Search PubMed⌕ Search

SEARCH · Search PubMed

Results for “Pyrones”

Search indexed PubMed citations on genomics, clinical trials, systematic reviews and public health. Explore titles, authors and supplied subject terms, then open the PubMed record.

Quote a phrase for an exact phrase match. Source license links do not imply unrestricted reuse.

At least 1,405 records · Page 78Linked to original sources
PubMed2006

Stereoselective total synthesis of the proposed structure of 2-epibotcinolide.

[Structure: see text] The total synthesis of pseudo 2-epibotcinolide (1b) through several featured synthetic approaches has been attained. First, the chiral linear precursors of the nine-membered ring compound is stereoselectively constructed by the asymmetric aldol reaction for producing beta-hydroxy ester units. Second, the key cyclization reaction to form the nine-membered lactone moiety is efficiently achieved by the extremely facile and powerful mixed-anhydride method promoted by 2-methyl-6-nitrobenzoic anhydride (MNBA) with basic promoters.

Botrytis↗
PubMed2007

Total synthesis and biological evaluation of verticipyrone and analogues.

[reaction: see text] Total synthesis of verticipyrone, a novel NADH-fumarate reductase inhibitor, has been accomplished by a convergent approach using novel "Reverse Julia olefination" method. During total synthetic studies, we also prepared and evaluated several synthetic verticipyrone analogues, some of which exhibited more potent antiparasitic activity than the natural verticipyrone.

Aldehydes↗
PubMed2007

Synthesis of psymberin analogues: probing a functional correlation with the pederin/mycalamide family of natural products.

In this letter we describe an efficient synthesis of "psympederin", a hybrid between the novel antitumor natural product psymberin and the blister beetle toxin pederin. Evaluation of antiproliferative activity reveals that the dihydroisocoumarin fragment is important for psymberin toxicity and the cyclic pederate fragment is important for pederin/mycalamide toxicity. On the basis of preliminary results described herein, we speculate that, despite their structural resemblance, psymberin and pederin/mycalamide induce toxicity through different mechanisms. [reaction: see text].

Cell Line, Tumor↗
PubMed1999

Hetero [4 + 2] cycloadditions of (trialkylsilyl)vinylketenes. Synthesis of alpha,beta-unsaturated delta-valerolactones and -lactams.

[formula: see text] Hetero Diels-Alder reactions of (trialkylsilyl)vinylketenes (TAS-vinylketenes) with carbonyl and imino dienophiles are described. TAS-vinylketenes participate as electron-rich dienes in [4 + 2] cycloadditions with diethyl ketomalonate to afford alpha,beta-unsaturated delta-valerolactones in good yield. Nonenolizable N-alkyl- and N-(trimethylsilyl)imines combine with TAS-vinylketenes to furnish alpha,beta-unsaturated delta-valerolactams. In contrast to most Diels-Alder reactions involving unactivated imines, these cycloadditions do not require promotion by Lewis acids and in general proceed with a high degree of stereoselectivity.

Cyclization↗
PubMed1999

Gram-scale synthesis of (+)-discodermolide.

[formula: see text] A triply convergent, highly efficient second-generation synthesis of the potent antimitotic agent (+)-discodermolide (1) has been achieved on a 1-g scale.

Alkanes↗
PubMed1999

Effects of bis(maltolato) oxovanadium (IV) on protein serine kinases in skeletal muscle of streptozotocin-diabetic rats.

The in vivo effects of bis(maltolato)oxovanadium (IV) (BMOV) on the activity of protein serine kinases in skeletal muscle of STZ-diabetic Wistar rats were studied. BMOV was administered to STZ-diabetic rats at a concentration of 0.75 mg/ml for 8 weeks. Chronic BMOV treatment completely normalized plasma glucose levels in the diabetic animals after 8 weeks of treatment. Insulin-stimulated ERK-1 and ERK-2 activity was markedly increased in STZ-diabetic rats. Chronic BMOV treatment normalized the activity of ERK-2 in the diabetic treated animals, whereas the activity of ERK-1 was unaffected. In contrast to ERK-1 and ERK-2, the activity of the ribosomal S6 kinase p90rsk was decreased in STZ-diabetic rats. BMOV treatment restored the activity to normal levels. Basal p70 S6K activity was increased about 2.5-fold in the untreated diabetic group and no further increase in activity was observed after insulin stimulation. BMOV treatment did not correct the changes in p70 S6K activity in either the basal or insulin-stimulated states. In conclusion (i) the activity of ERK-1, ERK-2 and p90rsk were altered in skeletal muscle of STZ-diabetic rats; (ii) the glucoregulatory effects of BMOV were accompanied by concurrent improvement in the activities of ERK-2 and p90rsk; and (iii) there appears to be a dissociation between the activation of ERK-2 and p90rsk, suggesting that the regulation of p90rsk may be much more complex in vivo.

Animals↗
PubMed2001

In vivo effects of vanadium on GLUT4 translocation in cardiac tissue of STZ-diabetic rats.

The effect of vanadium treatment on insulin-stimulated glucose transporter type 4 (GLUT4) translocation was studied in cardiac tissue of streptozotocin (STZ)-induced diabetic rats by determining the subcellular distribution of GLUT4. Four groups of rats were examined: control and diabetic, with or without bis(maltolato)oxovanadium(IV) (BMOV, an organic form of vanadium) treatment for 8 weeks. The effect of vanadium on insulin-induced GLUT4 translocation was studied at 5 min as the early insulin response and at 15 min after insulin injection as the maximal insulin response. At 5 min after insulin injection, plasma membrane GLUT4 level in the diabetic-treated group was not different from the control groups and was significantly higher than that of the insulin-stimulated diabetic group, indicating an enhancement of insulin response on GLUT4 translocation brought about by vanadium treatment. In contrast to that at 5 min after insulin injection, no significant difference in the plasma membrane GLUT4 level was observed between the diabetic and the diabetic-treated groups at 15 min after insulin injection. GLUT4 mobilization from the intracellular pool in response to insulin was also investigated at 15 min after insulin injection. Basal intracellular GLUT4 content was significantly higher in the diabetic-treated group when compared to the diabetic group under the same condition. However, the increased basal intracellular GLUT4 in the diabetic-treated group did not result in more insulin-mediated GLUT4 translocation at 15 min after insulin injection. In conclusion, the finding that plasma membrane GLUT4 in the diabetic-treated group is significantly higher than that of the diabetic group at 5 min but not at 15 min post-insulin injection indicates that vanadium treatment enhances insulin-mediated GLUT4 translocation in cardiac tissue by enhancing its early response.

Animals↗
PubMed2001

Evaluation of carboxymethylpullulan as a novel carrier for targeting immune tissues.

PURPOSE: To demonstrate the potential of carboxymethylpullulan (CMPul) as a carrier for targeting immune tissues, and to find whether immune tissues could be set as the target of an immunosuppressant to treat autoimmune diseases. METHODS: The biodistribution of CMPul was investigated to evaluate its potency as a carrier for targeting immune tissues. Furthermore, an immunosuppressant-CMPul conjugate was prepared and its suppressive effect on rat adjuvant arthritis was examined. RESULTS: The disappearance rate of 3H-labeled CMPul from the blood circulation was much slower than that of 3H-labeled pullulan (Pul) after intravenous injection to normal rats. The concentration of 3H-labeled CMPul in the spleen and lymph nodes was much higher than that of 3H-labeled Pul at 24 hours after the injection, whereas the concentration of 3H-labeled CMPul in the liver was significantly lower than that of 3H-labeled Pul. A similar targeting property of 3H-labeled CMPul for these immune tissues was observed in arthritic rats. A conjugate composed of a novel immunosuppressant PA-48153C and CMPul showed a suppressive effect on rat adjuvant arthritis judging from a reduction of the arthritic index and spleen weight and an increase of body weight. CONCLUSIONS: CMPul is expected to be a promising carrier for targeting immune tissues with an immunosuppressant to enable treatment of autoimmune diseases.

Animals↗
PubMed2002

Characterization of (1'R,4S,4aR,7S,7aR)-dihydronepetalactol as a semiochemical for lacewings, including Chrysopa spp. and Peyerimhoffina gracilis.

The enantiomerically pure diastereoisomers (1R,4S,4aR,7S,7aR)- (1) and (1R,4R,4aR,7S,7aR)-dihydronepetalactol (2) were synthesized diastereoselectively from a renewable resource, (4aS,7S,7aR)-nepetalactone (3), isolated as the main constituent of the essential oil of the catmint plant Nepeta cataria. The stereochemistry of the compounds was determined by NMR spectroscopy and X-ray crystallography, and the compounds were identified, respectively, as neomatatabiol and isoneomatatabiol, natural products from Actinidia polygama, for which the lactol stereochemistry was previously incompletely defined. Compound 1 was found to catch significant numbers of three species of lacewing in the field: in Korea. Chrysopa cognata, and in the United Kingdom, Nineta vittata and most notably Peverimhoffina gracilis. All species caught in significant numbers were found more frequently in traps releasing 1 than 2, while more C. cognata, C. formosa, and C. phyllochroma were found in traps releasing (1R,4aS,7S,7aR)-nepetalactol (4). The catch of P. gracilis with 1 is of particular interest as this lacewing has only recently been recorded in the United Kingdom. Where sexed, the lacewings of all species trapped were found to be male, implying a possible pheromonal role for these or structurally related compounds.

Animals↗
PubMed2002

Vanadium increases GLUT4 in diabetic rat skeletal muscle.

The effect of vanadium in lowering blood glucose in diabetic animals is well established; however, the exact mechanism of action of vanadium still eludes us. There are several reports from in vitro studies indicating that vanadium increases enzyme activity in insulin signalling pathways; however, these findings have not been duplicated in vivo. Glucose transporters (GLUT) have a major role to play in any glucoregulatory effects. Insulin dependent GLUT4 is a major glucose transporter present in skeletal muscle, adipocytes and heart. In the present study we found that the plasma glucose in streptozotocin (STZ) diabetic animals was restored to normal following treatment with a single dose of BMOV, an organic vanadium compound, given by oral gavage (0.6 mmol/kg), similar to the response with chronic BMOV treatment. The response to BMOV by oral gavage was rapid and the animals were normoglycemic within 24 h of treatment and still demonstrated a significant effect even after 72 h. Using a specific antibody against GLUT4 we found an overall reduction in the GLUT4 in the total membrane fraction in skeletal muscle of diabetic animals. However, with a single dose of BMOV the GLUT4 level was restored to normal. This is the first report that establishes a direct effect of vanadium on the regulation of GLUT4 expression in diabetic animals in vivo, and may at least partially explain the glucoregulatory effects of vanadium.

Animals↗
PubMed2001

Aluminum-induced apoptosis in PC12D cells.

The addition of aluminum-maltol complex to PC12D cells induced a time-dependent and concentration-dependent growth inhibition as well as cell death, whereas aluminum chloride or maltol alone did not affect the viability of PC12D cells. Apoptosis of differentiated PC12D cells was assessed by using terminal deoxynucleotidyltransferase-mediated 2'-deoxyuridine-5'-triphosphate nick end labeling (TUNEL) technique to detect DNA strand breaks in situ. The number of TUNEL-positive cells treated with aluminum-maltol increased with time in the treatment cultures. The ability of aluminum ion to elevate intracellular reactive oxygen species was determined by fluorescence in PC12D cells loaded with the oxidant-sensitive dye 2',7'-dichlorofluorescin diacetate. Aluminum ion incorporated to PC 12D cells causes apoptotic cell death by enhancing the generation of reactive oxygen species.

Aluminum↗
PubMed2001

In vivo effects of vanadium in diabetic rats are independent of changes in PI-3 kinase activity in skeletal muscle.

The PI-3 kinase signalling pathway is an important pathway in mediating the glucoregulatory effects of insulin and skeletal muscle (SKM) is the major tissue involved in glucose utilization. In diabetes this pathway is impaired, either due to lack of insulin as in Type I diabetes, or due to insulin resistance as in Type 2 diabetes. Bis(maltolato)-oxovanadium IV (BMOV), an insulin mimetic/enhancing agent, produces a marked glucose lowering effect in models of both types of diabetes. Some in vitro studies have shown that phosphatidylinositol 3 kinase (PI-3 kinase) activity is enhanced by vanadium. In the present study we looked at changes in PI-3 kinase expression and activity in SKM from STZ-diabetic and fa/fa Zucker rats treated with BMOV for 3 weeks. Although BMOV treatment completely normalized glucose levels in STZ-diabetic rats, no effect was observed on basal or insulin-stimulated PI-3 kinase activity. In fatty Zucker rats, activation of PI-3 kinase activity after insulin injection was impaired as compared to age matched lean controls, but BMOV again did not affect the activity. These results suggest that although PI-3 kinase is an important signalling factor in glucose utilization, vanadium treatment does not reduce hyperglycemia through activation of SKM PI-3 kinase in vivo.

Animals↗
PubMed2001

In vivo effects of insulin and bis(maltolato)oxovanadium (IV) on PKB activity in the skeletal muscle and liver of diabetic rats.

In this study, the in vivo effects of insulin and chronic treatment with bis(maltolato)oxovanadium (IV) (BMOV) on protein kinase B (PKB) activity were examined in the liver and skeletal muscle from two animal models of diabetes, the STZ-diabetic Wistar rat and the fatty Zucker rat. Animals were treated with BMOV in the drinking water (0.75-1 mg/ml) for 3 (or 8) weeks and sacrificed with or without insulin injection. Insulin (5 U/kg, i.v.) increased PKBalpha activity more than 10-fold and PKBbeta activity more than 3-fold in both animal models. Despite the development of insulin resistance, insulin-induced activation of PKBalpha was not impaired in the STZ-diabetic rats up to 9 weeks of diabetes, excluding a role for PKBalpha in the development of insulin resistance in type 1 diabetes. Insulin-induced PKBalpha activity was markedly reduced in the skeletal muscle of fatty Zucker rats as compared to lean littermates (fatty: 7-fold vs. lean: 14-fold). In contrast, a significant increase in insulin-stimulated PKBalpha activity was observed in the liver of fatty Zucker rats (fatty: 15.7-fold vs. lean: 7.6-fold). Chronic treatment with BMOV normalized plasma glucose levels in STZ-diabetic rats and decreased plasma insulin levels in fatty Zucker rats but did not have any effect on basal or insulin-induced PKBalpha and PKBbeta activities. In conclusion (i) in STZ-diabetic rats PKB activity was normal up to 9 weeks of diabetes; (ii) in fatty Zucker rats insulin-induced activation of PKBalpha (but not PKBbeta) was markedly altered in both tissues; (iii) changes in PKBalpha activity were tissue specific; (iv) the glucoregulatory effects of BMOV were independent of PKB activity.

Animals↗
PubMed2002

Bis(maltolato)oxovanadium(IV) inhibits the activity of PTP1B in Zucker rat skeletal muscle in vivo.

The insulin signalling pathway consists of a series of phosphorylation and dephosphorylation steps inside the target cell. Phosphotyrosine phosphatase 1B (PTP1B) dephosphorylates phosphotyrosine (pTyr) residues present on the insulin receptor (IR). In this study we examined the effect of bis(maltolato)oxovanadium(IV) (BMOV) on PTP1B and its possible role in the amelioration of insulin resistance. Fourteen to sixteen week old fatty Zucker rats (F), an animal model of insulin resistance, were treated with BMOV in drinking water for 3 weeks (FT) along with age matched lean littermate controls. The fatty rats responded to vanadium with a significant decrease in plasma insulin, (F = 5.1+/-0.8 FT = 3.3+/-0.7 ng/ml). During insulin resistance the activity of PTP1B has been shown to increase, thus diminishing insulin signalling in the target tissues. Hence, PTP1B is an important target for anti-diabetic drug research. In our investigation we found that the PTP1B activity was increased to 200% in the skeletal muscle of untreated Zucker fatty rats compared to lean littermates. Three weeks of BMOV treatment reduced the activity of PTP1B by 25% in fatty treated rats, in vivo, compared to untreated fatty rats. There was no significant change in the activity of PTP1B in the lean treated rats. There was also no difference in the gene expression of PTP1B in the skeletal muscle of different groups of rats. Vanadium compounds also inhibited PTP1B in vitro. These results indicate that PTP1B may be a potential target for the action of BMOV at least in the Zucker fatty rat model.

Animals↗
PubMed2003

Regioselective synthesis of kojic acid esters by Bacillus subtilis protease.

The lipophilicity of kojic acid [5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one] was improved by esterifying kojic acid with either divinyl adipate, vinyl hexanoate, vinyl octanoate or vinyl decanoate using protease from Bacillus subtilis for 7 d. 1H-NMR and 13C-NMR showed that the primary hydroxyl group at the C-7 position of kojic acid was regioselectively esterified to afford 7-O-vinyl adipoyl kojic acid, 7-O-hexanoyl kojic acid, 7-O-octanoyl kojic acid and 7-O-decanoyl kojic acid (13-27% yield). The kojic acid esters had radical scavenging activities, inhibited tyrosinase activity and was biodegradable.

Bacillus subtilis↗
PubMed2004

Combining induced mutation and protoplasting for strain improvement of Aspergillus oryzae for kojic acid production.

By combining induced mutation, using NTG and UV irradiation, and protoplasting of a wild type strain of Aspergillus oryzae ATCC 22788, a hyper-producing strain was obtained that accumulated 41 g kojic acid l(-1) in shake-flasks, which was 100-fold higher than that in the wild type strains. Similar production of kojic acid was obtained in 5 l stirred-tank fermentations.

Aspergillus oryzae↗