Acid Esters Research Articles

Synthesis and structural characterization of a new colchicine monosquarate-amide derivative

Colchicine is a compound isolated from Colchicum autumnale, which is characterized by high anticancer activity. A new amide derivative of colchicine with a squaric acid ester skeleton has been synthesized by the reaction between deacetylated thiocolchicine and diethyl ester of squaric acid. The synthesis under optimized reaction conditions gave the desired product (colchicine monosquarate-amidoester - 5) in the excellent yield of 90%. This compound crystallizes in the non-centrosymmetric space group P21 of the monoclinic system as dihydrate (5‧2H2O) which was confirmed by the X-ray analysis of the single crystal at room temperature. As the temperature decreases to 100 K, the crystal partially loses water that was also confirmed by X-ray single crystal analysis. The obtained amidoester 5 has been analyzed by NMR (1D and 2D), FT-IR and ESI-MS spectroscopy. At room temperature the 1H and 13C NMR spectra showed doubling of signals, which suggested that in the solution, the product existed as rotamers. This hypothesis was confirmed using variable–temperature (VT) 1H NMR and 13C NMR spectroscopies.

Esterification of caprylic acid with glycerol for medium chain glycerides production catalyzed by waste coconut shell derived sulfonated carbon catalysts

Esterification of caprylic acid with glycerol for medium chain glycerides production catalyzed by waste coconut shell derived sulfonated carbon catalysts

Bacterial Catabolism of Phthalates With Estrogenic Activity Used as Plasticisers in the Manufacture of Plastic Products.

Phthalic acid esters (PAEs), the pervasive and ubiquitous endocrine-disrupting chemicals of environmental concern, generated annually on a million-ton scale, are primarily employed as plasticisers in the production of a variety of plastic products and as additives in a large number of commercial supplies. The increased awareness of various adverse effects on the ecosystem and human health including reproductive and developmental disorders has led to a striking increase in research interest aimed at managing these man-made oestrogenic chemicals. In these circumstances, microbial metabolism appeared as the major realistic process to neutralise the toxic burdens of PAEs in an ecologically accepted manner. Among a wide variety of microbial species capable of degrading/transforming PAEs reported so far, bacteria-mediated degradation has been studied most extensively. The main purpose of this review is to provide current knowledge of metabolic imprints of microbial degradation/transformation of PAEs, a co-contaminant of plastic pollution. In addition, this communication illustrates the recent advancement of the structure-functional aspects of the key metabolic enzyme phthalate hydrolase, their inducible regulation of gene expression and evolutionary relatedness, besides prioritising future research needs to facilitate the development of new insights into the bioremediation of PAE in the environment.

Synthesis, biological evaluation and mechanism study based on network pharmacology of amino acids esters of 20(S)-protopanaxadiol as novel anticancer agents

As one of the metabolites of ginseng, 20(S)-protopanaxadiol (PPD) is a compound with dammarane-type tetracyclic triterpene, which performs a wide range of anticancer activities. In this study, PPD was used as a lead. A series of compounds were synthesized respectively with 11 amino acids through esterification and were evaluated for their cytotoxicity against several cancer cell lines. One of the synthetic products (PL) exhibited potent inhibitory effect on Huh-7 cells relative to that of PPD in vitro. Subsequently, the Annexin V-FITC /PI staining assay was used to verify that PL induced apoptosis of Huh-7 cells in a dose-dependent manner. A UPLC-Q/TOF-MS analysis method was established and validated for assessing pharmacokinetic properties after the administration of PPD and PL in rats. The results showed that compared with PPD, T1/2of PL in rats was prolonged, and the peak time was delayed, resulting in broader tissue distribution of the compound in the body. In addition, the targets of PL against several cancers were predicted and analyzed via network pharmacology. Molecular docking simulations demonstrated that PL interacted with the active sites of the above targets. In conclusion, this study provided a theoretical basis for the development and clinical application of anti-tumor activity of PPD.

Enhancing Bone-Titanium integration through hydrogel coating mediated sequential M1/M2 polarization of interfacial macrophages

Regulating phenotypes of in situ macrophages (Mφ) is a cutting-edge strategy for promoting bone-Titanium (Ti) integration, but what is the most rational modulation manner has long been controversial. Short-term inducing in situ M1 Mφ polarization or inducing in situ M2 Mφ polarization have proven to be capable of promoting osseointegration. However, an increasing number of researches have claimed that sequentially inducing in situ M1/M2 Mφ polarization, compared to the above-mentioned two strategies, could further enhance osseointegration. In this work, we compared the capability of the three different modulation manners to promote osseointegration. Briefly, we anchored a homogeneous Poly(HEMA-co-3APBA)/LUT/SOP hydrogel coating, which could sequentially release pro-inflammatory sophoridine (SOP) molecules and anti-inflammatory luteolin (LUT) molecules through pH mediated conformational transition of phenylboronic acid ester bonds, on the surface of Ti implants. Ti implants coated with the Poly(HEMA-co-3APBA)/SOP hydrogel or the Poly(HEMA-co-3APBA)/LUT hydrogel, which merely released SOP molecules and LUT molecules respectively, were utilized as controls. In vitro Mφ co-culture assays proved the immunoregulation functions of different hydrogel coatings in inducing Mφ polarization, and the rationale behind which was identified to be related to the PI3K-AKT signaling pathways. In addition, the immunoregulation mediated osteogenic differentiation behaviors of bone marrow mesenchymal stem cells (BMSCs) were also investigated. Implantation of as-prepared Ti nails to a rat femur defect model followed by evaluations of H&E staining, Masson staining, immunohistochemical staining, etc. proved the stronger capability to enhance osseointegration of inducing sequential M1/M2 Mφ polarization than short-term inducing in situ M1 Mφ polarization or inducing in situ M2 Mφ polarization. This work not only reported a novel Ti implant with superior osseointegration capability but also will inspire corresponding researches in the future.

Combination of Milk Polar Lipids and Casein Hydrolysate as a Healthy Emulsifier for Ice Cream.

The demand for healthy ingredients in food products including ice cream, is continuously increasing. The potential of a combination of milk polar lipids (MPL) and casein hydrolysate (CH) to replace synthetic emulsifiers such as diacetyl tartaric acid esters of monoglycerides (DATEM), in ice cream production was investigated. Changes in particle size, emulsion stability, and interfacial tension of model emulsions (milk protein, casein:whey=8:2, w/v) were analyzed after the addition of MPL, CH, and their combination (MPL+CH). The use of MPL+CH reduced interfacial tension and increased αs- and β-casein displacement from the surface of cream layers compared to the addition of MPL alone. The addition of MPL+CH improved ice cream overrun to levels comparable to those of control ice cream containing DATEM (0.3%, w/v), without adversely affecting melt rate or microstructure. Confocal laser scanning microscopy revealed that ice cream prepared with MPL+CH formed a thick protein and coalesced fat layer on the surface of air cells that might help enhance overrun. These findings suggest that the combination of MPL (0.3%, w/v) and CH (0.03%, w/v) can be used as a potential emulsifier alternative to replace chemically synthesized emulsifiers such as DATEM.

Deoxofluorination of pyridinyloxoacetates by sulfur tetrafluoride

An effective scalable method for the synthesis of -, -, and -pyridinyloxoacetates has been developed, based on the interaction of the respective bromopyridines with diethyl oxalate in the presence of isopropylmagnesium chloride. This method enables the preparation of all isomeric pyridinyl oxoacetates with preparative yields in multigram quantities. The deoxofluorination process of isomeric pyridinyl oxoacetates with sulfur tetrafluoride was investigated. It was established that the deoxofluorination of - and -pyridinyloxoacetates with sulfur tetrafluoride leads to the formation of a mixture of -/-pyridinyldifluoroacetic acid esters and -/-pyridinyltetrafluorinated ethers, which can be separated chromatographically. It was found that when using an excess of sulfur tetrafluoride and prolonged heating of the reaction mixture, the fluorination of -/-pyridinyl oxoacetates results in the exclusive formation of -/-pyridinyltetrafluorinated ethers. On the other hand, in the case of deoxofluorination of -pyridinyloxoacetate with sulfur tetrafluoride, varying the temperature and the amount of fluorinating reagent allows for the selective formation of -pyridinyldifluoroacetic acid ester or -pyridinyltetrafluorinated ether. -/-/-Pyridinyltetrafluorinated ethers are new representatives of the small group of hetaryltetrafluorinated ethers and have potential applications in medicine and agrochemistry.

Basicity-tuned graphitic carbon nitride supported MgO heterogeneous catalysts for efficient transesterification of groundnut oil to biodiesel

Quality and quantity of biodiesel derived from oil depend on the type of feedstock and the transesterification process. To maximize biodiesel production efficiency and ensure the desired fuel quality, it is crucial to develop and optimize feedstock-specific production processes. This study reports on the transesterification of groundnut oil using a heterogeneous catalyst. Magnesium oxide (MgO) and its composites with graphitic carbon nitride (g-C3N4) at 10, 30, and 50 wt% (MG10, MG30, MG50) were used. The composite catalyst combines basic sites from MgO and Lewis acid sites from the nitrogen atoms in the g-C3N4 triazine unit, giving rise to synergistic effects that enhances biodiesel production. MgO nanoparticles were synthesized via precipitation, followed by calcination at 500 °C, and MgO/g-C3N4 composites were prepared by grinding at different ratios. Morphological and structural studies confirmed material characteristics. BET analysis indicated an increased surface area of 71.39 m2/g, enhancing catalytic activity, while SEM revealed the agglomerated g-C3N4 and the cubic morphology of MgO. Response surface methodology was used to optimize catalyst loading, temperature, and reaction time parameters. The optimal conditions for biodiesel conversion using MG50 composite was determined to be methanol/oil ratio of 6:1, 2.5 wt% catalyst loading, 41.7 °C reaction temperature and spanning 52 min of reaction, yielding 94 % efficiency. GC–MS analysis confirmed successful transesterification, identifying key fatty acid esters such as ethyl oleate (34.72 %) and hexadecanoic acid methyl ester (7.69 %). This work supports further research into feedstock-specific catalysts for industrial biodiesel applications.

An In Vitro, In silico, GCMS and LCMS Investigation of Crinum jagus (J. Thomp.) Dandy Bulb for Lead Anti-Hepatocellular Carcinoma Compounds

Hepatocellular carcinoma is a leading cause of cancer-related death around the world. In this study, the 3-(4, 5-dimethylthiazolyl-2)-2, 5-diphenyltetrazolium bromide (MTT) assay was used to investigate the anticancer activity of five chromatographic fractions of Crinum jagus methanol bulb extract against the hepatocellular carcinoma (HepG2) cell line. The IC50 value was used as a measure of anticancer activity. The most active fraction was analyzed using GCMS and LCMS. The binding energies of the identified compounds with Caspase-3, Caspase-9 and EGFR were evaluated and compared with that of the standard drug, Sorafenib. The compounds' drug-likeness was evaluated by applying Lipinski's rule of five. The IC50 value of the most active fraction was 37 μg/ml. Nineteen (19) compounds, primarily fatty acids, fatty acid esters, and flavonoids, were identified from the fraction by GCMS and LCMS analysis. Of the nineteen (19) compounds identified in the most active fraction, linoelaidic acid (-8.23 kcal mol-1), hexadecanoic acid (-7.96 kcal mol-1) and 9,12-Octadecadienoic acid (-7.78 kcal mol-1) had better binding affinity for Caspase-3 than Sorafenib; hexadecanoic acid methyl ester (-8.10 kcal mol-1) and pentyl linoleate (-8.00 kcal mol-1) had comparable binding energy with Sorafenib (-8.47 kcal mol-1) against Caspase-9; while hexadecanoic acid (-8.29 kcal mol-1), linoelaidic acid (-8.58 kcal mol-1), and pentyl linoleate (-8.66 kcal mol-1) had better binding energy than Sorafenib (-8.24 kcal mol-1) against EGFR. These compounds passed Lipinski’s test for drug-likeness. The study's findings lend credence to the plant's traditional use as a cancer remedy.

Recent advances of optical sensors for point-of-care detection of phthalic acid esters

Phthalic acid esters (PAEs) are often added to plastics to enhance elasticity, transparency, durability and prolong service life as a kind of plasticizer. However, they are not chemically bonded to polymers and are difficult to degrade, which makes it easy for them to release into the environment and enter the human body from various potential sources. This results in environmental pollution and poses health risks. In order to protect ecosystem, ensure food safety and prevent disease, there is an urgent need for sensors that can achieve point-of-care detection of PAEs. Optical sensors have advantages of simplicity, portability and low cost, and have been widely applied to the detection of PAEs. In this review, we focus on introducing the recent advancements and trends in optical sensors for detection of PAEs represented by colorimetric (CL) sensors, fluorescence (FL) sensors and surface-enhanced Raman scattering (SERS) platform. Based on recognition strategies (e.g., label-free, aptamer, molecularly imprinted polymer, antibody and enzyme), the significant achievements of these optical sensors in the past 5 years are systematically classified and described in detail. Researchers can quickly know the development status of optical sensors for detection of PAEs in the past 5 years. This review highlights the strengths of each sensor type while also identifying their application limitations, providing researchers with valuable insights into future directions for optical sensor research.

Evaluation of Fuel Consumption and Exhaust Emissions in a Single Cylinder Four-Stroke Diesel Engine Using Biodiesel Derived from Chicken Waste with Additives

Biodiesel is a renewable, locally generated fuel made from vegetable oils, trans fats, or recycled restaurant grease for use in diesel automobiles and other diesel-powered equipment. The physical qualities of biodiesel are comparable to those of petroleum diesel. Biodiesel is used in compression-ignition engines in the same way as petroleum diesel. Biofuel can be made from biomass, but according to the Indian National Policy on Biofuels, biofuel extraction from edible oils is not permitted because it would result in a massive increase in consumer goods prices and perhaps lead to product scarcity. Hence, there is a need to search for alternative biofuel so that it does not affect our nation's national policy. Recently there has been a drastic increase in the consumption of chicken grown in farms. There is a huge problem in disposing of their waste. One major difficulty in waste treatment is poultry manure, often known as slaughter waste. This waste is sometimes dumped on wastelands, roadsides, and the banks of rivers, lakes, and ponds. This creates more sanitary problems for society. According to polls, poultry feces begin to decompose in around three hours. The odor of butcher's waste causes a lot of pollution in the air, as well as an increase in the density of bacteria in the atmosphere. Measures have been taken by the government for the safe disposal of these wastes. One of the major ways of disposal is to recycle this chicken slaughter waste in a useful manner so that it can serve society in a positive way. This could be done by converting this waste into fuel through various processes such as rendering, hydrolysis, extraction, acid esterification, alkaline transesterification, and finally by the extraction process. This produced fuel could be blended with existing diesel in varying concentrations and used in diesel engine-powered vehicles. In this work, the fuel is extracted from the chicken waste and blended with pure diesel and an Al2O3 additive in various proportions. These combinations are then tested on a single-cylinder diesel engine for fuel consumption and emission analysis. The results exhibited an overall better performance when compared to pure diesel.

Environmental monitoring of phthalic acid esters in northwest Persian Gulf estuary: Concentrations, distribution, and risk assessment

The present study investigates the concentration level, distribution, and risk assessment of six high-priority phthalic acid esters (PAEs) in seawaters and sediments of the Musa estuary, northwest of the Persian Gulf, Iran. Additionally, the industrial and urban effluents terminating in this estuary were also analyzed. The overall variations of Σ6PAEs were 10.65–164.80 µg/L in seawaters, 0.53–26.18 µg/g in sediments, and 181.09–764.57 µg/L in effluent samples. Di–n–butyl phthalate (DnBP) and di(2–ethylhexyl) phthalate (DEHP), together accounted for 57.2 %–99.5 % and 59 %–100 % of the Σ6PAEs concentrations in seawaters and sediments, respectively. A relatively similar trend was also detected in the effluent waters. While industrial runoffs exhibited greater shares and concentrations compared to urban areas, the levels of PAEs were higher in waters and sediments near urban regions due to restricted water circulation. A significant correlation was found (r = 0.8385) between Σ6PAEs in seawater and sediment. Given its consistent detection frequency of 100 % across all stations, DEHP can be served as a reliable indicator for PAE contamination. In nearly all stations, the pollution levels of DnBP and DEHP exceeded the environmental risk level (ERL). The ecological risk quotient (RQ) for at least two PAEs appeared at medium to high levels in both seawaters and sediments. Establishing baseline data on PAEs in the Musa estuary will guide future strategies for pollutant control across the Persian Gulf network.

BF3 ⋅ OEt2 as a Versatile Reagent: Applications in Organic Synthesis

AbstractBoron trifluoride diethyl etherate, commonly referred to as BF3 ⋅ OEt2, plays a crucial role as a potent reagent in various organic transformations, particularly in the synthesis of heterocyclic systems through the establishment of carbon‐carbon & carbon‐heteroatom bonds. Its Lewis acid properties, reactivity, and stability at room temperature make it essential for a wide range of chemical reactions. BF3 ⋅ OEt2 demonstrates remarkable efficacy in processes such as hydroxylation of double bonds, epoxide cleavage, acid esterification, cyanation, coupling, and diverse cyclization reactions, surpassing other Lewis acids in performance. Its significant impact on organic synthesis extends to the formation of natural products, highlighting its profound significance in the realm of chemistry. The unique properties and versatility of boron trifluoride diethyl etherate make it a fundamental tool for a diverse array of chemical transformations. The numerous applications of this reagent in organic synthesis have prompted the development of a comprehensive review, focusing on its various roles and contributions in this field.

Biobased Self-Healing Thin Film Coatings Based on Poly (Itaconic Acid Esters).

Paper used for packaging applications is often coated with thin polymer coatings to improve the properties, like printability and barrier properties, respectively. Today, these coatings are still often based on petroleum-based polymers. In this study, the fabrication of biobased thin film coatings is described. Poly(itaconic acid ester)s, which are prepared by emulsion polymerization, are used as water-based coatings for paper. The thermal properties of the polymers are tuned by the side chain of the monomers (diethyl itaconate vs. dibutyl itaconate). Different formulations based on the polymer emulsion and additives, like rheology modifiers, are prepared and their film formation is studied. The usage of a rheology modifier results in excellent film formation. These polymer coatings feature an additional function - they are capable of self-healing. The healing ability is studied in scratch healing tests, in which almost complete recovery can be observed after healing at 100 °C. Moreover, the restoration of optical properties/aesthetics is studied. In gloss measurements before and after damage as well as after a healing time the complete recovery of the gloss can be observed. Furthermore, the barrier properties against fat are studied.

Migration patterns of phthalic acid esters from mulch plastic film in the soil-plant-atmosphere continuum system

Plastic film mulching is an important agricultural practice, but its release of phthalic acid esters (PAEs) poses threats to soil and human health. However, the migration patterns of PAEs during the lifecycle of mulch plastic film (MPF) remain unclear. This study aims to explore the temporal patterns of release of PAEs during the MPF's lifecycle and evaluate the migration patterns of PAEs from MPF in the soil-plant-atmosphere continuum (SPAC) system through pot experiments and model simulations. The results reveal that during the mulching period, 44.90–56.71 % of the PAEs released went into the atmosphere and 14.97–18.90 % into the soil, while during the residual film period, 24.39–40.13 % were slowly released into the soil. Elevated soil water content increased maize transpiration rates, leading to higher concentrations of PAEs in roots, stems, and fruits, but lower concentrations in leaves. In 2020, the estimated total release of PAEs from MPF in northwest China amounted to 35.42 tons. Notably, PAEs predominantly accumulated in the soil, with minimal accumulation in plant tissues. Moreover, PAEs were primarily removed through degradation. Our results elucidate the migration patterns of PAEs from MPF in the SPAC system, facilitating the evaluation of PAE pathways into the human food chain.

Furano‐ and Thieno‐Fused Carbazole‐Containing Azaborines and Their π‐Extension: Synthesis, Structures, and Properties

AbstractA series of carbazole‐containing azaborines, furano‐fused 1–2F and 1–3F and thieno‐fused 1–2T and 1–3T, were efficiently synthesized from a common carbazole boronic acid ester in two steps. The structural effects of the fused ring moieties and the patterns of the ring fusion were clarified. According to X‐ray crystal structure analysis, the furano‐ and thieno‐fused carbazole azaborines had planar structures and generally formed 1D columns. UV–vis analysis revealed that their absorption properties were significantly affected by the fused ring moieties. In contrast, the fluorescence properties were affected by the ring fusion patterns. π‐Extended derivatives of 1–2T and 1–3T, benzothieno‐fused 1–2BT and 1–3BT and phenyl‐substituted 1–2T‐Ph2 and 1–3T‐Ph2 were synthesized, and the effects of π‐extension on physical properties were also investigated. All the π‐extended compounds showed red‐shifts in absorption and fluorescence spectra compared with the pristine 1–2T and 1–3T. The color of solid‐state emission of the synthesized azaborines was tuned from purple to green without electron‐rich or ‐deficient substituents. The structural effects on the electronic structures were also discussed based on theoretical calculations.

Novel metabolomic predictors of incident colorectal cancer in men and women.

Metabolomic profiles may influence colorectal cancer (CRC) development. Few studies have performed pre-diagnostic metabolome-wide analyses with CRC risk. We conducted a nested case-control study among women (Nurses' Health Study (NHS)) and men (Health Professionals Follow-up Study (HPFS)) who provided blood between 1989 and 1995. Over 22.9 years, 684 (409 NHS, 275 HPFS) incident CRC cases occurred and were matched 1:1 to controls. Liquid chromatography-mass spectrometry (LC-MS) identified 255 plasma metabolites after quality control. Cohort-specific and combined metabolite association analyses were performed using conditional logistic regression. Metabolite set enrichment analysis (MSEA) was used to identify differential abundance in metabolite classes. Weighted Correlation Network Analysis (WGCNA) provided modules of covarying metabolites, which were tested for CRC association. MSEA identified specific acylcarnitines associated with higher CRC risk and triacylglycerols with lower CRC risk among women and men. Further, phosphatidylcholines were associated with a higher risk of CRC among men. In an analysis restricted to CRC cases diagnosed two years after blood draw, myristoleic acid (OR = 1.37; 95%CI = 1.15-1.62; FDR = 0.072) and C60:12 triacylglycerol (OR = 0.75; 95%CI = 0.64-0.88; FDR = 0.072 were associated with CRC risk in women. WGCNA identified amino acids associated with CRC in men, fatty acid esters (carnitines) with distal CRC in men, and triradylcglycerols inversely associated with CRC in women. We identified pre-diagnostic CRC-associated metabolites with distinct sex-specific profiles. These results provide insight into CRC etiopathogenesis and have implications for risk prediction strategies.

Sustainable Synthesis of New Antioxidants from Hydroxytyrosol by Direct Biocatalytic Esterification in Ionic Liquids.

Hydroxytyrosol (HT) is a nutraceutical compound, mainly found in the fruit, leaves and waste from the olive oil industry, known for exhibiting one of the highest antioxidant activities among molecules of natural origin. To harness this bioactivity in cosmetics, pharmaceuticals and the food industry, it is essential to modify the hydrophilicity of HT to enhance its compatibility with lipid-based mixtures. This chemical modification must be carried out with high selectivity to avoid compromising its radical scavenging activity. This work presents a highly efficient and selective approach to perform the biocatalytic esterification of free fatty acids (FFAs) of different alkyl chain lengths with HT in a reaction medium based on the SLIL [C12mim][NTf2]. By using a 1:2 (mol/mol) HT:FFA mixture of substrates, the HT-monoester derivative was obtained up to 77% yield after 2 h at 80 °C. The optimized molar ratio of substrates, combined with the ability to recover the SLIL for further reuse, significantly reduces waste accumulation compared to other reported strategies and results in a more sustainable approach as demonstrated by different green metrics. The antioxidant activity of HT-monoester products was fully maintained with respect to that presented by the natural HT, being stable for at least 3 months at 4 °C, as demonstrated by the DPPH and FRAP antioxidant analysis.

Azaspiracid-59 accumulation and transformation in mussels (Mytilus edulis) after feeding with Azadinium poporum (Dinophyceae)

Azaspiracid-59 (AZA-59) was detected in plankton in coastal waters of the Pacific Northwest USA. Given that bivalves metabolize and transform accumulated phycotoxins, a strain of Azadinium poporum isolated from the coast of Washington State that is a known producer of AZA-59 was used in a controlled feeding experiment with mussels (Mytilus edulis) to assess AZA-59 accumulation rates and transformation into shellfish metabolites. Mussels started feeding immediately after the addition of A. poporum. Mussels were generally healthy during the entire experimental exposure of 18 days with prevailingly high rates of clearance (approx. 100 mL per mussel per hour) and ingestion. Mussels were extracted after different exposure times and were analyzed by liquid chromatography coupled with low- and high-resolution mass spectrometry. In the course of the experiment a number of putative AZA-59 metabolites were detected including hydroxyl and carboxy analogues that corresponded with previously reported mussel metabolites of AZA-1. A significant formation of 3-OH fatty acid acyl esters relative to free AZAs was observed through the time course of the study, with numerous fatty acid ester variants of AZA-59 confirmed. These results illustrate the potential for metabolism of AZA-59 in shellfish and provide important information for local AZA monitoring and toxicity testing along the Northern Pacific US coast.

Phytoconstituents, Antioxidant Activity and Cytotoxicity of Puya chilensis Mol. Extracts in Colon Cell Lines.

Puya chilensis Mol. is a plant of the Bromeliaceae family, which has been traditionally used for medicinal applications in various digestive disorders. In this study, the phytoconstituents of six extracts of stems and flowers of P. chilensis were evaluated: phenols, flavonoids and total anthraquinones, as well as their antioxidant capacity and cytotoxicity in colon cancer cell lines HT-29. The data demonstrate that the ethyl acetate extract of P. chilensis flowers is cytotoxic in HT-29 cell lines (IC50 = 41.70 µg/mL) without causing toxic effects on healthy colon cells (IC50 > 100 µg/mL); also, this extract concentrated the highest amount of phenols (4.63 μg GAE/g d.e.), flavonoids (31.5 μg QE/g d.e.) and anthraquinones (12.60 μg EE/g d.e.) among all the extracts tested, which also correlated with its highlighted antioxidant capacity (DPPH∙IC50 = 4.15 mg/mL and FRAP 26.52 mM TEAC) over the other extracts. About thirty-five compounds were identified in this extract-the fatty acid esters present have been shown to have therapeutic effects on several types of cancer and could explain its antiproliferative activity.