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At least 217 records · Page 12Linked to original sources
PubMed2004

Inheritance of evolved glyphosate resistance in Conyza canadensis (L.) Cronq.

N-(phosphonomethyl)glycine (glyphosate) resistance was previously reported in a horseweed [Conyza (=Erigeron) canadensis (L.) Cronq.] population from Houston, DE (P (0) (R) ). Recurrent selection was performed on P (0) (R) , since the population was composed of susceptible (5%) and resistant (95%) phenotypes. After two cycles of selection at 2.0 kg ae glyphosate ha(-1), similar glyphosate rates that reduced plant growth by 50%, glyphosate rates that inflicted 50% mortality in the population, and accumulations of half of the maximum detectable shikimic acid concentration were observed between the parental P (0) (R) and the first (RS(1)) and second (RS(2)) recurrent generations. In addition, RS(1) and RS(2) did not segregate for resistance to glyphosate. This suggested that the RS(2) population comprised a near-homozygous, glyphosate-resistant line. Whole-plant rate responses estimated a fourfold resistance increase to glyphosate between RS(2) and either a pristine Ames, IA (P (0) (P) ) or a susceptible C. canadensis population from Georgetown, DE (P (0) (S) ). The genetics of glyphosate resistance in C. canadensis was investigated by performing reciprocal crosses between RS(2) and either the P (0) (P) or P (0) (S) populations. Evaluations of the first (F(1)) and second (F(2)) filial generations suggested that glyphosate resistance was governed by an incompletely dominant, single-locus gene (R allele) located in the nuclear genome. The proposed genetic model was confirmed by back-crosses of the F(1) to plants that arose from achenes of the original RS(2), P (0) (P) , or P (0) (S) parents. The autogamous nature of C. canadensis, the simple inheritance model of glyphosate resistance, and the fact that heterozygous genotypes (F(1)) survived glyphosate rates well above those recommended by the manufacturer, predicted a rapid increase in frequency of the R allele under continuous glyphosate selection. The impact of genetics on C. canadensis resistance management is discussed.

Alleles↗
PubMed1986

[Organic acids of various kinds of vegetables. IV. Changes in the acids and sugar in tomatoes, sweet peppers and cucumbers during development and ripening].

Concentrations of organic acids and sugars in tomatoes and sweet peppers change notably during ripening. The concentration of malic acid decreases while that of citric acid increases considerably and in redripe fruits clearly exceeds the content of malic acid. Several maxima and minima in acid concentrations occur during development. Both species show constant proportions of citric and isocitric acid (200:1 and 30:1 respectively). In sweet pepper, quinic and ascorbic acid can be found in noticeably higher amounts than in tomatoes. Additionally, succinic acid was detected in tomatoes and fumaric and shikimic acid in sweet pepper. Glucose and fructose, in approximately equal amounts, are the main sugar components; their concentrations are increased during ripening, especially in sweet peppers. The leaves of tomatoes and sweet pepper contain more malic acid and less citric acid than redripe fruits, though here as well citric acid predominates. There is considerably less glucose and fructose present in the leaves of sweet pepper than in the fruits while sucrose is increased. Sucrose is the main sugar component in the leaves. Compared to tomatoes and sweet peppers, egg-plants contain more amounts. - Potatoes contain citric, malic, quinic, succinic, fumaric, and soluble oxalic acid (in order of decreasing amounts). - In cucumbers malic acid notably exceeds citric acid. Both acids hardly change in concentration during ripening. Sugar content decreases during ripening.

Acids↗
PubMed2001

Investigation of the role of 3-hydroxyanthranilic acid in the degradation of lignin by white-rot fungus Pycnoporus cinnabarinus.

An aminophenol, 3-hydroxyanthranilic acid (3-HAA), has been proposed to play important roles in lignin degradation. Production of 3-HAA in Pycnoporus cinnabarinus was completely inhibited by a combination of tryptophan and S-(2-aminophenyl)-L-cysteine S,S-dioxide (APCD) while the fungus grew well and produced high amounts of laccase. The biosynthesis of 3-HAA is mainly through the metabolism of tryptophan in the kynurenine pathway. A minor pathway for 3-HAA synthesis is through the hydroxylation of anthranilic acid during the biosynthesis of tryptophan in the shikimic acid pathway. Through UV irradiation of wild-type P. cinnabarinus (WT-Pc) spores, a 3-HAA-less mutant was produced. Both WT-Pc, under the inhibitory culture condition, and the 3-HAA-less mutant were found to degrade lignin in unbleached kraft pulp as efficiently as the WT-Pc, which unambiguously demonstrated that 3-HAA does not play an important role in the fungal degradation of lignin.

Journal Article↗
PubMedDate not supplied

Anti-AIDS agents, 2: Inhibitory effects of tannins on HIV reverse transcriptase and HIV replication in H9 lymphocyte cells.

Nine tannins, including gallo- and ellagitannins, were evaluated as potential inhibitors of HIV replication. 1,3,4-Tri-O-galloylquinic acid [1], 3,5-di-O-galloyl-shikimic acid [2], 3,4,5-tri-O-galloylshikimic acid [3], punicalin [6], and punicalagin [7] inhibited HIV replication in infected H9 lymphocytes with little cytotoxicity. Two compounds, punicalin and punicacortein C [8], inhibited purified HIV reverse transcriptase with ID50 of 8 and 5 microM, respectively. Further studies with H9 lymphocytes indicated that chebulagic acid [5] and punicalin did not inactivate virus directly. However, 1,3,4-tri-O-galloylquinic acid and 3,5-di-O-galloylshikimic acid were more effective inhibitors under those conditions. All tannins appear to inhibit virus-cell interactions. Thus, inspite of their anti-RT activity, the mechanism by which tannins inhibit HIV may not be associated with this enzyme.

Antiviral Agents↗
PubMed2005

Quantitation of nine organic acids in wild mushrooms.

The organic acids composition of six wild edible mushroom species (Amanita caesarea, Boletus edulis, Gyroporus castaneus, Lactarius deliciosus, Suillus collinitus, and Xerocomus chrysenteron) was determined by an HPLC-UV detector method. The results showed that all of the samples presented a profile composed of at least five organic acids: citric, ketoglutaric, malic, succinic, and fumaric acids. Several samples also contained oxalic, ascorbic, quinic, and shikimic acids. In a general way, the quantitation of the identified compounds indicated that malic acid, followed by the pair citric plus ketoglutaric acids, were the main compounds in the analyzed species, with the exception of A. caesarea, in which malic and ascorbic acids were the most abundant compounds. The relative amounts and the presence/absence of each identified compound may be useful for the differentiation of the species.

Agaricales↗
PubMed1986

Purification and characterization of hydroxycinnamoyl D-glucose. Quinate hydroxycinnamoyl transferase in the root of sweet potato, Ipomoea batatas Lam.

We have previously proposed a chlorogenic acid biosynthetic pathway which involves a transesterification reaction between hydroxycinnamoyl D-glucose and D-quinic acid. The proposed pathway was based on tracer experimental results (Kojima, M., and Uritani, I. (1972) Plant Cell Physiol. 13, 311-319). The enzyme that catalyzes the above reaction has been purified 160-fold from sweet potato root (Ipomoea batatas Lam.) and characterized. The purified enzyme yielded one band of 26,000 daltons on sodium dodecyl sulfate-polyacrylamide gel electrophoresis, and its molecular weight was estimated to be 25,000 by gel filtration chromatography. Therefore, the enzyme seems to consist of a single polypeptide of 25,000-26,000 daltons. The isoelectric point of the enzyme was 8.6. The optimum pH of the enzyme reaction was 6.0. The enzyme did not require any metal for activity and showed a broad substrate specificity toward hydroxycinnamoyl D-glucose as donors. The Km and Vmax values were 3.7 mM and 8.5 units/mg of protein for t-cinnamoyl D-glucose, 3.9 mM and 15.1 units/mg of protein for p-coumaroyl D-glucose, and 14.3 mM and 38.1 units/mg of protein for caffeoyl D-glucose. The enzyme showed a strict substrate specificity toward D-quinic acid-related compounds as acceptors; the Km and Vmax values were 16.7 mM and 15.1 units/mg of protein for D-quinic acid, 250 mM and 19.0 units/mg of protein for shikimic acid, and there was no activity with either L-malic acid or meso-tartaric acid. The enzyme activity changed in a manner suggesting its involvement in chlorogenic acid biosynthesis during incubation of sliced sweet potato root tissues.

Acyltransferases↗
PubMed2004

Novel lipid-peroxidation- and cyclooxygenase-inhibitory tannins from Picrorhiza kurroa seeds.

From the AcOEt extract of the seeds of Picrorhiza kurroa were isolated picrorhiza acid (1), picrorhizoside A (2), picrorhizoside B (3), picrorhizoside C (4), (-)-shikimic acid (5), gallic acid (6), ellagic acid (7), isocorilagin (8), 1-O-galloyl-beta-D-glucose (9), 1-O,3-O,6-O-trigalloyl-beta-D-glucose (10), and 1-O,2-O,3-O,4-O,6-O-pentagalloyl-beta-D-glucose (11), and their structures were established by extensive NMR and chemical studies. Constituents 1-4 are novel compounds, and the known compounds 5-11 have been isolated for the first time from the seeds of P. kurroa. Compounds 2 and 3 were hydrolyzed and yielded 12, isochebulic acid. Compounds 1-12 showed 89.6, 77.3, 56.1, 50.5, 11.0, 86.4, 50.5, 29.2, 70.9, 50.5, 56.5, and 86.1% inhibition of lipid peroxidation at 5 microg/ml, respectively. The commercial antioxidants BHA (1.8 microg/ml), BHT (2.2 microg/ml), and TBHQ (1.66 microg/ml) inhibited lipid peroxidation at 85.6, 87.1, and 81.1%, respectively. The inhibition of cyclooxygenase-1 (COX-1) by 2-5, 7, 8, and 10-12 at 100 microg/ml was 41.9, 28.4, 32.9, 9.3, 70.7, 34.7, 16.0, 89.6, and 53.4%, respectively. Similarly, compounds 1-8 and 11 and 12, at 100 microg/ml, inhibited COX-2 by 12.6, 15.3, 25.1, 5.3, 13.2, 21.7, 2.0, 42.4, 43.4, and 36.9%, respectively.

Cyclooxygenase Inhibitors↗
PubMed2002

Galactosyl-mimodye ligands for Pseudomonas fluorescens beta-galactose dehydrogenase.

Protein molecular modelling and ligand docking were employed for the design of anthraquinone galactosyl-biomimetic dye ligands (galactosyl-mimodyes) for the target enzyme galactose dehydrogenase (GaDH). Using appropriate modelling methodology, a GaDH model was build based on a glucose-fructose oxidoreductase (GFO) protein template. Subsequent computational analysis predicted chimaeric mimodye-ligands comprising a NAD-pseudomimetic moiety (anthraquinone diaminobenzosulfonic acid) and a galactosyl-mimetic moiety (2-amino-2-deoxygalactose or shikimic acid) bearing an aliphatic 'linker' molecule. In addition, the designed mimodye ligands had an appropriate in length and chemical nature 'spacer' molecule via which they can be attached onto a chromatographic support without steric clashes upon interaction with GaDH. Following their synthesis, purification and analysis, the ligands were immobilized to agarose. The respective affinity adsorbents, compared to other conventional adsorbents, were shown to be superior affinity chromatography materials for the target enzyme, Pseudomonas fluorescensbeta-galactose dehydrogenase. In addition, these mimodye affinity adsorbents displayed good selectivity, binding low amounts of enzymes other than GaDH. Further immobilized dye-ligands, comprising different linker and/or spacer molecules, or not having a biomimetic moiety, had inferior chromatographic behavior. Therefore, these new mimodyes suggested by computational analysis, are candidates for application in affinity labeling and structural studies as well as for purification of galactose dehydrogenase.

Amino Acid Sequence↗
PubMed1992

Biosynthesis of ansatrienin by Streptomyces collinus: cell-free transformations of cyclohexene- and cyclohexadienecarboxylic acids.

Cell-free extracts of Streptomyces collinus were tested with various cyclohexene- and cyclohexadienecarboxylic acids in order to determine the latter stages of the conversion of shikimic acid to cyclohexanecarboxylic acid. It was demonstrated that the final three steps of this process involve reduction of the alpha,beta-double bond of 1(6),2-cyclohexadienylcarbonyl CoA, an isomerization of the double bond of the resulting 2-cyclohexenylcarbonyl CoA to afford 1-cyclohexenylcarbonyl CoA, and a subsequent reduction of the newly formed alpha,beta-double bond. Both of the reduction steps were shown to require NADPH as a cofactor.

Anti-Bacterial Agents↗
PubMed2004

A novel approach to determine the glyphosate tolerant trait in soybeans.

The ability of soybean breeders to accurately, economically, and rapidly determine the transfer of the CP4 gene, the gene which confers soybean tolerance to the herbicide glyphosate, to elite soybean lines is essential to development of new glyphosate tolerant soybean (GTS) cultivars. This research focused on a simple greenhouse screening procedure to replace large, costly, and laborious field screening. Non-GTS seed was determined to be susceptible to soaking in a 1% glyphosate solution for 4 h. This process is quicker, more efficient, and as reliable as field screening for determination of glyphosate susceptibility in soybean seed. Furthermore, this research clearly demonstrates that the metabolic pathway of glyphosate activity, the shikimate acid pathway, is active, and the target enzyme of glyphosate, 5-enol-pyruvyl-shikimate-3-phosphate synthase, is present during seed germination.

Absorption↗
PubMed1978

Biosynthesis of the macrolide antibiotic chlorothricin: basic building blocks.

The biosynthesis of chlorothricin (I), a macrolide antibiotic isolated from Streptomyces antibioticus Tü 99, has been studied by feeding experiments with 14C- and 3H-labeled precursors. Acetate and propionate, but not methionine and mevalonate, were incorporated into the macrocylic aglycone of the antibiotic. Glucose and the various carbon atoms of tyrosine, except the carboxyl carbon, also contributed label to the aglycone. Glucose also seems to be a specific precursor of the 2-deoxyrhamnose moiety, probably via a process involving a hydrogen shift from C-4 to C-6 of the hexose. The substituted 6-methylsalicylic acid moiety seems to be derived from acetate and one O-methyl group provided by methionine; shikimic acid is not incorporated.

Acetates↗
PubMed2000

A novel delta(3),delta(2)-enoyl-CoA isomerase involved in the biosynthesis of the cyclohexanecarboxylic acid-derived moiety of the polyketide ansatrienin A.

The side chain of the antifungal polyketide ansatrienin A produced by Streptomyces collinus contains a cyclohexanecarboxylic acid (CHC) derived moiety. This CHC in the coenzyme A activated form (CHC-CoA) is derived from shikimic acid via a pathway in which the penultimate step is the isomerization of 2-cyclohexenylcarbonyl-CoA to 1-cyclohexenylcarbonyl-CoA. We have purified a 28 kDa 2-cyclohexenylcarbonyl-CoA isomerase (ChcB) from S. collinus and cloned and sequenced the corresponding chcB gene. The predicted amino acid sequence of ChcB showed moderate sequence identity to members of the hydratase/isomerase superfamily of enzymes. The recombinant ChcB was overexpressed in Escherichia coli and purified to homogeneity using metal chelate chromatography. Kinetic analysis demonstrated that recombinant ChcB had wide substrate specificity and could catalyze a double bond isomerization using 2-cyclohexenylcarbonyl-CoA (K(m) 116 +/- 68 microM, k(cat)( )()3.7 +/- 1.0 min(-)(1)), trans-3-hexenyl-CoA (K(m) 39 +/- 10 microM, k(cat)( )()12.8 +/- 1 min(-)(1)), and vinylacetyl-CoA (K(m) 156 +/- 34 microM, k(cat)( )()29 +/- 3 min(-)(1)) as substrates. ChcB activity in cell extracts of S. collinus SP1, an insertionally disrupted chcB mutant, was shown to decrease by more than 99% (as compared to the wild-type strain) using all three of these substrates. The S. collinus SP1 strain, unlike the wild-type strain, could not produce omega-cyclohexyl fatty acids but was still able to grow efficiently on methyl oleate as a sole carbon source. These observations demonstrate that the S. collinus ChcB is required for catalyzing the isomerization of 2-cyclohexenylcarbonyl-CoA to 1-cyclohexenylcarbonyl-CoA during CHC-CoA biosynthesis but not for degradation of unsaturated fatty acids. The chcB gene does not appear to be associated with the ansatrienin biosynthetic gene cluster, which has previously been shown to contain at least one gene known to be essential for CHC-CoA biosynthesis. This finding represents a notable exception to the general rule regarding the clustering of polyketide biosynthetic pathway genes.

Amino Acid Sequence↗
PubMed2006

Rosmarinic acid synthase is a new member of the superfamily of BAHD acyltransferases.

Purification of rosmarinic acid synthase (hydroxycinnamoyl-CoA:hydroxyphenyllactate hydroxycinnamoyltransferase) from suspension cells of Coleus blumei Benth. (Lamiaceae) by fractionated ammonium sulphate precipitation, hydrophobic interaction chromatography and two affinity chromatography steps led to the identification of peptide sequences, which enabled a PCR-based approach to isolate the full-length cDNA encoding this enzyme. The open reading frame of the cDNA had a length of 1290 base pairs encoding a protein of 430 amino acid residues with a molecular mass of 47,932 Da with typical characteristics of an acyltransferase of the BAHD superfamily. The cDNA was heterologously expressed in Escherichia coli. The enzyme displayed the activity of rosmarinic acid synthase using 4-coumaroyl- and caffeoyl-coenzyme A and 4-hydroxyphenyllactate as well as 3.4-dihydroxyphenyllactate as substrates. Shikimic acid and quinic acid were not able to serve as hydroxycinnamoyl acceptors. This therefore is the first report of the cDNA-cloning of a rosmarinic acid synthase.

Acyltransferases↗
PubMed1988

Nutritional requirements of Methanomicrobium mobile.

A defined medium was developed for Methanomicrobium mobile BP. M. mobile required acetate for growth; the optimal concentration was 30 mM. Other requirements and their optimal concentrations included isobutyrate (0.65 mM), isovalerate (0.73 mM), and 2-methylbutyrate (1.5 mM). The appropriate branched-chain amino acids did not substitute for these branched-chain fatty acids. M. mobile required tryptophan at an optimal concentration of 24 microM. Indole substituted for tryptophan, but the possible precursor compounds shikimic acid and anthranilic acid and the degradation compound skatole did not. Vitamin requirements and their optimal concentrations included pyridoxine (0.49 microM), thiamine (0.15 microM), biotin (0.04 microM), and vitamin B12 (0.04 microM); p-aminobenzoic acid (0.18 microM) was required for optimal growth, but folic acid did not replace p-aminobenzoic acid. M. mobile required an unidentified growth factor found in ruminal fluid or extracts of Methanobacterium thermoautotrophicum for growth. M. mobile has a complex nutrition compared with that of other methanogens, but not an unusual nutrition in the context of organisms from the ruminal ecosystem.

Acetates↗
PubMed1985

Incorporation of chorismic acid and 4-aminobenzoic acid into the 4-hydroxyaniline moiety of N-(gamma-L-glutamyl)-4-hydroxyaniline in Agaricus bisporus.

Agaricus bisporus contains the unique aniline derivative, N-(gamma-L-glutamyl)-4-hydroxyaniline. 14C-labelled chorismic acid was quantitatively incorporated into the 4-hydroxyaniline moiety of this aniline derivative, whereas 14C-labelled prephenic acid and anthranilic acid were not incorporated into 4-hydroxyaniline. These observations indicate the branch point of the biosynthetic route of 4-hydroxyaniline in the shikimic acid pathway to be chorismic acid. Moreover, 4-aminobenzoic acid proved to be an effective precursor of 4-hydroxyaniline.

4-Aminobenzoic Acid↗
PubMed1976

Synthesis of anacardic acids in seeds of Ginkgo biloba.

Anacardic (6-alkylsalicylic) acids and common lipids are efficiently synthesized by immature seeds of Ginkgo biloba. The seeds were incubated with 14C-labeled acetic, malonic and palmitoleic acids, glucose, and other potential precursors. Levels of 14C in common lipids and in anacardic acids, and the distribution of 14C in anacardic acids were determined. The results show that the salicylic moiety is synthesized by a polyketide pathway via malonic acid. The chain moiety for anacardic acid synthesis is in a different state of activation and/or site than chains that are used for synthesis of the common lipids. Labeled shikimic acid did not contribute 14C to anacardic acids, nor to other lipids, and palmitoleic acid was incorporated only into common lipids.

Acetates↗
PubMed2005

Structure-based design, synthesis, and biological evaluation of inhibitors of Mycobacterium tuberculosis type II dehydroquinase.

The syntheses by Suzuki cross-coupling of 12 5-aryl analogues of the known inhibitor (1R,3R,4R)-1,3,4-trihydroxycyclohex-5-en-1-carboxylic acid are reported. These compounds were found to be reversible competitive inhibitors against Mycobacterium tuberculosis type II dehydroquinase, the third enzyme of the shikimic acid pathway. The most potent inhibitor, the 3-nitrophenyl derivative, has a K(i) of 54 nM, over 180 times more potent than the reported inhibitor (1R,3R,4R)-5-fluoro-1,3,4-trihydroxycyclohex-5-en-1-carboxylic acid and more than 700 times lower than the K(M) of the substrate, making it the most potent known inhibitor against any type II dehydroquinase. Docking studies using GOLD (version 2.2) indicated a key electrostatic binding interaction between the aromatic rings and Arg19, a residue that has been identified as essential for enzyme activity.

Cyclohexanols↗