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PubMed1981

Formation of N,N-Dimethylglycine, Acetic Acid, and Butyric Acid from Betaine by Eubacterium limosum.

Two bacterial strains that grow anaerobically on betaine were isolated from enrichment cultures and identified as strains of Eubacterium limosum. In a mineral medium supplemented with yeast extract and Casitone, the doubling time of E. limosum strain 11A on betaine was 6 h at 37 degrees C. The molar growth yield amounted to 9 g of dry cell mass per mol. Betaine was fermented in accordance with the following equation: 7 betaine + 2 CO(2) --> 7 N,N-dimethylglycine + 1.5 acetate + 1.5 butyrate. E. limosum also grew on methanol and choline. The former was converted to acetate and butyrate, and the latter was converted to N,N-dimethylethanolamine, acetate, and butyrate. The conditions for the quantitative determination of N,N-dimethylglycine by capillary tube isotachophoresis have been determined.

Journal Article↗
PubMed1998

Etherolytic cleavage of 4-(2,4-dichlorophenoxy)butyric acid and 4-(4-chloro-2-methylphenoxy)butyric acid by species of Rhodococcus and Aureobacterium isolated from an alkaline environment.

Bacterial strains were isolated from the concrete rubble of a demolished herbicide production plant. The predominant feature of these strains was the etherolytic cleavage of 4-(2,4-dichlorophenoxy)butyric acid (DCPB)1) and 4-(4-chloro-2-methylphenoxy)butyric acid (MCPB) while liberating 2,4-dichlorophenol (DCP) and 4-chloro-2-methylphenol (MCP) respectively. Some of the isolates were identified by 16S rDNA sequence analysis and shown to belong to the genera Aureobacterium sp. (strain K2-17) and Rhodococcus (Rh. erythropolis K2-12). The other strains isolated clustered into these two groups according to fatty acid analysis. Etherolytic cleavage proceeded under neutral to alkaline conditions with an optimum at around pH 8.5. With Aureobacterium sp. No. K2-17, the degradation rate was zero at a pH of 6 but as much as 60% of the maximum activity was observed at pH 10.5. With Rh. erythropolis K2-12, by contrast, pronounced activity was detected at pH 6.5 while degradation was no longer observed at pH 10.5. The maximum rates of cleavage were about 1 mmol DCPB/h.g dry mass with Aureobacterium sp. No. K2-17 and about 0.6 mmol DCPB/h.g dry mass with Rh. erythropolis K2-12. DCPB and MCPB were utilized to the same extent. Substrate cleavage and product formation (DCP) proceeded at almost equal rates with Aureobacterium sp. No. K2-17 and Rh. erythropolis K2-12, which indicates that this compound was not further metabolized. Only phenoxybutyric acid compounds served as substrates; phenoxyacetic acid and phenoxypropionic acid derivatives were not utilized by these strains.

2-Methyl-4-chlorophenoxyacetic Acid↗
PubMed2005

Comparative photocatalytic study of two selected pesticide derivatives, indole-3-acetic acid and indole-3-butyric acid in aqueous suspensions of titanium dioxide.

Heterogeneous photocatalysed degradation of two selected pesticide derivatives such as indole-3-acetic acid (IAA) and indole-3-butyric acid (IBA) has been investigated in aqueous suspensions of titanium dioxide by monitoring the change in substrate concentration employing UV spectroscopic analysis technique and depletion in total organic carbon (TOC) content as a function of irradiation time. The degradation kinetics was studied under different conditions such as pH, types of TiO2) substrate and catalyst concentration, and in the presence of electron acceptor such as hydrogen peroxide (H2O2) besides molecular oxygen. The degradation rates were found to be strongly influenced by all the above parameters. The photocatalyst Degussa P25 showed comparatively highest photocatalytics. The pesticide derivative, indole-3-acetic acid was found to degrade slightly faster than indole-3-butyric acid.

Butyric Acid↗
PubMed1996

Esterase inhibitors diminish the modulation of gene expression by butyric acid derivative, pivaloyloxymethyl butyrate (AN-9).

Pivaloyloxymethyl butyrate (AN-9) belongs to the family of acyloxyalkyl ester prodrugs of carboxylic acids which undergo intracellular hydrolysis to yield butyric acid (BA). We have previously shown that AN-9 and BA reduce the level of c-myc and enhance c-jun transcripts in HL-60 cells, and that the differentiation of these cells, induced by AN-9, is dependent on the presence of intracellular esterases. In this study we show that esterase inhibitors abolish the changes induced by AN-9 on c-myc and c-jun expression. In contrast, esterase inhibitors do not change the effects of BA on c-myc or c-jun. Interestingly, these inhibitors affect the modulation induced by both AN-9 and BA on the retinoblastoma tumor suppressor gene. These data suggest that AN-9 is indeed a prodrug of BA and that prior intracellular hydrolysis by esterases is material for AN-9 activity.

Aniline Compounds↗
PubMed2005

Hyaluronic acid butyric esters in cancer therapy.

In this review we focus on a promising novel histone deacetylase (HDAC) inhibitor (HA-But) obtained by the esterification of butyric acid (BA), the smallest HDAC inhibitor, with hyaluronic acid (HA), the main constituent of the extracellular matrix which selectively recognizes a transmembrane receptor (CD44) overexpressed in most primary cancers and associated with tumor progression. In vitro, HA-But has proved to be 10-fold more effective than BA in inhibiting the proliferation of a panel of human cancer cell lines, representative of the most common human cancers, and, similar to BA, to regulate the expression of some cell cycle-related proteins, to induce growth arrest in the G1/G0 phase of the cell cycle and to increase histone acetylation. In vivo, HA-But treatment has demonstrated a marked potency in inhibiting primary tumor growth and lung metastases formation from murine Lewis lung carcinoma (LL3) as well as liver metastases formation from intrasplenic implantation of LL3 or B16-F10 murine melanoma cells. In particular, the effect of s.c. and i.p. treatment with HA-But on liver metastases resulted, respectively, in 87 and 100% metastases-free animals, and in a significant prolongation of the survival time compared to the control groups. The results suggest that the presence of the HA backbone does not interfere with the biological activity of butyric residues and that HA-But could represent a promising cell-targetable antineoplastic agent for the treatment of primary and metastatic tumors.

Animals↗
PubMed2001

Butanol effects on gamma-amino butyric acid concentration-responses in human alpha1beta2gamma2L gamma-amino butyric acid type A receptors with a mutation at alpha1S270.

Alcohol enhancement of gamma-amino butyric acid type A receptor (GABA(A)R) gating at low GABA is reduced by a serine-to-isoleucine mutation at residue alphaS270, suggesting that alphaS270 forms an enhancement site. However, whether the alphaS270I mutation strengthens alcohol inhibition of GABA(A)Rs remains unexplored. Furthermore, alphaS270 mutations have not been studied in the most prevalent form of mammalian GABA(A)Rs consisting of alpha1, beta2, and gamma2 subunits. In voltage-clamped Xenopus oocytes expressing recombinant alpha1beta2gamma2L GABA(A)Rs, electrophysiological analysis of GABA concentration-responses demonstrates that the alpha1(S270I) mutation increases apparent GABA affinity and significantly reduces the Hill coefficient of GABA(A)R activation. Butanol-induced leftward-shifts in GABA concentration-responses for both wild-type alpha1beta2gamma2L and alpha1(S270I)beta2gamma2L GABA(A)Rs are equal. At high GABA, butanol neither enhances nor inhibits alpha1(S270I)beta2gamma2L responses. Thus, in the dominant mammalian GABA(A)R isoform, the alphaS270I mutation affects neither enhancement nor inhibition by butanol, but alters the gating mechanism by reducing cooperativity, producing an apparent reduction in alcohol enhancement at low GABA.

1-Butanol↗
PubMed1984

The actions of the hydroxamic acid of gamma amino butyric acid on the isolated rabbit atria and jejunum.

The hydroxamic acid of gamma amino butyric acid (HAGABA) has been prepared and was studied in the isolated rabbit atria and jejunum. HAGABA did not interfere with the spontaneous contractile rhythm and frequency of the isolated atria except in large mM concentrations in the bath. HAGABA displayed a biphasic effect in the isolated jejunum, which manifested itself first as stimulation followed by inhibition with an increasing concentration in the bath. Bicuculline and HAGABA did not antagonize each other in the enteric nervous system, but rather an augmentation was observed.

Acetylcholine↗
PubMed1991

Effect of Exogenous Indole-3-Acetic Acid and Indole-3-Butyric Acid on Internal Levels of the Respective Auxins and Their Conjugation with Aspartic Acid during Adventitious Root Formation in Pea Cuttings.

The influence of exogenous indole-3-acetic acid (IAA) and indole-3-butyric acid (IBA) on the internal levels of these auxins was studied during the first 4 days of adventitious root formation in cuttings of Pisum sativum L. The quantitations were done by high performance liquid chromatography with spectrofluorometric detection. IBA, identified by combined gas chromatography-mass spectrometry (GC-MS), was found to naturally occur in this plant material. The root inducing ability of exogenous IBA was superior to that of IAA. The IAA level in the tissue increased considerably on the first day after application of IAA, but rapidly decreased again, returning to a level twice the control by day 3. The predominant metabolic route was conjugation with aspartic acid, as reflected by the increase in the level of indole-3-acetylaspartic acid. The IBA treatment resulted in increases in the levels of IBA, IAA, and indole-3-acetylaspartic acid. The IAA content rapidly returned to control levels, whereas the IBA level remained high throughout the experimental period. High amounts of indole-3-butyrylaspartic acid were found in the tissue after feeding with IBA. The identity of the conjugate was confirmed by (1)H-nuclear magnetic resonance and GC-MS. IBA was much more stable in solution than IAA. No IAA was detected after 48 hours, whereas 70% IBA was still recovered after this time. The relatively higher root inducing ability of IBA is ascribed to the fact that its level remained elevated longer than that of IAA, even though IBA was metabolized in the tissue. Adventitious root formation is discussed on the basis of these findings.

Journal Article↗
PubMed2005

Effect of butyric acid on the performance and carcass yield of broiler chickens.

Short-chain fatty acids such as butyrate are considered potential alternatives to antibiotic growth promoters. The efficacy of butyric acid on performance and carcass characteristics of broiler chickens was tested in two studies. The effect of dietary butyrate on the ability to withstand coccidial oocyte challenge also was investigated. In experiment 1, male broiler chickens were fed diets supplemented with 0 or 11 ppm virginiamycin or 0.2 or 0.4% butyric acid (as mono-, di-, and triglyceride). In experiment 2, broilers were fed bacitracin methylene disalicylate or 0.1 or 0.2% butyric acid. In another trial, birds vaccinated against coccidiosis were challenged with oocytes at 21 d and examined 6 d later. In experiment 1, diet treatments had no effect on body weight gain. Feed intake of the birds fed 0.4% butyric acid was decreased (P < 0.01) compared with birds fed the nonmedicated diet during the starter period, whereas birds fed 0.2% butyric acid had similar feed intake to the control birds. In experiment 2, diet treatments did not affect the performance of broiler chicks while carcass weight and breast meat yield increased (P < 0.01) in birds fed 0.2% butyric acid. With oocyte challenge, birds that had received butyric acid before challenge showed higher growth rate following the challenge compared with birds that received nonmedicated feed. Bacitracin decreased (P < 0.05%) duodenal villi crypt depth, whereas villus length was similar in birds fed butyric acid or the nonmedicated control diet. These results show that 0.2% butyric acid can help to maintain the performance and carcass quality of broilers, especially in vaccinated birds challenged with coccidiosis.

Animals↗
PubMed2002

Quantitation of colonic luminal synthesis of butyric acid in piglets.

OBJECTIVES: Butyric acid, synthesized via bacterial fermentation in colonic lumen, may play an important role in the nutrition of the colonic mucosa. Since disaccharides, especially lactose, are the principal dietary carbohydrates during infancy, it is important to determine if their fermentation is associated with butyric acid synthesis. The objective of this paper is to describe a newly developed stable isotope method for quantifying butyric acid synthesis in the colonic lumen and to demonstrate its application during cecal infusions of lactose and lactulose in piglets. METHODS: Nine piglets aged 21 to 30 days were studied during acute anesthesia. The C enrichment of butyric acid was monitored in the portal vein before and during a 120 minutes cecal infusion of [1- C]-butyric acid and either unlabeled lactose (N = 4) or lactulose (N = 5). RESULTS: The luminal synthesis of BA (micromol x kg x min ) (Mean +/- S.D.) was respectively 1.5 +/- 0.9 and 1.2 +/- 0.6 during lactulose and lactose infusion. CONCLUSIONS: This study provides new quantitative data on in vivo butyric acid production in the mammalian colon.

Animals↗
PubMed1991

Pharmacokinetics of butyric acid derivative with xylitol.

The short chain fatty acids, especially butyric acid salts have interesting biological properties. In some cases, transformed cells can recover a normal phenotype and in animal, butyrate salts increase antitumor resistance. Butyrate may be considered as possibly useful for antitumor therapy. But these products exhibit two essential disadvantages which restrict their clinical use in man: high concentrations required to achieve therapeutic effects and rapid excretion with short half life. In order to optimize the clinical use of butyrate, we studied a n-butyric acid ester obtained with xylitol selected for its physiological and metabolic inertia. Structure determination of tributyryl xylitol was carried out by mass and NMR spectrometry (MW = 344). The low toxicity and the antitumor effects of this ester, especially in association with Corynebacterium parvum and interferon, confirm its therapeutic interest. The slow excretion of this prodrug should make butyrate clinical use easier by preventing extensive systemic metabolism and metabolic side-effects due to cations of butyrate salts.

Animals↗