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Norihisa Taira, Yushi Katsuyama, Masato Yoshioka, Osamu Muraoka, Toshio Morikawa
l-Ascorbic acid has multifunctional benefits on skin aesthetics, including inhibition of melanin production, and is widely used in cosmetics. It, however, has low stability and poor skin penetration. We hypothesize that alkylglyceryl-l-ascorbic acid derivatives, highly stable vitamin C-alkylglycerol conjugates, would have similar anti-melanogenic activity with better stability and penetration. We test 28 alkylglyceryl-l-ascorbic acid derivatives ( 1 - 28 ) on theophylline-stimulated B16 melanoma 4A5 cells to determine if they inhibit melanogenesis and establish any structure-function relationships...
April 10, 2018: International Journal of Molecular Sciences
Tristan de Rond, Parker Stow, Ian Eigl, Rebecca E Johnson, Leanne Jade G Chan, Garima Goyal, Edward E K Baidoo, Nathan J Hillson, Christopher J Petzold, Richmond Sarpong, Jay D Keasling
Prodiginines, which are tripyrrole alkaloids displaying a wide array of bioactivities, occur as linear and cyclic congeners. Identification of an unclustered biosynthetic gene led to the discovery of the enzyme responsible for catalyzing the regiospecific C-H activation and cyclization of prodigiosin to cycloprodigiosin in Pseudoalteromonas rubra. This enzyme is related to alkylglycerol monooxygenase and unrelated to RedG, the Rieske oxygenase that produces cyclized prodiginines in Streptomyces, implying convergent evolution...
November 2017: Nature Chemical Biology
Sandrine Marquet, Bruno Bucheton, Camille Reymond, Laurent Argiro, Sayda Hassan El-Safi, Musa Mohamed Kheir, Jean-Pierre Desvignes, Christophe Béroud, Adil Mergani, Awad Hammad, Alain J Dessein
Background: Visceral leishmaniasis (kala-azar, KA) is the most severe form of leishmaniasis, characterized by fever, weight loss, hepatosplenomegaly, and lymphadenopathy. During an outbreak of KA in Babar El Fugara (Sudan), 5.7% of cured patients displayed relapses, with familial clustering in half the cases. Methods: We performed whole-exome sequencing on 10 relapsing individuals and 11 controls from 5 nuclear families. Results: Rare homozygous and compound-heterozygous nonsense (c...
July 1, 2017: Journal of Infectious Diseases
Syed F Hassnain Waqas, Anh Cuong Hoang, Ya-Tin Lin, Grace Ampem, Hind Azegrouz, Lajos Balogh, Julianna Thuróczy, Jin-Chung Chen, Ivan C Gerling, Sorim Nam, Jong-Seok Lim, Juncal Martinez-Ibañez, José T Real, Stephan Paschke, Raphaëlle Quillet, Safia Ayachi, Frédéric Simonin, E Marion Schneider, Jacqueline A Brinkman, Dudley W Lamming, Christine M Seroogy, Tamás Röszer
The quantity and activation state of adipose tissue macrophages (ATMs) impact the development of obesity-induced metabolic diseases. Appetite-controlling hormones play key roles in obesity; however, our understanding of their effects on ATMs is limited. Here, we have shown that human and mouse ATMs express NPFFR2, a receptor for the appetite-reducing neuropeptide FF (NPFF), and that NPFFR2 expression is upregulated by IL-4, an M2-polarizing cytokine. Plasma levels of NPFF decreased in obese patients and high-fat diet-fed mice and increased following caloric restriction...
June 30, 2017: Journal of Clinical Investigation
Akiko Ohashi, Kaori Mamada, Tomonori Harada, Masako Naito, Tomihisa Takahashi, Shin Aizawa, Hiroyuki Hasegawa
Tetrahydrobiopterin (BH4 ) is a common coenzyme of phenylalanine-, tyrosine-, and tryptophan hydroxylases, alkylglycerol monooxygenase, and NO synthases (NOS). Synthetic BH4 is used medicinally for BH4 -responsive phenylketonuria and inherited BH4 deficiency. BH4 supplementation has also drawn attention as a therapy for various NOS-related cardio-vascular diseases, but its use has met with limited success in decreasing BH2 , the oxidized form of BH4 . An increase in the BH2 /BH4 ratio leads to NOS dysfunction...
November 2017: Molecular and Cellular Biochemistry
Sergio Alberto Bernal-Chávez, Lilia Yazmín Pérez-Carreto, María Guadalupe Nava-Arzaluz, Adriana Ganem-Rondero
The absorption modulating activity of two alkylglycerol derivatives (batyl and chimyl alcohol) on skin barrier properties was evaluated. Biophysical tests such as transepidermal water loss (TEWL) and attenuated total reflectance-Fourier transform infrared (ATR-FTIR) spectroscopy, as well as in vitro skin permeation studies, were performed in order to determine the effect of these compounds as chemical absorption modulators. Four drugs were used as models: three NSAIDS (diclofenac, naproxen, and piroxicam) and glycyrrhizic acid...
January 22, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Azam Moradi, Gholam Hosein Ebrahimipour, Kathrin I Mohr, Peter Kämpfer, Stefanie P Glaeser, Fabienne Hennessen, Katja Gemperlein, Ram Prasad Awal, Corinna Wolf, Rolf Müller, Joachim Wink
A novel myxobacterium, strain MSr11462T, was isolated in 2015 from a soil sample collected form Kish Island beach, Persian Gulf, Iran. It displayed general myxobacterial features like Gram-negative staining, rod-shaped vegetative cells, gliding on solid surfaces, microbial lytic activity, fruiting-body-like aggregates and myxospore-like structures. The strain was mesophilic, aerobic and showed a chemoheterotrophic mode of nutrition. It was resistant to many antibiotics like gentamycin, polymyxin, fusidic acid and trimethoprim, and the key fatty acids of whole-cell hydrolysates were iso-C15 : 0, C16 : 0, iso-C17 : 0, C18 : 1, iso-C17 : 1 2-OH, C18 : 1 2-OH, iso-C15 : 0 OAG (O-alkylglycerol) and C16 : 1 OAG...
February 2017: International Journal of Systematic and Evolutionary Microbiology
Lorenza González-Mariscal, Yanahi Posadas, Jael Miranda, Perla Yaceli Uc, José Mario Ortega-Olvera, Sandra Hernández
Ions and molecules move across epithelial barriers by two pathways, the transcellular and the paracellular. The former is taken by lipophilic compounds, or by ions and molecules that move across the plasma membrane through pumps, carriers or exchangers. The second route is regulated by the tight junction (TJ) that through paracellular channels, allows the transport of ions across epithelial barriers. Since, a wide variety of bioactive molecules like peptides, proteins and oligonucleotides cannot use the transcellular route, due to their hydrophilic nature, interest has arisen in devising procedures to open the TJ in a reversible manner for paracellular drug delivery...
2016: Current Pharmaceutical Design
A Parri, Montserrat Fitó, C F Torres, D Muñoz-Aguayo, H Schröder, J F Cano, L Vázquez, G Reglero, María-Isabel Covas
Alkylglycerols (AKGs), isolated or present in shark liver oil have anti-inflammatory properties. Complement 3 (C3) and 4 (C4) participate in lipid metabolism and in obesity, contributing to the metabolic syndrome and to the low-grade inflammation associated with obesity. In a randomized, controlled, crossover study, 26 non-diabetes obese individuals were assigned two preparations with low (LAC, 10 mg AKGs) and high (HAC, 20 mg AKGs) AKG content. Intervention periods were of 3 weeks preceded by 2-week washout periods in which shark liver oil was avoided...
June 2016: Inflammopharmacology
Nuha Alrayes, Hussein Sheikh Ali Mohamoud, Saleem Ahmed, Mona Mohammad Almramhi, Taghreed Mohammad Shuaib, Jun Wang, Jumana Yousuf Al-Aama, Kate Everett, Jamal Nasir, Musharraf Jelani
Autosomal recessive primary microcephaly (MCPH) refers to a genetically heterogeneous group of neurodevelopmental disorders in which patients exhibit a marked decrease in occipitofrontal head circumference at birth and a variable degree of intellectual disability. To date, 18 genes have been reported for MCPH worldwide. We enrolled a consanguineous family from Saudi Arabia presenting with primary microcephaly, developmental delay, short stature and intellectual disability. Whole exome sequencing (WES) with 100× coverage was performed on two affected siblings after defining common regions of homozygosity through genome-wide single nucleotide polymorphism (SNP) microarray genotyping...
April 15, 2016: Journal of the Neurological Sciences
Katja Zschiebsch, Caroline Fischer, Geethanjali Pickert, Annett Häussler, Heinfried Radeke, Sabine Grösch, Nerea Ferreirós, Gerd Geisslinger, Ernst R Werner, Irmgard Tegeder
BACKGROUND AND AIMS: Guanosine triphosphate cyclohydrolase [GCH1] governs the production of the enzyme cofactor tetrahydrobiopterin [BH4] which is essential for biogenic amine synthesis, lipid metabolism via alkylglycerol monooxygenase [AGMO], and redox coupling of nitric oxide synthases [NOSs]. Inflammation-evoked unequal regulation of GCH1 and NOS or AGMO may cause redox stress and lipid imbalances. METHODS: The present study assessed potential therapeutic effects of rebalancing these systems with BH4 in experimental colitis in mice...
August 2016: Journal of Crohn's & Colitis
Germaine Korner, Tanja Scherer, Dea Adamsen, Alexander Rebuffat, Mark Crabtree, Anahita Rassi, Rossana Scavelli, Daigo Homma, Birgit Ledermann, Daniel Konrad, Hiroshi Ichinose, Christian Wolfrum, Marion Horsch, Birgit Rathkolb, Martin Klingenspor, Johannes Beckers, Eckhard Wolf, Valérie Gailus-Durner, Helmut Fuchs, Martin Hrabě de Angelis, Nenad Blau, Jan Rozman, Beat Thöny
Tetrahydrobiopterin (BH4) is an essential cofactor for the aromatic amino acid hydroxylases, alkylglycerol monooxygenase, and nitric oxide synthases (NOS). Inborn errors of BH4 metabolism lead to severe insufficiency of brain monoamine neurotransmitters while augmentation of BH4 by supplementation or stimulation of its biosynthesis is thought to ameliorate endothelial NOS (eNOS) dysfunction, to protect from (cardio-) vascular disease and/or prevent obesity and development of the metabolic syndrome. We have previously reported that homozygous knock-out mice for the 6-pyruvolytetrahydropterin synthase (PTPS; Pts-ko/ko) mice with no BH4 biosynthesis die after birth...
March 2016: Journal of Inherited Metabolic Disease
Tilman Ahrendt, Christina Dauth, Helge B Bode
The E-signal is one of five intercellular signals (named A- to E-signal) guiding fruiting body development in Myxococcus xanthus, and it has been shown to be a combination of the branched-chain fatty acid (FA) iso-15 : 0 and the diacylmonoalkyl ether lipid TG1. Developmental mutants HB015 (Δbkd MXAN_4265::kan) and elbD (MXAN_1528::kan) are blocked at different stages of fruiting body and spore formation as they cannot form the required iso-FA or the actual ether lipid, respectively. In order to define the structural basis of the E-signal, different mono- and triglycerides containing ether or ester bonds were synthesized and used for complementation of these mutants...
January 2016: Microbiology
Petr Toman, Chun-Fu Lien, Zeeshan Ahmad, Susanne Dietrich, James R Smith, Qian An, Éva Molnár, Geoffrey J Pilkington, Darek C Górecki, John Tsibouklis, Eugen Barbu
Poly(lactic acid), which has an inherent tendency to form colloidal systems of low polydispersity, and alkylglyceryl-modified dextran - a material designed to combine the non-immunogenic and stabilising properties of dextran with the demonstrated permeation enhancing ability of alkylglycerols - have been combined for the development of nanoparticulate, blood-brain barrier-permeating, non-viral vectors. To this end, dextran, that had been functionalised via treatment with epoxide precursors of alkylglycerol, was covalently linked to poly(lactic acid) using a carbodiimide cross-linker to form alkylglyceryl-modified dextran-graft-poly(lactic acid)...
September 2015: Acta Biomaterialia
Curtis M Loer, Ana C Calvo, Katrin Watschinger, Gabriele Werner-Felmayer, Delia O'Rourke, Dave Stroud, Amy Tong, Jennifer R Gotenstein, Andrew D Chisholm, Jonathan Hodgkin, Ernst R Werner, Aurora Martinez
Tetrahydrobiopterin (BH4) is the natural cofactor of several enzymes widely distributed among eukaryotes, including aromatic amino acid hydroxylases (AAAHs), nitric oxide synthases (NOSs), and alkylglycerol monooxygenase (AGMO). We show here that the nematode Caenorhabditis elegans, which has three AAAH genes and one AGMO gene, contains BH4 and has genes that function in BH4 synthesis and regeneration. Knockout mutants for putative BH4 synthetic enzyme genes lack the predicted enzymatic activities, synthesize no BH4, and have indistinguishable behavioral and neurotransmitter phenotypes, including serotonin and dopamine deficiency...
May 2015: Genetics
Vincent Grossi, Damien Mollex, Arnauld Vinçon-Laugier, Florence Hakil, Muriel Pacton, Cristiana Cravo-Laureau
Bacterial glycerol ether lipids (alkylglycerols) have received increasing attention during the last decades, notably due to their potential role in cell resistance or adaptation to adverse environmental conditions. Major uncertainties remain, however, regarding the origin, biosynthesis, and modes of formation of these uncommon bacterial lipids. We report here the preponderance of monoalkyl- and dialkylglycerols (1-O-alkyl-, 2-O-alkyl-, and 1,2-O-dialkylglycerols) among the hydrolyzed lipids of the marine mesophilic sulfate-reducing proteobacterium Desulfatibacillum alkenivorans PF2803T grown on n-alkenes (pentadec-1-ene or hexadec-1-ene) as the sole carbon and energy source...
May 1, 2015: Applied and Environmental Microbiology
Katrin Watschinger, Markus A Keller, Eileen McNeill, Mohammad T Alam, Steven Lai, Sabrina Sailer, Veronika Rauch, Jyoti Patel, Albin Hermetter, Georg Golderer, Stephan Geley, Gabriele Werner-Felmayer, Robert S Plumb, Giuseppe Astarita, Markus Ralser, Keith M Channon, Ernst R Werner
Tetrahydrobiopterin is a cofactor synthesized from GTP with well-known roles in enzymatic nitric oxide synthesis and aromatic amino acid hydroxylation. It is used to treat mild forms of phenylketonuria. Less is known about the role of tetrahydrobiopterin in lipid metabolism, although it is essential for irreversible ether lipid cleavage by alkylglycerol monooxygenase. Here we found intracellular alkylglycerol monooxygenase activity to be an important regulator of alkylglycerol metabolism in intact murine RAW264...
February 24, 2015: Proceedings of the National Academy of Sciences of the United States of America
Emilie Caron, Jean-Luc Desseyn, Luce Sergent, Nana Bartke, Marie-Odile Husson, Alain Duhamel, Frédéric Gottrand
Pseudomonas aeruginosa is an opportunistic Gram-negative bacterium that causes pneumonia in immunocompromised humans and severe pulmonary damage in patients with cystic fibrosis. Imbalanced fatty acid incorporation in membranes, including increased arachidonic acid and decreased DHA concentrations, is known to play a critical role in chronic inflammation associated with bacterial infection. Other lipids, such as EPA and alkylglycerols, are also known to play a role in inflammation, particularly by stimulating the immune system, decreasing inflammation and inhibiting bacterial growth...
January 28, 2015: British Journal of Nutrition
Shaojun Yang, Yi-Hua Jan, Vladimir Mishin, Jason R Richardson, Muhammad M Hossain, Ned D Heindel, Diane E Heck, Debra L Laskin, Jeffrey D Laskin
Sepiapterin reductase (SPR) catalyzes the reduction of sepiapterin to dihydrobiopterin (BH2), the precursor for tetrahydrobiopterin (BH4), a cofactor critical for nitric oxide biosynthesis and alkylglycerol and aromatic amino acid metabolism. SPR also mediates chemical redox cycling, catalyzing one-electron reduction of redox-active chemicals, including quinones and bipyridinium herbicides (e.g., menadione, 9,10-phenanthrenequinone, and diquat); rapid reaction of the reduced radicals with molecular oxygen generates reactive oxygen species (ROS)...
March 2015: Journal of Pharmacology and Experimental Therapeutics
Beniamino Palmieri, Alfonso Pennelli, Alessandro Di Cerbo
BACKGROUND: Shark liver oil (SLO) contains both alkylglycerols (AKG) and squalene and is an ancient remedy among the fishermen on the west coast of Norway and Sweden. Literature reports showed that alkyglycerols enhance Fc-receptor mediated phagocytosis, increase humoral immune response and delay hypersensitivity reactions. METHODS: On this background we performed an open spontaneous study on 40 very old aged surgical patients preoperatively treated with alkyglycerols (500 mg twice a day for 4 weeks), in order to reduce the risks of operation, counteracting the postoperative inflammatory and anergic conditions thus achieving quick and plain recovery...
2014: Lipids in Health and Disease
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