Synthesis, characterization,thermal behavior,and antifungal activity of La(Ⅲ) complexes with cinnamates and 4-methoxyphenylacetate

In this study a series of trivalent lanthanum complexes with 4-（R）-cinnamate （4-Rcinn, R=H（1）, MeO（2）, Cl（3）） and 4-methoxyphenylacetate ligands （4） were prepared and their antifungal activity against Candida albicans, Aspergillus niger and Trichophyton mentagrophytes were examined. Compounds 1-4 were synthesized by a metathesis reaction and fully characterized by elemental analysis, IR, 1H and 13C NMR spectroscopy, fluorescence spectra, thermogravimetry （TG）, derivative thermogravimetry （DTG）, differential scanning calorimetry （DSC） and X-ray diffraction powder patterns. In emission studies, it was observed that lu-minescence intensity was enhanced in the presence of lanthanide ion. The results of X-ray diffraction patterns indicated that all com-plexes studied exhibited crystalline structure. Thermal behavior by TG, DTG, and DSC studies permitted to estimating the hydration degree of the compounds and showed the formation of decomposition products like lanthanum oxide. Determined by antifungal stud-ies, lanthanum complexes 1-4 demonstrated antifungal activity toward all pathogenic fungal strains tested. Compounds 2 and 4 showed significant growth inhibition for A. niger and C. albicans, respectively.

Cinnamic acid regulates the intestinal microbiome and short-chain fatty acids to treat slow transit constipation

BACKGROUND Slow transit constipation(STC)is a disorder with delayed colonic transit.Cinnamic acid(CA)is an organic acid in natural plants,such as Radix Scrophulariae(Xuan Shen),with low toxicity and biological activities to modulate the intestinal microbiome.AIM To explore the potential effects of CA on the intestinal microbiome and the primary endogenous metabolites-short-chain fatty acids(SCFAs)and evaluate the therapeutic effects of CA in STC.METHODS Loperamide was applied to induce STC in mice.The treatment effects of CA on STC mice were assessed from the 24 h defecations,fecal moisture and intestinal transit rate.The enteric neurotransmitters:5-hydroxytryptamine(5-HT)and vasoactive intestinal peptide(VIP)were determined by the enzyme-linked immunosorbent assay.Hematoxylin-eosin and Alcian blue and Periodic acid Schiff staining were used to evaluate intestinal mucosa's histopathological performance and secretory function.16S rDNA was employed to analyze the composition and abundance of the intestinal microbiome.The SCFAs in stool samples were quantitatively detected by gas chromatography-mass spectrometry.RESULTS CA ameliorated the symptoms of STC and treated STC effectively.CA ameliorated the infiltration of neutrophils and lymphocytes,increased the number of goblet cells and acidic mucus secretion of the mucosa.In addition,CA significantly increased the concentration of 5-HT and reduced VIP.CA significantly improved the diversity and abundance of the beneficial microbiome.Furthermore,the production of SCFAs[including acetic acid(AA),butyric acid(BA),propionic acid(PA)and valeric acid(VA)]was significantly promoted by CA.The changed abundance of Firmicutes,Akkermansia,Lachnoclostridium,Monoglobus,UCG.005,Paenalcaligenes,Psychrobacter and Acinetobacter were involved in the production of AA,BA,PA and VA.CONCLUSION CA could treat STC effectively by ameliorating the composition and abundance of the intestinal microbiome to regulate the production of SCFAs.

HPLC Determination of Harpagoside and Cinnamic Acid in Radix Scrophulariae

A gradient HPLC method was established for the determination of harpagoside and cinnamic acid in Radix Scrophulariae (Xuanshen) and a proposition was put forward for the lowest content of the characteristic and active constituent (harpagoside) for qualified Radix Scrophulariae. The experimental conditions were as follows: Ultrasphere ODS column (250 mm 4.6 mm, 5 mm), mobile phase: acetonitrile-water (containing 1.0% acetic acid) (20:8050:50) (20 min), flow-rate 1 mLmin-1, room temperature, detection wavelength 278 nm. Twenty-eight samples of Xuan-shen (Radix Scrophulariae) from different districts of China were analyzed and the contents of harpagoside and cinnamic acid in Xuan-shen were 0.041~0.244% and 0.012~0.068% respectively. The recoveries (RSD)% were 97.13(0.80)% for harpagoside and 99.38(0.51)% for cinnamic acid. The method is simple and accurate. It can be used for the quality control of Radix Scrophulariae. We propose that the content of harpagoside in qualified Radix Scrophularia should be no less than 0.05%.

Determination of Plasma Concentration of Cinnamic Acid by High-Performance Liquid Chromatography and Its Pharmacokinetics in Rats after Oral Administration of Zi-Shen Pill

Aim To develop a simple and sensitive high-performance liquid chromatographicmethod for determination of plasma concentration of cinnamic acid and pharmacokinetic study in ratsafter a single oral dose of traditional Chinese medicinal preparation Zi-Shen pill. Method Plasmasamples were acidified with hydrochloric acid and extracted with ethyl acetate . Cinnamic acid wasdetermined by HPLC using a G_(18) column. A mobile phase ofmethanbl-acetonitrile-water-triethyl-amine (7:22:73 = 0.2, V/V), with the pH adjusted to 4.0 withphosphoric acid, and with a UV detector set at 340 nm. Results The standard curve was linear overthe range of 1.92- 192.0 μg·mL^(-1). The LLOQ was 1.92 μg·mL^(-1) . The RSDs of within-day andbetween-day precision were < 8%. The mean recovery was 82.0% . Conclusion After validation, themethpd has been used to investigate the pharmacokinetic profiles of the traditional Chinesemedicinal preparation Zi-Shen pill.

Anticancer Activities of Substituted Cinnamic Acid Phenethyl Esters on Human Cancer Cell Lines

Caffeic acid phenethyl ester (CAPE) and sixteen substituted cinnamic acid phenethyl esters were prepared via conventional procedures in order to test their in vitro anticancer activities by either MTT assay or SRB assay on six different human cancer cell lines. The results indicated that in the concentration of 10 μmol·L -1 the lead compound CAPE possessed anticancer activities against human HL 60, Bel 7402, and Hela cell lines, and two other compounds possessed potent anticancer activities against Bel 7402 and Hela cell lines.

Thansgenic peanut plants obtained by particle bombardment via somatic embryogenesis regeneration system

After pre-culture and treatment of osmosis, cotyledons of immature peanut (Arachis hypogaea L.) zygotic embryos were transformed via particle bombardment with a plasmid containing a chimeric hph gene conferring resistance to hygromycin and a chimeric intron-gus gene. Selection for hygromycin resistant calluses and somatic embryos was initiated at 10th d post-bombardment on medium containing 10-25 mg/L hygromycin. Under continuous selection, hygromycin resistant plantlets were regenerated from somatic embryos and were recovered from nearly 1.6% of the bombarded cotyledons. The presence and integration of foreign DNA in regenerated hygromycin resistant plants was confirmed by PCR (polymerase chain reaction) for the intron-gus gene and by Southern hybridization of the hph gene. GUS enzyme activity was detected in leaflets from transgenic plants but not from control, non-transformed plants. The production of transgenic plants are mainly based on a newly improved somatic embryogenesis regeneration system developed by us.

Studies on the Syntheses and Properties of UV-sensitive Organosilicon Monomers and Polymers

Photosensitive organosilicon monomers and polymers containing furylacrylate, cinnamate or methacrylate groups were synthesized. The chemical structure of these organosilicon monomers were confirmed by 1H NMR and elemental analysis.The curing rates of these photosensitive polysiloxanes were also determined, all of them show a good UV-sensitivity. The UV-sensitivity of polysiloxanes containing pendent furylacrylates are comparable to that of polysiloxanes with either pendent cinnamate or pendent methacrylate groups.

Effects of Cinnamic Acid on Bacterial Community Diversity in Rhizosphere Soil of Cucumber Seedlings Under Salt Stress

To investigate the effects of a plant autotoxin, cinnamic acid, on bacterial communities in the rhizosphere soil of cucumber seedlings under salt stress, we used cucumber as the experimental material, cinnamic acid as the autotoxin, and NaCl to apply salt stress. Bacterial communities in the rhizosphere soil were analyzed using polymerase chain reaction （PCR）, denaturing gradient gel electrophoresis （DGGE）, and clone sequencing. Salt stress decreased the diversity of bacterial species in rhizosphere soil of cucumber seedlings at several growth stages. Cinnamic acid exacerbated the effects of salt stress at high concentrations, but alleviated its effects at low concentrations. Cloning and sequencing results indicated that DGGE bands amplified from soil samples showed high homology to uncultured bacterial species. Cinnamic acid at 50 mg kg^-1 soil improved cucumber growth and was the most effective treatment to alleviate the effects of salt stress on bacterial communities.

RP-HPLC Determination and Pharmacokinetic Comparison of Cinnamic Acid in Rat Plasma After Administration of Di-Gu-Pi Decoction and Pure Cinnamic Acid

A sensitive, simple, and accurate method was developed for the determination and pharmacokinetic comparison of cinnamic acid in rat plasma after the administration of a Traditional Chinese Medicinal preparation, Di-Gu-Pi decoction, and pure cinnamic acid using RP-HPLC. Di-Gu-Pi was extracted with 5% aqueous sodium bicarbonate, which was followed by purification with ion exchange column chromatography. The plasma samples taken from rats were deproteinized with methanol. The reversed-phase （HPLC） system with a Diamonsil C18 column and methanol-acetonitfile-water （8： 32： 60, volume ratio） （adjusted to pH = 3.0 with glacial acetic acid） as the mobile phase was employed for the separation of cinnamic acid in the plasma samples. The detection was set at 272 nm and 3-（p-fluoro-phenyl）-2-propenoic acid was chosen as the internal standard. The calibration curve was linear in a range from 0. 10 to 25.0μg/mL （R2 = 0. 9988, n = 9）. The precision was 3.42%-10. 10%; the between-day precision was 2. 84%-8.91% ; the accuracy was - 1.51%-1.26% ; the mean recovery was 99. 9%. The method was found to be sensitive, simple, accurate and appropriate for the determination of cinnamic acid.

Changes of chlorogenic acid content and its synthesis-associated genes expression in Xuehua pear fruit during development

According to synthetic pathway of plant chlorogenic acid （CGA）, the expression patterns of genes encoding enzymes that are associated with CGA synthesis were studied in normally developed Xuehua pear fruit. The study demonstrated that CGA content in peel and flesh of Xuehua pear decreased as fruit development progressed, with a higher level in peel. The expression levels of PbPAL 1, PbPAL2, PbC3H, PbC4H, Pb4CL 1, Pb4CL2, Pb4CL6, PbHC T1 and PbHC T3 genes decreased in fruit, which was consistent with the pattern of variation in CGA content. That indicated that these genes might be key genes for influencing fruit CGA synthesis in Xuehua pear. However, Pb4CL7 gene expression profile is not consistent with variation of CGA content, hence, it may not be a key gene involved in CGA synthesis.

Synthesis and Crystal Structure of (E)-4-(Benzyloxy)-2-(cinnamoyloxy)-N,N,N-trimethyl-4-oxobutan-1-aminium Chloride as a Double-prodrug

A novel hydrochloride quaternary ammonium salt （E）-4-（benzyloxy）-2-（cinnamo- yloxy）-N,N,N-trimethyl-4-oxobutan-l-aminium chloride （Cz3HzgNO4Cl2, Mr = 454.37） has been synthesized via the sequence of acetylation and esterification by using L-carnitine （L-4-N-trimethy- lammonium-3-hydroxybutyric acid, LC） and cinnamic acid as the starting materials, and its crystal structure was determined by single-crystal X-ray diffraction method. The crystal belongs to monoclinic, space group P212121 with a = 10.1670（4）, b = 10.4488（4）, c = 22.9795（11）A, V = 2441.18（18）A3, Z = 4, Dc = 1.236 g/cm3,μ（MoKa） = 0.293 mm-1, F（000） = 960, Flack factor = -0.01（11）, the final R = 0.0489 and wR = 0.1550 for 3350 observed reflections （I 〉 2σ（/）） and R = 0.0953 for all 5648 unique reflections. The crystal structure involves a conjugated system which shows a reverse olefin structure.

Synthesis and Luminescence of Complexes Eu_x Y_(1-x)(phen)L_3

A series of binuclear complexes with different molar ratio of europium to yttrium with cinnamic acid and o phenanthroline were synthesized in anhydrous alcohol. Elemental analysis shows that the composition of the complexes are Eu x Y 1- x (phen)L 3 (L: C 6H 5CH=CHCOO, x =1.0, 0.7, 0.5, 0.3 and 0.1). The IR absorption spectra indicate that cinnamate is coordinated to the rare earth ions and chemical bonds are formed between rare earth ions and nitrogen atoms of o phenanthroline. Fluorescent spectra show that the emission of Eu 3+ ion can be greatly enhanced if some of europium ions in the complexes are substituted by yttrium ions.

Isolation and Expression Analysis of Two Genes Encoding Cinnamate 4-Hydroxylase from Cotton(Gossypium hirsutum)

Two genes （GhC4H1 and GhC4H2） that encode putative cotton cinnamate 4-hydroxylases that catalyze the second step in the phenylpropanoid pathway were isolated from developing cotton fibers. GhC4H1 and GhC4H2 each contain open reading frames of 1 518 base pairs （bp） in length and both encode proteins consisting of 505 amino acid residues. They are 90.89% identical to each other at the amino acid sequence level and belong to class I of plant C4Hs. GhC4H1 and GhC4H2 genomic DNA are 2 247 and 2 161 bp long, respectively, and contain two introns located at conserved positions relative to the coding sequence. GhC4HI and GhC4H2 promoters were isolated and found to contain many cis-elements （boxes P, L and AC-1 element） previously identified in the promoters of other phenylpropanoid pathway genes. Histochemical staining showed GUS expression driven by the GhC4H1 and GhC4H2 promoters in ovules and fibers tissues. GhC4H1 and GhC4H2 were also widely expressed in other cotton tissues. GhC4H2 expression reached its highest level during the elongation stage of fiber development, whereas GhC4H1 expression increased during the secondary wall development period in cotton fibers. Our results contribute to a better understanding of the biochemical role of GhC4H1 and GhC4H2 in cotton fiber development.

A New Triterpene from the Orchid Pholidota yunnanensis

A new triterpene, 25-methylenecyclopholidonyl p-hydroxy-trans-cinnamate, was isolated from a orchid Pholidota yunnanensis. The structure elucidation and H, 1 13 C-NMR assignments were achieved by spectral and chemical method.

Synthesis and Characterization of Rare Earth Tesnary Complexes with Cinnamic Acid and O-Phenanthroline

Thirteen solid rare earth tesnary complexes with cinnamic acid C 6H 5CH=CHCOOH, HL and o phenanthroline (phen), RE(phen)L 3 were synthesized. Their IR absorption spectra, molar conductance, TG DTA, X ray power diffraction analysis and fluorescence spectra were studied. The results show that all coordination compounds are oxidized and decomposed around 400 ℃ to 540 ℃. They are all crystalline material. The fluorescence spectra indicate that the fluorescence emission intensity of Eu(phen)L 3 is the highest among them.

Effects of Exogenous Cinnamic Acids on the Growth and Physiological Characteristics of Cucumber Seedlings

In order to study the effects of exogenous cinnamic acids on plant growth, contents of photosynthetic pigment, root activities and ATPase activities of root membrane at cucumber seedling stage, the seedlings of Shandong Mici cucumber were tested. The results showed that seedlings growth, contents of photosynthetic pigment, root activities and ATPase activities of root membrane were inhibited by cinnamic acids. The growth and root activities of seedlings were significantly （P〈0.05） lower in the soil amended with 100 mg kg^-1 cinnamic acids compared to the control. The contents of chlorophyll a, chlorophyll a＋b and carotenoid of seedlings significantly （P〈0.05） decreased in the soil amended with 200 mg kg^-1 cinnamic acids, whereas ATPase activities exhibited a higher sensitivity and greatly decreased in the soil amended with 50 mg kg^-1 cinnamic acids. These results suggested that cinnamic acids could induce a stress condition, and the stress intensities increased with enhanced cinnamic acid concentration.

Synthesis of a magnetic-separated chitosan-palladium complex and its catalytic activity in the reaction of acrylic acid with iodobenzene

A magnetic-separated catalyst of chitosan-palladium complex （Fe3O-CS-Pd） based on chitosan coated Fe3O4 microspheres was prepared by the ＂bottom-up＂ approach. The catalytic behavior of the catalyst in the cross coupling reaction of acrylic acid （AA） with iodobenzene （ArI） was investigated. Compared with the traditional homogeneous palladium catalysts, the catalyst was easily separated and reused.

TWO NEW CINNAMIC ACID DERIVATIVES FROM MAGNOLIA BIONDII PAMP

Two new cinnamic acid derivatives named biondinin C and biondinin D were isolated from the flower buds of Magnolia biondii pamp. The structures were elucidated by the spectral data including ~1H, ~1H COSY, ~1H-^(13)C COSY spectra.

A 3D Homochiral Mn(Ⅱ) Coordination Polymer Based on the Ligand 2,2'-(Ethane-1,2-diylbis(oxy)) Dicinnamic Acid

A 3D homochiral coordination polymer [Mn（edca）]n（1） was synthesized from a flexible coupled cinnamic acid ligand, 2,2？-（ethane-1,2-diylbis（oxy）） dicinnamic acid（H_2 edca） and MnCl_2×4 H_2 O under solvothermal conditions. The complex crystallizes in orthorhombic, space group P2_12_12_1 with a = 5.5785（8）, b = 13.0393（18）, c = 23.133（3） A, V = 1682.7（4） A^3, M_r = 407.27, D_c = 1.608 Mg/cm^3, F（000） = 836, Z = 4, the final R = 0.0240 and wR = 0.0590 for 2983 observed reflections（I 〉 2σ（I））. In 1, the edca2＋ anions alternately bridge the Mn（Ⅱ） cations to form one-dimensional（1 D） infinite helical chains of [Mn（edca）]n, which are further connected by the ligands generating a three-dimensional（3D） homochiral network. The photoluminescence of 1 was also investigated in solid state at ambient temperature.

NMR used to study the side-reactions between peroxides and antioxidants during the reactive extrusion process of the impact polypropylene

Side reaction pathways are observed to occur between antioxidants and peroxide during the processing of multiple resin grades mediated by controlled peroxide-induced degradation of impact polypropylene.In the present work,the reaction mechanism and main by-products between antioxidants and peroxides were investigated.The results demonstrate that peroxides greatly accelerate the decomposition reactions,and the free radicals formed from peroxide decomposition react with,for example,the antioxidant AO1010 to produce dehydrogenation of phenyl propionic unit(s)at the a position(cinnamic acid ester moiety),which generates a conjugated system leading to the increased color of the product.It is the first time to confirm the cinnamic acid moiety's existence and report its NMR data.Further,this work confirms the dehydrogenation mechanism by comparison with different sterically hindered phenolic antioxidants.It also systematically summarizes the oxidation and degradation mechanism of AO168 and AO1010 under air and peroxide environments,respectively.Based on present study,clear guidelines are obtained to improve the quality of polymeric products,especially the appearance and stability,during product development.