Chemical Composition and Immunomodulatory Activity of Hypericum perforatum Essential Oils

Abstract

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.

Essential Oils from Monarda fistulosa: Chemical Composition and Activation of Transient Receptor Potential A1 (TRPA1) Channels

“…The chemical composition and biological activity of essential oils can be affected by many factors, including which part of the plant is used for essential oil isolation [39]. Indeed, we observed differences in the essential oil composition in flowers and leaves from Ferula iliensis [40] and Hypericum perforatum [41]. Thus, we extracted essential oils from M. fistulosa flowers (MEO Fl ) and leaves (MEO Lv ).…”

Chemical Composition and New Biological Activities of Essential Oil and Hydrosol of Hypericum perforatum L. ssp. veronense (Schrank) H. Lindb

“…Hypericum perforatum L. or St. John's wort (Clusiaceae) is a perennial rhizomatous herb traditionally used in herbal medicine throughout the world. Although various activities of H. perforatum extracts have been reported such as antibacterial, antiviral, wound healing, antioxidant, antimicrobial, anti-inflammatory, antinociceptive, antitumor, antiangiogenic, and immunomodulatory activity [1][2][3][4][5][6][7][8][9][10][11], the focus of interest is on its potential as an herbal antidepressant [2]. Flora Croatica Database (FCD) [12] describes two subspecies of H. perforatum in Croatia: ssp.…”

Chemical Composition and Antioxidant Activity of Essential Oils from Eugenia patrisii Vahl, E. punicifolia (Kunth) DC., and Myrcia tomentosa (Aubl.) DC., Leaf of Family Myrtaceae

“…Germacrene D has been described in the literature as having antimicrobial properties [26]. Besides, both germacrene D and (E)-caryophyllene have immunomod-ulatory activity in human neutrophils, inhibiting Ca 2+ mobilization, chemotaxis, and production of reactive oxygen species (ROS) [27]. This sesquiterpene constituent also has antioxidant and cytotoxic activity against melanoma cancer cells, which are responsible for skin cancer, breast adenocarcinoma, and colon carcinoma [28].…”