TY  - JOUR
AB  - The contributions of de novo synthesis to terpene emissions from Eucalyptus globulus subsp. globulus were determined by fumigating branchlets with 13CO2 in a gas exchange system. Of more than thirty-four terpenes emitted by this species, only four, i.e., isoprene, iso-valeraldehyde, cis-ocimene, and trans-caryophyllene, incorporated 13C into the terpene carbon skeleton during the ~5-6 h experiment. 13C incorporation into isoprene and iso-valeraldehyde reached a maximum of ca. 82% of the carbon skeleton, similar to cis-ocimene, with a maximum of 77% 13C incorporation after ~2.5 h exposure to 13CO2. Only ca. 20% of carbon was labelled in trans-caryophyllene after 5-6 h. the incorporation of 13C was observed only in compounds emitted from leaves, and was not detected in either individual oil glands or in bulk leaf tissue. The results suggest the de novo synthesis of some terpenes (isoprene, cis-ocimene, trans-caryophyllene, and iso-valeraldehyde) and their emission is independent of emissions of terpenes stored in oil glands.
AU  - Winters, A.J.*
AU  - Hocart, C.H.*
AU  - Schnitzler, J.-P.
AU  - Zimmer, I.
AU  - Adams, M.A.*
AU  - Rennenberg, H.*
AU  - Kreuzwieser, J.*
AU  - Keitel, C.*
C1  - 74817
C2  - 57612
CY  - Mdpi Ag, Grosspeteranlage 5, Ch-4052 Basel, Switzerland
TI  - De novo terpenes emitted from juvenile leaves of Eucalyptus globulus Labill. subsp. globulus.
JO  - Molecules
VL  - 30
IS  - 10
PB  - Mdpi
PY  - 2025
SN  - 1420-3049
ER  - 

TY  - JOUR
AB  - In the original publication [...].
AU  - Miranda, A.S.*
AU  - Marcos, P.M.*
AU  - Ascenso, J.R.*
AU  - Berberan-Santos, M.N.*
AU  - Cardoso Micu Menezes, F.M.
C1  - 70551
C2  - 55669
CY  - St Alban-anlage 66, Ch-4052 Basel, Switzerland
TI  - Correction: Miranda et al. Anion Binding by Fluorescent Ureido-Hexahomotrioxacalix[3]arene Receptors: An NMR, Absorption and Emission Spectroscopic Study. Molecules 2022, 27, 3247.
JO  - Molecules
VL  - 29
IS  - 8
PB  - Mdpi
PY  - 2024
SN  - 1420-3049
ER  - 

TY  - JOUR
AB  - Neuroinflammation and oxidative stress are conditions leading to neurological and neuropsychiatric disorders. Natural compounds exerting anti-inflammatory and anti-oxidative effects, such as Licochalcone A, a bioactive flavonoid present in a traditional Chinese herb (licorice), might be beneficial for the treatment of those disorders. Therefore, this study aimed to investigate the anti-inflammatory and anti-oxidative effects of Licochalcone A in LPS-activated primary rat microglia. Licochalcone A dose-dependently prevented LPS-induced PGE2 release by inhibiting the arachidonic acid (AA)/cylcooxygenase (COX) pathway decreasing phospholipase A2, COX-1, and COX-2 protein levels. Furthermore, LPS-induced levels of the cytokines IL-6 and TNFα were reduced by Licochalcone A, which also inhibited the phosphorylation and, thus, activation of the mitogen-activated protein kinases (MAPK) p38 MAPK and Erk 1/2. With the reduction of 8-iso-PGF2α, a sensitive marker for oxidative stress, anti-oxidative effects of Licochalcone A were demonstrated. Our data demonstrate that Licochalcone A can affect microglial activation by interfering in important inflammatory pathways. These in vitro findings further demonstrate the potential value of Licochalcone A as a therapeutic option for the prevention of microglial dysfunction related to neuroinflammatory diseases. Future research should continue to investigate the effects of Licochalcone A in different disease models with a focus on its anti-oxidative and anti-neuroinflammatory properties.
AU  - Bhatia, H.S.
AU  - Apweiler, M.*
AU  - Sun, L.*
AU  - Baron, J.*
AU  - Tirkey, A.*
AU  - Fiebich, B.L.*
C1  - 67524
C2  - 54087
CY  - St Alban-anlage 66, Ch-4052 Basel, Switzerland
TI  - Licochalcone A inhibits prostaglandin E2 by targeting the MAPK pathway in LPS activated primary microglia.
JO  - Molecules
VL  - 28
IS  - 4
PB  - Mdpi
PY  - 2023
SN  - 1420-3049
ER  - 

TY  - JOUR
AB  - In this work, we study the buckycatcher (C60H28) in solution using quantum chemical models. We investigate the conformational equilibria in several media and the effects that molecules of solvent might have in interconversion barriers between the different conformers. These are studied in a hypothetical gas phase, in the dielectric of a solvent, as well as with hybrid solvation. In the latter case, due to a disruption of π-stacking interactions, the transition states are destabilized. We also evaluate the complexation of the buckycatcher with solvent-like molecules. In most cases studied, there should be no adducts formed because the enthalpy driving force cannot overcome entropic penalties.
AU  - Cardoso Micu Menezes, F.M.
AU  - Popowicz, G.M.
C1  - 67650
C2  - 53957
CY  - St Alban-anlage 66, Ch-4052 Basel, Switzerland
TI  - A buckycatcher in solution-a computational perspective.
JO  - Molecules
VL  - 28
IS  - 6
PB  - Mdpi
PY  - 2023
SN  - 1420-3049
ER  - 

TY  - JOUR
AB  - The corannulene pincer (also known in the literature as the buckycatcher) is a fascinating system that may encapsulate, among other molecules, the C60 and C70 fullerenes. These complexes are held together by strong π-stacking interactions. Although these are quantum mechanical effects, their description by quantum chemical methods has proved very hard. We used three semi-empirical methods, PM6-D3H4X, PM6-D3H+ and GFN2-xTB, to model the interactions. Binding to fullerenes was extended to all open conformations of the buckycatcher, and with the proper choice of solvation model and partition functions, we obtained Gibbs free energies of binding that deviated by 1.0-1.5 kcal/mol from the experimental data. Adding three-body dispersion to PM6-D3H+ led to even better agreement. These results agree better with the experimental data than calculations using higher-level methods at a significantly lower fraction of the computational cost. Furthermore, the formation of adducts with C60 was studied using dynamical simulations, which helped to build a more complete picture of the behavior of the corannulene pincer with fullerenes. We also investigated the use of exchange-binding models to recover more information on this system in solution. Though the final Gibbs free energies in solution were worsened, gas-phase enthalpies and entropies better mirrored the experimental data.
AU  - Cardoso Micu Menezes, F.M.
AU  - Popowicz, G.M.
C1  - 65526
C2  - 52717
TI  - How to catch the ball: Fullerene binding to the corannulene pincer.
JO  - Molecules
VL  - 27
IS  - 12
PY  - 2022
SN  - 1420-3049
ER  - 

TY  - JOUR
AB  - The current study examines the desiccation-resistant Ramlibacter tataouinensis TTB310T as a model organism for the production of novel exopolysaccharides and their structural features. This bacterium is able to produce dividing forms of cysts which synthesize cell-bound exopolysaccharide. Initial experiments were conducted on the enrichment of cyst biomass for exopolysaccharide production under batch-fed conditions in a pilot-scale bioreactor, with lactate as the source of carbon and energy. The optimized medium produced significant quantities of exopolysaccharide in a single growth phase, since the production of exopolysaccharide took place during the division of the cysts. The exopolysaccharide layer was extracted from the cysts using a modified trichloroacetic acid method. The biochemical characterization of purified exopolysaccharide was performed by gas chromatography, ultrahigh-resolution mass spectrometry, nuclear magnetic resonance, and Fourier-transform infrared spectrometry. The repeating unit of exopolysaccharide was a decasaccharide consisting of ribose, glucose, rhamnose, galactose, mannose, and glucuronic acid with the ratio 3:2:2:1:1:1, and additional substituents such as acetyl, succinyl, and methyl moieties were also observed as a part of the exopolysaccharide structure. This study contributes to a fundamental understanding of the novel structural features of exopolysaccharide from a dividing form of cysts, and, further, results can be used to study its rheological properties for various industrial applications.
AU  - Jivkova, D.*
AU  - Sathiyanarayanan, G.*
AU  - Harir, M.
AU  - Hertkorn, N.
AU  - Schmitt-Kopplin, P.
AU  - Sanhaji, G.*
AU  - Fochesato, S.*
AU  - Berthomieu, C.*
AU  - Heyraud, A.*
AU  - Achouak, W.*
AU  - Santaella, C.*
AU  - Heulin, T.*
C1  - 66678
C2  - 53267
TI  - Production and characterization of a novel exopolysaccharide from Ramlibacter tataouinensis.
JO  - Molecules
VL  - 27
IS  - 21
PY  - 2022
SN  - 1420-3049
ER  - 

TY  - JOUR
AB  - Fluorescent receptors (4a-4c) based on (thio)ureido-functionalized hexahomotrioxacalix[3]arenes were synthesised and obtained in the partial cone conformation in solution. Naphthyl or pyrenyl fluorogenic units were introduced at the lower rim of the calixarene skeleton via a butyl spacer. The binding of biologically and environmentally relevant anions was studied with NMR, UV-vis absorption, and fluorescence titrations. Fluorescence of the pyrenyl receptor 4c displays both monomer and excimer fluorescence. The thermodynamics of complexation was determined in acetonitrile and was entropy-driven. Computational studies were also performed to bring further insight into the binding process. The data showed that association constants increase with the anion basicity, and AcO-, BzO- and F- were the best bound anions for all receptors. Pyrenylurea 4c is a slightly better receptor than naphthylurea 4a, and both are more efficient than naphthyl thiourea 4b. In addition, ureas 4a and 4c were also tested as ditopic receptors in the recognition of alkylammonium salts.
AU  - Miranda, A.S.*
AU  - Marcos, P.M.*
AU  - Ascenso, J.R.*
AU  - Berberan-Santos, M.N.*
AU  - Cardoso Micu Menezes, F.M.
C1  - 65377
C2  - 52270
TI  - Anion binding by fluorescent ureido-hexahomotrioxacalix[3]arene receptors: An NMR, absorption and emission spectroscopic study.
JO  - Molecules
VL  - 27
IS  - 10
PY  - 2022
SN  - 1420-3049
ER  - 

TY  - JOUR
AB  - Background: Tart cherries (Prunus cerasus L.) are a rich source of anthocyanins. They are phytochemical flavonoids found in red and blue fruits, and vegetables that can reduce hyperlipidemia. Visceral Adipose Tissue (VAT) has emerged as a major player in driving obesity-related inflammatory response. Methods: This study has investigated the potential positive effects of tart cherries on rats with Diet-Induced Obesity (DIO). In particular, the inflammatory status in retroperitoneal (RPW) and perigonadal (PGW) adipose tissue were studied. Rats were fed ad libitum for 17 weeks with a hypercaloric diet with the supplementation of tart cherries seeds powder (DS) and seeds powder plus tart cherries juice containing 1mg of anthocyanins (DJS). In RPW and PGW, expression of CRP, IL-1 beta, TNF-alpha, CCL2 and CD36, were measured by qRT-PCR, Western blot and immunohistochemistry techniques. Results: No differences in the weight of RPW and PGW animals were found between DS and DJS groups compared to DIO rats. However, an increase of inflammatory markers was observed in DIO group in comparison with control lean rats. A modulation of these markers was evident upon tart cherry supplementation. Conclusion: Study results suggest that tart cherry enriched-diet did not modify the accumulation of visceral fat, but it decreased inflammatory markers in both tissues. Therefore, this supplementation could be useful, in combination with healthy lifestyles, to modify adipose tissue cell metabolism limiting-obesity related organ damage.
AU  - Moruzzi, M.*
AU  - Klöting, N.
AU  - Blüher, M.
AU  - Martinelli, I.*
AU  - Tayebati, S.K.*
AU  - Gabrielli, M.G.*
AU  - Roy, P.*
AU  - Micioni Di Bonaventura, M.V.*
AU  - Cifani, C.*
AU  - Lupidi, G.*
AU  - Amenta, F.*
AU  - Tomassoni, D.*
C1  - 61652
C2  - 50134
CY  - St Alban-anlage 66, Ch-4052 Basel, Switzerland
TI  - Tart cherry juice and seeds affect pro-inflammatory markers in visceral adipose tissue of high-fat diet obese rats.
JO  - Molecules
VL  - 26
IS  - 5
PB  - Mdpi
PY  - 2021
SN  - 1420-3049
ER  - 

TY  - JOUR
AB  - Background: Acute administration of the cannabinoid receptor 1 (CB1R) inverse agonist Rimonabant (SR141716A) to fed Wistar rats was shown to elicit a rapid and short-lasting elevation of serum free fatty acids.  Methods: The effect of Rimonabant on lipolysis in isolated primary rat adipocytes was studied to raise the possibility for direct mechanisms not involving the (hypothalamic) CB1R. (3) Results: Incubation of these cells with Rimonabant-stimulated lipolysis to up to 25% of the maximal isoproterenol effect, which was based on both CB1R-dependent and independent mechanisms. The CB1R-dependent one was already effective at Rimonabant concentrations of less than 1 mu M and after short-term incubation, partially additive to fi-adrenergic agonists and blocked by insulin and, in part, by adenosine deaminase, but not by propranolol. It was accompanied by protein kinase A (PKA)-mediated association of hormone-sensitive lipase (HSL) with lipid droplets (LD) and dissociation of perilipin-1 from LD. The CB1R-independent stimulation of lipolysis was observed only at Rimonabant concentrations above 1 mu M and after long-term incubation and was not affected by insulin. It was recapitulated by a cell-free system reconstituted with rat adipocyte LD and HSL. Rimonabant-induced cell-free lipolysis was not affected by PKA-mediated phosphorylation of LD and HSL, but abrogated by phospholipase digestion or emulsification of the LD. Furthermore, LD isolated from adipocytes and then treated with Rimonabant (>1 mu M) were more efficient substrates for exogenously added HSL compared to control LD. The CB1R-independent lipolysis was also demonstrated in primary adipocytes from fed rats which had been treated with a single dose of Rimonabant (30 mg/kg). (4) Conclusions: These data argue for interaction of Rimonabant (at high concentrations) with both the LD surface and the CB1R of primary rat adipocytes, each leading to increased access of HSL to LD in phosphorylation-independent and dependent fashion, respectively. Both mechanisms may lead to direct and acute stimulation of lipolysis at peripheral tissues upon Rimonabant administration and represent targets for future obesity therapy which do not encompass the hypothalamic CB1R.
AU  - Müller, G.
AU  - Herling, A.W.*
AU  - Wied, S.*
AU  - Müller, T.D.
C1  - 58362
C2  - 48171
CY  - St Alban-anlage 66, Ch-4052 Basel, Switzerland
TI  - CB1 receptor-dependent and independent induction of lipolysis in primary rat adipocytes by the inverse agonist rimonabant (SR141716A).
JO  - Molecules
VL  - 25
IS  - 4
PB  - Mdpi
PY  - 2020
SN  - 1420-3049
ER  - 

TY  - JOUR
AB  - Visceral adipose tissue derived serine protease inhibitor (vaspin) is a member of the serpin family and has been shown to have beneficial effects on glucose tolerance, insulin stability as well as adipose tissue inflammation, parameters seriously affected by obesity. Some of these effects require inhibition of target proteases such as kallikrein 7(KLK7) and many studies have demonstrated vaspin-mediated activation of intracellular signaling cascades in various cells and tissues. So far, little is known about the exact mechanism how vaspin may trigger these intracellular signaling events. In this study, we investigated and characterized the interaction of vaspin with membrane lipids and polyphosphates as well as their potential regulatory effects on serpin activity using recombinant vaspin and KLK7 proteins and functional protein variants thereof. Here, we show for the first time that vaspin binds to phospholipids and polyphosphates with varying effects on KLK7 inhibition. Vaspin binds strongly to monophosphorylated phosphatidylinositol phosphates (PtdInsP) with no effect on vaspin activation. Microscale thermophoresis (MST) measurements revealed high-affinity binding to polyphosphate 45 (K-D: 466 +/- 75 nM) and activation of vaspin in a heparin-like manner. Furthermore, we identified additional residues in the heparin binding site in fi-sheet A by mutating five basic residues resulting in complete loss of high-affinity heparin binding. Finally, using lipid overlay assays, we show that these residues are additionally involved in PtdInsP binding. Phospholipids play a major role in membrane trafficking and signaling whereas polyphosphates are procoagulant and proinflammatory agents. The identification of phospholipids and polyphosphates as binding partners of vaspin will contribute to the understanding of vaspins involvement in membrane trafficking, signaling and beneficial effects associated with obesity.
AU  - Tindall, C.A.*
AU  - Dommel, S.*
AU  - Riedl, V.*
AU  - Ulbricht, D.*
AU  - Hanke, S.*
AU  - Sträter, N.*
AU  - Heiker, J.T.
C1  - 58983
C2  - 48647
CY  - St Alban-anlage 66, Ch-4052 Basel, Switzerland
TI  - Membrane phospholipids and polyphosphates as cofactors and binding molecules of SERPINA12 (Vaspin).
JO  - Molecules
VL  - 25
IS  - 8
PB  - Mdpi
PY  - 2020
SN  - 1420-3049
ER  - 

TY  - JOUR
AB  - Hawthorn (Crataegus) is used for its cardiotonic, hypotensive, vasodilative, sedative, antiatherosclerotic, and antihyperlipidemic properties. One of the main goals of this work was to find a well-defined optimized extraction protocol usable by each of us that would lead to repeatable, controlled, and quantified daily uptake of active components from hawthorn at a drinkable temperature (below 60 degrees C). A thorough investigation of the extraction mode in water (infusion, maceration, percolation, ultrasounds, microwaves) on the yield of extraction and the amount of phenolic compounds, flavonoids, and proanthocyanidin oligomers as well as on the Ultra High Performance Liquid Chromatography (UHPLC) profiles of the extracted compounds was carried out. High-resolution Fourier transform ion cyclotron resonance mass spectrometry was also implemented to discriminate the different samples and conditions of extraction. The quantitative and qualitative aspects of the extraction as well as the kinetics of extraction were studied, not only according to the part (flowers or leaves), the state (fresh or dried), and the granulometry of the dry plant, but also the stirring speed, the temperature, the extraction time, the volume of the container (cup, mug or bowl) and the use of infusion bags.
AU  - Ngoc, P.C.*
AU  - Leclercq, L.*
AU  - Rossi, J.C.*
AU  - Desvignes, I.*
AU  - Hertzog, J.
AU  - Fabiano-Tixier, A.S.*
AU  - Chemat, F.*
AU  - Schmitt-Kopplin, P.
AU  - Cottet, H.*
C1  - 57598
C2  - 47839
CY  - St Alban-anlage 66, Ch-4052 Basel, Switzerland
TI  - Optimizing water-based extraction of bioactive principles of hawthorn: From experimental laboratory research to homemade preparations.
JO  - Molecules
VL  - 24
IS  - 23
PB  - Mdpi
PY  - 2019
SN  - 1420-3049
ER  - 

TY  - JOUR
AB  - Skin cancer is currently diagnosed as one in every three cancers. Melanoma, the most aggressive form of skin cancer, is responsible for 79% of skin cancer deaths and the incidence is rising faster than in any other solid tumor type. Previously, we have demonstrated that dimethylacrylshikonin (DMAS), isolated from the roots of Onosma paniculata (Boraginaceae), exhibited the lowest IC50 values against different tumor types out of several isolated shikonin derivatives. DMAS was especially cytotoxic towards melanoma cells and led to apoptosis and cell cycle arrest. In this study, we performed a comprehensive gene expression study to investigate the mechanism of action in more detail. Gene expression signature was compared to vehicle-treated WM164 control cells after 24 h of DMAS treatment; where 1192 distinct mRNAs could be identified as expressed in all replicates and 89 were at least 2-fold differentially expressed. DMAS favored catabolic processes and led in particular to p62 increase which is involved in cell growth, survival, and autophagy. More in-depth experiments revealed that DMAS led to autophagy, ROS generation, and loss of mitochondrial membrane potential in different melanoma cells. It has been reported that the induction of an autophagic cell death represents a highly effective approach in melanoma therapy.
AU  - Kretschmer, N.*
AU  - Deutsch, A.J.*
AU  - Durchschein, C.*
AU  - Rinner, B.*
AU  - Stallinger, A.*
AU  - Higareda-Almaraz, J.
AU  - Scheideler, M.
AU  - Lohberger, B.*
AU  - Bauer, R.*
C1  - 54679
C2  - 45758
CY  - St Alban-anlage 66, Ch-4052 Basel, Switzerland
TI  - Comparative gene expression analysis in WM164 melanoma cells revealed that beta-beta-Dimethylacrylshikonin leads to ROS generation, loss of mitochondrial membrane potential, and autophagy induction.
JO  - Molecules
VL  - 23
IS  - 11
PB  - Mdpi
PY  - 2018
SN  - 1420-3049
ER  - 

TY  - JOUR
AB  - The article describes a classification system termed "extended functional groups" (EFG), which are an extension of a set previously used by the CheckMol software, that covers in addition heterocyclic compound classes and periodic table groups. The functional groups are defined as SMARTS patterns and are available as part of the ToxAlerts tool (http://ochem.eu/alerts) of the On-line CHEmical database and Modeling (OCHEM) environment platform. The article describes the motivation and the main ideas behind this extension and demonstrates that EFG can be efficiently used to develop and interpret structure-activity relationship models.
AU  - Salmina, E.S.*
AU  - Haider, N.*
AU  - Tetko, I.V.
C1  - 47855
C2  - 39608
CY  - Basel
TI  - Extended Functional Groups (EFG): An efficient set for chemical characterization and structure-activity relationship studies of chemical compounds.
JO  - Molecules
VL  - 21
IS  - 1
PB  - Mdpi Ag
PY  - 2016
SN  - 1420-3049
ER  - 

TY  - JOUR
AB  - Chlorinated ethenes are prevalent groundwater contaminants. To better constrain (bio)chemical reaction mechanisms of reductive dechlorination, the position-specificity of reductive trichloroethene (TCE) dehalogenation was investigated. Selective biotransformation reactions (i) of tetrachloroethene (PCE) to TCE in cultures of Desulfitobacterium sp. strain Viet1; and (ii) of TCE to cis-1,2-dichloroethene (cis-DCE) in cultures of Geobacter lovleyi strain SZ were investigated. Compound-average carbon isotope effects were -19.0‰ ± 0.9‰ (PCE) and -12.2‰ ± 1.0‰ (TCE) (95% confidence intervals). Using instrumental advances in chlorine isotope analysis by continuous flow isotope ratio mass spectrometry, compound-average chorine isotope effects were measured for PCE (-5.0‰ ± 0.1‰) and TCE (-3.6‰ ± 0.2‰). In addition, position-specific kinetic chlorine isotope effects were determined from fits of reactant and product isotope ratios. In PCE biodegradation, primary chlorine isotope effects were substantially larger (by -16.3‰ ± 1.4‰ (standard error)) than secondary. In TCE biodegradation, in contrast, the product cis-DCE reflected an average isotope effect of -2.4‰ ± 0.3‰ and the product chloride an isotope effect of -6.5‰ ± 2.5‰, in the original positions of TCE from which the products were formed (95% confidence intervals). A greater difference would be expected for a position-specific reaction (chloride would exclusively reflect a primary isotope effect). These results therefore suggest that both vicinal chlorine substituents of TCE were reactive (intramolecular competition). This finding puts new constraints on mechanistic scenarios and favours either nucleophilic addition by Co(I) or single electron transfer as reductive dehalogenation mechanisms.
AU  - Cretnik, S.
AU  - Bernstein, A.
AU  - Shouakar-Stash, O.*
AU  - Löffler, F.E.*
AU  - Elsner, M.
C1  - 31374
C2  - 34488
CY  - Basel
SP  - 6450-6473
TI  - Chlorine isotope effects from isotope ratio mass spectrometry suggest intramolecular C-Cl bond competition in Trichloroethene (TCE) reductive dehalogenation.
JO  - Molecules
VL  - 19
IS  - 5
PB  - Mdpi Ag
PY  - 2014
SN  - 1420-3049
ER  -