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PubMed1999

alpha-oxidation of fatty acids in higher plants. Identification of a pathogen-inducible oxygenase (piox) as an alpha-dioxygenase and biosynthesis of 2-hydroperoxylinolenic acid.

A pathogen-inducible oxygenase in tobacco leaves and a homologous enzyme from Arabidopsis were recently characterized (Sanz, A., Moreno, J. I., and Castresana, C. (1998) Plant Cell 10, 1523-1537). Linolenic acid incubated at 23 degrees C with preparations containing the recombinant enzymes underwent alpha-oxidation with the formation of a chain-shortened aldehyde, i.e., 8(Z),11(Z), 14(Z)-heptadecatrienal (83%), an alpha-hydroxy acid, 2(R)-hydroxy-9(Z),12(Z),15(Z)-octadecatrienoic acid (15%), and a chain-shortened fatty acid, 8(Z),11(Z),14(Z)-heptadecatrienoic acid (2%). When incubations were performed at 0 degrees C, 2(R)-hydroperoxy-9(Z),12(Z),15(Z)-octadecatrienoic acid was obtained as the main product. An intermediary role of 2(R)-hydroperoxy-9(Z), 12(Z),15(Z)-octadecatrienoic acid in alpha-oxidation was demonstrated by re-incubation experiments, in which the hydroperoxide was converted into the same alpha-oxidation products as those formed from linolenic acid. 2(R)-Hydroperoxy-9(Z),12(Z), 15(Z)-octadecatrienoic acid was chemically unstable and had a half-life time in buffer of about 30 min at 23 degrees C. Extracts of cells expressing the recombinant oxygenases accelerated breakdown of the hydroperoxide (half-life time, about 3 min at 23 degrees C), however, this was not attributable to the recombinant enzymes since the same rate of hydroperoxide degradation was observed in the presence of control cells not expressing the enzymes. No significant discrimination between enantiomers was observed in the degradation of 2(R,S)-hydroperoxy-9(Z)-octadecenoic acid in the presence of recombinant oxygenases. A previously studied system for alpha-oxidation in cucumber was re-examined using the newly developed techniques and was found to catalyze the same conversions as those observed with the recombinant enzymes, i.e. enzymatic alpha-dioxygenation of fatty acids into 2(R)-hydroperoxides and a first order, non-stereoselective degradation of hydroperoxides into alpha-oxidation products. It was concluded that the recombinant enzymes from tobacco and Arabidopsis were both alpha-dioxygenases, and that members of this new class of enzymes catalyze the first step of alpha-oxidation in plant tissue.

Aldehydes↗

PubMed1990

Facial wrinkles. Prevention and nonsurgical correction.

There is no way to age without getting wrinkles. However, patients can be taught how to retard the onset of wrinkles by avoiding unprotected sun exposure, unnecessary facial movements, and certain sleeping positions. Relatively simple non-surgical techniques are available for correction of wrinkles. Small wrinkles can be treated with exfoliation, topical tretinoin (Retin-A), or topical alpha hydroxy acids. Large wrinkles can be improved with implantation of bovine collagen, silicone, or fat extracted from the abdomen or thigh of the patient. Each method is effective when used for the correct indications.

Adult↗

PubMed1997

Differentiation of Malassezia species: selectivity of cremophor EL, castor oil and ricinoleic acid for M. furfur.

In recent years, the genus Malassezia has been reclassified based on molecular data. In addition to M. furfur, M. pachydermatis and M. sympodialis, four new species, M. globosa, M. obtusa, M. restricta and M. slooffiiae, have been described. However, apart from their lipid dependence, little is known about the metabolism and nutritional requirements of all the seven species. Further to recent studies, 10 hydrophilic emulsifiers (HLB > 10) were examined in an agar diffusion test to determine their growth-promoting effect on reference strains of the different Malassezia species. Polyethylene glycol (PEG) 7 glyceryl monoalcanoate (Cetiol HE). PEG-glyceryl stearate (Tagat S2) and macrogol-50 stearate (Myrj 53) were metabolized by all strains, while PEG-35 castor oil (Cremophor EL) was metabolized only by M. furfur. The latter observation is due to a different metabolism of castor oil and its main component, ricinoleic acid (12-hydroxy oleic acid), which may also give an insight into the pathogenesis of diseases that are associated with Malassezia spp. As hydroxy fatty acids are important in maintaining the epidermal structure and function, their metabolism specifically by M. furfur might clarify some clinical aspects of pityriasis versicolor. Apart from this speculation, use of Cremophor EL, with splitting of esculin as an additional key character, improves the distinction of the species M. furfur, M. slooffiae and M. sympodialis.

Castor Oil↗

PubMed1982

Cellular fatty acids of Capnocytophaga species.

The cellular fatty acid composition of 18 clinical isolates and 4 reference strains of Capnocytophaga species (Capnocytophaga ochracea, Capnocytophaga gingivalis, and Capnocytophaga sputigena) was determined by gas-liquid chromatography. The fatty acid profiles of the 22 cultures were essentially identical and were characterized by major amounts (60% or greater) of a saturated, iso-branched-chain, 15-carbon acid (13-methyl-tetradecanoate) and the presence of two relatively uncommon saturated, iso-branched, 3-hydroxy acids (13-methyl-3-hydroxy-tetradecanoate and 15-methyl-3-hydroxy-hexadecanoate). The presence and relative amounts of these acids distinguish Capnocytophaga spp. from other gliding bacteria.

Capnocytophaga↗

PubMed2001

CD exciton chirality method for determination of the absolute configuration of beta-hydroxy-alpha-amino acid derivatives.

The absolute configuration of beta-hydroxy-alpha-amino acids was studied by CD exciton chirality method using 7-diethylaminocoumarin-3-carboxylate as a red-shifted chromophore. The CD spectra of bischromophoric derivatives of (S)-serine and (2S,3R)-threonine methyl esters (2 and 7) were compared with those of acyclic vic-aminoalcohols and diols (3--6 and 8--9). This study indicates that the polar carboxylate group of beta-hydroxy-alpha-amino acids makes them a unique subclass of vic-aminoalcohols. By combining the data of CD and NMR coupling constants, we are able to correlate their preferred conformer B and positive CD to the corresponding absolute configuration.

Amino Acids↗

PubMed1980

Skin surface lipids of the horse.

Skin surface lipids from the sides of male and female horses (Equus caballus) were collected in acetone and analyzed by thin layer chromatography and gas liquid chromatography. The sole components in both sexes were cholesterol, cholesteryl esters and the lactones of 32-, 32- and 36-carbon omega-hydroxy acids, each including a methyl group in the n-1 position. Most of the lactones were monounsaturated (either n-8 or n-10), but small amounts of saturated and dienoic species were present. A pooled sample of the skin surface lipids contained 14% cholesterol, 38% cholesteryl esters and 48% lactones.

Animals↗

PubMed1968

Lipid components of sialosylgalactosylceramide of human brain.

A ganglioside, previously designated HG-B in our laboratory, was isolated from mixed human brain ganglioside preparations and shown to contain equimolar quantities of sialic acid, galactose, and sphingosine. Treatment of this material with neuraminidase yielded a galactosylceramide. The ganglioside, now referred to as sialosylgalactosylceramide, thus appears to be identical with G(gal) reported by Kuhn and Wiegandt. The fatty acids and long-chain bases of this material were analyzed by gas-liquid chromatography. Approximately equal amounts of normal and hydroxy acids were found. Oleic, palmitic, and stearic acids were the only normal fatty acids present. In the hydroxy series, the C(24) and C(23) saturated acids were the major components. The ratio of C(20) to C(18) long-chain base was approximately 5:3. These data suggest that sialosylgalactosylceramide has no direct metabolic relationship with either the major brain gangliosides or adult brain cerebroside.

Brain Chemistry↗

PubMed1983

Acylglucosylceramides of pig epidermis: structure determination.

The acylglucosylceramides of pig epidermis comprise 56% of the total glucosylceramides and 3.3% of the total epidermal lipid by weight. Contrary to an earlier report on this lipid, the amide-linked fatty acid is not a dihydroxypentatriacontadienoic acid; rather, the fatty acids are a series of long chain omega-hydroxy acids consisting of 58% saturates, 35% monoenes, and 7% dienes, with predominant chain lengths of 30, 32, and 34 carbons, respectively. The structure of the acylglucosylceramides may therefore be formulated as 1-(3'-O-acyl)-beta-D-glucosyl-N-(omega-hydroxy)acylsphingosines. In accord with the previous report, 74% of the total esterified fatty acids is linoleic acid and the long-chain bases consist of homologous series of sphinganines and sphingenines ranging from 16-22 carbons in length. This unique glycolipid may play a role in epidermal barrier function.

Amides↗

PubMed1981

Valproic acid and several metabolites: quantitative determination in serum, urine, breast milk and tissues by gas chromatography-mass spectrometry using selected ion monitoring.

A method has been developed for the simultaneous quantitative determination of valproic acid (2-propylpentanoic acid) and its metabolites 2-propyl-2-pentenoic acid (trans), 2-propyl-3-pentenoic acid (trans), 2-propyl-4-pentenoic acid, 3-hydroxy-2-propylpentanoic acid, 4-hydroxy-2-propylpentanoic acid, 5-hydroxy-2-propylpentanoic acid, 3-oxo-2-propyl-pentanoic acid, and and 2-propylglutaric acid. All compounds were extracted at pH 5.0 with ethyl acetate. The concentrated extracts were trimethylsilylated and the resulting mixtures analyzed by a gas chromatography-mass spectrometry-computer system operated in the selected ion monitoring mode. Linear calibration curves were obtained in the concentration ranges studied (0.1-20 microgram/ml for metabolites, 0.1-150 microgram/ml for valproic acid. The recoveries of the drugs were between 92 and 97%. The relative standard deviations were between 3.9 and 8.1% (analysis of multiple 10-microliter samples of patient urine). The lower detection limits were found to be between 2.8 and 18 ng/ml using 200-microliter serum samples. The derivatized extracts were stable for at least one week. Applications of the method described include studies of placental transfer for valproic acid and metabolites in the human, the elimination of these substances by the neonate, their transfer via mother's milk, and their levels in mouse brain.

Adult↗

PubMed1999

Drug treatment of photoaged skin.

Although the prevention of skin aging is a holy grail of the cosmetic and pharmaceutical industries, this venture may be misplaced. The predominant clinical and biochemical features of aged skin are mostly attributable to photoaging rather than chronology. For instance chronic sun exposure is the major determinant of age spots (actinic lentigines) and wrinkles. Surgical approaches to the treatment of photoaging include face-lift, dermabrasion, chemical peeling, collagen and botulinum toxin injections, and laser re-surfacing. These approaches all have benefit and improve the clinical features of facial photoaging. Drug or pharmaceutical prevention and treatment of photoaged skin is still in its infancy. The main pharmaceutical approach to prevention of photoaging lies in the assiduous use of sunscreens. Recent evidence points to the importance of ultraviolet A (UVA) radiation as well as ultraviolet B (UVB) radiation in the aetiology of photoaging and thus the need for sunscreens that block both UVB and UVA. Drug treatment of photoaged skin can be categorised as antioxidants, alpha-hydroxy acids and topical retinoids. Of these 3 approaches only topical retinoids, particularly tretinoin (all-trans retinoic acid), have a well documented ability to repair photoaged skin at the clinical, histological and molecular level. Furthermore, the use of topical retinoids may actually prevent photoaging. The current interest in pharmaceutical modulation of the photoaging process has attracted considerable research into the mechanisms of photoaging and cutaneous aging. It is likely that treatment for, or prevention of, the chronological aging process may result from such research.

Aged↗

PubMed1996

Bioavailability and pharmacokinetics of oral topotecan: a new topoisomerase I inhibitor.

The results of preclinical and clinical studies indicate enhanced antineoplastic activity of topotecan (SKF 104864-A) when administered as a chronic treatment. We determined the apparent bioavailability and pharmacokinetics of topotecan administered orally to 12 patients with solid tumours in a two-part crossover study. The oral dose of 1.5 mg m-2 was administered as a drinking solution of 200 ml on day 1. The i.v. dose of 1.5 mg m-2 was administered as a 30 min continuous infusion on day 2. The bioavailability was calculated as the ratio of the oral to i.v. area under the curve (AUC) calculated up to the last measured time point. The oral drinking solution was well tolerated. The bioavailability revealed moderate inter-patient variation and was 30% +/- 7.7% (range 21-45%). The time to maximum plasma concentration after oral administration (Tmax) was 0.78 h (median; range 0.33-2.5). Total i.v. plasma clearance of topotecan was 824 +/- 154 ml min-1 (range 535-1068 ml min(-1)). The AUC ratio of topotecan and the lactone ring-opened hydrolysis product (hydroxy acid) was of the same order after oral (0.34-1.13) and i.v. (0.47-0.98) administration. The bioavailability of topotecan after oral administration illustrates significant systemic exposure to the drug which may enable chronic oral treatment.

Administration, Oral↗

PubMed1976

3-Hydroxy-3-methylglutaric acid and triton-induced hyperlipidemia in rats.

3-Hydroxy-3-methylglutaric acid (HMG) significantly decreased cholesterol, triglyceride and phospholipid levels in whole serum, serum beta-lipoproteins and liver of Triton-induced hyperlipidemic rats. Therapeutically 50 mg HMG/kg is equivalent to 200 mg nicotinic acid/kg in lowering all these lipid parameters. HMG may exert its hypolipidemic effect through inhibition of lipoprotein synthesis.

Animals↗

PubMed1997

Antimicrobial compounds from Ceanothus americanus against oral pathogens.

During the search for antimicrobial compounds from higher plant sources, a methanol extract of Ceanothus americanus demonstrated antimicrobial activity against selected oral pathogens. Through further bioassay-guided fractionation and purification, three triterpenes (ceanothic acid, 27-hydroxy ceanothic acid and ceanothetric acid) and two flavonoids (maesopsin and maesopsin-6-O-glucoside) were identified. Among these, ceanothetric acid and maesopsin-6-O-glucoside were new compounds. Ceanothic acid and ceanothetric acid demonstrated growth inhibitory effect against Streptococcus mutans, Actinomyces viscosus, Porphyromonas gingivalis, and Prevotella intermedia with MICs ranging from 42 to 625 micrograms ml-1. Maesopsin, its glucoside, and 27-hydroxy ceanothic acid, were inactive below the concentration of 500 micrograms ml-1.

Actinomyces viscosus↗

PubMed1977

Tissue lipid responses to 3-hydroxy-3-methylglutaric acid with different dietary fats.

Simultaneous administration of 3-hydroxy-3-methylglutaric acid (HMG) for 4 weeks to rats fed 20% saturated fats prevented rise of serum cholesterol, triglycerides, and phospholipids. Except phospholipids, other liver lipids were significantly decreased. HMG administration for 4 weeks along with atherogenic diet significantly decreased cholesterol and phospholipids of serum, liver, aorta, and heart. The phospholipids of epididymal fat and brain were also significantly lowered. The triglyceride levels in serum, liver, and epididymal fat were significantly decreased. The maximal hypolipidemic effect of HMG was observed in serum.

Adipose Tissue↗

PubMed1997

A Catalytic Asymmetric Synthesis ofN-Boc-beta-Methylphenylalanines.

An efficient, stereodivergent, and enantioselective synthesis of the syn and anti diastereomers of N-Boc-beta-methylphenylalanine has been developed. Starting from enantiomerically pure (2S,3S)-2,3-epoxy-3-phenyl-1-propanol, a three-step sequence, consisting of the oxidation of the primary alcohol up to the carboxyl stage, ring opening of the epoxy acid with Me(2)CuCNLi(2), and esterification of the resulting hydroxy acid with methyl iodide, leads to the hydroxy ester anti-10, which has been converted in a stereodivergent manner into both the (2S,3R) and the (2R,3R) diastereomers of N-Boc-beta-methylphenylalanine, syn-1 and anti-1, respectively. Activation of the secondary hydroxy group in anti-10 as a mesylate, followed by nucleophilic displacement with sodium azide, hydrogenolysis with simultaneous protection of the amino group, and saponification with LiOH, affords syn-1. The same reaction sequence applied to syn-10, obtained in turn by Mitsunobu reaction of anti-10 with p-nitrobenzoic acid followed by the hydrolysis of the resulting p-nitrobenzoate, leads to anti-1. Both products have been obtained with >/=99% enantiomeric excess.

Journal Article↗

PubMed2002

A CD exciton chirality method for determination of the absolute configuration of threo-beta-aryl-beta-hydroxy-alpha-amino acid derivatives.

The absolute configuration of threo-beta-aryl-beta-hydroxy-alpha-amino acids was studied by CD exciton chirality method using 7-diethylaminocoumarin-3-carboxylate as a red-shifted chromophore. Bischromophoric derivatives for a series of threo-beta-aryl-beta-hydroxy-alpha-amino acids (3a-h) were prepared and their CD spectra measured in CH2Cl2. By combining the data of CD and NMR coupling constants, we are able to correlate their preferred conformer (B) and the positive CD to the corresponding (2S,3R)-absolute configuration. These results are consistent with those obtained from serine and threonine derivatives, which represent the simplest form of beta-hydroxy-alpha-amino acids. This CD method could thus become a general method for determining the absolute configuration of threo-beta-aryl-beta-hydroxy-alpha-amino acids.

Amino Acids↗

PubMed2002

Growth of various cell types in the presence of lactic and glycolic acids: the adverse effect of glycolic acid released from PLAGA copolymer on keratinocyte proliferation.

Poly(alpha-hydroxy-acid)s derived from lactic acid (LA) and glycolic acid (GA) are bioresorbable polymers that are currently used in human surgery and in pharmacology to make temporary therapeutic devices. Nowadays, increasing attention is paid to these polymers in the field of tissue engineering. However, the literature shows that a large number of factors can affect many of their properties and the responses of biological systems. As part of our investigation of the biocompatibility of degradable aliphatic polyesters, the effects of LA and GA on the proliferation of various cells under in vitro cell culture conditions were studied. The release of LA and GA from films made of a copolymer synthesized by the zinc lactate method and composed of 37.5% L-lactyl, 37.5% D-lactyl, and 25% glycolyl repeating units was first investigated over a period of 30 days under abiotic conditions in a cell culture medium in order to identify a range of acid concentrations consistent with releases to be expected in real cell cultures. Four cell lines, namely 3T3-J2, C3H10(1/2), A431, and HaCat, and three primary cell cultures, namely rat endothelial cells, rat smooth muscle cells, and human dermal fibroblasts, were then allowed to grow in the presence of LA and GA at various concentrations taken within the selected 10-1000 mg/cm3 range. Little or no effect was observed on the proliferation of all cells except human keratinocytes, whose growth was dramatically inhibited by GA at concentrations as low as 10 mg/cm3. The inhibiting effect of GA was confirmed by considering the growth of keratinocytes on films made of the same copolymer, in comparison with poly(DL-lactic acid) and polystyrene taken as references. This work shows that GA-releasing degradable matrices are not adapted to the culture of keratinocytes with the aim of making skin grafts.

Animals↗

PubMed1985

The large sialoglycoprotein of human lymphocytes. II. Biochemical features.

Large sialoglycoprotein of human lymphocytes (L-LSGP) from thymocytes and from peripheral blood lymphocytes (PBL) of normal donor and of B chronic lymphocytic leukemia (CLL) patients was purified by affinity chromatography to Maclura pomifera agglutinin (MPA)-Sepharose followed by preparative sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE). L-LSGP from the three different sources was very similar in amino acid composition. It contained a high proportion of acidic and hydroxy amino acids and also significant amounts of cysteine. No reduction in mobility in SDS-PAGE was noted for unreduced L-LSGP. The molecule may already in its native form have an extended conformation containing either free sulfhydryl groups or small S-S loops not affecting mobility in SDS-PAGE. L-LSGP was found to be highly glycosylated, the thymocyte glycoprotein containing somewhat less carbohydrate by weight (44%) than that of PBL (normal PBL 53% and B CLL 52%). This was due primarily to a lower content of sialic acid. The molecules contained mannose, galactose, N-acetyl galactosamine, N-acetylglucosamine and sialic acid in molar ratios 1.0:3.0:1.1:1.2:1.3 (thymocyte L-LSGP), 1.0:3.8:1.2:1.0:1.7 (PBL L-LSGP) and 1.0:3.5:2.2:1.3:2.8 (B CLL L-LSGP). The weak interaction of L-LSGP with lentil lectin, concanavalin A (Con A) and leucoagglutinin (La), its unchanged mobility in SDS-PAGE after tunicamycin treatment and its high amount of hydroxy amino acids suggest that most carbohydrate chains are O-glycosidically linked to the peptide chain. Native as well as Nase-treated L-LSGP show size microheterogeneity. This is probably due to small chemical differences in the L-LSGP molecules from different lymphocyte subsets.

Amino Acids↗