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Keywords = methyl propanoate

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19 pages, 2360 KiB  
Article
Novel N-Alkyl 3-(3-Benzyloxyquinoxalin-2-yl) Propanamides as Antiproliferative Agents: Design, Synthesis, In Vitro Testing, and In Silico Mechanistic Study
by Samar A. Abubshait
Molecules 2025, 30(14), 3025; https://doi.org/10.3390/molecules30143025 - 18 Jul 2025
Viewed by 489
Abstract
A series of eleven new N-alkyl 3-(3-benzyloxyquinoxalin-2-yl) propanamides were prepared based on the azide coupling of 3-(3-benzyloxyquinoxalin-2-yl) propanhydrazide with a variety of primary and secondary amines and the consequent conjunction of a broad spectrum of lipophile and hydrophile characters to a quinoxaline [...] Read more.
A series of eleven new N-alkyl 3-(3-benzyloxyquinoxalin-2-yl) propanamides were prepared based on the azide coupling of 3-(3-benzyloxyquinoxalin-2-yl) propanhydrazide with a variety of primary and secondary amines and the consequent conjunction of a broad spectrum of lipophile and hydrophile characters to a quinoxaline ring system. 3-(3-benzyloxyquinoxalin-2-yl) propanhydrazide was produced in a two-step reaction of methyl 3-(3-oxo-3,4-dihydroquinoxalin-2-yl) propanoate with benzyl chloride followed by the hydrazinolysis of the corresponding ester. The antiproliferative activity of the compounds was tested in various cancer cell lines, including PC-3, Hela, HCT-116, and MCF-7; they showed a wide spectrum of activity for most of the tested compounds. Compound 6k exhibited the highest activity, which was comparable to that of doxorubicin, with IC50 (µM) values of 12.17 ± 0.9, 9.46 ± 0.7, 10.88 ± 0.8, and 6.93 ± 0.4 µM compared to 8.87 ± 0.6, 5.57 ± 0.4, 5.23 ± 0.3, and 4.17 ± 0.2 µM for doxorubicin against Hela, HCT-116, and MCF-7, respectively. The in silico mechanistic study revealed the inhibition of HDAC-6 through the binding of the unique zinc finger ubiquitin-binding domain (HDAC6 Zf-UBD). The docking results showed a specific binding pattern that emphasized the crucial role of the quinoxaline ring and its substituents. The newly developed derivatives were evaluated for antitumor effects against four cancer cell lines PC-3, HeLa, HCT-116, and MCF-7. This research led to the identification of a quinoxaline-based scaffold exhibiting broad-spectrum antiproliferative activity and a distinct mechanism involving binding to HDAC6 Zf-UBD. The findings highlight its potential for further optimization and preclinical studies to support future anticancer drug development. Full article
(This article belongs to the Special Issue Molecular Docking in Drug Discovery, 2nd Edition)
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21 pages, 4837 KiB  
Article
Potential of Pandan Root and Teak Leaf Extracts in Managing Maternal Hyperglycemia During Pregnancy: Comparative Efficacy and Mechanistic Insights
by Sasitorn Kerdsuknirund, Panida Khunkaewla, Pakanit Kupittayanant, Suthida Chanlun, Pattama Tongdee, Porntip Nimkuntod and Sajeera Kupittayanant
Int. J. Mol. Sci. 2025, 26(12), 5506; https://doi.org/10.3390/ijms26125506 - 9 Jun 2025
Viewed by 744
Abstract
Maternal hyperglycemia during pregnancy poses significant health risks to both mother and fetus. Although gestational diabetes mellitus (GDM) is mainly characterized by insulin resistance, severe hyperglycemia may also result from impaired pancreatic function. This study evaluates the therapeutic potential of pandan (Pandanus [...] Read more.
Maternal hyperglycemia during pregnancy poses significant health risks to both mother and fetus. Although gestational diabetes mellitus (GDM) is mainly characterized by insulin resistance, severe hyperglycemia may also result from impaired pancreatic function. This study evaluates the therapeutic potential of pandan (Pandanus amaryllifolius) root and teak (Tectona grandis) leaf extracts in managing streptozotocin (STZ)-induced maternal hyperglycemia in pregnant rats, compared to metformin. Methods: Pregnant rats were administered STZ (60 mg/kg) on gestation day 5. Treatments with metformin (300 mg/kg), pandan extract (low, medium, high doses), and teak extract (low, medium, high doses) were given from gestation day 7 to 21. The key parameters included the maternal blood glucose, insulin levels, pancreatic morphology, fetal and placental outcomes, and gas chromatography/mass spectrometry (GC/MS) phytochemical profiling. GC/MS analysis identified 2,3-butanediol and propanoic acid derivatives as major compounds in pandan, while teak contained catavic acid and methyl copalate. The high-dose pandan extract significantly reduced the maternal blood glucose (p < 0.05), improved the insulin levels and pancreatic mass index, and increased the number of live fetuses, with effects comparable to metformin. The teak extract showed milder improvements. The pandan extract demonstrated dose-dependent antidiabetic potential in this STZ-induced model. Future studies should evaluate these effects in insulin-resistance-based GDM models. Full article
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27 pages, 7352 KiB  
Article
Sensing of Volatile Organic Compounds by Haller’s Structure in Ixodidae Tick: Electroscutumography and Olfactometric Bioassay
by Alivia Mandal, Bishwajeet Paul, Biswanath Bhowmik, Raja Reddy Gundreddy, Adolat U. Mirzaieva and Kakali Bhadra
Biosensors 2025, 15(6), 358; https://doi.org/10.3390/bios15060358 - 4 Jun 2025
Viewed by 753
Abstract
Background: Chemosensation in ticks opens a novel and unique field for scientific research. This study highlights ticks’ chemosensory system to comprehend its host-searching behavior and other integrated chemistry and biology involving Haller’s structure. Methodology: This study combines microanatomical, electrophysiological, and behavioral experiments to [...] Read more.
Background: Chemosensation in ticks opens a novel and unique field for scientific research. This study highlights ticks’ chemosensory system to comprehend its host-searching behavior and other integrated chemistry and biology involving Haller’s structure. Methodology: This study combines microanatomical, electrophysiological, and behavioral experiments to investigate the role of Haller’s organ in adult ticks in response to different classes of organic compounds. Results: We showed the microscopic anatomy of Haller’s organ in Haemaphysalis darjeeling, present at the terminal segment of the first pair of appendages. Haller’s structure serves a vital function in perceiving odor. The electrophysiological activity of adult ticks to different classes of organic compounds via electroscutumography was explored at five different concentrations: w/v 0.001, 0.01, 0.1, 1.0, and 2.0%. Among 55 organic compounds, moderate to high stimulation was recorded with pyruvate (13.28 mv at 2%), ammonia (12.26 mv at 2%), benzoic acid (1.99 mv at 0.001%), isobutyric acid (1.39 mv at 0.001%), 2,6-dichlorophenol (1.34 mv at 0.001%), p-Tolualdehyde (1.26 mv at 2%), tetradecane (1.23 mv at 2%), docosane (1.17 mv at 2%), citronellal (1.13 mv at 0.1%), isopropyl acetate (1.05 mv at 0.01%), cyclohexanol (1.03 mv at 2%), 1-octane-3-ol (1.02 mv at 2%), and 1-octanol (1.01 mv at 0.001%). Olfactometric bioassays at w/v 2.0% concentration further confirmed that ammonia, pyruvate, 1-octane-3-ol, hematin porcine, p-Tolualdehyde, methyl salicylate, uric acid, tetradecane, carbon dioxide, propanoic acid, 3-hexanol, hexanoic acid, adenine, 2,6-dichlorophenol, hexadecane, heptanoic acid, pentanoic acid, octadecane, guanine, and nonanoic acid acted as strong attractants, while citronellal, eugenol, butyric acid, geraniol, benzaldehyde, and tiglic aldehyde showed an active repellent effect against the tick species. Conclusions: This investigation provides knowledge of the olfactory sensilla of Haller’s structure as biosensors behind tick olfaction and the possibility for chemical detection of diverse attractants and repellents for future development of anti-tick compounds. Full article
(This article belongs to the Section Environmental Biosensors and Biosensing)
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16 pages, 5763 KiB  
Article
Anti-Inflammatory Potential and Synergic Activities of Eclipta prostrata (L.) L. Leaf-Derived Ointment Formulation in Combination with the Non-Steroidal Anti-Inflammatory Drug Diclofenac in Suppressing Atopic Dermatitis (AD)
by Muhammad M. Poyil, Mohammed H. Karrar Alsharif, Mahmoud H. El-Bidawy, Salman Bin Dayel, Mohammed Sarosh Khan, Zainab Mohammed M. Omar, Alaaeldin Ahmed Mohamed, Reda M. Fayyad, Tarig Gasim Mohamed Alarabi, Hesham A. Khairy, Nasraddin Othman Bahakim, Mohamed A. Samhan and Abd El-Lateef Saeed Abd El-Lateef
Life 2025, 15(1), 35; https://doi.org/10.3390/life15010035 - 30 Dec 2024
Cited by 1 | Viewed by 1633
Abstract
Atopic dermatitis (AD) or eczema is an important inflammatory chronic skin disease that brings many complications in its management and treatment. Although several chemical agents are used for treatment, the search for better anti-inflammatory and antibacterial agents of plant origin has been ongoing, [...] Read more.
Atopic dermatitis (AD) or eczema is an important inflammatory chronic skin disease that brings many complications in its management and treatment. Although several chemical agents are used for treatment, the search for better anti-inflammatory and antibacterial agents of plant origin has been ongoing, since natural compounds, it is commonly believed, are less dangerous than synthetic ones. Therefore, the present study explored a medicinal plant—Eclipta prostrata (L.) L.—for its anti-inflammatory activity alone and in combination with a non-steroidal anti-inflammatory drug (NSAID), diclofenac. The plant extract was used to make a cream formulation for treating atopic dermatitis and as an antibacterial agent against Staphylococcus aures, the major infectious agent associated with AD. The phytochemical analysis of the E. prostrata extract showed the presence of various phytochemicals, including flavonoids, Tannin, saponin, terpenoids, glycosides, phenol, alkaloids, quinone, and protein. The GC-MS profiling of methanolic E. prostrata extract was performed predicted the presence of twenty important phytochemicals, including 2-[5-(2-Hydroxypropyl) oxolan-2-yl]propanoic acid, dl-Menthol, dodecane, undecane, 4,7-dimethyl-, dodecane, 2,6,10-trimethyl-, decane, 2,3,5,8-tetramethyl-, cholest-5-en-3-ol, (3.alpha.)-, TMS derivative, cyclopropane carboxylic acid, 1-hydroxy-, (2,6-di-t-butyl-4-methylphenyl) ester, alpha.-farnesene, propanoic acid, 2-methyl-, 2-ethyl-1-propyl-1,3-propanediyl ester, diethyl phthalate, corticosterone, 2-methylpropionate, hentriacontan-13-ol, O-TMS, phthalic acid, 2,4-dimethylpent-3-yl dodecyl ester, hexasiloxane, 1,1,3,3,5,5,7,7,9,9,11,11-dodecamethyl-, acetic acid, 4-t-butyl-4-hydroxy-1,5-dimethyl-hex-2-ynyl ester, octadecane, 2-methyl- octacosane, 1-iodo-, nonacosane, and eicosyl isopropyl ether. Using an egg albumin denaturation inhibition assay, the anti-inflammatory activities of E. prostrata alone and in combination with diclofenac were investigated, and they showed 93% and 99% denaturation inhibition at 5 mg concentration of E. prostrata in alone and combination with diclofenac, respectively. Heat-induced haemolysis showed 2.5% and 2.4% of haemolysis at 5 mg of E. prostrata alone and in combination with diclofenac, respectively. An MTT assay performed using L929 cells proved that the extract has no cytotoxic effect. The plant extract displayed potential antibacterial activity against Staphylococcus aureus; the growth was inhibited at 1 mg/mL of E. prostrata extract. Thus, based on this evidence, the authors suggest that E. prostrata extract should be studied further for its anti-inflammatory and antibacterial activities and topical application in the treatment of atopic dermatitis. Full article
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13 pages, 1587 KiB  
Article
In Vitro Study of Antiviral Properties of Compounds Based on 1,4-Dioxane Derivative of Closo-Decaborate Anion with Amino Acid Ester Residues Against Influenza Virus A/IIV-Orenburg/83/2012(H1N1)pdm09
by Timur M. Garaev, Ilya I. Yudin, Natalya V. Breslav, Tatyana V. Grebennikova, Evgenii Y. Matveev, Elizaveta A. Eshtukova-Shcheglova, Varvara V. Avdeeva, Konstantin Y. Zhizhin and Nikolay T. Kuznetsov
Molecules 2024, 29(24), 5886; https://doi.org/10.3390/molecules29245886 - 13 Dec 2024
Cited by 1 | Viewed by 1128
Abstract
New derivatives of the closo-decaborate anion [B10H9–O(CH2)2O(CH2)3C(O)–L–OCH3]2− (An) (1: L = Trp; 2: L = His; 3: L = Met; 4: L [...] Read more.
New derivatives of the closo-decaborate anion [B10H9–O(CH2)2O(CH2)3C(O)–L–OCH3]2− (An) (1: L = Trp; 2: L = His; 3: L = Met; 4: L = Ala(2-oxopyrrolidin-3-yl) (Pld) were synthesized and isolated as tetraphenylphosphonium salts (Ph4P)2An. Anions 12−; 22−; 32−, and 42− contain a pendant functional group from the L-tryptophan methyl ester, L-histidine methyl ester, L-methionine methyl ester, or methyl 2-amino-3-(2-oxopyrrolidin-3-yl)propanoate (-Trp–OCH3, -His–OCH3, -Met–OCH3, or -Pld–OCH3) residue, respectively, bonded with the boron cluster anion through the oxybis[(ethane-2,1-diyl)oxy] spacer. This pacer is formed as a result of the nucleophilic opening of the attached dioxane molecule in the [B10H9O(CH2)4O] starting derivative. Sodium salts of the target compounds were isolated and used in biological experiments. It was established that among compounds Na2An (An = 14), not all are capable of inhibiting the cytopathic effect of the virus in vitro. Sodium salts Na2An have a low toxic effect on a monolayer of continuous canine embryonic kidney (MDCK) cell line. Compounds Na21 and Na22 had IC50 of 5.0 and 20.0 μg/mL, respectively, while for compounds Na23 and Na24, IC50 values could not be achieved at the concentrations studied. The studies performed for molecular docking of the anionic part of 12− and 22− with the transmembrane domain of viroporin M2 show some differences in the location of these two ligands inside the M2 canal pore. Full article
(This article belongs to the Section Bioorganic Chemistry)
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24 pages, 6883 KiB  
Article
Organic Moiety on Sn(IV) Does Matter for In Vitro Mode of Action: nBu3Sn(IV) Compounds with Carboxylato N-Functionalized 2-Quinolones Induce Anoikis-like Cell Death in A375 Cells
by Marijana P. Kasalović, Sanja Jelača, Dušan Dimić, Danijela Maksimović-Ivanić, Verica V. Jevtić, Sanja Mijatović, Tobias Rüffer, Goran N. Kaluđerović and Nebojša Đ. Pantelić
Pharmaceutics 2024, 16(12), 1529; https://doi.org/10.3390/pharmaceutics16121529 - 28 Nov 2024
Cited by 1 | Viewed by 1115
Abstract
Objectives: New tributyltin(IV) complexes containing the carboxylate ligands 3-(4-methyl-2-oxoquinolin-1(2H)-yl)propanoic acid (HL1) and 2-(4-methyl-2-oxoquinolin-1(2H)-yl)acetic acid (HL2) have been synthesized. Methods: Their structures have been determined by elemental microanalysis, FT-IR and multinuclear NMR (1H, 13C and 119Sn) [...] Read more.
Objectives: New tributyltin(IV) complexes containing the carboxylate ligands 3-(4-methyl-2-oxoquinolin-1(2H)-yl)propanoic acid (HL1) and 2-(4-methyl-2-oxoquinolin-1(2H)-yl)acetic acid (HL2) have been synthesized. Methods: Their structures have been determined by elemental microanalysis, FT-IR and multinuclear NMR (1H, 13C and 119Sn) spectroscopy and X-ray diffraction study. A solution state NMR analysis reveals a four-coordinated tributyltin(IV) complex in non-polar solvents, while an X-Ray crystallographic analysis confirms a five-coordinated trigonal-bipyramidal geometry around the tin atom due to the formation of 1D chains. A theoretical structural analysis was performed by optimization employing B3LYP-D3BJ functional and 6-311++G(d,p)/def2-TZVP(Sn) basis sets for H, C, N, O/Sn, respectively. The interactions between tin(IV) and surrounding atoms were examined by QTAIM approach. The in vitro antiproliferative activity of the synthesized compounds was evaluated by MTT and CV assays versus MCF-7 (human breast adenocarcinoma), HCT116 (human colorectal carcinoma), A375 (human melanoma), 4T1 (mouse breast carcinoma), CT26 (mouse colon carcinoma) and B16 (mouse melanoma) tumor cell lines. Results: Both synthesized compounds (nBu3SnL1 and nBu3SnL2) exerted powerful micromolar IC50 cytotoxicity values and demonstrated high selectivity toward malignant cells. Both experimental drugs affected cell adhesion and induced anchorage independent apoptosis, a favorable type of cell death with an essential role in cancer dissemination prevention. The BSA-binding affinity of the obtained organotin compounds was followed by spectrofluorometric titration and molecular docking simulations. Conclusions: The tributyltin(IV) compounds selectively induce anoikis-like cell death in A375 cells, also highlighting the importance of the organic moiety on the tin(IV) ion in the mechanism of action. Full article
(This article belongs to the Special Issue Pharmaceutical Applications of Metal Complexes and Derived Materials)
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18 pages, 5543 KiB  
Article
Characterization and Differentiation of Flavor Profile of 12 Air-Dried Yak Meat Products Using GC–IMS and Multivariate Analysis
by Qiuyu Wang, Rongsheng Du, Yuqi Wang, Shulin Zhang, Linlin Wang and Lina Wang
Foods 2024, 13(16), 2626; https://doi.org/10.3390/foods13162626 - 21 Aug 2024
Cited by 4 | Viewed by 1367
Abstract
Volatile organic compounds (VOCs) in food are key factors constituting their unique flavor, while the characteristics of VOCs in air-dried yak meat (AYM) from various regions of the Tibetan Plateau and their inter-regional differences remain unclear. Therefore, this study conducted a comprehensive analysis [...] Read more.
Volatile organic compounds (VOCs) in food are key factors constituting their unique flavor, while the characteristics of VOCs in air-dried yak meat (AYM) from various regions of the Tibetan Plateau and their inter-regional differences remain unclear. Therefore, this study conducted a comprehensive analysis of VOCs in the five-spice (FS), spicy and numbing (SN), and aromatic and spicy (AS) versions of AYM from four regions of the Tibetan Plateau (Gansu, Qinghai, Sichuan, and Tibet) using gas chromatography–ion mobility spectrometry (GC–IMS) A total of 58 VOCs were identified, with alcohols accounting for 28.40%, ketones 22.89%, aldehydes 18.85%, and terpenes 17.61%. Topographic plots, fingerprint profiles, and multivariate analysis not only distinguished AYM of the same flavor from different regions but also discriminated those of different flavors within the same region. Furthermore, 17 key VOCs were selected as the primary aroma characteristics of the 12 types of AYM, including linalool, 3-methylbutanal, acetone, and limonene. Meanwhile, the differential VOCs for each flavor were determined, with linalyl acetate being unique to the FS, (E)-ocimene and ethyl propanoate being specific to the SN, and 2-methyl-3-(methylthio)furan-D and Hexanal-D being characteristic of the AS flavor. Based on the above results, the flavor of AYM can be improved to suit the taste of most people and increase its consumption. Full article
(This article belongs to the Section Food Analytical Methods)
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14 pages, 1328 KiB  
Article
Effects of Drying Methods on the Antioxidant Properties of Piper betle Leaves
by Kivaandra Dayaa Rao Ramarao, Zuliana Razali, Chandran Somasundram, Wijenthiran Kunasekaran and Tan Li Jin
Molecules 2024, 29(8), 1762; https://doi.org/10.3390/molecules29081762 - 12 Apr 2024
Cited by 2 | Viewed by 3767
Abstract
Piper betle leaf powder is increasingly utilised as a health supplement. In this study, P. betle leaves were subjected to four different drying methods: convective air-drying, oven-drying, sun-drying, and no drying, with fresh leaves as control. Their antioxidant properties were then evaluated using [...] Read more.
Piper betle leaf powder is increasingly utilised as a health supplement. In this study, P. betle leaves were subjected to four different drying methods: convective air-drying, oven-drying, sun-drying, and no drying, with fresh leaves as control. Their antioxidant properties were then evaluated using colourimetric assays and GC-MS. Results showed that the sun-dried leaves had the highest (p < 0.05) total antioxidant capacity (66.23 ± 0.10 mg AAE/g), total polyphenol content (133.93 ± 3.76 mg GAE/g), total flavonoid content (81.25 ± 3.26 mg CE/g) and DPPH radical scavenging activity (56.48 ± 0.11%), and the lowest alkaloid content (45.684 ± 0.265 mg/gm). GC-MS analysis revealed that major constituents of aqueous extracts of fresh and sun-dried P. betle leaves were hydrazine 1,2-dimethyl-; ethyl aminomethylformimidate; glycerin; propanoic acid, 2-hydroxy-, methyl ester, (+/−)-; and 1,2-Cyclopentanedione. In conclusion, sun-dried leaves exhibited overall better antioxidant properties, and their aqueous extracts contained biologically active phytoconstituents that have uses in various fields. Full article
(This article belongs to the Special Issue Antioxidant Activity of Foods and Natural Products)
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12 pages, 1734 KiB  
Article
GC-MS with Headspace Extraction for Non-Invasive Diagnostics of IBD Dynamics in a Model of DSS-Induced Colitis in Rats
by Olga Yu. Shagaleeva, Daria A. Kashatnikova, Dmitry A. Kardonsky, Elena Yu. Danilova, Viktor A. Ivanov, Suleiman S. Evsiev, Eugene A. Zubkov, Olga V. Abramova, Yana A. Zorkina, Anna Y. Morozova, Dmitry N. Konanov, Artemiy S. Silantiev, Boris A. Efimov, Irina V. Kolesnikova, Julia A. Bespyatykh, Joanna Stimpson and Natalya B. Zakharzhevskaya
Int. J. Mol. Sci. 2024, 25(6), 3295; https://doi.org/10.3390/ijms25063295 - 14 Mar 2024
Cited by 1 | Viewed by 1826
Abstract
Inflammatory bowel diseases are extremely common throughout the world. However, in most cases, it is asymptomatic at the initial stage. Therefore, it is important to develop non-invasive diagnostic methods that allow identification of the IBD risks in a timely manner. It is well [...] Read more.
Inflammatory bowel diseases are extremely common throughout the world. However, in most cases, it is asymptomatic at the initial stage. Therefore, it is important to develop non-invasive diagnostic methods that allow identification of the IBD risks in a timely manner. It is well known that gastrointestinal microbiota secrete volatile compounds (VOCs) and their composition may change in IBD. We propose a non-invasive method to identify the dynamics of IBD development in the acute and remission stage at the level of VOCs in model of dextran sulfate sodium (DSS) with chemically induced colitis measured by headspace GC/MS (HS GC/MS). Methods: VOCs profile was identified using a headspace GC/MS (HS GC/MS). GC/MS data were processed using MetaboAnalyst 5.0 and GraphPad Prism 8.0.1 software. The disease activity index (DAI) and histological method were used to assess intestinal inflammation. The peak of intestinal inflammation activity was reached on day 7, according to the disease activity index. Histological examination data showed changes in the intestine due to different stages of inflammation. As the acute inflammation stage was reached, the metabolomic profile also underwent changes, especially at the short-fatty acids level. A higher relative amounts of acetic acid (p value < 0.025) and lower relative amounts of propanoic acid (p value < 0.0005), butanoic acid (p value < 0.005) and phenol 4-methyl- (p value = 0.053) were observed in DSS7 group on day 7 compared to the control group. In remission stage, disease activity indexes decreased, and the histological picture also improved. But metabolome changes continued despite the withdrawal of the DSS examination. A lower relative amounts of propanoic acid (p value < 0.025), butanoic acid (p value < 0.0005), pentanoic acid (p value < 0.0005), and a significant de-crease of hexanoic acid (p value < 0.0005) relative amounts were observed in the DSS14 group compared to the control group on day 14. A model of DSS-induced colitis in rats was successfully implemented for metabolomic assessment of different stages of inflammation. We demonstrated that the ratios of volatile compounds change in response to DSS before the appearance of standard signs of inflammation, determined by DAI and histological examination. Changes in the volatile metabolome persisted even after visual intestine repair and it confirms the high sensitivity of the microbiota to the damaging effects of DSS. The use of HS GC/MS may be an important addition to existing methods for assessing inflammation at early stages. Full article
(This article belongs to the Section Biochemistry)
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22 pages, 6612 KiB  
Article
Trimethyltin(IV) Bearing 3-(4-Methyl-2-oxoquinolin-1(2H)-yl)propanoate Causes Lipid Peroxidation-Mediated Autophagic Cell Death in Human Melanoma A375 Cells
by Marijana P. Kasalović, Dušan Dimić, Sanja Jelača, Danijela Maksimović-Ivanić, Sanja Mijatović, Bojana B. Zmejkovski, Simon H. F. Schreiner, Tobias Rüffer, Nebojša Đ. Pantelić and Goran N. Kaluđerović
Pharmaceuticals 2024, 17(3), 372; https://doi.org/10.3390/ph17030372 - 14 Mar 2024
Cited by 4 | Viewed by 2208
Abstract
A novel trimethyltin(IV) complex (Me3SnL), derived from 3-(4-methyl-2-oxoquinolin-1(2H)-yl)propanoate ligand, has been synthesized and characterized by elemental microanalysis, UV/Vis spectrophotometry, FT-IR and multinuclear (1H, 13C and 119Sn) NMR spectroscopies. Furthermore, the structure of the ligand precursor [...] Read more.
A novel trimethyltin(IV) complex (Me3SnL), derived from 3-(4-methyl-2-oxoquinolin-1(2H)-yl)propanoate ligand, has been synthesized and characterized by elemental microanalysis, UV/Vis spectrophotometry, FT-IR and multinuclear (1H, 13C and 119Sn) NMR spectroscopies. Furthermore, the structure of the ligand precursor HL was solved using SC-XRD (single-crystal X-ray diffraction). The prediction of UV/Vis and NMR spectra by quantum-chemical methods was performed and compared to experimental findings. The protein binding affinity of Me3SnL towards BSA was determined by spectrofluorometric titration and subsequent molecular docking simulations. Me3SnL has been evaluated for its in vitro anticancer activity against three human cell lines, MCF-7 (breast adenocarcinoma), A375 (melanoma) and HCT116 (colorectal carcinoma), and three mouse tumor cell lines, 4T1 (breast carcinoma), B16 (melanoma) and CT26 (colon carcinoma), using MTT and CV assays. The strong inhibition of A375 cell proliferation, ROS/RNS upregulation and robust lipid peroxidation lead to autophagic cell death upon treatment with Me3SnL. Full article
(This article belongs to the Special Issue Medicinal Metal Ions and Metal-Based Complex)
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13 pages, 1167 KiB  
Article
Electronic Nose and Gas Chromatograph Devices for the Evaluation of the Sensory Quality of Green Coffee Beans
by Gema Cascos, Jesús Lozano, Ismael Montero-Fernández, Jhunior Abrahan Marcía-Fuentes, Ricardo S. Aleman, Antonio Ruiz-Canales and Daniel Martín-Vertedor
Foods 2024, 13(1), 87; https://doi.org/10.3390/foods13010087 - 26 Dec 2023
Cited by 5 | Viewed by 2678
Abstract
The aim of this work is to discriminate between the volatile org9anic compound (VOC) characteristics of different qualities of green coffee beans (Coffea arabica) using two analysis approaches to classify the fresh product. High-quality coffee presented the highest values for positive [...] Read more.
The aim of this work is to discriminate between the volatile org9anic compound (VOC) characteristics of different qualities of green coffee beans (Coffea arabica) using two analysis approaches to classify the fresh product. High-quality coffee presented the highest values for positive attributes, the highest of which being fruity, herbal, and sweet. Low-quality samples showed negative attributes related to roasted, smoky, and abnormal fermentation. Alcohols and aromatic compounds were most abundant in the high-quality samples, while carboxylic acids, pyrazines, and pyridines were most abundant in the samples of low quality. The VOCs with positive attributes were phenylethyl alcohol, nonanal and 2-methyl-propanoic acid, and octyl ester, while those with negative attributes were pyridine, octanoic acid, and dimethyl sulfide. The aroma quality of fresh coffee beans was also discriminated using E-nose instruments. The PLS-DA model obtained from the E-nose data was able to classify the different qualities of green coffee beans and explained 96.9% of the total variance. A PLS chemometric approach was evaluated for quantifying the fruity aroma of the green coffee beans, obtaining an RP2 of 0.88. Thus, it can be concluded that the E-nose represents an accurate, inexpensive, and non-destructive device for discriminating between different coffee qualities during processing. Full article
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2 pages, 163 KiB  
Abstract
LC-MS-Based Metabolomics for Dietary Biomarker Discovery in a Cohort of Pregnant and Lactating Women and Their Infants
by Mia Stråvik, Olle Hartvigsson, Stefania Noerman, Anna Sandin, Agnes E. Wold, Malin Barman and Ann-Sofie Sandberg
Proceedings 2023, 91(1), 61; https://doi.org/10.3390/proceedings2023091061 - 20 Nov 2023
Viewed by 1032
Abstract
Circulating food metabolites could improve dietary assessment by complementing more traditional, subjective methods. However, information is lacking on the accuracy of these objective markers during pregnancy and lactation. The objective of this paper was to measure a panel of candidate food intake biomarkers, [...] Read more.
Circulating food metabolites could improve dietary assessment by complementing more traditional, subjective methods. However, information is lacking on the accuracy of these objective markers during pregnancy and lactation. The objective of this paper was to measure a panel of candidate food intake biomarkers, representing different food groups, during pregnancy, delivery, and lactation and correlate their plasma levels with self-reported food intake. All data was collected within the Swedish birth cohort Nutritional impact on Immunological maturation during Childhood in relation to the Environment (NICE). Plasma samples from the women (gestational week 29, N = 579; delivery, N = 532; and four months postpartum, N = 477) and their infants (delivery, N = 348; and four months, N = 193) were analyzed with untargeted liquid chromatography-mass spectrometry (LC-MS) based metabolomics. Food intake was assessed during pregnancy (gestational week 34) and lactation (one and four months postpartum) using a semi-quantitative food frequency questionnaire. Spearman correlation analyses with plasma levels and reported food intake were adjusted for multiple testing. Acetylcarnitine, choline, indole-3-lactic acid, lutein, pipecolic acid, proline betaine, and 3-carboxy-4-methyl-5-propyl-2-furan-propanoic acid (CMPF) were identified in plasma. Self-reported intake of fruit juice correlated positively with proline betaine during pregnancy (rho = 0.38, padj < 0.001), delivery (rho = 0.23, padj < 0.001), and postpartum (rho = 0.41, padj < 0.001), and also with infant plasma levels at delivery (rho = 0.25, padj < 0.001). Lutein correlated with vegetables in general, both during pregnancy (rho=0.31, padj<0.001) and delivery (rho = 0.29, padj < 0.001). CMPF in plasma from mothers and infants at four months correlated with maternal intake of fatty fish (mother: rho = 0.30, padj < 0.001; breastfed infant: rho = 0.26, padj = 0.037). No clear associations were obtained for the remaining metabolites. Our study confirms the use of proline betaine as a citrus fruit intake biomarker, primarily in the form of juice, for pregnant and lactating women. Plasma lutein could be useful as a more general fruit and vegetable intake biomarker during pregnancy, and CMPF as a fish intake biomarker during lactation. ClinicalTrials.gov identifier: NCT05809479 Full article
(This article belongs to the Proceedings of The 14th European Nutrition Conference FENS 2023)
16 pages, 8586 KiB  
Article
Flavor Quality Analysis of Ten Actinidia arguta Fruits Based on High-Performance Liquid Chromatography and Headspace Gas Chromatography–Ion Mobility Spectrometry
by Jinli Wen, Yue Wang, Yanli He, Nan Shu, Weiyu Cao, Yining Sun, Pengqiang Yuan, Bowei Sun, Yiping Yan, Hongyan Qin, Shutian Fan and Wenpeng Lu
Molecules 2023, 28(22), 7559; https://doi.org/10.3390/molecules28227559 - 13 Nov 2023
Cited by 9 | Viewed by 1727
Abstract
Actinidia arguta is a fruit crop with high nutritional and economic value. However, its flavor quality depends on various factors, such as variety, environment, and post-harvest handling. We analyzed the composition of total soluble sugars, titratable acids, organic acids, and flavor substances in [...] Read more.
Actinidia arguta is a fruit crop with high nutritional and economic value. However, its flavor quality depends on various factors, such as variety, environment, and post-harvest handling. We analyzed the composition of total soluble sugars, titratable acids, organic acids, and flavor substances in the fruits of ten A. arguta varieties. The total soluble sugar content ranged from 4.22 g/L to 12.99 g/L, the titratable acid content ranged from 52.55 g/L to 89.9 g/L, and the sugar–acid ratio ranged from 5.39 to 14.17 at the soft ripe stage. High-performance liquid chromatography (HPLC) showed that citric, quinic, and malic acids were the main organic acids in the A. arguta fruits. Headspace gas chromatography–ion mobility spectrometry (HS-GC-IMS) detected 81 volatile compounds in 10 A. arguta varieties, including 24 esters, 17 alcohols, 23 aldehydes, 7 ketones, 5 terpenes, 2 acids, 1 Pyrazine, 1 furan, and 1 benzene. Esters and aldehydes had the highest relative content of total volatile compounds. An orthogonal partial least squares discriminant analysis (OPLS-DA) based on the odor activity value (OAV) revealed that myrcene, benzaldehyde, methyl isobutyrate, α-phellandrene, 3-methyl butanal, valeraldehyde, ethyl butyrate, acetoin, (E)-2-octenal, hexyl propanoate, terpinolene, 1-penten-3-one, and methyl butyrate were the main contributors to the differences in the aroma profiles of the fruits of different A. arguta varieties. Ten A. arguta varieties have different flavors. This study can clarify the differences between varieties and provide a reference for the evaluation of A. arguta fruit flavor, variety improvement and new variety selection. Full article
(This article belongs to the Special Issue Yummy Chemistry: Volatile Compounds in Food Products)
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12 pages, 1949 KiB  
Article
Characterization of the Key Aroma Compounds in Different Yeast Proteins by GC-MS/O, Sensory Evaluation, and E-Nose
by Jiahui Chen, Dandan Pu, Yige Shi, Baoguo Sun, Hui Guo, Ku Li and Yuyu Zhang
Foods 2023, 12(16), 3136; https://doi.org/10.3390/foods12163136 - 21 Aug 2023
Cited by 9 | Viewed by 2684
Abstract
The unique odors of yeast proteins (YPs) are decisive for their application in meat substitutes. Sensory evaluation, electronic nose, and gas chromatography–mass spectrometry/olfactory (GC-MS/O) were combined to characterize the aroma profiles and aroma-active compounds of YPs. The sensory evaluation results indicate that the [...] Read more.
The unique odors of yeast proteins (YPs) are decisive for their application in meat substitutes. Sensory evaluation, electronic nose, and gas chromatography–mass spectrometry/olfactory (GC-MS/O) were combined to characterize the aroma profiles and aroma-active compounds of YPs. The sensory evaluation results indicate that the sweaty aroma had the strongest intensity in YP #10, followed by rice bran, sour, and plastic. The electronic nose could effectively distinguish the aroma differences among five YPs. A total of 27 aroma-active compounds in the five YPs were identified by GC-MS/O. The concentration of 2-methyl-propanoic acid (6.37 μg/kg), butanoic acid (47.46 μg/kg), 3-methyl-butanoic acid (22.50 μg/kg), and indole (943.40 μg/kg) in YP #10’s aroma was higher than that of the other YPs. The partial least squares regression method results show that o-cresol, (3S)-3,7-dimethyloct-7-en-1-ol, benzyl alcohol, octanal, 2-methyl-propanoic acid, butanoic acid, 3-methyl-butanoic acid, hexanal, heptanal, and indole were predicted as the potential aroma-active compounds significantly contributing to the aroma profiles of the five YPs. Addition experiments confirmed that the overall aroma profile intensities of the five YP samples were extended with the addition of these ten compounds, verifying their significant contributions. Full article
(This article belongs to the Section Meat)
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17 pages, 3527 KiB  
Article
Linking Colorimetric Variation with Non-Volatile and Volatile Components of Carob Flour
by Chrystalla Antoniou, Marios C. Kyriacou, Angelos C. Kyratzis and Youssef Rouphael
Foods 2023, 12(13), 2556; https://doi.org/10.3390/foods12132556 - 30 Jun 2023
Cited by 4 | Viewed by 1709
Abstract
Chromatic variation was examined for its association with flour composition and quality. Carob samples from variable altitudes and genetic backgrounds were milled and assessed for colorimetric parameter L* (lightness) and analyzed for phenols, tannins, antioxidant capacity, soluble carbohydrates (HPLC-RID), organic acids and protein [...] Read more.
Chromatic variation was examined for its association with flour composition and quality. Carob samples from variable altitudes and genetic backgrounds were milled and assessed for colorimetric parameter L* (lightness) and analyzed for phenols, tannins, antioxidant capacity, soluble carbohydrates (HPLC-RID), organic acids and protein (IC-CD), and volatile organic compounds (VOCs; HS-SPME/GC-MS). Higher altitudes and grafted genotypes yielded lighter-colored flours of higher antioxidant potential, phenols, tannins, sucrose, and malic acid concentrations. VOCs were mainly acids, esters, aldehydes, ketones, and alcohols. Acids were the most abundant and correlated negatively with L*, though correlation for many individual acids was non-significant, including 2-methyl-propanoic acid, widely considered the carob signature aroma (cheesy acidic buttery). The compositional and quality indexing potential of L* is more robust for grafted than non-grafted material, owing putatively to a narrower genetic basis. Antioxidant capacity and concentrations of phenolics, tannins and sucrose correlated positively with L*, indicating increased levels in carob flours sourced from grafted trees at higher altitudes. These flours also have a lower content of reducing sugars, the implication of which in the darkening of carob flour warrants further investigation. Overall, L* constitutes a reliable index for ranking carob flours for key compositional attributes and may be further reinforced by multiple-year data. Full article
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