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1.
Doriguetto AC Martins FT Ellena J Salloum R dos Santos MH Moreira ME Schneedorf JM Nagem TJ 《化学与生物多样性》2007,4(3):488-499
The crystal structure of '2,2',4-trihydroxybenzophenone' (=(2,4-dihydroxyphenyl)(2-hydroxyphenyl)methanone; 1) was determined, and its molecular structure, along with intra- and intermolecular H-bonds, was analyzed. The anti-inflammatory potential of 1, evaluated by means of the rat-paw-edema assay, with carrageenan as inflammation stimulus, was found to be similar high as that of indomethacin. In contrast, benzophenone proper (2) was hardly active in this assay. Our results indicate that these anti-inflammatory effects are related to the action of kinins and prostaglandins. The radical-scavenging properties of 1 towards DPPH were found to be similar as those of typical phenolics, but somewhat lower than that of ascorbic acid. The structure-activity relationship (SAR) of 1 is discussed. 相似文献
2.
野鸦椿的植物化学成分研究 总被引:10,自引:1,他引:9
从野鸦椿 (EuscaphisjaponecaKantiz)枝叶的甲醇提取物分离得到 6个化合物 ,通过波谱分析鉴定为 5 ,7 dihydroxy 2 methyl benzopyran 4 one(Ⅰ ) ,3,4 ,5 trihydroxy benzoicacidmethylester(Ⅱ ) ,3,7 dihydroxy 5 octanolide(Ⅲ ) ,methyl 5 ,7 dihydroxy 2 (Z) octenoate(Ⅳ ) ,7 hydroxy 2 octen 5 olide(Ⅴ )和vomifoliol(Ⅵ )。 相似文献
3.
C T Hou W Brown D P Labeda T P Abbott D Weisleder 《Journal of industrial microbiology & biotechnology》1997,19(1):34-38
A bacterium isolated from a dry soil sample collected from McCalla, AL, USA, converted linoleic acid to a novel compound,
12,13,17-trihydroxy-9 (Z)-octadecenoic acid (THOA). The organism is a Gram-positive, non-motile rod (0.5 μ m × 2 μ m). It was identified as a species of Clavibacter ALA2. The product was purified by high pressure liquid chromatography, and its structure was determined by 1H and 13C nuclear magnetic resonance and Fourier transform infrared spectroscopies, and by mass spectrometer. Maximum production
of THOA with 25% conversion of the substrate was reached after 5–6 days of reaction. THOA was not further metabolized by
strain ALA2. This is the first report of a 12,13,17-trihydroxy unsaturated fatty acid and its production by microbial transformation.
Some dihydroxy intermediates were also detected. THOA has a structure similar to those of known plant self-defense substances.
Received 13 January 1997/ Accepted in revised form 05 May 1997 相似文献
4.
Jan Holgersson Annika E. Bäcker Michael E. Breimer Mikael L. Gustavsson Per-Åke Jovall Hasse Karlsson Weston Pimlott Bo E. Samuelsson 《生物化学与生物物理学报:疾病的分子基础》1992,1180(1):33-43
Blood group A glycolipid antigens have been found based upon at least four different core saccharides (types 1 to 4). The biological significance of this structural polymorphism is not known, although the successful outcome of transplantations of blood group A2 kidneys to blood group O individuals have been partly explained by the low expression of A type-3 and -4 chain glycolipid antigens in A2 kidneys. If graft rejection due to ABO incompatibility is, in any way, correlated to the expression of type-3 and -4 chain blood group glycolipids, it is of interest to identify possible blood group B structures based on these core saccharides. In a non-acid glycosphingolipid fraction isolated from human blood group B kidneys, mass spectrometry, high-temperature gas chromatography-mass spectrometry and probing of thin-layer chromatograms with Galα1–4Gal-specific Escherichia coli and monoclonal anti-B antibodies provided evidence for minute amounts of Gaα1–3(Fucα1–2)Galβ-HexNac-Galα1–4Galβ-Hex-Ceramide structure consistent with a B type-4 chain heptaglycosylceramide. In contrast, blood group A kidneys have the corresponding A type-4 chain heptaglycosylceramide as the predominant glood group A glycolipid. No, or very low activity of the blood group B gene enzyme on the type-4 chain blood group H hexaglycosylceramide precursor was found by biosynthetic experiments in vitro, which migh explain the low expression of type-4 chain blood group heptaglycosylceramides in human blood group B kidneys. 相似文献
5.
Resveratrol protects mice against SEB‐induced acute lung injury and mortality by miR‐193a modulation that targets TGF‐β signalling
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Hasan Alghetaa Amira Mohammed Muthanna Sultan Philip Busbee Angela Murphy Saurabh Chatterjee Mitzi Nagarkatti Prakash Nagarkatti 《Journal of cellular and molecular medicine》2018,22(5):2644-2655
Staphylococcal enterotoxin B (SEB) is a potent superantigen produced by Staphylococcus aureus that triggers a strong immune response, characterized by cytokine storm, multi‐organ failure, and often death. When inhaled, SEB can cause acute lung injury (ALI) and respiratory failure. In this study, we investigated the effect of resveratrol (RES), a phytoallexin, on SEB‐driven ALI and mortality in mice. We used a dual‐exposure model of SEB in C3H/HeJ mice, which caused 100% mortality within the first 5 days of exposure, and treatment with RES resulted in 100% survival of these mice up to 10 days post‐SEB exposure. RES reduced the inflammatory cytokines in the serum and lungs, as well as T cell infiltration into the lungs caused by SEB. Treatment with RES also caused increased production of transforming growth factor‐beta (TGF‐β) in the blood and lungs. RES altered the miRNA profile in the immune cells isolated from the lungs. Of these, miR‐193a was strongly induced by SEB and was down‐regulated by RES treatment. Furthermore, transfection studies and pathway analyses revealed that miR‐193a targeted several molecules involved in TGF‐β signalling (TGFβ2, TGFβR3) and activation of apoptotic pathways death receptor‐6 (DR6). Together, our studies suggest that RES can effectively neutralize SEB‐mediated lung injury and mortality through potential regulation of miRNA that promote anti‐inflammatory activities. 相似文献
6.
1,3,5‐Trihydroxy‐13,13‐dimethyl‐2H‐pyran [7,6‐b] xanthone directly targets heat shock protein 27 in hepatocellular carcinoma
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Wei‐ming Fu Wei‐mao Wang Hua Wang Xiao Zhu Yan Liang Hsiang‐fu Kung Jin‐fang Zhang 《Cell biology international》2014,38(2):272-276
7.
Trihydroxy unsaturated fatty acids with 18 carbons have been reported as plant self-defense substances. Their production in
nature is rare and is found mainly in plant systems. Previously, we reported that a new bacterial isolate, Pseudomonas aeruginosa PR3, converted oleic acid and ricinoleic acid to 7,10-dihydroxy-8(E)-octadecenoic acid and 7,10,12-trihydroxy-8(E)-octadecenoic acid, respectively. Here we report that strain PR3 converted linoleic acid to two compounds: 9,10,13-trihydroxy-11(E)-octadecenoic acid (9,10,13-THOD) and 9,12,13-trihydroxy-10(E)-octadecenoic acid (9,12,13-THOD). Stereochemical analyses showed the presence of 16 different diastereomers — the maximum
number possible. The optimum reaction temperature and pH for THOD production were 30°C and 7.0, respectively. The optimum
linoleic acid concentration was 10 mg/ml. The most effective single carbon and nitrogen sources were glucose and sodium glutamate,
respectively. However, when a mixture of yeast extract (0.05%), (NH4)2HPO4 (0.2%), and NH4NO3 (0.1%) was used as the nitrogen source, THOD production was higher by 8.3% than when sodium glutamate was the nitrogen source.
Maximum production of total THOD with 44% conversion of substrate was achieved at 72 h of incubation, after which THOD production
plateaued up to 240 h. THOD production and cell growth increased in parallel with glucose concentration up to 0.3%, after
which cell growth reached its maximum and THOD production did not increase. These results suggested that THODs were not metabolized
by strain PR3. This is the first report of microbial production of 9,10,13- and 9,12,13-THOD from linoleic acid. Journal of Industrial Microbiology & Biotechnology (2000) 25, 109–115.
Received 18 March 2000/ Accepted in revised form 09 June 2000 相似文献
8.
Plants produce short‐chain aldehydes and hydroxy fatty acids, which are important industrial materials, through the lipoxygenase pathway. Based on the information that lipoxygenase activity is up‐regulated in tobacco leaves upon infection with tobacco mosaic virus (TMV), we introduced a melon hydroperoxide lyase (CmHPL) gene, a tomato peroxygenase (SlPXG) gene and a potato epoxide hydrolase (StEH) into tobacco leaves using a TMV‐based viral vector system to afford aldehyde and hydroxy fatty acid production. Ten days after infiltration, tobacco leaves infiltrated with CmHPL displayed high enzyme activities of 9‐LOX and 9‐HPL, which could efficiently transform linoleic acid into C9 aldehydes. Protein extracts prepared from 1 g of CmHPL‐infiltrated tobacco leaves (fresh weight) in combination with protein extracts prepared from 1 g of control vector‐infiltrated tobacco leaves (as an additional 9‐LOX source) produced 758 ± 75 μg total C9 aldehydes in 30 min. The yield of C9 aldehydes from linoleic acid was 60%. Besides, leaves infiltrated with SlPXG and StEH showed considerable enzyme activities of 9‐LOX/PXG and 9‐LOX/EH, respectively, enabling the production of 9,12,13‐trihydroxy‐10(E)‐octadecenoic acid from linoleic acid. Protein extracts prepared from 1 g of SlPXG‐infiltrated tobacco leaves (fresh weight) in combination with protein extracts prepared from 1 g of StEH‐infiltrated tobacco leaves produced 1738 ± 27 μg total 9,12,13‐trihydroxy‐10(E)‐octadecenoic acid isomers in 30 min. The yield of trihydroxyoctadecenoic acids from linoleic acid was 58%. C9 aldehydes and trihydroxy fatty acids could likely be produced on a larger scale using this expression system with many advantages including easy handling, time‐saving and low production cost. 相似文献
9.
A bacterial isolate, Pseudomonas aeruginosa (PR3), has been reported to produce a new compound, 7,10,12-trihydroxy-8(E)-octadecenoic acid (TOD), from ricinoleic acid (Kuo TM, LK Manthey and CT Hou. 1998. J Am Oil Chem Soc 75: 875–879). The
reaction is unique in that it involves an introduction of two additional hydroxyl groups at carbon 7 and 10 and a rearrangement
of the double bond from carbon 9–10 (cis) to 8–9 (trans). In an effort to elucidate the metabolic pathway involved in the formation of TOD from ricinoleic acid by PR3, we have isolated
another compound from the reaction mixture using HPLC. The structure of the new compound was determined to be 10, 12-dihydroxy-8(E)-octadecenoic acid (DHOD) by GC/MS, FTIR, and NMR. The structural similarity between DHOD and TOD and the results from the
time course study of the above two compounds strongly suggested that DHOD was an intermediate in the bioconversion of ricinoleic
acid to TOD by PR3. The optimum pH and temperature for the production of DHOD from ricinoleic acid by PR3 was 6.5 and 25°C,
respectively. This is the first report on the production of 10,12-dihydroxy-8(E)-octadecenoic acid from ricinoleic acid by PR3. Journal of Industrial Microbiology & Biotechnology (2000) 24, 167–172.
Received 28 July 1999/ Accepted in revised form 18 November 1999 相似文献
10.
Polyunsaturated fatty acids and their esters are known to be susceptible to free radical-mediated oxidation, whereas cholesterol is thought to be more resistant to oxidation. In fact, it has been observed that in the case of plasma lipid peroxidation, the amount of oxidation products of polyunsaturated fatty acids such as linoleic acid was higher than that of cholesterol. In contrast, during oxidative stress-induced cellular lipid peroxidation, oxidation products of cholesterol such as 7-hydroxycholesterol (7-OHCh) were detected in greater amounts than those of linoleates such as hydroxyoctadecadienoic acid (HODE). There are several forms of oxidation products of cholesterol and linoleates in vivo, namely, hydroperoxides, as well as the hydroxides of both the free and ester forms of cholesterol and linoleates. To evaluate these oxidation products, a method used to determine the lipid oxidation products after reduction and saponification was developed. With this method, several forms of oxidation products of cholesterol and linoleates are measured as total 7-OHCh (t7-OHCh) and total HODE (tHODE), respectively. During free radical-mediated lipid peroxidation in plasma, the amount of tHODE was 6.3-fold higher than that of t7-OHCh. In contrast, when Jurkat cells were exposed to free radicals, the increased amount of cellular t7-OHCh was 5.7-fold higher than that of tHODE. Higher levels of t7-OHCh than those of tHODE have also been observed in selenium-deficient Jurkat cells and glutamate-treated neuronal cells. These results suggest that, in contrast to plasma oxidation, cellular cholesterol is more susceptible to oxidation than cellular linoleates. Collectively, cholesterol oxidation products at the 7-position may be a biomarker of cellular lipid peroxidation. 相似文献