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7 keto

Rika Nakai, Shun Fukuda, Masaya Kawase, Yoko Yamashita, Hitoshi Ashida
Certain dioxins, including 2,3,7,8,-tetrachloro-dibenzo-p-dioxin (TCDD), are exogenous ligands for an aryl hydrocarbon receptor (AhR) and induces various drug-metabolizing enzymes. In this study, we examined the effect of curcumin on expression of drug-metabolizing enzymes through the AhR and NF-E2 related factor 2 (Nrf2) pathways. Curcumin dose-dependently inhibited TCDD-induced expression of phase I enzyme cytochrome P450 1A1 (CYP1A1) and phase II enzymes NAD(P)H:quinone oxidoreductase-1 (NQO1) and heme oxygenase 1 (HO-1) but not tert-butyl hydroquinone-induced NQO1 and HO-1, suggesting that curcumin inhibited only AhR pathway, but not Nrf2 one directly...
December 1, 2017: Bioscience, Biotechnology, and Biochemistry
Xiuhua Lan, Kejun Deng, Jianping Zhao, Yiyi Chen, Xuhui Xin, Yanli Liu, Ikhlas A Khan, Shilin Yang, Taoyun Wang, Qiong Ming Xu
Ten compounds were isolated and identified from green vegetable soya beans, of which five triterpenoid saponins (1-5) are new, and five compounds (6-10) are known. The chemical structures of five triterpenoid saponins (1-5) were elucidated to be 3β,24-dihydroxy-22β,30-epoxy-30-oxoolean-12-en 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranosyl-(1→2)-β-D-glucuronopyranoside, 1, 3β,24-dihydroxy-22β,30-epoxy-30-oxoolean-12-en 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-(3''-O-formyl)-galactopyranosyl-(1→2)-β-D-glucuronopyranoside, 2, 22-keto-3β,24-dihydroxy oleanane-12-ene 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-(3''-O-formyl)-galactopyranosyl-(1→2)-β-D-glucuronopyranoside, 3, 3β,22β,24-trihydroxy oxyolean-18(19)-ene-29-acid 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranoside, 4, and punicanolic acid 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranoside, 5, in terms of spectroscopic data (IR, GTC/FID, HR-ESI-MS, 1D and 2D NMR)...
November 29, 2017: Journal of Agricultural and Food Chemistry
Jung-Kyun Woo, Thi Kim Quy Ha, Dong-Chan Oh, Won-Keun Oh, Ki-Bong Oh, Jongheon Shin
Six new polyoxygenated steroids (1-6) along with clathriol (7) were isolated from the Korean marine sponge Clathria gombawuiensis. Based upon the results of combined spectroscopic analyses, the structures of gombasterols A-F (1-6) were elucidated to be those of highly oxygenated steroids possessing a 3β,4α,6α,7β-tetrahydroxy or equivalent (7β-sodium O-sulfonato for 3) substitution pattern and a C-15 keto group as common structural motifs. The relative and absolute configurations of these steroids, including the rare 14β configuration of 1-4, were determined by a combination of NOESY, J-based analyses, the 2-methoxy-2-(trifluoromethyl)phenylacetic acid (MTPA) method, and X-ray crystallographic analysis...
November 28, 2017: Journal of Natural Products
Ing-Jung Chen, Siow-Wey Hee, Chun-Hsing Liao, Shih-Yao Lin, Lynn Su, Chia-Tung Shun, Lee-Ming Chuang
Sepsis is a systemic inflammation accompanied by multi-organ dysfunction due to microbial infection. Prostaglandins and their metabolites have long been studied for their importance in regulating the innate immune response. 15-keto-PGE2 (15k-PGE2) is a prostaglandin E2 (PGE2) metabolite, whose further processing is catalyzed by prostaglandin reductase 2 (PTGR2). We showed disruption of the Ptgr2 gene in mice improves the survival rate under both LPS- and cecum ligation/puncture (CLP)-induced experimental sepsis...
November 22, 2017: Free Radical Biology & Medicine
Md Abdul Muhit, Kaoru Umehara, Hiroshi Noguchi
EtOAc extract from the leaves of Terminalia citrina collected in Bangladesh were separated, and seven previously undescribed α-keto tetrahydrofuran lignan glucosides (terminalosides Q to W) were isolated and characterized. NOESY analysis of (1)H NMR spectra and ECD spectroscopic data analysis revealed the absolute stereochemistry of the tetrahydrofuran ring of the isolated constituents as being a (7S,8R,8'S)- configuration in terminalosides Q to U and a (7R,8R,8'S)- configuration in terminalosides V and W...
November 14, 2017: Phytochemistry
J C Ferreira, L F Novaes Filho, Y L Boakari, H S Canesin, D L Thompson, F S Lima, C Meira
The aim of the current project was to characterize the luteal vascularity and the plasma concentrations of progesterone (P4), prolactin (PRL) and 13,14-dihydro-15-keto-PGF2α (PGFM) in mares with luteal disturbances during early and mid-diestrus. In Experiment 1, twenty-one mares were treated with 2 mL of 0.9% NaCl, or 1 mg Dinoprost, or 10 mg Dinoprost on day two after ovulation (Control-D2, 1/10PGF-D2 and PGF-D2 groups, respectively; n = 7 mares/group). In Experiment 2, similar treatments were performed eight days post-ovulation using a different cohort of 21 mares (Control-D8, 1/10PGF-D8 and PGF-D8 groups, respectively; n = 7 mares/group)...
November 4, 2017: Theriogenology
R K Kasimanickam, J B Hall, C T Estill, J P Kastelic, C Joseph, R L Abdel Aziz, D Nak
Objectives were to determine effects of: 1) handling temperament and administration of flunixin meglumine, an inhibitor of prostaglandin F2a (PGF2a) synthesis, given at the time of embryo transfer, on pregnancy rates in beef cattle embryo transfer recipients; 2) handling temperament and flunixin meglumine on peripheral concentrations of progesterone, cortisol, substance-P, prostaglandin F metabolites (PGFM, (13,14-dihydro-15-keto-PGF2a) and isoprostane 8-epi PGF2a; and 3) flunixin meglumine treatment on proportion of non-pregnant recipient cows returning to estrus within an expected interval...
November 10, 2017: Theriogenology
Zhi-Qiang Hao, Jing-Pei Cao, Xiao-Yan Zhao, Yan Wu, Jun-Sheng Zhu, Ya-Li Dang, Qi-Qi Zhuang, Xian-Yong Wei
A novel strategy is proposed for the increase of specific surface area (SSA) of porous carbon sphere (PCS) by oxidation and activation. 2-keto-l-gulonic acid mother liquor (GAML) as a high-pollution waste has a relatively high value of reutilization. For its high value-added utilization, GAML is used as the precursor for preparation of PCS as carbon-based electrode materials for electric double-layer capacitor. PCS is prepared by hydrothermal carbonization, carbonization and KOH activation, and Fe(NO3)3 9H2O is used as an oxidizing agent during carbonization...
November 3, 2017: Journal of Colloid and Interface Science
Corey E Perez, Hyun Bong Park, Jason M Crawford
Nonribosomal peptide synthetases (NRPSs) produce a wide variety of biologically important small molecules. NRPSs can interface with other enzymes to form hybrid biosynthetic systems that expand the structural and functional diversity of their products. The pepteridines are metabolites encoded by an unprecedented pteridine-NRPS-type hybrid biosynthetic gene cluster in Photorhabdus luminescens, but how the distinct enzymatic systems interface to produce these molecules has not been examined at the biochemical level...
November 7, 2017: Biochemistry
Anthony P Green, Simon Hardy, Alan T L Lee, Eric J Thomas
The first total synthesis of a derivative of a 20-deoxybryostatin, namely 7-des-O-pivaloyl-7-O-benzylbryostatin 10 is described. Preliminary studies demonstrated that the modified Julia reactions of 2-benzothiazolylsulfones corresponding to the C17-C27 fragment with aldehydes corresponding to the C1-C16 fragment, provided an efficient and stereoselective assembly of advanced intermediates with the (E)-16,17-double-bond. The synthesis of the C1-C16 fragment was then modified so that the C1 acid was present as its allyl ester before the Julia coupling...
November 15, 2017: Organic & Biomolecular Chemistry
Fionn T McSwiney, Bruce Wardrop, Parker N Hyde, Richard A Lafountain, Jeff S Volek, Lorna Doyle
BACKGROUND: Low-carbohydrate diets have recently grown in popularity among endurance athletes, yet little is known about the long-term (>4 wk) performance implications of consuming a low-carbohydrate high fat ketogenic diet (LCKD) in well-trained athletes. METHODS: Twenty male endurance-trained athletes (age 33 ± 11y, body mass 80 ± 11kg; BMI 24.7 ± 3.1 kg/m2) who habitually consumed a carbohydrate-based diet, self-selected into a high-carbohydrate (HC) group (n = 11, %carbohydrate:protein:fat = 65:14:20), or a LCKD group (n = 9, 6:17:77)...
November 3, 2017: Metabolism: Clinical and Experimental
V S Anithaa, S Vijayakumar, M Sudha, R Shankar
The interaction of diketo and keto-enol form of thymine and uracil tautomers with acridine (Acr), phenazine (Phen), benzo[c]cinnoline (Ben), 1,10-phenanthroline (1,10-Phe), and 4,7-phenenthroline (4,7-Phe) intercalating drug molecules was studied using density functional theory at B3LYP/6-311++G** and M05-2×/6-311++G** levels of theory. From the interaction energy, it is found that keto-enol form tautomers have stronger interaction with intercalators than diketone form tautomers. On complex formation of thymine and uracil tautomers with benzo[c]cinnoline the drug molecules have high interaction energy values of -20...
November 6, 2017: Journal of Molecular Modeling
N Idayu Zahid, Mohamad Syafie Mahmood, Balamurugan Subramanian, Suhana Mohd Said, Osama K Abou-Zied
Fluorescence upconversion and transient absorption techniques are used to explain the source of the intense red/near-infrared emission of crystalline 4-dimethylamino-2'-hydroxychalcone. We found that the initially excited enol form undergoes tautomerization in 3 ps to form the keto tautomer. The latter is stable in the ground state as a consequence of J-type aggregation in the crystal packing and is manifested in an absorption peak at 550 nm that spectrally overlaps with the short-lived enol emission, leading to self-reabsorption and adding a factor to the complete depletion of the enol emission...
November 3, 2017: Journal of Physical Chemistry Letters
Aya Shoukry Sayed, Iman Emam Omar Gomaa, Michael Bader, Nesrine Salah El Dine El Sayed
Neuroinflammation is one of the most important mechanisms underlying neurodegeneration. Lipopolysaccharide (LPS) is a potent inflammogen which causes cognitive dysfunction. Boswellia serrata is known since many years as a powerful anti-inflammatory herbal drug. Its beneficial effect mainly arises from inhibition of 5-lipoxygenase (5-LO) enzyme. 3-acetyl-11-keto-β-boswellic acid (AKBA) is the most potent 5-LO inhibitor extracted from the oleo-gum-resin of Boswellia serrata. The aim of the present work is to study the molecular mechanisms underlying the anti-inflammatory and neuroprotective effects of AKBA and dexamethasone (DEX) in LPS-induced neuroinflammatory model...
October 27, 2017: Molecular Neurobiology
Hongjing Fan, Min Li, Li Yu, Weifeng Jin, Jiehong Yang, Yuyan Zhang, Haitong Wan
ETHNOPHARMACOLOGICAL RELEVANCE: Danhong Injection (DHI), a Chinese medical product extracted from Radix et Rhizoma Salviae Miltiorrhizae (Salvia miltiorrhiza Bge., Labiatae, Danshen in Chinese) and Flos Carthami (Carthamus tinctorius L., Compositae, Honghua in Chinese), has been reported to have effects on inflammatory, anti-fibrinolytic properties, antithrombotic and decrease blood-lipid. It is extensively used for the clinical treatment of cardiovascular disease. This study aimed to investigate the effects of DHI on blood-lipid levels and platelet aggregation rate in hyperlipidemia rats...
October 21, 2017: Journal of Ethnopharmacology
Francis K Yoshimoto, Hadi D Arman, Wendell P Griffith, Fangzhi Yan, Daniel J Wherritt
7α-Hydroxypregnenolone is an endogenous neuroactive steroid that stimulates locomotor activity. A synthesis of 7α-hydroxypregnenolone from pregnenolone, which takes advantage of an orthogonal protecting group strategy, is described. In detail, the C7-position was oxidized with CrO3 and 3,5-dimethylpyrazole to yield a 7-keto steroid intermediate. The resulting 7-ketone was stereoselectively reduced to the 7α-hydroxy group with lithium tri-sec-butylborohydride. In contrast, reduction of the same 7-ketone intermediate with NaBH4 resulted in primarily the 7β-hydroxy epimer...
October 20, 2017: Steroids
Jing Yang, Yi Xu, Hao-Yu Liu, Rui-Min Han, Jian-Ping Zhang, Leif H Skibsted
Genistein, but not daidzein, binds to copper(II) with a 1:2 stoichiometry in ethanol and with a 1:1 stoichiometry in methanol, indicating chelation by the 5-phenol and the 4-keto group of the isoflavonoid as demonstrated by the Jobs method and UV-visible absorption spectroscopy. In ethanol, the stability constants had the value 1.12 × 10(11) L²∙mol(-2) for the 1:2 complex and in methanol 6.0 × 10⁵ L∙mol(-1) for the 1:1 complex at 25 °C. Binding was not detected in water, as confirmed by an upper limit for the 1:1 stability constant of K = 5 mol(-1) L as calculated from the difference in solvation free energy of copper(II) between methanol and the more polar water...
October 18, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Onur Yücel, Johannes Holert, Kevin Christopher Ludwig, Sven Thierbach, Bodo Philipp
Bile salts such as cholate are steroid compounds with a C5 carboxylic side chain and occur ubiquitously in vertebrates. Upon their excretion into soils and waters bile salts can serve as growth substrates for diverse bacteria. Novosphingobium sp. strain Chol11 degrades 7-hydroxy bile salts via 3-keto-7-deoxy-Δ(4,6) metabolites by dehydration of the 7-hydroxyl group catalyzed by the 7α-hydroxysteroid dehydratase Hsh2. This reaction has not been observed in the well-studied 9-10-seco degradation pathway used by other steroid-degrading bacteria indicating that strain Chol11 uses an alternative pathway...
October 20, 2017: Applied and Environmental Microbiology
Leslie J Donato, Alan Lueke, Stacy M Kenyon, Jeffrey W Meeusen, Michael Camilleri
BACKGROUND: Imbalance of bile acids (BA) homeostasis in the gastrointestinal tract can lead to chronic diarrhea or constipation when BA in the colon are in excess or low, respectively. Since both disturbances of bowel function can result from other etiologies, identifying BA imbalance is important to tailor treatment strategies. Serum concentrations of 7-alpha-hydroxy-4-cholesten-3-one (7aC4), a precursor in bile acid synthesis, reflect BA homeostasis. Here we describe a method to accurately measure serum 7aC4 and evaluate the clinical utility in patients with diarrhea or constipation phenotypes...
October 16, 2017: Clinical Biochemistry
Wei Qin, Katherine R Heal, Rasika Ramdasi, Julia N Kobelt, Willm Martens-Habbena, Anthony D Bertagnolli, Shady A Amin, Christopher B Walker, Hidetoshi Urakawa, Martin Könneke, Allan H Devol, James W Moffett, E Virginia Armbrust, Grant J Jensen, Anitra E Ingalls, David A Stahl
Four mesophilic, neutrophilic, and aerobic marine ammonia-oxidizing archaea, designated strains SCM1(T), HCA1(T), HCE1(T) and PS0(T), were isolated from a tropical marine fish tank, dimly lit deep coastal waters, the lower euphotic zone of coastal waters, and near-surface sediment in the Puget Sound estuary, respectively. Cells are straight or slightly curved small rods, 0.15-0.26 µm in diameter and 0.50-1.59 µm in length. Motility was not observed, although strain PS0(T) possesses genes associated with archaeal flagella and chemotaxis, suggesting it may be motile under some conditions...
October 16, 2017: International Journal of Systematic and Evolutionary Microbiology
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