Login Register Cart 0
Generic placeholder image

The Natural Products Journal

Editor-in-Chief

ISSN (Print): 2210-3155
ISSN (Online): 2210-3163

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Phytochemical Investigation of Hypericum heterophyllum Flowers: LC-ESI-MS/MS Analysis, Total Phenolic and Flavonoid Contents, Antioxidant Activity

Author(s): Ramazan Erenler*, Cennet Yaman, lbrahim Demirtas and Mehmet Hakki Alma

Volume 13, Issue 7, 2023

Published on: 24 February, 2023

Article ID: e120123212672 Pages: 9

DOI: 10.2174/2210315513666230112165545

Price: $65

Abstract

Background: Hypericum heterophyllum has been used as a traditional medicine and includes significant bioactive compounds.

Objective: To quantitatively determine the phenolic and flavonoid contents of Hypericum heterophyllum flowers and evaluate the antioxidant activity. Also, to present the activity-compound relationship.

Methods: Flowers of H. heterophyllum Vent., endemic species for Turkey were collected from Yozgat-Turkey. H. heterophyllum flowers were extracted with methanol, ethanol, acetone, and chloroform individually. LC-ESI-MS/MS analysis for phytochemicals was carried out for each extract. Total phenolic and flavonoid content were carried out for each extract. The antioxidant activity was performed using DPPH•, ABTS•+, hydroxyl radical, and superoxide radical scavenging assays.

Results: Chlorogenic acid was found as a major compound in all extracts. Among the extracts, methanol extract included the most phenolic compound. The methanol extract and acetone extract consisted of the most flavonoids. Acetone and ethanol extracts revealed the most DPPH and ABTS activity respectively. Acetone extract exhibited the highest hydroxyl radical and superoxide radical scavenging effect.

Conclusion: Flowers of H. heterophyllum contain bioactive compounds and they revealed good antioxidant activity. Hence, H. heterophyllum flowers could be a promising agent for the pharmaceutical and food industries.

Graphical Abstract

[1]
Balunas, M.J.; Kinghorn, A.D. Drug discovery from medicinal plants. Life Sci., 2005, 78(5), 431-441.
[http://dx.doi.org/10.1016/j.lfs.2005.09.012] [PMID: 16198377]
[2]
Jachak, S.M.; Saklani, A. Challenges and opportunities in drug discovery from plants. Curr. Sci., 2007, 92(9), 1251-1257.
[3]
Harvey, A. Natural products in drug discovery. Drug Discov. Today, 2008, 13(19-20), 894-901.
[http://dx.doi.org/10.1016/j.drudis.2008.07.004] [PMID: 18691670]
[4]
Houghton, P.J. The role of plants in traditional medicine and current therapy. J. Altern. Complement. Med., 1995, 1(2), 131-143.
[http://dx.doi.org/10.1089/acm.1995.1.131] [PMID: 9395610]
[5]
Vitalini, S.; Tomè, F.; Fico, G. Traditional uses of medicinal plants in Valvestino (Italy). J. Ethnopharmacol., 2009, 121(1), 106-116.
[http://dx.doi.org/10.1016/j.jep.2008.10.005] [PMID: 18996175]
[6]
Newman, D.J.; Cragg, G.M. Natural products as sources of new drugs over the last 25 years. J. Nat. Prod., 2007, 70(3), 461-477.
[http://dx.doi.org/10.1021/np068054v] [PMID: 17309302]
[7]
Saidi, A.; Hambaba, L.; Kucuk, B.; Cacan, E.; Erenler, R. Phenolic profile, acute toxicity, and hepatoprotective and antiproliferative activities of Algerian Ruta tuberculata forssk. Curr. Bioact. Compd., 2022, 18(3), e191121198118.
[http://dx.doi.org/10.2174/1573407217666211119092552]
[8]
Brusotti, G.; Cesari, I.; Dentamaro, A.; Caccialanza, G.; Massolini, G. Isolation and characterization of bioactive compounds from plant resources: The role of analysis in the ethnopharmacological approach. J. Pharm. Biomed. Anal., 2014, 87, 218-228.
[http://dx.doi.org/10.1016/j.jpba.2013.03.007] [PMID: 23591140]
[9]
Boulechfar, S.; Zellagui, A.; Asan-Ozusaglam, M.; Bensouici, C.; Erenler, R.; Yildiz, İ.; Tacer, S.; Boural, H.; Demirtas, I. Chemical composition, antioxidant, and antimicrobial activities of two essential oils from Algerian propolis. Z. Naturforsch. C. J. Biosci., 2022, 77(3-4), 105-112.
[http://dx.doi.org/10.1515/znc-2021-0028] [PMID: 34392638]
[10]
Benguedouar, K.; Betina, S.B.; Erenler, R.; Genç, N.; Gok, M.; Sebti, M.; Madi, N.; Mekdade, L.; Gali, L.; Barkat, M. Evaluation of the antioxidant properties and total phenolic content of a dairy product (yogurt) supplemented with Thymus willdenowii essential oil from Algeria. J. Food Meas. Charact., 2022, 16(5), 3568-3577.
[http://dx.doi.org/10.1007/s11694-022-01455-6]
[11]
Aiyelaagbe, O. The need for bioactivity-safety evaluation and conservation of medicinal plants - A review. J. Med. Plants Res., 2009, 3(5), 324-328.
[12]
Dias, A.C.P.; Tomás-Barberán, F.A.; Fernandes-Ferreira, M.; Ferreres, F. Unusual flavonoids produced by callus of Hypericum perforatum. Phytochemistry, 1998, 48(7), 1165-1168.
[http://dx.doi.org/10.1016/S0031-9422(97)00963-1]
[13]
Davis, P.; Mill, R.; Tan, K. Flora of Turkey and The East Aegean Islands (Suppl. 1); Davis, P.; Mill, R.; Tan, K., Eds.; Edinburgh University Press: Edinburgh, UK, 1988, Vol. 10, pp. 150-151.
[14]
Decosterd, L.; Hoffmann, E.; Kyburz, R.; Bray, D.; Hostettmann, K. A new phloroglucinol derivative from Hypericum calycinum with antifungal and in vitro antimalarial activity. Planta Med., 1991, 57(6), 548-551.
[http://dx.doi.org/10.1055/s-2006-960203] [PMID: 1818346]
[15]
Jayasuriya, H.; McChesney, J.D.; Swanson, S.M.; Pezzuto, J.M. Antimicrobial and cytotoxic activity of rottlerin-type compounds from Hypericum drummondii. J. Nat. Prod., 1989, 52(2), 325-331.
[http://dx.doi.org/10.1021/np50062a018] [PMID: 2746258]
[16]
Tada, M.; Chiba, K.; Yamada, H.; Maruyama, H. Phloroglucinol derivatives as competitive inhibitors against thromboxane A2 and leukotriene D4 from Hypericum Erectum. Phytochemistry, 1991, 30(8), 2559-2562.
[http://dx.doi.org/10.1016/0031-9422(91)85100-E]
[17]
lshiguro, K.; Yamaki, M.; Kashihara, M.; Takagi, S.; Isoi, K. Sarothralin G: A new antimicrobial compound from Hypericum japonicum. Planta Med., 1990, 56(3), 274-276.
[http://dx.doi.org/10.1055/s-2006-960955]
[18]
Butterweck, V.; Böckers, T.; Korte, B.; Wittkowski, W.; Winterhoff, H. Long-term effects of St. John’s wort and hypericin on monoamine levels in rat hypothalamus and hippocampus. Brain Res., 2002, 930(1-2), 21-29.
[http://dx.doi.org/10.1016/S0006-8993(01)03394-7] [PMID: 11879791]
[19]
Yaman, C.; Onlu, S.; Ahmed, H.; Erenler, R. Comparison of phytochemicals and antioxidant capacity of Hypericum perforatum; wild plant parts and in vitro samples. J. Anim. Plant Sci., 2022, 32(2), 596-603.
[20]
Gülçin, İ. Antioxidant activity of food constituents: an overview. Arch. Toxicol., 2012, 86(3), 345-391.
[http://dx.doi.org/10.1007/s00204-011-0774-2] [PMID: 22102161]
[21]
Gülçın, İ.; Oktay, M.; Kıreçcı, E.; Küfrevıoǧlu, Ö.İ. Screening of antioxidant and antimicrobial activities of anise (Pimpinella anisum L.) seed extracts. Food Chem., 2003, 83(3), 371-382.
[http://dx.doi.org/10.1016/S0308-8146(03)00098-0]
[22]
Moon, J.K.; Shibamoto, T. Antioxidant assays for plant and food components. J. Agric. Food Chem., 2009, 57(5), 1655-1666.
[http://dx.doi.org/10.1021/jf803537k] [PMID: 19182948]
[23]
Gülçin, I.; Beydemir, Ş. Phenolic compounds as antioxidants: Carbonic anhydrase isoenzymes inhibitors. Mini Rev. Med. Chem., 2013, 13(3), 408-430.
[PMID: 23190033]
[24]
Krishnaiah, D.; Sarbatly, R.; Nithyanandam, R. A review of the antioxidant potential of medicinal plant species. Food Bioprod. Process., 2011, 89(3), 217-233.
[http://dx.doi.org/10.1016/j.fbp.2010.04.008]
[25]
Kähkönen, M.P.; Hopia, A.I.; Vuorela, H.J.; Rauha, J.P.; Pihlaja, K.; Kujala, T.S.; Heinonen, M. Antioxidant activity of plant extracts containing phenolic compounds. J. Agric. Food Chem., 1999, 47(10), 3954-3962.
[http://dx.doi.org/10.1021/jf990146l] [PMID: 10552749]
[26]
Gülçin, İ.; Elmastaş, M.; Aboul-Enein, H.Y. Determination of antioxidant and radical scavenging activity of Basil (Ocimum basilicum L. family Lamiaceae) assayed by different methodologies. Phytother. Res., 2007, 21(4), 354-361.
[http://dx.doi.org/10.1002/ptr.2069] [PMID: 17221941]
[27]
Yildiz, I.; Sen, O.; Erenler, R.; Demirtas, I.; Behcet, L. Bioactivity-guided isolation of flavonoids from Cynanchum acutum L. subsp. sibiricum (willd.) Rech. f. and investigation of their antiproliferative activity. Nat. Prod. Res., 2017, 31(22), 2629-2633.
[http://dx.doi.org/10.1080/14786419.2017.1289201] [PMID: 28278670]
[28]
Jimenez-Garcia, S.N.; Vazquez-Cruz, M.A.; Guevara-González, R.; Torres-Pacheco, I.; Cruz-Hernandez, A.; Feregrino-Perez, A.A. Current approaches for enhanced expression of secondary metabolites as bioactive compounds in plants for agronomic and human health purposes-A review. Pol. J. Food Nutr. Sci., 2013, 63(2), 67-78.
[http://dx.doi.org/10.2478/v10222-012-0072-6]
[29]
Atalar, M.N.; Aras, A.; Türkan, F.; Barlak, N.; Yildiko, Ü.; Karatas, O.F.; Alma, M.H. The effects of Daucus carota extract against PC3, PNT1a prostate cells, acetylcholinesterase, glutathione S‐transferase, and α‐glycosidase; an in vitro-in silico study. J. Food Biochem., 2021, 45(12), e13975.
[http://dx.doi.org/10.1111/jfbc.13975] [PMID: 34676566]
[30]
Singleton, V.L.; Slinkard, K. Total phenol analysis: Automation and comparison with manual methods. Am. J. Enol. Vitic., 1977, 28, 49-55.
[31]
Chang, C.C.; Yang, M.H.; Wen, H.M.; Chern, J.C. Estimation of total flavonoid content in propolis by two complementary colometric methods. J. Food Drug Anal., 2002, 10(3), 3.
[http://dx.doi.org/10.38212/2224-6614.2748]
[32]
Erenler, R.; Genç, N.; Elmastaş, M.; Emınağaoğlu, Ö. Evaluation of antioxidant capacity with total phenolic content of Galanthus krasnovii (Amaryllidaceae). Turkish J. Biodivers, 2019, 2(1), 13-17.
[http://dx.doi.org/10.38059/biodiversity.526833]
[33]
Genç, N.; Yildiz, İ.; Karan, T.; Emi̇nağaoğlu, Ö.; Erenler, R. Antioxidant activity and total phenolic contents of Galanthus woronowii (Amaryllidaceae). Turkish J. Biodivers, 2019, 2(1), 1-5.
[http://dx.doi.org/10.38059/biodiversity.515111]
[34]
Rafat Husain, S.; Cillard, J.; Cillard, P. Hydroxyl radical scavenging activity of flavonoids. Phytochemistry, 1987, 26(9), 2489-2491.
[http://dx.doi.org/10.1016/S0031-9422(00)83860-1]
[35]
Yasuhisa, T.; Hideki, H.; Muneyoshi, Y. Superoxide radical scavenging activity of phenolic compounds. Int. J. Biochem., 1993, 25(4), 491-494.
[http://dx.doi.org/10.1016/0020-711X(93)90655-X] [PMID: 8385635]
[36]
Kim, T.K. Understanding one-way ANOVA using conceptual figures. Korean J. Anesthesiol., 2017, 70(1), 22-26.
[http://dx.doi.org/10.4097/kjae.2017.70.1.22] [PMID: 28184262]
[37]
McGuinness, K.A. Of rowing boats, ocean liners and tests of the anova homogeneity of variance assumption. Austral Ecol., 2002, 27(6), 681-688.
[http://dx.doi.org/10.1046/j.1442-9993.2002.01233.x]
[38]
Smelcerovic, A.; Zuehlke, S.; Spiteller, M.; Raabe, N.; Özen, T. Phenolic constituents of 17 Hypericum species from Turkey. Biochem. Syst. Ecol., 2008, 36(4), 316-319.
[http://dx.doi.org/10.1016/j.bse.2007.09.002]
[39]
Yaman, C. Phytochemicals and antioxidant capacity of wild growing and in vitro Hypericum heterophyllum. Rom. Biotechnol. Lett., 2020, 25(6), 2111-2117.
[http://dx.doi.org/10.25083/rbl/25.6/2111.2117]
[40]
Dall’Agnol, R.; Ferraz, A.; Bernardi, A.P.; Albring, D.; Nör, C.; Sarmento, L.; Lamb, L.; Hass, M.; von Poser, G.; Schapoval, E.E.S. Antimicrobial activity of some Hypericum species. Phytomedicine, 2003, 10(6-7), 511-516.
[http://dx.doi.org/10.1078/094471103322331476] [PMID: 13678236]
[41]
Kladar, N.; Mrđanović, J.; Anačkov, G.; Šolajić, S.; Gavarić, N.; Srđenović, B.; Božin, B. Hypericum perforatum: Synthesis of active principles during flowering and fruitification - Novel aspects of biological potential. Evid. Based Complement. Alternat. Med., 2017, 2017, 1-11.
[http://dx.doi.org/10.1155/2017/2865610] [PMID: 29362586]
[42]
Karan, T.; Yildiz, I.; Aydin, A.; Erenler, R. Inhibition of various cancer cells proliferation of bornyl acetate and essential oil from Inula graveolens (Linnaeus) Desf. Rec. Nat. Prod., 2018, 12(3), 273-283.
[http://dx.doi.org/10.25135/rnp.30.17.09.057]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy