Psoriasis is a common inflammatory disease. It affects 1-3% of the population worldwide and is associated with increasing medical costs every year. Typical psoriatic skin lesions are reddish, thick, ...scaly plaques that can occur on multiple skin sites all over the body. Topical application of imiquimod (IMQ), a toll-like receptor (TLR)7 agonist and potent immune system activator, can induce and exacerbate psoriasis. Previous studies have demonstrated that isoflavone extract has an antioxidant effect which may help decrease inflammation and inflammatory pain. Through in vivo studies in mice, we found that the topical application to the shaved back and right ear of mice of isoflavone extract prior to IMQ treatment significantly decreased trans-epidermal water loss (TEWL), erythema, blood flow speed, and ear thickness, while it increased surface skin hydration, and attenuated epidermal hyperplasia and inflammatory cell infiltration. Through in vitro experiments, we found that isoflavone extract can reduce IL-22, IL-17A, and TNF-α-induced MAPK, NF-κB, and JAK-STAT activation in normal human epidermal keratinocytes. At the mRNA level, we determined that isoflavone extract attenuated the increased response of the TNF-α-, IL-17A-, and IL-22- related pathways. These results indicate that isoflavone extract has great potential as an anti-psoriatic agent and in the treatment of other inflammatory skin diseases.
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IZUM, KILJ, NUK, PILJ, PNG, SAZU, UL, UM, UPUK
High-dose chemotherapy using methotrexate (MTX) frequently induces side effects such as mucositis that leads to intestinal damage and diarrhea. Several natural compounds have been demonstrated of ...their effectiveness in protecting intestinal epithelial cells from these adverse effects. In this paper, we investigated the protection mechanism of lutein against MTX-induced damage in IEC-6 cells originating from the rat jejunum crypt.
The cell viability, induced-apoptosis, reactive oxygen species (ROS) generation, and mitochondrial membrane potential in IEC-6 cells under MTX treatment were examined in the presence or absence of lutein. Expression level of Bcl2, Bad and ROS scavenging enzymes (including SOD, catalase and Prdx1) were detected by quantitative RT-PCR.
The cell viability of IEC-6 cells exposed to MTX was decreased in a dose- and time-dependent manner. MTX induces mitochondrial membrane potential loss, ROS generation and caspase 3 activation in IEC-6 cells. The cytotoxicity of MTX was reduced in IEC-6 cells by the 24 h pre-treatment of lutein. We found that pre-treatment of lutein significantly reduces MTX-induced ROS and apoptosis. The expression of SOD was up-regulated by the pre-treatment of lutein in the MTX-treated IEC-6 cells. These results indicated that lutein can protect IEC-6 cells from the chemo-drugs induced damage through increasing ROS scavenging ability.
The MTX-induced apoptosis of IEC-6 cells was shown to be repressed by the pre-treatment of lutein, which may represent a promising adjunct to conventional chemotherapy for preventing intestinal damages.
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DOBA, IZUM, KILJ, NUK, PILJ, PNG, SAZU, SIK, UILJ, UKNU, UL, UM, UPUK
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•Synthesis of 3,3-difluorocyclopropene and 1-chloro-3-fluorocyclopropene from chlorocyclopropenyl cation.•The reactions of chlorocyclopropenyl cation to 3-fluorinated cyclopropenes ...were studied.•Another 3-fluorocyclopropene derivative was synthesized.•Treatment of fused tricyclic cyclopropanes with BF3●Et2O generated 1,4-diphenylnaphthalenes.
Treatment of 1-bromo-2,2-dichloro-3-trimethylsilylcyclopropane with 5 equiv of CsF resulted in the formation of a chlorocyclopropenyl cation, which, under different conditions, further reacted with fluoride ion selectively to generate 3,3-difluorocyclopropene or 1-chloro-3-fluorocyclopropene. The Diels-Alder reactions of fluorinated cyclopropene derivatives with DPIBF yielded only exo or exo-anti adducts. On treatment of fused tricyclic cis-1-chloro-3-fluorocyclopropane derivative with n-BuLi, 3-fluorocyclopropene derivative was formed, which underwent Diels-Alder reaction with DPIBF to give an endo-endo adduct. Additionally, fused tricyclic 3,3-difluorocyclopropane and cis-1-chloro-3-fluorocyclopropane derivatives were underwent ring-opening reaction of cyclopropane by BF3●Et2O, respectively, and 1,4-diphenylnaphthalene derivatives were obtained.
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GEOZS, IJS, IMTLJ, KILJ, KISLJ, NLZOH, NUK, OILJ, PNG, SAZU, SBCE, SBJE, UILJ, UL, UM, UPCLJ, UPUK, ZAGLJ, ZRSKP
A highly strained 1,3-fused tricyclic cyclopropene, tricyclo3.2.2.02,4nona-2,6-diene (15), was designed for use in the synthesis of a new highly strained anti-Bredt compound, ...bicyclo3.2.2nona-1,6,8-triene (17). Tricyclic cyclopropene 15 was subjected to a ring-opening reaction followed by insertion of the resulting carbene to produce an anti-Bredt compound 17. The tricyclic cyclopropene 15 was prepared by the fluoride-induced elimination of 2-chloro-3-trimethylsilyltricyclo3.2.2.02,4non-6-ene (20), via the reaction of 1-chloro-3-trimethylsilylcyclopropene with 1,3-cyclohexadiene. Both the tricyclic cyclopropene 15 and the anti-Bredt compound 17 were trapped by diphenylisobenzofuran (DPIBF).
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IJS, KILJ, NUK, PNG, UL, UM
1,2-Disubstituted cyclopropene, 1-methyl-2-phenylcyclopropene (18), was generated by bromo-lithium exchange of 1-bromo-2-phenylcyclopropene followed by treatment with methyl iodide. Compound 18 was ...oxidized by oxygen to give the α,β-unsaturated carbonyl product 25 and diketone 27 and the tautomeric, β-hydroxyl-α,β-unsaturated ketone 28. However, compound 28 reacted further with the cyclopropene 18 in a retro-Claisen-like reaction to generate adduct 26. Furthermore, compound 18 underwent ene dimerization in neat condition to form the endo-dimer 40 and exo-dimer 41 followed by oxidization with oxygen to give aldehyde 39. It is noteworthy that the endo-dimer 40 and exo-dimer 41 could be trapped with thiophenol to give adduct 42 and 43. In addition, the ene reaction of exo-dimer 41 with monomer 18 gave an exo-exo ene trimer 46 through an exo-transition state which was also trapped by thiophenol to give adducts 44 and 45.
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GEOZS, IJS, IMTLJ, KILJ, KISLJ, NUK, OILJ, PNG, SAZU, SBCE, SBJE, UL, UM, UPCLJ, UPUK, ZRSKP
After thiophene and furan were treated with n‐BuLi, respectively, the mixtures were reacted with various ketones and then dehydrated under acidic conditions. This reaction sequence led to the ...formation of 1‐(2‐heteroaryl)cycloalkenes and (2‐heteroaryl)alkenes. When the alkenes were treated with 10 mol % NIS, calix4arenes were produced as the major products, with minor amounts of calix6arenes sometimes being produced. Reducing the loading of NIS to 1 mol % and increasing its overall concentration to 6 M resulted in a substantial increase in the yield of hexaspirocyclohexyl calix6thiophene (from 2 to 66 %).
When 1‐(2‐thienyl)cyclohexene was treated with 10 mol % NIS, tetraspirocyclohexyl calix4thiophene was produced as the major product, with minor amounts of hexaspirocyclohexyl calix6thiophene sometimes being produced. Reducing the loading of NIS to 1 mol % and increasing its overall concentration to 6 M resulted in a substantial increase in the yield of hexaspirocyclohexyl calix6thiophene. This method could provide chemists a better condition to synthesize calix6arene derivatives.
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FZAB, GIS, IJS, KILJ, NLZOH, NUK, OILJ, SBCE, SBMB, UL, UM, UPUK
A new type of TeFe3(CO)9-incorporated dicopper NHC complex was obtained directly from one-pot reactions. By the introduction of the cluster anion TeFe3(CO)9(2-) and NHCs as the ligands, these ...di-Cu(i)-based complexes exhibited pronounced catalytic activities toward the homocoupling of arylboronic acids with low Cu loadings and high yields (up to 98%).
A simple method for the ipso nitration of aryl substituted 2‐halothiophenes that produces 2‐nitrothiophenes with regioselectivity is described. The method involves AgNO3 as the nitration reagent ...without further additives to conduct the transformation. 2‐Styryl‐5‐halothiophenes and the bisthienyl derivatives could be smoothly converted to the corresponding ipso‐nitration products in good yields. This transformation is believed to proceed via an AgIII intermediate and oxygen absorption.
Ipsodelic: A simple method for the ipso nitration of a series of aryl substituted 2‐halothiophenes to give 2‐nitrothiophenes is described. The reaction uses AgNO3, a readily available reagent, as the nitration reagent and no additives are needed for the transformation.
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FZAB, GIS, IJS, KILJ, NLZOH, NUK, OILJ, SBCE, SBMB, UL, UM, UPUK
Lutein is a carotenoid with anti-oxidant properties. Autophagy, an evolutionarily conserved catabolic cellular pathway for coping with stress conditions, is responsive to reactive oxygen species ...(ROS) and degrades damaged organelles. We previously demonstrated that lutein can induce anti-oxidant enzymes to relieve methotrexate-induced ROS stress. We therefore hypothesized that lutein, which activates ROS-scavenging enzymes, can also induce autophagy for cell survival. In this study, we demonstrated that lutein treatment attenuated the reduction in cell viability caused by H
O
. Lutein dose-dependently induced the processing of microtubule-associated protein light chain 3 (LC3)-II, an autophagy marker protein, and accumulation of LC3-positive puncta in rat intestinal IEC-6 cells. Furthermore, (a) direct observation of autophagosome formation through transmission electron microscopy, (b) upregulation of autophagy-related genes including ATG4A, ATG5, ATG7, ATG12, and beclin-1 (BENC1), and (c) increased BECN1/Bcl-2 ratio confirmed the induction of autophagy by lutein. The results revealed that bafilomycin-A1-induced inhibition of autophagy reduced cell viability and increased apoptosis in lutein-treated cells, indicating a protective role of lutein-induced autophagy. Lutein treatment also activated adenosine monophosphate-activated protein kinase (AMPK), c-Jun N-terminal kinase (JNK), and p-38, but had no effects on the induction of extracellular signal-related kinase or inhibition of mTOR; however, the inhibition of activated AMPK, JNK, or p-38 did not attenuate lutein-induced autophagy. Finally, increased BECN1 expression levels were detected in lutein-treated cells, and BECN1 knockdown abolished autophagy induction. These results suggest that lutein-induced autophagy was mediated by the upregulation of BECN1 in IEC-6 cells. We are the first to demonstrate that lutein induces autophagy. Elevated autophagy in lutein-treated IEC-6 cells may have a protective role against various stresses, and this warrants further investigation.
Auto de-bromine-coupling reactions of 1-aryl-7-bromocycloheptenes to a new series of 7-6-6 tricyclic system were described. A variety of substituents at the para-position of the phenyl were amenable ...to this transformation, including electron-donating groups and halides. The presence of electron-donating groups resulted in a more efficient reaction, with higher yields than the case of halides.
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GEOZS, IJS, IMTLJ, KILJ, KISLJ, NUK, OILJ, PNG, SAZU, SBCE, SBJE, UL, UM, UPCLJ, UPUK, ZRSKP
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