Cinnamic Acid Derivatives Research Articles

Phytochemical Constituents and Biological Activities of Jasonia glutinosa L.: The First Report for the Plant Growing in North Africa

Jasonia glutinosa (rock tea), also known as Chiliadenus glutinosa Cass., is a medicinal plant growing in the Mediterranean Basin. It is used for the treatment of depression, gastrointestinal complaints, inflammations, appendicitis, colds, and respiratory disorders. The current study is the first report for the plant species growing in Libya and aims to investigate the phytochemical constituents, antioxidant, cytotoxic, and antimicrobial activities of the plant’s aqueous ethanolic extract. The phytochemical investigation was conducted by the spectrophotometric quantitative assay and the LC-MS analysis. The analysis revealed the presence of 14.67 and 46.72 mg/g of the total phenolics and flavonoids equivalent to gallic acid and rutin, respectively. A total of thirty compounds of phenolic acids and flavonoids were identified by the LC-MS analysis, with a total relative percentage of 18.69%. The analysis revealed the dominance of methoxylated flavonoids and cinnamic acid derivatives, including caffeoylquinic acids. The in vitro antioxidant assays showed 265.55, 513.32, and 27.10 μM Trolox eq/mg of extract in the ABTS, ORAC, and FRAP assays, respectively. Cancer cell growth inhibitions of 9.23, 11.42, and 34.01% at a concentration of 100 μg/mL against MCF-7, HepG2, and PANC-1 cell lines were obtained, which is considered a weak cytotoxic effect when compared to the standard anticancer agent, doxorubicin (DOX). No antimicrobial activity was noticed for the plant extract against all tested microorganisms, i.e., Escherichia coli, Bacillus subtilis, Staphylococcus aureus, Salmonella typhimurium, Candida albicans, and Saccharomyces cerevisiae. The weak antimicrobial effect of the plant did not support the claim of traditional use of the plant as an antimicrobial agent.

An efficient human stem cells derived cardiotoxicity testing platform for testing oncotherapeutic analogues of quercetin and cinnamic acid.

Oncotherapeutics research is progressing at a rapid pace, however, not many drugs complete the successful clinical trial because of severe off-target toxicity to cardiomyocytes which ultimately leads to cardiac dysfunction. It is thus important to emphasize the need for early testing for possible cardiotoxicity of emerging oncotherapeutics. In this study, we assessed a novel stem cell-derived cardiac model for testing for cardiotoxicity of novel oncotherapeutics. We evaluated the cardiotoxic effect of synthesized derivatives of oncotherapeutics, quercetin (QMJ-2, -5, and -6) and cinnamic acid (NMJ-1, -2, and -3) using human Wharton's jelly mesenchymal stem cells-derived cardiomyocytes (WJCM) against known cardiotoxic oncologic drugs, doxorubicin, 5-fluorouracil, cisplatin. QMJ-6, NMJ-2, and NMJ-3 were not cardiotoxic and had minimum cardiac side effects. They did not show any effect on cardiomyocyte viability, caused low LDH release, and intracellular ROS production kept the calcium flux minimal and protected the active mitochondrial status in cardiomyocytes. They persevered cardiac-specific gene expression as well. However, compounds QMJ-2, QMJ-5, and NMJ-1 were cardiotoxic and the concentration needs to be reduced to prevent toxic effects on cardiomyocytes. Significantly, we were able to demonstrate that WJCM is an efficient cardiac testing model to analyze the cardiotoxicity of drugs in a human context.

Effects of saline extract and lectin from Punica granatum seed sarcotesta on Aedes aegypti larvae

• Salin extract contained lectin, ellagic acid, α and β punicalagins, ellagic acid derivatives, and cinnamic acid derivatives. • The extract was able to induce mortality in A. aegypti larvae. • The lectin PgTeL did not show larvicidal activity. • The extract altered midgut morphology and inhibited amylase and trypsin activity in the larval gut. Currently, one of the main strategies to reduce the incidence of the arboviruses such as Zika, dengue, and chikungunya is through the population control of their vector, Aedes aegypti . Lectins are carbohydrate-binding proteins with several biological properties, including insecticidal activity against A. aegypti. Punica granatum sarcotesta contains a chitin-binding lectin (PgTeL), which prompted our evaluation of its toxicity against A. aegypti . Here, we analyzed the effects of saline extract from P. granatum sarcotesta and PgTeL on the survival of A. aegypti larvae. Saline extract of P. granatum was evaluated for the presence of secondary metabolites; PgTeL was further isolated and purified from this extract. Larvicidal assay was performed using P. granatum saline extract (0.17–1.20 mg/mL of protein) and isolated PgTeL (0.1–1.0 mg/mL). Histological analysis was performed to evaluate the effects of the extract on the larvae midgut morphophysiology. Additionally, the activity of digestive enzymes in midgut extracts of the larvae was determined. P. granatum extract, containing protein (17.1 mg/mL), ellagic acid (2.1 mg/mL), α-punicalagin (2.2 mg/mL), β-punicalagin (2.3 mg/mL), ellagic acid derivatives (2.2 mg/mL), and cinnamic acid derivatives (3.9 mg/mL), caused larvae mortality (LC 50/48 h : 0.67 mg/mL of protein) and altered the midgut morphology; midgut cells were affected, showing protrusions in the apical region and a thickening of the peritrophic matrix. P. granatum extract inhibited amylase and trypsin activities in the larval gut. However, PgTeL did not display larvicidal activity. In conclusion, the sarcotesta saline extract from pomegranate shows larvicidal activity against A. aegypti, and the mode of action may involve disruption of the digestive processes of the larvae. These findings may represent a first step towards the availability of a new tool to control A. aegypti .

Phytochemical profiling and biological activity of the extracts obtained from green biomass of three Miscanthus L. species using supercritical carbon dioxide extraction

Taxa belonging to the genus Miscanthus L. (silvergrass) are non-invasive plants that can grow on marginal land that are not suitable for food production. These species give high yields of lignocellulosic biomass, being a rich and renewable source of organic matter for the production of second-generation biofuels (ethanol) and for other practical purposes, such as raw material for paper production. The most promising species of the genus Miscanthus L., in terms of practical use in industry and agriculture, are M. sinensis, M. sacchariflorum and their hydride - M. × giganteus. In this study, extracts obtained from the green biomass of these Miscanthus L. species underwent detailed phytochemical investigation and multidirectional biological evaluation. The extracts were prepared using supercritical fluid extraction with water as co-solvent. The qualitative RP-HPLC/PDA analysis of the extracts after their purification with solid-phase extraction confirmed their similar phytochemical profiles. Six free phenolic acids ( p -hydroxybenzoic, isovanillic, syringic, p -coumaric, ferulic and isoferulic) and one trans -cinnamic acid derivative were identified and determined. The antimicrobial, antiviral, anthelmintic and anticancer activity of the supercritical extracts of Miscanthus L. species studied was revealed for the first time. Moreover, the extracts possessed low cytotoxicity against normal cells. This screening evaluation showed that, besides giving high yields of lignocellulosic biomass, these grasses could also be a source of valuable bioactive compounds for the pharmaceutical and cosmetic industries. • Supercritical carbon dioxide extracts of silvergrasses had similar phenolic profiles. • All slivergrass extracts showed antibacterial and antifungal activities. • Amur and giant silvergrass extracts revealed anthelmintic (nematocidal) effects. • Chinese and giant silvergrass extracts inhibited herpes simplex virus type-1 cycle. • Amur silvergrass extract was selectively cytotoxic against melanoma cells.

Isolation, Structure Characterization, Total Synthesis and Biological Evaluation of Cinnamic Acid Derivatives from Tinospora sagittata.

Thirteen cinnamic acid derivatives (1-13), including six formerly unreported hybrids incorporating different short-chain fatty acid esters (1-6), have been obtained and structurally elucidated from an ethnological herb Tinospora sagittata. The structures of them have been established by spectroscopic data analyses and NMR comparison with known analogs, while those of 1, 2, 4 and 6 have been further supported by total synthesis, and it is the first report of this type of metabolites from the title species. All the isolates have been assessed in an array of bioassays encompassing cytotoxic, antibacterial, anti-inflammatory, antioxidant, as well as α-glucosidase and HDAC1 inhibitory models. Compound 7 showed significant inhibitory activity against α-glucosidase, and half of the isolates also displayed moderate antiradical effect.

Ugi Adducts: Design and Synthesis of Natural-based α-glucosidase Inhibitors

Background: α-Glucosidase inhibitors have been found as the main tool for the treatment of type 2 diabetes. In this respect, the synthesis of a new series of amino-oxoethylcinnamamide derivatives containing α,β-unsaturated carbonyl-based moiety, was developed to be evaluated for their anti-α- glucosidase activity. Methods: The title compounds were synthesized via the Ugi reaction of cinnamic acid, isocyanides, aromatic aldehydes, and amine derivatives at ambient temperature. All newly synthesized derivatives were screened for their in vitro α-glucosidase inhibitory activity. Results: Among synthesized compounds, derivative 5b displayed promising anti-α-glucosidase activity (IC50 = 115.6 μM), approximately 6-fold more potent than the standard drug (acarbose, IC50 = 750.0 μM). Moreover, kinetic characterization of enzyme inhibition was performed to understand the mechanism of inhibition. To determine the mode of binding interactions of prepared compounds with the enzyme, molecular docking studies were also conducted. Conclusions: Ugi products merit to be investigated in anti-diabetic drug discovery developments. This paper is dedicated to our unique teacher of Chemistry and Medicinal Chemistry, Professor Abbas Shafiee (1937-2016).

A Screening System for the Identification of Fragment Molecules toward the Creation of Nuclear Receptor Ligands

Peroxisome proliferator-activated receptor γ (PPARγ) is a member of the nuclear receptor superfamily, which plays an important role in glucose and lipid metabolism as well as inflammation. The transcriptional activity of PPARγ is regulated by the binding of its ligand and the accompanied conformational change followed by the recruitment of cofactors. The ligand-binding pocket (LBP) of PPARγ comprises multiple sub-pockets and includes a large, Y-shaped cavity. In some cases, more than two ligands simultaneously occupy the LBP and cooperatively activate PPARγ transcription. Inspired by this peculiar character, the author proposed a strategy to create new PPARγ ligands in two steps: first, identifying a combination of ligands that cooperatively activate PPARγ, and second, designing and synthesizing their hybrid structure. Cooperative activation can be detected by a conventional cell-based assay using a reporter gene, which may provide advantages over the existing fragment-based drug discovery approach. Using this strategy, a plant-derived cinnamic acid derivative was found to synergistically activate PPARγ in combination with GW9662, an irreversible antagonist. The designed hybrid structure was synthesized and found to behave as a covalent agonist, which partially activates PPARγ transcription. Structure-activity studies revealed the importance of proximity and orientation in the linkage of the two units. The strategy discussed in this article may contribute to the development of a highly potent PPARγ agonist.

Ethnomedicinal, phytochemical and pharmacological investigations of Baccharis dracunculifolia DC. (ASTERACEAE).

Baccharis dracunculifolia DC (Lamiaceae) (Asteraceae) is found in South America, mainly in Argentina, Brazil, Bolivia, Paraguay and Uruguay. Folk medicine is used as a sedative, hypotensive, bronchodilator, cardiovascular disorders, anti-flu, and also in skin wounds. Considered the main source of green propolis, which increases the pharmacological interest in this species. It is also known as a "benefactor" plant facilitating the development of other plant species around it, being indicated for the recovery of degraded areas. This species has been studied for decades in order to isolate and identify the active principles present in the aerial parts (leaves and flowers) and roots. The present study consists of a review of the scientific literature addressing the ethnobotanical, ethnomedicinal, phytochemical, pharmacological and potential cytotoxic effects of the B. dracunculifolia species. In this survey, we sought to investigate issues related to the botanical and geographic description of the species, the ethnobotanical uses, as well as the phytochemical studies of the essential oil, extracts and green propolis obtained from the aerial parts and roots of B. dracunculifolia. Using high precision analytical tools, numerous compounds have already been isolated and identified from leaves and flowers such as the flavonoids: naringenin, acacetin, dihydrokaempferol, isosakuranetin and kaempferide; phenolic acids: p-coumaric, dihydrocoumaric, ferulic (E)-cinnamic, hydroxycinnamic, gallic, caffeic, and several caffeoylquinic acids derivatives; phenolic acids prenylated: artepillin C, baccharin, drupanin; the glycosides dracuculifosides and the pentacyclic triterpenoids: Baccharis oxide and friedelanol. The predominant class in the essential oil of leaves and flowers are terpenoids comprising oxygenated monoterpenes and sesquiterpenes, highlighting the compounds nerolidol, spathulenol, germacrene D and bicyclogermacrene. These compounds give the species high antimicrobial, antioxidant, antitumor, analgesic, immunomodulatory and antiparasitic potential, making this species a promising herbal medicine. In vitro toxicity assays with B. dracunculifolia extract showed low or no cytotoxicity. However, in vivo analyses with high doses of the aqueous extract resulted in genotoxic effects, which leads us to conclude that the toxicity of this plant is dose-dependent.

Arecaceae fruits: Fatty acids, phenolic compounds and in vitro antitumor activity

Arecaceae fruits are regarded as raw sources of valuable phytochemicals. In this work, several Arecaceae fruits belonging to eleven taxa were screened for fatty acids (FA) by gas chromatography with flame ionization detector and checked for their in vitro antitumor activity against the HT-29 colorectal cancer cells line through the MTT test. The parallel use of two chromatography systems, HPLC-DAD and LC-MS, allowed the precise characterization of all phenolic compounds contained in the fruits. Howea belmoreana had the highest FA amounts (11.7 g/100 g on dry weight); Syagrus romanzoffiana had a relatively high PUFA content (26.3% of total FA); and Butia capitata contains high amounts of medium-chain saturated FA (51.2%). Total phenolics reached 201.8 mg/100 g on dry weight in Phoenix dactylifera var. Medjool. Among phenolics, occurred benzoic acids, phenylpropanoic acid, and cinnamic acid derivatives. It highlights the great diversity of flavonoids detected as (−)-catechin, quercetin, and kaempferol, as well as phenolic glycosides, such as isorhamnetin-3-O-glucoside. The methanol:water (60:40, v/v) extracts of fruits induced dose- and time-dependent inhibitory effects on HT-29 cancer cells. Overall, the fruits of Arecaceae taxa evaluated here constitute suitable candidates to be used as functional foods.

Cardamom Extract Alleviates the Oxidative Stress, Inflammation and Apoptosis Induced during Acetaminophen-Induced Hepatic Toxicity via Modulating Nrf2/HO-1/NQO-1 Pathway.

Aqueous CARD extract was subjected to LC-TOF-MS analysis to separate and elucidate some of its components. In vivo animal experiments involved five groups of animals. In the normal and cardamom groups, mice were administered either saline or CARD (200 mg/kg), respectively, orally daily for 16 days. In the APAP group, the animals were administered saline orally daily for 15 days, and on the 16th day, animals were administered APAP (300 mg/kg) IP for the induction of acute hepatic failure. In the CARD 200 + APAP group, mice were administered CARD (200 mg/kg) for 15 days, followed by APAP on the 16th day. The aqueous extract of CARD showed several compounds, belonging to polyphenol, flavonoids, cinnamic acid derivatives and essential oil components. In the in vivo investigations, APAP-induced impaired liver function, several histopathological alterations, oxidative stress and inflammatory and apoptotic status signified severe hepatic failure. Whereas, pretreatment with the CARD extract prior to APAP administration diminished serum levels of the hepatic function test and augmented Nrf2 nucleoprotein and HO-1 and NQO-1. CARD down-regulated MDA, inflammatory mediators (IL-1β, IL-6, TNF-α and NF-κB) and apoptotic markers (caspase 3 and 9 and Bax) and amplified the activities of SOD, catalase, GSH-Px and GSH-R in hepatic tissue samples. CARD extract mitigated the hepatic toxicity induced by APAP. The underlying mechanism of action of such hepato-protective action may be through upregulation of the Nrf2/HO-1/NQO-1 pathway with subsequent alleviation of the oxidative stress, inflammation and apoptosis induced by APAP. Many of the compounds identified in the CARD extract could be attributed to this pharmacological action of the extract.

Ultraviolet (UV) light-induced geometrical isomerization of cinnamic acid containing molecules: A plausible, non-enzymatic approach to modify metabolite composition of plant extracts

• UV light can be used to enhance the cinnamic acid containing-metabolite composition of a plant. • LC-MS in combination with multivariate statistics can be used to probe for the presence of photo-induced metabolites in plant extracts. • UV-irradiated plant extracts have a coherent metabolite composition as compared to naturally growing plants. Cinnamic acid containing molecules are widely distributed in plants, and they are known to possess several pharmacological properties. Structurally, these molecules consist of C 6 C 3 skeletal backbone, with an olefin functional group on the C 3 part . Naturally, plants produce a broad spectrum of cinnamic acid derivatives with a trans configuration, however, cis isomers are formed due to excessive UV-light exposure, thereby increasing the already complex metabolomes of plants containing these compounds. In high sunlight intensive areas, the prevalence of the cis isomers of cinnamic acid containing molecules is becoming more prevalent and synonymous with extracts of many plants. It is therefore imperative to develop analytical and data handling strategies to account for the presence of these molecules, which can serve as a template for rational design of pharmacologically active plant extracts or smart photo-switchable drugs. Herein, we show that a combination of ultra-high performance liquid chromatography quadrupole time of flight mass spectrometry (UHPLC-QTOF-MS) and principal component analysis (PCA) allows differentiation of plants extracts of which metabolome modification through UV-radiation has been carried out. The results of the current study show that geometrical isomerism is a feasible, non-enzymatic approach to modify metabolite composition of plants. This simple method can be used to create “super” extracts of plants containing structurally diverse metabolites to be evaluated for various pharmacological properties in the future.

Virulence and biofilm inhibition of 3-methoxycinnamic acid against Agrobacterium tumefaciens.

In the current study the anti-virulence and anti-biofilm activities of the cinnamic acid derivative, 3-methoxycinnamic acid, was investigated against Agrobacterium tumefaciens. Based on the disc diffusion test and β-galactosidase activity assay, 3-methoxycinnamic acid was shown to interfere with the quorum sensing (QS) system of A. tumefaciens. Crystal violet staining assay, phenol-sulfuric acid method, Bradford protein assay and confocal laser scanning microscopy (CLSM) revealed that the biofilm formation of A. tumefaciens was inhibited after the treatment of 3-methoxycinnamic acid. Employing high-performance liquid chromatography (HPLC) analysis of culture supernatant revealed that the production of 3-oxo-octanoylhomoserine lactone (3-oxo-C8-HSL) decreased concentration-dependently after treatment with 3-methoxycinnamic acid. Swimming and chemotaxis assays also indicated that 3-methoxycinnamic acid had a good effect on reducing the motility and chemotaxis of A. tumefaciens. In addition, the RT-qPCR, molecular docking and simulations further demonstrated that 3-methoxycinnamic acid could competitively inhibit the binding of 3-oxo-C8-HSL to TraR and down-regulate virulence-related genes. 3-Methoxycinnamic acid is proved to have good anti-virulence and anti-biofilm activities against A. tumefaciens. This is the first study that investigates the anti-virulence and anti-biofilm activities of 3-methoxycinnamic acid against A. tumefaciens. With its potential QS-related virulence and biofilm inhibitory activities, 3-methoxycinnamic acid is expected to be developed as a potent pesticide or adjuvant for the prevention and treatment of crown gall caused by A. tumefaciens.

Untargeted Metabolomics by Using UHPLC–ESI–MS/MS of an Extract Obtained with Ethyl Lactate Green Solvent from Salvia rosmarinus

Salvia rosmarinus (Lamiaceae), previously known as Rosmarinus officinalis, is a plant cultivated worldwide, native to the Mediterranean region. Its leaves are traditionally used for cooking. This species possesses numerous biological activities, including antioxidant, antimicrobial, anticancer, anti-inflammatory, and hepatoprotective properties. These biological properties are due to the presence of phenolic compounds, including rosmarinic acid and phenolic diterpenoids, such as carnosic acid and carnosol. In this study, we investigated the chemical composition of a green extract obtained by maceration with ethyl lactate for the first time. Seventy-five compounds were tentatively identified by UHPLC–ESI–MS/MS, including six organic acids, six cinnamic acid derivatives, five fatty acids, eighteen flavonoids, and thirty-eight terpenoids. Thus, abietane-type diterpenoids from the ethyl lactate extract were the predominant diterpenoids in the Chilean S. rosmarinus species, in contrast to the Chinese species, in which labdane and isopimarane-type diterpenoids were found for the first time. Finally, our study confirms that the extraction of S. rosmarinus with green ethyl lactate as a solvent is efficient and sustainable for the identification of flavonoids, phenols, and terpenoids from leaves.

Discovery of Simple Diacylhydrazine-Functionalized Cinnamic Acid Derivatives as Potential Microtubule Stabilizers.

To develop novel microtubule-binding agents for cancer therapy, an array of N-cinnamoyl-N’-(substituted)acryloyl hydrazide derivatives were facilely synthesized through a two-step process. Initially, the antiproliferative activity of these title compounds was explored against A549, 98 PC-3 and HepG2 cancer cell lines. Notably, compound I23 exhibited the best antiproliferative activity against three cancer lines with IC50 values ranging from 3.36 to 5.99 μM and concurrently afforded a lower cytotoxicity towards the NRK-52E cells. Anticancer mechanism investigations suggested that the highly bioactive compound I23 could potentially promote the protofilament assembly of tubulin, thus eventually leading to the stagnation of the G2/M phase cell cycle of HepG2 cells. Moreover, compound I23 also disrupted cancer cell migration and significantly induced HepG2 cells apoptosis in a dosage-dependent manner. Additionally, the in silico analysis indicated that compound I23 exhibited an acceptable pharmacokinetic profile. Overall, these easily prepared N-cinnamoyl-N’-(substituted)acryloyl hydrazide derivatives could serve as potential microtubule-interacting agents, probably as novel microtubule-stabilizers.

A new cinnamic ester derivative from Glochidion velutinum leaves and evaluation of its antioxidant and antibacterial activity

The plant Glochidion Velutinum (GV) family Euphorbiaceae , a medicinal plant, is reported to possess various therapeutic applications such as antidiabetic, anticancer, antioxidant, antimicrobial, anti-inflammatory etc. However, the compounds responsible for therapeutic value have not yet been isolated. The present study reports the isolation of a compound from the leaves of GV. The compound is identified as a cinnamic acid derivative ( p -pentadecayl ethyl cinnamate) through extensive spectral studies. Its antioxidant nature such as DPPH free radical scavenging assay, total antioxidant capacity, and antibacterial activity have been evaluated. The compound exhibited lower antioxidant properties compared to the standard. It has shown moderate antimicrobial activity against ten bacteria and significant antibacterial activity against Proteus Vulgaris compared to standard ciprofloxacin .

Lophine-cinnamoyl hybrids: Synthesis, photophysical properties and a spectroscopic and molecular dynamics approach towards interactions with bovine serum albumin

Lophine and cinnamic acid derivatives have gained considerable attention due their chemical, biological and fluorescence emission properties. Herein we reported the synthesis of a new family of lophine-cinnamoyl hybrids connected by a methylene chain with two to nine carbon atoms. The hybrids show absorption in the ultraviolet and emission in the blue-violet region independent of the length of the alkyl chain spacer. Non-covalent interactions of the hybrids to bovine serum albumin (BSA) were investigated by UV–Vis absorption and fluorescence spectroscopy. Overall, the hybrids display moderate affinities for BSA (binding constants in the range 10–14 × 104 M−1) and can be effectively employed as protein probes using BSA as a model. The theoretical calculations showed preferential interactions of the hybrids with the binding pocket located near to Trp213 and the number of binding sites equal to 1 are in agreement with the experimental data obtained through the Stern-Volmer approach.

Antifungal effects and active compounds of the leaf of Allium mongolicum Regel.

Taking plant metabolites as material to develop new biological fungicides is still an important mission for pesticide development, and the preliminary study confirmed that Allium mongolicum showed a certain inhibitory effect on plant pathogens. In this study, the antifungal activity of extracts of A. mongolicum was studied and the compounds were isolated, purified, and identified by HPLC, NMR, and ESI-MS. The methanol extract of A. mongolicum exhibited certain inhibitory activity against almost all nine tested pathogens at concentration of 0.5 mg/ml. Sixteen compounds were isolated and purified from the extract, which were identified as nine flavonoids, six phenolic acids, and an amino acid. Among them, cinnamic acid derivatives 1, 2, and 3 and flavonoids 7, 8, 9, and 13 were separated in A. mongolicum for the first time.

Free Phenolic Compounds, Antioxidant Capacity and FT-NIR Survey of Debittered Lupinus mutabilis Seeds

Lupinus mutabilis protein-rich seeds must be debittered before consumption. The aim of this research was to assess free phenolic compounds, antioxidant capacity and FT-NIR spectra of flours from debittered seeds of 33 Andean ecotypes of L. mutabilis, and five varieties belonging to L. luteus, L. angustifolius and L. albus, as controls. The free phenolics were quantified by RP-HPLC, while the antioxidant capacity was evaluated spectrophotometrically through the Reducing Power, ABTS, FRAP and DPPH methods. The free phenolics of L. mutabilis were mostly (85.5–99.6%) flavonoids (genistein and genistein derivatives, apigenin, catechin and naringenin). Other compounds, detected in low quantities, were phenylethanoids (tyrosol and tyrosol derivative) and phenolic acids (cinnamic acid derivatives). The highest total free phenolic concentration was observed in H6 INIA BP (1393.32 mg/kg DM), followed by Chacas, Moteado beige, Huánuco and Lircay. The antioxidant capacity of the L. mutabilis ecotypes exceeded that of the controls and was correlated to flavonoids content. Additionally, a relationship between free phenolic compounds and spectral bands was established by FT-NIR, paving the way for a fast, reliable and non-destructive approach to lupin seeds characterisation. Even after debittering, lupin flours maintained high free phenolic concentrations and antioxidant capacity.

Synthesis of New Cinnamoyl-Amino Acid Conjugates and in Vitro Cytotoxicity and Genotoxicity Studies.

Amino acid conjugates are described by the reaction of amino acids with bioactive organic groups such as vitamins, hormones, flavonoids, steroids, and sugars. In this study, 12 new conjugates were synthesized by reaction of cinnamic acid derivatives with various amino acids. Cytotoxic studies against four different human cancer cells (MCF7, PC-3, Caco-2, and A2780) were carried out by MTT assay method at five different concentrations. The structure-activity relationships based on the cell viability rates were evaluated. To compare the anticancer activities of the compounds using computational chemistry methods, they were docked against A2780 human ovarian cancer, Michigan Cancer Foundation-7 (MCF7), human prostate cancer (PC-3) and human colon epidermal adenocarcinoma (Caco-2) cell lines and compared with the standard 5-Fluorouracil. The results indicate that the efficacy of cinnamic acid derivatives increases with the presence of amino acids. Comet assay was conducted to understand whether the cell deaths occur through DNA damage mechanism and the results exhibit that the changes in the specified parameters were statistically significant (p<0.05). Our study demonstrated that the compounds cause cell death through the formation of DNA damage mechanism.

Hydroxypropyl chitosan modified by cinnamic acid derivative nanoparticles for stabilising Pickering emulsion

SummaryChitosan (CS) derivatives, chemically modified appropriately, can be used to produce nanoparticles with good properties. In this work, using CS, hydroxypropyl CS (HPCS) and HPCS modified by cinnamic acid (HPCS‐CA) derivative as raw materials, the nanoparticles were synthesised by ion crosslinking method with tripolyphosphate. FT‐IR spectra indicated that CS and its derivatives successfully cross‐linked with TPP at the molecular level. XRD and TG results exhibited changes in crystallinity and thermal stability. The nanoparticles had narrow size distribution and were nearly spherical. The surfaces of the nanoparticles were all positively charged. The nanoparticles‐stabilised oil‐in‐water Pickering emulsions were obtained by high‐speed homogenisation. The emulsions' morphology was reported by confocal laser scanning microscopy, indicating that the Pickering emulsions were synthesised successfully. The stability of the emulsion stabilised by HPCS‐CA nanoparticles was better than that of CS and HPCS nanoparticles. Taking curcumin as the target component, its stability in Pickering emulsions was good. The Pickering emulsion stabilised by HPCS‐CA nanoparticles may be a novel bioactive compound delivery system.