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Published June 30, 2020 | Version v1
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Metabolomic fingerprinting and genetic discrimination of four Hypericum taxa from Greece

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  • 1. ∗ & Laboratory of Pharmacognosy and Chemistry of Natural Products, Department of Pharmacy, University of Patras, 26504 Patras, Greece

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Zeliou, Konstantina, Koui, Eirini-Maria, Papaioannou, Charikleia, Koulakiotis, Nikolaos Stavros, Iatrou, Gregoris, Tsarbopoulos, Anthony, Papasotiropoulos, Vassilis, Lamari, Fotini N. (2020): Metabolomic fingerprinting and genetic discrimination of four Hypericum taxa from Greece. Phytochemistry (112290) 174: 1-15, DOI: 10.1016/j.phytochem.2020.112290, URL: http://dx.doi.org/10.1016/j.phytochem.2020.112290

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urn:lsid:plazi.org:pub:FFE94C39FFAF9973FFC55603FFE3FF8A

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Figure: 10.5281/zenodo.8295052 (DOI)
Dataset: http://table.plazi.org/id/DF06D5DFFFAD9971FFA156A2FCCDFF41 (URL)
Dataset: http://table.plazi.org/id/DF06D5DFFFAB9977FFA4578BFCE6FE3D (URL)
Dataset: http://table.plazi.org/id/DF06D5DFFFA89974FFA1522EFB59FBD2 (URL)
Figure: 10.5281/zenodo.8295054 (DOI)
Figure: 10.5281/zenodo.8295056 (DOI)
Figure: 10.5281/zenodo.8295058 (DOI)

References

  • Adams, R.P. (Ed.), 2012. Identification of Essential Oil Components by Gas Chromatography Mass Spectrometry, fourth ed. (Allured, CarolStream, IL).
  • Agapouda, A., Booker, A., Kiss, T., Hohmann, J., Heinrich, M., Csupor, D., 2019. Quality control of Hypericum perforatum L. analytical challenges and recent progress. J. Pharm. Pharmacol. 71, 15-37.
  • Alali, F.Q., Tawaha, K., 2009. Dereplication of bioactive constituents of the genus Hypericum using LC-(+)-ESI-MS and LC-PDA techniques: Hypericum triquetrifolium as a case study. Saudi Pharmaceut. J. 17, 269-274.
  • Alali, F.Q., Tawaha, K., Gharaibeh, M., 2009. LC-MS and LC-PDA analysis of Hypericum empetrifolium and Hypericum sinaicum. Z. Naturforsch. C Biosci. 64, 476-482.
  • Ayan, A.K., Cirak, C., 2008. Hypericin and pseudohypericin contents in some Hypericum species growing in Turkey. Pharm. Biol. 46, 288-291.
  • Aziz, N., Sauve, R.J., Long, D., Cherry, M., 2006. Genetic and phytochemical diversity assessment among eleven Hypericum accessions via AFLP and HPLC analyses. J. Herbs, Spices, Med. Plants 12, 97-105.
  • Baenziger, P.S., Bakhsh, A., Lorenz, A., Walia, H., 2014. Bridging conventional breeding and genomics for a more sustainable wheat production. In: In: Tuberosa, R. (Ed.), Crop Productivity, Food Security and Nutritional Quality, vol. 2. Springer Netherlands, pp. 185-209.
  • Bardhi, N., Stefkov, G., Karapandzova, M., Cvetkovikj, I., Kulevanova, S., 2015. Essential oil composition of indigenous populations of Hypericum perforatum L. from Southern Albania. Maced. J. Chem. Chem. Eng. 34, 333-341.
  • Benkiki, N., Kabouche, Z., Tillequin, F., Verite, P., Chosson, E., Sequin, E., 2003. A new polyisoprenylated phloroglucinol derivative from Hypericum perfoliatum (Clusiaceae). Z. Naturforsch. C Biosci. 58, 655-658.
  • Bertoli, A., Menichini, F., Mazzeti, M., Sinellu, G., Moelli, I., 2003. Volatile constituents of the leaves and flowers of Hypericum triquetrifolium Turra. Flavour Fragrance J. 18, 91-94.
  • Bertoli, A., Cirak, C., Teixeira da Silva, J.A., 2011. Hypericum species as sources of valuable essential oils. Med. Aromat. Plant Sci. Biotechnol. 5 (Special Issue1), 29-47.
  • Bertoli, A., Cirak, C., Seyis, F., 2018. Hypericum spp. volatile profiling and the potential significance in the quality control of new valuable raw material. Microchem. J. 136, 94-100.
  • Blattner, F.R., 1999. Direct amplification of the entire ITS region from poorly preserved plant material using recombinant PCR. Biotechniques 27, 1180-1186.
  • Booker, A., Agapouda, A., Frommenwiler, D.A., Scotti, F., Reich, E., Heinrich, M., 2018. St John's wort (Hypericum perforatum) products - an assessment of their authenticity and quality. Phytomedicine 40, 158-164.
  • Bozin, B., Kladar, N., Grujic, N., Anackov, G., Samojlik, I., Gavaric, N., Conic, B.S., 2013. Impact of origin and biological source on chemical composition, anticholinesterase and antioxidant properties of some St. John's wort species (Hypericum spp., Hypericaceae) from the Central Balkans. Mol. Basel Switz. 18, 11733-11750.
  • Bridi, H., Meirelles, G.C., von Poser, G.L., 2018. Structural diversity and biological activities of phloroglucinol derivatives from Hypericum species. Phytochemistry 155, 203-232.
  • Cardona, M.L., Fernandez, M.I., Pedro, J.R., Serrano, A., 1990. Xanthones from Hypericum reflexum. Phytochemistry 29, 3003-3006.
  • Cardona, M.L., Fernandez, M.I., Pedro, J.R., Serrano, A., 1993. Spiroterpenoids from Hypericum reflexum. Phytochemistry 33, 1185-1187.
  • Cheng, T., Xu, C., Lei, L., Li, C., Zhang, Y., Zhou, S., 2016. Barcoding the kingdom Plantae: new PCR primers for ITS regions of plants with improved universality and specificity. Mol. Ecol. Resour. 16, 138-149.
  • Chrubasik-Hausmann, S., Vlachojannis, J., McLachlan, A.J., 2019. Understanding drug interactions with St John's wort (Hypericum perforatum L.): impact of hyperforin content. J. Pharm. Pharmacol. 71, 129-138.
  • Cirak, C., Bertoli, A., Pistelli, L., Seyis, F., 2010. Essential oil composition and variability of Hypericum perforatum from wild populations of northern Turkey. Pharm. Biol. 48, 906-914.
  • Cirak, C., Radusiene, J., Ivanauskas, L., Jakstas, V., 2014. Changes in the content of bioactive substances among Hypericum montbretii populations from Turkey. Rev. Bras. Farmacogn. 24, 20-24.
  • Cirak, C., Radusiene, J., Ivanauskas, L., Jakstas, V., Camas, N., 2015. Population variability of main secondary metabolites in Hypericum lydium Boiss. (Hypericaceae). Iran. J. Pharm. Res. (IJPR) 14, 969-978.
  • Cirak, C., Radusiene, J., Jakstas, V., Ivanauskas, L., Yayla, F., Seyis, F., Camas, N., 2016. Secondary metabolites of Hypericum species from the Drosanthe and Olympia sections. South Afr. J. Bot. 104, 82-90.
  • Costa, J., Campos, B., Amaral, J.S., Nunes, M.E., Beatriz, M., Oliveira, P.P., Mafra, I., 2016. HRM analysis targeting ITS1 and matK loci as potential DNA mini-barcodes for the authentication of Hypericum perforatum and Hypericum androsaemum in herbal infusions. Food Contr. 6, 105-114.
  • Couladis, M., Baziou, P., Petrakis, P.V., Harvala, C., 2001. Essential oil composition of Hypericum perfoliatum L. growing in different locations in Greece. Flavour Fragrance J. 16, 204-206.
  • Crockett, S.L., 2010. Essential oil and volatile components of the genus Hypericum (Hypericaceae). Nat. Prod. Commun. 5, 1493-1506.
  • Crockett, S.L., Robson, N.K., 2011. Taxonomy and chemotaxonomy of the genus Hypericum. Med. Aromat. Plant Sci. Biotechnol. 5 (Special Issue 1), 1-13.
  • Diniz-Filho, J.A.F., Soares, T.N., Lima, J.S., Dobrovolski, R., Landeiro, V.L., de Campos Telles, M.P., Rangel, T.F., Bini, L.M., 2013. Mantel test in population genetics. Genet. Mol. Biol. 36, 475-485.
  • Doyle, J.J., Doyle, J.L., 1990. Isolation of plant DNA from fresh tissue. Focus 12, 13-15. European Medicines Agency, 2019. https://www.ema.europa.eu/en/medicines/herbal/ hyperici-herba, Accessed date: 25 January 2020.
  • Farag, M.A., Wessjohann, L.A., 2012. Metabolome classification of commercial Hypericum perforatum (St. Johnʼs Wort) preparations via UPLC-qTOF-MS and chemometrics. Planta Med. 78, 488-496.
  • Fuzzati, N., Gabetta, B., Strepponi, I., Villa, F., 2001. High-performance liquid chromatography-electrospray ionization mass spectrometry and multiple mass spectrometry studies of hyperforin degradation products. J. Chromatogr. A 926, 187-198.
  • Ghiasvand, A., Shadabi, S., Hajipour, S., Nasirian, A., Borzouei, M., Hassani-Moghadam, E., Hashemi, P., 2016. Comparison of ultrasound-assisted headspace solid-phase microextraction and hydrodistillation for the identification of major constituents in two species of Hypericum. J. Chromatogr. Sci. 54, 264-270.
  • Gudzic, B., Dordevic, S., Palic, R., Stojanovic, G., 2001. Essential oils of Hypericum olympicum L. and Hypericum perforatum L. Flavour Fragrance J. 16, 201-203.
  • 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., 2017. Tricyclic polyprenylated acylphloroglucinols from st John's wort, Hypericum perforatum. J. Nat. Prod. 80, 1493-1504.
  • Hajdari, A., Mustafa, B., Nebija, D., Kashtanjeva, A., Widelski, J., Glowniak, K., Novak, J., 2014. Essential oil composition and variability of Hypericum perforatum L. from wild population in Kosovo. Curr. Issues Pharm. Med. Sci. 27, 51-54.
  • Hashida, W., Tanaka, N., Kashiwada, Y., Sekiya, M., Ikeshiro, Y., Takaishi, Y., 2008. Tomoeones A-H, cytotoxic phloroglucinol derivatives from Hypericum ascyron. Phytochemistry 69, 2225-2230.
  • Helmja, K., Pussa, T., Orav, A., Viitak, A., Levandi, T., Kaljurand, M., 2011. Variation in the composition of the essential oils, phenolic compounds and mineral elements of Hypericum perforatum L. growing in Estonia. Nat. Prod. Res. 25, 496-510.
  • Hood, G.M., 2011. PopTools Version 3.2.5. Retrieved from. http://www.poptools.org, Accessed date: 8 February 2019.
  • Hosni, K., Msaada, K., Taarit, M.B., Chahed, T., Marzouk, B., 2007. Essential oil composition of Hypericum triquetrifolium Turra aerial parts. Ital. J. Biochem. 56, 40-46.
  • Hosni, K., Msaada, K., Taarit, M.B., Ouchikha, O., Kallel, M., Marzouk, B., 2008. Essential composition of Hypericum perfoliatum L., and Hypericum tomentosum L. growing wild in Tunisia. Ind. Crop. Prod. 27, 308-314.
  • Hosni, K., Msaada, K., Taarit, M.B., Hammami, M., Marzouk, B., 2010. Bioactive components of three Hypericum species from Tunisia: a comparative study. Ind. Crop. Prod. 31, 158-163.
  • Hosni, K., Msaada, K., Taarit, M.B., Marzouk, B., 2011. Phenological variations of secondary metabolites from Hypericum triquetrifolium Turra. Biochem. Systemat. Ecol. 39, 43-50.
  • Jendzelovska, Z., Jendzelovsky, R., Kucharova, B., Fedorocko, P., 2016. Hypericin in the light and in the dark: two sides of the same coin. Front. Plant Sci. 7, 560.
  • Jurgenliemk, G., Nahrstedt, A., 2002. Phenolic compounds from Hypericum perforatum. Planta Med. 68, 88-91.
  • Katajamaa, M., Miettinen, J., Oresic, M., 2006. MZmine: toolbox for processing and visualization of mass spectrometry based molecular profile data. Bioinformatics 22, 634-636.
  • Kitanov, M.K., 2001. Hypericin and pseudohypericin in some Hypericum species. Biochem. Systemat. Ecol. 29, 171-178.
  • Kumar, S., Stecher, G., Tamura, K., 2016. MEGA7: molecular evolutionary genetics analysis version 7.0 for bigger datasets. Mol. Biol. Evol. 33, 1870-1874.
  • China Plant BOL Group,Li, D.Z., Gao, L.M., Li, H.T., Wang, H., Ge, X.J., Liu, J.Q., Chen, Z.D., Zhou, S.L., Chen, S.L., Yang, J.B., Fu, C.X., Zeng, C.X., Yan, H.F., Zhu, Y.J., Sun, Y.S., Chen, S.Y., Zhao, L., Wang, K., Yang, T., Duan, G.W., 2011. Comparative analysis of a large dataset indicates that internal transcribed spacer (ITS) should be incorporated into the core barcode for seed plants. Proc. Natl. Acad. Sci. U.S.A. 108, 19641-19646.
  • Maggi, F., Cecchini, C., Cresci, A., Coman, M.M., Tirillini, B., Sagratini, G., Papa, F., Vittori, S., 2010. Chemical composition and antimicrobial activity of the essential oils from several Hypericum taxa (Guttiferae) growing in central Italy (Appennino Umbro-Marchigiano). Chem. Biodivers. 7, 447-466.
  • Mamemura, T., Tanaka, N., Shibazaki, A., Gonoi, T., Kobayashi, J., 2011. Yojironins A-D, meroterpenoids and prenylated acylphloroglucinols from Hypericum yojiroanum. Tetrahedron Lett. 52, 3575-3578.
  • Mathis, C., Ourisson, G., 1964. Etude chimio-taxonomique du genre Hypericum II. Identification de constituants de diverses huiles essentielles d' Hypericum. Phytochemistry 3, 115-131.
  • Mc William, H., Li, W., Uludag, M., Squizzato, S., Park, Y.M., Buso, N., Cowley, A.P., Lopez, R., 2013. Analysis tool web services from the EMBL-EBI. Nucleic Acids Res. 41 (Web Server issue) W597-600.
  • Meseguer, A.S., Aldasoro, J.J., Sanmartin, I., 2013. Bayesian inference of phylogeny, morphology and range evolution reveals a complex evolutionary history in St. John's wort (Hypericum). Mol. Phylogenet. Evol. 67, 379-403.
  • Mitsopoulou, K.P., Vidali, V.P., Maranti, A., Couladouros, E.A., 2015. Isolation and structure elucidation of hyperibine j [revised structure of adhyperfirin (7-deprenyl-13-methylhyperforin)]: synthesis of hyperibone. J. Eur. J. Org. Chem. 2, 287-290.
  • Morshedloo, M.R., Ebadi, A., Maggi, F., Fattahi, R., Yazdani, D., Jafari, M., 2015. Chemical characterization of the essential oil compositions from Iranian populations of Hypericum perforatum L. Ind. Crop. Prod. 76, 565-573.
  • Napoli, E., Siracusa, L., Ruberto, G., Carrubbba, A., Lazzara, S., Speciale, A., Cimino, F., Saija, A., Cristani, M., 2018. Phytochemical profiles, phototoxic and antioxidant properties of eleven Hypericum species- A comparative study. Phytochemistry 152, 162-173.
  • Naveed, M., Hejazi, V., Abbas, M., Kamboh, A.A., Khan, G.J., Shumzaid, M., Ahmad, F., Babazadeh, D., Fang Fang, X., Modarresi-Ghazani, F., WenHua, L., XiaoHui, Z., 2018. Chlorogenic acid (CGA): a pharmacological review and call for further research. Biomed. Pharmacother. 97, 67-74.
  • Ng, Q.X., Venkatanarayanan, N., Ho, C.Y., 2017. Clinical use of Hypericum perforatum (St John's wort) in depression: a meta-analysis. J. Affect. Disord. 210, 211-221.
  • Nurk, N.M., Crockett, S.L., 2011. Morphological and phytochemical diversity among Hypericum species of the Mediterranean basin. Med. Aromat. Plant Sci. Biotechnol. 5 (Special Issue 1), 14-28.
  • Nurk, N.M., Madrinan, S., Carine, M.A., Chase, M.W., Blattner, F.R., 2013. Molecular phylogenetics and morphological evolution of St. John's wort (Hypericum; Hypericaceae). Mol. Phylogenet. Evol. 66, 1-16.
  • Petrakis, P.V., Couladis, M., Roussis, V., 2005. A method for detecting the biosystematic significance of the essential oil composition: the case of five Hellenic Hypericum L. species. Biochem. Systemat. Ecol. 33, 873-898.
  • Ploss, O., Petereit, F., Nahrstedt, A., 2001. Procyanidins from the herb of Hypericum perforatum. Pharmazie 56, 509-511.
  • Pluskal, T., Castillo, S., Villar-Briones, A., Oresic, M., 2010. MZmine 2: modular framework for processing, visualizing, and analyzing mass spectrometry based molecular profile data. BMC Bioinf. 11, 395.
  • Porzel, A., Farag, M.A., Mulbradt, J., Wessjohann, L.A., 2014. Metabolite profiling and fingerprinting of Hypericum species: a comparison of MS and NMR metabolomics. Metabolomics 10, 574-588.
  • Raclariu, A.C., Paltinean, R., Vlase, L., Labarre, A., Manzanilla, V., Ichim, M.C., Crisan, G., Brysting, A.K., de Boer, H., 2017. Comparative authentication of Hypericum perforatum herbal products using DNA metabarcoding, TLC and HPLC-MS. Sci. Rep. 7, 1291.
  • Radulovic, N.S., Blagojevic, P.D., 2012. Chemical composition of Hypericum rumeliacum Boiss. essential oil. A new chemotype of this pharmacologically valuable species? Chem. Biodivers. 9, 2324-2341.
  • Radulovic, N.S., Ethorthevic, A.S., Palic, R.M., 2010. The intrasection chemotaxonomic placement of Hypericum elegans Stephan ex Willd. inferred from essential oil chemical composition. Chem. Biodivers. 7, 943-952.
  • Radusiene, J., Judzentiene, A., Bernotiene, G., 2005. Essential oil composition and variability of Hypericum perforatum L. growing in Lithuania. Biochem. Systemat. Ecol. 33, 113-124.
  • Rusalepp, L., Raal, A., Pussa, T., Maeorg, U., 2017. Comparison of chemical composition of Hypericum perforatum and H. maculatum in Estonia. Biochem. Systemat. Ecol. 67, 171-177.
  • Saddiqe, Z., Naeem, I., Maimoona, A., 2010. A review of the antibacterial activity of Hypericum perforatum L. J. Ethnopharmacol. 131 (3), 511-521.
  • Sajjadi, S.E., Mehregan, I., Taheri, M., 2015. Essential oil composition of Hypericum triquetrifolium Turra growing wild in Iran. Res. Pharm. Sci. 10, 90-94.
  • Sarrou, E., Giassafaki, L.P., Mauero, D., Perenzoni, D., Vizirianakis, I.S., Irakli, M., Chatzopoulou, P., Martens, S., 2018. Metabolomic assisted fingerprint of Hypericum perforatum chemotypes and assessment of their cytotoxic activity. Food Chem. Toxicol. 114, 325-333.
  • Schmidt, S., Jorgenliemk, G., Skaltsa, H., Heilmann, J., 2012a. Phloroglucinol derivatives from Hypericum empetrifolium with antiproliferative activity on endothelial cells. Phytochemistry 77, 218-225.
  • Schmidt, S., Jorgenliemk, G., Schmidt, T.J., Skaltsa, H., Heilmann, J., 2012b. Bi-, tri-, and polycyclic acylphloroglucinols from Hypericum empetrifolium. J. Nat. Prod. 75, 1697-1705.
  • Scotti, F., Lobel, K., Booker, A., Heinrich, M., 2019. St. John's wort (Hypericum perforatum) products - how variable is the primary material? Front. Plant Sci. 9, 1973.
  • Seger, C., Rompp, H., Sturm, S., Haslinger, E., Schmidt, P.C., Hadacek, F., 2004. Characterization of supercritical fluid extracts of st. John's wort (Hypericum perforatum L.) by HPLC-MS and GC-MS. Eur. J. Pharmaceut. Sci. 21, 453-463.
  • Shiu, W.K., Rahman, M.M., Curry, J., Stapleton, P., Zloh, M., Malkinson, J.P., Gibbons, S., 2012. Antibacterial acylphloroglucinols from Hypericum olympicum. J. Nat. Prod. 75, 336-343.
  • Smelcerovic, A., Verma, V., Spiteller, M., Ahmad, S.M., Puri, S.C., Qazi, G.N., 2006. Phytochemical analysis of six Hypericum species from Serbia. Biochem. Systemat. Ecol. 67, 171-177.
  • Smelcerovic, A., Spiteller, M., Ligon, A.P., Smelcerovic, Z., Raabe, N., 2007. Essential oil composition of Hypericum L. species from Southeastern Serbia and their chemotaxonomy. Biochem. Systemat. Ecol. 35, 99-113.
  • Sumner, L.W., Amberg, A., Barrett, D., Beale, M.H., Beger, R., Daykin, C.A., Fan, T.W.M., Fiehn, O., Goodacre, R., Griffin, J.L., Hankemeier, T., Hardy, N., Harnly, J., Higashi, R., Kopka, J., Lane, A.N., Lindon, J.C., Mrriott, P., Nicholls, A.W., Reily, M.D., Thaden, J.J., Viant, M.R., 2007. Proposed minimum reporting standards for chemical analysis. Metabolomics 3, 211-221.
  • Swofford, D.L., 2003. PAUP*: Phylogenetic Analysis Using Parsinomy (And Other Methods). Ver 4.0beta10. Sinauer Associates, Sunderland, MA.
  • Tanaka, N., Kashiwada, Y., Kim, S.-Y., Sekiya, M., Ikeshiro, Y., Takaishi, Y., 2009. Xanthones from Hypericum chinense and their cytotoxicity evaluation. Phytochemistry 70, 1456-1461.
  • Tatsis, E.C., Boeren, S., Exarchou, V., Troganis, A.N., Vervoort, J., Gerothanassis, I.P., 2007. Identification of the major constituents of Hypericum perforatum by LC/SPE/ NMR and/or LC/MS. Phytochemistry 68, 383-393.
  • Tawaha, K., Gharaibeh, M., El-Elimat, T., Alali, F.Q., 2010. Determination of hypericin and hyperforin content in selected Jordanian Hypericum species. Ind. Crop. Prod. 32, 241-245.
  • Touafek, O., Nacer, A., Kabouche, A., Kabouche, Z., 2005. Analysis of the essential oil of Algerian Hypericum perfoliatum (L). Flavour Fragrance J. 20, 669-670.
  • Varga, Z.V., Matyas, C., Erdelyi, K., Cinar, R., Nieri, D., Chicca, A., Nemeth, B.T., Paloczi, J., Lajtos, T., Corey, L., Hasko, G., Gao, B., Kunos, G., Gertsch, J., Pacher, P., 2018. β-Caryophyllene protects against alcoholics tea to hepatitis by attenuating inflammation and metabolic dysregulation in mice. Br. J. Pharmacol. 175, 320-334.
  • Volkov, I.B., 2018. Phytochemical and Pharmacological Study of Hypericum Triquetrifolium Turra. PhD Thesis (supervision: Prof. Dr. Jorg Heilmann). Pharmaceutical Biology department, Institute of Pharmacy, University of Regensburg urn:nbn:de:bvb:355-epub-352626.
  • Wu, Q.L., Wang, S.P., Du, L.-J., Yang, J.-S., Xiao, P.-G., 1998. Xanthones from Hypericum japonicum and H. henryi. Phytochemistry 49, 1395-1402.
  • Zeliou, K., Kontaxis, N.I., Margianni, E., Petrou, C., Lamari, F.N., 2017. Analysis of St. John's wort extracts, infusions and final products revisited: simultaneous HPLC determination of the major eleven ingredients with a fully validated method. J. Chromatogr. Sci. 55, 805-812.
  • Zorzetto, C., Sanchez-Mateo, C.C., Rabanal, R.M., Lupidi, G., Petrelli, D., Vitali, L.A., Bramucci, M., Quassinti, L., Caprioli, G., Papa, F., Ricciutelli, M., Sagratini, G., Vittori, S., Maggi, F., 2015. Phytochemical analysis and in vitro biological activity of three Hypericum species from the Canary Islands (Hypericum reflexum, Hypericum canariense and Hypericum grandifolium). Fitoterapia 100, 95-109.