Determination of Hypericin in Hypericum perforatum (St. John’s Wort) Using Classical C18 and Pentafluorophenyl Stationary Phases: Contribution of Pi–Pi Interactions to High-Performance Liquid Chromatography (HPLC)

Reference

• Barnes, J., L. A. Anderson, and J. D. Phillipson. 2001. St John’s Wort (Hypericum perforatum L.): A review of its chemistry, pharmacology and clinical properties. Journal of Pharmacy and Pharmacology 53 (5):583–600. doi:10.1211/0022357011775910.
   PubMed Web of Science ®Google Scholar
• Biber, A., H. Fischer, A. Romer, and S. S. Chatterjee. 1998. Oral bioavailability of hyperforin from hypericum extracts in rats and human volunteers. Pharmacopsychiatry 31 (S1):36–43. doi:10.1055/s-2007-979344.
   PubMedGoogle Scholar
• Chandrasekera, D. H., K. J. Welham, D. Ashton, R. Middleton, and M. Heinrich. 2005. Quantitative analysis of the major constituents of St John’s Wort with HPLC-ESI-MS. Journal of Pharmacy and Pharmacology 57 (12):1645–1652. doi:10.1211/jpp.57.12.0015.
   PubMed Web of Science ®Google Scholar
• Chatterjee, S. S., S. K. Bhattacharya, M. Wonnemann, A. Singer, and W. E. Muller. 1998. Hyperforin as a possible antidepressant component of hypericum extracts. Life Science 63 (6):499–510. doi:10.1016/S0024-3205(98)00299-9.
   PubMed Web of Science ®Google Scholar
• Çirak, C., J. Radušienė, L. Ivanauskas, and V. Janulis. 2007. Variation of bioactive secondary metabolites in hypericum origanifolium during its phenological cycle. Acta Physiologiae Plantarum 29 (3):197–203. doi:10.1007/s11738-007-0024-7.
   Web of Science ®Google Scholar
• Couceiro, M. A., F. Afreen, S. M. A. Zobayed, and T. Kozai. 2006. Variation in concentrations of major bioactive compounds of St. John’s Wort: Effects of harvesting time, temperature and germplasm. Plant Science 170 (1):128–134. doi:10.1016/j.plantsci.2005.08.011.
   Web of Science ®Google Scholar
• de los Reyes, G. C., and R. T. Koda. 2001. Development of a simple, rapid and reproducible HPLC assay for the simultaneous determination of hypericins and stabilized hyperforin in commercial St. John’s Wort preparations. Journal of Pharmaceutical and Biomedical Analysis 26 (5–6):959–965. doi:10.1016/S0731-7085(01)00449-6.
   PubMed Web of Science ®Google Scholar
• Denke, A., H. Schempp, D. Weiser, and E. F. Elstner. 2000. Biochemical activities of extracts from Hypericum perforatum L. 5th communication: Dopamine-beta-hydroxylase-product quantification by HPLC and inhibition by hypericins and flavonoids. Arzneimittelforschung 50 (5):415–419. doi:10.1055/s-0031-1300225.
   Web of Science ®Google Scholar
• Erdelmeier, C. A. 1998. Hyperforin, possibly the major non-nitrogenous secondary metabolite of Hypericum perforatum L. Pharmacopsychiatry 31 (S1):2–6. doi:10.1055/s-2007-979339.
   PubMedGoogle Scholar
• Gaster, B., and J. Holroyd. 2000. St john’s Wort for depression: A systematic review. Archives of Internal Medicine 160 (2):152–156. doi:10.1001/archinte.160.2.152.
   PubMedGoogle Scholar
• Gomez-Caravaca, A. M., V. Verardo, A. Berardinelli, E. Marconi, and M. F. Caboni. 2014. A chemometric approach to determine the phenolic compounds in different barley samples by two different stationary phases: A comparison between C18 and pentafluorophenyl core shell columns. Journal of Chromatography A 1355:134–142. doi:10.1016/j.chroma.2014.06.007.
   PubMed Web of Science ®Google Scholar
• Hohmann, M. S., R. D. Cardoso, V. Fattori, N. S. Arakawa, J. C. Tomaz, N. P. Lopes, R. Casagrande, and W. A. Verri. Jr. 2015. Hypericum perforatum reduces Paracetamol-Induced hepatotoxicity and lethality in mice by modulating inflammation and oxidative stress. Phytotherapy Research 29 (7):1097–1101. doi:10.1002/ptr.5350.
   PubMed Web of Science ®Google Scholar
• Hsu, W. L., H. W. Chung, C. Y. Wu, H. I. Wu, Y. T. Lee, E. C. Chen, W. Fang, and Y. C. Chang. 2015. Glutamate stimulates local protein synthesis in the axons of rat cortical neurons by activating alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) Receptors and metabotropic glutamate receptors. Journal of Biological Chemistry 290 (34):20748–20760. doi:10.1074/jbc.M115.638023.
   PubMed Web of Science ®Google Scholar
• Jendzelovska, Z., R. Jendzelovsky, B. Kucharova, and P. Fedorocko. 2016. Hypericin in the light and in the dark: Two sides of the same coin. Frontiers in Plant Science 7:560. doi:10.3389/fpls.2016.00560.
   PubMed Web of Science ®Google Scholar
• Kubin, A., F. Wierrani, U. Burner, G. Alth, and W. Grunberger. 2005. Hypericin-the facts about a controversial agent. Current Pharmaceutical Design 11 (2):233–253. doi:10.2174/1381612053382287.
   PubMed Web of Science ®Google Scholar
• Kusari, S., S. Sezgin, K. Nigutova, E. Cellarova, and M. Spiteller. 2015. Spatial chemo-profiling of hypericin and related phytochemicals in hypericum species using MALDI-HRMS imaging. Analytical and Bioanalytical Chemistry 407 (16):4779–4791. doi:10.1007/s00216-015-8682-6.
   PubMed Web of Science ®Google Scholar
• Liebes, L.,. Y. Mazur, D. Freeman, D. Lavie, G. Lavie, N. Kudler, S. Mendoza, B. Levin, H. Hochster, and D. Meruelo. 1991. A method for the quantitation of hypericin, an antiviral agent, in biological fluids by high-performance liquid chromatography. Analytical Biochemistry 195 (1):77–85. doi:10.1016/0003-2697(91)90298-8.
   PubMed Web of Science ®Google Scholar
• Muszynska, B., H. Ekiert, I. Kwiecien, A. Maslanka, R. Zodi, and L. Beerhues. 2014. Comparative analysis of therapeutically important indole compounds in in vitro cultures of Hypericum perforatum cultivars by HPLC and TLC analysis coupled with densitometric detection. Natural Product Communications 9 (10):1437–1440.
   PubMed Web of Science ®Google Scholar
• Nahrstedt, A., and V. Butterweck. 1997. Biologically active and other chemical constituents of the herb of Hypericum perforatum L. Pharmacopsychiatry 30 (S2):129–134. doi:10.1055/s-2007-979533.
   PubMedGoogle Scholar
• Nuevas-Paz, L., J. Molina-Torres, and S. Prieto-González. 2005. Determination of hypericin in hypericum species grown in Cuba. Acta Farmacéutica Bonaerense 24:89–90.
   Google Scholar
• Oliveira, A. I., C. Pinho, B. Sarmento, and A. C. Dias. 2016. Neuroprotective activity of Hypericum perforatum and its major components. Frontiers in Plant Science 7:1004. doi:10.3389/fpls.2016.01004.
   PubMed Web of Science ®Google Scholar
• Puri, S., G. Handa, A. K. Kalsotra, V. K. Gupta, A. S. Shawl, O. P. Suri, and G. N. Qazi. 2006. Preparative high-performance liquid chromatographic separation of naphthodianthrones from St. John’s Wort. Journal of Chromatographic Science 44 (4):177–180. doi:10.1093/chromsci/44.4.177.
   PubMed Web of Science ®Google Scholar
• Sakowska, J., M. Anyzewska, A. Lozak, A. Kowalczuk, and R. Jablczynska. 2016. Testing pharmaceutical release of active substances from medicinal products containing st. John’s Wort. Acta Poloniae Pharmaceutica 73 (2):395–401.
   PubMed Web of Science ®Google Scholar
• Schempp, C. M., B. Winghofer, M. Langheinrich, E. Schopf, and J. C. Simon. 1999. Hypericin levels in human serum and interstitial skin blister fluid after oral single-dose and steady-state administration of Hypericum perforatum extract (St. John’s Wort). Skin Pharmacology and Physiology 12 (5):299–304. doi:10.1159/000066256.
   Web of Science ®Google Scholar
• Schulz, H. U., M. Schurer, D. Bassler, and D. Weiser. 2005. Investigation of the bioavailability of hypericin, pseudohypericin, hyperforin and the flavonoids quercetin and isorhamnetin following single and multiple oral dosing of a hypericum extract containing tablet. Arzneimittelforschung 55 (1):15–22. doi:10.1055/s-0031-1296820.
   PubMed Web of Science ®Google Scholar
• Stamenkovic, J., I. Radojkovic, A. Đorđevic, O. Jovanovic, G. Petrovic, and G. Stojanovic. 2013. Optimization of HPLC method for the isolation of Hypericum perforatum L. methanol extract. Biologica Nyssana 4 (1–2):81–85.
   Google Scholar
• Suzuki, O., Y. Katsumata, M. Oya, S. Bladt, and H. Wagner. 1984. Inhibition of monoamine oxidase by hypericin. Planta Medica 50 (03):272–274. doi:10.1055/s-2007-969700.
   PubMedGoogle Scholar
• Torres-Salazar, D., J. Jiang, C. B. Divito, J. Garcia-Olivares, and S. G. Amara. 2015. A mutation in transmembrane domain 7 (TM7) of excitatory amino acid transporters disrupts the substrate-dependent gating of the intrinsic anion conductance and drives the channel into a constitutively open state. Journal of Biological Chemistry 290 (38):22977–22990. doi:10.1074/jbc.M115.660860.
   PubMed Web of Science ®Google Scholar
• Walker, L., T. Sirvent, D. Gibson, and N. Vance. 2001. Regional differences in hypericin and pseudohypericin concentrations and five morphological traits among Hypericum perforatum plants in the northwestern United States. Canadian Journal of Botany 79 (10):1248–1255. doi:10.1139/b01-103.
   Google Scholar
• Wolfle, U., G. Seelinger, and C. M. Schempp. 2014. Topical application of St. John’s Wort (Hypericum perforatum). Planta Medica 80 (2–3):109–120. doi:10.1055/s-0033-1351019.
   PubMed Web of Science ®Google Scholar