Antioxidant Activities and Enzyme Inhibition Potentials of Hypericum perforatum L. Ethanol Extracts

Abstract

This study aimed to investigate the antioxidant activities, enzyme inhibition potentials, total phenolic and flavonoid contents of Hypericum perforatum L. ethanol extracts. The phenolic content of the plant extract was determined using the Folin-Ciocalteu reagent. The antioxidant activities of the plant extract were determined based on the iron-reducing power and scavenging potentials of the DPPH radical. Furthermore, chelating ability, superoxide dismutase and in vitro anti-inflammatory activity, tyrosinase α-glucosidase, and cholinesterase inhibition assays were determined by spectrophotometric techniques. The plant extract's total phenolic and flavonoid contents were 8.828 mg GAE/g and 10.366 mg CTE/g extract, respectively. H. perforatum ethanolic extract exhibited scavenging of 1,1-Diphenyl-2-Picrylhydrazyl (DPPH) with an SC50 value of 0.469 mg/mL and superoxide anion radicals with IC50 values of 0.338 mg/mL. Ferric-ion chelating (%4.7 in 0.5 mg/mL), anti-inflammatory activity (%25.12 in 0.2 mg/mL), acetylcholinesterase inhibition (%18 in 0.2 mg/mL), butyrylcholinesterase inhibition (%15 in 0.2 mg/mL), tyrosinase inhibition (%35 in 0.5 mg/mL), and α-glucosidase inhibition (%35 in 0.2 mg/mL) activities of the plant extract were determined.

Keywords

• Antioxidant activity
• Ferric-ion chelating
• anti-inflammatory activity
• enzyme inhibition potentials

References

1. Altun ML., Sever Yılmaz B., Erdogan Orhan İ., Saltan Citoglu G. (2013). Assessment of cholinesterase and tyrosinase inhibitory and antioxidant effects of Hypericum perforatum L. (St. John's wort). Industrial Crops and Products, 43, 87-92.
2. Béjaoui A, Ben Salem I, Rokbeni N, M’rabet Y, Boussaid M, Boulila A. (2017). Bioactive compounds from Hypericum humifusum and Hypericum perfoliatum: inhibition potential of polyphenols with acetylcholinesterase and key enzymes linked to type-2 diabetes. Pharmaceutical Biology, 55(1), 906-911.
3. Buhian WPC, Rubio RO, Valle DL, Martin-Puzon JJ. (2016). Bioactive metabolite profiles and antimicrobial activity of ethanolic extracts from Muntingia calabura L. leaves and stems. Asian Pacific Journal of Tropical Biomedicine, 6 (8), 682-685.
4. Burunkaya B, Selli S, Kelebek H. (2021). Sarı Kantaron (Hypericum perforatum L.) fenoliklerinin karakterizasyonu, antioksidan ve antimikrobiyal potansiyelinin belirlenmesi. Çukurova Tarım ve Gıda Bilimleri Dergisi, 36(2), 309-324.
5. Cakir M, Duzova H, Baysal I, Gül CC, Kuşcu G, Kutluk F, Çakin H, Şeker Ş, İlbeği E, Uslu S, Avci U, Demir S, Akinci C, Atli S. (2017). The effect of Hypericum perforatum on kidney ischemia/reperfusion damage. Renal Failure, 39(1), 385-391.
6. Çol Ayvaz M, (2020) Phenolic compounds profile, neuroprotective effect and antioxidant potential of a commercial Turkish coffee. Revista de Nutriçao 33:e190097.
7. Çol Ayvaz M, Aksu F, Kır F, (2019) "Phenolic profile of three wild edible mushroom extracts from Ordu, Turkey and their antioxidant properties, enzyme inhibitory activities", British Food Journal, 121(6), 1248-1260.
8. Dinis TC, Madeira VM, Almeida LM. (1994). Action of phenolic derivatives (Acetaminophen, Salicylate, and 5-Aminosalicylate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers. Archieves of Biochemistry and Biophysics, 315(1), 161-169.

9. Ersoy E, Eroglu Ozkan E, Boga M, Mat A. (2020). Evaluation of in vitro biological activities of three Hypericum species (H. calycinum, H. confertum, and H. perforatum) from Turkey. South African Journal of Botany, 130, 141-147.
10. Fathi H, Ebrahimzadeh MA. (2013). Antioxidant and free radical scavenging activities of Hypericum perforatum L. (st. John’s wort). International Journal of Forest, Soil and Erosion (IJFSE), 3(2), 68-72.
11. Gill SS, Anjum NA, Gill R, Yadav S, Hasanuzzaman M, Fujita M, Mishra P, Sabat SC, Tuteja N. (2015). Superoxide dismutase-mentor of abiotic stress tolerance in crop plants. Environmental Science and Pollution Research, 22, 10375-10394.
12. Govindappa M, Channabasava R, Sowmya DV, Meenakshi J, Shreevidya MR, Lavanya A, Santoyo G, Sadananda TS. (2011). Phytochemical screening, antimicrobial and in vitro anti-inflammatory activity of endophytic extracts from Loranthus sp. Pharmacognosy Journal, 3(25), 82-90.
13. Guedes AP, Franklin G, Fernandes-Ferreira M. (2012). Hypericum sp.: essential oil composition and biological activities. Phytochemical Reviews 11, 127–152.
14. Gül V, Cetinkaya H, Seckin Dinler B, Sefaoglu F. (2023). Comparative Analysis Of Biochemical Content, Antimicrobial And Antioxidant Activities Of Hypericum Perforatum L. Species Is Grown In Türkiye. Pakistan Journal of Botany, 55(4), 1277-1285.
15. Iwai K, Kishimoto N, Kakino Y, Mochida K, FujitaT. (2004). In vitro antioxidative effects and tyrosinase inhibitory activities of seven hydroxycinnamoyl derivatives in green coffee beans. Journal of Agricultural and Food Chemistry, 52(15), 4893-4898.
16. Juvekar AR, Sakat S, Wankhede S, Juvekar M, Gambhire MN. (2009). In vitro antioxidant and anti-inflammatory activity of methanol extract of Oxalis corniculata Linn. Planta Medica. 75, 09.
17. Kasangana, PB, Haddad PS, Stevanovic T. (2015). Study of polyphenol content and antioxidant capa city of Myrianthus arboreus (Cecropiaceae) root bark extracts. Antioxidants, 4(2), 410-426.
18. Kelebekli L, Yılmaz FZ, Çol Ayvaz M, Şahin E. (2022). Synthesis and biological effects evaluation of benzoconduritols C and D from oxabenzonorbornadiene. Journal of Iranian Chemical Society, 19(5), 1899-1912.
19. Kim DO, Jeong SW, Lee CY. (2003). Antioxidant capacity of phenolic phytochemicals from various cultivars of plums. Food Chemistry, 81(3), 321-326.
20. Kolören O, Kolören Z, Atli Şekeroğlu Z., Çolayvaz M, Karanis P. (2019). Amoebicidal and Amoebistatic Effects of Artemisia argyi Methanolic Extracts on Acanthamoeba castellanii Trophozoites and Cysts. Acta Parasitologica, 64(1),63–70.
21. Kumar V, Singh PN, Bhattacharya SK. (2001). Anti-inflammatory and analgesic activity of Indian Hypericum perforatum L. Indian Journal of Experimental Biology, 39(4), 339-343.
22. Makarova K, Sajkowska-Kozielewicz JJ, Zawada K, Olchowik-Grabarek E, Ciach MA, Gogolewski K, Dobros N, Ciechowicz P, Freichels H, Gambin A. (2021). Harvest time affects antioxidant capacity, total polyphenol and flavonoid content of Polish St John’s wort’s (Hypericum perforatum L.) flowers. Scientific Reports, 11, 3989.
23. Mettupalayam Kaliyannan Sundaramoorthy P, Kilavan Packiam K. (2020). In vitro enzyme inhibitory and cytotoxic studies with Evolvulus alsinoides (Linn.) Linn. Leaf extract: a plant from Ayurveda recognized as Dasapushpam for the management of Alzheimer’s disease and diabetes mellitus. BMC Complementary Medicine and Therapies, 20, 129.
24. Mohanasundari M, Srinivasan MS, Sethupathy, S, Sabesan M. (2006). Enhanced neuroprotective effect by combination of bromocriptine and Hypericum perforatum extract against MPTP-induced neurotoxicity in mice. Journal of Neurological Sciences, 249(2), 140-144.
25. Oguntibeju OO, Esterhuyse AJ, Truter EJ. (2010). Possible role of red palm oil supplementation in reducing oxidative stress in HIV/AIDS and TB patients: A review. Journal of Medicinl Plant Research, 4(3), 188-196.
26. Pistia-Brueggeman, G, Hollingsworth RI. (2001). A preparation and screening strategy for glycosidase inhibitors. Tetrahedron, 57(42), 8773-8778.
27. Radulović N, Stankov-Jovanović V, Stojanović Gordana, Šmelcerović A, Spiteller M, Asakawa Y. (2007). Screening of in vitro antimicrobial and antioxidant activity of nine Hypericum species from the Balkans, Food Chemistry, 103(1),15-21.
28. Safari R, Raftani Amiri Z, Esmaeilzadeh Kenari R. (2020). Antioxidant and antibacterial activities of C-phycocyanin from common name Spirulina platensis. Iranian Journal of Fisheries Sciences, 19(4), 1911-1927.
29. Sanchez-Moreno C, Larrauri JA, Saura-Calixto F. (1998). A procedure to measure the antiradical efficiency of polyphenols. Journal of the Science of Food and Agriculture, 76(2), 270-276.
30. Sarikurkcu C, Locatelli M, Tartaglia A, Ferrone V, Juszczak AM, Ozer MS, Tepe B, Tomczyk M. (2020). Enzyme and biological activities of the water extracts from the plants Aesculus hippocastanum, Olea europaea and Hypericum perforatum that are used as Folk Remedies in Turkey. Molecules. 25(5), 1202.
31. Shah M, Parveen Z, Khan MR. (2017). Evaluation of antioxidant, anti-inflammatory, analgesic and antipyretic activities of the stem bark of Sapindus mukorossi. BMC Complementary and Alternative Medicine, 17(1), 526.
32. Singleton V, Rossi J. (1965). Colorimetry of Total Phenolic Compounds with Phosphomolybdic-Phosphotungstic Acid Reagents. American Journal of Enology and Viticulture, 16, 144-158.
33. Süntar I, Küpeli Akkol E, Yılmazer D, Baykal T, Kırmızıbekmez H, Alper M, Yeşilada E. (2010). Investigations on the in vivo wound healing potential of Hypericum perforatum L. Journal of Ethnopharmacology, 127(2), 468-477.
34. Tusevski O, Krstikj M, Stanoeva JP, Stefova M, Gadzovska Simic S. (2018). Phenolic profile and biological activity of Hypericum perforatum L.: Can roots be considered as a new source of natural compounds? South African Journal of Botany, 117, 301-310.
35. Williams LA, O'Connar A, Latore L, Dennis O, Ringer S, Whittaker JA, Conrad J, Vogler B, Rosner H, Kraus W. (2008). The in vitro anti-denaturation effects induced by natural products and non-steroidal compounds in heat-treated (immunogenic) bovine serum albumin is proposed as a screening assay for the detection of anti-inflammatory compounds, without the use of animals, in the early stages of the drug discovery process. The West Indian Medical Journal, 57(4), 327-331.
36. Zhang L, Zhang H, Tang L, Hu X, Xu M. (2022). Isolation, characterization, antioxidant activity, metal-chelating activity, and protein-precipitating capacity of condensed tannins from Plum (Prunus salicina) fruit. Antioxidants. 11(4), 714.