1H NMR determination of hypericin and pseudohypericin in complex natural mixtures by the use of strongly deshielded OH groups

Analytica Chimica Acta
Evangelos C TatsisIoannis P Gerothanassis

Abstract

The (1)H NMR spectra of the commercially available compounds hypericin and its derivative pseudohypericin in CD(3)OH solutions indicate significantly deshielded signals in the region of 14-15 ppm. These resonances are attributed to the peri hydroxyl protons OH(6), OH(8) and OH(1), OH(13) of hypericins which participate in a strong six-membered ring intramolecular hydrogen bond with CO(7) and CO(14), respectively, and therefore, they are strongly deshielded. In the present work, we demonstrate that one-dimensional (1)H NMR spectra of hypericin and pseudohypericin, in Hypericum perforatum extracts show important differences in the chemical shifts of the hydroxyl groups with excellent resolution in the region of 14-15 ppm. The facile identification and quantification of hypericin and its derivative compound pseudohypericin was achieved, without prior HPLC separation, for two H. perforatum extracts from Greek cultivars and two commercial extracts: a dietary supplement, and an antidepressant medicine. The results were compared with those obtained from UV-vis and LC/MS measurements.

References

Aug 1, 1997·Journal of Chromatography. B, Biomedical Sciences and Applications·G PiperopoulosK P Zeller
Sep 5, 2002·Journal of Agricultural and Food Chemistry·V ExarchouD Boskou
Jan 2, 2007·Phytochemistry·Evangelos C TatsisIoannis P Gerothanassis

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Citations

Oct 22, 2011·Journal of Natural Products·Pantelis CharisiadisIoannis P Gerothanassis
Apr 10, 2012·Journal of Natural Products·Guido F PauliDavid C Lankin
Sep 4, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Pantelis CharisiadisIoannis P Gerothanassis
Sep 15, 2010·Journal of Pharmaceutical and Biomedical Analysis·Jordanka StanevaLjuba Evstatieva
Sep 11, 2009·Phytochemical Analysis : PCA·Andrea LubbeRobert Verpoorte
Aug 21, 2014·Magnetic Resonance in Chemistry : MRC·Pantelis CharisiadisIoannis P Gerothanassis
Jun 21, 2014·Analytical and Bioanalytical Chemistry·Stephen R DaviesJames M Hook
Jun 1, 2020·Current Pharmaceutical Design·Patricia Rocha de AraújoMarlus Chorilli
Jul 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Poul Erik Hansen

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