Chemical composition of essential oil by SPME and evaulation antimicrobial, antioxidant activities of medicinal plant of Quercus infectoria galls

Sule Ceylan

Artvin Coruh University, Faculty of Forestry, Department of Forest Industry Engineering, 08000, Artvin, Turkey

Şehmuz Semih Yardımcı

Artvin Coruh University, Faculty of Forestry, Department of Forest Industry Engineering, 08000, Artvin, Turkey

Yasemin Camadan

Artvin Coruh University, Vocational School of Health Services, Pharmacy Services, 08000, Artvin, Turkey

Özlem Saral

Recep Tayyip Erdogan University, College of Health, Department of Nutrition and Dietetics, 53100, Rize, Turkey

Özge Özsen Batur

Eskisehir Osmangazi University, Department of Chemistry, 26480 Eskisehir, Turkey


Abstract

Quercus infectoria galls have been utilized to cure widespread illnesses. In line with it, this paper aims to investigate the chemical combination of the volatile oils obtained from galls of Q. infectoria and evaluate their antioxidant and antimicrobial features. The volatiles of Q. infectoria has been isolated by solid-phase microextraction (SPME). The compositions of the volatiles were revealed via gas chromatography coupled with mass spectrometry (GC-MS). Twenty-nine substances have been characterized in the volatile essential oil of Q. infectoria. The major components of the volatile oil were (Z)-Anethol 28.55%, pentadecanolide (26.44%), diethyl phthalate (6.46%), and acetoin (5.66%). Q. infectoria showed good-moderate antimicrobial (Staphylococcus aureus, Streptomyces griseolus, Pseudomonas citronellosis) and antifungal (Candida glabrata, Candida krusei) activities against to test microorganisms with MIC value 250 µg/mL and 125 µg/mL, respectively. Also, total flavonoid and total polyphenol amounts were found for Q. infectoria, and our total polyphenol result (342.87 mg GAE/g) was found higher than the studies in the literature. At the same time Q. infectoria has been observed to have high antioxidant activity according to DPPH, FRAP, and CUPRAC assays. Especially it exhibited excellent DPPH activity for the IC50 rate of 0.002 μg/mL which is higher than the standard Trolox (IC50 = 0.008 μg/mL). This study is important because it is the first one, which reports the determination of essential oil, total polyphenol, flavonoid contents, antioxidant, and antimicrobial activities all together for Q. infectoria.

Keywords:

Quercus infectoria, GC-MS, SPME, volatile oil, antioxidant, antimicrobial

Ahmad, W., Zeenat, F., Hasan, A., Abdullah, A., Nargis, A., Tarannum, A. (2011). Mazu (Quercus infectoria, Oliv) – an overview. Ind. J. Unani. Med., 4(1), 17–22.

Amsterdam, D. (1996). Susceptibility testing of antimicrobials in liquid media. In: Antibiotics in Laboratory Medicine, V. Lorian (ed.). 4th ed. Williams Wilkins, Baltimore.

Apak, R., Güçlü, K., Özyürek, M., Karademir, S.E. (2004). Novel total antioxidant capacity index for dietary polyphenols and vitamins C and E, using their cupric ion reducing capability in the presence of neocuproine: cuprac method. J. Agric. Food Chem., 52, 7970–7981.

Basri, D.F., Fan, S.H. (2005). The potential of aqueous and acetone extracts of galls of Quercus infectoria as antibacterial agents. Ind. J. Pharmacol., 37, 26–29.

Benzie, I.F., Szeto, Y.T. (1999). Total antioxidant capacity of teas by the ferric reducing/antioxidant power assay. J. Agric. Food Chem., 47, 633–636.

Burlacu, E., Nisca, A., Tanase, C. (2020). A comprehensive review of phytochemistry and biological activities of Quercus species. Forests, 11(9), 904.

Ceylan, S., Cetin, S., Camadan, Y., Saral, O., Ozsen, O., Tutus, A. (2009). Antibacterial and antioxidant activities of traditional medicinal plants from the Erzurum region of Turkey. Irish J. Med. Sci. 188, 1303–1309.

Chang, C.C., Yang, M.H., Wen, H.M., Chern, J.C. (2002). Estimation of total flavonoid content in propolis by two complementary colorimetric methods. J. Food Drug. Anal., 10, 178–182.

CLSI. (2002). Reference method for broth dilution antifungal susceptibility testing of yeast. Approved standard. 2nd ed. CLSI document M27-A2. Clinical and Laboratory Standards Institute, Wayne, PA.

CLSI. (2006). Performance standards for antimicrobial susceptibility testing, sixteenth ınformational supplement, CLSI document M100-S16. Clinical and Laboratory Standards Institute,Wayne, PA.

Dar, M.S., Ikram, M., Fakouhi, T. (1976). Pharmacology of Quercus infectoria. J. Pharm. Sci., 65, 1791–1794.

Fathabad, A.E., Shariatifar, N., Mardani, K., Mohammadpourfard, I. (2015). Study on antibacterial and antioxidant activity of Oak gall (Quercus infectoria) extracts from Iran. Int. J. Curr. Sci., 14, 44–50.

FFNSC. GC/MS Library Ver.1.3 (2008). Flavor and fragrance natural and synthetic compounds. Shimadzu, Kyoto, Japan.

Gholamreza, K., Asad, T., Ali, A.E., Vahid, R. (2013). Evaluation of antioxidant and antimicrobial activities of essential oils from Carum copticum seed and ferula assafoetida latex. J. Food Sci., 78(2), T356–T361.

Halliwell, B., Gutteridge, J.M.C., Cross, C.E. (1992). Free radicals, antioxidants, and human disease: where are we now? J. Lab. Clin. Med., 119, 598–620.

Hamad, H.O., Alma, M.H., Gulcin, İ., Yılmaz, M.A., Karaoğul, E. (2017). Evaluation of Phenolic contents and bioactivity of root and nutgall extracts from Iraqian Quercus infectoria Olivier. Rec. Nat. Prod., 11(2), 205–210.

Hasmida, M.N., Nur Syukriah, A.R., Liza, M.S., Mohd, Azizi, C.Y. (2014). Effect of different extraction techniques on total phenolic content and antioxidant activity of Quercus infectoria galls. Internat. Food Res. J., 21(3), 1039–1043.

Homayonpour, P., Jalali, H., Shariatifar, N., Amanlou, M. (2021). Effects of nano-chitosan coatings incorporating with free /nano-encapsulated cumin (Cuminum cyminum L.) essential oil on quality characteristics of sardine fillet. Int. J. Food Microbiol., 341, 109047.

Hussein, A.O., Mohammed, G.J., Hadi, M.Y., Hameed, I.H. (2016). Phytochemical screening of methanolic dried galls extract of Quercus infectoria using gas chromatography-mass spectrometry (GC-MS) and Fourier transform-infrared (FT-IR). J. Pharmacogn. Phytother., 8(3), 49–59.

Iminjan, M., Amat, N., Li, X.H., Upur, H., Ahmat, D., He, B. (2014) Investigation into the toxicity of traditional Uyghur medicine Quercus infectoria galls water extract. PLoS One., 9(3), e90756.

Iylia Arina, M.Z., Harisun, Y. (2019). Effect of extraction temperatures on tannin content and antioxidant activity of Quercus infectoria (Manjakani). Biocatal. Agricult. Biotechnol., 19, 101104.

Jamzad, Z., Panahi, P., Mohammad, R.P., Fallha, A.M. (2012). Foliar epidermal morphology in Quercus (subgenus Quercus: section Quercus) in Iran. Acta Bot. Croat. 71, 95–113.

Kamkar, A., Ardekani, M.R.S., Shariatifar, N., Misagi, A., Nejad, A.S.M., Jamshidi, A.H. (2013). Antioxidative effect of Iranian Pulicaria gnaphalodes L. extracts in soybean oil. South Afr. J. Bot., 85, 39–43.

Katalinic, V., Milos, M., Kulisic, T., Jukic, M. (2006). Sceerning of 70 medical plant extracts for antioxidant capacity and total phenols. Food Chem., 94, 550–557.

Kaur, G., Athar, M., Alam, S. (2008). Quercus infectoria galls possess antioxidant activity and abrogates oxidative stress-induced functional alterations in murine macrophages. Chemico-Biological Interactions., 171(3), 272–282.

Kheirandish, F., Delfan, B., Mahmoudvand, H., Moradi, N., Ezatpour, B., Ebrahimzadeh, F., Rashidipourd, M. (2016). Antileishmanial, antioxidant, and cytotoxic activities of Quercus infectoria Olivier extract. Biomed. Pharmacother., 82, 208–215.

Kordali, S., Kotan, R., Mavi, A., Cakir, A., Ala, A., Yildirim, A. (2005). Determination of the chemical composition and antioxidant activity of the essential oil of Artemisia dracunculus and of the antifungal and antibacterial activities of Turkish Artemisia absinthium, Artemisia dracunculus, Artemisia santonicum, and Artemisia spicigera essential oils. J. Agric. Food Chem., 53(24), 52–59.

Kovats, E. (1958). Gas-chromatographische Charakterisierung organischer Verbindungen. Teil 1: I. Retentionsindices aliphatischer Halogenide, Alkohole, Aldehyde und Ketone. Helvetica Chim. Acta., 41, 1915–1932.

Leela, T., Satirapipathkul, C. (2011). Studies on the antibacterial activity of Quercus Infectoria galls. International Conference on Bioscience. Biochemistry and Bioinformatics IPCBEE, IACSIT Press, Singapore, 5.

Lopes-Lutz, D., Alviano, D.S., Alviano, C.S., Kolodziejczyk, P.P. (2008) Screening of chemical composition, antimicrobial and antioxidant activities of Artemisia essential oils. Phytochem., 2, 1–14.

Lucera, A., Costa, C., Conte, A., Del Nobile, M.A. (2012). Food applications of natural antimicrobial compounds. Front Microbiol., 3, 287.

Lund, B.M., O’Brien, S.J. (2011). The occurrence and prevention of foodborne disease in vulnerable people. Foodborne Pathog. Dis., 8(9), 961–973.

Madhavi, D.L., Salunkhe, D.K. (1995) Toxicological aspects of food antioxidants. In: Food Antioxidants. Madavi, D.L., Deshpande, S.S., Salunkhe, D.K. (Eds.). Dekker, New York, 267.

Meléndez, P., Capriles, V. (2006). Antibacterial properties of tropical plants from Puerto Rico. Phytomedicine, 13(4), 272–276.

Molyneux, P. (2004). The use of the stable free radical diphenylpicrylhyrazyl (DPPH) for estimating antioxidant activity. Songklanakarin J. Sci. Technol., 26, 211–219.

Nabi, S., Ayub, E.F., Gholamreza, J.K., Hassan, G.N. (2014). Evaluation of the antibacterial activity of essential oil and aqueous and ethanolic extracts of Quercus infectoria leaves on food-borne pathogenic bacteria. Int. J. Pharma Sci. Res. (IJPSR), 5(10),709–713.

Renda, G., Tosun, G., Yaylı, N. (2016). SPME GC/MS analysis of three Ornithogalum L. species from Turkey. Rec. Nat. Prod., 10, 497–502.

Robak, J., Marcinkiewicz, E. (1995). Scavenging of reactive oxygen species as the mechanism of drug action. Pol. J. Pharmacol., 47, 89–98.

Saedi, D.E., Mahmoudvand, H., Sharififar, F., Fallahi, S., Monzote, L., Ezatkhah, F. (2015). Chemical composition along with anti-leishmanial and cytotoxic activity of Zataria multiflora. Pharm Biol., 8, 1–7.

Sandri, I.G., Zacaria, J., Fracaro, F., Delamare, A.P.L., Echeverrigaray, S. (2007) Antimicrobial activity of the essential oils of Brazilian species of the genus Cunila against foodborne pathogens and spoiling bacteria. Food Chem., 103(3), 823–828.

Shrestha, S., Kaushik, V.S., Eshwarappa, R.S.B., Subaramaihha, S.R., Ramanna, L.M., Lakkappa, D.B. (2014). Pharmacognostic studies of insect gall of Quercus infectoria Olivier (Fagaceae). Asian Pac. J. Trop. Biomed., 4(1), 35–39.

Sucilathangam, G., Gomatheswari, S.N., Velvizhi, G., Vincent, C.P., Palaniappan, N. (2012). Detection of antibacterial activity of medicinal plant Quercus infectoria against MRSA isolates in clinical samples. J. Pharm. Biomed. Sci., 14, 1–5.

Slinkard, K., Singleton, V.L. (1977). Total phenol analysis: automation and comparison with manual methods. Am. J. Enol. Viticult., 28, 49–55.

Solorzano‐Santos, F., Mmiranda‐Novales, M.G. (2012). Essential oils from aromatic herbs as antimicrobial agents. Curr. Opin. Biotechnol., 3, 136–41.

Tajkarimi, M.M., Ibrahima, S.A., Cliver, D.O. (2010). Antimicrobial herb and spice compounds in food. Food Ctrl., 21, 1199–1218.

Tambekar, D.H., Dahikar, S.B. (2011). Antibacterial activity of some Indian Ayurvedic preparations against enteric bacterial pathogens. J. Adv. Pharm. Technol. Res., 2(1), 24–29.

Theriault, M., Caillet, S., Kermash, S., Lacroix, M. (2006). Antioxidant: antiradical and at mutagenic activity of phenolic compounds present in maple products. Food Chem., 98, 490–501.

Torbati, M.A., Nazemiyeh, H., Lotfipour, F.S., Asnaashari, S., Nemati, M., Fathiazad, F. (2013). Composition and antibacterial activity of heracleum transcaucasicum and heracleum anisactis aerial parts essential oil. Adv. Pharm. Bull., 3(2), 415–418.

Young, I.S., Woodside, J.V. (2001). Antioxidants in health and disease. J. Clin. Path., 54(3), 176–186.

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Published
2021-12-09



Sule Ceylan 
Artvin Coruh University, Faculty of Forestry, Department of Forest Industry Engineering, 08000, Artvin, Turkey
Şehmuz Semih Yardımcı 
Artvin Coruh University, Faculty of Forestry, Department of Forest Industry Engineering, 08000, Artvin, Turkey
Yasemin Camadan 
Artvin Coruh University, Vocational School of Health Services, Pharmacy Services, 08000, Artvin, Turkey
Özlem Saral 
Recep Tayyip Erdogan University, College of Health, Department of Nutrition and Dietetics, 53100, Rize, Turkey
Özge Özsen Batur 
Eskisehir Osmangazi University, Department of Chemistry, 26480 Eskisehir, Turkey



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