Pharmacokinetic properties of phytochemicals in Hypericum perforatum influence efficacy of regulating oxidative stress

Wise, Kimber; Selby-Pham, Sophie; Bennett, Louise; Selby‐Pham, Jamie

doi:10.1016/j.phymed.2018.11.023

Cited by 10 publications

(7 citation statements)

References 59 publications

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“…Hypericum L. (Hypericaceae) is comprised of approximately 500 species that can be found around the world. Various products from Hypericum species have been used as antidepressant, sedative, diuretic, antiphlogistic, analgesic, astringent, and antipyretic remedies in Europe, America, Africa, and Asia [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 ]. One of the most intensively studied medicinal plants from this genus is H. perforatum L. or St. John’s wort, which is a perennial herb that his known for its beneficial pharmacological properties [ 2 , 3 ].…”

Section: Introductionmentioning

confidence: 99%

“…Extracts from this herb have also been reported as a therapeutic remedy for burns, skin wounds, cuts, stomach aches, and ulcers [ 5 ]. In addition, H. perforatum extracts have also been reported to have anti-angiogenic, anti-fibroblastic, and antioxidant properties [ 6 , 7 , 8 ]. The phytochemical profile of H. perforatum includes naphthodianthrones (specifically hypericin and pseudohypericin), hyperforin, proanthocyanins, flavonoids, biflavonoids, xanthones, phenylpropanes, phenolic acids, and volatile constituents [ 9 , 10 , 11 ].…”

Section: Introductionmentioning

confidence: 99%

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Chemical Composition and Immunomodulatory Activity of Hypericum perforatum Essential Oils

Schepetkin

Özek

et al. 2020

Biomolecules

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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.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Chemical Composition and Immunomodulatory Activity of Hypericum perforatum Essential Oils

Schepetkin

Özek

et al. 2020

Biomolecules

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“…Even though the large amount of species in the genus Hypericum, the phytochemical and pharmacological activities of H. perforatum, commonly known as St. John's Wort, have been the most studied. Currently, the efficacy of H. perforatum in the treatment of slight or modest depression has been validated, so that in Germany, H. perforatum is used as a substitute for conventional antidepressant drugs such as Prozac [10]. Even so, the biological properties of H. perforatum have been attributed to numerous bioactive compounds belonging to the classes of flavonoids and phenolic acids.…”

Section: Introductionmentioning

confidence: 99%

Enzyme and Biological Activities of the Water Extracts from the Plants Aesculus hippocastanum, Olea europaea and Hypericum perforatum That Are Used as Folk Remedies in Turkey

et al. 2020

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Phenolic compounds are secondary metabolites that are found ubiquitously in plants, fruits, and vegetables. Many studies have shown that regular consumption of these compounds could have a positive effect on our health. The aim of this study was to compare the phytochemical contents of the water extracts from three different plants used as folk remedies in Turkey: Aesculus hippocastanum, Olea europaea, and Hypericum perforatum. A liquid chromatography-electrospray tandem mass spectrometry (LC-ESI-MS/MS) analysis was performed to explore the phenolic profiles. The biological activities of these extracts were also evaluated in terms of their antioxidant activities (2,2-diphenyl-1-picrylhydrazyl DPPH, 2,2′-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid ABTS, Ferric Reducing Antioxidant Power Assay FRAP, cupric ion reducing antioxidant capacity CUPRAC, β-carotene, phosphomolybdenum, and metal chelating) and enzyme inhibitory properties (against acetylcholinesterase, butyrylcholinesterase, and tyrosinase). The aqueous extract of H. perforatum showed the highest levels of total phenolic, flavonoid, and saponin contents. Protocatechuic acid, vanillic acid, verbascoside, hesperidin, hyperoside, apigenin 7-hexosides, and quercetin were the most common compounds found in this species. The results confirm that A. hippocastanum, O. europaea, and H. perforatum represent a potential source of natural-derived molecules with positive properties that could be used as valid starting point for new food supplements, and drugs in the pharmaceutical, cosmetic, and food industries.

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“…The T max for THC and CBD were observed as 0.05 h and 0.11 h, respectively, 40,41 while the predicted T max were 0.02 h and 0.03 h, respectively. Considering that T max predictions within 1.5 h of observation are considered to be accurate predictions, 15 these differences (average 4 min) were considered to be within the acceptable range of pharmacokinetic predictions. The IAP model was further applied to THC, CBD and the metabolites THC-COOH and 11-OH-THC to compare predicted T ½ ( Figure 2C) against in-vivo data ( Figure 2B) presented in Nadulski et al 42 Considering that the compounds in Nadulski et al 42 were ingested (not inhaled), only comparisons between their elimination half-lives (T ½ ) were made, as T ½ is only dependent on the compound not its method of intake.…”

Section: Application Of the Iap Model To Predict Phytochemical Decay mentioning

confidence: 99%

“…and Hypericum perforatum were recommended to be ingested two hours prior to meals to achieve maximal stress mediation from absorbed antioxidant phytochemicals by biomatching the time of maximal plasma concentration (T max ) with the period of postprandial oxidative stress. 15,16 Accordingly, the capacity to predict T max has allowed determination of optimal intake times to biomatch chemical activities with the timings of their maximal benefit.…”

Section: Introductionmentioning

confidence: 99%

Inhalation Absorption Prediction (IAP) Model for Predicting Medicinal Cannabis Phytochemical Pharmacokinetics

Wise¹,

Gill²,

Selby‐Pham³

2019

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Introduction: The medicinal benefits from inhalation of Cannabis sativa phytochemicals have been extensively reported. Whilst in-silico models are available for prediction of phytochemical pharmacokinetics post-ingestion, no models are available to accurately predict inhalation pharmacokinetics. Therefore, the aim of this study was to explore the relationship between phytochemical physicochemical properties and inhalation pharmacokinetics and to develop an in-silico model for predicting the time of maximal compound concentration in plasma (T max) and compound elimination half-life (T ½), following inhalation. Methods: A training set of compound pharmacokinetic data was collated from previous publications and compared to physicochemical parameters using regression analyses. Physicochemical parameters that correlated with T max and T ½ were combined to develop a statistical model, which constructs functional fingerprints predicting compound concentrations in plasma post inhalation. Predicted functional fingerprints for three cannabis bioactive compounds were constructed and biomatched against previously reported physiological effects. Results: Inhalation T max was predicted (r 2 = 0.84) by compound volume (Vol), topological surface area (TPSA) and molecular weight (MW), whilst T ½ was predicted (r 2 = 0.87) by molecular weight, volume and number of rotatable bonds (nrot). The resulting inhalation absorption prediction (IAP) model was achieved by combining T max and T ½ predictions. The IAP model was applied to cannabis metabolites which accurately predicted decay functions in-vivo and biomatching with associated physiological effects. Conclusion: The IAP model was applied successfully to cannabis phytochemicals to explore the pharmacokinetics underpinning their medicinal effects. This study demonstrates the utility of the IAP model and highlights its applicability during the investigation of medicinal plants and their modes of action.

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Pharmacokinetic properties of phytochemicals in Hypericum perforatum influence efficacy of regulating oxidative stress

Cited by 10 publications

References 59 publications

Chemical Composition and Immunomodulatory Activity of Hypericum perforatum Essential Oils

Chemical Composition and Immunomodulatory Activity of Hypericum perforatum Essential Oils

Enzyme and Biological Activities of the Water Extracts from the Plants Aesculus hippocastanum, Olea europaea and Hypericum perforatum That Are Used as Folk Remedies in Turkey

Inhalation Absorption Prediction (IAP) Model for Predicting Medicinal Cannabis Phytochemical Pharmacokinetics

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