phenolic content and flavonoid concentrations of different plant parts of Teucrium polium L. subsp. polium. Acta Soc Bot Pol. 81:117–122. Twaij HA, Albadr AA, Abul-Khail A. 1987. Anti-ulcer activity of Teucrium polium. Int J Crude Drug Res. 25:125–128. Ulubelen A, Topu G, Sönmez U. 2000. Chemical and biological evaluation of genus Teucrium. Stud Nat Prod Chem. 23:591–648. Zorzetto C, Sánchez-Mateo CC, Rabanal RM, Lupidi G, Bramucci M, Quassinti L, Iannarelli R, Papa F, Maggi F. 2015. Antioxidant activity and cytotoxicity on tumour cells of the essential oil from Cedronella canariensis var. canariensis (L.) Webb & Berthel. (Lamiaceae). Nat Prod Res. 29:1641–1649.
