P-methoxycinnamic Acid Research Articles

The Milling Method in Formation of Inclusion Complex p-Methoxycinnamic Acid-Hydroxypropyl-β-Cyclodextrin.

p-methoxycinnamic acid (pMCA) is a substance with several pharmacological activities, derived from the rhizome of Kaempferia galanga Linn. The solubility of pMCA can be increased by the formation of inclusion complexes (IC) using hydroxypropyl-βcyclodextrin (HPβCD) compounds. IC are obtained through the milling method, which is a simple, environmentally friendly, and low-cost manufacturing method. The process involves the pounding of material with a certain speed and impact force. This research aims to characterize the pMCA-HPβCD IC made using the milling method. Milling the mixture of pMCA and HPβCD using a ball mill is a common technique to enhance the formation of the inclusion complex. The IC’s physical characteristics were analyzed in terms of their morphology, particle size, crystallinity, and thermal properties. The dissolution profile was also performed using paddle-typed dissolution apparatus (Type II) with 500 mL distilled water as dissolution medium. The amount of pMCA dissolved was determined using UV spectrophotometry. The dissolution parameter was determined as dissolution efficiency at 60 minutes (DE60). The IC particles were irregular in shapes and porous. The size was reduced as compared to the individual components. The XRD revealed that the ICs were amorphous. The DE60 of IC increased by a factor of 4.3 compared to the pure pMCA. In conclusion, the milling method successfully formed complex of pMCA-HPβCD with different characteristics from the initial compound and was significantly increased the percentage of the dissolved pMCA.

Effects of postbiotics on chronic diarrhea in young adults: a randomized, double-blind, placebo-controlled crossover trial assessing clinical symptoms, gut microbiota, and metabolite profiles.

Chronic diarrhea has a considerable impact on quality of life. This randomized, double-blind, placebo-controlled crossover intervention trial was conducted with 69 participants (36 in Group A, 33 in Group B), aiming to investigate the potential of postbiotics in alleviating diarrhea-associated symptoms. Participants received postbiotic Probio-Eco® and placebo for 21 days each in alternating order, with a 14-day washout period between interventions. The results showed that postbiotic intake resulted in significant improvements in Bristol stool scale score, defecation frequency, urgency, and anxiety. Moreover, the postbiotic intervention increased beneficial intestinal bacteria, including Dysosmobacter welbionis and Faecalibacterium prausnitzii, while reducing potential pathogens like Megamonas funiformis. The levels of gut Microviridae notably increased. Non-targeted metabolomics analysis revealed postbiotic-driven enrichment of beneficial metabolites, including α-linolenic acid and p-methoxycinnamic acid, and reduction of diarrhea-associated metabolites, including theophylline, piperine, capsaicin, and phenylalanine. Targeted metabolomics confirmed a significant increase in fecal butyric acid after postbiotic intervention. The levels of aromatic amino acids, phenylalanine and tryptophan, and their related metabolites, 5-hydroxytryptophan and kynurenine, decreased after the postbiotic intervention, suggesting diarrhea alleviation was through modulating the tryptophan-5-hydroxytryptamine and tryptophan-kynurenine pathways. Additionally, chenodeoxycholic acid, a diarrhea-linked primary bile acid, decreased substantially. In conclusion, postbiotics have shown promise in relieving chronic diarrhea.

Phytochemical Profiles and Antimicrobial Activity of Selected Populus spp. Bud Extracts.

Buds of poplar trees (Populus species) are often covered with sticky, usually polyphenol-rich, exudates. Moreover, accessible data showed that some Populus bud extracts may be excellent antibacterial agents, especially against Gram-positive bacteria. Due to the fragmentary nature of the data found, we conducted a systematic screening study. The antimicrobial activity of two extract types (semi-polar-ethanolic and polar-ethanolic-water (50/50; V/V)) from 27 bud samples of different poplar taxons were compared. Antimicrobial assays were performed against Gram-positive (five strains) and Gram-negative (six strains) bacteria as well as fungi (three strains) and covered the determination of minimal inhibitory, bactericidal, and fungicidal concentrations. The composition of extracts was later investigated by ultra-high-performance liquid chromatography coupled with ultraviolet detection (UHPLC-DAD) and with electrospray-quadrupole-time-of-flight tandem mass spectrometry (UHPLC-ESI-qTOF-MS). As a result, most of the extracts exhibited good (MIC ≤ 62.5 µg/mL) or moderate (62.5 < MIC ≤ 500 µg/mL) activity against Gram-positives and Helicobacter pylori, as well as fungi. The most active were ethanolic extracts from P. trichocarpa, P. trichocarpa clone 'Robusta', and P. tacamahaca × P. trichocarpa. The strongest activity was observed for P. tacamahaca × P. trichocarpa. Antibacterial activity was supposedly connected with the abundant presence of flavonoids (pinobanksin, pinobanksin 3-acetate, chrysin, pinocembrin, galangin, isosakuranetin dihydrochalcone, pinocembrin dihydrochalcone, and 2',6'-dihydroxy-4'-methoxydihydrochalcone), hydroxycinnamic acids monoesters (p-methoxycinnamic acid cinnamyl ester, caffeic acid phenethylate and different isomers of prenyl esters), and some minor components (balsacones).

Bioconjugation of Vegetable Oils with UV Absorbers: New Approach in Skin Photoprotection.

We reported the tunable synthesis of new vegetable oil-UV filter bioconjugates using sea buckthorn oil (SBO) and p-methoxycinnamic acid (p-MCA) as an alternative to the common UV filter, ethylhexyl-p-methoxycinnamate (octinoxate). The synthetic strategy is based on the sustainable ring-opening reaction of epoxidized SBO with p-MCA in heterogenous catalysis in eco-friendly solvents. The amount of UV-absorptive moieties grafted on the triglyceride backbone is controlled by different epoxidation degrees as determined by NMR spectroscopy. The performance of the new UV-absorber bioconjugates was assessed by in vitro sun protection factor (SPF) measurements after inclusion in SBO-ethylcellulose (EC) oleogels and comparison with the SPF value of the SBO-EC-octinoxate oleogel with equivalent p-MCA acid moieties (10% wt/wt). The concentration obtained for the SBO-EC oleogel formulated with the bioconjugate with the lowest degree of functionalization, namely 55%, represents 45% of the SPF determined for the SBO-EC-octinoxate oleogel, regardless of the concentration of measured solutions. The new concept of vegetable oil-UV-absorber bioconjugates has potential UV-B photoprotective properties when included in oleogel formulations and deserves further investigation of their properties and stability including association with UV-A absorbers, respectively.

Optimization of Reaction Condition for Synthesis of 4-Methoxychalcone from Ethyl p-methoxycinnamate

Ethyl p-methoxycinnamate (1) is the main secondary metabolite found in Kaempferia galanga Linn and has various interesting pharmacological activities, including anti-inflammatory, sedative, vasorelaxant, and antiangiogenic activities. This study aimed to optimize the conditions for the conversion of 1 to 4-methoxychalcone (2) using a conventional synthetic reaction. The conversion was initiated by the hydrolysis of 1 to p-methoxycinnamic acid (3) and 3 to 4-methoxybenzaldehyde (4), and continued with the Claisen-Schmidt reaction of 4 with acetophenone (5). The temperature (room temperature and 45 °C) and ratio of 4 to 5 (1:1 and 1:2) were varied to determine the optimal conditions for the reaction. The results suggested that the reaction of 4 with 5 gave the best yield (42.1 %) when conducted at room temperature in a ratio of 4 to 5 (1:1). The structure of the reaction product was elucidated by spectroscopic analysis and compared with previously published data

The dissolution of p-methoxycinnamic acid-β-cyclodextrin inclusion complex produced with microwave irradiation.

p-methoxycinnamic acid (pMCA) is an ethyl pmethoxycinnamic derivative, which is the largest active ingredient in the rhizome of the kencur (Kaempferia galanga L) plant. Several studies reported that the compound has anti-inflammatory activity but has low solubility in water. The formation of a pMCA-β- cyclodextrin (βCD) inclusion complex with a molar ratio of 1:1 can increase its solubility. The formation of inclusion complexes with conventional methods requires a long time and the yield value is not optimal. This study aims to evaluate the dissolution of the pMCA-βCD inclusion complex produced using the microwave irradiation method. The product was manufactured with chloroform solvent and a power of 400 watts (power 80%). It was then evaluated using the Differential Thermal Analysis (DTA) every 2 minutes until the 8th minute. The reaction was complete after 4 minutes of treatment with a yield of 96.5%. The obtained inclusion complexes were evaluated using DTA, FTIR, and PXRD. Subsequently, a dissolution test was carried out using a type 2 apparatus in distilled water medium of pH 6.8±0.05 at 37±0.5°C. The results showed that there was a change in the melting temperature profile, infrared spectra, and crystallinity of the product. An 89.18% dissolution was also obtained within 60 minutes, which was twice that of pMCA compounds. From the results of the study, it can be concluded that the formation of pMCA-βCD inclusion complexes using the microwave irradiation method is capable of providing high-yield values in a short time.

Penetration study of p-methoxycinnamic acid (PMCA) in nanostructured lipid carrier, solid lipid nanoparticles, and simple cream into the rat skin

This study compared the ability of Nanostructured Lipid Carrier (NLC), Solid Lipid Nanoparticles (SLN), and Cream systems in delivering para Methoxycinnamic Acid (PMCA) to the dermis layer of the skin. Wistar rats were used as research subjects. NLC and SLN were made by applying the high shear homogenization method. Nile red was used as a penetration indicator based on its fluorescence. The interaction between fluorescence labeled NLC, SLN, or Cream and rat skin was visualized by fluorescence microscopy. Observations were made after 2 and 4.5 h of smearing the test sample. From the observations, it was known that the system/lipid base could penetrate the stratum corneum for delivering drugs. Penetration speed differs among systems as does the number of PMCAs that can be delivered. In this study, it can be concluded that the NLC system is able to deliver PMCA more quickly and in greater quantities to the dermis than SLN and Cream.

Synthesis of PMCA (P-Methoxy Cinnamic Acid) using Perkin Reaction and Its Activity as Photo Protective and Antifungal Agent

&lt;p class="Standard"&gt;&lt;span&gt;This study aimed to synthesize p-methoxy cinnamic acid through the Perkin reaction and to determine its activity as a photoprotective and antifungal agent against Candida albicans. The PMCA compound was synthesized by reacting p-methoxy benzaldehyde with acetic anhydride using a sodium acetate catalyst in a sonicator at 50oC for 60 minutes. The synthesized was a white precipitate with a % yield of 2.09% and a melting point of 172-175&lt;sup&gt;o&lt;/sup&gt;C. ATR-FTIR identified this compound with several functional groups, C=O, OH carboxylic acid, para-substituted benzene, and C=C. Analysis by GC-MS showed a single peak at a retention time of 11.710 minutes with m/z 178. Characterization of this compound by 1H-NMR spectrometry showed several chemical shifts showing the presence of OH groups of carboxylic acids, C=C groups, aromatic benzene groups, and methoxy. The results of this characterization indicated that the synthesis product was PMCA. The antioxidant activity of PMCA using the DPPH radical gave IC50 at a concentration of 352.6138 ppm. In vitro sunscreen activity against PMCA compounds provided high protection at a concentration of 30 ppm with SPF 32,505. The antifungal activity against Candida albicans showed inhibition zones of 0.257cm± 0.044, 1.397cm± 0.093, and 1.533cm± 0.111, respectively at concentrations of 5%, 10%, and 15%. The PMCA compounds can be synthesized through the Perkin reaction assisted by ultrasonic waves and can potentially be photoprotective and antifungal agents.&lt;/span&gt;&lt;/p&gt;

Preparation and Physicochemical Characterizations of p-Methoxycinnamic acid – Succinic Acid Cocrystal by Solvent Evaporation Technique

Background: PMCA (p-Methoxycinnamic acid) is an active pharmaceutical ingredient derived from Kaempheria galanga L (known as kencur in Indonesia), which is poorly soluble in water. It can cause problems in the development of pharmaceutical dosage forms. Several methods have been carried out to increase the solubility of PMCA such as complex formation with β-cyclodextrin, or solid dispersion. The cocrystal formation method is a solubility enhancement method that has been developed recently.&#x0D; Aim: The aim of the study was the preparation and physicochemical characterization of PMCA co-crystal with succinic acid (SA) as its conformer by solvent evaporation technique.&#x0D; Methods: PMCA-SA cocrystal was made by the solvent evaporation method with a 1:1 molar ratio. Physicochemical characterization of PMCA and SA cocrystal was performed by differential scanning calorimetry (DSC), powder X-ray diffraction (PXRD), and scanning electron microscope (SEM).&#x0D; Results: The DSC thermogram showed a decrease in the melting point of cocrystal compared to PMCA (173.55˚C), SA (187.55˚C), and its physical mixture (159.53˚C). The cocrystal thermogram displayed an endothermic peak at 158.46 ° C. Diffractogram of PMCA- SA cocrystal exhibited new diffraction peaks at an angle of 2θ = 21.92; 25.91 and 39.25˚ which was not found in the diffractogram of every single component nor its physical mixture. SEM photomicrograph showed PMCA-SA cocrystal as a rod-shaped crystal that had a different surface morphology and smaller size than the constituent materials.&#x0D; Conclusions: Based on the physicochemical characterization data above, it could be ascertained that PMCA-SA cocrystals had formed, these cocrystals were expected to increase the solubility of PMCA in water.

P-Methoxycinnamic acid disturbs cellular respiration and increases the lignification of Euphorbia heterophylla roots

Herbicide-resistant plants evolved rapidly due to the recurrent use of active principles with only a few mechanisms of action. Today, discovering new herbicides is a pressing challenge. Here, the effects of p-methoxycinnamic acid were evaluated on root growth, cellular respiration, and lignification of the wild poinsettia weed (Euphorbia heterophylla L.). In primary roots, p-methoxycinnamic acid decreased root length and the mitotic index, followed by the loss of cell viability. At the cellular level, p-methoxycinnamic acid stimulated KCN-insensitive and KCN- and SHAM-insensitive respiration. Furthermore, it decreased KCN-sensitive respiration and ATP generation, a limiting factor for root growth. Disturbances in cellular respiration increased the H2O2 content and superoxide dismutase, catalase, and soluble peroxidase activity. p-Methoxycinnamic acid increased the activities of phenylalanine ammonia-lyase and cell wall-bound peroxidase. It also increased lignin, ferulic and p-coumaric acids, and cell wall-esterified p-methoxycinnamic acid. Collectively, these findings reveal the phytotoxic potential of p-methoxycinnamic acid on wild poinsettia. Field tests may point to new clues for using this compound as a potential herbicide.

Anxiolytic effects, metabolism and plasma pharmacokinetics of 3, 6′ -disinapoylsucrose

3,6′-disinapoylsucrose (DISS) is a bioactive oligosaccharide ester derived from Polygalae Radix. This study aims to explore the anxiolytic effects of DISS and further reveal the material basis by establishing the pharmacokinetics of DISS and its metabolites. Behavioral experiments such as the open field test (OFT) and elevated plus maze test (EPM) were performed to evaluate the anxiolytic effects of DISS in mice after oral administration. By UPLC-MS/MS analysis, DISS and its metabolites both in blood and cerebrospinal fluid were identified, and the pharmacokinetics of DISS and its metabolites were characterized in SD rats after oral administration of DISS (100 mg·kg−1). Oral DISS could increase the time and frequency of mice entering the central area of the field in OFT and open arm in EPM, which indicated DISS has good anxiolytic effects. We also identified DISS and its metabolites (sinapic acid (SA), 3,4,5-trimethoxycinnamic acid (TMCA), methyl-3,4,5-trimethoxycinnamate (TMCA-CH2), p-Coumaric acid (CA) and p-methoxycinnamic acid (MA)) in rat plasma and cerebrospinal fluid. The pharmacokinetic results showed that DISS was rapidly absorbed after administration and reached its highest concentration at 12 min, SA had the highest exposure level in vivo and was probably the main active form of DISS action, TMCA could maintain at a low concentration for a long time. In brief, we reported the anxiolytic effect of DISS firstly, revealed the cerebrospinal fluid distribution and pharmacokinetics of DISS and its metabolites. Our findings provide the basis for further insight into the mechanisms involved in the anxiolytic effects of DISS.

Diterpenoids and p-methoxycinnamic acid diol esters from Kaempferia saraburiensis Picheans. (Zingiberaceae): Structural assignment of saraburol and their biological activities

Five undescribed compounds, including three diterpenoids namely, saraburol, saraburanes A and B, and two p-methoxycinnamic acid monoterpene diol esters, named E/Z-saraburinic esters, together with ten known oxygenated isopimarane diterpenoids, were isolated from the whole plant of Kaempferia saraburiensis Picheans. Among these compounds, saraburol possesses an unusual 6/9/6 tricyclic ring system bearing a 1,3-dioxonane-4-one scaffold, which is rarely found in natural products. The structure of isolated compounds was elucidated by spectroscopic methods, including HRESIMS, FTIR, 1D and 2D-NMR, and by comparison with published data, and their absolute configurations were determined by comparison of experimental with calculated ECD spectra and hydrolysis reaction. Using gauge-independent atomic orbital (GIAO) NMR shift calculations coupled with DP4+ probability analyses, biogenetic considerations, and optical rotation allowed for the complete characterization of saraburol. A plausible biosynthetic pathway for saraburol and saraburane A was proposed. The cytotoxicity result indicated that E-saraburinic ester exhibited the most potent activity with an IC50 value of 12.0 μM against MOLT-3 cells with a selectivity index of 12.5. Saraburane B exhibited the most potent activity against Gram-positive bacteria strain Staphylococcus epidermidis with MIC (MBC) value of 25 (50) μg/mL.

Solventless esterification of glycerol with p-methoxycinnamic acid catalyzed by a novel sulfonic acid mesoporous solid: Reaction kinetics

As a way to valorise glycerol, the main by-product of biodiesel, this study is focused on the production of esters of p-methoxycinnamic acid and glycerol. These esters can replace hazardous octylmethoxycinnamate in the cosmetic industry, which is thought to act as an endocrine disruptor and can interfere with thyroid function. Several sulfonated mesoporous catalysts, with and without endcapping, were easily synthetized using several alcohols as porogens. These catalysts were characterized for structure and surface area, chemical composition and acidity, and tested under solventless conditions for the esterification of glycerol with p-methoxycinnamic acid. Their activity was similar to that of p-toluenesulfonic acid. The best catalysts for the reaction under study was the end-capped mesoporous solid prepared in isopropanol. Finally, the selected catalyst was tested in 9 runs conducted at 150–170 °C and at molar ratios glycerol:p-methoxycinnamic acid ranging from 3:1 to 9:1. The kinetic model that better fits to the experimental data comprises two esterification reactions in-series and a first-order catalyst deactivation. The activation energies were 87.33 ± 5.67 kJ mol−1 for the average esterification to the monoglycerides, 69.17 ± 9.84 kJ mol−1 in average for the reactions yielding the diglycerides, and 104.00 ± 15.30 kJ mol−1 for the catalyst deactivation.

Anti-atherosclerotic Activity of Para Methoxy Cinnamic Acid in High Fat Diet Induced Hyperlipidemia Model Rats.

Hypercholesterolemia is a well-known etiological feature for cardiovascular diseases and a common indication of maximum categories of metabolic disorders. Para methoxy cinnamic acid is one of the cinnamic acid derivatives as a natural product obtained from the rice bran oil as an active constituent and has the antioxidant property. The present study was designed to evaluate the hypolipidemic activity of P-methoxy cinnamic acid against high fat diet induced hyperlipidemia in experimental rats. Male Wistar albino rats were divided into five groups (n = 6), and high fat diet was used to induce the hyperlipidemia for 28days. P-methoxy cinnamic acid was used in two different doses (40 and 80mg/kg body weight), and they were administered orally to the rats for 28days during high fat diet. Atorvastatin (5mg/kg) was used as reference standard. A significant elevated level of lipid abnormalities and tissue antioxidant parameters were reversed from normal level by the treatment of P-methoxy cinnamic acid in both the doses. Histopathological evidence further supported the protective action. Based on the initial findings, it was concluded that P-methoxy cinnamic acid was able to offer significant protection against high fat diet induced atherosclerosis. Future studies were recommended to identify the molecular mechanism of P-methoxy cinnamic acid against atherosclerosis protection.

Comparison of the Release rate, Penetration and Physical stability of p-Methoxycinamic acid (PMCA) in Nanostructured Lipid Carriers (NLC), Solid Lipid Nanoparticle (SLN) and Nanoemulsion (NE) systems

Objective: The p-methoxycinnamic acid (PMCA) was known has antiinflamatory effect which is difficult to dissolve in water, to increase the penetration to the skin it’s was loaded in the nanostructured lipid carrier (NLC) delivery system used the combination of beeswax-cacao oleum and virgin coconut oil (VCO), compared with solid lipid nanoparticle (SLN) and nanoemulsion (NE) delivery systems. Material and Method: PMCA concentrations of 1% in each system were prepared by the high shear homogenization method, namely NLC-PMCA and SLN-PMCA; and was prepared by emulsification method namely NE-PMCA. Then all systems are characterized and tested for release rate, penetration into the rat skin, also were tested for physical stability. The results of this research: All systems have a pH value in the range of 4.2 - 4.5 which falls into the skin's pH range (4-6.5). The viscosity of the NLC-PMCA, SLN-PMCA and NE-PMCA systems are 30.03±6.29; 93.77± 6.11 and 3.43±0.16 cPs, respectively. The particle size of NLC-PMCA, SLN-PMCA and NE-PMCA are 423.6± 33.6; 830.7±71.3 and 57.1±1.6nm, respectively. The release rate of PMCA in the NLC-PMCA, SLN-PMCA and NE-PMCA system are 0.2210±0.0089; 0.1972±0.0145 and 0.4690±0.0228µg/cm2/minute, respectively. The depth of PMCA penetration in the NLC-PMCA, SLN-PMCA and NE-PMCA system at 30 minutes after application are 1173.0±37.8; 703.3±117.2; 1414.3±106.4µm, respectively and at 2 hours after application are 1268.8±111.9; 945.6±140.4; 1832.5±92.8μm, respectively. The NLC-PMCA has no physical changes in 14 days’ storage, whereas the SLN-PMCA consistency becomes thicker and the NE-PMCA becomes turbid. Conclusion: NLC-PMCA has better release rate and deeper penetration than SLN-PMCA, even though it is lower and shallower than NE-PMCA, but NLC-PMCA has better physical stability than SLN-PMCA and NE-PMCA.

THE CHEMOTHERAPEUTIC ROLE OF p-MCA IN AVERTING NDEA INDUCED HEPATIC CARCINOGENESIS IN EXPERIMENTAL WISTAR RATS

OBJECTIVES: Hepatocellular carcinoma (HCC) is the primary liver cancer and second leading cause of cancer related deaths worldwide. The aim of this present study was to evaluate the biochemical, histopathological and chemotherapeutic efcacy of p-methoxycinnamic acid (p-MCA) against N- nitrosodiethylamine (NDEA) in a rat model of hepatocellular carcinoma. MATERIALS AND METHODS: Approximately thirty male wistar rats weighing 150-200 g were designated for this study. The rats were arbitrarily separated into ve groups and each group comprised of six rats. Group 1 served as control; Group 2 rats received p-MCA at the dose of 80 mg/kg b.w. Group 3, 4 and 5 rats were induced HCC using NDEA. 2-acetylaminouorene (AAF) was used as a promotor. Group 4 and 5 rats received p-MCA at the doses of 40 and 80 mg/kg b.w. throughout the 12 week experimental period. At the end of the experimental period, liver tissues from all the rats were collected and liver specic enzymes, lipid peroxidation, markers, xenobiotic metabolizing enzymes, antioxidant status and brotic markers were evaluated.RESULTS: NDEA administration induced hepatocyte damage, oxidative stress, cell proliferation, inammation and brosis. The liver sections from NDEA induced group 3 rats showed loss of lobular architecture, morphological changes in the nuclei and DNA damage. Administration of p-MCA to NDEA treated rats restored the hepatic architecture, enzyme activities, cell proliferation, inammation and brosis.CONCLUSION: We conclude that oral administration of p-MCA for 12 weeks exerts a signicant therapeutic effect against HCC by regulating the concentration of specic hepatic and xenobiotic enzymes, suppressing oxidative stress, inhibiting cell proliferation and reducing the inammatory response.

The thermodynamic study of p-methoxycinnamic acid inclusion complex formation, using β-cyclodextrin and hydroxypropyl-β-cyclodextrin.

Cyclodextrin's ability to form an inclusion complex with a guest molecule is a function of two factors. The first is steric and depends on the relative size of cyclodextrin cavity to the guest molecule, while the second is the thermodynamic interaction between the different system components. This study therefore aims to determine the effect of β-cyclodextrin and hydroxypropyl-β-cyclodextrin as complex formers, on thermodynamic parameter values (ΔH, ΔG, and ΔS) in the formation of inclusion complex with p-methoxycinnamic acid (pMCA). The pMCA complex formation with β-cyclodextrin or hydroxypropyl-β-cyclodextrin was determined in 0.02 pH 4.0M acetate buffer and 0.02M pH 7.0 phosphate buffer, with a 0.2 µ value at 32, 37, and 42±0.5°C. This experiment was carried out in a waterbath shaker until a saturated solution was obtained. Subsequently, pMCA concentration was determined using UV spectrophotometer at the maximum pMCA wavelength, at each pH. The result showed pMCA formed inclusion complex with β-cyclodextrin or hydroxypropyl-β-cyclodextrin and exhibited increased solubility with increase in β-cyclodextrin or hydroxypropyl-β-cyclodextrin concentration. This temperature rise led to a decrease in the complex's constant stability (K). Furthermore, the interaction showed a negative enthalpy (∆H<0) and is a spontaneous processes (∆G<0). At pH 4.0, an increase in the system's entropy occurred (∆S>0), however, at pH 7.0, the system's entropy decreased (∆S<0). The rise in pMCA solubility with increase in cyclodextrin solution concentration indicates an inclusion complex has been formed, and is supported by thermodynamic data.

Recent Developments in Therapeutic and Nutraceutical Applications of p-Methoxycinnamic Acid from Plant Origin.

The p-methoxycinnamic acid (p-MCA) is one of the most studied phenylpropanoids with high importance not only in the wide spectrum of therapeutic activities but also its potential application for the food industry. This natural compound derived from plants exhibits a wide range of biologically useful properties; therefore, during the last two decades it has been extensively tested for therapeutic and nutraceutical applications. This article presents the natural sources of p-MCA, its metabolism, pharmacokinetic properties, and safety of its application. The possibilities of using this dietary bioactive compound as a nutraceutical agent that may be used as functional food ingredient playing a vital role in the prevention and treatment of many chronic diseases is also discussed. We present the antidiabetic, anticancer, antimicrobial, hepato-, and neuroprotective activities of p-MCA and methods of its lipophilization that have been developed so far to increase its industrial application and bioavailability in the biological systems.

Microwave-Assisted Claisen-Schmidt Condensation Reaction of Ethyl p-methoxycinnamate to Synthesize p-Methoxystyryl Ketone Derivatives and Evaluate Anti-inflammatory Activity of Synthetic Products

The rhizome of Kaempferia galanga has been known to contain ethyl p-methoxycinnamate (EPMC) (1) as a main component, which has anti-inflammatory properties. Previously we have reported the structural modification of EPMC (1) to form another ester, nitrostyrene, and cinnammamide derivatives and then studied their structure-activity relationships as anti-inflammatory agent. In continuing our research, in this paper, we report the microwave-assisted Claisen-Schmidt condensation of EPMC (1) to synthesize a series of p-methoxystyryl ketones followed by a study of their anti-inflammatory activity. The reaction begins with microwave-assisted cleavage oxidation of hydrolyzed product of EPMC, p-methoxycinnamic acid (2) with Ca(NO3)2 for the synthesis of p-methoxybenzaldehyde (3). Furthermore, 3 was reacted with acetophenone, ethyl methyl ketone and acetone via microwave-assisted Claisen-Schmidt condensation for the synthesis of (E)-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one (5a) (E)-1-(4-methoxyphenyl)pent-1-en-3-one (5b) and (E)-4-(4-methoxyphenyl)but-3-en-2-one (5c), respectively. The reaction products were characterized using spectroscopic techniques and were then tested for anti-inflammatory activity using in vitro anti-denaturation of protein assay. It was found that converting EPMC (1) to 5a and 5b reduced anti-inflammatory activity, while 5c retained anti-denaturation activity with an IC50 of 72.8 µg/ml.

Microwave-Assisted Claisen-Schmidt Condensation Reaction of Ethyl p-methoxycinnamate to Synthesize p-Methoxystyryl Ketone Derivatives and Evaluate Anti-inflammatory Activity of Synthetic Products

The rhizome of Kaempferia galanga has been known to contain ethyl p-methoxycinnamate (EPMC) (1) as a main component, which has anti-inflammatory properties. Previously we have reported the structural modification of EPMC (1) to form another ester, nitrostyrene, and cinnammamide derivatives and then studied their structure-activity relationships as anti-inflammatory agent. In continuing our research, in this paper, we report the microwave-assisted Claisen-Schmidt condensation of EPMC (1) to synthesize a series of p-methoxystyryl ketones followed by a study of their anti-inflammatory activity. The reaction begins with microwave-assisted cleavage oxidation of hydrolyzed product of EPMC, p-methoxycinnamic acid (2) with Ca(NO3)2 for the synthesis of p-methoxybenzaldehyde (3). Furthermore, 3 was reacted with acetophenone, ethyl methyl ketone and acetone via microwave-assisted Claisen-Schmidt condensation for the synthesis of (E)-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one (5a) (E)-1-(4-methoxyphenyl)pent-1-en-3-one (5b) and (E)-4-(4-methoxyphenyl)but-3-en-2-one (5c), respectively. The reaction products were characterized using spectroscopic techniques and were then tested for anti-inflammatory activity using in vitro anti-denaturation of protein assay. It was found that converting EPMC (1) to 5a and 5b reduced anti-inflammatory activity, while 5c retained anti-denaturation activity with an IC50 of 72.8 µg/ml.