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Prenylation

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https://www.readbyqxmd.com/read/28729673/distinct-functional-relevance-of-dynamic-gtpase-cysteine-methylation-in-fission-yeast
#1
Alejandro Franco, Teresa Soto, Rebeca Martín-García, Marisa Madrid, Beatriz Vázquez-Marín, Jero Vicente-Soler, Pedro M Coll, Mariano Gacto, Pilar Pérez, José Cansado
The final step in post-translational processing of Ras and Rho GTPases involves methylation of the prenylated cysteine residue by an isoprenylcysteine-O-carboxyl methyltransferase (ICMT). ICMT activity is essential for cell growth and development in higher eukaryotes, and inhibition of GTPase methylation has become an attractive target in cancer therapy to inactivate prenylated oncoproteins. However, the specificity and dynamics of the GTPase methylation process remain to be fully clarified. Notably, cells lacking Mam4, the ICMT ortholog in the fission yeast Schizosaccharomyces pombe, are viable...
July 20, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28729053/bioactive-polyprenylated-benzophenone-derivatives-from-the-fruits-extracts-of-garcinia-xanthochymus
#2
Ui Joung Youn, Tawanun Sripisut, Gabriella Miklossy, James Turkson, Surat Laphookhieo, Leng Chee Chang
Two new polycyclic prenylated xanthones (1 and 2) and a new phenylpropanoid glycoside (3), along with seven known compounds (4-10) were isolated from the fruits of Garcinia xanthochymus. The structures were elucidated by 1D- and 2D-NMR, and HRMS experiments. The isolates were evaluated for their inhibitory effects against the viability of U251MG glioblastoma and MDA-MB-231 breast cancer cells that harbor an aberrantly active signal transducer and exhibit activation of transcription 3 (STAT3), and compared to normal NIH3T3 mouse fibroblasts...
July 1, 2017: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/28727177/total-synthesis-of-the-marine-natural-product-hemiasterlin-via-organocatalyzed-%C3%AE-hydrazination
#3
Thomas Lindel, Jan Hendrik Lang, Peter G Jones
An efficient synthesis of the potently cytotoxic marine peptide hemiasterlin is presented. The tetramethyltryptophan moiety is assembled via tert.-prenylation of indole, followed by the high-yielding, organocatalyzed α-hydrazination of a sterically congested aldehyde with excellent enantioselectivity. BEP-mediated peptide coupling completes the synthesis, being the first approach that does not employ chiral auxiliaries. A novel phenonium-type rearrangement of the indole system occurred when subjecting dihydroxylated 3-tert...
July 20, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/28723699/intraoperative-bleeding-in-patients-with-osteogenesis-imperfecta-type-iii-treated-by-fassier-duval-femoral-rodding-analysis-of-risk-factors
#4
Pietro Persiani, Maria V Pesce, Lorena Martini, Filippo M Ranaldi, Patrizia D'Eufemia, Anna Zambrano, Mauro Celli, Ciro Villani
The surgical treatment of osteogenesis imperfecta (OI) is negatively influenced by clinical features such as osteoporosis, limb deformities and bone changes caused by bisphosphonate therapy. Blood loss during femoral nailing surgeries in patients with OI is a serious problem. Platelet anomalies have been associated with an elevation of the serum pyrophosphate originating from the platelets during clotting, even if the causality with the platelet dysfunction has not yet been established. To identify predictive risk factors regarding intraoperative bleeding, a retrospective analysis was conducted on 23 patients aged between 6 and 13 years, affected by OI type III, who were treated to correct femoral deformities or to perform an osteosynthesis for femoral shaft fractures, using the Fassier-Duval telescopic nail...
July 18, 2017: Journal of Pediatric Orthopedics. Part B
https://www.readbyqxmd.com/read/28720813/a-new-prenylated-flavonoid-induces-g0-g1-arrest-and-apoptosis-through-p38-jnk-mapk-pathways-in-human-hepatocellular-carcinoma-cells
#5
Di Wang, Qian Sun, Jie Wu, Wei Wang, Guodong Yao, Tianyang Li, Xue Li, Lingzhi Li, Yan Zhang, Wei Cui, Shaojiang Song
Prenylated flavonoids have been demonstrated to possess diverse bioactivities including antitumor effects. One new, daphnegiravone D (1), and four known (2-5) prenylated flavonoids were isolated from Daphne giraldii. Their cytotoxic activities revealed that daphnegiravone D markedly inhibited the proliferation of cancer cells, but had no apparent cytotoxicity on human normal cells. Mechanistically, daphnegiravone D induced G0/G1 arrest and apoptosis, reduced the expression of cyclin E1, CDK2 and CDK4, and promoted the cleavage of caspase 3 and PARP in Hep3B and HepG2 cells...
July 18, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28716105/characterization-of-four-rice-uev1-genes-required-for-lys63-linked-polyubiquitination-and-distinct-functions
#6
Qian Wang, Yuepeng Zang, Xuan Zhou, Wei Xiao
BACKGROUND: The error-free branch of the DNA-damage tolerance (DDT) pathway is orchestrated by Lys63-linked polyubiquitination of proliferating cell nuclear antigen (PCNA), and this polyubiquitination is mediated by a Ubc13-Uev complex in yeast. We have previously cloned OsUBC13 from rice, whose product functions as an E2 to promote Lys63-linked ubiquitin chain assembly in the presence of yeast or human Uev. RESULTS: Here we identify four highly conserved UEV1 genes in rice whose products are able to form stable heterodimers with OsUbc13 and mediate Lys63-linked ubiquitin chain assembly...
July 17, 2017: BMC Plant Biology
https://www.readbyqxmd.com/read/28714338/antiplasmodial-prenylated-flavanonols-from-tephrosia-subtriflora
#7
Lois M Muiva-Mutisya, Yoseph Atilaw, Matthias Heydenreich, Andreas Koch, Hoseah M Akala, Agnes C Cheruiyot, Matthew L Brown, Beatrice Irungu, Faith A Okalebo, Solomon Derese, Charles Mutai, Abiy Yenesew
The CH2Cl2/MeOH (1:1) extract of the aerial parts of Tephrosia subtriflora afforded a new flavanonol, named subtriflavanonol (1), along with the known flavanone spinoflavanone B, and the known flavanonols MS-II (2) and mundulinol. The structures were elucidated by the use of NMR spectroscopy and mass spectrometry. The absolute configuration of the flavanonols was determined based on quantum chemical ECD calculations. In the antiplasmodial assay, compound 2 showed the highest activity against chloroquine-sensitive Plasmodium falciparum reference clones (D6 and 3D7), artemisinin-sensitive isolate (F32-TEM) as well as field isolate (KSM 009) with IC50 values 1...
July 16, 2017: Natural Product Research
https://www.readbyqxmd.com/read/28701884/cis-prenyltransferase-interacts-with-a-nogo-b-receptor-homolog-for-dolichol-biosynthesis-in-panax-ginseng-meyer
#8
Ngoc Quy Nguyen, Sang-Choon Lee, Tae-Jin Yang, Ok Ran Lee
BACKGROUND: Prenyltransferases catalyze the sequential addition of isopentenyl diphosphate units to allylic prenyl diphosphate acceptors and are classified as either trans-prenyltransferases (TPTs) or cis-prenyltransferases (CPTs). The functions of CPTs have been well characterized in bacteria, yeast, and mammals compared to plants. The characterization of CPTs also has been less studied than TPTs. In the present study, molecular cloning and functional characterization of a CPT from a medicinal plant, Panax ginseng Mayer were addressed...
July 2017: Journal of Ginseng Research
https://www.readbyqxmd.com/read/28699127/erratum-to-semisynthesis-and-biological-evaluation-of-prenylated-resveratrol-derivatives-as-multi-targeted-agents-for-alzheimer-s-disease
#9
Thanchanok Puksasook, Shinya Kimura, Sarin Tadtong, Jutamas Jiaranaikulwanitch, Jaturong Pratuangdejkul, Worawan Kitphati, Khanit Suwanborirux, Naoki Saito, Veena Nukoolkarn
No abstract text is available yet for this article.
July 11, 2017: Journal of Natural Medicines
https://www.readbyqxmd.com/read/28694184/engineering-yeasts-as-platform-organisms-for-cannabinoid-biosynthesis
#10
Bastian Zirpel, Friederike Degenhardt, Chantale Martin, Oliver Kayser, Felix Stehle
Δ(9)-tetrahydrocannabinolic acid (THCA) is a plant derived secondary natural product from the plant Cannabis sativa l. The discovery of the human endocannabinoid system in the late 1980s resulted in a growing number of known physiological functions of both synthetic and plant derived cannabinoids. Thus, manifold therapeutic indications of cannabinoids currently comprise a significant area of research. Here we reconstituted the final biosynthetic cannabinoid pathway in yeasts. The use of the soluble prenyltransferase NphB from Streptomyces sp...
July 7, 2017: Journal of Biotechnology
https://www.readbyqxmd.com/read/28682627/ribosomal-natural-products-tailored-to-fit
#11
Michael A Funk, Wilfred A van der Donk
Ribosomally synthesized and Post-translationally modified Peptides (RiPPs) take advantage of the ribosomal translation machinery to generate linear peptides that are subsequently modified with heterocycles and/or macrocycles to impose three-dimensional structure and thwart degradation by proteases. Although RiPP precursors are limited to proteinogenic amino acids, post-translational modifications (PTMs) can alter the structure of individual amino acids and thereby improve the stability and biological activity of the molecule...
July 6, 2017: Accounts of Chemical Research
https://www.readbyqxmd.com/read/28671568/antibacterial-activities-of-pyrenylated-coumarins-from-the-roots-of-prangos-hulusii
#12
Nur Tan, Seçil Yazıcı-Tütüniş, Merve Bilgin, Emir Tan, Mahmut Miski
The dichloromethane extract of the roots of Prangos hulusii, a recently described endemic species from Turkey, has yielded nine known and one new prenylated coumarins. The structures were elucidated by spectroscopic methods and direct comparison with the reference compounds where available. The root extract and its prenylated coumarins exhibit antimicrobial activity against nine standard and six clinically isolated strains at a concentration between 5 and 125 µg/mL. In particular, the new coumarin, 4'-senecioiloxyosthol (1), displayed 5 µg/mL MIC (Minimum Inhibitory Concentration) value against Bacillus subtilis ATCC 9372, murraol (4) and auraptenol (5) showed 63 µg/mL MIC value against Klebsiella pneumoniae ATCC 4352 and Bacillus subtilis ATCC 9372, and isoimperatorin (9) exhibited 16 µg/mL MIC value...
July 1, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28671289/mechanistic-characterization-of-two-chimeric-sesterterpene-synthases-from-penicillium
#13
Takaaki Mitsuhashi, Jan Rinkel, Masahiro Okada, Ikuro Abe, Jeroen S Dickschat
The products of two bifunctional fungal sesterterpene synthases (StTPS), with prenyl transferase (PT) and terpene synthase (TPS) domains from Penicillium, were structurally characterized and their mechanisms studied in detail by labeling experiments. A phylogenetic analysis of the TPS domains of the new and previously characterized enzymes revealed six distinct clades. Enzymes from the same clade catalyze a common initial cyclization step, which suggests the potential for structural predictions from amino acid sequences...
July 3, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/28669626/metabolism-and-antioxidant-effect-of-malaxinic-acid-and-its-corresponding-aglycone-in-rat-blood-plasma
#14
Hyun Joo Lee, Hang Yeon Jeong, Mi Rim Jin, Hyoung Jae Lee, Jeong-Yong Cho, Jae-Hak Moon
Malaxinic acid (MA) is a phenolic acid compound, found mainly in pear fruits (Pyrus pyrifolia N.), that is isoprenylated on the C-3 position of benzoic acid. Recently, the effects of prenylated phenolics on health have received much interest owing to their reported potent beneficial biological effects. We conducted a comparative study in rats to determine the metabolism, pharmacokinetics, and antioxidative activities of MA and its corresponding aglycone (MAA). MA and MAA were orally administered to rats (Sprague-Dawley, male, 6 weeks old) and their metabolites in plasma were analyzed...
June 29, 2017: Free Radical Biology & Medicine
https://www.readbyqxmd.com/read/28668359/the-balance-between-induction-and-inhibition-of-mevalonate-pathway-regulates-cancer-suppression-by-statins-a-review-of-molecular-mechanisms
#15
REVIEW
Yasin Ahmadi, Amir Ghorbanihaghjo, Hassan Argani
Statins are widely used drugs for their role in decreasing cholesterol in hypercholesterolemic patients. Statins through inhibition of Hydroxy Methyl Glutaryl-CoA Reductase (HMGCR), the main enzyme of the cholesterol biosynthesis pathway, inhibit mevalonate pathway that provides isoprenoids for prenylation of different proteins such as Ras superfamily which has an essential role in cancer developing. Inhibition of the mevalonate/isoprenoid pathway is the cause of the cholesterol independent effects of statins or pleotropic effects...
June 28, 2017: Chemico-biological Interactions
https://www.readbyqxmd.com/read/28666857/structure-activity-relationship-studies-on-thiaplidiaquinones-a-and-b-as-novel-inhibitors-of-plasmodium-falciparum-and-farnesyltransferase
#16
Melissa M Cadelis, Marie-Lise Bourguet-Kondracki, Joëlle Dubois, Marcel Kaiser, Jean Michel Brunel, David Barker, Brent R Copp
Marine meroterpenoids, thiaplidiaquinones A and B and their respective non-natural dioxothiazine regioisomers have been shown to inhibit mammalian and protozoal farnesyltransferase (FTase) with the regioisomers exhibiting activity in the nanomolar range. In order to explore the structure-activity relationship (SAR) of this class of marine natural products, analogues of thiaplidiaquinones A and B and their regioisomers were synthesised, with variation in the number of isoprene units present in their side chains to afford prenyl and farnesyl analogues...
June 19, 2017: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/28666798/insights-into-the-mevalonate-pathway-in-the-anticancer-effect-of-a-platinum-complex-on-human-gastric-cancer-cells
#17
Ling Qiu, Hui Yang, Gaochao Lv, Ke Li, Guiqing Liu, Wei Wang, Shanshan Wang, Xueyu Zhao, Minhao Xie, Jianguo Lin
A platinum(II) complex [Pt(en)]2ZL [en = ethylenediamine; ZL = 1-hydroxy-3(1H-imidazol-1-yl)ethane-1,1-diylbisphosphonic acid, commonly called as zoledronic acid] has been designed and synthesized recently in order to look for new anticancer drugs with high efficacy and low side effects. It exhibited cytotoxic effects on the human cancer cells SGC7901, HepG2, MCF-7, MDA-MB-231, HCT116, and U2OS, and the cytotoxicity against SGC7901 is particularly remarkable. It also showed higher cytotoxicity and better selectivity than the corresponding ligand ZL in inhibiting cancer cells SGC7901 and HepG2 rather than normal cells GES-1 and LO2...
June 27, 2017: European Journal of Pharmacology
https://www.readbyqxmd.com/read/28666734/a-novel-inhibitor-of-farnesyltransferase-with-a-zinc-site-recognition-moiety-and-a-farnesyl-group
#18
Ayumi Tanaka, Mohamed O Radwan, Akiyuki Hamasaki, Asumi Ejima, Emiko Obata, Ryoko Koga, Hiroshi Tateishi, Yoshinari Okamoto, Mikako Fujita, Mitsuyoshi Nakao, Kazuo Umezawa, Fuyuhiko Tamanoi, Masami Otsuka
Protein prenylation such as farnesylation and geranylgeranylation is associated with various diseases. Thus, many inhibitors of prenyltransferase have been developed. We report novel inhibitors of farnesyltransferase with a zinc-site recognition moiety and a farnesyl/dodecyl group. Molecular docking analysis showed that both parts of the inhibitor fit well into the catalytic domain of farnesyltransferase. The synthesized inhibitors showed activity against farnesyltransferase in vitro and inhibited proliferation of the pancreatic cell line AsPC-1...
June 20, 2017: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/28665345/in-vitro-effect-of-8-prenylnaringenin-and-naringenin-on-fibroblasts-and-glioblastoma-cells-cellular-accumulation-and-cytotoxicity
#19
Monika Stompor, Łukasz Uram, Rafał Podgórski
Gliomas are one of the most aggressive and treatment-resistant types of human brain cancer. Identification and evaluation of anticancer properties of compounds found in plants, such as naringenin (N) and 8-prenylnaringenin (8PN), are among the most promising applications in glioma therapy. The prenyl group seems to be crucial to the anticancer activity of flavones, since it may lead to enhanced cell membrane targeting and thus increased intracellular activity. It should be noted that 8PN content in hop cones is 10 to 100 times lower compared to other flavonoids, such as xanthohumol...
June 30, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28663238/remarkable-evolutionary-conservation-of-anti-obesity-adipose-wdtc1-homologs-in-animals-and-plants
#20
Eric Ducos, Valentin Vergès, Thomas Dugé de Bernonville, Nathalie Blanc, Nathalie Giglioli-Guivarc'h, Christelle Dutilleul
ASG2 (Altered Seed Germination 2) is a prenylated protein in Arabidopsis thaliana that participates to abscisic acid signaling and is proposed to act as a substrate adaptor for the DDB1-CUL4 E3 ubiquitin ligase complex. ASG2 harbors WD40 and TetratricoPeptide Repeat (TPR) domains, and resembles the well-conserved animal gene called ADP (anti-obesity factor ADIPOSE) in fly and WDTC1 (WD40 and TPR 1) in humans. Loss of function of WDTC1 results in an increase in adipocytes, fat accumulation and obesity. Anti-adipogenic functions of WDTC1 involve regulation of fat-related gene transcription, notably through its binding to histone deacetylases...
June 29, 2017: Genetics
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