Determination of Phenolic Composition of Tilia Tomentosa Flowers Using UPLC-ESI-MS/MS

Abstract

Phenolic compounds, which are secondary metabolites of plants, are one of the main groups of compounds that provide antiallergic, antiinflammatory, antimicrobial, antioxidant, cardioprotective properties of medicinal and aromatic plants. These broad physiological effects that they possess lead researchers to examine the phenolic contents of plants. Tilia tomentosa Moench is one of 45 species belonging to Tiliaceae family, and the use of flowers in traditional treatment methods is quite common. Although it is well known that T. tomentosa flowers are rich in phenolics with various biological functions, there is no recent study on determination of phenolic compounds of T. tomentosa flowers using UPLC-ESI-MS/MS. In this study, firstly, T. tomentosa flowers were extracted using hexane and volatile oil fractions were separated from the plant. Distilled water:methanol (50:50) mixture was added to the remaining flower part at 40 °C and that subjected to extraction for 15 min. The obtained extract was filtered and dried in a lyophilizer at -70 °C. The residue was redissolved in a mixture of distilled water:methanol (80:20). The sample was analyzed by UPLC-MS/MS (Waters Acquity Ultra Performance LC, Xevo TQ-S MS/MS) by passing through Macherey-Nagel Chromafil Xtra PTFE-20/25 0.20 μm filters. According to the analysis results, 3,4-dihydroxybenzoic acid (66.820 mg/kg), myricetin (29.395 mg/kg), rutin (21.421 mg/kg), ferulic acid (12.334 mg/kg) and 3,4-dihydroxybenzaldehyde (10.383 mg/kg) were detected. T. tomentosa flowers have great potential to usage in industries such as food, medicine and cosmetic due to its rich content of phenolics.

Keywords

• Phenolics
• 3
• 4-dihydroxybenzoic acid
• Tilia tomentosa
• UPLC-ESI-MS/MS

Determination of Phenolic Composition of Tilia Tomentosa Flowers Using UPLC-ESI-MS/MS

Abstract

Phenolic compounds, which are secondary metabolites of plants, are one of the main groups of compounds that provide antiallergic, antiinflammatory, antimicrobial, antioxidant, cardioprotective properties of medicinal and aromatic plants. These broad physiological effects that they possess lead researchers to examine the phenolic contents of plants. Tilia tomentosa Moench is one of 45 species belonging to Tiliaceae family, and the use of flowers in traditional treatment methods is quite common. Although it is well known that T. tomentosa flowers are rich in phenolics with various biological functions, there is no recent study on determination of phenolic compounds of T. tomentosa flowers using UPLC-ESI-MS/MS. In this study, firstly, T. tomentosa flowers were extracted using hexane and volatile oil fractions were separated from the plant. Distilled water:methanol (50:50) mixture was added to the remaining flower part at 40 °C and that subjected to extraction for 15 min. The obtained extract was filtered and dried in a lyophilizer at -70 °C. The residue was redissolved in a mixture of distilled water:methanol (80:20). The sample was analyzed by UPLC-MS/MS (Waters Acquity Ultra Performance LC, Xevo TQ-S MS/MS) by passing through Macherey-Nagel Chromafil Xtra PTFE-20/25 0.20 μm filters. According to the analysis results, 3,4-dihydroxybenzoic acid (66.820 mg/kg), myricetin (29.395 mg/kg), rutin (21.421 mg/kg), ferulic acid (12.334 mg/kg) and 3,4-dihydroxybenzaldehyde (10.383 mg/kg) were detected. T. tomentosa flowers have great potential to usage in industries such as food, medicine and cosmetic due to its rich content of phenolics.

Keywords

• Phenolics
• 3
• 4-dihydroxybenzoic acid
• Tilia tomentosa
• UPLC-ESI-MS/MS

References

1. Othman, A., Ismail, A., Ghani, N. A., & Adenan, I. (2007). Antioxidant capacity and phenolic content of cocoa beans. Food Chemistry, 100(4), 1523-1530.
2. Tomás-Barberán, F. A., Ferreres, F., & Gil, M. I. (2000). Antioxidant phenolic metabolites from fruit and vegetables and changes during postharvest storage and processing. Studies in Natural Products Chemistry, 23, 739-795.
3. Lapornik, B., Prošek, M., & Wondra, A. G. (2005). Comparison of extracts prepared from plant by-products using different solvents and extraction time. Journal of Food Engineering, 71(2), 214-222.
4. Balasundram, N., Sundram, K., & Samman, S. (2006). Phenolic compounds in plants and agri-industrial by-products: Antioxidant activity, occurrence, and potential uses. Food Chemistry, 99(1), 191-203.
5. Llorent-Martínez, E. J., Spínola, V., Gouveia, S., & Castilho, P. C. (2015). HPLC-ESI-MS n characterization of phenolic compounds, terpenoid saponins, and other minor compounds in Bituminaria bituminosa. Industrial Crops and Products, 69, 80-90.
6. Ou, S., & Kwok, K. C. (2004). Ferulic acid: pharmaceutical functions, preparation and applications in foods. Journal of the science of food and agriculture, 84(11), 1261-1269.
7. Magnani, C., Isaac, V. L. B., Correa, M. A., & Salgado, H. R. N. (2014). Caffeic acid: a review of its potential use in medications and cosmetics. Analytical Methods, 6(10), 3203-3210.
8. Galati, G., & O'brien, P. J. (2004). Potential toxicity of flavonoids and other dietary phenolics: significance for their chemopreventive and anticancer properties. Free Radical Biology and Medicine, 37(3), 287-303.

9. Aydın, C., & Mammadov, R. (2017). Phenolic composition, antioxidant, antibacterial, larvacidal against Culex pipiens, and cytotoxic activites of Hyacinthella lineata s teudel extracts. International Journal of Food Properties, 20(10), 2276-2285.
10. Ignat, I., Volf, I., & Popa, V. I. (2011). A critical review of methods for characterisation of polyphenolic compounds in fruits and vegetables. Food Chemistry, 126(4), 1821-1835.
11. Pandey, K. B., & Rizvi, S. I. (2009). Plant polyphenols as dietary antioxidants in human health and disease. Oxidative Medicine and Cellular Longevity, 2(5), 270-278.
12. Dillard, C. J., & German, J. B. (2000). Phytochemicals: nutraceuticals and human health. Journal of the Science of Food and Agriculture, 80(12), 1744-1756.
13. Lubbe, A., & Verpoorte, R. (2011). Cultivation of medicinal and aromatic plants for specialty industrial materials. Industrial Crops and Products, 34(1), 785-801.
14. Aydin, C., Mammadov, R., Düşen, O., Özay, C., & Orhan, F. (2017). Total phenolics, antioxidant, antibacterial and cytotoxic activity studies of ethanolic extracts Arisarum vulgare O. Targ. Tozz. and Dracunculus vulgaris Schott. International Journal of Secondary Metabolite, 4(2), 114-122.
15. Kıvrak, Ş., Göktürk, T., & Kıvrak, İ. (2017). Assessment of volatile oil composition, phenolics and antioxidant activity of Bay (Laurus nobilis) leaf and usage in cosmetic applications. International Journal of Secondary Metabolite, 4(2), 148-161.
16. Farnsworth, N. R., Akerev, O., & Bingel, A.S. (1985). The Bullettion of WHO, 63, 9865-9871.
17. Fitsiou, L., Tzakou, O., Hancianu, M., & Poiata, A. (2007). Volatile constituents and antimicrobial activity of Tilia tomentosa Moench and Tilia cordata Miller oils. Journal of Essential Oil Research, 19(2), 183-185.
18. Başer, K. H. C., Tümen, G., Malyer, H., & Kırımer, N. (2005). Plants used for common cold in Turkey. In Proceedings of the IVth International Congress of Ethnobotany (ICEB 2005) (Vol. 133, p. 137).
19. Leri, F., Innocenti, M., Possieri, L., Gallori, S., & Mulinacci, N. (2015). Phenolic composition of “bud extracts” of Ribes nigrum L., Rosa canina L. and Tilia tomentosa M. Journal of Pharmaceutical and Biomedical Analysis, 115, 1-9.
20. Viola, H., Wolfman, C., De Stein, M. L., Wasowski, C., Pena, C., Medina, J. H., & Paladini, A. C. (1994). Isolation of pharmacologically active benzodiazepine receptor ligands from Tilia tomentosa (Tiliaceae). Journal of Ethnopharmacology, 44(1), 47-53.
21. Noguerón-Merino, M. C., Jiménez-Ferrer, E., Román-Ramos, R., Zamilpa, A., Tortoriello, J., & Herrera-Ruiz, M. (2015). Interactions of a standardized flavonoid fraction from Tilia americana with Serotoninergic drugs in elevated plus maze. Journal of Ethnopharmacology, 164, 319-327.
22. Sroka, Z., & Bełz, J. (2009). Antioxidant activity of hydrolyzed and non− hydrolyzed extracts of the inflorescence of linden (Tiliae inflorescentia). Advances in Clinical and Experimental Medicine, 18(4), 329-335.
23. Toker, G., Aslan, M., Yeşilada, E., Memişoğlu, M., & Ito, S. (2001). Comparative evaluation of the flavonoid content in officinal Tiliae flos and Turkish lime species for quality assessment. Journal of Pharmaceutical and Biomedical Analysis, 26(1), 111-121.
24. Pavlović, A. V., Papetti, A., Zagorac, D. Č. D., Gašić, U. M., Mišić, D. M., Tešić, Ž. L., & Natić, M. M. (2016). Phenolics composition of leaf extracts of raspberry and blackberry cultivars grown in Serbia. Industrial Crops and Products, 87, 304-314.
25. Kivrak, I., Kivrak, S., Harmandar, M., & Çetintas, Y. (2013). Phenolic compounds of Pinus brutia ten.: chemical investigation and quantitative analysis using an ultra-performance liquid chromatography tandem mass spectrometry with electrospray ionization source. Records of Natural Products, 7(4), 313-319.
26. Kıvrak, İ. (2015). Analytical methods applied to assess chemical composition, nutritional value and in vitro bioactivities of Terfezia olbiensis and Terfezia claveryi from Turkey. Food Analytical Methods, 8(5), 1279-1293.
27. Toker, G., Memişoğlu, M., Yeşilada, E., & Aslan, M. (2004). Main flavonoids of Tilia argentea DESF. ex DC. leaves. Turkish Journal of Chemistry, 28(6), 745-750.
28. Demiray, S., Pintado, M. E., & Castro, P. M. L. (2009). Evaluation of phenolic profiles and antioxidant activities of Turkish medicinal plants: Tilia argentea, Crataegi folium leaves and Polygonum bistorta roots. World Academy of Science, Engineering and Technology, 54, 312-317.