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PubMed1980

Modification of cell membrane lipids in Micrococcus lysodeikticus induced by pantoyl lactone.

Growth of Microccoccus lysodeikticus in the presence of pantoyl lactone brings about both qualitative and quantitative changes in cell membrane lipids. Significant amounts of the two major phospholipids (phosphatidylglycerol and diphosphatidylglycerol) are converted to lyso forms; the largest conversion occurs in the phosphatidylglycerol. In addition, amounts of several phospholipid fatty acids are changed. Physical alteration of the call membrane can be demonstrated using differential scanning calorimetry. Although growth and transport are significantly inhibited when pantoyl lactone is present, cells possessing altered call membrane phospholipds and phospholipid fatty acids, brought about by growth in the presence of pantoyl lactone, transport D-alanine, L-glutamic and L-aspartic acid normally when washed free of the pantoyl lactone.

4-Butyrolactone↗
PubMed1989

Expression of the mutant gene for L-gulono-gamma-lactone oxidase in scurvy-prone rats.

A mutant strain of Wistar rats with L-gulono-gamma-lactone oxidase deficiency has recently been established. To investigate this deficiency by DNA and RNA blot hybridization analyses, a fragment of a previously cloned cDNA encoding rat L-gulono-gamma-lactone oxidase was used as a probe. When genomic DNA of the mutant rat was digested with several restriction enzymes, the probe hybridized to fragments of the same sizes as those produced from DNA of normal rats. Poly(A)+RNA from the liver of the mutant rat was found to contain an L-gulono-gamma-lactone oxidase-specific mRNA of a normal size at a comparable level to that of normal rats. An in vitro translation experiment revealed that the mRNA programmed the synthesis of an enzyme protein which had the same molecular weight as that of the translational product of the normal mRNA, although the amount synthesized was markedly reduced as compared with that synthesized with the normal mRNA. In accordance with this observation, a very low but definite degree of L-gulono-gamma-lactone oxidase activity was detected in the microsomes of the mutant rat by a newly developed, highly sensitive method.

Animals↗
PubMed1983

Biological activity of 24,24-difluoro-1 alpha, 25-dihydroxyvitamin D3 and 1 alpha, 25-dihydroxyvitamin D3-26,23-lactone in inducing differentiation of human myeloid leukemia cells.

Vitamin D compounds added to the culture medium induce differentiation of human myeloid leukemia cells (HL-60 cells) by binding to a specific cytosol receptor protein. This system provides a biologically relevant and technically simple assay to examine the relationship between molecular structure and biological activity of vitamin D compounds. Using this culture system, the biological activity of 24,24-F2-1 alpha,25(OH)2D3 and 1 alpha,25(OH)2D3-26,23-lactone was assayed. 24,24-F2-1 alpha,25(OH)2D3 was four to seven times more potent than 1 alpha,25(OH)2D3 in inducing phagocytosis and C3 rosette formation of HL-60 cells, though both compounds bound equally well to the cytosol receptor, suggesting that the defuorination at the 24-carbon position may stimulate membrane permeability of the compound. 1 alpha,25(OH)2D3-26,23-lactone, on the other hand, was only 1/200th as active as 1 alpha,25(OH)2D3. The binding affinity of the lactone for the cytosol receptor was identical with that of 1 alpha (OH)D3, suggesting that the lactone formation between the 26 and 23 positions masks the function of the 25-hydroxyl group. The binding affinity of vitamin D3 derivatives to the specific cytosol receptor of HL-60 cells was well correlated with that of intestinal cytosol protein specifically bound to 1 alpha,25(OH)2D3.

Calcitriol↗
PubMed1987

Crystal structure of muconate lactonizing enzyme at 3 A resolution.

The crystal structure of muconate lactonizing enzyme has been solved at 3 A resolution, and an unambiguous alpha-carbon backbone chain trace made. The enzyme contains three domains; the central domain is a parallel-stranded alpha-beta barrel, which has previously been reported in six other enzymes, including triose phosphate isomerase and pyruvate kinase. One novel feature of this enzyme is that its alpha-beta barrel has only seven parallel alpha-helices around the central core of eight parallel beta-strands; all other known alpha-beta barrels contain eight such helices. The N-terminal (alpha + beta) and C-terminal domains cover the cleft where the eighth helix would be. The active site of muconate lactonizing enzyme has been found by locating the manganese ion that is essential for catalytic activity, and by binding and locating an inhibitor, alpha-ketoglutarate. The active site lies in a cleft between the N-terminal and barrel domains; when the active sites of muconate lactonizing enzyme and triose phosphate isomerase are superimposed, barrel-strand 1 of triose phosphate isomerase is aligned with barrel-strand 3 of muconate lactonizing enzyme. This implies that structurally homologous active-site residues in the two enzymes are carried on different parts of the primary sequence; the ancestral gene would had to have been transposed during its evolution to the modern proteins, which seems unlikely. Therefore, these two enzymes may be related by convergent, rather than divergent, evolution.

Binding Sites↗
PubMed2006

Occurrence of N-acyl-L-homoserine lactones in extracts of some Gram-negative bacteria evaluated by gas chromatography-mass spectrometry.

Acylated homoserine lactones (AHLs) are self-generated signal molecules that mediate population density-dependent gene expression (quorum sensing) in a variety of Gram-negative bacteria. These signal molecules diffuse from bacterial cells and accumulate in the medium as a function of cell growth. In selected foods AHLs contribute to product spoilage. As different bacterial species produce AHL analogs that differ in length of the N-acyl chain, ranging from 4 to 14 carbons and in the substitution at the C-3 position of the side chain (i.e., oxo or hydroxyl group), the suitability and applicability of a gas chromatography-mass spectrometry direct method for characterizing trace amounts of AHLs was evaluated using N-heptanoyl-homoserine lactone as internal standard. Crude cell-free supernatants of bacterial cultures of Aeromonas hydrophila, Aeromonas salmonicida, Pseudomonas aeruginosa, Pseudomonas fluorescens, Yersinia enterocolitica, and Serratia liquefaciens were screened for AHL production in selected ion monitoring mode, using the prominent fragment at m/z 143. The observed profiles of distinguishable N-acyl-homoserine lactones occurring in bacterial extracts were compared and discussed. The presence of a labile 3-oxo-hexanoylhomoserine lactone was evidenced but serious difficulties arose in estimating its concentration as thermal degradation occurs during the gas chromatographic separation. Its electron impact mass spectra was, however, given and interpreted.

4-Butyrolactone↗
PubMed2004

The plant pathogen Erwinia amylovora produces acyl-homoserine lactone signal molecules in vitro and in planta.

We report for the first time the production of acyl homoserine lactones (AHLs) by Erwina amylovora, an important quarantine bacterial pathogen that causes fire blight in plants. E. amylovora produces one N-acyl homoserine lactone [a N-(3-oxo-hexanoyl)-homoserine lactone or a N-(3-hydroxy-hexanoyl)-homoserine lactone] quorum sensing signal molecule both in vitro and in planta (pear plant). Given the involvement of AHLs in plant pathogenesis, we speculate that AHL-dependent quorum sensing could play an important role in the regulation of E. amylovora virulence.

4-Butyrolactone↗
PubMed2005

Sesquiterpene lactones inhibit Yersinia invasin protein-induced IL-8 and MCP-1 production in epithelial cells.

Enteric Yersinia bacteria trigger transcription and secretion of the proinflammatory chemokines interleukin-8 (IL-8) and monocyte chemoattractant protein-1 (MCP-1) in epithelial cells. Both chemokines are controlled by NF-kappaB. The NF-kappaB-binding site in the IL-8 promoter preferentially binds Rel p65/p65 homodimers and p50/p65 heterodimers while the NF-kappaB-binding motifs of the MCP-1 promoter preferably bind p50/p65 heterodimers and p50/p50 homodimers. Sesquiterpene lactones inhibit the transcription factor NF-kappaB by alkylating the p65 subunit. In this study we investigated the inhibitory effects of sesquiterpene lactones and the NF-kappaB inhibitor SN50 on NF-kappaB p50 and p65 subunits in Yersinia-triggered IL-8 and MCP-1 production. The sesquiterpene lactones blocked Yersinia-triggered IL-8 and MCP-1 production in a dose-dependent manner. In contrast, SN50 inhibited IL-8 production at high concentrations whereas it diminished the amount of secreted MCP-1 significantly already at low concentrations. By means of electrophoretic mobility shift assays we demonstrate that sesquiterpene lactones inhibit Yersinia-triggered activation of NF-kappaB by inhibiting Rel p65, but not Rel p50. Our results also demonstrate that SN50 is useful for inhibition of nuclear translocation of the NF-kappaB p50 subunit but cannot be considered a general NF-kappaB inhibitor.

Adhesins, Bacterial↗
PubMed2004

Functional rescue of vitamin C synthesis deficiency in human cells using adenoviral-based expression of murine l-gulono-gamma-lactone oxidase.

l-Gulono-gamma-lactone oxidase (GULO) is a critical enzyme present in most mammalian species that is required for the terminal step in vitamin C biosynthesis. Primates are absolutely dependent on exogenously supplied dietary vitamin C due to inactivation of the Gulo gene by mutation over 40 million years ago. In this study, we report the cloning and expression of the murine l-gulono-gamma-lactone oxidase cDNA and gene. The cDNA (2.3 kb) encodes an open reading frame of 440 amino acids that shows high homology to the rat l-gulono-gamma-lactone oxidase (>94%). The Gulo gene is 22 kb long and contains 12 exons. The 11 introns range in size from 479 to 5641 bp. Northern blot analysis revealed high expression of Gulo transcript in the liver. To investigate whether metabolic loss of vitamin C biosynthesis in human cells can be corrected by heterologous expression of GULO, we constructed a first-generation adenoviral vector expressing the murine GULO cDNA under the transcriptional control of the murine cytomegalovirus (MCMV) early promoter. Low rescue efficiency of Gulo-expressing adenoviral constructs and reduced viral growth in HEK293 cells were observed, suggesting that overexpression of Gulo may be inhibitory to cell growth. Placement of a removable stuffer fragment flanked by lox sites between the MCMV promoter and the Gulo gene resulted in efficient vector rescue and normal viral replication in parental HEK293 cells and high-level expression of Gulo in HEK293 cells expressing Cre recombinase. Cells infected with Gulo-expressing vectors overexpressed an FAD-containing protein that corresponded in size to that predicted for recombinant GULO protein and expressed a functional enzyme as measured by the conversion of l-gulono-gamma-lactone to ascorbic acid in cell-free extracts. The cloning of the murine Gulo cDNA and the construction of Gulo-expressing adenoviral vectors are vital steps toward determining the role of vitamin C in basic metabolism and in disease.

Adenoviridae↗
PubMed1985

The unique action for bone metabolism of 1 alpha,25-(OH)2D3-26,23-lactone.

[23 (S), 25 (R)]-1 alpha,25-Dihydroxyvitamin D3-26,23-lactone [( 23 (S),25 (R)]-1 alpha,25-(OH) 2D3-26,23-lactone) increased dose-dependently alkaline phosphatase activity in osteoblastic cells, clone MC3T3-E1, in medium containing 0.1% bovine serum albumin. The maximal stimulated enzyme activity per mg protein was 1.6-fold over that of control cultures at 250 pg/ml. The metabolite also increased collagen synthesis in a dose-related fashion. On the other hand, [23 (S),25 (R)]-1 alpha,25-(OH)2D3-26,23-lactone decreased slightly but significantly 45Ca mobilization, and blocked the resorptive action of 1 alpha,25-dihydroxyvitamin D3 but not that of parathyroid hormone, in mouse calvaria in organ culture. These results indicate that [23 (S),25 (R)]-1 alpha, 25-(OH)2D3-26,23-lactone stimulates the differentiation of osteoblasts and inhibits bone resorption in vitro.

Alkaline Phosphatase↗
PubMed2002

Photoinduced electron transfer and chemical alpha-deoxygenation of D-galactono-1,4-lactone. Synthesis of 2-deoxy-D-lyxo-hexofuranosides.

Two simple procedures for the synthesis of 2-deoxy-D-lyxo-hexono-1,4-lactone are described. Reductive cleavage of a 2-O-tosyl derivative of D-galactono-1,4-lactone in the presence of sodium iodide afforded the 2-deoxy derivative. On the other hand, alpha-deoxygenation of D-galactono-1,4-lactone was easily achieved by photochemical electron transfer deoxygenation of HO-2 as the 3-(trifluoromethyl)benzoate. Methyl 2-deoxy-beta-D-lyxo-hexafuranoside ('methyl 2-deoxy-beta-D-galactofuranoside') was synthesized and tested as substrate for exo beta-D-galactofuranosidase from Penicillium fellutanum. The reaction was followed by HPAEC, showing that methyl 2-deoxy-beta-D-galactofuranoside was not hydrolyzed by incubation with the enzyme. Neither the 2-deoxy lactone, nor the 2-deoxy-beta-D-galactofuranoside acted as inhibitors of the reaction with the 4-nitrophenyl beta-D-galactofuranoside. The present and our previous results show that the hydroxyl groups at C-2, C-3 and C-6 of the galactofuranoside are essential for interaction with the exo beta-D-galactofuranosidase.

Chromatography, High Pressure Liquid↗
PubMed2000

In vivo activity of pseudoguaianolide sesquiterpene lactones in acute and chronic inflammation.

The pseudoguaianolide sesquiterpene lactones 4-alpha-O-acetyl-pseudoguaian-6beta-olide (1), hymenin (2), ambrosanolide (3), tetraneurin A (4), parthenin (5), hysterin (6) and confertdiolide (7) were evaluated for their ability to affect the inflammation responses induced by different agents. All the compounds showed activity against the 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced mouse ear edema. The ethyl phenylpropiolate (EPP)-induced mouse ear edema was inhibited by compounds 3, 5 and 7. However, when sesquiterpene-lactones were assayed on the arachidonic acid (AA)-induced mouse ear edema, none of them were active. The only sesquiterpene lactone orally active against the paw mouse edema induced by carrageenan was 7, which gave a 46% edema inhibition after 3 h. On the other hand, compounds 3, 5 and 7 reduced the serotonin-induced paw edema in mice, although compound 7 was inactive in presence of cycloheximide. In addition, the sesquiterpene lactones were assayed against the chronic inflammation induced by repeated application of TPA on mouse ear. Confertdiolide was the most active compound; it reduced the edema by 87% and had a more moderate effect against the leukocyte recruitment (36% reduction in myeloperoxidase (MPO) levels). A histological study of ear the samples treated with 7 presented no detectable morphological lesions such as those treated with dexamethasone. On the oxazolone-induced delayed type hypersensitivity (DTH) only compounds 4 and 5 were active 24 h after the challenge. Compound 5 affected polymorphonuclear leukocyte infiltration (69% reduction in MPO levels). The results suggest that the especial chemical structure and spatial conformation of confertdiolide may facilitate its anti-inflammatory effect.

Acute Disease↗
PubMed2003

Degradation of N-acylhomoserine lactones, the bacterial quorum-sensing molecules, by acylase.

Porcine kidney acylase I was shown to be able to deacylate N-acylhomoserine lactones, a family of chemicals employed by Gram-negative bacteria as quorum-sensing molecules for cell population density-dependent growth (such as biofilm formation). The enzyme transformed both N-butyryl-and N-octanoyl-L-homoserine lactones into L-homoserine. An optimal pH of 10 at 23 degrees C and an optimal temperature of 76 degrees C at pH 9 were found for the enzyme in hydrolyzing N-butyryl-homoserine lactone. At pH 9 and 23 degrees C, the enzymatic catalysis had a K(m) of 81+/-3 mM and a k(cat) of 127+/-2 nmol min(-1) per mg. The enzyme was also shown to be able to reduce the biofilm growth in an aquarium water sample. Potential physiological significance and medicinal/industrial applications of the N-acylhomoserine lactone-degrading activity of acylase are discussed.

4-Butyrolactone↗
PubMed1984

(23S)-1,23,25-Trihydroxyvitamin D3: its biologic activity and role in 1 alpha,25-dihydroxyvitamin D3 26,23-lactone biosynthesis.

(23S)-1,23,25-Trihydroxyvitamin D3 was isolated from bovine kidney homogenates incubated with 1,25-dihydroxyvitamin D3 by sequential chromatography through one Sephadex LH-20 column and three high-performance liquid chromatography systems. Ultraviolet absorption spectroscopy and mass spectrometry confirmed the structural assignment. One high-performance liquid chromatography system separated the R and S epimers of 1,23,25-trihydroxyvitamin D3 and indicated that the natural product had the S configuration. Plasma pharmacokinetic studies in rats showed that (23S)-1,23,25-trihydroxy[3H]vitamin D3 was rapidly cleared from plasma (t1/2 = 60 min). 1 alpha,25-Dihydroxy[3H]vitamin D3 26,23-lactone appeared concurrently with the disappearance of (23S)-1,23,25-trihydroxy[3H]vitamin D3. Experiments with radioinert compounds showed that 1,25-dihydroxyvitamin D3 and (23S)-1,23,25-trihydroxyvitamin D3 were efficient precursors to 1,25-dihydroxyvitamin D3 26,23-lactone both in intact and in nephrectomized rats. (25S)-1,25,26-Trihydroxyvitamin D3, however, was ineffective at raising plasma 1,25-dihydroxyvitamin D3 26,23-lactone concentrations. These results confirm the presence of extrarenal 1,25-dihydroxyvitamin D3 23(S)-hydroxylase(s) and demonstrate that C-23 hydroxylation of 1,25-dihydroxyvitamin D3 precedes C-26 hydroxylation in the formation of 1,25-dihydroxyvitamin D3 26,23-lactone. (23S)-1,23,25-Trihydroxyvitamin D3 had no intestinal calcium absorptive or bone calcium resorptive activity when dosed to vitamin D deficient rats at levels up to 500 ng. C-23 oxidation, therefore, appears to be a physiologic pathway of 1,25-(OH)2D3 metabolism and a major pathway for the deactivation of pharmacologic levels of 1,25-dihydroxyvitamin D3.

Animals↗
PubMed1990

Ganglioside GD3 lactones: polar head group mediated control of the intermolecular organization.

The individual properties and intermolecular organization of ganglioside GD3 and of two of its lactone forms (GD3Lactone I and GD3Lactone II) were studied in lipid monolayers. The formation of the first lactone ring in GD3Lactone I eliminates one negative charge and leads to a decrease of the molecular area at all surface pressures. The intermolecular dispersion energy and collapse pressure are higher in GD3Lactone I compared to those in the parent GD3. The surface potential per unit of molecular surface density and the resultant molecular dipole moment are increased in GD3Lactone I with respect to those in GD3 at comparable values of molecular area. In GD3Lactone I the molecular parameters suggest an oligosaccharide chain oriented similarly to that of GD3. On the average, this is perpendicular to the surface, and the resultant polar head-group dipole moment points away from the interface. In GD3Lactone II the negative charges are eliminated, resulting in considerably larger molecular areas than for GD3 and GD3Lactone I at all pressures. The intermolecular dispersion energy of GD3Lactone II is also greatly diminished and the collapse pressure is further increased compared to those of GD3Lactone I. However, the surface potential per unit molecular surface density and the resultant molecular dipole moment of GD3Lactone II are higher than in GD3 Lactone I at similar values of molecular areas. This is probably due to a positive polar head-group dipole moment contribution induced by the additional lactone ring in GD3Lactone II. These changes result from a distorted conformation of the oligosaccharide chain owing to the presence of fused carbohydrate rings which require a greater intermolecular spacing compared to GD3 and GD3Lactone I.

Carbohydrate Sequence↗
PubMed2005

Chemical mechanism and substrate specificity of RhlI, an acylhomoserine lactone synthase from Pseudomonas aeruginosa.

The enzyme RhlI catalyzes the formation of N-butyrylhomoserine lactone from S-adenosylmethionine and N-butyrylacyl carrier protein. N-Butyrylhomoserine lactone serves as a quorum-sensing signal molecule in Pseudomonas aeruginosa, and is implicated in the regulation of many processes involved in bacterial virulence and infectivity. The P. aeruginosa genome contains three genes encoding acyl carrier proteins. We have cloned all three genes, expressed the acyl carrier proteins, and characterized each as a substrate for RhlI. A continuous, spectrophotometric assay was developed to facilitate kinetic and mechanistic studies of RhlI. Acp1, which has not been characterized previously, was a good substrate for RhlI, with a K(m) of 7 microM; the reaction proceeded with a k(cat) value of 0.35 s(-1). AcpP, which supports fatty acid biosynthesis, was also a good substrate in the RhlI reaction, where k(cat) was 0.46 s(-1), and the K(m) for AcpP was 6 microM. The third acyl carrier protein, Acp3, was a poor substrate for RhlI, with a K(m) of 280 microM; k(cat) was 0.03 s(-1). Taken together with microarray data from the literature which show that expression of the gene encoding Acp1 is under the control of the quorum-sensing system, our data suggest that Acp1 is likely to be the substrate for RhlI in vivo. Isotope labeling studies were conducted to investigate the chemical mechanism of the RhlI-catalyzed lactonization reaction. Solvent deuterons were not incorporated into product, which implicates a direct attack mechanism in which the carboxylate oxygen of the presumptive N-butyryl-SAM intermediate attacks the methylene carbon adjacent to the sulfonium ion. Alternative mechanisms, in which N-butyrylvinylglycine is formed via elimination of methylthioadenosine, were ruled out on the basis of the observation that RhlI failed to convert authentic N-butyrylvinylglycine to N-butyryl-L-homoserine lactone.

Amino Acid Sequence↗
PubMed1989

Modification of the hydroxy lactone ring of camptothecin: inhibition of mammalian topoisomerase I and biological activity.

Several camptothecin derivatives containing a modified hydroxy lactone ring have been synthesized and evaluated for inhibition of topoisomerase I and cytotoxicity to mammalian cells. Each of the groups of the hydroxy lactone moiety, the carbonyl oxygen, the ring lactone oxygen, and the 20-hydroxy group, were shown to be critical for enzyme inhibition. For example the lactol, lactam, thiolactone, and 20-deoxy derivatives did not stabilize the covalent DNA-topoisomerase I complex. With a few exceptions, those compounds that did not inhibit topoisomerase I were not cytotoxic to mammalian cells. Two cytotoxic derivatives that did not inhibit topoisomerase I were shown to produce non-protein-associated DNA single-strand breaks and are likely to have a different mechanism of action. One of these compounds was tested for antitumor activity and was found to be inactive. The present findings, as well as other reports that the hydroxy lactone ring of camptothecin is critical for antitumor activity in vivo, correlate with the structure-activity relationships at the level of topoisomerase I and support the hypothesis that antitumor activity is related to inhibition of this target enzyme.

Animals↗
PubMed2002

1,2-dioxines as masked cis gamma-hydroxy enones and their versatility in the synthesis of highly substituted gamma-lactones.

Addition of highly stabilized ester nucleophiles to 1,2-dioxines affords good to high yields of gamma-lactones with high diastereoselectivity. Heterolytic or homolytic cleavage of the 1,2-dioxines under appropriate conditions generates the key reactive cis gamma-hydroxy enones, which ultimately afford the observed gamma-lactones. Diastereoselectivity is installed as a result of anti 1,4-addition by the ester enolate to the cis enones followed by intramolecular cyclization. The reaction is tolerant of a range of substitution patterns on the 1,2-dioxine while a broad range of esters are also accommodated. In addition to the synthesis of racemic gamma-lactones, highly enantioenriched gamma-lactones can also be synthesized when chiral cobalt(II) catalysts are employed for the initial homolytic ring-opening of the 1,2-dioxine.

Journal Article↗
PubMed2003

Stereocontrolled synthesis of bicyclic lactone derivatives via tungsten-mediated [3 + 2] cycloaddition of epoxides with a tethered alkynyl group.

In the presence of BF3*Et2O, alkynyltungsten complexes underwent [3 + 2] cycloaddition with tethered epoxides to give bicyclic -lactones efficiently. Only one diastereomeric product was formed despite the presence of three stereogenic centers. A mechanism is proposed that involves formation of a tungsten-vinylidenium species via an SN2 attack of the epoxide carbon by an alkynyltungsten group to give a tungsten-enol ether species via counterattack at the central tungsten-vinylidenium carbon by the OBF3- terminus. Most of the tungsten enol ether species were too unstable for isolation and underwent hydrolysis to give only cis-fused -bicyclic lactones. This cyclization works for both cis- and trans-epoxides and tolerates various functional groups. In the case of trans-phenyl epoxide, the reaction led to an addition product via a 6-endo attack of epoxide by the tungsten fragment. This method provides a simple enantiospecific synthesis of complex bicyclic lactones if a chiral epoxide is used in the cyclization. It is also applicable to the one-pot synthesis of bicyclic unsaturated gamma-lactones if a suitable alkynyltungsten functionality is used.

Journal Article↗