Quantitative HPLC analysis and isolation of tiliroside from Alcea biennis Winterl and determination of total flavonoid content and biological activities

Sıla Özlem Sener; Tuğba Subaş; Şeyda Kanbolat; Merve Badem; Ufuk Özgen; Merve Tamer; Mahi Nur Kaplan; Esen Sezen Karaoğlan

doi:10.23902/trkjnat.1378819

Research Article

Quantitative HPLC analysis and isolation of tiliroside from Alcea biennis Winterl and determination of total flavonoid content and biological activities

Year 2024, Volume: 25 Issue: 1, 11 - 19, 15.04.2024

Sıla Özlem Sener Tuğba Subaş Şeyda Kanbolat Merve Badem Ufuk Özgen Merve Tamer Mahi Nur Kaplan Esen Sezen Karaoğlan

https://doi.org/10.23902/trkjnat.1378819

Abstract

Natural products are being investigated to obtain potential agents that could be used to prevent and ameliorate obesity and oxidative stress, which are two important factors that cause many metabolic disorders in the body. This study aimed to isolate and quantify the major compounds, to determine total flavonoid content, and to evaluate biological activities (antioxidant and pancreatic lipase (PL) inhibitory activity) of the methanol extract and the chloroform, ethyl acetate and the remaining aqueous subextracts of Alcea biennis Winterl. The major compound isolated from the ethyl acetate subextract was determined as tiliroside (kaempferol 3-O-β-(6″-O-trans-p-coumaroyl-glucopyranoside) using 1D-NMR and 2D-NMR spectral methods. The quantification of tiliroside in the extracts was specified by the newly validated high-performance liquid chromatography (HPLC) method. Ferric-reducing antioxidant power (FRAP) assay was performed to determine the antioxidant activity and the total flavonoid content was determined. The ethyl acetate subextract was found to have the highest tiliroside (75.4263 mg/g) and total flavonoid content (189 mg QE/g) and showed the highest FRAP value (259 ± 5.1316 µM TE/g). The methanol extract had a higher PL inhibitory activity (IC50 = 100.891 ± 5.160 µg/mL) compared to the other extracts. Tiliroside exhibited higher activity (IC50 = 86.203 ± 6.323 µg/mL) than the extracts. It has been demonstrated that A. biennis may be a promising plant for treatment of obesity, and further studies should be conducted to evaluate it as a therapeutic agent.

Keywords

Alcea, Chromatography, Obesity, Pancreatic lipase, Tiliroside

Ethical Statement

Since the article does not contain any studies with human or animal subject, its approval to the ethics committee was not required.

Supporting Institution

Turkish Scientific and Technical Research Council (TUBITAK)

Project Number

1919B011900478

References

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4. Aryal, S., Baniya, M.K., Danekhu, K., Kunwar, P., Gurung, R. & Koirala, N. 2019. Total phenolic content, flavonoid content and antioxidant potential of wild vegetables from Western Nepal. Plants, 8(4): 96. https://doi.org/10.3390/plants8040096
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6. Bagci, Y & Keskin, L. 2022. An ethnobotanical field survey in the Kadınhanı district of Konya in Turkey. KSU Journal of Agriculture and Nature, 25(2): 312-336. https://doi.org/10.18016/ksutarimdoga.vi.865880
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20. Goto, T., Teraminami, A., Lee, J.Y., Ohyama, K., Funakoshi, K., Kim, Y.I., Hirai, S., Uemura, T., Yu, R., Takahashi, N. & Kawada, T. 2012. Tiliroside, a glycosidic flavonoid, ameliorates obesity-induced metabolic disorders via activation of adiponectin signaling followed by enhancement of fatty acid oxidation in liver and skeletal muscle in obese-diabetic mice. The Journal of Nutritional Biochemistry, 23(7): 768-776. https://doi.org/10.1016/j.jnutbio.2011.04.001
21. Grochowski, D.M., Locatelli, M., Granica, S., Cacciagrano, F. & Tomczyk, M. 2018. A review on the dietary flavonoid tiliroside. Comprehensive Reviews in Food Science and Food Safety, 17(5): 1395-1421. https://doi.org/10.1111/1541-4337.12389
22. Hasim, H., Faridah, D.N., Qomaliyah, E.N. & Afandi, F.A. 2023. Pancreatic lipase inhibition activity in lipid absorption using traditional plants: A systematic review and meta-analysis. Indonesian Journal of Chemistry, 23(2): 568-582. https://doi.org/10.22146/ijc.76873
23. Irtem-Kartal, D., Eray, N. & Ozturk, F. 2020. Determination of total phenolic and flavonoid contents of some medicinal plants growing in Çaldıran province of Van. KSU Journal of Agricultural and Nature, 23(3): 611-616. https://doi.org/10.18016/ksutarimdoga.vi.637632
24. Kirca, A & Arslan, E. 2008. Antioxidant capacity and total phenolic content of selected plants from Turkey. International Journal of Food Science & Technology, 43: 2038-2046. https://doi.org/10.1111/j.1365-2621.2008.01818.x
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Year 2024, Volume: 25 Issue: 1, 11 - 19, 15.04.2024

Sıla Özlem Sener Tuğba Subaş Şeyda Kanbolat Merve Badem Ufuk Özgen Merve Tamer Mahi Nur Kaplan Esen Sezen Karaoğlan

https://doi.org/10.23902/trkjnat.1378819

Abstract

Vücutta birçok metabolik bozukluğa neden olan iki önemli faktör olan obezite ve oksidatif stresin önlenmesi ve iyileştirilmesi için doğal ürünler araştırılmaktadır. Bu çalışmada, Alcea biennis Winterl metanol ekstresi ile kloroform, etil asetat ve arta kalan sulu alt ekstrelerinin ana bileşiklerinin izole edilmesi ve miktarının belirlenmesi, toplam flavonoit içeriğinin tayini ve biyolojik aktivitelerinin (antioksidan ve pankreatik lipaz (PL) inhibitör aktivite) değerlendirmesi amaçlanmıştır. İzolasyon çalışmaları sonucunda etil asetat alt ekstresinden izole edilen ana bileşiğin 1D-NMR ve 2D-NMR spektral yöntemleri kullanılarak tilirozit (kemferol 3-O-β-(6″-O-trans-p-kumaroil-glukopiranozit) olduğu saptanmıştır. Ekstrelerdeki tilirozit miktarı yeni geliştirilen yüksek performanslı sıvı kromatografisi (HPLC) yöntemiyle belirlenmiştir. Antioksidan aktiviteyi belirlemek için ferrik-indirgeyici antioksidan güç (FRAP) analizi yapılmış ve ayrıca toplam flavonoit içeriği belirlenmiştir. Etil asetat alt ekstresinin en yüksek tilirozit (75,4263 mg/g) ve toplam flavonoit (189 mg QE/g) içeriğine sahip olduğu ve en yüksek FRAP değerini (259 ± 5,1316 µM TE/g) gösterdiği tespit edilmiştir. Metanol ekstresi diğer ekstrelerle karşılaştırıldığında daha yüksek PL inhibitör aktivitesine (IC50 = 100,891 ± 5,160 µg/mL) sahiptir. Tilirozit ise ekstrelerden daha yüksek aktivite (IC50 = 86,203 ± 6,323 µg/mL) sergilemiştir. Alcea biennis’in obezite tedavisi için umut verici bir bitki olabileceği ortaya konulmuştur ve terapötik ajan olarak değerlendirilmesi için daha ileri çalışmalar yapılmalıdır.

Project Number

1919B011900478

References

1. Abdel-Salam, N.A., Ghazy, N.M., Sallam, S.M., Radwan, M.M., Wanas, A.S., ElSohly, M.A., El-Demellawy, M.A., Abdel-Rahman, N.M., Piacente, S. & Shenouda, M.L. 2018. Flavonoids of Alcea rosea L. and their immune stimulant, antioxidant and cytotoxic activities on hepatocellular carcinoma HepG-2 cell line. Natural Product Research, 32(6): 702-706. https://doi.org/10.1080/14786419.2017.1332602
2. Akyol, Y. & Altan, Y. 2013. Ethnobotanical studies in the Maldan Village (Province Manisa, Turkey). Marmara Pharmaceutical Journal, 17: 21-25. https://doi.org/10.12991/201317388
3. Arvouet-Grand, A., Vennat, B., Pourrat, A. & Legret, P. 1994. Standardisation d'un extrait de propolis et identification des principaux constituants [Standardization of propolis extract and identification of principal constituents]. Journal de Pharmacie de Belgique, 49(6): 462-468.
4. Aryal, S., Baniya, M.K., Danekhu, K., Kunwar, P., Gurung, R. & Koirala, N. 2019. Total phenolic content, flavonoid content and antioxidant potential of wild vegetables from Western Nepal. Plants, 8(4): 96. https://doi.org/10.3390/plants8040096
5. Aydin, S., Ozturk, Y., Baser, K.H.C., Kirimer, N. & Kurtar-Ozturk, N. 1992. Effects of Alcea pallida L. (Ae) and Tilia argentea Desf. ex DC infusions on swimming performance in mice. Phytotherapy Research, 6: 219-220. https://doi.org/10.1002/ptr.2650060411
6. Bagci, Y & Keskin, L. 2022. An ethnobotanical field survey in the Kadınhanı district of Konya in Turkey. KSU Journal of Agriculture and Nature, 25(2): 312-336. https://doi.org/10.18016/ksutarimdoga.vi.865880
7. Benzie, I.F. & Strain, J.J. 1999. Ferric reducing/antioxidant power assay: direct measure of total antioxidant activity of biological fluids and modified version for simultaneous measurement of total antioxidant power and ascorbic acid concentration. Methods in Enzymology, 299: 15-27. https://doi.org/10.1016/s0076-6879(99)99005-5
8. Bhardwaj, M., Yadav, P., Vashishth, D., Sharma, K., Kumar, A., Chahal, J., Dalal, S. & Kataria, S.K. 2021. A review on obesity management through natural compounds and a green nanomedicine-based approach. Molecules, 26(11): 3278. https://doi.org/10.3390/molecules26113278
9. Buchholz, T. & Melzig, M.F. 2015. Polyphenolic compounds as pancreatic lipase inhibitors. Planta Medica, 81(10): 771-783. https://doi.org/10.1055/s-0035-1546173
10. Bulut, G. & Tuzlaci, E. 2013. An ethnobotanical study of medicinal plants in Turgutlu (Manisa-Turkey). Journal of Ethnopharmacology, 149(3): 633-647. https://doi.org/10.1016/j.jep.2013.07.016
11. Bustanji, Y., Al-Masri, I.M., Mohammad, M., Hudaib, M., Tawaha, K., Tarazi, H. & Alkhatib, H.S. 2011. Pancreatic lipase inhibition activity of trilactone terpenes of Ginkgo biloba. Journal of Enzyme Inhibition and Medicinal Chemistry, 26(4): 453-459. https://doi.org/10.3109/14756366.2010.525509
12. Chia, T.Y., Gan, C.Y., Shafie, M.H., Yap, P.G., Mohd Rodhi, A., Ahmad, A., Murugaiyah, V., Abdulla, M.H. & Johns, E.J. 2023. A comprehensive review on the pancreatic lipase inhibitory peptides: A future anti-obesity strategy. Electronic Journal of General Medicine, 20(3): em470. https://doi.org/10.29333/ejgm/12943
13. Cornelio, V.E., Maluf, F.V., Fernandes, J.B., Da Silva, M.F.G.F., Oliva, G., Guido, R.V.C. & Vieira, P.C. 2017. Isolation of tiliroside from Spiranthera odoratissima as inhibitor of Trypanosoma cruzi glyceraldehyde-3-phosphate dehydrogenase by using bioactivity-guided fractionation. Journal of the Brazilian Chemical Society, 28(3): 512-519. https://doi.org/10.21577/0103-5053.20160315
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15. Devi, S. & Kumar, V. 2020. Comprehensive structural analysis of cis- and trans-tiliroside and quercetrin from Malvastrum coromandelianum and their antioxidant activities. Arabian Journal of Chemistry, 13: 1720-1730. https://doi.org/10.1016/j.arabjc.2018.01.009
16. EMA (European Medicines Agency). 2022. ICH guideline Q2(R2) on validation of analytical procedures. https://www.ema.europa.eu/en/documents/scientific-guideline/ich-guideline-q2r2-validation-analytical-procedures-step-2b_en.pdf. (Data accessed: 18.01.2024).
17. Erarslan, Z.B., Colak, R. & Kultur, S. 2021. The preliminary ethnobotanical survey of medicinal plants in Develi (Kayseri/Turkey). Istanbul Journal of Pharmacy, 51(2): 263-270. https://doi.org/10.26650/istanbuljpharm.2021.817816
18. Ertas, A., Boga, M., Gazioglu, I., Yesil, Y., Hasimi, N., Ozaslan, C, Yilmaz, H. & Kaplan, M. 2016. Fatty acid, essential oil and phenolic compositions of Alcea pallida and Alcea apterocarpa with antioxidant, anticholinesterase and antimicrobial activities. Chiang Mai Journal of Science, 43(1): 89-99.
19. Fernandes de Oliveira, A.M., Sousa Pinheiro, L., Souto Pereira, C.K., Neves Matias, W., Albuquerque Gomes, R., Souza Chaves, O., Vanderlei de Souza, M.deF., Nóbrega de Almeida, R. & Simões de Assis, T. 2012. Total phenolic content and antioxidant activity of some Malvaceae family species. Antioxidant, 1(1): 33-43. https://doi.org/10.3390/antiox1010033
20. Goto, T., Teraminami, A., Lee, J.Y., Ohyama, K., Funakoshi, K., Kim, Y.I., Hirai, S., Uemura, T., Yu, R., Takahashi, N. & Kawada, T. 2012. Tiliroside, a glycosidic flavonoid, ameliorates obesity-induced metabolic disorders via activation of adiponectin signaling followed by enhancement of fatty acid oxidation in liver and skeletal muscle in obese-diabetic mice. The Journal of Nutritional Biochemistry, 23(7): 768-776. https://doi.org/10.1016/j.jnutbio.2011.04.001
21. Grochowski, D.M., Locatelli, M., Granica, S., Cacciagrano, F. & Tomczyk, M. 2018. A review on the dietary flavonoid tiliroside. Comprehensive Reviews in Food Science and Food Safety, 17(5): 1395-1421. https://doi.org/10.1111/1541-4337.12389
22. Hasim, H., Faridah, D.N., Qomaliyah, E.N. & Afandi, F.A. 2023. Pancreatic lipase inhibition activity in lipid absorption using traditional plants: A systematic review and meta-analysis. Indonesian Journal of Chemistry, 23(2): 568-582. https://doi.org/10.22146/ijc.76873
23. Irtem-Kartal, D., Eray, N. & Ozturk, F. 2020. Determination of total phenolic and flavonoid contents of some medicinal plants growing in Çaldıran province of Van. KSU Journal of Agricultural and Nature, 23(3): 611-616. https://doi.org/10.18016/ksutarimdoga.vi.637632
24. Kirca, A & Arslan, E. 2008. Antioxidant capacity and total phenolic content of selected plants from Turkey. International Journal of Food Science & Technology, 43: 2038-2046. https://doi.org/10.1111/j.1365-2621.2008.01818.x
25. Li, X., Tian, Y., Wang, T., Lin, Q., Feng, X., Jiang, Q., Liu, Y. & Chen, D. 2017. Role of the p-coumaroyl moiety in the antioxidant and cytoprotective effects of flavonoid glycosides: Comparison of astragalin and tiliroside. Molecules, 22(7): 1165. https://doi.org/10.3390/molecules22071165
26. Liu, T.T., Liu, X.T., Chen, Q.X. & Shi, Y. 2020. Lipase Inhibitors for Obesity: A Review. Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie, 128: 110314. https://doi.org/10.1016/j.biopha.2020.110314
27. Manna, P. & Jain, S.K. 2015. Obesity, oxidative stress, adipose tissue dysfunction, and the associated health risks: Causes and therapeutic strategies. Metabolic Syndrome and Related Disorders, 13(10): 423-444. https://doi.org/10.1089/met.2015.0095
28. Nagatomo, A., Nishida, N., Fukuhara, I., Noro, A., Kozai, Y., Sato, H. & Matsuura, Y. 2015. Daily intake of rosehip extract decreases abdominal visceral fat in preobese subjects: a randomized, double-blind, placebo-controlled clinical trial. Diabetes, Metabolic Syndrome and Obesity: Targets and Therapy, 8: 147-156. https://doi.org/10.2147/dmso.s78623
29. Nagatomo, A., Nishida, N., Matsuura, Y. & Shibata, N. 2013. Rosehip extract inhibits lipid accumulation in white adipose tissue by suppressing the expression of peroxisome proliferator-activated receptor gamma. Preventive Nutrition and Food Science, 18(2): 85-91. https://doi.org/10.3746/pnf.2013.18.2.085
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There are 42 citations in total.

Details

Primary Language	English
Subjects	Pharmacognosy
Journal Section	Research Article/Araştırma Makalesi
Authors	Sıla Özlem Sener 0000-0001-7679-7165 Tuğba Subaş 0000-0002-0956-6567 Şeyda Kanbolat 0000-0001-7261-7067 Merve Badem 0000-0002-1265-5616 Ufuk Özgen 0000-0001-9839-6717 Merve Tamer 0009-0006-7237-4804 Mahi Nur Kaplan This is me 0009-0000-1391-1530 Esen Sezen Karaoğlan 0000-0002-9098-9021
Project Number	1919B011900478
Early Pub Date	February 2, 2024
Publication Date	April 15, 2024
Submission Date	October 21, 2023
Acceptance Date	December 28, 2023
Published in Issue	Year 2024 Volume: 25 Issue: 1

Cite

APA	Sener, S. Ö., Subaş, T., Kanbolat, Ş., Badem, M., et al. (2024). Quantitative HPLC analysis and isolation of tiliroside from Alcea biennis Winterl and determination of total flavonoid content and biological activities. Trakya University Journal of Natural Sciences, 25(1), 11-19. https://doi.org/10.23902/trkjnat.1378819
AMA	Sener SÖ, Subaş T, Kanbolat Ş, Badem M, Özgen U, Tamer M, Kaplan MN, Sezen Karaoğlan E. Quantitative HPLC analysis and isolation of tiliroside from Alcea biennis Winterl and determination of total flavonoid content and biological activities. Trakya Univ J Nat Sci. April 2024;25(1):11-19. doi:10.23902/trkjnat.1378819
Chicago	Sener, Sıla Özlem, Tuğba Subaş, Şeyda Kanbolat, Merve Badem, Ufuk Özgen, Merve Tamer, Mahi Nur Kaplan, and Esen Sezen Karaoğlan. “Quantitative HPLC Analysis and Isolation of Tiliroside from Alcea Biennis Winterl and Determination of Total Flavonoid Content and Biological Activities”. Trakya University Journal of Natural Sciences 25, no. 1 (April 2024): 11-19. https://doi.org/10.23902/trkjnat.1378819.
EndNote	Sener SÖ, Subaş T, Kanbolat Ş, Badem M, Özgen U, Tamer M, Kaplan MN, Sezen Karaoğlan E (April 1, 2024) Quantitative HPLC analysis and isolation of tiliroside from Alcea biennis Winterl and determination of total flavonoid content and biological activities. Trakya University Journal of Natural Sciences 25 1 11–19.
IEEE	S. Ö. Sener, “Quantitative HPLC analysis and isolation of tiliroside from Alcea biennis Winterl and determination of total flavonoid content and biological activities”, Trakya Univ J Nat Sci, vol. 25, no. 1, pp. 11–19, 2024, doi: 10.23902/trkjnat.1378819.
ISNAD	Sener, Sıla Özlem et al. “Quantitative HPLC Analysis and Isolation of Tiliroside from Alcea Biennis Winterl and Determination of Total Flavonoid Content and Biological Activities”. Trakya University Journal of Natural Sciences 25/1 (April 2024), 11-19. https://doi.org/10.23902/trkjnat.1378819.
JAMA	Sener SÖ, Subaş T, Kanbolat Ş, Badem M, Özgen U, Tamer M, Kaplan MN, Sezen Karaoğlan E. Quantitative HPLC analysis and isolation of tiliroside from Alcea biennis Winterl and determination of total flavonoid content and biological activities. Trakya Univ J Nat Sci. 2024;25:11–19.
MLA	Sener, Sıla Özlem et al. “Quantitative HPLC Analysis and Isolation of Tiliroside from Alcea Biennis Winterl and Determination of Total Flavonoid Content and Biological Activities”. Trakya University Journal of Natural Sciences, vol. 25, no. 1, 2024, pp. 11-19, doi:10.23902/trkjnat.1378819.
Vancouver	Sener SÖ, Subaş T, Kanbolat Ş, Badem M, Özgen U, Tamer M, Kaplan MN, Sezen Karaoğlan E. Quantitative HPLC analysis and isolation of tiliroside from Alcea biennis Winterl and determination of total flavonoid content and biological activities. Trakya Univ J Nat Sci. 2024;25(1):11-9.

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