Propionic Acid Methyl Ester Research Articles

Identification and Application of Bioactive Compounds from Garcinia xanthochymus Hook. for Weed Management

The allelopathic potential of plant species and their related compounds has been increasingly reported to be biological tools for weed control. The allelopathic potential of Garcinia xanthochymus was assessed against several test plant species: lettuce, rapeseed, Italian ryegrass, and timothy. The extracts of G. xanthochymus leaves significantly inhibited all the test plants in a concentration- and species-specific manner. Therefore, to identify the specific compounds involved in the allelopathic activity of the G. xanthochymus extracts, assay-guided purification was carried out and two allelopathic compounds were isolated and identified as methyl phloretate {3-(4-hydroxyphenyl) propionic acid methyl ester} and vanillic acid (4-hydroxy-3-methoxybenzoic acid). Both of the substances significantly arrested the cress and timothy seedlings growth. I50 values (concentrations required for 50% inhibition) for shoots and roots growth of the cress and timothy were 113.6–104.6 and 53.3–40.5 μM, respectively, for methyl phloretate, and 331.6–314.7 and 118.8–107.4 μM, respectively, for vanillic acid, which implied that methyl phloretate was close to 3- and 2-fold more effective than vanillic acid against cress and timothy, respectively. This report is the first on the presence of methyl phloretate in a plant and its phytotoxic property. These observations suggest that methyl phloretate and vanillic acid might participate in the phytotoxicity of G. xanthochymus extract.

Catecholic alkaloid sulfonates and aromatic nitro compounds from Portulaca oleracea and screening of their anti-inflammatory and anti-microbial activities

Acidic compounds were enriched from a water decoction of Portulaca oleracea using 717 anion exchange resin column chromatography. A total of 22 compounds including 9 catecholamine derivatives, of which six were rare sulfonic acid derivatives, and 9 nitro derivatives, were further isolated through various column chromatographic methods, and their structures were elucidated by interpreting their spectroscopic data and ECD calculations. Among them, 16 compounds were isolated from P. oleracea for the first time, 8 of which were undescribed compounds and four compounds were natural products. Pharmacological screening indicated that cis-3-(3-nitro-4-hydroxyphenyl)-methyl acrylate exhibited anti-inflammatory activity, measured as inhibition of nitric oxide production in LPS-stimulated RAW264.7 macrophage cells, with an EC50 value of 18.0μM, The compounds showed only weak anti-microbial activity with (2R)-(+)-2-chloro-3-(3-nitro-4-hydroxyphenyl)-propionic acid methyl ester inhibiting Candida albicans with a MIC of 256μg/mL, and 3-methoxy-4,5-dinitrophenol inhibiting Shigella sonnei with a MIC of 512μg/mL.

Evaluating Genotypes and Seed Treatments to Increase Field Emergence of Low Phytic Acid Soybeans

Low phytic acid (LPA) soybean [Glycine max (L.) Merr] genotypes reduce indigestible PA in soybean seeds in order to improve feeding efficiency of mono- and agastric animals, but often exhibit low field emergence, resulting in reduced yield. In this study, four LPA soybean varieties with two different genetic backgrounds were studied to assess their emergence and yield characters under 12 seed treatment combinations including two broad-spectrum, preplant fungicides (i.e., ApronMaxx (mefenoxam: (R,S)-2-[(2,6-dimethylphenyl)-methoxyacetylamino]-propionic acid methyl ester; fludioxonil: 4-(2,2-difluoro-1,3-benzodioxol-4-yl)-1H-pyrrole-3-carbonitrile) and Rancona Summit (ipconazole: 2-[(4-chlorophenyl)methyl]-5-(1-methylethyl)-1-(1H-1,2,4-triazol-1-ylmethyl) cyclopentanol; metalaxyl: N-(methooxyacetyl)-N-(2,6-xylyl)-DL-alaninate)), osmotic priming, and MicroCel-E coating. Two normal-PA (NPA) varieties served as controls. Both irrigated and non-irrigated plots were planted in Blacksburg and Orange, Virginia, USA in 2014 and 2015. Results revealed that three seed treatments (fungicides Rancona Summit and ApronMaxx, as well as Priming + Rancona) significantly improved field emergence by 6.4–11.6% across all genotypes, compared with untreated seeds. Seed priming was negatively associated with emergence across LPA genotypes. Seed treatments did not increase the yield of any genotype. LPA genotypes containing mips or lpa1/lpa2 mutations, produced satisfactory emergence similar to NPA under certain soil and environmental conditions due to the interaction of genotype and environment. Effective seed treatments applied to LPA soybeans along with the successful development of LPA germplasm by soybean breeding programs, will increase use of LPA varieties by commercial soybean growers, ultimately improving animal nutrition while easing environmental impact.

One new 1,4-napthoquinone derivative from the roots of Juglans mandshurica

A new 1,4-napthoquinone derivative, namely (S)-(-)-3-(8-hydroxy-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3-(4-hydroxy-3-methoxyphenyl)-propionic acid methyl ester (1), was isolated from the roots of Juglans mandshurica Maxim. The structure was identified based on HR-ESI-MS, 1D and 2D NMR spectroscopic methods.

Anti-neuroinflammatory effects of DPTP, a novel synthetic clovamide derivative in in vitro and in vivo model of neuroinflammation.

Neuroinflammation is one of the critical pathological mechanisms influencing various neurodegenerative disorders. Most of the neurodegenerative diseases involve over-activation of microglial cells contributing to the demise of neurons. The objective of the current study is to evaluate the anti-inflammatory effect of novel synthetic clovamide derivative on the suppression of microglial activation in an in vitro and in vivo model of neuroinflammation. We have used lipopolysaccharide (LPS) to induce an inflammatory response in murine BV-2 microglial cells. Molecular tools like immunocytochemistry and immunoblotting were used to study the activity of novel synthetic clovamide derivative to inhibit inflammation induced by LPS in microglial cells. In in vivo experiments, 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) intoxicated mouse model of neuroinflammation was developed to investigate the anti-neuroinflammatory effects of DPTP [3-(3,4-Dihydroxy-phenyl)-2-[4-(3-trifluoromethylphenyl)-but-2-enoylamino]-propionic acid methyl ester]. DPTP was observed to reduce the proinflammatory response in BV-2 cells induced by LPS. Further investigation revealed that DPTP attenuated phosphorylation of c-Jun N-terminal kinase (JNK) and extracellular signal-regulated kinase (ERK), which was accompanied by a decrease in nuclear translocation of nuclear factor-κB (NF-κB) in LPS-treated BV2 microglia. Moreover, prophylactic treatment with DPTP (20mg/kg) for 7 days suppressed MPTP induced glial activation and behavioral impairment. Overall, our findings suggested that, DPTP exerts anti-neuroinflammatory effects against activated microglia in an in vitro and in vivo model and hence might be a promising therapeutic agent for alleviating the evolvement of neurodegenerative diseases associated with microglial activation.

Separation and Analysis of Microwave-assisted Liquefied Products of Corn Stover

Corn stover was successfully liquefied by microwave heating at 160 °C with ethylene glycol (EG) used as the solvent and sulfuric acid as a catalyst. Gas chromatography and mass spectrometry (GC-MS) data indicated that methyl esters, including 3-(2-methyl-1,3-doxolane-2-yl) propionic acid methyl ester (PAME), levulinic acid isopropyl ester (LAE), methyl laurate, and methyl palmitate were the major degradation compounds, in addition to EG derivatives in the liquefied product of corn stover (LPCS). For high value-added utilization of LPCS, solvent extraction was applied to characterize the components and to separate it into useful fractions. After being dispersed in water, the water-soluble fraction of the LPCS was then extracted with organic solvents, including hexane, chloroform, diethyl ether, and ethyl acetate. Levulinic acid isopropyl ester showed the highest distribution in chloroform and ethyl acetate, while the lowest in hexane and ether. Levulinic acid isopropyl ester was selectively enriched to 28.76% and 43.65% by sequential extraction with chloroform and ethyl acetate, respectively, in accordance with the quantitative analysis.

A study of the biologically active conformation of the cholecystokinin-4 dipeptide analogue GB-115

The conformational analysis with 1H NMR spectroscopy method in solution and the structure-activity relationship study of a series sterically restricted analogs allowed to detect the possible biologically active conformation of N-(6-phenylhexanoyl)glycyl-tryptophan amide (GB-115), a highly active dipeptide cholecystokinin-4 analog with anxiolytic activity. The structure-activity relationship study of GB-115 and the series of its' glycine- and proline-containing analogs with different C-terminal substitute detected the anxiolytic activity of compounds with beta-turn like conformation and inactivity of compounds with gamma-turn like conformation. So, the GB-115 biologically active conformation is beta-turn. The results of nuclear Overhauser effect study permitted to qualify the betaII-turn conformation as GB-115 biologically active conformation. The following synthesis of sterically restricted GB-115 analogs (2S)-2-{(3R)-3-[(6-phenylhexanoyl)amino]-2-oxopyrrolidin-1-yl}-3-(1H-indol-3-yl)propionic acid ethyl ester, N-(6-phenylhexanoyl)glycyl-N(alpha)(methyl)-tryptophan ethyl ester, (2S)-2-[10,11-dihydro-5H-dibenzo[b,f] azepin-5-carbonyl)-amino]-3-(1H-indol-3-yl)propionic acid methyl ester and (2S)-2-[({3-[(ethoxycarbonyl)amino]-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl}carbonyl)amino]-3-(1H-indol-3-yl)propionic acid methyl ester confirmed the estimated type of GB-115 biologically active conformation.

Synthesis, complexation behavior and application of a new diphosphite ligand in rhodium-catalyzed hydroformylation

Oxidative coupling of 3-(3-tert-butyl-4-hydroxyphenyl)propionic acid methyl ester ( 2) gave dimethyl 3,3′-(5,5′-di-tert-butyl-6,6′-dihydroxybiphenyl-3,3′-diyl)-dipropionate ( 1c), which upon phosphorylation/transesterification with a phosphochloridite derived from ( R)-binaphthol, formed the new unsymmetrical binaphthol-bridged diphosphite 4. A rhodium catalyst based on 4 as ligand gave predominantly iso-selectivity in the hydroformylation of selected styrenes but opposite regioselectivity with 2,6-disubstituted derivatives. New chelate metal complexes (acac)RhL, PdCl 2L and PtCl 2L have been synthesized by reacting 4 with (acac)Rh(CO) 2, PdCl 2(MeCN) 2 and PtCl 2(COD), respectively. The structure of obtained compounds is determined based on 1H, 13C, 31P and 195Pt NMR spectroscopy and mass spectrometry data.

Small Molecule Inhibitors of Retinoic Acid 4-Hydroxylase (CYP26): Synthesis and Biological Evaluation of Imidazole Methyl 3-(4-(aryl-2-ylamino)phenyl)propanoates

The synthesis and potent inhibitory activity of novel imidazole methyl 3-(4-(aryl-2-ylamino)phenyl)propanoates in a MCF-7 CYP26A1 microsomal assay is described. The induction of CYP26A1 mRNA was used to evaluate the ability of the compounds to enhance the biological effects of all-trans retinoic acid (ATRA) in a retinoid-responsive neuroblastoma cell line. The most promising inhibitor, 3-imidazol-1-yl-2-methyl-3-[4-(naphthalen-2-ylamino)-phenyl]-propionic acid methyl ester (20), with an IC(50) of 3 nM (compared with liarozole IC(50) of 540 nM and R116010 IC(50) of 10 nM) was further evaluated for CYP selectivity using a panel of CYP enzymes, mutagenicity (Ames screen), and hepatic stability.

A concise, total synthesis and antibacterial evaluation of 2-hydroxy-1-(1 H-indol-3-yl)-4-methylpentan-3-one

Treatment of racemic 2-hydroxy-3-(1 H-indol-3yl)propionic acid methyl ester ( 5) with isopropyl magnesium chloride provided the title compound 1 and its isomer, 3-hydroxy-1-(indol-3-yl)-4-methylpentan-2-one ( 9). Both enantiomers (>96% ee) of each component were obtained via semi-preparative chiral supercritical fluid chromatography (SFC). In contrast to previous reports, these compounds, as well as their acetate derivatives, were not active or very weakly active against 16 bacterial strains, including Escherichia coli, Bacillus subtilis and Staphylococcus aureus.

Two new coumarins from Edgeworthia chrysantha

Two new coumarins, 8-[3-(2,4-benzenediol)-propionic acid methyl ester]-coumarin-7-β-D-glucoside (1) and 7-hydroxyl-odesmethoxyrutarensin (2), were isolated from the stems and barks of Edgeworthia chrysantha. Their structures were elucidated on the basis of spectroscopic data interpretation.

Aromatic Plant Oils as Fungicide for Organic Corn Production

The planting date for organic corn (Zea mays L.) is delayed in the spring to avoid cold and wet soils. Conventional farmers can use fungicide seed treatments to protect the emerging seedlings, but few organic fungicides are available. The objective of this research was to determine whether essential oils can be used as a contact fungicide seed treatment for organic corn. The essential oils of 18 plants were screened for their fungicidal properties against three common corn pathogens: Penicillium, Fusarium, and Pythium Five oils—cinnamon (Cinnamomum zeylanicum Blume), clove (Eugenia caryophyllata Thunb.), oregano (Origanum minutiflorum O. Schwarz and P.H. Davis), savory (Satureja montana L.), and thyme (Thymus vulgaris L.)—completely controlled all three pathogens in vitro. The minimum inhibitory concentration (MIC) for all pathogens was 800 μL L−1 and seedlings presented no phytotoxicity symptoms in the germination test at rates up to 64 μL kg−1 active ingredient (MIC × 20). Field emergence of inbred and hybrid seeds treated with the essential oils were significantly lower than seeds treated with the commercial fungicides Maxim XL {fludioxonil [4‐(2,2‐difluoro‐1,3‐benzodioxol‐4‐yl)‐1H‐pyrrole‐3‐carbonitrile] 21.4%; mefenoxam [(R)‐2‐[(2,6‐dimethylphenyl) methoxyacetylamino] propionic acid methyl ester] 8.4%}, which is a conventional fungicide; and Natural 2 (proprietary ingredients), which is an organic fungicide, but were not different from the organic fungicide Yield Shield (Bacillus pumilus GB34 0.28%) or an untreated control.

Synthesis and antiarrhythmic activity of (1,3-dimethyl-5-nitro-5-hexahydropyrimidinyl)-propionic acid methyl ester

(1,3-Dimethyl-5-nitro-5-hexahydropyrimidinyl)propionic acid methyl ester (I) was obtained with a 83% yield using a Mannich type reaction of 4-nitrobutanoic acid methyl ester with excess formalin and methylamine. It was found that compound I possesses low toxicity and shows antiarrhythmic activity on models of arrhythmia induced by intravenous injections of calcium chloride and aconitine in rats.

Longicalycinin A, a New Cytotoxic Cyclic Peptide from Dianthus superbus var. longicalycinus (Maxim.) Will.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Complexes of the {Re VOX 2} + (X = Cl, Br) core with single amino acid chelate derivatives

The reactions of 1 equiv. of the ligand 3-(ethoxycarbonylmethyl-pyridin-2-ylmethyl-amino)-propionic acid methyl ester ( 2) with the Re(V) starting materials [ReOX 3(PPh 3) 2] (X = Cl, Br) in refluxing chloroform yielded the Re(V)-oxo dihalide complexes [ReOX 2{(C 5H 4NCH 2)N(CH 2CO 2)(C 2H 4CO 2CH 3)}] (X = Cl, 3; X = Br, 4). The complexes were characterized by elemental analysis, NMR and IR spectroscopy, cyclic voltammetry and X-ray crystallography. Complex 3 displays distorted octahedral coordination geometry with the tridentate ligand coordinating facially to the Re(V) center. The carboxylate oxygen atom occupies an axial site trans to the Re O bond. The two chlorine atoms consequently adopt a cis configuration.

Longicalycinin A, a New Cytotoxic Cyclic Peptide from Dianthus superbus var. longicalycinus (MAXIM.) WILL.

A new cyclic peptide, longicalycinin A (1), and six known compounds, vaccaroside A, dianoside A, dianoside G, 3-(4-hydroxy-3-methoxy-phenyl)propionic acid methyl ester, p-hydroxybenzoic acid, and p-hydroxybenzaldehyde were isolated from the MeOH extract of Dianthus superbus var. longicalycinus. The amino acid sequences of 1 was elucidated as cyclo(Gly(1)-Phe(2)-Tyr(3)-Pro(4)-Phe(5)-) on the basis of ESI tandem mass fragmentation analysis, chemical evidence, and extensive 2D NMR methods. Furthermore, compound 1 showed cytotoxicity to Hep G2 cancer cell line.

Bromophenol derivatives from the red alga Rhodomela confervoides.

Eight new bromophenol derivatives, 2,3-dibromo-4,5-dihydroxybenzyl methyl sulfoxide (1), 4-(2,3-dibromo-4,5-dihydroxyphenyl)-3-butene-2-one (2), 2-(3-bromo-5-hydroxy-4-methoxyphenyl)-3-(2,3-dibromo-4,5-dihydroxyphenyl)propionic acid (3), 2-(3-bromo-5-hydroxy-4-methoxyphenyl)-3-(2,3-dibromo-4,5-dihydroxyphenyl)propionic acid methyl ester (4), 2-phenyl-3-(2,3-dibromo-4,5-dihydroxyphenyl)propionic acid (5), 4'-methoxy-2'',3',3''-tribromo-4'',5',5''-trihydroxydiphenylacetic acid (6), and 3-bromo-5-hydroxy-4-methoxyphenylacetic acid (7) and its methyl ester (8), together with a known bromophenol, 3-bromo-5-hydroxy-4-methoxybenzoic acid (9), were isolated from the red alga Rhodomela confervoides. Their structures were elucidated by spectroscopic methods including IR, EIMS, FABMS, ESIMS, HRFABMS, HRESIMS, 1D and 2D NMR, and single-crystal X-ray structure analysis. Compounds 1-4, 8, and 9 were found inactive against several human cancer cell lines and microorganisms.

Conjugation of a novel histidine derivative to biomolecules and labelling with [99mTc(OH2)3(CO)3]+.

The new histidine derivative 3-[1-[3-(9H-fluoren-9-ylmethoxycarbonylamino)-propyl]-1H-imidazol-4-yl]-2-(3-trimethylsilanyl-ethylcarboxyamino)-propionic acid methyl ester (7) has been prepared via alkylation of the histidine urea derivative (7S)-5,6,7,8-tetrahydro-7-(methoxycarbonyl)-5-oxoimidazo-[1,5-c]-pyrimidine (2) with Fmoc-protected 3-iodopropyl-amine, followed by ring opening with 2-trimethylsilylethanol. After Fmoc cleavage by HNEt2, the histidine amine derivative was coupled to biotin, to the pentapeptide leucine-enkephalin and to Vitamin B12-b-acid by amide formation, employing TBTU as the coupling reagent. In order to make the histidine accessible for labelling, the teoc protecting group was removed by either NBu4F (for the biotin conjugate) or by TFA (for the enkephalin and B12 conjugates). Reaction of a 10(-4) M solution of the bioconjugates with [99mTc(H2O)3(CO)3]+ at 50 degrees C for 30 min led to the formation of one single new peak in the HPLC radiochromatogram in each case, confirming quantitative labelling of the respective biomolecules. To assess the nature of the labelled compounds, the rhenium analogues with Re(CO)3 were also synthesised and similar retention times confirmed the identity with the 99mTc labelled conjugates.

Planting Date Effects on Stand Establishment and Yield of Chile Pepper

Chile pepper (Capsicum annuum L.) yields are highly variable and are strongly influenced by disease and weather. The goal of two field experiments was to evaluate crop management factors, especially planting date, that could contribute to improved and more consistent crop production. Current practice in New Mexico is to direct seed the crop from 13 to 27 Mar. In the first experiment, chile pepper was direct seeded on three planting dates, 13, 20, and 27 Mar. 2000, without or with a fungicide treatment of pentachloronitrobenzene and mefenoxam for the control of damping off. The results indicate planting date had no effect on stand establishment or yield. Fungicide treatment, significantly reduced stand, but had no effect on yield. In the second experiment, chile pepper was direct seeded on six planting dates, 13, 20, 27 Mar. and 3, 10, 17, Apr. 2001, with or without an application of phosphorus fertilizer, P at 29.4 kg·ha-1, banded beneath the seed row. During the growing season, this experimental planting suffered, as did commercial plantings in New Mexico, from high mortality and stunting due to beet curly top virus, a disease transmitted by the beet leafhopper. The results indicate planting date had a significant effect on crop performance. The best stand establishment and highest yield were associated with the earliest planting date, 13 Mar. This date also resulted in the least viral disease damage. Phosphorus fertilizer had no effect on stand establishment or yield. Chemical names used: pentachloronitrobenzene (PCNB); (R)-2-[(2,6-dimethylphenyl)-methoxyacetylamino]-propionic acid methyl ester (mefenoxam).

A general approach to l-tyrosine porphyrins

A novel and general approach has been developed to prepare l-tyrosine-containing porphyrins. The key intermediates, 2- tert-butoxycarbonylamino-3-(3-formyl-4-hexyloxy-phenyl)-propionic acid hexyl ester and 2- tert-butoxycarbonylamino-3-(3-formyl-4-methoxy-phenyl)-propionic acid methyl ester, were prepared by the Reimer–Tiemann reaction of Boc-protected l-tyrosine, which was followed by esterification and alkylation of the phenol hydroxide. A number of novel chiral l-tyrosine porphyrins were obtained from the reactions of 2- tert-butoxycarbonylamino-3-(3-formyl-4-alkoxy-phenyl)-propionic acid ester with different dipyrrolylmethanes and the reaction of 5-(4-trifluoromethylphenyl)pyrromethane afforded the highest yield. The tyrosine porphyrins could be readily deprotected to afford the corresponding diacid or diamine derivatives.