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Trans cinnamaldehyde

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https://www.readbyqxmd.com/read/27845466/organocatalytic-regiospecific-synthesis-of-1h-indene-2-carbaldehyde-derivatives-suppression-of-cycloolefin-isomerisation-by-employing-sterically-demanding-catalysts
#1
Hui Mao, Dong Wan Kim, Hun Yi Shin, Choong Eui Song, Jung Woon Yang
The regiospecific synthesis of 1H-indene-2-carbaldehyde derivatives was achieved through transition-metal-free, reductive cyclisation of ortho-formyl trans-cinnamaldehydes with Hantzsch ester in the presence of an aminocatalyst. In particular, cycloolefin isomerisation of the resulting products could be inhibited efficiently by the introduction of a sterically demanding stereo-defined aminocatalyst.
November 15, 2016: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/27796095/structure-activity-relationship-of-condensed-tannins-and-synergism-with-trans-cinnamaldehyde-against-caenorhabditis-elegans
#2
Honorata Małgorzata Ropiak, Olivier Desrues, Andrew Richard Williams, Aina Ramsay, Irene Mueller-Harvey, Stig M Thamsborg
Parasitic gastrointestinal nematodes (GIN) of livestock are increasingly developing resistance to synthetic nematocidal drugs. Moreover, the use of nematocides can induce ecotoxicity by affecting free-living nematodes. Condensed tannins (CT) are a structurally diverse group of bioactive plant compounds possessing anthelmintic activity against GIN. We investigated the relationship between the chemical structure of contrasting, purified CT and nematocidal effects using Caenorhabditis elegans. We also explored whether the nematocidal activity of CT could synergize with trans-cinnamaldehyde (CIN)...
October 31, 2016: Journal of Agricultural and Food Chemistry
https://www.readbyqxmd.com/read/27742359/fumigant-and-contact-toxicity-of-22-wooden-essential-oils-and-their-major-components-against-drosophila-suzukii-diptera-drosophilidae
#3
Junheon Kim, Miyeon Jang, Eunsik Shin, Jeongmin Kim, Si Hyeock Lee, Chung Gyoo Park
Fumigant and contact toxicities of 22 plant essential oils (EOs) from 14 families and their constituents against the adult spotted wing drosophila (SWD), Drosophila suzukii were examined. Analyses by GC, GC-MS, and NMR led to the identification of 2, 16, 13, 4, 6, 9, and 10 compounds from Gaultheria fragrantissima, Croton anistatum, Illicium verum, Liquidamabar orientalis, Cinnamomum cassia, Rosa damasena, and Santalum album, respectively. In fumigant toxicity test, G. fragrantissima, C. anistatum, and I. verum exhibited 100, 93...
October 2016: Pesticide Biochemistry and Physiology
https://www.readbyqxmd.com/read/27619325/efficacy-of-trans-cinnamaldehyde-and-eugenol-in-reducing-acinetobacter-baumannii-adhesion-to-and-invasion-of-human-keratinocytes-and-controlling-wound-infection-in-vitro
#4
Deepti P Karumathil, Meera Surendran-Nair, Kumar Venkitanarayanan
The study investigated the efficacy of two natural, plant-derived antimicrobials (PDAs), namely trans-cinnamaldehyde (TC), and eugenol (EG) for decreasing Acinetobacter baumannii adhesion to and invasion of human keratinocytes (HEK001). Moreover, the efficacy of two PDAs for inhibiting A. baumannii biofilm formation was determined using an in vitro collagen matrix wound model. Additionally, the effect of TC and EG on A. baumannii biofilm architecture was visualized using confocal scanning microscopy. Further the effect of both PDAs on genes critical for biofilm synthesis was determined using real-time quantitative polymerase chain reaction...
September 13, 2016: Phytotherapy Research: PTR
https://www.readbyqxmd.com/read/27582336/appetite-enhancing-effects-of-curry-oil
#5
Kakuyou Ogawa, Michiho Ito
Inhalation of scent compounds with phenylpropanoidal structures, such as trans-cinnamaldehyde, is expected to increase the appetite. The scent of curry powder is well known for its appetite-enhancing effect on humans. In this work, we show that the appetite of mice after inhalation of curry powder essential oil or benzylacetone showed a similar increase. The components of curry oil, trans-cinnamaldehyde, trans-anethole, and eugenol, each showed appetite-enhancing effects; therefore, these three scent compounds may be the active compounds in curry powder oil...
2016: Biological & Pharmaceutical Bulletin
https://www.readbyqxmd.com/read/27560927/novel-nad-farnesal-dehydrogenase-from-polygonum-minus-leaves-purification-and-characterization-of-enzyme-in-juvenile-hormone-iii-biosynthetic-pathway-in-plant
#6
Ahmad-Faris Seman-Kamarulzaman, Zeti-Azura Mohamed-Hussein, Chyan Leong Ng, Maizom Hassan
Juvenile Hormone III is of great concern due to negative effects on major developmental and reproductive maturation in insect pests. Thus, the elucidation of enzymes involved JH III biosynthetic pathway has become increasing important in recent years. One of the enzymes in the JH III biosynthetic pathway that remains to be isolated and characterized is farnesal dehydrogenase, an enzyme responsible to catalyze the oxidation of farnesal into farnesoic acid. A novel NAD+-farnesal dehydrogenase of Polygonum minus was purified (315-fold) to apparent homogeneity in five chromatographic steps...
2016: PloS One
https://www.readbyqxmd.com/read/27543415/trans-cinnamaldehyde-improves-memory-impairment-by-blocking-microglial-activation-through-the-destabilization-of-inos-mrna-in-mice-challenged-with-lipopolysaccharide
#7
Liqing Zhang, Zhangang Zhang, Yan Fu, Pin Yang, Zhenxia Qin, Yongjun Chen, Ying Xu
Microglia activation and neuroinflammation are critically involved in pathogenesis of neurodegenerative disorders. Patients with neurodegenerative disorders often suffer memory impairment and currently there is no effective treatment for inflammation-led memory impairment. Trans-cinnamaldehyde (TCA) isolated from medicinal herb Cinnamomum cassia has been shown to exhibit anti-inflammatory capability. However, the potential of TCA to be used to improve memory impairment under neuroinflammation has not been explored...
November 2016: Neuropharmacology
https://www.readbyqxmd.com/read/27528047/trans-cinnamaldehyde-protected-pc12-cells-against-oxygen-and-glucose-deprivation-reperfusion-ogd-r-induced-injury-via-anti-apoptosis-and-anti-oxidative-stress
#8
Xue Qi, Ru Zhou, Yue Liu, Jing Wang, Wan-Nian Zhang, Huan-Ran Tan, Yang Niu, Tao Sun, Yu-Xiang Li, Jian-Qiang Yu
Ischemia stroke is the major cause of mortality and permanent neurological disability with little definitive therapeutic options. This cerebral ischemic injury leads to the oxidative stress and eventually cell death. We hypothesized that treatment of this condition with the trans-cinnamaldehyde(TC) could protect cells from ischemic and reperfusion injury. Oxygen and glucose deprivation/reperfusion (OGD/R) was used as an in vitro model of hypoxic ischemic injury in present study. MTT was used to evaluate the protective effects of TC...
October 2016: Molecular and Cellular Biochemistry
https://www.readbyqxmd.com/read/27518479/biosynthesis-inspired-total-synthesis-of-bioactive-styryllactones-goniodiol-6s-7s-8s-goniodiol-parvistone-d-and-parvistone-e
#9
Perla Ramesh, Tadikamalla P Rao
A protecting-group-free total synthesis of (+)-goniodiol (1), (6S,7S,8S)-goniodiol (2), (-)-parvistone D (4), and (+)-parvistone E (6) was efficiently achieved in five steps from commercially available trans-cinnamaldehyde with high overall yields (72-75%). The synthesis strategy was inspired from the proposed biosynthesis pathway of styryllactones. Key transformations of the strategy include a one-pot conversion of goniothalamin oxide to goniodiol or 9-deoxygoniopypyrone in aqueous media, stereoselective epoxidation, ring-closing metathesis, and stereoselective Maruoka allylation...
August 26, 2016: Journal of Natural Products
https://www.readbyqxmd.com/read/27438841/preservation-mechanism-of-chitosan-based-coating-with-cinnamon-oil-for-fruits-storage-based-on-sensor-data
#10
Yage Xing, Qinglian Xu, Simon X Yang, Cunkun Chen, Yong Tang, Shumin Sun, Liang Zhang, Zhenming Che, Xihong Li
The chitosan-based coating with antimicrobial agent has been developed recently to control the decay of fruits. However, its fresh keeping and antimicrobial mechanism is still not very clear. The preservation mechanism of chitosan coating with cinnamon oil for fruits storage is investigated in this paper. Results in the atomic force microscopy sensor images show that many micropores exist in the chitosan coating film. The roughness of coating film is affected by the concentration of chitosan. The antifungal activity of cinnamon oil should be mainly due to its main consistent trans-cinnamaldehyde, which is proportional to the trans-cinnamaldehyde concentration and improves with increasing the attachment time of oil...
2016: Sensors
https://www.readbyqxmd.com/read/27260636/high-concentration-l-menthol-exhibits-counter-irritancy-to-neurogenic-inflammation-thermal-and-mechanical-hyperalgesia-caused-by-trans-cinnamaldehyde
#11
Hjalte H Andersen, Parisa Gazerani, Lars Arendt-Nielsen
UNLABELLED: The transient receptor potential cation channel subfamily M 8 (TRPM8) agonist L-menthol has been used traditionally for its topical counterirritant properties. Although the use of topical L-menthol for pain is casuistically established, evidence regarding its efficacy is negligible. This study aimed to characterize the effect of L-menthol as a counterirritant on cutaneous pain and hyperalgesia provoked by topical application of the transient receptor potential cation channel, subfamily A, member 1 (TRPA1) agonist trans-cinnamaldehyde (CA)...
August 2016: Journal of Pain: Official Journal of the American Pain Society
https://www.readbyqxmd.com/read/27150149/appetite-enhancing-effects-the-influence-of-concentrations-of-benzylacetone-and-trans-cinnamaldehyde-and-their-inhalation-time-as-well-as-the-effect-of-aroma-on-body-weight-in-mice
#12
Kakuyou Ogawa, Michiho Ito
Benzylacetone has appetite-enhancing and locomotor-reducing effects. The effective doses for these two outcomes overlap, and the weight gain of mice exposed to benzylacetone is caused by both appetite-enhancement and a reduction in locomotor activity. The appetite-enhancing effects of trans-cinnamaldehyde and benzylacetone have been reported previously. In this study, these appetite-enhancing effects were seen in mice after short-term, high-dose exposure.
2016: Biological & Pharmaceutical Bulletin
https://www.readbyqxmd.com/read/27141849/antipruritic-effect-of-cold-induced-and-transient-receptor-potential-agonist-induced-counter-irritation-on-histaminergic-itch-in-humans
#13
Hjalte H Andersen, Camilla Melholt, Sigurd D Hilborg, Anne Jerwiarz, Amalie Randers, Amalie Simoni, Jesper Elberling, Lars Arendt-Nielsen
A frequent empirical observation is that cold-induced counter-irritation may attenuate itch. The aim of this randomized, single-blinded, exploratory study was to evaluate the counter-irritation effects of cold-stimulation and topical application of transient receptor potential TRPA1/M8-agonists (trans-cinnamaldehyde/L-menthol, respectively), on histamine-induced itch, wheal and neurogenic inflammation in 13 healthy volunteers. Histamine 1% was applied to the volar forearms using skin prick-testing lancets. Recorded outcome-parameters were itch intensity, wheal reactions and neurogenic inflammation (measured by laser-speckle perfusion-imaging)...
May 3, 2016: Acta Dermato-venereologica
https://www.readbyqxmd.com/read/27141665/-research-progress-of-trans-cinnamaldehyde-pharmacological-effects
#14
REVIEW
Li-qing Zhang, Zhan-gang Zhang, Yan Fu, Ying Xu
Trans-cinnamaldehyde, the main component of volatile oil from cassia twig or Cinnamomum cassia, which is a traditional Chinese herbal medicine. Trans-cinnamaldehyde is a kind olefine aldehyde of organic compounds and has many pharmacological properties, such as anti-inflammatory, anti-tumor, anti-bacterial, antidiabetic, anti-obesity, and neuroprotection etc. The compound has preventive and therapeutic effects on the nervous system, cardiovascular, cancer, diabetes and other diseases. Trans-cinnamaldehyde, as a preventive care of nature medicine, has great clinical and market potential...
December 2015: Zhongguo Zhong Yao za Zhi, Zhongguo Zhongyao Zazhi, China Journal of Chinese Materia Medica
https://www.readbyqxmd.com/read/27094514/in-vivo-efficacy-of-trans-cinnamaldehyde-carvacrol-and-thymol-in-attenuating-listeria-monocytogenes-infection-in-a-galleria-mellonella-model
#15
Abhinav Upadhyay, Kumar Venkitanarayanan
Listeria monocytogenes is a major foodborne pathogen that causes life-threatening illnesses in humans. With emergence of antibiotic resistance in L. monocytogenes, there is considerable interest in testing the efficacy of alternative therapies for controlling listeriosis in humans. This study investigated the efficacy of three phytochemicals, namely trans-cinnamaldehyde (TC), carvacrol (CR), and thymol (TY) in reducing L. monocytogenes virulence in the recently established invertebrate model, Galleria mellonella...
July 2016: Journal of Natural Medicines
https://www.readbyqxmd.com/read/27087648/trans-cinnamaldehyde-an-essential-oil-in-cinnamon-powder-ameliorates-cerebral-ischemia-induced-brain-injury-via-inhibition-of-neuroinflammation-through-attenuation-of-inos-cox-2-expression-and-nf%C3%AE%C2%BA-b-signaling-pathway
#16
Yuh-Fung Chen, Yu-Wen Wang, Wei-Shih Huang, Ming-Ming Lee, W Gibson Wood, Yuk-Man Leung, Huei-Yann Tsai
Trans-cinnamaldehyde (TCA), an essential oil in cinnamon powder, may have beneficial effects as a treatment for stroke which is the second leading cause of death worldwide. Post-ischemic inflammation induces neuronal cell damage after stroke, and activation of microglia, in particular, has been thought as the main contributor of proinflammatory and neurotoxic factors. The purpose of this study was to investigate the neuroprotective effects of TCA in an animal model of ischemia/reperfusion (I/R)-induced brain injury and the neuroprotective mechanism was verified in LPS-induced inflammation of BV-2 microglial cells...
September 2016: Neuromolecular Medicine
https://www.readbyqxmd.com/read/27036441/automated-microwave-double-resonance-spectroscopy-a-tool-to-identify-and-characterize-chemical-compounds
#17
Marie-Aline Martin-Drumel, Michael C McCarthy, David Patterson, Brett A McGuire, Kyle N Crabtree
Owing to its unparalleled structural specificity, rotational spectroscopy is a powerful technique to unambiguously identify and characterize volatile, polar molecules. We present here a new experimental approach, automated microwave double resonance (AMDOR) spectroscopy, to rapidly determine the rotational constants of these compounds without a priori knowledge of elemental composition or molecular structure. This task is achieved by rapidly acquiring the classical (frequency vs. intensity) broadband spectrum of a molecule using chirped-pulse Fourier transform microwave (FTMW) spectroscopy and subsequently analyzing it in near real-time using complementary cavity FTMW detection and double resonance...
March 28, 2016: Journal of Chemical Physics
https://www.readbyqxmd.com/read/26886300/formulation-of-granules-for-site-specific-delivery-of-an-antimicrobial-essential-oil-to-the-animal-intestinal-tract
#18
Yin-Hing Ma, Qi Wang, Joshua Gong, Xiao Yu Wu
Owing to proliferation of antibiotic-resistant bacteria, the use of antibiotics for livestock growth promotion is banned in many countries and alternatives to in-feed antibiotics are needed. Cinnamon essential oil exhibits strong in vitro antibacterial activity; however, direct addition of essential oils to animal feed has limited practicality due to their high volatility, odor, fast decomposition, and poor availability in the lower intestines. To solve these problems, we formulated trans-cinnamaldehyde (CIN) with an adsorbent powder and fatty acid via a melt-solidification technique...
March 2016: Journal of Pharmaceutical Sciences
https://www.readbyqxmd.com/read/26854449/essential-oil-of-cinnamon-exerts-anti-cancer-activity-against-head-and-neck-squamous-cell-carcinoma-via-attenuating-epidermal-growth-factor-receptor-tyrosine-kinase
#19
Xin-Qing Yang, Hao Zheng, Qing Ye, Rui-Yu Li, Yong Chen
PURPOSE: Impressed by the exceptional anticancer activity of cinnamon, the present study was conducted to elucidate the anticancer potential of essential oil of Cinnamon (EOC). METHODS: EOC was tested against various cell lines (FaDu, Detroit-562 and SCC-25) of head and neck squamous cell carcinoma (HNSCC) using MTT assay. The Hep-2 cell xenograft model was used to assess the positive bio-activity of EOC. EGFR-TK inhibitory assay was also carried out to explain the possible mechanism of action of EOC...
November 2015: Journal of B.U.ON.: Official Journal of the Balkan Union of Oncology
https://www.readbyqxmd.com/read/26851241/inactivation-of-cyp2a6-by-the-dietary-phenylpropanoid-trans-cinnamic-aldehyde-cinnamaldehyde-and-estimation-of-interactions-with-nicotine-and-letrozole
#20
Jeannine Chan, Tyler Oshiro, Sarah Thomas, Allyson Higa, Stephen Black, Aleksandar Todorovic, Fawzy Elbarbry, John P Harrelson
Human exposure to trans-cinnamic aldehyde [t-CA; cinnamaldehyde; cinnamal; (E)-3-phenylprop-2-enal] is common through diet and through the use of cinnamon powder for diabetes and to provide flavor and scent in commercial products. We evaluated the likelihood of t-CA to influence metabolism by inhibition of P450 enzymes. IC50 values from recombinant enzymes indicated that an interaction is most probable for CYP2A6 (IC50 = 6.1 µM). t-CA was 10.5-fold more selective for human CYP2A6 than for CYP2E1; IC50 values for P450s 1A2, 2B6, 2C9, 2C19, 2D6, and 3A4 were 15...
April 2016: Drug Metabolism and Disposition: the Biological Fate of Chemicals
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