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)
Abstract
Hypericin is one of the most important bioactive substances present in Hypericum perforatum (Saint John’s Wort), which exhibits various biological activities such as inhibition of neuronal processes coupled with transmission of serotonin, dopamine, gamma-amino butyric acid and L-glutamine. This red-colored derivative of anthraquinone contains six benzene cycles and four hydroxy groups that polarize electron density in the conjugated double bond system and enable the molecule to act as a Lewis base in charge-transfer complexes. In this study, four stationary phases modified by the pentafluorophenyl group were selected to investigate the contribution of π-π interactions to the improvement of hypericin separation in comparison to the separation provided with a classical C18 based chromatographic column. In order to develop a suitable gradient chromatographic method for the quantification of hypericin, normal, polar organic and reverse elution modes were evaluated using high-performance liquid chromatography with ultraviolet-visible and mass spectrometry detection. It was disclosed in the analyses that the pentafluorophenyl stationary phase can separate hypericin from hyperforin, which was not possible to achieve with the C18 based stationary phase. The best analytical method found, employing the pentafluorophenyl stationary phase, showed sufficient linearity, accuracy and precision and was used for the determination of hypericin in Saint John’s Wort.
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Several natural products, mainly plant extracts, have been reported to be used in traditional medicine for neuroprotective, memory enhancing, and antiageing functions.
“Several natural products, mainly plants extracts, have been reported to be used in traditional medicine for neuroprotective, memory enhancing, and antiageing functions”
From Multi-target neuroprotective effects of herbal medicines for Alzheimer's disease (2022) · cites this paper as Doležal et al., 2019
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Multi-target neuroprotective effects of herbal medicines for Alzheimer's disease
Fernandes, F., Barroso, M. F., De Simone, A., Emriková, E., Dias-Teixeira, M., Pereira, J. P., Chlebek, J., Fernandes, V. C., Rodrigues, F., Andrisano, V., et al. (2022) · Journal of Ethnopharmacology · doi:10.1016/j.jep.2022.115107 · Cited by 45 · see citing works
- Authors
- Doležal, R., Houdková, I., Kalász, H., Andrýs, R., Novák, M., Maltsevskaya, N. V., Karásková, N., Kolář, K., Novotná, E., Kuča, K., & Žďárová Karasová, J.
- Affiliations
- University Hospital Hradec Králové (CZ)
- University of Hradec Králové (CZ)
- Semmelweis University (HU)
- State Budget Professional Education Institution, Moscow, Russia;
- Charles University (CZ)
- Biomedical Research Center, University Hospital Hradec Kralove, Hradec Kralove, Czech Republic;
- Corresponding author
- Doležal, Rafael
- Venue
- Analytical Letters
- Publisher
- Informa UK Limited
- Published
- 2019-02-27
- Volume
- 52
- Issue
- 11
- Pages
- 1788-1812
- ISSN
- 0003-2719 (ISSN-L)
- 1532-236X
- OpenAlex
- W2915250580
- Cited by
- 7
- References
- 28
- Citations by year
- 2023: 1 · 2022: 3 · 2021: 1 · 2020: 1 · 2019: 1
- FWCI
- 1.11
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Analytical Letters (publishedVersion)
- Funders
- University Hospital Hradec Kralove (00179906, SVV 260 416)
- Specific Research Project of Faculty of Science, University of Hradec Kralove (2108/2018)
- Topics
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Natural Compound Pharmacology Studies
- Physical Sciences › Chemistry › Spectroscopy › Analytical Chemistry and Chromatography
- Physical Sciences › Chemistry › Analytical Chemistry › Chromatography in Natural Products
- Keywords
- hypericin, Hypericum perforatum, C18 stationary phase, π-π stacking, hyperforin, gradient elution, mass spectrometry detection
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