Phytochemical study of Zataria multiflora Boiss in different ecological conditions

Subject Areas : Journal of Plant Ecophysiology

Ahmad Niczad ¹ (PhD Student of Agronomy, Faculty of Agriculture, Firoozabad Branch, Islamic Azad University, Firoozabad, Iran.)
Shahram Sharafzadeh ² (Associated Professor, Department of Agronomy, Faculty of Agriculture, Firoozabad Branch, Islamic Azad University, Firoozabad, Iran.)
Ardalan Alizadeh ³ (استادیار، گروه گیاهان دارویی و معطر، دانشکده کشاورزی، واحد استهبان، دانشگاه آزاد اسلامی، استهبان، ایران)
Bahram Amiri ⁴ (Department of Agronomy, Azad university , Firouzabad)
Forood Bazrafshan ⁵ (Assisstant Professor, Department of Agronomy, Faculty of Agriculture, Firoozabad Branch, Islamic Azad University, Firoozabad, Iran)

Received: 2020-07-09 Accepted : 2020-12-22 Published : 2021-04-21

Keywords: Zataria multiflora, Phenolic content, antioxidant activity, Essential oil, different ecotypes,

Abstract :

In the present study, 4 different ecotypes of Zataria multiflora medicinal plant (Estahban, Neyriz, Fasa and Larestan), were investigated in order to identify the best ecotype in terms of the highest percentage of essential oil, essential oil components, total phenolic content, antioxidant properties and polyphenolic compounds of methanolic extract. Essential oils were extracted from all ecotypes by hydro-distillation via Clevenger apparatus, then analyzed using gas chromatography (GC) and gas chromatograph connected to mass spectrophotometer (GC/MS) . In total, 52 compounds were identified in the essential oils of different ecotypes of Zataria multiflora. The main chemical constituents were, thymol (34.41 - 54.35 %), p-cymene (9.49 - 19.85 %), -Terpinene (7.34 - 16.70 %) and carvacrol (5.35 - 15.34 %). Determination of total phenol and antioxidant activity of methanolic extract were determined using the Folin-Ciocalteau reagent and by the 2, 2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging assay, respectively. Polyphenolic components of extracts of different ecotypes were determined using high performance liquid chromatography (HPLC). Total phenols varied from 234.66 to 302.28 mg gallic acid equivalents/g dry weight, IC50 values in the radical scavenging assay ranged from 348.63 to 453.76 mg/mL. The predominant polyphenolic compounds in the extracts of all ecotypes included: Thymol, Carvacrol, Quercetin and Rosmarinic acid. The results showed that Neyriz ecotype has the highest percentage of essential oil and the highest percentage of thymol. The highest amount of phenolic compounds and antioxidant activity was observed in Larestan ecotype. The predominant polyphenolic component was thymol and was observed in the Fasa ecotype.

References:

Adams, RP. 2007. Identification of essential oil components by gas chromatography/ mass spectroscopy. Allured Publishing Corporation, Illinois, USA, 1–804.

Andrade, EHA., CN. Alves, EF. Guimaraes, LMM. Carreira and JGS. Maia. 2011. Variability in essential oil composition of Piper dilatatum LC Rich. Biochem Syst Ecol. 39(4): 669-75.

Alizadeh, A. 2013. Essential oil constituents, antioxidant and antimicrobial activities of Salvia virgata Jacq. from Iran, J. Essen. Oil Bearing Plants. 16: 172-182.

Alizadeh, A. and M. Shaabani. 2014. Essential oil composition, total phenolic content and antioxidant activities of Iranian Zataria multiflora Boiss. International Journal Biosciences. 4(4): p. 1-8.

Alizadeh, A. 2015. Essential oil composition, phenolic content, antioxidant, and antimicrobial activity of cultivated Satureja rechingeri Jamzad at different phenological stages, Z. Naturforsch C. 70(3-4): 51-58.

Alizadeh, A. 2016. Essential oil constituents and biological activities of different ecotypes of Satureja bachtiarica Bunge. as a traditional herbal drug in Southwestern Iran, J. Essent. Oil Bearing Plants. 19(6):1328-1339.

Alizadeh, A. and Z. Aghaee. 2016. Essential oil constituents, phenolic content and antioxidant activity of Lavandula stricta Delile growing wild in southern Iran. Nat.Prod. Res. 30: 2253–2257.

Brand-Williams, W., M.E.  Cuvelier, and C. Berset. 1995. Use of a free radical method to evaluate antioxidant activity. Lebenson Wiss Tech. 28:25-30.

Duncan, D.B. 1955. Multiple range and Multiple F-tests. Biometrics, (2-4): 1-42.

Fatima, A. Ahmad, K. and H. Ali Chokr. 2012. Factors affecting quantitative and qualitative variation of thyme (Origanum syriacum L.) essential oil in Lebanon. Adv. Environ. Bio. 6(4): 1509-1514.

Fazeli, MR., G. Amin, M.M. Ahmadian Attari, H. Ashtiani, H. Jamalifar and N. Samadi. 2007. Antimicrobial activities of Iranian sumac and Avishan-e-Shirazi (Zataria multiflora) against some food borne bacteria. Food Control. 18: 646-649.

Feyzi, P., H. Kamali, A. Yazdani and H. Hashemimoghadam. 2012. Comparison of solvent extraction and hydrodistillation of essential oil from Biebersteinia multifida DC. Conjunction with gas chromatography – mass spectroscopy. Journal of North Khorasan University of Medical Sciences. (Natural Products & Medicinal Plants Supplementary). 4: 35-41.

Gassemi Pirbalouti, A. Rahimmalek, M.  Malekpoor, F. and A. Karimi. 2011. Variation in antibacterial activity, thymol and carvacrol contents of wild populations of Thymus daenensis subsp. daenensis Celak. Plant Omics.4: 209-214.

Gharibi, S.H., S.E. Badraldin Tabatabaei, G.H. Saeidi, S.A.H. Goli, and M. Talebi. 2013. Total phenolic content and antioxidant activity of three Iranian endemic Achillea species, Ind. Crops Prod. 50: 154-158.

Golkar, P, N. Mosavat and S.A.H. Jalali. 2020. Essential oils, chemical constituents, antioxidant, anti-bacterial and in vitro cytotoxic activity of different Thymus species and Zataria multiflora collected from Iran. S. Afr. J. Bot. 130: 250-258.

Hosseinzadeh, H., M. Ramezani, and G. Salmani. 2000. Antinociceptive, anti-inflammatory and acute toxicity effects of Zataria multifora Boiss extracts in mice and rats. J. Ethnopharm. 73(3):379-385.

Institute of Standards and Industrial Research of Iran. Determination of biophenols in olive oils by HPLC. no16323. 1st. Edition, Karaj: ISIRI.  2013. in Persian.

Jaffery, E.H, A.F. Brown, A.C. Kurilich, A.S. Keck, N. Matusheski, B.P. Klein and  J.A. Juvik. 2003. Variation in content of bioactive components in broccoli, J. Food Compos. Anal. 16: 323-330.

Jamshidi, M., HR. Ahmadi Ashtiani, Sh. A. Rezazadeh, F. Azad, M. Mazandarani and A. Khaki. 2010.  A.Study on phenolic and antioxidant activity of some selected plant of Mazandaran Province. Journal of medicinal Plant. 9(34): 177-183.

Jamzad, Z. 2009. Thyme and Savory of Iran. Institute of Forest and Rangelands. Tehran, 172p.

Karimi, A, A. Krähmer, N. Herwig, H. Schulz, J. Hadian, and T. Meiners. 2020. Variation of secondary metabolite profile of Zataria multiflora Boiss. populations linked to geographic, climatic, and edaphic factors. Front. Plant. Sci. 11.

Kizil, S. 2010. Determination of essential oil variations of Thymbra spicata var spicata L. naturally growing in the wild flora of East Mediterranean and Southeastern Anatolia regions of Turkey. Ind. Crops Prod. 32(3): 593-600.

Koochaki, A. and M. Alizadeh. 1995. Principle of agronomy in dry regions. Astan Quds Razavi. 260 pp.

Kukic, J., V. Popovic, S. Petrovic, P. Mucaji, A. Ciric, D. Stojkovic. and M. Sokovi. 2008. Antioxidant and antimicrobial activity of Cynara cardunculus extracts Food Chemistry, 107: 861 – 868.

Leporatti, M.L. and K. Ghedira. 2009. Comparative analysis of medicinal plants used in traditional medicine in Italy and Tunisia. J Ethnobiol. Ethnomed. 5: 31-39.

Mabberley, DJ. 1997. The plant -Book 2nd ed .400 Cambridge, Cambridge university press. 384 p.

Mahboubi, M., R. Heidarytabar, E. Mehdizadeh and H. Hosseini. 2017. Antimicrobial activity and chemical composition of Thymus species and Zataria multiflora essential oils. Agriculture and Natural Resources. 51: 395-401.

Mc Gimpsey, J. A. Douglas, M.H. Van Klink, J.W. Beauregard, D.A. and N.B. Perry. 1994. Seasonal variation in essential oil yield and composition from naturalized Thymus vulgais L. in New Zealand. Flav. Frag. J. 9: 347-35.

Mojaddar Langroodi, A., H. Tajik and T. Mehdizadeh. 2019. Antibacterial and antioxidant characteristics of Zataria multiflora Boiss essential oil and hydroalcoholic extract of Rhus coriaria L. J. Food Qual. Hazards Control. 6(1): 16-24.

Mohagheghzadeh, A., M. Shams-Ardakani, A. Ghannadi and M. Minaeian. 2004. Rosmarinic acid from Zataria multiflora tops and in vitro cultures. Fitoterapia. 75. Pp. 315-21.

Moraes de souza, R. A., TLC. Oldoni, D. Regitano MAB. Arce and SM. Alencar.  2008. Antioxidant activity and phenolic composition of herbal infusions consumed in Brazil. Ciencia Tecnololia de Alimentos 2008; 6(1): 41-7.

Niczad, A., Sh. Sharafzadeh, A. Alizadeh, B. Amiri, and F. Bazrafshan. 2020. Variability in Essential Oil Constituent, Phenolic Content, Antioxidant and Antimicrobial Activities of Different Ecotypes of Zataria multiflora Boiss. from Iran. Journal of Essential Oil-Bearing Plants. Taylor and Francis group. 22(6). Pp: 1435-1449.

Nantitanon, W., S. Yotsawimonwat and S. Okonogi. 2010. Factors influencing antioxidant activities and total phenolic content of guava leaf extract. LWT–Food Sci. Technol. 43: 1095–1103.

Omidbaigi, R. 2005.  Production and Processing of medicinal plants. Tehran University. 283 Pp.

Purmorad, F., S. J. Hossinimehr and N. Shahabimajd. 2006. Antioxidant activity phenol and flavonoid contents of some selected Iranian medicinal plants. Afr. J. Biotech. 5(11):1142-1145.

Pourhosseini, S.H, M.H. Mirjalili, S.N. Ebrahimi and A. Sonboli. 2018. Essential oil quantity and quality of different plant organs from Perovskia abrotanoides Karel in natural habitat of North Khorasan province. The Plant Prod. 40: 53-62.

Pourhosseini, S. H., H. Ahadi, A. Aliahmadi and M. H. Mirjalili. 2020. Chemical Composition and Antibacterial Activity of the Carvacrol-rich Essential Oils of Zataria multiflora Boiss. (Lamiaceae) from Southern Natural Habitats of Iran. Journal of Essential Oil-Bearing Plants. Taylor and Francis group. 23(4). Pp: 779-787.

Raeisi, M., H. Tajik, S.M. Razavi Rohani, B. Tepe, H. Kiani, R. Khoshbakht, H.Sh. Aski and H. Tadrisi. 2016. Inhibitory effect of Zataria multiflora Boiss. Essential oil, alone and in combination with monolaurin, on Listeria monocytogenes. Veterinary Res. 7 (1): 7 – 11.

Raeisi, M., M. Hashemi, M. Aminzare, A. Afshari, T. Zeinali and B. Jannat. 2018. An investigation of the effect of Zataria multiflora Boiss and Mentha piperita essential oils to improvethe chemical stability of minced meat, Vet. World. 11(12): 1656–1662.

Rahimi, V., SH. Hekmatimoghadam, A. Jebali and E. Khalili Sadrabad. 2019. Chemical composition and antifungal activity of essential oil of Zataria multiflora. Journal of Nutrition and Food Security. 4(1): 1-6.

Rastegar, F., S. Moharamipour, M. Shojaei and H. Abbasipour. 2011. Chemical composition and insecticidal activity of essential oil of Zataria multiflora. (Lamiaceae) against Callosobruchus maculates (F.) (Coleoptera: Bruchidae). J. Integrated protection of Stored. 69: 281-288.

Rechinger, K.H. 1982. Flora Iranica. No.150, Graz: Akademisch Druck-u.Verlagsanstal; pp. 403-476.

Rice-Evans, C.A., N. J. Miller and G. Paganga. 1997. Antioxidant properties of phenolic compounds. Trends Plant Sci. 2:152–159.

Saei-Dehkordi, S.S., H. Tajik, M. Moradi and F. Khalighi-Sigaroodi. 2010. Chemical composition of essential oils in Zataria multiflora Boiss. From different parts of Iran and their radical scavenging and antimicrobial activity. Food Chem. Toxicol. 48: 1562-1567.

Saez, F. 1998. Variability in essential oils from populations of Thymus hymalis Lange in southeasten Spain. J. Herbs, Spices Med. Plants. 5: 65-76.

Sadeghi, F., A. Alizadeh, M. Zadehbagheri, M. Kamelmanesh, and M. Shabani. 2012. Chemical composition of essential oil, total phenolic content, antioxidant and antifungal activity in Satureja sahendica Bornm. from Iran, J. Med. Plant Res. 6: 3525-3534.

Saharkhiz, M. J. 2002. Effect of harvesting time on Pimpinella anisum essential oil and components. M.Sc. thesis. Faculty of Agriculture, University of Tarbiat Modarres, Iran. (in Farsi).

Sharafati Chaleshtori, R., M. Rafieian-Kopaei, N. Rokni, S. Mortazaei and A. Sharafati Chaleshtori. 2013. Antioxidant activity of Zataria multiflora hydroalcoholic extract and its antibacterial effect on Staphylococcus aureus, J. Mazandaran Uni. Med Sci. 22:87-94.

Sharififar, F., M.H. Moshafi S.H. Mansouri and M. Khodashenas. 2007. In vitro evaluation of antibacterial and antioxidant activities of the essential oil and methanol extract of endemic Zataria multiflora Boiss. Food control. Pp. 18, 800-805.

Shafiee, A. and K. Javidnia. 1997. Composition of essential oil of Zataria multiflora. Planta Med. 63: 371-372.

Singleton, V.L. and J.A. Rossi. 1965. Colorimetry of total phenolic with phosphomolybdic phosphotungesicacid reagents, Amer. J. Enol. Vitic. 16: 144-158.

Talebi Kouyakhi, E. Naghavi, M.R. and M. Alaysh. 2008. Study of the essential oil variation of Ferula gummosa samples from Iran. Chem. Nat. Com. 44(1): 124-126.

Valizadeh, J., A. Bagheri, J. Valizadeh, and M.H. Mirjalili. 2015. Phytochemical investigation of Withania coagulans (Stocks) Dunal in natural habits of Sistan and Baluchestan. Province of Iran. Iranian Journal of medical and aromatics plants. 31(3): 406-417.

Wang, M., J. Li, M. Rangarajan, Y. Shao, E.J. La Voie, C.T. Huang, and CT. Ho. 1998. Antioxidative phenolic compounds from sage (Salvia officinalis). J. Agri. Food Chem. 46: 4869-4873.

Wong, C. C., H. B. Li, K. W. Cheng and F. Chen. 2006. A systematic survey of antioxidant activity of 30 Chinese medicinal plants using the ferric reducing antioxidant power assay. Food Chem. 97:705-711.