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Prenylation

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https://www.readbyqxmd.com/read/29345110/remarkable-similarity-in-plasmodium-falciparum-and-plasmodium-vivax-geranylgeranyl-diphosphate-synthase-ggpps-dynamics-and-its-implication-for-anti-malarial-drug-design
#1
Aishwarya Venkatramani, Clarisse G Ricci, Eric Oldfield, J Andrew McCammon
Malaria, mainly caused by Plasmodium falciparum and Plasmodium vivax, has been a growing cause of morbidity and mortality. P. falciparum is more lethal than is P. vivax, but there is a vital need for effective drugs against both species. Geranylgeranyl diphosphate synthase (GGPPS) is an enzyme involved in the biosynthesis of quinones and in protein prenylation, and has been proposed to be a malaria drug target. However, the structure of P. falciparum GGPPS (PfGGPPS) has not been determined, due to difficulties in crystallization...
January 18, 2018: Chemical Biology & Drug Design
https://www.readbyqxmd.com/read/29342140/atomic-structure-of-the-eukaryotic-intramembrane-ras-methyltransferase-icmt
#2
Melinda M Diver, Leanne Pedi, Akiko Koide, Shohei Koide, Stephen B Long
The maturation of RAS GTPases and approximately 200 other cellular CAAX proteins involves three enzymatic steps: addition of a farnesyl or geranylgeranyl prenyl lipid to the cysteine (C) in the C-terminal CAAX motif, proteolytic cleavage of the AAX residues and methylation of the exposed prenylcysteine residue at its terminal carboxylate. This final step is catalysed by isoprenylcysteine carboxyl methyltransferase (ICMT), a eukaryote-specific integral membrane enzyme that resides in the endoplasmic reticulum...
January 17, 2018: Nature
https://www.readbyqxmd.com/read/29339971/terzyme-a-tool-for-identification-and-analysis-of-the-plant-terpenome
#3
Piyush Priya, Archana Yadav, Jyoti Chand, Gitanjali Yadav
Background: Terpenoid hydrocarbons represent the largest and most ancient group of phytochemicals, such that the entire chemical library of a plant is often referred to as its 'terpenome'. Besides having numerous pharmacological properties, terpenes contribute to the scent of the rose, the flavors of cinnamon and the yellow of sunflowers. Rapidly increasing -omics datasets provide an unprecedented opportunity for terpenome detection, paving the way for automated web resources dedicated to phytochemical predictions in genomic data...
2018: Plant Methods
https://www.readbyqxmd.com/read/29338226/prenylated-2-phenoxychromones-and-flavonoids-from-epimedium-brevicornum-and-revised-structures-of-epimedonins-a-and-b
#4
Fu-Cai Ren, Xian-Jun Jiang, Shi-Zhen Wen, Li-Xia Wang, Xiang-Mei Li, Fei Wang
Six hitherto unknown prenylated 2-phenoxychromones, epimedonin G (1), 7-O-methylepimedonin G (2), and epimedonins H-K (3-6), and two new prenylflavonoids, epimedonin L (7) and 3″-O-desmethylspinorhamnoside (8), were isolated from an ethanol extract of the aerial parts of Epimedium brevicornum. Their structures were established on the basis of spectroscopic data interpretation. Compound 7 exhibited cytotoxic activity when evaluated against four human cancer cell lines (HL-60, A-549, MCF-7, and SW-480), with IC50 values of <10 μM...
January 17, 2018: Journal of Natural Products
https://www.readbyqxmd.com/read/29331763/inhibition-of-isoprenylcysteine-carboxylmethyltransferase-sensitizes-common-chemotherapies-in-cervical-cancer-via-ras-dependent-pathway
#5
Qin Pan, Rong Liu, Hasina Banu, Liang Ma, Hui Li
Isoprenylcysteine carboxylmethyltransferase (Icmt) catalyzes the last step of post-translational protein prenylation, which is essential for the stability and proper functions of many oncogenic proteins, such as Ras. Despite extensive studies on the roles of Icmt in tumor transformation and progression, little is known on the involvement ofIcmt in the development of tumor resistance to chemotherapy. Here we show the upregulation of Icmt as a persistent response to chemotherapy in cervical cancer cells. In-depth functional analysis demonstrated that Icmt inhibition significantly inhibited growth, induced apoptosis and augmented the inhibitory effects of chemotherapy drugs in cervical cancer in cell culture system and xenograft mouse model...
January 10, 2018: Biomedicine & Pharmacotherapy, Biomédecine & Pharmacothérapie
https://www.readbyqxmd.com/read/29330372/non-estrogenic-xanthohumol-derivatives-mitigate-insulin-resistance-and-cognitive-impairment-in-high-fat-diet-induced-obese-mice
#6
Cristobal L Miranda, Lance A Johnson, Oriane de Montgolfier, Valerie D Elias, Lea S Ullrich, Joshua J Hay, Ines L Paraiso, Jaewoo Choi, Ralph L Reed, Johana S Revel, Chrissa Kioussi, Gerd Bobe, Urszula T Iwaniec, Russell T Turner, Benita S Katzenellenbogen, John A Katzenellenbogen, Paul R Blakemore, Adrian F Gombart, Claudia S Maier, Jacob Raber, Jan F Stevens
Xanthohumol (XN), a prenylated flavonoid from hops, improves dysfunctional glucose and lipid metabolism in animal models of metabolic syndrome (MetS). However, its metabolic transformation into the estrogenic metabolite, 8-prenylnaringenin (8-PN), poses a potential health concern for its use in humans. To address this concern, we evaluated two hydrogenated derivatives, α,β-dihydro-XN (DXN) and tetrahydro-XN (TXN), which showed negligible affinity for estrogen receptors α and β, and which cannot be metabolically converted into 8-PN...
January 12, 2018: Scientific Reports
https://www.readbyqxmd.com/read/29324340/antimalarial-naphthoquinones-synthesis-via-click-chemistry-in%C3%A2-vitro-activity-docking-to-pfdhodh-and-sar-of-lapachol-based-compounds
#7
Geraldo Célio Brandão, Franciele C Rocha Missias, Lucas Miquéias Arantes, Luciana Ferreira Soares, Kuldeep K Roy, Robert J Doerksen, Alaide Braga de Oliveira, Guilherme Rocha Pereira
Lapachol is an abundant prenyl naphthoquinone occurring in Brazilian Bignoniaceae that was clinically used, in former times, as an antimalarial drug, despite its moderate effect. Aiming to search for potentially better antimalarials, a series of 1,2,3-triazole derivatives was synthesized by chemical modification of lapachol. Alkylation of the hydroxyl group gave its propargyl ether which, via copper-catalyzed cycloaddition (CuAAC) click chemistry with different organic azides, afforded 17 naphthoquinonolyl triazole derivatives...
December 24, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/29322620/rice-protein-matrix-enhances-circulating-levels-of-xanthohumol-following-acute-oral-intake-of-spent-hops-in-humans
#8
Annalouise O'Connor, Veera Konda, Ralph L Reed, J Mark Christensen, Jan F Stevens, Nikhat Contractor
SCOPE: Xanthohumol (XN), a prenylated flavonoid found in hops, exhibits anti-inflammatory and antioxidant properties. However, poor bioavailability may limit therapeutic applications. As food components are known to modulate polyphenol absorption, the objective was to determine whether a protein matrix could enhance the bioavailability of XN post oral consumption in humans. METHODS AND RESULTS: This was a randomized, double-blind, cross-over study in healthy participants (n = 6) evaluating XN and its major metabolites [isoxanthohumol (IX), 6- and 8-prenylnaringenin (6-PN, 8-PN)] for 6 hours following consumption of 12...
January 11, 2018: Molecular Nutrition & Food Research
https://www.readbyqxmd.com/read/29317505/g%C3%AE-identity-dictates-efficacy-of-g%C3%AE-%C3%AE-signaling-and-macrophage-migration
#9
Kanishka Senarath, John L Payton, Dinesh Kankanamge, Praneeth Siripurapu, Mithila Tennakoon, Ajith Karunarathne
G protein βγ subunit (Gβγ) is a major signal transducer and controls processes ranging from cell migration to gene transcription. Despite having significant subtype heterogeneity and exhibiting diverse cell and tissue-specific expression levels, Gβγ is often considered a unified signaling entity with a defined functionality. However, the molecular and mechanistic basis of Gβγ's signaling specificity is unknown. Here, we demonstrate that Gγ subunits, bearing the sole plasma membrane (PM)-anchoring motif, control the PM affinity of Gβγ and thereby differentially modulate Gβγ effector signaling in a Gγ-specific manner...
January 9, 2018: Journal of Biological Chemistry
https://www.readbyqxmd.com/read/29311697/mechanistic-insights-into-the-role-of-prenyl-binding-protein-prbp-%C3%AE-in-membrane-dissociation-of-phosphodiesterase-6
#10
Bilal M Qureshi, Andrea Schmidt, Elmar Behrmann, Jörg Bürger, Thorsten Mielke, Christian M T Spahn, Martin Heck, Patrick Scheerer
Isoprenylated proteins are associated with membranes and their inter-compartmental distribution is regulated by solubilization factors, which incorporate lipid moieties in hydrophobic cavities and thereby facilitate free diffusion during trafficking. Here we report the crystal structure of a solubilization factor, the prenyl-binding protein (PrBP/δ), at 1.81 Å resolution in its ligand-free apo-form. Apo-PrBP/δ harbors a preshaped, deep hydrophobic cavity, capacitating apo-PrBP/δ to readily bind its prenylated cargo...
January 8, 2018: Nature Communications
https://www.readbyqxmd.com/read/29311475/evaluation-of-aculeatin-and-toddaculin-isolated-from-toddalia-asiatica-as-anti-inflammatory-agents-in-lps-stimulated-raw264-macrophages
#11
Momochika Kumagai, Akio Watanabe, Izumi Yoshida, Takashi Mishima, Munetomo Nakamura, Keisuke Nishikawa, Yoshiki Morimoto
Anti-inflammatory activity of aculeatin and toddaculin, which are coumarins with a similar structure isolated from Toddalia asiatica (L.) LAM., was evaluated using lipopolysaccharide (LPS)-stimulated RAW264 mouse macrophage cells. Both aculeatin and toddaculin significantly inhibited mRNA expression of inflammatory mediators and nitric oxide production. Furthermore, Toddaculin suppressed LPS-induced phosphorylation of p38 and extracellular signal-regulated kinase (ERK)1/2 and inhibited LPS-induced activation of nuclear factor-kappaB (NF-κB)...
2018: Biological & Pharmaceutical Bulletin
https://www.readbyqxmd.com/read/29305606/xanthohumol-protects-morphology-and-function-in-a-mouse-model-of-retinal-degeneration
#12
Nathaniel F Henneman, Stephanie L Foster, Micah A Chrenek, Jana T Sellers, Charles B Wright, Robin H Schmidt, John M Nickerson, Jeffrey H Boatright
Purpose: To investigate whether treatment with xanthohumol (XN), the principal prenylated chalconoid from Humulus lupulus (hops), is protective in a mouse model of light-induced retinal degeneration (LIRD). Methods: Mice (129S2/SvPasCrl) were intraperitoneally injected with vehicle or XN prior to toxic light exposure and every 3 days thereafter. Retinal function was assessed by electroretinograms at 1, 2, and 4 weeks following toxic light exposure. Visual acuity was tested by optokinetic tracking 1 week and 4 weeks after toxic light exposure...
January 1, 2018: Investigative Ophthalmology & Visual Science
https://www.readbyqxmd.com/read/29303577/anti-inflammatory-prenylated-phenylpropenols-and-coumarin-derivatives-from-murraya-exotica
#13
Bing-Yu Liu, Chen Zhang, Ke-Wu Zeng, Jun Li, Xiao-Yu Guo, Ming-Bo Zhao, Peng-Fei Tu, Yong Jiang
Three new prenylated phenylpropenols, exotiacetals A-C (1-3), 10 new coumarin derivatives, exotimarins A-I (4-13), and 35 known analogues (14-48) were isolated from the roots of Murraya exotica. The absolute configurations of the new compounds were assigned via comparison of their specific rotations, single-crystal X-ray diffraction data, Mosher's method, the ECD exciton coupling method, comparison of experimental and calculated ECD data, and the ECD data of the in situ formed transition metal complexes. Compounds 1-3, which possess an unprecedented hexahydro-1H-isochromen-1-ol system, are presumably biosynthesized from two prenylated p-coumaryl alcohol moieties via Diels-Alder [4+2] cycloaddition and cyclic hemiacetal formation reactions...
January 5, 2018: Journal of Natural Products
https://www.readbyqxmd.com/read/29303071/prenylated-coumarins-of-the-genus-citrus-an-overview-of-the-2006-2016-literature-data
#14
Salvatore Genovese, Vito Alessandro Taddeo, Francesco Epifano, Serena Fiorito
O-Prenyl coumarins (3,3-dimethylallyl, geranyl-, farnesyl- and related biosynthetic derivatives) represent a class of rarely occurring natural products. In the last two decades such secondary metabolites have been found to possess promising and effective pharmacological properties, mainly in terms of anti-cancer and anti-inflammatory properties. To date about 160 oxyprenylated coumarins have been extracted from plants, fungi, and bacteria. The genus Citrus have been demonstrated to be among the richest source of the title products...
January 4, 2018: Current Medicinal Chemistry
https://www.readbyqxmd.com/read/29300354/modulation-of-inducible-nitric-oxide-synthase-expression-in-lps-stimulated-bv-2-microglia-by-prenylated-chalcones-from-cullen-corylifolium-l-medik-through-inhibition-of-i-%C3%AE%C2%BAb%C3%AE-degradation
#15
Do Hee Kim, Hua Li, Yeong Eun Han, Ji Hye Jeong, Hwa Jin Lee, Jae-Ha Ryu
The overproduction of nitric oxide (NO) and prostaglandin E₂ (PGE₂) by microglia may cause neurodegenerative diseases, such as Alzheimer's disease and Parkinson's disease. From the activity-guided purification of Cullen corylifolium (L.) Medik. (syn. Psoralea corylifolia L.), three prenylated chalcones were identified: isobavachalcone (1), bavachromene (2), and kanzonol B (3). These prenylated chalcones showed concentration-dependent inhibitory effects on NO and PGE₂ production in lipopolysaccharide (LPS)-activated microglia...
January 4, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/29291443/prenylated-flavonoids-as-potent-phosphodiesterase-4-inhibitors-from-morus-alba-isolation-modification-and-structure-activity-relationship-study
#16
Yan-Qiong Guo, Gui-Hua Tang, Lan-Lan Lou, Wei Li, Bei Zhang, Bo Liu, Sheng Yin
The bioassay-guided phytochemical study of a traditional Chinese medicine Morus alba led to the isolation of 18 prenylated flavonoids (1-18), of which (±)-cyclomorusin (1/2), a pair of enantiomers, and 14-methoxy-dihydromorusin (3) are the new ones. Subsequent structural modification of the selected components by methylation, esterification, hydrogenation, and oxidative cyclization led to 14 more derivatives (19-32). The small library was screened for its inhibition against phosphodiesterase-4 (PDE4), which is a drug target for the treatment of asthma and chronic obstructive pulmonary disease (COPD)...
December 16, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/29290764/aminoacylase-3-is-a-new-potential-marker-and-therapeutic-target-in-hepatocellular-carcinoma
#17
Kirill Tsirulnikov, Sergio Duarte, Anamika Ray, Nakul Datta, Ali Zarrinpar, Lin Hwang, Kym Faull, Alexander Pushkin, Ira Kurtz
Ras proteins (HRas, KRas and NRas) are common oncogenes that require membrane association for activation. Previous approaches to block/inhibit Ras membrane association were unsuccessful for cancer treatment in human clinical studies. In the present study we utilized a new approach to decrease Ras membrane association in hepatocellular carcinoma (HCC) cell lines via inhibition of an enzyme aminoacylase 3 (AA3; EC 3.5.1.114). AA3 expression was significantly elevated in the livers of HCC patients and HCC cell lines...
2018: Journal of Cancer
https://www.readbyqxmd.com/read/29282289/efficient-farnesylation-of-an-extended-c-terminal-c-x-3x-sequence-motif-expands-the-scope-of-the-prenylated-proteome
#18
Melanie J Blanden, Kiall F Suazo, Emily R Hildebrandt, Daniel S Hardgrove, Meet Patel, William P Saunders, Mark D Distefano, Walter K Schmidt, James L Hougland
Protein prenylation is a post-translational modification that has been most commonly associated with enabling protein trafficking to and interaction with cellular membranes. In this process, an isoprenoid group is attached to a cysteine near the C-terminus of a substrate protein by protein farnesyltransferase (FTase) or protein geranylgeranyltransferase type I or II (GGTase-I and GGTase-II). FTase and GGTase-I have long been proposed to specifically recognize a four amino acid CaaX C-terminal sequence within their substrates...
December 27, 2017: Journal of Biological Chemistry
https://www.readbyqxmd.com/read/29281919/terretonin-m-a-new-meroterpenoid-from-the-thermophilic-aspergillus-terreus-tm8-and-revision-of-the-absolute-configuration-of-penisimplicins
#19
Mohamed Shaaban, Mohammad Magdy El-Metwally, Ahmed Adel Abdel-Razek, Hartmut Laatsch
Terretonin M (1), a new highly oxygenated tetracyclic meroterpenoid, was isolated from the thermophilic fungus Aspergillus terreus TM8 together with 10 known metabolites: terrelumamide A, asterrelenin, 7-prenyl-indolyl-3-carbaldehyde, (3β,5α,6β)-3,5,6-trihydroxy-ergosta-7,22-diene, sitostenone, linoleic acid, ergosterol, uracil, p-hydroxy-benzoic acid, and indole-3-carboxylic acid. The chemical structure of the new compound was elucidated by extensive 1D, 2D NMR, and ESI HR mass measurements, and by comparison with literature data...
December 27, 2017: Natural Product Research
https://www.readbyqxmd.com/read/29280630/phenanthrenes-a-promising-group-of-plant-secondary-metabolites
#20
Barbara Tóth, Judit Hohmann, Andrea Vasas
Although phenanthrenes are considered to constitute a relatively small group of natural products, discovering new phenanthrene derivatives and evaluating their prospective biological activities have become of great interest to many research groups worldwide. Based on 160 references, this review covers the phytochemistry and pharmacology of 213 naturally occurring phenanthrenes that have been isolated between 2008 and 2016. More than 40% of the 450 currently known naturally occurring phenanthrenes were identified during this period...
December 27, 2017: Journal of Natural Products
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