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Hyperforin

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https://www.readbyqxmd.com/read/29751080/prenylated-%C3%AE-diketones-two-new-additions-to-the-family-of-biologically-active-hypericum-perforatum-l-hypericaceae-secondary-metabolites
#1
Niko S Radulović, Marija S Genčić, Nikola M Stojanović, Pavle J Randjelović, Nicolas Baldovini, Vanya Kurteva
Two novel β-diketones, 2,6,9-trimethyl-8-decene-3,5-dione (A) and 3,7,10-trimethyl-9-undecene-4,6-dione (B), were identified from the renowned medicinal plant Hypericum perforatum L. The structures of β-diketones A and B were corroborated by syntheses (4 steps starting from methyl acetoacetate, overall yields 30% and 23%, respectively). In solution, these β-diketones predominantly exist as two rapidly interconverting β-keto-enol tautomers. The structures of A and B show some common fragments with the molecules of hyperforin and adhyperforin, respectively, the acknowledged multi-target secondary metabolites from St...
May 8, 2018: Food and Chemical Toxicology
https://www.readbyqxmd.com/read/29732886/modular-total-syntheses-of-hyperforin-papuaforins-a-b-and-c-via-gold-i-catalyzed-carbocyclization
#2
Gabriel Bellavance, Louis Barriault
The remarkable biological activities of polyprenylated polycyclic acylphloroglucinols (PPAPs) combined with their highly oxygenated and densely functionalized frameworks have stimulated the interest of synthetic organic chemists over the last decade. Herein, we report the concise total syntheses of four natural products PPAPs of which some have antibacterial properties notably hyperforin and papuaforin A. The salient features of this strategy are the short and gram-scalable synthesis of densely substituted PPAPs scaffolds via a Au(I)-catalyzed carbocyclization and the late-stage functionalization for an unified access to a wide variety of PPAPs...
May 7, 2018: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/29621655/methodological-aspects-of-biologically-active-compounds-quantification-in-the-genus-hypericum
#3
Sławomir Dresler, Jozef Kováčik, Maciej Strzemski, Ireneusz Sowa, Magdalena Wójciak-Kosior
Accumulation of selected secondary metabolites in two Hypericum species (H. perforatum and H. annulatum) was compared in their vegetative parts (stems and leaves) and in terms of the extraction solvent (80% aq. methanol or 60% aq. ethanol). The presence of chlorogenic acid and quercitrin was not detected in stem of both species. Almost all metabolites were more accumulated in the leaves than in the stems (rutin, hyperoside, quercetin and hypericin) but epicatechin showed the opposite in both species and hyperforin in H...
June 5, 2018: Journal of Pharmaceutical and Biomedical Analysis
https://www.readbyqxmd.com/read/29599335/hyperforin-suppresses-tumor-growth-and-nf-%C3%AE%C2%BAb-mediated-anti-apoptotic-and-invasive-potential-of-non-small-cell-lung-cancer
#4
Wei-Ting Chen, Ying-Kai Chen, Song-Shei Lin, Fei-Ting Hsu
BACKGROUND/AIM: Previous studies have indicated that hyperforin inhibits tumor growth of hepatocellular carcinoma. However, the anticancer effects of hyperforin in non-small cell lung cancer (NSCLC) are ambiguous. The aim of the present study was to investigate the anticancer effect of hyperforin in NSCLC. NSCLC CL1-5-F4 cells were treated with different concentrations of hyperforin or NF-κB inhibitor (QNZ) for different time periods. MATERIALS AND METHODS: Change of cell viability, NF-κB activation, apoptotic signaling pathways, expression of anti-apoptotic proteins, and cell invasion were detected using the 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay, NF-κB reporter gene assay, flow cytometry, western blotting, and cell invasion assay...
April 2018: Anticancer Research
https://www.readbyqxmd.com/read/29568754/monoamine-oxidase-a-inhibition-and-associated-antioxidant-activity-in-plant-extracts-with-potential-antidepressant-actions
#5
Tomás Herraiz, Hugo Guillén
Monoamine oxidase (MAO) catalyzes the oxidative deamination of amines and neurotransmitters and is involved in mood disorders, depression, oxidative stress, and adverse pharmacological reactions. This work studies the inhibition of human MAO-A by Hypericum perforatum , Peganum harmala, and Lepidium meyenii, which are reported to improve and affect mood and mental conditions. Subsequently, the antioxidant activity associated with the inhibition of MAO is determined in plant extracts for the first time. H. perforatum inhibited human MAO-A, and extracts from flowers gave the highest inhibition (IC50 of 63...
2018: BioMed Research International
https://www.readbyqxmd.com/read/29499586/hyperforin-and-miquelianin-from-st-john-s-wort-attenuate-gene-expression-in-neuronal-cells-after-dexamethasone-induced-stress
#6
Sheela Verjee, Anna Weston, Christiane Kolb, Heba Kalbhenn-Aziz, Veronika Butterweck
Dysregulation of the hypothalamic-pituitary-adrenal (HPA) axis plays an important part in the development of depressive symptoms. In this study, the effects of a commercial St. John's wort extract (STW3-VI), hyperforin, miquelianin, and the selective serotonin reuptake inhibitor citalopram on the expression of genes relevant to HPA axis function were investigated in human neuronal cells. SH-SY5Y cells were treated with STW3-VI (20 µg/mL), hyperforin (1 µM), miquelianin (10 µM), or citalopram (10 µM) in the presence of the glucocorticoid receptor agonist dexamethasone (DEX,10 µM) for 6 h and 48 h, respectively...
March 2, 2018: Planta Medica
https://www.readbyqxmd.com/read/29499307/metabolomics-assisted-fingerprint-of-hypericum-perforatum-chemotypes-and-assessment-of-their-cytotoxic-activity
#7
Eirini Sarrou, Lefki-Pavlina Giassafaki, Domenico Masuero, Daniele Perenzoni, Ioannis S Vizirianakis, Maria Irakli, Paschalina Chatzopoulou, Stefan Martens
Hypericum perforatum is known as an important medicinal plant, used for the treatment of several diseases, while its pharmacological properties are attributed to the presence of a wide range of secondary metabolites. Due to the great chemotypic variability of Hypericum species in the nature, and the demand for standardized herbal products, a detailed phytochemical investigation was carried out on different parts (herba, leaf, flowers) from wild collected and cultivated populations, using advanced chromatographic tools...
April 2018: Food and Chemical Toxicology
https://www.readbyqxmd.com/read/29478534/activation-of-membrane-located-ca-2-channels-by-hop-beta-acids-and-their-tricyclic-transformation-products
#8
Carolin Schulz, Nikolas Fritz, Thomas Sommer, Karel Krofta, Kristina Friedland, Monika Pischetsrieder
Beta-bitter acids of hops (lupulones) revealed sedative and antidepressant-like effects in animal studies. Transformation of β-acids during beer brewing leads to the formation of tricyclic transformation products, which have a close structural analogy to hyperforin. The latter compound is responsible for the antidepressant activity of St. John's wort by activation of TRPC6 cation channels in neuronal-like cells leading to Ca2+ influx. In this study, nortricyclolupones, dehydrotricyclolupones, and tricyclolupones were isolated from a wort-boiling model and their structures were elucidated by UHPLC-DAD, UHPLC-ESI- -MS/MS and 1D/2D-NMR spectroscopy...
June 30, 2018: Food Chemistry
https://www.readbyqxmd.com/read/29461053/research-progress-of-polycyclic-polyprenylated-acylphloroglucinols
#9
Xing-Wei Yang, Robert B Grossman, Gang Xu
Polycyclic polyprenylated acylphloroglucinols (PPAPs) are a class of hybrid natural products sharing the mevalonate/methylerythritol phosphate and polyketide biosynthetic pathways and showing considerable structure and bioactivity diversity. This review discusses the progress of research into the chemistry and biological activity of 421 natural PPAPs in the past 11 years as well as in-depth studies of biological activities and total synthesis of some PPAPs isolated before 2006. We created an online database of all PPAPs known to date at http://www...
April 11, 2018: Chemical Reviews
https://www.readbyqxmd.com/read/29442047/comprehensive-phytochemical-characterization-of-st-john-s-wort-hypericum-perforatum-l-oil-macerates-obtained-by-different-extraction-protocols-via-analytical-tools-applicable-in-routine-control
#10
M Heinrich, R Daniels, F C Stintzing, D R Kammerer
The aim of the present study was to investigate the impact of crucial process parameters, i.e. of light and temperature conditions, during the preparation of St. John's wort (SJW, Hypericum perforatum L.) Arachis oil macerates. Extracts were prepared according to a standardized protocol over a period of 28 days. For this purpose, flowering tops of H. perforatum were macerated with Arachis oil (drug extract ratio, DERnative 1:4) under different light and temperature conditions. Spectrophotometric measurements were carried out to quantitate naphthodianthrones and to characterize extract color in the CIE L*C*h° system...
March 1, 2017: Die Pharmazie
https://www.readbyqxmd.com/read/29440179/role-of-c-jun-n-terminal-kinase-in-pregnane-x-receptor-mediated-induction-of-human-cytochrome-p4503a4-in-vitro
#11
Guncha Taneja, Chun Chu, Paramahamsa Maturu, Bhagavatula Moorthy, Romi Ghose
Cytochrome P450 CYP3A4 is the most abundant drug-metabolizing enzyme and is responsible for the metabolism of ∼50% of clinically available drugs. Induction of CYP3A4 impacts the disposition of its substrates and leads to harmful clinical consequences, such as failure of therapy. To prevent such undesirable consequences, the molecular mechanisms of regulation of CYP3A4 need to be fully understood. CYP3A4 induction is regulated primarily by the xenobiotic nuclear receptor pregnane-X receptor (PXR). After ligand binding, PXR is translocated to the nucleus, where it binds to the CYP3A4 promoter and induces its gene expression...
April 2018: Drug Metabolism and Disposition: the Biological Fate of Chemicals
https://www.readbyqxmd.com/read/29411879/understanding-drug-interactions-with-st-john-s-wort-hypericum-perforatum-l-impact-of-hyperforin-content
#12
REVIEW
Sigrun Chrubasik-Hausmann, Julia Vlachojannis, Andrew J McLachlan
OBJECTIVE: The aim of this study was to review herb-drug interaction studies with St John's wort (Hypericum perforatum L.) with a focus on the hyperforin content of the extracts used in these studies. METHODS: PUBMED was systematically searched to identify studies describing pharmacokinetic interactions involving St John's wort. Data on study design and the St John's wort extract or product were gathered to extract hyperforin content and daily dose used in interaction studies...
February 7, 2018: Journal of Pharmacy and Pharmacology
https://www.readbyqxmd.com/read/29382233/an-in-vivo-study-of-hypericum-perforatum-in-a-niosomal-topical-drug-delivery-system
#13
Mohamed Ali, Amira Abdel Motaal, Mohammed A Ahmed, Abdulrhman Alsayari, Omaima N El-Gazayerly
The active compounds present in Hypericum perforatum L. (Hypericaceae) include hyperforin, hypericins and flavonoids, which are assumed to be responsible for the activity of the extract in the treatment of wounds and scars. The present study aimed to incorporate H. perforatum extract standardized to a known content of phloroglucinols, naphthodianthrones and polyphenolic compounds into an effective transdermal drug delivery system capable of entrapping both lipophilic and hydrophilic constituents in the form of niosomal gels for wound treatment...
November 2018: Drug Delivery
https://www.readbyqxmd.com/read/29279803/wound-healing-potential-of-oil-of-hypercium-perforatum-in-excision-wounds-of-male-sprague-dawley-rats
#14
Shivananada B Nayak, Kubra Isik, Julien R Marshall
Objective: To evaluate the wound-healing activity of oil of Hypercium perforatum (St. John's wort), in excision wounds of male white rats. Approach: The current methods of wound management involve the use of antibiotic creams. The search for more natural materials for the purpose of healing of wounds has led to the discoveries of potential agents prepared from plant extracts. Hyperforin and Hypericin are important phytochemical constituents found in H. perforatum, which have been highlighted for their antimicrobial, antiviral, and anti-inflammatory properties in recent times...
December 1, 2017: Advances in Wound Care
https://www.readbyqxmd.com/read/29191717/improved-in-vitro-models-for-preclinical-drug-and-formulation-screening-focusing-on-2d-and-3d-skin-and-cornea-constructs
#15
REVIEW
Nicole Beißner, Antonio Bolea Albero, Jendrik Füller, Thomas Kellner, Lothar Lauterboeck, Jinghu Liang, Markus Böl, Birgit Glasmacher, Christel C Müller-Goymann, Stephan Reichl
The present overview deals with current approaches for the improvement of in vitro models for preclinical drug and formulation screening which were elaborated in a joint project at the Center of Pharmaceutical Engineering of the TU Braunschweig. Within this project a special focus was laid on the enhancement of skin and cornea models. For this reason, first, a computation-based approach for in silico modeling of dermal cell proliferation and differentiation was developed. The simulation should for example enhance the understanding of the performed 2D in vitro tests on the antiproliferative effect of hyperforin...
May 2018: European Journal of Pharmaceutics and Biopharmaceutics
https://www.readbyqxmd.com/read/29141922/trpc6-contributes-to-lps-induced-inflammation-through-erk1-2-and-p38-pathways-in-bronchial-epithelial-cells
#16
Li-Fen Zhou, Qing-Zi Chen, Chun-Tao Yang, Zhao-Di Fu, Shen-Ting Zhao, Yan Chen, Shu-Ni Li, Li Liao, Yu-Bo Zhou, Jian-Rong Huang, Jian-Hua Li
receptor potential canonical (TRPC) channels are presently an emerging target for airway disorders. Recent evidence has indicated that TRPC6 as a member of the TRPC family plays an important role in airway inflammation, but its precise function in bronchial epithelial cells remains unclear. The aim of this study was to investigate the role of TRPC6 in Toll-like receptor 4 (TLR4)-mediated inflammation in human bronchial epithelial cells stimulated by endotoxin [lipopolysaccharide (LPS)]. Hyp9 is a simplified phloroglucinol derivative of hyperforin that highly selectively activates TRPC6 channels...
March 1, 2018: American Journal of Physiology. Cell Physiology
https://www.readbyqxmd.com/read/28990659/persistence-of-stat-1-inhibition-and-induction-of-cytokine-resistance-in-pancreatic-%C3%AE-cells-treated-with-st-john-s-wort-and-its-component-hyperforin
#17
Michela Novelli, Pascale Beffy, Alex Gregorelli, Svetlana Porozov, Fabrizio Mascia, Chiara Vantaggiato, Pellegrino Masiello, Marta Menegazzi
OBJECTIVES: St John's wort extract (SJW) and its component hyperforin (HPF) were shown to potently inhibit cytokine-induced STAT-1 and NF-κB activation in pancreatic β cells and protect them against injury. This study aimed at exploring the time course of STAT-1 inhibition afforded by these natural compounds in the β-cell line INS-1E. METHODS: INS-1E cells were pre-incubated with SJW extract (2-5 μg/ml) or HPF (0.5-2 μm) and then exposed to a cytokine mixture...
October 9, 2017: Journal of Pharmacy and Pharmacology
https://www.readbyqxmd.com/read/28982580/stimulation-of-transient-receptor-potential-m3-trpm3-channels-increases-interleukin-8-gene-promoter-activity-involving-ap-1-and-extracellular-signal-regulated-protein-kinase
#18
Sandra Rubil, Andrea Lesch, Naofumi Mukaida, Gerald Thiel
Stimulation of Ca2+ permeable TRPM3 (transient receptor potential melastatin-3) channels with the steroid ligand pregnenolone sulfate activates stimulus-responsive transcription factors, including the transcription factor AP-1 (activator protein-1). As part of a search for AP-1-regulated target genes we analyzed the gene encoding interleukin-8 (IL-8) in HEK293 cells expressing TRPM3 channels. Here, we show that stimulation of TRPM3 channels activated transcription of an IL-8 promoter-controlled reporter gene that was embedded into the chromatin of the cells...
March 2018: Cytokine
https://www.readbyqxmd.com/read/28961505/hyperforin-attenuates-aluminum-induced-a%C3%AE-production-and-tau-phosphorylation-via-regulating-akt-gsk-3%C3%AE-signaling-pathway-in-pc12-cells
#19
Wanyue Huang, Ping Cheng, Kaiyuan Yu, Yanfei Han, Miao Song, Yanfei Li
Aluminum (Al) is a neurotoxicant and cause β-amyloid (Aβ) peptides aggregation and tau hyperphosphorylation. Hyperforin (HF) is one of the major active constituents of the extracts of St. John's Wort (Hypericum perforatum), can treat Alzheimer's disease (AD) and other diseases involving peptide accumulation and cognition impairment. To determine the effects of HF on Al-induced Aβ formation and tau hyperphosphorylation, PC12 cells were cultured and treated with Al-malt (500μM) and/or HF (1μM). The results showed that HF treatment significantly attenuated Al-malt-induced Aβ1-42 production by reducing the expressions of APP, BACE1 and PS1, while increasing the expressions of sAPPα, ADAM9/10/17, and tau phosphorylation in PC12 cells...
December 2017: Biomedicine & Pharmacotherapy, Biomédecine & Pharmacothérapie
https://www.readbyqxmd.com/read/28943862/the-chemical-and-antibacterial-evaluation-of-st-john-s-wort-oil-macerates-used-in-kosovar-traditional-medicine
#20
James T Lyles, Austin Kim, Kate Nelson, Angelle L Bullard-Roberts, Avni Hajdari, Behxhet Mustafa, Cassandra L Quave
Hypericum perforatum L. (Hypericaceae), or St. John's Wort, is a well-known medicinal herb often associated with the treatment of anxiety and depression. Additionally, an oil macerate (Oleum Hyperici) of its flowering aerial parts is widely used in traditional medicine across the Balkans as a topical wound and ulcer salve. Other studies have shown that Oleum Hyperici reduces both wound size and healing time. Of its active constituents, the naphthodianthrone hypericin and phloroglucinol hyperforin are effective antibacterial compounds against various Gram-positive bacteria...
2017: Frontiers in Microbiology
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