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Open AccessArticle

Chemical Composition and Immunomodulatory Activity of Hypericum perforatum Essential Oils

1
Department of Microbiology and Immunology, Montana State University, Bozeman, MT 59717, USA
2
Department of Pharmacognosy, Faculty of Pharmacy, Anadolu University, Eskişehir 26470, Turkey
3
Medicinal Plant, Drug and Scientific Research and Application Center (AUBIBAM), Anadolu University, Eskişehir 26470, Turkey
4
Kizhner Research Center, Tomsk Polytechnic University, Tomsk 634050, Russia
5
Scientific Research Institute of Biological Medicine, Altai State University, Barnaul 656049, Russia
*
Author to whom correspondence should be addressed.
Running title: H. perforatum Essential Oils Modulate Neutrophils.
Biomolecules 2020, 10(6), 916; https://doi.org/10.3390/biom10060916
Received: 25 May 2020 / Revised: 11 June 2020 / Accepted: 12 June 2020 / Published: 17 June 2020
Hypericum L. (Hypericaceae) extracts have been used for their therapeutic effects; however, not much is known about the immunomodulatory activity of essential oils extracted from this plant. We isolated essential oils from the flowers and leaves of H. perforatum and analyzed their chemical composition and innate immunomodulatory activity. Analysis of flower (HEOFl) versus leaf (HEOLv) essential oils using gas chromatography–mass spectrometry revealed that HEOFl was comprised mainly of monoterpenes (52.8%), with an abundance of oxygenated monoterpenes, including cis-p-menth-3-en-1,2-diol (9.1%), α-terpineol (6.1%), terpinen-4-ol (7.4%), and limonen-4-ol (3.2%), whereas the sesquiterpenes were found in trace amounts. In contrast, HEOLv was primarily composed of sesquiterpenes (63.2%), including germacrene D (25.7%) and β-caryophyllene (9.5%). HEOLv also contained oxygenated monoterpenes, including terpinen-4-ol (2.6%), while monoterpene hydrocarbons were found in trace amounts. Both HEOFl and HEOLv inhibited neutrophil Ca2+ mobilization, chemotaxis, and reactive oxygen species (ROS) production, with HEOLv being much more active than HEOFl. Furthermore, the pure sesquiterpenes germacrene D, β-caryophyllene, and α-humulene also inhibited these neutrophil responses, suggesting that these compounds represented the active components of HEOLv. Although reverse pharmacophore mapping suggested that potential protein targets of germacrene D, β-caryophyllene, bicyclogermacrene, and α-humulene could be PIM1 and mitogen-activated protein kinase (MAPK)-activated protein kinase 2 (MAPKAK2), a kinase binding affinity assay did not support this finding, implying that other biological targets are involved. Our results provide a cellular and molecular basis to explain at least part of the beneficial immunotherapeutic properties of the H. perforatum essential oils. View Full-Text
Keywords: Hypericum perforatum; essential oil; calcium flux; neutrophil; chemotaxis; reactive oxygen species; sesquiterpene; anti-inflammatory Hypericum perforatum; essential oil; calcium flux; neutrophil; chemotaxis; reactive oxygen species; sesquiterpene; anti-inflammatory
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Schepetkin, I.A.; Özek, G.; Özek, T.; Kirpotina, L.N.; Khlebnikov, A.I.; Quinn, M.T. Chemical Composition and Immunomodulatory Activity of Hypericum perforatum Essential Oils. Biomolecules 2020, 10, 916.

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