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Expedient synthesis of threo-beta-hydroxy-alpha-amino acid derivatives: phenylalanine, tyrosine, histidine, and tryptophan.

An expedient synthesis of enantiomerically pure threo-beta-hydroxy-alpha-amino acid derivatives of phenylalanine, tyrosine, histidine, and tryptophan is described. The NBS-mediated radical bromination of the N,N-di-tert-butoxycarbonyl protected alpha-amino acids and subsequent treatment with silver nitrate in acetone provided the trans-oxazolidinones predominantly. Cesium carbonate catalyzed hydrolysis then generated the beta-hydroxy amino acid derivatives in excellent overall yield.

Amino Acids↗

Intranephron distribution of cysteine S-conjugate beta-lyase activity and its implication for hexachloro-1,3-butadiene-induced nephrotoxicity in rats.

The intranephron distribution of two major cysteine S-conjugate beta-lyases was determined in order to clarify the role of these enzymes in promoting the nephrotoxicity associated with certain halogenated xenobiotics. Various nephron segments [i.e., glomerulus, early, middle, and terminal portions of the proximal tubule (S1, S2, and S3 respectively), the thick ascending limb, the distal tubule, and the collecting tubule] were isolated by microdissection from collagenase-treated rat kidneys. Each segment was dissected in Hanks' solution, solubilized with Triton X-100, and applied to a micropolyacrylamide gel constructed with a continuous gradient. The gels were subjected to electrophoresis and then incubated in the dark in a solution containing S-(1,2 dichlorovinyl)-L-cysteine (DCVC), a sodium alpha-keto-gamma-methiolbutyrate, phenazine methosulfate, and nitro-blue tetrazolium. The position of cysteine S-conjugate beta-lyase- and L-amino acid oxidase activities in the gels was revealed by the presence of blue formazen dye bands. The relative intensities of the bands were determined by optical scanning with a microdensitometer. Three bands were detected: band I (M(r) approximately 330,000) corresponds to a recently described high M(r) cysteine S-conjugate beta-lyase whereas band III (M(r) approximately 90,000) corresponds to a lower M(r) cysteine S-conjugate beta-lyase (identical to cytosolic glutamine transaminase K). Band II (M(r) approximately 240,000) corresponds to L-amino acid oxidase (a unique activity of the B isoform of rat kidney L-hydroxy acid oxidase). beta-lyase activity with DCVC as substrates was detected in the S1, S2, and S3 segments of the nephron but not in other regions of the kidney. The activity was in the order: S2 = S3 > S1. In another series of experiments, rats were killed 24 h after treatment with hexachloro- 1,3-butadiene (HCBD). In whole kidney homogenates the relative intensity of band III (per 22.2 micrograms tissue wet weight) after a 30 min incubation was induced significantly (by 50%), but the relative intensities of the other two bands were unchanged. On the other hand, in proximal tubules isolated from HCBD-treated rats the relative intensities (per 5 mm of nephron) of peak I of S2, peak II of S3, and peak III of S3 were significantly reduced by 28, 33, and 72%, respectively. These findings suggest that the low M(r) beta-lyase is induced by HCBD and that impaired cell function in the segments (especially S3) results in proteins leaking out of the target cells. To examine the relationship between the nephrotoxic effect of HCBD and cysteine S-conjugate beta-lyase activity, the intracellular ATP:protein ratio was quantitated in each nephron segment and in whole kidney homogenates. In HCBD-treated rats the ATP:protein ratio of the S1, S2, and S3 segments was unchanged, decreased by approximately 50%, and increased by approximately 30% respectively. In the kidney homogenates of HCBD-treated rats the ATP content was decreased by 32%. However, the loss of ATP was significantly less when the rats were pretreated with aminooxyacetate (a general inhibitor of pyridoxal 5'-phosphate-dependent enzymes, including beta-lyase) 1 h before HCBD administration. The results strongly suggest that HCBD is converted to toxic metabolites within the kidney and that this process leads to metabolic derangement and reduction of ATP in susceptible kidney cells.

Adenosine Triphosphate↗

Investigating the stereochemistry of binding to HIV-1 protease with inhibitors containing isomers of 4-amino-3-hydroxy-5-phenylpentanoic acid.

A series of inhibitors containing all possible isomers of 4-amino-3-hydroxy-5-phenylpentanoic acid was synthesized and tested for inhibition of HIV-1 protease. Incorporation of the (3S,4S) isomer of the t-butyloxycarbonyl protected amino acid into the sequence Glu-Phe resulted in a potent inhibitor of HIV-1 protease (Ki = 63 nM). This inhibitor is at least 47-times more potent than the inhibitors containing other isomers of 4-amino-3-hydroxy-5-phenylpentanoic acid, indicating that the (3S,4S) isomer is the preferred isomer for binding to HIV-1 protease.

Amino Acid Sequence↗

Apparent failure of 2-hydroxy-3-naphthoic acid hydrazide to block the periodic acid-Schiff reactivity of sialic acids. Implications for the PANFOPAS method.

Histochemical studies of the mechanism of staining of the periodic acid/2,-hydroxy-3-naphthoic acid hydrazide/Fast Black B/saponification/periodic acid-Schiff (PANFOPAS) method indicate that while 2-hydroxy-3-naphthoic acid hydrazide blocks the periodate engendered Schiff reactivity of vicinal diols unassociated with anionic groups, it fails to block such reactivity in sialic acid residues. It is suggested, therefore, that the positive Schiff staining observed following application of the PANFOPAS method to colonic epithelial mucins may be due to sialic acids without side chain substituents (or which are substituted at C7 or C9) in addition to sialic acids substituted at C8 (or which are di- or trisubstituted). Consequently the PANFOPAS method cannot be used to study the side chain substitution pattern of the sialic acids of epithelial mucins.

Animals↗

Glycolic acid treatment increases type I collagen mRNA and hyaluronic acid content of human skin.

BACKGROUND: Chronic solar irradiation results in both morphologic and functional changes in affected skin. alpha-hydroxy acids, such as glycolic acid, have been shown to improve photodamaged skin. OBJECTIVE: To investigate alterations in collagen gene induction and epidermal and dermal hyaluronic acid production as a result of administered glycolic acid. METHODS: In this study we compared collagen gene expression from skin biopsy specimens, and epidermal and dermal hyaluronic acid immunohistochemical staining between glycolic acid-treated and vehicle-treated skin. Forearm skin was treated with 20% glycolic acid lotion or a lotion vehicle control twice a day for 3 months. RESULTS: Epidermal and dermal hyaluronic acid and collagen gene expression were all increased in glycolic acid-treated skin as compared to vehicle-treated controls. CONCLUSION: Our data suggest that epidermal and dermal remodeling of the extracellular matrix results from glycolic acid treatment. Longer treatment intervals may result in collagen deposition as suggested by the measured increase in mRNA.

Aged↗

3-Hydroxy-3-methylglutaric acid (HMGA) reduces dietary cholesterol induction of saturated bile in hamster.

3-Hydroxy-3-methylglutaric acid (HMGA) is a competitive inhibitor of 3-hydroxy-3-methylglutaryl-CoA reductase (HMGCoAR) and strongly reduces cholesterol biosynthesis both in vitro and in vivo. Since the effects of this compound on biliary lipid composition are hitherto unknown, we have investigated whether it prevents dietary cholesterol induction of saturated bile in the hamster. Female Golden Syrian hamsters have been divided into four groups and treated for 10 weeks as follows: I) Standard diet, containing 0.8 mg cholesterol/g food; II) Standard diet plus HMGA (100 mg/kg b.w./day per os); III) Lithogenic diet containing 2.4 mg cholesterol/g food; IV) Lithogenic diet plus HMGA as above. The results indicate that HMGA is effective in reducing both bile cholesterol supersaturation and hypercholesterolemia. Inhibition of hepatic cholesterogenesis at the level of mevalonate synthesis by HMGCoAR and reduction of intestinal cholesterol absorption may be responsible for these effects.

Animals↗

Histochemistry of reactive oxygen-species (ROS)-generating oxidases in cutaneous and mucous epithelia of laboratory rodents with special reference to xanthine oxidase.

Cutaneous and mucous epithelia of various organs of laboratory rodents were analysed histochemically for reactive oxygen species (ROS)-generating oxidases using cerium methods. High activities of xanthine oxidase and also superoxide dismutase were present in orthokeratotic stratified squamous epithelia of skin, lips, esophagus and forestomach and parakeratotic keratinizing stratified epithelia of vagina, tongue and penis. Moreover, activity was found in simple epithelium of the uterus and intestine of rats, mice and guinea-pigs. Moderate activities of monoamine oxidase and D-amino acid oxidase were only seen in enterocytes of large and small intestine, whereas alpha-hydroxy acid oxidase could not be detected at all. With the use of specific inhibitors for superoxide anions-producing xanthine oxidase and H2O2-generating superoxide dismutase it was shown that epithelial cells of all studied external and internal surface epithelia contain a highly effective xanthine oxidase-superoxide dismutase system. It is hypothesized that this system might have a general microbicidal function and might play a special role in tumor promotion of the skin.

Alcohol Oxidoreductases↗

Characterization of glucosylceramide from plasma membranes of plant root cells.

Plasma membranes of oat root cells were isolated from intracellular membranes by subfractionation of the microsomal fraction using an aqueous polymer two-phase system. The plasma membranes originated from oat plants which were acclimated to dehydration by exposure to a repeated water-deficit stress program. Glucosylceramides was a major component of the plasma membrane lipids and amounted to 9% of the lipid of control plants and 5% of the lipid of acclimated plants. Structural analysis using FAB-MS showed only one type of glucosylceramides. The constituent monosaccharide was exclusively glucose and the sphingosine base was 4,8-sphingadienine. The fatty acid composition was determined to 24:1-OH, with only trace levels of non-hydroxy acids. The decrease in the level of glucosylceramides during acclimation to dehydration was accompanied by a corresponding decrease in phospholipids and increase in free sterols.

Cell Membrane↗

Stereospecific formation of (24E)-3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholest-24-en-26-oic acid and (24R,25S)-3 alpha,7 alpha,12 alpha,24-tetrahydroxy-5 beta-cholestan-26-oic acid from either (25R)- or (25S)-3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestan-26-oic acid by rat liver homogenate.

Studies of the stereochemistry of the intermediates, 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholest-24-en-26-oic acid and 3 alpha,7 alpha,12 alpha,24-tetrahydroxy-5 beta-cholestan-26-oic acid, in the biosynthetic sequence between 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestan-26-oic acid and cholic acid have been undertaken. (25R)- or (25S)-3 alpha,7 alpha, 12 alpha-Trihydroxy-5 beta-cholestan-26-oic acid was incubated with rat liver homogenates. The reaction products were converted to p-bromophenacyl ester derivatives and the esters were analyzed by high-performance liquid chromatography. By comparison with authentic samples of two (24E)- and (24Z)-isomers of the alpha, beta-unsaturated acid and of four isomers at C-24 and C-25 of the beta-hydroxy acid, (24E)-3 alpha,7 alpha, 12 alpha-trihydroxy-5 beta-cholestan-26-oic acid and (24R,25S)-3 alpha,7 alpha,12 alpha,24-tetrahydroxy-5 beta-cholestan-26-oic acid were found to be formed from either (25R)- or (25S)-3 alpha,7 alpha, 12 alpha-trihydroxy-5 beta-cholestan-26-oic acid. No formation of the (24Z)-isomer of the trihydroxycholestenoic acid or the other three isomers of the tetrahydroxycholestanoic acid was detected. The findings are discussed in relation to the assumed pathway for side chain cleavage in cholic acid biosynthesis.

Animals↗

Domino syntheses of bioactive tetronic and tetramic acids.

Natural products containing tetronic acid or tetramic acid moieties continue to attract the interest of chemists, biologists, and physicians due to their challenging structures and to the wide range of biological activities they display. This review portrays the structural varieties of tetronic and tetramic acids and the spectrum of possible therapeutically relevant effects in man for exemplary derivatives. Their biosynthetic origin from alpha-amino and alpha-hydroxy acids is briefly discussed as is the relationship between their structures and their modes of interaction with biochemical effectors such as metal cations or enzymes. A short overview of laboratory syntheses of the heterocyclic core structures of tetramic and tetronic acids is provided with an emphasis on those emulating the biosynthesis. A synthesis from the alpha-amino or alpha-hydroxy esters and the cumulated phosphorus ylide Ph(3)PCCO based upon a domino addition-intra-Wittig alkenation sequence is presented with applications to the preparation of the antibiotics reutericyclin and tenuazonic acid, the cytotoxic melophlin B, and the enzyme inhibitor RK-682. Procedural advantages of immobilizing either starting component by attaching it to a resin and its exploitation in the parallel synthesis of libraries of potential drug candidates are described. The basic domino reaction can even be extended by further C-C bond forming steps when starting from suitable alpha-hydroxy or alpha-amino allyl esters. Depending on the chosen reaction conditions, bioactive intermediates of formally three to seven step long cascades can be obtained. Among them, herbicidal 3-alkyltetronic acids and lactone endoperoxides with antiplasmodial activity exceeding that of the natural antimalarial lead artemisinin. Hence, this domino reaction gives access to diversely functionalized derivatives of tetronic and tetramic acids. As it can also be ported to solid phase, it is ideally suited for parallel and combinatorial processing. Future developments might include running such domino sequences in continuous mode in arrays of "labs on microchips".

Biological Products↗

The determination in human plasma of 1-hydroxy-2-naphthoic acid following administration of salmeterol xinafoate.

The clinical development of salmeterol xinafoate, the 1-hydroxy-2-naphthoic acid salt of salmeterol, a potent long acting beta 2 agonist bronchodilator, has required the development of a method for the determination of 1-hydroxy-2-naphthoic acid (HNA), in human plasma. A sensitive, accurate and precise method was, therefore, required to enable the pharmacokinetic profile to be established. HNA was determined in human plasma using a semi-automated procedure with solid-phase extraction using an automated analytical sample processor (AASP) and high-performance liquid chromatography (HPLC) with fluorescence detection. The method was sensitive to 10 ng ml-1. The method is specific for HNA with respect to endogenous plasma components and has been shown to be robust, accurate and precise. Over four independent assay runs, the relative standard deviations (RSD) of the quality control samples (QC) were 1.6, 2.4 and 5.5% at 180, 100 and 40 ng ml-1, respectively. A pharmacokinetic profile of HNA in man has been established from a single dose kinetic study in healthy volunteers following an oral dose of 500 micrograms salmeterol xinafoate, equivalent to 225 micrograms HNA. Maximum plasma concentrations attained at 1 h after dosing ranged between 35.3 and 66.8 ng ml-1 and were within the calibration range of the assay.

Administration, Oral↗

Lipid composition and fluidity of plasma membranes isolated from corn (Zea mays L.) roots.

Although the results of lipid analyses from several plant species have been available for many years a complete characterization of the corn root plasma membrane is still lacking. The present study provides a detailed analysis of individual lipids and a characterization of the membrane fluidity of corn (Zea mays L.) root plasma membranes isolated by phase-partitioning. Phospholipids (43.9 mol%), sterols (40.8 mol%), and sphingolipids in the form of glucocerebroside (6.8 mol%) constitute the major lipid classes. Stigmasterol (19.8 mol%), campesterol (13.0 mol%), phosphatidylcholine 15.8 mol%), and phosphatidylethanolamine (14.2 mol%) represent the most ubiquitous individual lipids. Hydroxy fatty acids make up 80.9 mol% and very long chain fatty acids are almost 78% of fatty acids in glucocerebroside. Hydroxy arachidic acid (20:0 h) and hydroxy lignoceric acid (24:0 h) are most prominent and glucocerebroside from corn root plasma membranes contains virtually no unsaturated fatty acids. Among the phospholipids only phosphatidylserine displayed a high proportion of very long chain fatty acids (e.g., behenic and lignoceric acid). Membrane fluidity was estimated by fluorescence anisotropy. Due to the high sterol content the plasma membrane of corn roots is relatively rigid.

Cell Fractionation↗

Bioconversion of 3beta-hydroxy-5-cholenoic acid into chenodeoxycholic acid by rat brain enzyme systems.

We have previously demonstrated that the rat brain contains three unconjugated bile acids, and chenodeoxycholic acid (CDCA) is the most abundantly present in a tight protein binding form. The ratio of CDCA to the other acids in rat brain tissue was significantly higher than the ratio in the peripheral blood, indicating a contribution from either a specific uptake mechanism or a biosynthetic pathway for CDCA in rat brain. In this study, we have demonstrated the existence of an enzymatic activity that converts 3beta-hydroxy-5-cholenoic acid into CDCA in rat brain tissue. To distinguish marked compounds from endogenous related compounds, 18O-labeled 3beta-hydroxy-5-cholenoic acid, 3beta,7alpha-dihydroxy-5-cholenoic acid, and 7alpha-hydroxy-3-oxo-4-cholenoic acid were synthesized as substrates for in vitro incubation studies. The results clearly suggest that 3beta-hydroxy-5-cholenoic acid was converted to 3beta,7alpha-dihydroxy-5-cholenoic acid by microsomal enzymes. The 7alpha-hydroxy-3-oxo-4-cholenoic acid was produced from 3beta,7alpha-dihydroxy-5-cholenoic acid by the action of microsomal enzymes, and Delta4-3-oxo acid was converted to CDCA by cytosolic enzymes. These findings indicate the presence of an enzymatic activity that converts 3beta-hydroxy-5-cholenoic acid into CDCA in rat brain tissue. Furthermore, this synthetic pathway for CDCA may relate to the function of 24S-hydroxycholesterol, which plays an important role in cholesterol homeostasis in the body.

Animals↗

Serum and liver lipid responses to 3-hydroxy-3-methylglutaric acid in rats on different carbohydrate diets.

Groups of male adult albino rats were administered 3-hydroxy-3-methylglutaric acid (HMG) intraperitoneally along with six diets differing only in the type of carbohydrate used. Groups not treated with HMG served as controls. HMG showed a significant cholesterol- and tri-glyceride-lowering effect in the whole serum, serum beta-lipoproteins, and liver of animals on all types of dietary carbohydrates. The effect was more marked in glucose, fructose, sucrose, and lactose. The phospholipid levels in whole serum, serum beta-lipoproteins, as well as in liver were also significantly lowered on all types of carbohydrates except dextrin and starch fed animals, where it had no effect on liver levels. The lipid-lowering effect of HMG seems to be independent of the type of carbohydrate in diet.

Animals↗

On the structure of calonyctin A, a plant growth regulator.

The plant growth regulator calonyctin A, isolated from the dried leaves of Calonyction aculeatum L. House (Yue-Guang-Hua), was separated into two pure components by high performance liquid chromatography. By use of mass spectrometry based on various ionization techniques, one- and two-dimensional NMR spectroscopy, IR spectrometry, and chemical methods the molecular structures of the two homologous glycosides were determined. Each molecule contains two hydroxy fatty acid residues and four 6-deoxyhexose units. The fatty acids are 3-hydroxy-2-methylbutanoic acid and 11-hydroxytetradecanoic acid or 11-hydroxyhexadecanoic acid. The 6-deoxyhexose residues (three of quinovose and one of rhamnose) comprise a tetrasaccharide having the following structure: [formula: see text] The long-chain hydroxy acid is linked glycosidically through its O-11 to Qui D and esterified to O-2 of Qui C, forming a macrocyclic lactone. The 3-hydroxy-2-methylbutanoic acid is ester-linked to O-3 of Qui C.

Carbohydrate Conformation↗

Biosynthesis of lipids by bovine meibomian glands.

Isolated bovine meibomian glands incorporated exogenous [1-14C]acetate into lipids. Thin layer chromatographic analysis of the lipids showed that wax esters and sterol esters contained 61% of the total label. Radio gas liquid chromatographic analysis of the acid and alcohol moieties of both ester fractions showed the label was distributed equally between the two portions of the ester in both cases. Cholesterol and 5-alpha-cholest-7-en-3 beta-ol were the major labeled sterols, and anteiso-C25, anteiso-C27 and anteiso-C23 were the most highly labeled alcohols. The major labeled fatty acids in the wax esters were anteiso-C15, n-C16, anteiso-C17 and n-C18:1, whereas anteiso-C25 and anteiso-C27 were the major labeled acids in the sterol esters. The diester region with 6% of the total label contained labeled fatty acids and fatty alcohols each with anteiso-C25 as the major component and omega-hydroxy acids in which n-C32:1 was the major labeled component. The triglyceride fraction which contained 8% of the total lipids was composed of labeled fatty acids similar to those found in both sterol and wax ester fractions. Chromatographic analyses of the labeled lipids derived from exogenous labeled isoleucine showed that anteiso-branched products were preferentially labeled. The labeled triglyceride fraction derived from [U-14C] isoleucine also contained esterified C15, C13, C11, C9, C7 and possibly shorter anteiso-branched acids.

Acetates↗

Addition of oxidizing or reducing agents to the reaction medium influences amino acid conversion to aroma compounds by Lactococcus lactis.

AIMS: The aim of this research was to investigate the impact of extracellular redox potential (Eh) on amino acid conversion to aroma compounds by Lactococcus lactis that is commonly used as a starter in the cheese industry. METHODS AND RESULTS: The study was realized in vitro by incubating resting cells of L. lactis in reaction media in which E(h) was modified by the addition of oxidizing or reducing agents. Oxidative condition (+300 mV) favoured the production of aldehydes and volatile sulfur compounds responsible for malty, floral, fruity, almond and cabbage aroma. This production was mainly the result of a chemical oxidation of the alpha-keto acids produced by amino acid transamination. In contrast, reducing condition (-200 mV) stimulated the production of carboxylic acids such as phenylacetic, methylthiopropionic and isovaleric acids, which contribute to the very-ripened-cheese aroma as well as the production of hydroxy acids. CONCLUSIONS: Eh of the medium highly influences the nature of aroma compounds produced from amino acid catabolism by the resting cells of L. lactis. SIGNIFICANCE AND IMPACT OF THE STUDY: E(h) is a parameter that is not controlled during cheese production. Its control throughout cheese making and ripening could permit control of aroma formation in cheese.

Amino Acids↗

Degradation of hydrocarbons by members of the genus Candida 3. Oxidative intermediates from 1-hexadecene and 1-heptadecene by Candida lipolytica.

Candida lipolytica (Phaff) was grown in a mineral-salts medium amended with either 1-hexadecene or 1-heptadecene as substrate. Intermediates of the same chain length as the substrate were isolated and identified by various analytical procedures. The following intermediates of 16 and 17 carbon atoms were identified: omega-unsaturated acids, omega-unsaturated primary and secondary alcohols, 1,2-epoxides, 1,2-diols, and 2-hydroxy acids. Based on the chemical structure of these compounds, three oxidative mechanisms are proposed for the degradation of long-chain 1-alkenes by this yeast: (i) methyl-group oxidation, (ii) double-bond oxidation, and (iii) subterminal oxidation.

Acids↗