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Mini-Reviews in Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1389-5575
ISSN (Online): 1875-5607

Review Article

Hypericum spp.: An Update on the Biological Activities and Metabolic Profiles

Author(s): Mariangela Marrelli, Giancarlo Statti and Filomena Conforti*

Volume 20, Issue 1, 2020

Page: [66 - 87] Pages: 22

DOI: 10.2174/1389557519666190926120211

Price: $65

Abstract

Plants from the genus Hypericum, one genus of the Hypericaceae family, have attracted a lot of attention for their potential pharmaceutical applications. Most of the studies in the literature focus on H. perforatum L. (common St. John's wort), whose complex spectrum of bioactive compounds makes this species one of the top herbal remedies and supplements in the world. It is also important to compare the studies on other Hypericum species, both from the phytochemical and biological point of view. The aim of this review was to provide an update of most recent studies about biological investigations of plants belonging to Hypericum genus. The metabolic profiles of Hypericum spp. were also discussed in order to present a spectrum of secondary metabolites not previously identified in this genus.

Keywords: Antinociceptive activity, Hypericum spp., metabolic profiles, neurodegenerative disorder, toxicity, genus.

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[1]
Dauncey, E.A.; Irving, J.T.W.; Allkin, R. A review of issues of nomenclature and taxonomy of Hypericum perforatum L. and Kew’s medicinal plant names services. J. Pharm. Pharmacol., 2019, 71(1), 4-14.
[http://dx.doi.org/10.1111/jphp.12831] [PMID: 29034955]
[2]
Franklin, G.; Beerhues, L.; Čellárová, E. Molecular and biotechnological advancements in Hypericum species. Front. Plant Sci., 2016, 7, 1687.
[http://dx.doi.org/10.3389/fpls.2016.01687] [PMID: 27891141]
[3]
Zirak, N.; Shafiee, M.; Soltani, G.; Mirzaei, M.; Sahebkar, A. Hypericum perforatum in the treatment of psychiatric and neurodegenerative disorders: Current evidence and potential mechanisms of action. J. Cell. Physiol., 2019, 234(6), 8496-8508.
[http://dx.doi.org/10.1002/jcp.27781] [PMID: 30461013]
[4]
Belwal, T.; Devkota, H.P.; Singh, M.K.; Sharma, R.; Upadhayay, S.; Joshi, C.; Bisht, K.; Gour, J.K.; Bhatt, I.D.; Rawal, R.S.; Pande, V. (2019) St. John’s Wort (Hypericum perforatum) in:. Nonvitamin and Nonmineral Nutritional Supplements;, Seyed Mohammad Nabavi; Ana Sanches Silva, Ed. Academic Press 2019, p. 415-432
[5]
Barnes, J.; Anderson, L.A.; Phillipson, J.D. St John’s wort (Hypericum perforatum L.): A review of its chemistry, pharmacology and clinical properties. J. Pharm. Pharmacol., 2001, 53(5), 583-600.
[http://dx.doi.org/10.1211/0022357011775910] [PMID: 11370698]
[6]
Whiskey, E.; Werneke, U.; Taylor, D. A systematic review and meta-analysis of Hypericum perforatum in depression: A comprehensive clinical review. Int. Clin. Psychopharmacol., 2001, 16(5), 239-252.
[http://dx.doi.org/10.1097/00004850-200109000-00001] [PMID: 11552767]
[7]
Assiri, K.; Alyami, Y.; Uyanik, J.M.; Romero-Reyes, M. Hypericum perforatum (St. John’s Wort) as a possible therapeutic alternative for the management of Trigeminal Neuralgia (TN) - A case report. Complement. Ther. Med., 2017, 30, 36-39.
[http://dx.doi.org/10.1016/j.ctim.2016.10.014] [PMID: 28137525]
[8]
Galeotti, N. Hypericum perforatum (St John’s wort) beyond depression: A therapeutic perspective for pain conditions. J. Ethnopharmacol., 2017, 200, 136-146.
[http://dx.doi.org/10.1016/j.jep.2017.02.016] [PMID: 28216196]
[9]
Conforti, F.; Statti, G.A.; Tundis, R.; Menichini, F.; Houghton, P. Antioxidant activity of methanolic extract of Hypericum triquetrifolium Turra aerial part. Fitoterapia, 2002, 73(6), 479-483.
[http://dx.doi.org/10.1016/S0367-326X(02)00162-4] [PMID: 12385870]
[10]
Cakir, A.; Mavi, A.; Yildirim, A.; Duru, M.E.; Harmandar, M.; Kazaz, C. Isolation and characterization of antioxidant phenolic compounds from the aerial parts of Hypericum hyssopifolium L. by activity-guided fractionation. J. Ethnopharmacol., 2003, 87(1), 73-83.
[http://dx.doi.org/10.1016/S0378-8741(03)00112-0] [PMID: 12787957]
[11]
Dall’Agnol, R.; Ferraz, A.; Bernardi, A.P.; Albring, D.; Nör, C.; Sarmento, L.; Lamb, L.; Hass, M.; von Poser, G.; Schapoval, E.E. Antimicrobial activity of some Hypericum species. Phytomedicine, 2003, 10(6-7), 511-516.
[http://dx.doi.org/10.1078/094471103322331476] [PMID: 13678236]
[12]
Barros, F.M.; Pippi, B.; Dresch, R.R.; Dauber, B.; Luciano, S.C.; Apel, M.A.; Fuentefria, A.M.; von Poser, G.L. Antifungal and antichemotactic activities and quantification of phenolic compounds in lipophilic extracts of Hypericum spp. native to South Brazil. Ind. Crops Prod., 2013, 44, 294-299.
[http://dx.doi.org/10.1016/j.indcrop.2012.11.017]
[13]
Statti, G.A.; Conforti, F.; Menichini, F.; Marrelli, M.; Gangale, C.; Tundis, R.; Loizzo, M.R.; Bonesi, M.; Menichini, F. Protective effect of Hypericum calabricum Sprengel on oxidative damage and its inhibition of nitric oxide in lipopolysaccharide-stimulated RAW 264.7 macrophages. Biol. Res., 2011, 44(3), 213-218.
[http://dx.doi.org/10.4067/S0716-97602011000300001] [PMID: 22688907]
[14]
Vijayan, P.; Vinod Kumar, S.; Dhanaraj, S.A.; Mukherjee, P.K.; Suresh, B. In vitro cytotoxicity and antitumour properties of Hypericum mysorense and Hypericum patulum. Phytother. Res., 2003, 17(8), 952-956.
[http://dx.doi.org/10.1002/ptr.1271] [PMID: 13680832]
[15]
Rabanal, R.M.; Bonkanka, C.X.; Hernández-Pérez, M.; Sánchez-Mateo, C.C. Analgesic and topical anti-inflammatory activity of Hypericum canariense L. and Hypericum glandulosum Ait. J. Ethnopharmacol., 2005, 96(3), 591-596.
[http://dx.doi.org/10.1016/j.jep.2004.10.013] [PMID: 15619583]
[16]
Viana, A.F.; Heckler, A.P.; Fenner, R.; Rates, S.M.K. Antinociceptive activity of Hypericum caprifoliatum and Hypericum polyanthemum (Guttiferae). Braz. J. Med. Biol. Res., 2003, 36(5), 631-634.
[http://dx.doi.org/10.1590/S0100-879X2003000500011] [PMID: 12715083]
[17]
Avato, P. A survey on the Hypericum genus: Secondary metabolites and bioactivity In: Studies in Natural Products Chemistry; Atta- ur-Rahman, Ed. Elsevier 2005; 30, p. 603-633.
[18]
Marrelli, M.; Conforti, F.; Toniolo, C.; Nicoletti, M.; Statti, G.; Menichini, F. Hypericum perforatum: Influences of the habitat on chemical composition, photo-induced cytotoxicity, and antiradical activity. Pharm. Biol., 2014, 52(7), 909-918.
[http://dx.doi.org/10.3109/13880209.2013.872675] [PMID: 24920234]
[19]
Marrelli, M.; Statti, G.; Conforti, F.; Menichini, F. New potential pharmaceutical applications of Hypericum species. Mini Rev. Med. Chem., 2016, 16(9), 710-720.
[http://dx.doi.org/10.2174/1389557515666150709105844] [PMID: 26156546]
[20]
Bridi, H.; Meirelles, G.C.; von Poser, G.L. Structural diversity and biological activities of phloroglucinol derivatives from Hypericum species. Phytochemistry, 2018, 155, 203-232.
[http://dx.doi.org/10.1016/j.phytochem.2018.08.002] [PMID: 30153613]
[21]
Guo, Y.; Zhang, N.; Chen, C.; Huang, J.; Li, X.N.; Liu, J.; Zhu, H.; Tong, Q.; Zhang, J.; Luo, Z.; Xue, Y.; Zhang, Y. Tricyclic polyprenylated acylphloroglucinols from St John’s Wort, Hypericum perforatum. J. Nat. Prod., 2017, 80(5), 1493-1504.
[http://dx.doi.org/10.1021/acs.jnatprod.6b01178] [PMID: 28445039]
[22]
Radulović, N.S.; Genčić, M.S.; Stojanović, N.M.; Randjelović, P.J.; Baldovini, N.; Kurteva, V. Prenylated β-diketones, two new additions to the family of biologically active Hypericum perforatum L. (Hypericaceae) secondary metabolites. Food Chem. Toxicol., 2018, 118, 505-513.
[http://dx.doi.org/10.1016/j.fct.2018.05.009] [PMID: 29751080]
[23]
Bréard, D.; Viault, G.; Mezier, M.C.; Pagie, S.; Bruguière, A.; Richomme, P.; Charreau, B.; Derbré, S. Additional insights into Hypericum perforatum content: isolation, total synthesis, and absolute configuration of hyperbiphenyls A and B from immunomodulatory root extracts. J. Nat. Prod., 2018, 81(8), 1850-1859.
[http://dx.doi.org/10.1021/acs.jnatprod.8b00325] [PMID: 30024167]
[24]
Gao, W.; Hou, W.Z.; Zhao, J.; Xu, F.; Li, L.; Xu, F.; Sun, H.; Xing, J.G.; Peng, Y.; Wang, X.L.; Ji, T.F.; Gu, Z.Y. Polycyclic polyprenylated acylphloroglucinol congeners from Hypericum scabrum. J. Nat. Prod., 2016, 79(6), 1538-1547.
[http://dx.doi.org/10.1021/acs.jnatprod.5b01063] [PMID: 27280968]
[25]
Gao, W.; Hu, J.W.; Xu, F.; Wei, C.J.; Shi, M.J.; Zhao, J.; Wang, J.J.; Zhen, B.; Ji, T.F.; Xing, J.G.; Gu, Z.Y.; Xu, F. Polyisoprenylated benzoylphloroglucinol derivatives from Hypericum scabrum. Fitoterapia, 2016, 115, 128-134.
[http://dx.doi.org/10.1016/j.fitote.2016.10.003] [PMID: 27751884]
[26]
Hu, J.; Gao, W.; Xu, F.; Wei, C.; Shi, M.; Sun, H.; Zhen, B.; Wang, J.; Ji, T.; Jiang, J. Polycyclic polyprenylated acylphloroglucinol derivatives from Hypericum scabrum. Bioorg. Med. Chem. Lett., 2017, 27(21), 4932-4936.
[http://dx.doi.org/10.1016/j.bmcl.2017.09.001] [PMID: 28958618]
[27]
Liu, R.; Su, Y.; Yang, J.; Wang, A. Polyprenylated acylphloroglucinols from Hypericum scabrum. Phytochemistry, 2017, 142, 38-50.
[http://dx.doi.org/10.1016/j.phytochem.2017.06.011] [PMID: 28675829]
[28]
Hu, L.; Wang, Z.; Zhang, J.; Lu, Y.; Wang, K.; Xue, Y.; Zhang, Y.; Zhang, Y. Two new bioactive α-pyrones from Hypericum japonicum. Molecules, 2016, 21(4), 515.
[http://dx.doi.org/10.3390/molecules21040515] [PMID: 27104499]
[29]
Hu, L.; Zhang, Y.; Zhu, H.; Liu, J.; Li, H.; Li, X.N.; Sun, W.; Zeng, J.; Xue, Y.; Zhang, Y. Filicinic acid based meroterpenoids with anti-epstein-barr virus activities from Hypericum japonicum. Org. Lett., 2016, 18(9), 2272-2275.
[http://dx.doi.org/10.1021/acs.orglett.6b00906] [PMID: 27116597]
[30]
Wu, R.; Le, Z.; Wang, Z.; Tian, S.; Xue, Y.; Chen, Y.; Hu, L.; Zhang, Y. Hyperjaponol H, a new bioactive filicinic acid-based meroterpenoid from Hypericum japonicum Thunb. ex Murray. Molecules, 2018, 23(3), 683.
[http://dx.doi.org/10.3390/molecules23030683] [PMID: 29562631]
[31]
Li, Y.P.; Hu, K.; Yang, X.W.; Xu, G. Antibacterial dimeric acylphloroglucinols from Hypericum japonicum. J. Nat. Prod., 2018, 81(4), 1098-1102.
[http://dx.doi.org/10.1021/acs.jnatprod.8b00017] [PMID: 29667821]
[32]
Zhou, Z.B.; Li, Z.R.; Wang, X.B.; Luo, J.G.; Kong, L.Y. Polycyclic polyprenylated derivatives from Hypericum uralum: Neuroprotective effects and antidepressant-like activity of uralodin A. J. Nat. Prod., 2016, 79(5), 1231-1240.
[http://dx.doi.org/10.1021/acs.jnatprod.5b00667] [PMID: 27148858]
[33]
Li, X.; Li, Y.; Luo, J.; Zhou, Z.; Xue, G.; Kong, L. New phloroglucinol derivatives from the whole plant of Hypericum uralum. Fitoterapia, 2017, 123, 59-64.
[http://dx.doi.org/10.1016/j.fitote.2017.09.020] [PMID: 28962944]
[34]
Niwa, K.; Tanaka, N.; Kim, S.Y.; Kojoma, M.; Kashiwada, Y. Hyperdioxane A, a conjugate of dibenzo-1, 4-dioxane and sesquiterpene from Hypericum ascyron. Org. Lett., 2018, 20(18), 5977-5980.
[http://dx.doi.org/10.1021/acs.orglett.8b02739] [PMID: 30207481]
[35]
Nedialkov, P.T.; Ilieva, Y.; Momekov, G.; Kokanova-Nedialkova, Z. Cytotoxic prenylated acylphloroglucinols from Hypericum annulatum. Fitoterapia, 2018, 127, 375-382.
[http://dx.doi.org/10.1016/j.fitote.2018.03.011] [PMID: 29627475]
[36]
Li, D.; Du, G.; Gong, X.; Guo, J.; Zhang, J.; Chen, C.; Xue, Y.; Zhu, H.; Zhang, Y. Hyperattenins L and M, two new polyprenylated acylphloroglucinols with adamantyl and homoadamantyl core structures from Hypericum attenuatum. Fitoterapia, 2018, 125, 130-134.
[http://dx.doi.org/10.1016/j.fitote.2017.12.020] [PMID: 29288028]
[37]
Bridi, H.; Meirelles, G.C.; Bordignon, S.A.L.; Rates, S.M.K.; von Poser, G.L. Denudatin A, a dimeric acylphloroglucinol from Hypericum denudatum presents an antinociceptive effect in mice. Planta Med., 2017, 83(17), 1329-1334.
[http://dx.doi.org/10.1055/s-0043-109567] [PMID: 28472841]
[38]
Lu, S.; Tanaka, N.; Tatano, Y.; Kashiwada, Y. Erecricins A-E, prenylated acylphloroglucinols from the roots of Hypericum erectum. Fitoterapia, 2016, 114, 188-193.
[http://dx.doi.org/10.1016/j.fitote.2016.08.014] [PMID: 27575327]
[39]
Mathioudaki, A.; Berzesta, A.; Kypriotakis, Z.; Skaltsa, H.; Heilmann, J. Phenolic metabolites from Hypericum kelleri Bald., an endemic species of Crete (Greece). Phytochemistry, 2018, 146, 1-7.
[http://dx.doi.org/10.1016/j.phytochem.2017.11.009] [PMID: 29190454]
[40]
Fobofou, S.A.; Franke, K.; Porzel, A.; Brandt, W.; Wessjohann, L.A. Tricyclic acylphloroglucinols from Hypericum lanceolatum and regioselective synthesis of selancins A and B. J. Nat. Prod., 2016, 79(4), 743-753.
[http://dx.doi.org/10.1021/acs.jnatprod.5b00673] [PMID: 26950610]
[41]
Crockett, S.; Baur, R.; Kunert, O.; Belaj, F.; Sigel, E. A new chromanone derivative isolated from Hypericum lissophloeus (Hypericaceae) potentiates GABAA receptor currents in a subunit specific fashion. Bioorg. Med. Chem., 2016, 24(4), 681-685.
[http://dx.doi.org/10.1016/j.bmc.2015.12.037] [PMID: 26791864]
[42]
Cao, X.; Yang, X.; Wang, P.; Liang, Y.; Liu, F.; Tuerhong, M.; Jin, D.Q.; Xu, J.; Lee, D.; Ohizumi, Y.; Guo, Y. Polycyclic phloroglucinols as PTP1B inhibitors from Hypericum longistylum: Structures, PTP1B inhibitory activities, and interactions with PTP1B. Bioorg. Chem., 2017, 75, 139-148.
[http://dx.doi.org/10.1016/j.bioorg.2017.09.001] [PMID: 28946049]
[43]
Xu, W.J.; Li, R.J.; Quasie, O.; Yang, M.H.; Kong, L.Y.; Luo, J. Polyprenylated tetraoxygenated xanthones from the roots of Hypericum monogynum and their neuroprotective activities. J. Nat. Prod., 2016, 79(8), 1971-1981.
[http://dx.doi.org/10.1021/acs.jnatprod.6b00251] [PMID: 27525351]
[44]
Zeng, Y.R.; Yi, P.; Gu, W.; Xiao, C.X.; Huang, L.J.; Tian, D.S.; Yan, H.; Chen, D.Z.; Yuan, C.M.; Hao, X.J. Hypermonins A and B, two 6-norpolyprenylated acylphloroglucinols with unprecedented skeletons from Hypericum monogynum. Org. Biomol. Chem., 2018, 16(22), 4195-4198.
[http://dx.doi.org/10.1039/C8OB00650D] [PMID: 29796533]
[45]
Tanaka, N.; Yano, Y.; Tatano, Y.; Kashiwada, Y. Hypatulins A and B, meroterpenes from Hypericum patulum. Org. Lett., 2016, 18, 5360-5363.
[46]
Tian, W.J.; Qiu, Y.Q.; Chen, H.F.; Jin, X.J.; Yao, X.J.; Dai, Y.; Yao, X.S. Chiral separation and absolute configurations of two pairs of racemic polyprenylated benzophenones from Hypericum sampsonii. Fitoterapia, 2017, 116, 39-44.
[http://dx.doi.org/10.1016/j.fitote.2016.10.014] [PMID: 27818319]
[47]
Tanaka, N.; Tsuji, E.; Kashiwada, Y.; Kobayashi, J. Yezo’otogirins D–H, acylphloroglucinols and meroterpenes from Hypericum yezoense. Chem. Pharm. Bull. (Tokyo), 2016, 64(7), 991-995.
[http://dx.doi.org/10.1248/cpb.c16-00243] [PMID: 27373661]
[48]
Crockett, S.L.; Kunert, O.; Pferschy-Wenzig, E.M.; Jacob, M.; Schuehly, W.; Bauer, R. Phloroglucinol and terpenoid derivatives from Hypericum cistifolium and H. galioides (Hypericaceae). Front. Plant Sci., 2016, 7, 961.
[http://dx.doi.org/10.3389/fpls.2016.00961] [PMID: 27458464]
[49]
Hu, J.W.; Shi, M.J.; Wang, J.J.; Li, L.; Jiang, J.D.; Ji, T.F. Methylated polycyclic polyprenylated acylphloroglucinol derivatives from Hypericum ascyron. J. Nat. Prod., 2018, 81(11), 2348-2356.
[http://dx.doi.org/10.1021/acs.jnatprod.8b00176] [PMID: 30379546]
[50]
Ozkan, E.E.; Ozsoy, N.; Ozden, T.Y.; Ozhan, G.; Mat, A. Evaluation of chemical composition and in-vitro biological activities of three endemic Hypericum species from Anatolia (H. thymbrifolium, H. spectabile and H. pseudolaeve). Iran. J. Pharm. Res., 2018, 17(3), 1036-1046.
[PMID: 30127826]
[51]
Cirak, C.; Radusiene, J.; Jakstas, V.; Ivanauskas, L.; Seyis, F.; Yayla, F. Secondary metabolites of seven Hypericum species growing in Turkey. Pharm. Biol., 2016, 54(10), 2244-2253.
[http://dx.doi.org/10.3109/13880209.2016.1152277] [PMID: 26958815]
[52]
Booker, A.; Agapouda, A.; Frommenwiler, D.A.; Scotti, F.; Reich, E.; Heinrich, M. St John’s wort (Hypericum perforatum) products - an assessment of their authenticity and quality. Phytomedicine, 2018, 40, 158-164.
[http://dx.doi.org/10.1016/j.phymed.2017.12.012] [PMID: 29496168]
[53]
Apaydin, E.A.; Maher, A.R.; Shanman, R.; Booth, M.S.; Miles, J.N.; Sorbero, M.E.; Hempel, S. A systematic review of St. John’s wort for major depressive disorder. Syst. Rev., 2016, 5(1), 148.
[http://dx.doi.org/10.1186/s13643-016-0325-2] [PMID: 27589952]
[54]
Ng, Q.X.; Venkatanarayanan, N.; Ho, C.Y.X. Clinical use of Hypericum perforatum (St John’s wort) in depression: A meta-analysis. J. Affect. Disord., 2017, 210, 211-221.
[http://dx.doi.org/10.1016/j.jad.2016.12.048] [PMID: 28064110]
[55]
Nabavi, S.M.; Nabavi, S.F.; Sureda, A.; Caprioli, G.; Iannarelli, R.; Sokeng, A.J.T.; Braidy, N.; Khanjani, S.; Moghaddam, A.H.; Atanasov, A.G.; Daglia, M.; Maggi, F. The water extract of tutsan (Hypericum androsaemum L.) red berries exerts antidepressive-like effects and in vivo antioxidant activity in a mouse model of post-stroke depression. Biomed. Pharmacother., 2018, 99, 290-298.
[http://dx.doi.org/10.1016/j.biopha.2018.01.073] [PMID: 29353203]
[56]
Scheggi, S.; Marandino, A.; Del Monte, D.; De Martino, L.; Pelliccia, T.; Del Rosario Fusco, M.; Petenatti, E.M.; Gambarana, C.; De Feo, V. The protective effect of Hypericum connatum on stress-induced escape deficit in rat is related to its flavonoid content. Pharm. Biol., 2016, 54(9), 1782-1792.
[http://dx.doi.org/10.3109/13880209.2015.1127979] [PMID: 26731632]
[57]
Bonaterra, G.A.; Schwendler, A.; Hüther, J.; Schwarzbach, H.; Schwarz, A.; Kolb, C.; Abdel-Aziz, H.; Kinscherf, R. Neurotrophic, Cytoprotective, and anti-inflammatory effects of St. John’s Wort extract on differentiated mouse hippocampal HT-22 Neurons. Front. Pharmacol., 2018, 8, 955.
[http://dx.doi.org/10.3389/fphar.2017.00955] [PMID: 29403374]
[58]
Wang, H.; Zhang, W.; Gao, Q.; Cao, X.; Li, Y.; Li, X.; Min, Z.; Yu, Y.; Guo, Y.; Shuai, L. Extractive from Hypericum ascyron L promotes serotonergic neuronal differentiation in vitro. Stem Cell Res. (Amst.), 2018, 31, 42-50.
[http://dx.doi.org/10.1016/j.scr.2018.07.003] [PMID: 30015171]
[59]
Larit, F.; Elokely, K.M.; Chaurasiya, N.D.; Benyahia, S.; Nael, M.A.; León, F.; Abu-Darwish, M.S.; Efferth, T.; Wang, Y.H.; Belouahem-Abed, D.; Benayache, S.; Tekwani, B.L.; Cutler, S.J. Inhibition of human monoamine oxidase A and B by flavonoids isolated from two Algerian medicinal plants. Phytomedicine, 2018, 40, 27-36.
[http://dx.doi.org/10.1016/j.phymed.2017.12.032] [PMID: 29496172]
[60]
National Cancer Institute. https://www.cancer.gov/about-cancer/understanding/what-is-cancer (Accessed February 26, 2018).
[61]
Brito, L.C.; Berenger, A.L.R.; Figueiredo, M.R. An overview of anticancer activity of Garcinia and Hypericum. Food Chem. Toxicol., 2017, 109(Pt 2), 847-862.
[http://dx.doi.org/10.1016/j.fct.2017.03.053] [PMID: 28363851]
[62]
Menichini, G.; Alfano, C.; Marrelli, M.; Toniolo, C.; Provenzano, E.; Statti, G.A.; Nicoletti, M.; Menichini, F.; Conforti, F. Hypericum perforatum L. subsp. perforatum induces inhibition of free radicals and enhanced phototoxicity in human melanoma cells under ultraviolet light. Cell Prolif., 2013, 46(2), 193-202.
[http://dx.doi.org/10.1111/cpr.12020] [PMID: 23510474]
[63]
Kim, H.; Kim, S.W.; Seok, K.H.; Hwang, C.W.; Ahn, J.C.; Jin, J.O.; Kang, H.W. Hypericin-assisted photodynamic therapy against anaplastic thyroid cancer. Photodiagn. Photodyn. Ther., 2018, 24, 15-21.
[http://dx.doi.org/10.1016/j.pdpdt.2018.08.008] [PMID: 30118906]
[64]
Valletta, E.; Rinaldi, A.; Marini, M.; Franzese, O.; Roscetti, G. Distinct Hypericum perforatum L. total extracts exert different antitumour activity on erythroleukemic K562 cells. Phytother. Res., 2018, 32(9), 1803-1811.
[http://dx.doi.org/10.1002/ptr.6114] [PMID: 29785769]
[65]
Sarrou, E.; Giassafaki, L.P.; Masuero, D.; Perenzoni, D.; Vizirianakis, I.S.; Irakli, M.; Chatzopoulou, P.; Martens, S. Metabolomics assisted fingerprint of Hypericum perforatum chemotypes and assessment of their cytotoxic activity. Food Chem. Toxicol., 2018, 114, 325-333.
[http://dx.doi.org/10.1016/j.fct.2018.02.057] [PMID: 29499307]
[66]
You, M.K.; Kim, H.J.; Kook, J.H.; Kim, H.A.St.St. John’s Wort Regulates Proliferation and Apoptosis in MCF-7 Human Breast Cancer Cells by Inhibiting AMPK/mTOR and Activating the Mitochondrial Pathway. Int. J. Mol. Sci., 2018, 19(4), 996.
[http://dx.doi.org/10.3390/ijms19040966] [PMID: 29570671]
[67]
Sarimahmut, M.; Balikci, N.; Celikler, S.; Ari, F.; Ulukaya, E.; Guleryuz, G.; Ozel, M.Z. Evaluation of genotoxic and apoptotic potential of Hypericum adenotrichum Spach. in vitro. Regul. Toxicol. Pharmacol., 2016, 74, 137-146.
[http://dx.doi.org/10.1016/j.yrtph.2015.11.010] [PMID: 26617407]
[68]
Jabeur, I.; Tobaldini, F.; Martins, N.; Barros, L.; Martins, I.; Calhelha, R.C.; Henriques, M.; Silva, S.; Achour, L.; Santos-Buelga, C.; Ferreira, I.C.F.R. Bioactive properties and functional constituents of Hypericum androsaemum L.: A focus on the phenolic profile. Food Res. Int., 2016, 89(Pt 1), 422-431.
[http://dx.doi.org/10.1016/j.foodres.2016.08.040] [PMID: 28460934]
[69]
Napoli, E.; Siracusa, L.; Ruberto, G.; Carrubba, A.; Lazzara, S.; Speciale, A.; Cimino, F.; Saija, A.; Cristani, M. Phytochemical profiles, phototoxic and antioxidant properties of eleven Hypericum species - A comparative study. Phytochemistry, 2018, 152, 162-173.
[http://dx.doi.org/10.1016/j.phytochem.2018.05.003] [PMID: 29775867]
[70]
Li, X.M.; Luo, X.G.; Ma, N.; Li, K.; Li, W.; Ma, D.Y.; Zhang, T.C. Quality and antitumour activity evaluation of extract of Hypericum ascyron. Biomed. Chromatogr., 2015, 29(1), 47-52.
[http://dx.doi.org/10.1002/bmc.3169] [PMID: 24638934]
[71]
Li, X.M.; Luo, X.G.; He, J.F.; Wang, N.; Zhou, H.; Yang, P.L.; Zhang, T.C. Induction of apoptosis in human cervical carcinoma HeLa cells by active compounds from Hypericum ascyron L. Oncol. Lett., 2018, 15(3), 3944-3950.
[PMID: 29556280]
[72]
Bender, O.; Llorent-Martínez, E.J.; Zengin, G.; Mollica, A.; Ceylan, R.; Molina-García, L.; Fernández-de Córdova, M.L.; Atalay, A. Integration of in vitro and in silico perspectives to explain chemical characterization, biological potential and anticancer effects of Hypericum salsugineum: A pharmacologically active source for functional drug formulations. PLoS One, 2018, 13(6) e0197815
[http://dx.doi.org/10.1371/journal.pone.0197815] [PMID: 29864137]
[73]
Caprioli, G.; Alunno, A.; Beghelli, D.; Bianco, A.; Bramucci, M.; Frezza, C.; Iannarelli, R.; Papa, F.; Quassinti, L.; Sagratini, G.; Tirillini, B.; Venditti, A.; Vittori, S.; Maggi, F. Polar constituents and biological activity of the berry-like fruits from Hypericum androsaemum L. Front. Plant Sci., 2016, 7, 232.
[http://dx.doi.org/10.3389/fpls.2016.00232] [PMID: 26973675]
[74]
Okmen, G.; Balpınar, N. The biological activities of Hypericum perforatum L. Afr. J. Tradit. Complement. Altern. Med., 2016, 14(1), 213-218.
[http://dx.doi.org/10.21010/ajtcam.v14i1.23] [PMID: 28480399]
[75]
Marčetić, M.D.; Milenković, M.T.; Lakušić, D.V.; Lakušić, B.S. Chemical composition and antimicrobial activity of the essential oil and methanol extract of Hypericum aegypticum subsp. webbii (Spach) N. Robson. Chem. Biodivers., 2016, 13(4), 427-436.
[http://dx.doi.org/10.1002/cbdv.201500119] [PMID: 26923468]
[76]
Tocci, N.; Perenzoni, D.; Iamonico, D.; Fava, F.; Weil, T.; Mattivi, F. Extracts from Hypericum hircinum subsp. majus exert antifungal activity against a panel of sensitive and drug resistant clinical strains. Front. Pharmacol., 2018, 9, 382.
[http://dx.doi.org/10.3389/fphar.2018.00382] [PMID: 29755350]
[77]
Puthur, S.; Anoopkumar, A.N.; Rebello, S.; Aneesh, E.M. Hypericum japonicum: A double-headed sword to combat vector control and cancer. Appl. Biochem. Biotechnol., 2018, 186(1), 1-11.
[http://dx.doi.org/10.1007/s12010-018-2713-7] [PMID: 29476319]
[78]
Lyles, J.T.; Kim, A.; Nelson, K.; Bullard-Roberts, A.L.; Hajdari, A.; Mustafa, B.; Quave, C.L. The chemical and antibacterial evaluation of St. John’s Wort oil macerates used in Kosovar traditional medicine. Front. Microbiol., 2017, 8, 1639.
[http://dx.doi.org/10.3389/fmicb.2017.01639] [PMID: 28943862]
[79]
Sanna, C.; Scognamiglio, M.; Fiorentino, A.; Corona, A.; Graziani, V.; Caredda, A.; Cortis, P.; Montisci, M.; Ceresola, E.R.; Canducci, F.; Poli, F.; Tramontano, E.; Esposito, F. Prenylated phloroglucinols from Hypericum scruglii, an endemic species of Sardinia (Italy), as new dual HIV-1 inhibitors effective on HIV-1 replication. PLoS One, 2018, 13(3) e0195168
[http://dx.doi.org/10.1371/journal.pone.0195168] [PMID: 29601601]
[80]
Kumar, G.P.; Khanum, F. Neuroprotective potential of phytochemicals. Pharmacogn. Rev., 2012, 6(12), 81-90.
[http://dx.doi.org/10.4103/0973-7847.99898] [PMID: 23055633]
[81]
Oliveira, A.I.; Pinho, C.; Sarmento, B.; Dias, A.C. Neuroprotective activity of Hypericum perforatum and its major components. Front. Plant Sci., 2016, 7, 1004.
[http://dx.doi.org/10.3389/fpls.2016.01004] [PMID: 27462333]
[82]
Cao, Z.; Wang, F.; Xiu, C.; Zhang, J.; Li, Y. Hypericum perforatum extract attenuates behavioral, biochemical, and neurochemical abnormalities in Aluminum chloride-induced Alzheimer’s disease rats. Biomed. Pharmacother., 2017, 91, 931-937.
[http://dx.doi.org/10.1016/j.biopha.2017.05.022] [PMID: 28514831]
[83]
Kurt, B.Z.; Gazioğlu, I.; Sevgi, E.; Sönmez, F. Anticholinesterase, antioxidant, antiaflatoxigenic activities of ten edible wild plants from Ordu area, Turkey. Iran. J. Pharm. Res., 2018, 17(3), 1047-1056.
[PMID: 30127827]
[84]
Béjaoui, A.; Ben Salem, I.; Rokbeni, N.; M’rabet, Y.; Boussaid, M.; Boulila, A. Bioactive compounds from Hypericum humifusum and Hypericum perfoliatum: inhibition potential of polyphenols with acetylcholinesterase and key enzymes linked to type-2 diabetes. Pharm. Biol., 2017, 55(1), 906-911.
[http://dx.doi.org/10.1080/13880209.2016.1270973] [PMID: 28147885]
[85]
Borsoi, M.; Batassini, C.; Lazzaretti, C.; Silvestrin, R.B.; Betti, A.H.; Stein, A.C.; von Poser, G.L.; Rates, S.M.K.; Souza, T.M.E. Hypericum polyanthemum cyclohexane extract potentiates behavioral effects and neurodegeneration induced by nigral infusions of 6-hydroxydopamine in rats. Neurosci. Lett., 2018, 687, 177-182.
[http://dx.doi.org/10.1016/j.neulet.2018.09.048] [PMID: 30266672]
[86]
Keskin, C.; Aktepe, N.; Yükselten, Y.; Sunguroglu, A.; Boğa, M. In-vitro antioxidant, cytotoxic, cholinesterase inhibitory activities and anti-genotoxic effects of Hypericum retusum Aucher flowers, fruits and seeds methanol extracts in human mononuclear leukocytes. Iran. J. Pharm. Res., 2017, 16(1), 210-220.
[PMID: 28496476]
[87]
Cinci, L.; Di Cesare Mannelli, L.; Maidecchi, A.; Mattoli, L.; Ghelardini, C. Effects of Hypericum perforatum extract on oxaliplatin-induced neurotoxicity: in vitro evaluations. Z. Natforsch. C J. Biosci., 2017, 72(5-6), 219-226.
[http://dx.doi.org/10.1515/znc-2016-0194] [PMID: 28160544]
[88]
Bridi, H.; Dischkaln Stolz, E.; Maikon Corrêa de Barros, F.; Elingson da Silva Costa, B.; Guerini, L.; Maris Kuze Rates, S.; Lino von Poser, G. Antinociceptive ativity of phloroglucinol derivatives isolated from Southern Brazilian Hypericum species. Chem. Biodivers., 2018, 15(11) e1800266
[http://dx.doi.org/10.1002/cbdv.201800266] [PMID: 30156379]
[89]
Ozkan, E.E.; Ozsoy, N.; Ozden, T.Y.; Ozhan, G.; Mat, A. Evaluation of chemical Composition and in-vitro biological activities of three endemic Hypericum Species from Anatolia (H. thymbrifolium, H. spectabile and H. pseudolaeve). Iran. J. Pharm. Res., 2018, 17(3), 1036-1046.
[PMID: 30127826]
[90]
Novelli, M.; Menegazzi, M.; Beffy, P.; Porozov, S.; Gregorelli, A.; Giacopelli, D.; De Tata, V.; Masiello, P. St. John’s wort extract and hyperforin inhibit multiple phosphorylation steps of cytokine signaling and prevent inflammatory and apoptotic gene induction in pancreatic β cells. Int. J. Biochem. Cell Biol., 2016, 81(Pt A), 92-104.
[http://dx.doi.org/10.1016/j.biocel.2016.10.017] [PMID: 27780755]
[91]
Quispe, Y.N.G.; Hwang, S.H.; Wang, Z.; Zuo, G.; Lim, S.S. Screening in vitro targets related to diabetes in herbal extracts from Peru: identification of active compounds in Hypericum laricifolium Juss. by offline high-performance liquid chromatography. Int. J. Mol. Sci., 2017, 18(12), 2512.
[http://dx.doi.org/10.3390/ijms18122512] [PMID: 29186785]
[92]
Heinrich, M.; Lorenz, P.; Daniels, R.; Stintzing, F.C.; Kammerer, D.R. Lipid and phenolic constituents from seeds of Hypericum perforatum L. and Hypericum tetrapterum Fr. and their antioxidant activity. Chem. Biodivers., 2017, 14(8) e1700100
[http://dx.doi.org/10.1002/cbdv.201700100] [PMID: 28557380]
[93]
Mandrone, M.; Scognamiglio, M.; Fiorentino, A.; Sanna, C.; Cornioli, L.; Antognoni, F.; Bonvicini, F.; Poli, F. Phytochemical profile and α-glucosidase inhibitory activity of Sardinian Hypericum scruglii and Hypericum hircinum. Fitoterapia, 2017, 120, 184-193.
[http://dx.doi.org/10.1016/j.fitote.2017.06.020] [PMID: 28647480]
[94]
Ganji, A.; Salehi, I.; Sarihi, A.; Shahidi, S.; Komaki, A. Effects of Hypericum Scabrum extract on anxiety and oxidative stress biomarkers in rats fed a long-term high-fat diet. Metab. Brain Dis., 2017, 32(2), 503-511.
[http://dx.doi.org/10.1007/s11011-016-9940-9] [PMID: 27981406]
[95]
Ghosian Moghaddam, M.H.; Roghani, M.; Maleki, M. Effect of Hypericum perforatum aqueous extracts on serum lipids, aminotransferases, and lipid peroxidation in hyperlipidemic rats. Res. Cardiovasc. Med., 2016, 5(2) e31326
[PMID: 26949689]
[96]
Bridi, H.; Beckenkamp, A.; Ccana-Ccapatinta, G.V.; de Loreto Bordignon, S.A.; Buffon, A.; von Poser, G.L. Characterization of phloroglucinol‐enriched fractions of Brazilian Hypericum species and evaluation of their effect on human keratinocytes proliferation. Phytother. Res., 2017, 31(1), 62-68.
[http://dx.doi.org/10.1002/ptr.5727] [PMID: 27619474]
[97]
Yücel, A.; Kan, Y.; Yesilada, E.; Akın, O. Effect of St.John’s wort (Hypericum perforatum) oily extract for the care and treatment of pressure sores; a case report. J. Ethnopharmacol., 2017, 196, 236-241.
[http://dx.doi.org/10.1016/j.jep.2016.12.030] [PMID: 28011162]
[98]
Quispe, Y.N.G.; Hwang, S.H.; Wang, Z.; Lim, S.S. Screening of Peruvian medicinal plants for tyrosinase inhibitory properties: Identification of tyrosinase inhibitors in Hypericum laricifolium Juss. Molecules, 2017, 22(3), 402.
[http://dx.doi.org/10.3390/molecules22030402] [PMID: 28273864]
[99]
Ferrara, M.; Mungai, F.; Starace, F. St John’s wort (Hypericum perforatum)-induced psychosis: A case report. J. Med. Case Reports, 2017, 11(1), 137.
[http://dx.doi.org/10.1186/s13256-017-1302-7] [PMID: 28502251]
[100]
Valvassori, S.S.; Borges, C.; Bavaresco, D.V.; Varela, R.B.; Resende, W.R.; Peterle, B.R.; Arent, C.O.; Budni, J.; Quevedo, J. Hypericum perforatum chronic treatment affects cognitive parameters and brain neurotrophic factor levels. Br. J. Psychiatry, 2018, 40(4), 367-375.
[http://dx.doi.org/10.1590/1516-4446-2017-2271] [PMID: 30110089]
[101]
Yang, J.F.; Liu, Y.R.; Huang, C.C.; Ueng, Y.F. The time-dependent effects of St John’s Wort on cytochrome P450, uridine diphosphate-glucuronosyltransferase, glutathione S-transferase, and NAD(P)H-quinone oxidoreductase in mice. Yao Wu Shi Pin Fen Xi, 2018, 26(1), 422-431.
[http://dx.doi.org/10.1016/j.jfda.2017.01.004] [PMID: 29389584]
[102]
Kahyaoğlu, F.; Gökçimen, A.; Demirci, B. Investigation of the embryotoxic and teratogenic effect of Hypericum perforatum in pregnant rats. Turk. J. Obstet. Gynecol., 2018, 15(2), 87-90.
[http://dx.doi.org/10.4274/tjod.84429] [PMID: 29971184]
[103]
Hammami, I.; Ali, R.B.; Nahdi, A.; Kallech-Ziri, O.; Boussada, M.; El May, A.; El May, M.V. Chronic consumption of Hypericum humifusum leaf extracts impairs epididymis spermatozoa characters in association with oxidative stress in adult male Wistar rats. Biomed. Pharmacother., 2017, 93, 616-625.
[http://dx.doi.org/10.1016/j.biopha.2017.06.069] [PMID: 28686976]
[104]
Nahdi, A.; Hammami, I.; Ali, R.B.; Kallech-Ziri, O.; El May, A.; El May, M.V. Effect of Hypericum humifusum aqueous and methanolic leaf extracts on bioc,
[105]
Shakya, P.; Marslin, G.; Siram, K.; Beerhues, L.; Franklin, G. Elicitation as a tool to improve the profiles of high-value secondary metabolites and pharmacological properties of Hypericum perforatum. J. Pharm. Pharmacol., 2019, 71(1), 70-82.
[http://dx.doi.org/10.1111/jphp.12743] [PMID: 28523644]
[106]
Chrubasik-Hausmann, S.; Vlachojannis, J.; McLachlan, A.J. Understanding drug interactions with St John’s wort (Hypericum perforatum L.): Impact of hyperforin content. J. Pharm. Pharmacol., 2019, 71(1), 129-138.
[http://dx.doi.org/10.1111/jphp.12858] [PMID: 29411879]

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