21956-55-8Relevant academic research and scientific papers
Two resveratrol analogs, pinosylvin and 4,4′-dihydroxystilbene, improve oligoasthenospermia in a mouse model by attenuating oxidative stress via the Nrf2-ARE pathway
Cheng, C. Yan,Gong, Sheng-nan,Sang, Meng-meng,Sun, Fei,Wang, Cheng-niu,Yang, Jin-fei
, (2020/10/02)
Two synthesized resveratrol analogs from our laboratory, namely pinosylvin (3,5-dihydroxy-trans-stilbene, PIN) and 4,4′-dihydroxystilbene (DHS), have been carefully evaluated for treatment of oligoasthenospermia. Recent studies have demonstrated that PIN and DHS improved sperm quality in the mouse. However, the mechanism of action of PIN and DHS on oligoasthenospermia remains unknown. Herein, we investigated the mechanistic basis for improvements in sperm parameters by PIN and DHS in a mouse model of oligoasthenospermia induced by treatment with busulfan (BUS) at 6 mg/kg b.w. Two weeks following busulfan treatment, mice were administered different concentrations of PIN or DHS daily for 2 consecutive weeks. Thereafter, epididymal sperm concentration and motility were determined, and histopathology of the testes was performed. Serum hormone levels including testosterone (T), luteinizing hormone (LH), and follicle stimulating hormone (FSH) were measured using corresponding specific enzyme-linked immunosorbent assay (ELISA) kits. Testicular mRNA expression profiles were determined by RNA sequencing analysis. These findings were validated by quantitative real-time PCR, western blotting and ELISA. Both PIN and DHS improved the epididymal sperm concentration and motility, enhanced testosterone levels, and promoted testicular morphological recovery following BUS treatment. PIN treatment was found to significantly reduce oxidative stress via the nuclear factor erythroid 2-related factor 2 (Nrf2)-antioxidant response element (ARE)-dependent antioxidant, glutathione peroxidase 3. DHS treatment significantly reduced oxidative stress via the Nrf2-ARE-dependent antioxidants glutathione S-transferase theta 2 and glutathione S-transferase omega 2. In summary, PIN and DHS ameliorated oligoasthenospermia in this mouse model by attenuating oxidative stress via the Nrf2-ARE pathway.
Novel resveratrol derivatives have diverse effects on the survival, proliferation and senescence of primary human fibroblasts
Birar, Vishal C.,Faragher, Richard G. A.,Ostler, Elizabeth L.,Sheerin, Angela N.
, p. 817 - 826 (2020/08/17)
Resveratrol alters the cytokinetics of mammalian cell populations in a dose dependent manner. Concentrations above 25–50 μM typically trigger growth arrest, senescence and/or apoptosis in multiple different cell types. In contrast, concentrations below 10 μM enhance the growth of log phase cell cultures and can rescue senescence in multiple strains of human fibroblasts. To better understand the structural features that regulate these effects, a panel of 24 structurally-related resveralogues were synthesised and evaluated for their capacity to activate SIRT1, as determined by an ex-vivo SIRT1 assay, their toxicity, as measured by lactate dehydrogenase release, and their effects on replicative senescence in MRC5 human fibroblasts as measured by their effects on Ki67 immunoreactivity and senescence-associated β galactosidase activity. Minor modifications to the parent stilbene, resveratrol, significantly alter the biological activities of the molecules. Replacement of the 3,5-dihydroxy substituents with 3,5-dimethoxy groups significantly enhances SIRT1 activity, and reduces toxicity. Minimising other strong conjugative effects also reduces toxicity, but negatively impacts SIRT1 activation. At 100 μM many of the compounds, including resveratrol, induce senescence in primary MRC5 cells in culture. Modifications that reduce or remove this effect match those that reduce toxicity leading to a correlation between reduction in labelling index and increase in LDH release. At 10 μM, the majority of our compounds significantly enhance the growth fraction of log phase cultures of MRC5 cells, consistent with the rescue of a subpopulation of cells within the culture from senescence. SIRT1 activation is not required for rescue to occur but enhances the size of the effect.
Ligand-controlled iridium-catalyzed semihydrogenation of alkynes with ethanol: highly stereoselective synthesis of E- and Z-alkenes
Yang., Jinfei,Wang, Chengniu,Sun, Yufeng,Man, Xuyan,Li, Jinxia,Sun, Fei
supporting information, p. 1903 - 1906 (2019/05/02)
A ligand-controlled iridium-catalyzed semihydrogenation of alkynes to E- and Z-alkenes with ethanol was developed. Effective selectivity control was achieved by ligand regulation. The use of 1,2-bis(diphenylphosphino)ethane (DPPE) and 1,5-cyclooctadiene (COD) was critical for the stereoselective semihydrogenation of alkynes. The general applicability of this procedure was highlighted by the synthesis of more than 40 alkenes, with good stereoselectivities. The value of our approach in practical applications was investigated by studying the effects of pinosylvin and 4,4′-dihydroxystilbene (DHS) on zebrafish as a vertebrate model.
Photoinitiated carbonyl-metathesis: Deoxygenative reductive olefination of aromatic aldehydes: Via photoredox catalysis
Wang, Shun,Lokesh, Nanjundappa,Hioe, Johnny,Gschwind, Ruth M.,K?nig, Burkhard
, p. 4580 - 4587 (2019/05/14)
Carbonyl-carbonyl olefination, known as McMurry reaction, represents a powerful strategy for the construction of olefins. However, catalytic variants that directly couple two carbonyl groups in a single reaction are less explored. Here, we report a photoredox-catalysis that uses B2pin2 as terminal reductant and oxygen trap allowing for deoxygenative olefination of aromatic aldehydes under mild conditions. This strategy provides access to a diverse range of symmetrical and unsymmetrical alkenes with moderate to high yield (up to 83%) and functional-group tolerance. To follow the reaction pathway, a series of experiments were conducted including radical inhibition, deuterium labelling, fluorescence quenching and cyclic voltammetry. Furthermore, NMR studies and DFT calculations were combined to detect and analyze three active intermediates: a cyclic three-membered anionic species, an α-oxyboryl carbanion and a 1,1-benzyldiboronate ester. Based on these results, we propose a mechanism for the CC bond generation involving a sequential radical borylation, "bora-Brook" rearrangement, B2pin2-mediated deoxygenation and a boron-Wittig process.
Method for synthesizing olefin compound by photo-induced one-pot process
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Paragraph 0121-0123, (2018/11/03)
The invention discloses a method for synthesizing an olefin compound by a photo-induced one-pot process. The method comprises the following step of subjecting a halohydrocarbon and an aldehyde compound to a reaction under the condition of irradiation in an inert atmosphere by taking alkali metal carbonate as a base, taking an organic phosphine compound as an adjuvant and taking a photosensitizer as a catalyst, thereby obtaining the olefin compound. According to the method disclosed by the invention, the olefin compound is produced from the halohydrocarbon and the aldehyde compound in a high-yield manner under the condition of irradiation in the inert atmosphere under normal-temperature reaction conditions by taking acetonitrile, DMF (N,N-dimethylformamide) or DMA (N,N-dimethylacetamide) asa solvent, taking an organic phosphine reagent as a reaction adjuvant, taking the alkali metal carbonate as the base and taking the photosensitizer as the catalyst. Compared with the conventional olefin synthesis methods, the method disclosed by the invention has the obvious advantages that the reaction raw materials are readily available, the tolerance to a variety of functional groups on halohydrocarbons and aldehydes is high, the yield is high, the separation and purification of a product are simple and convenient, and the like.
Active Ruthenium (0) Nanoparticles Catalyzed Wittig-Type Olefination Reaction
Srivastava, Vivek
, p. 693 - 703 (2017/03/08)
Abstract: Five different Ru metal precursors were reduced in imidazolium based ionic liquids under hydrogen atmosphere (4?bar) at 50 °C to obtain well-dispersed and stable Ru nanoparticles. Transmission electron microscopy (TEM) analysis confirmed size of well dispersed ionic liquid mediated Ru particles (Ru NPs) of 5?nm (±0.5) in diameter. These ruthenium nanoparticles (in ionic liquids) were used for Wittig type olefination reaction under mild reaction environment (70 °C and 1?h). The corresponding stilbenes were obtained in good yield with low-average selectivity. The proposed methodology is especially efficient for the synthesis of stilbenes as they were synthesized in the absence of any additive (as a hydrogen acceptor). The new catalytic system was also successfully applied for the synthesis of polymethoxylated and polyhydroxylated stilbenes, including resveratrol and DMU-212. Graphical Abstract: [Figure not available: see fulltext.]
Prevention of Marine Biofouling Using the Natural Allelopathic Compound Batatasin-III and Synthetic Analogues
Moodie, Lindon W. K.,Trepos, Rozenn,Cervin, Gunnar,Brathen, Kari Anne,Lindgard, Bente,Reiersen, Rigmor,Cahill, Patrick,Pavia, Henrik,Hellio, Claire,Svenson, Johan
supporting information, p. 2001 - 2011 (2017/08/04)
The current study reports the first comprehensive evaluation of a class of allelopathic terrestrial natural products as antifoulants in a marine setting. To investigate the antifouling potential of the natural dihydrostilbene scaffold, a library of 22 syn
Convenient One-Step Synthesis of Benzo[c]phenanthridines by Three-Component Reactions of Isochromenylium Tetrafluoroborates and Stilbenes in Acetonitrile
Chen, Gang-Gang,Wei, Jun-Qiang,Yang, Xiaoliang,Yao, Zhu-Jun
supporting information, p. 1502 - 1505 (2016/05/02)
A new type of three-component reaction of air-stable isochromenylium tetrafluoroborates with electron-rich stilbenes in acetonitrile has been developed under catalyst-free conditions in this work. This cascade multibond-formation reaction is initiated by an intermolecular oxa [4 + 2]-cycloaddition, relayed with a nucleophilic addition of acetonitrile, and terminated by an intramolecular Friedel-Crafts reaction, affording the corresponding benzo[c]phenanthridine analogues in one step.
Z-Stereoselective Aza-Peterson Olefinations with Bis(trimethylsilane) Reagents and Sulfinyl Imines
Das, Manas,OShea, Donal F.
, p. 336 - 339 (2016/02/03)
Highly stereoselective aza-Peterson olefinations from bench-stable α,α-bis(trimethylsilyl)toluene reagents and N-substituted imines have been achieved using TMSO-/Bu4N+ as Lewis base activator in THF. Remarkably, and for the first time, N-t-butanesulfinyl imines were utilized for the synthesis of Z-stilbenes with excellent selectivities, while N-aryl imines generated E-stilbenes under identical reaction conditions. The protocol proved general for numerous examples with low molecular weight byproducts formed. The origin of the Z-selectivity is proposed to be a result of diastereoselective addition to N-t-butanesulfinyl imines followed by syn-elimination of an in situ formed hypervalent silicate.
Pinosylvin-Based Polymers: Biodegradable Poly(Anhydride-Esters) for Extended Release of Antibacterial Pinosylvin
Bien-Aime, Stephan,Yu, Weiling,Uhrich, Kathryn E.
, p. 978 - 983 (2016/08/26)
Pinosylvin is a natural stilbenoid known to exhibit antibacterial bioactivity against foodborne bacteria. In this work, pinosylvin is chemically incorporated into a poly(anhydride-ester) (PAE) backbone via melt-condensation polymerization, and characteriz
