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.

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.

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.

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.

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 Novel Chiral Cd-organic Network Based on Flexible Coupled Cinnamic Acid

A new metal-organic network, [Cd（CH_3OH）_2（epa）]_n（1）, was synthesized from an achiral coupled cinnamic acid, 3,3？-（（ethane-1,2-diylbis（oxy））bis（2,1-phenylene））diacrylic acid（H_2epa）, and Cd（NO3）2·4H2O under solvothermal conditions. The complex crystallizes in orthorhombic, space group P2_12_12 with a = 9.8286（8）, b = 21.0004（16）, c = 5.5169（4） A, V = 1138.71（15） A3, M_r = 528.81, D_c = 1.542 Mg/cm3, F（000） = 536, Z = 2, the final R = 0.0345 and wR = 0.1101 for 2006 observed reflections（I 〉 2σ（I））. In 1 the epa^（2＋） anions alternately bridge the Cd（II） cations to form a one-dimensional（1D） infinite homochiral helical chain of [Cd（epa）]n. The chiral homohelical chains via hydrogen bonds formed a two-dimensional（2D） network. The photoluminescence of 1 was also investigated in solid state at ambient temperature.

Determination of Cinnamic Acid in Stephania longa Lour. by HPLC

[Objectives] To establish a HPLC method for the quantitative determination of cinnamic acid in Stephania longa Lour. [Methods]The chromatographic column: Thermo BDS HYPERSIL C_(18)( 4. 6 mm × 250 mm,5 μm); mobile phase: acetonitrile-0. 1% phosphoric acid( 24∶ 76); flow rate: 1 mL/min; column temperature: 30℃; wavelength: 285 nm. [Results]The cinnamic acid was in a good linear relationship in the range of 0. 021 7-0. 076 μg,the sample recovery rate was 100. 46%,the RSD was 2. 20%,and the content was in the range of 0. 004%-0. 022%. [Conclusions] The method is simple,accurate and reproducible,and can be used for the quality control of S. longa Lour.

Simultaneous Determination of Gallic Acid and Cinnamic Acid Content in Rhubarb by HPLC

[Objective]The paper was to determine the contents of gallic acid and cinnamic acid in Chinese herb rhubarb by HPLC.[Method]High performance liquid chromatography(HPLC)was established with the following conditions:Thermo SCIENTIFIC Hypersil GOLD Dim column(4.6 mm×250 mm,5μm),mobile phase methanol-0.1%phosphoric acid solution,gradient elution,detection wavelength 278 nm,flow rate 1.0 mL/min,column temperature 30℃,injection volume 10 pL.[Result]The content of gallic acid and cinnamic acid in rhubarb was determined by HPLC,and they showed good linear relationship in the linear ranges of 0.125-1.250 pg(E2=0.9998)and 0.0382-0.3820μg(E2=0.9994),respectively.[Conclusion]A HPLC method is established to determine gallic acid and cinnamic acid content in rhubarb.The method will provide a scientific basis for quality control of rhubarb and its traditional Chinese medicine.

Combined Effects of Dietary Bacillus subtilis and Trans-cinnamic Acid on Growth Performance,Whole Body Compositions,Digestive Enzymes and Intestinal bacteria in Rainbow Trout(Oncorhynchus mykiss)

In this study,the combined effects of dietary Bacillus subtilis(BS,107 g/cfu)and different levels(0.025%,0.050%,0.075%and 0.150%)of trans-cinnamic acid(CA)on fish growth performance,whole body compositions,digestive enzymes,intestinal bacteria and internal organ index of rainbow trout(Oncorhynchus mykiss)were investigated.Six different experimental groups including control group(C),C+BS,0.025%CA+BS,0.050%CA+BS,0.075CA+BS,0.150%CA+BS)were established.According to the results obtained,growth performance,whole body compositions and digestive pH were not statistically significant among groups.Further,no significant differences were found between experimental groups in terms of the intestinal enzymes(trypsin,alkaline phosphatase and lipase)and gastric pepsin.Significantly higher levels of intestinal amylase were found in the control+BS,0.025%CA+BS,0.050%CA+BS,and 0.075%CA+BS compared to the control and 0.150%CA+BS groups.Moreover,coliform and Enterobacteriaceae counts were highest in the control+B.subtilis and lowest in the 0.150%CA+B.subtilis groups.

Microwave-assisted base-free synthesis of trans-cinnamic acids using hypervalent iodonium salts

A fast and convenient base-free Heck reaction of acrylic acid with hypervalent iodonium salts was achieved under microwave irradiation in water, providing a simple method for the synthesis of trans-cinnanfic acids in good yields in short time.

Analysis of the <i>trans</i>-Cinnamic Acid Content in <i>Cinnamomum spp.</i>and Commercial Cinnamon Powder Using HPLC

The present study aimed to quantify the content of trans-cinnamic acid (CA) in Cinnamomum japonicum, C. loureirii, and C. camphora and the commercial application of CA using high performance liquid chromatography (HPLC). A C18 column was used, with water/methanol as the mobile phase gradient. The highest content of CA was observed in the bark of C. loureirii (16.97 mg/g) and cinnamon powder A (47.60 mg/g). The lowest content of CA was observed in leaf and heartwood of C. japonicum (0.10 and 0.10 mg/g, respectively) and cinnamon powder C (22.87 mg/g). This result could be utilized as a guideline for the analysis of the commercial applications of Cinnamomum.

New Process for the Synthesis of A Sun-screening Agent Isooctyl P-methoxy Cinnamate

A sun-screening agent isooctyl p-methoxy cinnamate was prepared by reaction of p-methoxyl benzaldehyde with isooctyl acetate using titanium tetrachloride as catalyst. The optimum conditions are as follows： molar ratio of p-methoxyl benzaldehyde to isooctyl acetate and titanium tetrachloride is 1 ： 1.1 ： 0.5; reaction temperature is 30℃; and reaction time is 6 h. The yield of isooctyl p-methoxy cinnamate can reach 98%. The method of the synthesis of isooctyl p-methoxy cinnamate is efficient and economical.

引入逆向思维和设计理念的有机合成实验教学改革——以基于逆合成分析法的肉桂酸合成为例

以经典有机化学实验项目——肉桂酸的合成为例,介绍在有机合成实验教学中引入逆向思维的教学设计,经改进后,实验融入了丰富的思政元素,逆向推理思维模式的引入,避免了“照方抓药”式的实验教学;学生通过探究多条合成路线构建目标分子,进一步加深了对有机合成内涵的理解;本项目融入了三项诺贝尔化学奖成果,确保了教学内容的前沿性和先进性。

N-(苯乙基)肉桂酰胺类化合物的合成及其抗氧化活性研究

植物N-(苯乙基)肉桂酰胺类化合物是一类重要的酰胺类活性成分,为寻求更高药理活性的肉桂酰胺类先导化合物,以苯甲醛、丙二酸为原料,设计合成了9种N-(苯乙基)肉桂酰胺类化合物,结构经过^(1)H NMR、^(13)C NMR、IR和MS鉴定。以抗坏血酸为对照,测定9种化合物清除·OH、DPPH·及ABTS+·的效果。抗氧化实验结果表明,部分化合物对·OH的清除效果优于抗坏血酸;9种化合物具有一定清除DPPH·及ABTS+·的能力,但效果不如抗坏血酸。该类化合物可进一步结构优化,探究其抗阿尔茨海默病、抗肿瘤等活性研究,也可作为抗氧化剂应用于食品、药品领域。