Cinnamic Acid Derivatives Research Articles

Protective effect of (E)-(2,4-dihydroxy)-α-aminocinnamic acid, a hydroxy cinnamic acid derivative, in an ulcerative colitis model induced by TNBS.

Ulcerative colitis (UC) is a multifactorial disease that causes long-lasting inflammation and ulcers in the digestive tract. UC is the most common form of inflammatory bowel disease (IBD). The current treatment for mild-to-moderate UC involves the use of 5-aminosalicylates (5-ASA), but much of this compound is unabsorbed and metabolized by N-acetylation. Several efforts have since been made to evaluate new molecules from synthetic or natural sources. Recently, it was reported that (E)-(5-chloro-2-hydroxy)-α-aminocinnamic acid (2c) and (E)-(2,4-dihydroxy)-α-aminocinnamic acid (2f) are as good or better myeloperoxidase (MPO) inhibitors and antioxidants than 5-ASA. Then, the present study aimed to evaluate the protective effects of 2c and 2f on a rat model of UC induced by 2,4,6-trinitrobenzene sulfonic acid (TNBS). The results showed that TNBS caused the induction of colonic ulcers, as well as a significant increase in MPO activity and malondialdehyde (MDA) and a decrease in glutathione (GSH) content. The administration of 2f, 2c and 5-ASA, decreased the ulcers presence, inhibited MPO peroxidation activity and MPO presence (as determined by immunofluorescence), and increased GSH and reduced MDA content. However, 2f was better than 2c and 5-ASA, then, the principal mechanism by which 2f presented a protective effect in a UC model induced by TNBS in rats is by inhibiting MPO activity and due to its antioxidant activity.

Ferulic Acid Interferes with Radioactive Intestinal Injury Through the DJ-1-Nrf2 and Sirt1-NF-κB-NLRP3 Pathways

Radiation-induced intestinal injury is a common complication of radiotherapy for abdominal and pelvic malignancies. Due to its rapid proliferation, the small intestine is particularly sensitive to radiation, making it a critical factor limiting treatment. Ferulic acid (FA), a derivative of cinnamic acid, exhibits antioxidant, anti-inflammatory, and anti-radiation properties. In this study, we established a mouse model of radiation-induced intestinal injury using a dose of 11 Gy at a rate of 96.62 cGy/min. Our findings indicate that FA’s protective effects against radiation-induced intestinal injury may be mediated through the parkinsonism-associated deglycase (DJ-1) nuclear factor erythroid 2-related factor 2 (Nrf2) and silent mating type information regulation 2 homolog 1 (Sirt1) nuclear Factor kappa-light-chain-enhancer of activated B cells (NF-κB) NOD-like receptor family, pyrin domain containing 3 (NLRP3). FA was found to mitigate changes in oxidative stress indices and inflammatory factors induced by radiation, as well as to attenuate radiation-induced pathological alterations in the small intestine. Furthermore, FA enhanced the expression of DJ-1 and Nrf2 at both the transcriptional and protein levels, inhibited NLRP3 protein fluorescence intensity, and reduced the expression of NLRP3, interleukin-18 (IL-18), and interleukin-1 beta (IL-1β). Additionally, FA suppressed the transcription and translation of NF-κB, NLRP3, cysteine-aspartic acid protease-1 (Caspase-1), IL-18, and IL-1β by upregulating Sirt1, thereby alleviating radiation-induced inflammatory injury in the small intestine. Thus, FA holds promise as an effective therapeutic agent for ameliorating radiation-induced intestinal injury.

The effect of cinnamic acid derivative on the activity of mitochondrial enzymes in brain tissue under conditions of experimental Parkinson's disease

The aim: to evaluate the effect of cinnamic acid derivative on changes in mitochondrial enzymes activity in rats brain tissue under conditions of experimental Parkinson's disease. Materials and methods. Parkinson's disease was modeled in male Wistar rats by direct injection of rotenone solution (5 mg/ml) into the striatum. The analyzed compound 4-hydroxy-3,5-di-tretbutyl cinnamic acid and the reference ethylmethylhydroxypyridine succinate were administered orally in equivalent doses (100 mg/kg) for 30 days from the moment of pathology modeling. Next, a brain supernatant was obtained by differential centrifugation, in which changes in the activity of enzymes: citrate synthase, succinate dehydrogenase, cytochrome c oxidase and aconitase were evaluated. The obtained results were processed statistically. During the analysis, the StatPlus 7.0 application software package was used. Results. During the study, it was found that the administration of 4-hydroxy-3,5-di-tretbutyl cinnamic acid to rats increased the activity of citrate synthase, succinate dehydrogenase, cytochrome c oxidase and aconitase relative to untreated animals by 109.7% (p0.05); 53.6% (p0.05); 65.0% (p0.05) and 63.1% (p0.05), respectively, whereas against the background of the use of the reference, the activity of these enzymes increased by 56.3% (p0.05); 57.7% (p0.05); 71.7% (p0.05) and 49.1% (p0.05), respectively. At the same time, the activity of citrate synthase in animals treated by 4-hydroxy-3,5-di-tretbutyl cinnamic acid was higher than that in rats treated by the reference by 34.2% (p0.05). Conclusions. The study showed that the course administration of 4-hydroxy-3,5-di-tretbutyl cinnamic acid to animals with experimental Parkinson's disease is accompanied by an increase in the activity of mitochondrial enzymes, which may reflect the significant effect of this compound on the processes of mitochondrial biogenesis, mitophagy and generation of mitochondrial reactive oxygen species.

Sinapinic acid as a potential therapeutic agent for epilepsy through targeting NMDA receptors and nitrite level

Epilepsy, a widespread neural ailment considered by prolonged neuronal depolarization and repetitive discharge, has been linked to extreme stimulus of N-methyl-D-aspartate receptors (NMDARs). Despite the availability of approved anti-seizure medications (ASMs) in many developed nations, approximately 30% of epilepsy patients continue to experience drug-resistant seizures. Thus, a growing interest in discovering natural compounds as potential sources for new medications is growing. Sinapinic acid, a natural derivative of cinnamic acid found in food sources, is known for its neuroprotective properties. This study investigated how sinapinic acid interacts with NMDA receptors and its potential role in providing anticonvulsant effects. Male mice were randomly allocated into nine groups: a control group receiving normal saline (1 ml/kg), groups treated with sinapinic acid at doses of 1, 3, and 10 mg/kg, a group treated with diazepam at 10 mg/kg, a group treated with an NMDA agonist at 75 mg/kg, a group treated with an NMDA antagonist at 0.5 mg/kg, a group receiving the ineffective dose of sinapinic acid (1 mg/kg) along with the NMDA antagonist, and a group receiving the effective dose of sinapinic acid (10 mg/kg) along with the NMDA agonist. Sinapinic acid and other treatments were administered intraperitoneally 30 min prior to inducing seizures with PTZ injection. Seizure onset time was recorded following PTZ injection. Blood and brain samples were collected after anesthesia to determine serum and brain nitrite levels. Real-time PCR assessed NMDAR gene expression in the prefrontal cortex (PFC). Data were analyzed using Prism software. The time seizures began was notably extended in groups treated with sinapinic acid at doses of 3 and 10 mg/kg compared to those treated with saline (P < 0.05). Additionally, in the receiving group of an ineffective dose of sinapinic acid alongside ketamine, the beginning of seizure time was significantly prolonged compared to the group that received the ineffective dose of sinapinic acid alone (P < 0.05). Serum and prefrontal cortex (PFC) nitrite levels were significantly lower in mice treated with sinapinic acid at doses of 1, 3, and 10 mg/kg compared to the saline-treated group (P < 0.05). The gene expression of the NMDAR NR2B subunit in the PFC was decreased in groups treated with sinapinic acid at 1 and 10 mg/kg compared to the saline-treated group. Furthermore, co-administration of sinapinic acid (10 mg/kg) with NMDA resulted in significantly lower NR2A gene expression than the group treated with 10 mg/kg of sinapinic acid alone. Conversely, co-administration of ketamine with sinapinic acid (1 mg/kg) significantly increased NR2B subunit gene expression compared to the group treated with sinapinic acid at 1 mg/kg alone. Sinapinic acid showed anticonvulsant effects through reduced serum and PFC nitrite and modulation of glutamatergic signaling.

Design, In Silico, and In vitro Evaluation of Polymer-Based Drug Conjugates Incorporated with Derivative of Cinnamic Acid, Zidovudine, and 4-Aminosalicylic Acid against Pseudo-HIV-1.

The incorporation of anti-HIV drugs into polymer to form polymer-drug conjugates has been reported to result in improved therapeutic activity. Zidovudine, an anti-HIV drug, was explored alone and in combination with known drug molecules using polyamidoaminebased carriers. Polymer-drug conjugates incorporated with zidovudine, cinnamic acid, and 4-aminosalicylic acid were prepared and evaluated for their potential efficacy in vitro against pseudo- HIV-1. Aqueous Michael addition polymerization reaction was employed to prepare the conjugates. The conjugates were incorporated with zidovudine, cinnamic acid, and 4-aminosalicylic acid. They were characterized by SEM/EDX, XRD, FTIR, NMR, LC-MS, particle size analysis, in vitro analysis, computational studies, and in silico toxicity predictions. The conjugates displayed spherically shaped morphology. The in vitro findings showed that polymer-drug conjugates, T15 and T16, with a single drug were effective against pseudo- HIV-1 at high concentrations of 111.11 and 333.33 μg/mL, respectively. The molecular docking studies confirmed the in vitro results. The Swiss ADME, ProTox-II, and GUSAR (General Unrestricted Structure-Activity Relationships) revealed that these compounds are promising antiviral compounds. The prepared polymer-drug conjugates with a single drug showed promising effects against the Pseudo-HIV-1, and the conjugates displayed features that make them potential anti- HIV therapeutics that require further studies.

Preconcentration of Cinnamic Acid Derivatives in Traditional Chinese Medicines by an Effective Dispersive Liquid-Liquid Microextraction Based on a Hydrophobic Deep Eutectic Solvent.

A dispersive liquid-liquid microextraction based on hydrophobic deep eutectic solvent (hDES) was developed for the extraction and quantification of four cinnamic acid derivatives in traditional Chinese medicines coupled with high-performance liquid chromatography-ultraviolet detection. In this method, a hDES (tetrabutylammonium chloride-hexanoic acid, molar ratio of 1:2) was prepared as the extractant. It only took 15 s to handle multiple samples simultaneously by hand-assisted dispersion. The use of a narrow-bore tube reduced the amount of the hydrophobic extractant with easier recovery. The approach was influenced by several key parameters, including the composition and consumption of the DES, sample phase pH, salt amount, extraction time, and centrifugation time, all of which had been investigated and optimized. Moreover, the formation of the DES was characterized by Fourier-transform infrared spectroscopy and differential scanning calorimetry. Under the optimal conditions, enrichment factors of the target analytes ranged from 135 to 220. Satisfactory linearities (r ≥ 0.9977), detection limits (0.2-0.4ng/mL), precision (<8.5%), and accuracy (recoveries: 90.0%-104.6%) were obtained. The method has been successfully applied to the simultaneous extraction and preconcentration of four cinnamic acid derivatives in Chinese medicinal samples with rapidness, high efficiency, and convenience.

The fine structural changes of phenolic hydroxyl groups of cinnamic acid and its derivatives affects their inhibition mechanism and interaction with α-glucosidase

Cinnamic acid (CCA), p-coumaric acid (PCA), and caffeic acid (CA) are natural phenolic compounds and extensively utilized in the food industry. PCA and CA are both derivatives of CCA and share comparable molecular structures. In this study, the inhibitory mechanisms of CCA, PCA, and CA on α-glucosidase was investigated by employing inhibition kinetics and molecular docking analyses. Our results revealed that CCA (IC50 = 6.12 ± 0.056 mM) and CA (IC50 = 2.02 ± 0.083 mM) exhibited mixed-type inhibition, while PCA (IC50 = 3.82 ± 0.095 mM) exhibited non-competitive inhibition. The intermolecular energy values of CCA, PCA, and CA with α-glucosidase were determined to be −7.11, −7.94, and −8.14 kcal/mol, respectively, indicating their binding to α-glucosidase via hydrophobic interactions and hydrogen bonding, among which CA has the greatest binding ability. Fluorescence quenching results and circular dichroism (CD) spectra further confirmed the higher affinity of CA to α-glucosidase than that of CCA and PCA. These outcomes shed light on the importance of molecular structure differences in α-glucosidase inhibition and highlight the potential scope for developing low-glycemic-index functional foods.

A comparative UPLC-orbitrap-MS-based metabolite profiling of three Pelargonium species cultivated in Egypt

Several Pelargonium species are cultivated mainly to produce essential oils used in perfume industry and for ornamental purposes. Although the chemical composition and biological activities of their essential oils were extensively investigated, there is limited information about the chemical composition of their non-volatile constituents. In this study, we report an Ultra-Performance Liquid Chromatography-Mass Spectrometry (UPLC-MS)-based metabolomics approach for the annotation and analysis of various metabolites in three species; P. graveolens, P. denticulatum, and P. fragrans utilizing The Global Natural Product Social Molecular Networking (GNPS) and multivariate data analyses for clustering of the metabolites. A total of 154 metabolites belonging to different classes were annotated. The three species are good sources of coumarins, benzoic acid derivatives, organic acids, fatty acids, and phospholipids. However, the highest level of flavonols (mono- and di-O-glycosides) and cinnamic acid derivatives was found in P. graveolens and P. denticulatum, whereas tannins and flavone C-glycosides were abundant in P. fragrans. The metabolic profiles clarified here provide comprehensive information on the non-volatile constituents of the three Pelargonium species and can be employed for their authentication and possible therapeutic applications.

Defense Molecules of the Invasive Plant Species Ageratum conyzoides

Ageratum conyzoides L. is native to Tropical America, and it has naturalized in many other tropical, subtropical, and temperate countries in South America, Central and Southern Africa, South and East Asia, Eastern Austria, and Europe. The population of the species has increased dramatically as an invasive alien species, and it causes significant problems in agriculture and natural ecosystems. The life history traits of Ageratum conyzoides, such as its short life cycle, early reproductive maturity, prolific seed production, and high adaptive ability to various environmental conditions, may contribute to its naturalization and increasing population. Possible evidence of the molecules involved in the defense of Ageratum conyzoides against its natural enemies, such as herbivore insects and fungal pathogens, and the allelochemicals involved in its competitive ability against neighboring plant species has been accumulated in the literature. The volatiles, essential oils, extracts, residues, and/or rhizosphere soil of Ageratum conyzoides show insecticidal, fungicidal, nematocidal, and allelopathic activity. The pyrrolizidine alkaloids lycopsamine and echinatine, found in the species, are highly toxic and show insecticidal activity. Benzopyran derivatives precocenes I and II show inhibitory activity against insect juvenile hormone biosynthesis and trichothecene mycotoxin biosynthesis. A mixture of volatiles emitted from Ageratum conyzoides, such as β-caryophyllene, β-bisabolene, and β-farnesene, may work as herbivore-induced plant volatiles, which are involved in the indirect defense function against herbivore insects. Flavonoids, such as nobiletin, eupalestin, 5′-methoxynobiletin, 5,6,7,3′,4′,5′-hexamethoxyflavone, and 5,6,8,3,4′,5′-hexamethoxyflavone, show inhibitory activity against the spore germination of pathogenic fungi. The benzoic acid and cinnamic acid derivatives found in the species, such as protocatechuic acid, gallic acid, p-coumaric acid, p-hydroxybenzoic acid, and ferulic acid, may act as allelopathic agents, causing the germination and growth inhibition of competitive plant species. These molecules produced by Ageratum conyzoides may act as defense molecules against its natural enemies and as allelochemicals against neighboring plant species, and they may contribute to the naturalization of the increasing population of Ageratum conyzoides in new habitats as an invasive plant species. This article presents the first review focusing on the defense function and allelopathy of Ageratum conyzoides.

Nutrients and Antioxidants from Petit Verdot Grape Pomace Powder

T he study aimed to characterize pomace powder from the Petit Verdot grape of Mexican winemaking. The powder pomace (dry basis from pomace) was analyzed and contained 6.65% moisture, 9.17% fat, 9.54% protein, 51.41% dietary fiber, 6.10% soluble fiber, 45.3% insoluble fiber, and 4.62% ash. Also, the powder pomace contained various minerals, including calcium, copper, phosphorus, iron, magnesium, manganese, sodium, and potassium. The phenolic compounds found were hydrated quercetin, a cinnamic acid derivative, and a p-coumaric acid derivative. The limited diversity of phenolics in grape pomace powder is counterbalanced by its elevated dietary fiber and nutritional content, positioning it as a viable ingredient for food processing. The freeze-dried grape pomace powder contained a load of 4 log CFU/g, and the MacConkey culture medium detected no possible pathogenic microorganisms. These findings suggest that grape pomace powder could be a promising addition to the food industry, offering a rich source of nutrients and bioactive compounds.

Discovery of Cinnamic Acid Derivatives as Potent Anti-H. pylori Agents

Antibiotics are currently used for the treatment of Helicobacter pylori (H. pylori), which is confirmed to be the major cause of gastric disorders. However, the long-term consumption of antibiotics has already caused antibiotic resistance and side effects in vivo. Therefore, there is an emerging need for searching for safe and effective anti-H. pylori agents. Inspired by the excellent bioactivities of cinnamic acid, a series of cinnamic acid derivatives (compounds 1–30) were synthesized and determined for H. pylori inhibition. The initial screening revealed that compound 23, a 2,4-dinitro cinnamic acid derivative containing 4-methoxyphenol, showed excellent H. pylori inhibition with an MIC value of 4 μM. Further studies indicated that compound 23 showed anti-bacterial activity and had a bactericidal effect on H. pylori due to the destruction of the bacterial structure. Molecular docking analysis revealed that the 2,4-dinitro groups in cinnamic acid moiety formed hydrogen bonding with amino acid residues in an active pocket of H. pylori protein. Interestingly, the ester moiety fitted into the hydrophobic pocket, attaining additional stability to compound 23. Above all, the present study reveals that compound 23 could be considered a promising anti-H. pylori agent to treat H. pylori causing gastritis.

1,2-Dicinnamoyl-sn-glycero-3-phosphocholine Improves Insulin Sensitivity and Upregulates mtDNA-Encoded Genes in Insulin-Resistant 3T3-L1 Adipocytes: A Preliminary Study.

Insulin resistance is a condition characterized by a reduced biological response to insulin. It is one of the most common metabolic diseases in modern civilization. Numerous natural substances have a positive effect on metabolism and energy homeostasis including restoring the proper sensitivity to insulin. There may be several possible mechanisms of action. In the present study, we elucidated two natural compounds with an impact on insulin signaling in IR adipocytes involving mitochondria. Mature 3T3-L1 adipocytes with artificially induced insulin resistance by palmitic acid (16:0) were used for the study. Cinnamic acid and 1,2-dicinnamoyl-sn-glycero-3-phosphocholin (1,2-diCA-PC) were tested at three concentrations: 25 μM, 50 μM, and 125 μM. The number of mitochondria and the expression of genes encoded by mtDNA were elucidated in control and experimental cells. Experimental cells treated with 1,2-diCA-PC displayed increased insulin-stimulated glucose uptake in a dose-dependent manner, accompanied by an increase in mtDNA copy number. Moreover, in experimental cells treated with 1,2-diCA-PC at a concentration of 125 μM, a significant increase in the expression level of all analyzed genes encoded by mtDNA compared to control cells was observed. Our study showed a relationship between improved cellular sensitivity to insulin by 1,2-diCA-PC and an increase in the number of mitochondria and expression levels of genes encoded by mtDNA. To summarize, the results suggest the therapeutic potential of cinnamic acid derivative 1,2-diCA-PC to enhance the insulin sensitivity of adipocytes.

Integrated Approach for Allyl Amine Synthesis Combining the Decarboxylative Coupling of Arylacrylic Acids with the Petasis Reaction.

A metal-free multicomponent reaction strategy for synthesizing allyl amines through decarboxylative coupling combined with the Petasis reaction is described. Utilizing (E)-3-(2,4,6-trimethoxyphenyl)acrylic acid, various boronic acids, a formaldehyde solution, and primary amines, the method operates efficiently without metal catalysts. Investigations reveal that electron-donating substituents in cinnamic acid derivatives significantly enhance reactivity, which is crucial for effective transformations. Under the optimized conditions, yields of ≤78% were obtained across a diverse range of 30 allyl amines.

Synthesis, Characterization, Spectroscopic, and Electrochemical Investigation of Inclusion Complex of Ethyl Cinnamate with γ‐Cyclodextrin for Antibacterial Studies

AbstractWe synthesized cinnamic acid derivatives of ethyl cinnamate (EC) and analyzed the resulting products using 1H‐NMR and FTIR spectroscopy. The formation of the confirmed EC and γ‐Cyclodextrin inclusion complex is investigated through UV–vis and fluorescence spectroscopy. Cyclic voltammetry techniques are employed to analyze the formation of the inclusion complex. By using Job's plot, the stoichiometric ratio of the inclusion complex is found to be 1:1, and the binding constant (K) is calculated through the Benesi‐Hildebrand plot. Furthermore, we calculated the thermodynamic parameters (ΔG) using the Gibbs‐Helmholtz free energy equation, indicating that the formation of this inclusion complex is spontaneous. The molecular interaction between EC and the hydrophobic cavity of γ‐CD is characterized using 2D NMR (ROESY), revealing their specific interactions. Research highlights the need for antibacterial studies due to the rise of new infectious diseases. Specifically, the study investigates the antibacterial activity of inclusion complexes compared to the guest molecule alone.

Cinnamic Acid Derivatives: Recent Discoveries and Development Strategies for Alzheimer's Disease.

Alzheimer's Disease (AD) is a progressive neurodegenerative disorder that leads to cognitive decline and memory impairment. It is characterized by the accumulation of Amyloid-beta (Aβ) plaques, the abnormal phosphorylation of tau protein forming neurofibrillary tangles, and is often accompanied by neuroinflammation and oxidative stress, which contribute to neuronal loss and brain atrophy. At present, clinical anti-AD drugs are mostly single-target, improving the cognitive ability of AD patients, but failing to effectively slow down the progression of AD. Therefore, research on effective multi-target drugs for AD has become an urgent problem to address. The main derivatives of hydroxycinnamic acid, caffeic acid, and ferulic acid, are widely present in nature and have many pharmacological activities, such as antimicrobial, antioxidant, anti-inflammatory, neuroprotective, anti-Aβ deposition, and so on. The occurrence and development of AD are often accompanied by pathologies, such as oxidative stress, neuroinflammation, and Aβ deposition, suggesting that caffeic acid and ferulic acid can be used in the research on anti-AD drugs. Therefore, in this article, we have summarized the multi-target anti-AD derivatives based on caffeic acid and ferulic acid in recent years, and discussed the new design direction of cinnamic acid derivatives as backbone compounds. It is hoped that this review will provide some useful strategies for anti-AD drugs based on cinnamic acid derivatives.

Structure Modification of Cinnamic Acid to (E)-1-(3,4-dihydroisoquinoline-2(1H)-yl)-3-phenylprop-2-en-1-one and Antioxidant Activity Test by DPPH Method

Antioxidants can protect cells from free radical damage by stabilizing them. One of the compounds that has antioxidant activity is cinnamic acid. Cinnamic acid and its derivatives have several activities: antibacterial, anticancer, and antioxidant. However, the ability of cinnamic acid to capture free radicals is still relatively low. One of the efforts that can be made to increase the antioxidant activity of cinnamic acid is to modify its structure. Structure modification is an effort to improve the pharmacological activity of a compound through chemical synthesis reactions. The cinnamic acid structure can be modified by changing the carboxylic -OH group into an amine group through an N-atom acylation reaction. This study was conducted by reacting cinnamoyl chloride (1a), which is a cinnamic acid derivative with 1,2,3,4-tetrahydroisoquinoline (2b) which is a compound of isoquinoline group to produce (E)-1-(3,4-dihydroisoquinoline-2(1H)-yl)-3-phenylprop-2-en-1-one (3b) and then tested for antioxidant activity using DPPH method. The resulting product compound was yellow crystals with a yield of 81.56%. The antioxidant activity produced by the product is more significant than that of cinnamic acid compounds at the same concentration.

Metabolomic Profiling of Guadua Species and Its Correlation with Antioxidant and Cytotoxic Activities.

Bamboo plants are widely used in Asian traditional medicine for various health issues and exhibit therapeutic potential. Guadua species are renowned bamboos for their high phenolic compound content, including flavonoids and hydroxycinnamic acid derivatives, and possess noteworthy biological properties. Despite this, there is a notable scarcity of research on the chemical and biological aspects of Latin American bamboo leaf extracts (BLEs), especially concerning the Guadua genus. This study aimed to employ a metabolomics approach to integrate the phytochemical and activity profiles of BLEs to identify potential bioactive markers. We determined the metabolic fingerprints of 30 BLEs through HPTLC, HPLC-DAD, UHPLC-QTOF-MS, and 1H-NMR analyses and screened for antioxidant and cytotoxic activities using ABTS, DPPH, and MTT methods. Ultimately, correlation analyses were performed by using chemometric methods and molecular networking. Our findings present a comprehensive chemical characterization, encompassing 40 flavonoids and 9 cinnamic acid derivatives. Notably, most of these compounds have been reported for the first time within the genus, signifying novel discoveries. Additionally, certain compounds identified in other species of the subfamily Bambusoideae provide valuable comparative insights. These compounds demonstrated a significant correlation with antioxidant potential, with values exceeding 100 and 30 μmol of TE/g of extract for ABTS and DPPH, respectively, in the samples. Extracts from G. incana and G. angustifolia exhibited potent cytotoxic effects with IC50 values of 1.23 and 4.73 μg/mL against HCT-116 colon cancer cells, respectively. Notably, glycosylated flavones showed a strong correlation with cytotoxicity. These new findings significantly contribute to our understanding of the chemical composition and biological properties of these often overlooked bamboo species, providing them with important added value and alternative use.

A Review of Cinnamic Acid's Skeleton Modification: Features for Antibacterial-Agent-Guided Derivatives.

Antimicrobial resistance has emerged as a significant danger to global health, and the need for more effective antimicrobial resistance (AMR) control has been highlighted. Cinnamic acid is abundant in plant products and is a potential starting material for further modification, focusing on the development of new antimicrobial compounds. In the following review, we describe the classification of critical antibacterial-guided reactions applied to the main skeleton structure of cinnamic acid derivatives over the last decade. Of all of the main parts of cinnamic acids, the phenyl ring and the carboxylic group significantly affect antibacterial activity. The results presented in the following review can provide valuable insights into considerable features in the organic modification of cinnamic acids related to antibacterial medication development and the food industry.

It Is Not All about Alkaloids-Overlooked Secondary Constituents in Roots and Rhizomes of Gelsemium sempervirens (L.) J.St.-Hil.

Gelsemium sempervirens (L.) J.St.-Hil. is an evergreen shrub occurring naturally in North and Middle America. So far, more than 120 alkaloids have been identified in this plant in addition to steroids, coumarins and iridoids, and its use in traditional medicine has been traced back to these compound classes. However, a comprehensive phytochemical investigation of the plant with a special focus on further compound classes has not yet been performed. Therefore, the present study aimed at an extensive HPLC-MSn characterization of secondary metabolites and, for the first time, reports the occurrence of various depsides and phenolic glycerides in G. sempervirens roots and rhizomes, consisting of benzoic and cinnamic acid derivatives as well as dicarboxylic acids. Furthermore, mono- and disaccharides were assigned by GC-MS. Applying the Folin-Ciocalteu assay, the phenolic content of extracts obtained with different solvents was estimated to range from 30 to 50% calculated as chlorogenic acid equivalents per g dry weight and was related to the DPPH radical scavenging activity of the respective extracts. Upon lactic acid fermentation of aqueous G. sempervirens extracts, degradation of phenolic esters was observed going along with the formation of low-molecular volatile metabolites.

Identification of Fatty Acids, Amides and Cinnamic Acid Derivatives in Supercritical-CO2 Extracts of Cinnamomum tamala Leaves Using UPLC-Q-TOF-MSE Combined with Chemometrics.

Cinnamomum tamala leaf (CTL), also known as Indian bay leaf, is used all over the world for seasoning, flavoring, and medicinal purposes. These characteristics could be explained by the presence of several essential bioactive substances and lipid derivatives. In this work, rapid screening and identification of the chemical compounds in supercritical (SC)-CO2 extracts of CTL by use of UPLC-Q-TOF-MSE with a multivariate statistical analysis approach was established in both negative and positive mode. A total of 166 metabolites, including 66 monocarboxylic fatty acids, 52 dicarboxylic fatty acids, 27 fatty acid amides, and 21 cinnamic acid derivatives, were tentatively identified based on accurate mass and the mass spectrometric fragmentation pattern, out of which 142 compounds were common in all SC-CO2 extracts of CTL. Further, PCA and cluster hierarchical analysis clearly discriminated the chemical profile of analyzed extracts and allowed the selection of SC-CO2 extract rich in fatty acids, fatty acid amides, and other bioactive constituents. The result showed that the higher number of compounds was detected in CTL4 (300 bar/55 °C) extract than the other CTL extracts. The mono- and di-carboxylic fatty acids, fatty acid amides, and cinnamic acid derivatives were identified in CTL for the first time. UPLC-Q-TOF-MSE combined with chemometric analysis is a powerful method to rapidly screen the metabolite profiling to justify the quality of CTL as a flavoring agent and in functional foods.