Chemical constituents, quantitative analysis and insecticidal activities of plant extract and essential oil from Origanum onites L.

Document Type: Original Article

Authors

1 Department of Chemistry, Faculty of Arts and Sciences, Gaziosmanpasa University, 60240 Tokat, Turkey

2 Department of Chemistry, Faculty of Natural Sciences, Cankiri Karatekin University, 18200, Cankiri, Turkey

3 Department of Biology, Faculty of Arts and Sciences, Gaziosmanpasa University, 60240 Tokat, Turkey

4 Department of Chemistry, Scientific Technical Application and Research Center, Hitit University, 19030 Çorum, Turkey

5 Department of Crop and Animal Protection, Yaprakli Vocational School, Cankiri Karatekin University, 18100 Cankiri, Turkey

Abstract

Origanum, widely used for food and pharmaceutical industry, belonging to the Lamiaceae family, is an aromatic and medicinal plant. The aerial parts of the Origanum onites L. were dried at shade and was extracted with methanol. Rosmarinic acid, gentisic acid, 4-hydroxybenzoic acid, protocatechuic acid, caffeic acid, vanillic acid, 4-hydroxylbenzaldehyde, p-cumaric acid, ferullic acid, apigenin-7-glucoside, and narigenin were found in O. onites methanol extract. Quantitative analyses of these compounds were determined by LC-TOF/MS and rosmarinic acid was the main constituent (32.05 mg/100 g dried plant). The essential oil was isolated by steam distillation and compounds were identified by GC-MS analysis. The essential oil included the carvacrol (88.71%) as a main product. p-Cymene (3.09%) was found as a second chief product. The essential oil exhibited excellent insecticidal activity on Sitophilus granaries and Sitophilus oryzae pests. However, methanol extract revealed the moderate activity on S. granarius pet.

Graphical Abstract

Chemical constituents, quantitative analysis and insecticidal activities of plant extract and essential oil from Origanum onites L.

Keywords

Main Subjects


Abay, G., Karakoc, O.C., Tufekci, A.R., Koldas, S., Demirtas, I., 2012. Insecticidal activity of Hypnum cupressiforme (Bryophyta) against Sitophilus granarius (Coleoptera: Curculionidae). J. Stored Prod. Res. 51, 6-10.

 Aeschbach, R., Löliger, J., Scott, B., Murcia, A., Butler, J., Halliwell, B., Aruoma, O., 1994. Antioxidant actions of thymol, carvacrol, 6-gingerol, zingerone and hydroxytyrosol. Food Chem. Toxicol. 32(1), 31-36.

 Aksit, H., Celik, S.M., Sen, O., Erenler, R., Demirtas, I., Telci, I., Elmastas, M., 2014. Complete isolation and characterization of polar portion of Mentha dumetorum water extract. Rec. Nat. Prod. 8(3), 277-280.

 Bagamboula, C., Uyttendaele, M., Debevere, J., 2004. Inhibitory effect of thyme and basil essential oils, carvacrol, thymol, estragol, linalool and p-cymene towards Shigella sonnei and S. flexneri. Food Microbiol. 21(1), 33-42.

 Bagci, Y., Saadia, Z., Özcan, M.M., 2005. Aroma profile of Origanum vulgare L. subsp. viride (Boiss.) Hayek, Satureja hortensis L. and Thymbra sintenisii Bornm. & Aznav. subsp. isaurica PH Davis used as condiment and herbal tea in Turkey. J. Essent. Oil. Bear. Plants 8(3), 304-311.

 Bakkali, F., Averbeck, S., Averbeck, D., Waomar, M., 2008. Biological effects of essential oils - A review. Food Chem. Toxicol. 46(2), 446-475.

 Busatta, C., Vidal, R.S., Popiolski, A.S., Mossi, A.J., Dariva, C., Rodrigues, M.R.A., Corazza, F.C., Corazza, M.L., Oliveira, J.V., Cansian, R.L., 2008. Application of Origanum majorana L. essential oil as an antimicrobial agent in sausage. Food Microbiol. 25(1), 207-211.

 Camilo, C.J., Nonato, C.D.F.A., Galvão-Rodrigues, F.F., Costa, W.D., Clemente, G.G., Macedo, M.a.C.S., Rodrigues, F.F.G., Martins Da Costa, J.G., 2017. Acaricidal activity of essential oils: a review. Trends Phytochem. Res. 1(4), 183-198.

 Demirtas, I., Erenler, R., Elmastas, M., Goktasoglu, A., 2013. Studies on the antioxidant potential of flavones of Allium vineale isolated from its water-soluble fraction. Food Chem. 136(1), 34-40.

 Duman, H., 2000. Origanum L., in: Güner, A., Özhatay, N., Ekim, T., Baser, K.H.C. (Eds.), Flora of Turkey and the East Aegean Islands. Supplement 2, University Press, Edinburgh, UK., p. 207.

 Edde, P.A., 2012. A review of the biology and control of Rhyzopertha dominica (F.) the lesser grain borer. J. Stored Prod. Res. 48, 1-18.

 Elmastas, M., Erenler, R., Isnac, B., Aksit, H., Sen, O., Genc, N., Demirtas, I., 2016. Isolation and identification of a new neo-clerodane diterpenoid from Teucrium chamaedrys L. Nat. Prod. Res. 30(3), 299-304.

 Elmastas, M., Ozturk, L., Gokce, I., Erenler, R., Aboul-Enein, H.Y., 2004. Determination of antioxidant activity of marshmallow flower (Althaea officinalis L.). Anal. Lett. 37(9), 1859-1869.

 Erenler, R., Adak, T., Karan, T., Elmastas, M., Yildiz, I., Aksit, H., Topcu, G., Sanda, M.A., 2017a. Chemical constituents isolated from Origanum solymicum with antioxidant activities. Eur. Proceed. Sci. Tec. Eng. Math. 139-145.

 Erenler, R., Meral, B., Sen, O., Elmastas, M., Aydin, A., Eminagaoglu, O., Topcu, G., 2017b. Bioassay-guided isolation, identification of compounds from Origanum rotundifolium and investigation of their antiproliferative and antioxidant activities. Pharm. Biol. 55(1), 1646-1653.

 Erenler, R., Sen, O., Aksit, H., Demirtas, I., Yaglioglu, A.S., Elmastas, M., Telci, İ., 2016. Isolation and identification of chemical constituents from Origanum majorana and investigation of antiproliferative and antioxidant activities. J. Sci. Food Agric. 96(3), 822-836.

 Erenler, R., Telci, I., Ulutas, M., Demirtas, I., Gul, F., Elmastas, M., Kayir, O., 2015. Chemical constituents, quantitative analysis and antioxidant activities of Echinacea purpurea (L.) Moench and Echinacea pallida (Nutt.) Nutt. J. Food Biochem. 39(5), 622-630.

 Erenler, R., Yilmaz, S., Aksit, H., Sen, O., Genc, N., Elmastas, M., Demirtas, I., 2014. Antioxidant activities of chemical constituents isolated from Echinops orientalis Trauv. Rec. Nat. Prod. 8(1), 32-36.

 Ganesan, K., Xu, B., 2017. Ethnobotanical studies on folkloric medicinal plants in Nainamalai, Namakkal District, Tamil Nadu, India. Trends Phytochem. Res. 1(3), 153-168.

 Huang, Y., Lam, S.L., Ho, S.H., 2000. Bioactivities of essential oil from Elletaria cardamomum (L.) Maton. to Sitophilus zeamais Motschulsky and Tribolium castaneum (Herbst). J. Stored Prod. Res. 36(2), 107-117.

 Karan, T., Simsek, S., Yildiz, I., Erenler, R., 2018. Chemical composition and insecticidal activity of Origanum syriacum L. essential oil against Sitophilus oryzae and Rhyzopertha dominica. Int. J. Sec. Metab. 5(2), 87-93.

 Kordali, S., Cakir, A., Ozer, H., Cakmakci, R., Kesdek, M., Mete, E., 2008. Antifungal, phytotoxic and insecticidal properties of essential oil isolated from Turkish Origanum acutidens and its three components, carvacrol, thymol and p-cymene. Bioresource Technol. 99(18), 8788-8795.

 Koutsaviti, A., Antonopoulou, V., Vlassi, A., Antonatos, S., Michaelakis, A., Papachristos, D.P., Tzakou, O., 2018. Chemical composition and fumigant activity of essential oils from six plant families against Sitophilus oryzae (Col: Curculionidae). J. Pest Sci. 91(2), 873-886.

 Mohammadhosseini, M., 2017a. Essential oils extracted using microwave-assisted hydrodistillation from aerial parts of eleven Artemisia species: Chemical compositions and diversities in different geographical regions of Iran. Rec. Nat. Prod. 11(2), 114-129.

 Mohammadhosseini, M., 2017b. The ethnobotanical, phytochemical and pharmacological properties and medicinal applications of essential oils and extracts of different Ziziphora species. Ind. Crops Prod. 105, 164-192.

 Mohammadhosseini, M., Akbarzadeh, A., Hashemi-Moghaddam, H., Nafchi, A.M., Mashayekhi, H.A., Aryanpour, A., 2016. Chemical composition of the essential oils from the aerial parts of Artemisia sieberi by using conventional hydrodistillation and microwave assisted hydrodistillation: A comparative study. J. Essent. Oil. Bear. Plants 19(1), 32-45.

 Mohammadhosseini, M., Sarker, S.D., Akbarzadeh, A., 2017. Chemical composition of the essential oils and extracts of Achillea species and their biological activities: A review. J. Ethnopharmacol. 199, 257-315.

 Monteiro, I.N., Dos Santos Monteiro, O., Costa-Junior, L.M., Da Silva Lima, A., De Aguiar Andrade, E.H., Maia, J.G.S., Mouchrek Filho, V.E., 2017. Chemical composition and acaricide activity of an essential oil from a rare chemotype of Cinnamomum verum Presl on Rhipicephalus microplus (Acari: Ixodidae). Vet. Parasitol. 238, 54-57.

 Nunes, H., Miguel, M.G., 2017. Rosa damascena essential oils: a brief review about chemical composition and biological properties. Trends Phytochem. Res. 1(3), 111-128.

 Oka, Y., Nacar, S., Putievsky, E., Ravid, U., Yaniv, Z., Spiegel, Y., 2000. Nematicidal activity of essential oils and their components against the root-knot nematode. Phytopathology 90(7), 710-715.

 Ozcan, M.M., Chalchat, J.C., 2009. Chemical composition and antimicrobial properties of the essential oil of Origanum saccatum L. J. Food Saf. 29(4), 617-628.

 Ozkan, G., Baydar, H., Erbas, S., 2010. The influence of harvest time on essential oil composition, phenolic constituents and antioxidant properties of Turkish oregano (Origanum onites L.). J. Sci. Food Agric. 90(2), 205-209.

 Özcan, M.M., Arslan, D., Aydar, A.O., 2008. The use of the oregano (Origanum vulgare L.) essential oil and hydrosol in green olive fermentation. Braz. Arch. Biol. Tech. 51(3), 601-605.

 Özcan, M.M., Özkan, G., Sagdıc, O., 2015. Antibacterial effects of Istanbul thyme (Origanum vulgare L. subsp. hirtum (Link) Ietsw.) and Karabas thyme (Thymbra spicata L. var. spicata) extracts. Arch. Lebensmittelhyg 66, 177-181.

 Park, B.S., Lee, S.E., Choi, W.S., Jeong, C.Y., Song, C., Cho, K.Y., 2002. Insecticidal and acaricidal activity of pipernonaline and piperoctadecalidine derived from dried fruits of Piper longum L. Crop Protect. 21(3), 249-251.

 Pavunraj, M., Ramasubbu, G., Baskar, K., 2017. Leucas aspera (willd.) L.: Antibacterial, antifungal and mosquitocidal activities. Trends Phytochem. Res. 1(3), 135-142.

 Piasecka-Kwiatkowska, D., Nawrot, J., Zielińska-Dawidziak, M., Gawlak, M., Michalak, M., 2014. Detection of grain infestation caused by the granary weevil (Sitophilus granarius L.) using zymography for α-amylase activity. J. Stored Prod. Res. 56, 43-48.

 Shaaban, H.a.E., El-Ghorab, A.H., Shibamoto, T., 2012. Bioactivity of essential oils and their volatile aroma components: Review. J. Essent. Oil Res. 24(2), 203-212.

 Sundararajan, G., Kumuthakalavalli, R., 2001. Antifeedant activity of aqueous extract of Gnidia glauca Gilg. and Toddalia asiatica Lam. on the gram pod borer, Helicoverpa armigera (Hbn). J. Environ. Biol. 22(1), 11-14.

 Ultee, A., Slump, R., Steging, G., Smid, E., 2000. Antimicrobial activity of carvacrol toward Bacillus cereus on rice. J. Food Protect. 63(5), 620-624.

 Wakim, L.H., El Beyrouthy, M., Mnif, W., Dhifi, W., Salman, M., Bassal, A., 2013. Influence of drying conditions on the quality of Origanum syriacum L. Nat. Prod. Res. 27(15), 1378-1387.

 Yildirim, I., Ozsan, M., Yetisir, R., 2003. The use of oregano (Origanum vulgare L) essential oil as alternative hatching egg disinfectant versus formaldehyde fumigation in quails (Coturnix coturnix japonica). Revue méd. vétér.154(5), 367-370.