Agnieszka Trela-Makowej - Academia.edu (original) (raw)
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Papers by Agnieszka Trela-Makowej
Scientific reports, Jun 4, 2024
Science of The Total Environment, Jan 31, 2024
Biomolecules
We have found 15 previously unknown compounds in seeds of lemon and other citrus species, such as... more We have found 15 previously unknown compounds in seeds of lemon and other citrus species, such as tangerine, grapefruit and pomelo. The structure of these compounds was characterized by HR–MS spectrometry, fluorescence spectroscopy and chemical synthesis. These compounds were predominantly long-chain (C20–C25), saturated acyl-Nω-methylserotonins with the main contribution of C22 and C24 homologues, usually accounting for about 40% and 30% of all acylserotonins, respectively. The other, previously undescribed, minor compounds were branched-chain acylserotonins, as well as normal-chain acylserotonins, recently found in baobab seed oil. Within the seed, acylserotonins were found nearly exclusively in the inner seed coat, where probably their biosynthesis proceeds. On the other hand, lemon seedlings contained only trace amounts of these compounds that were not found in adult leaves. The compounds identified in the present studies were shown to have antioxidant properties in vitro, using...
Metabolites
Here we present comparative data on the inhibition of lipid peroxidation by a variety of tocochro... more Here we present comparative data on the inhibition of lipid peroxidation by a variety of tocochromanols in liposomes. We also show for the first time the potential neuroprotective role of all the vitamin E homologues investigated on the neuronally differentiated human neuroblastoma SH-SY5Y cell line. α-Tocopherol had nearly no effect in the inhibition of lipid peroxidation, while β-, γ-, and δ-tocopherols inhibited the reaction completely when it was initiated in a lipid phase. Similar effects were observed for tocotrienol homologues. Moreover, in this respect plastochromanol-8 was as effective as β-, γ-, and δ-tocochromanols. When the prenyllipids were investigated in a 1,1-diphenyl-2-picrylhydrazyl (DPPH) test and incorporated into different lipid carriers, the radical oxidation was most pronounced in liposomes, followed by mixed micelles and the micellar system. When the reaction of tocochromanols was examined in niosomes, the oxidation was most pronounced for α-tocopherol and pl...
The effect of tocopherols, tocotrienols and plastochromanol-8 in the inhibition of lipid peroxida... more The effect of tocopherols, tocotrienols and plastochromanol-8 in the inhibition of lipid peroxidation of liposomes prepared from natural chloroplast lipids, initiated by both water-soluble and lipid soluble azo-compounds, has been studied. In the case of tocopherols, α-tocopherol showed nearly no effect in the inhibition of lipid peroxidation, while β-, γ- and δ-tocopherols inhibited the reaction completely when it was initiated by lipid-soluble AMVN. Similar effects were observed for tocotrienol homologues. In the investigated reaction plastochromanol-8 was as effective as β-, γ- and δ-tocochromanols. When peroxidation was initiated by water-soluble AIPH in liposomes, the order and extent of inhibition was similar to those of AMVN initiator. However, in this case, α-tocopherol and α-tocotrienol showed more pronounced inhibition. When the prenyllipids were investigated in DPPH test, when incorporated into soy lipid liposomes, mixed micelles and micelles, DPPH oxidation was most pron...
Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids, 2021
During analysis of components of baobab (Adansonia digitata) seed oil, several new fluorescent co... more During analysis of components of baobab (Adansonia digitata) seed oil, several new fluorescent compounds were detected in HPLC chromatograms that were not found previously in any seed oils investigated so far. After preparative isolation of these compounds, structural analysis by NMR spectroscopy, UHPLC-HR-MS, GC-FID and spectroscopic methods were applied and allowed identification of these substances as series of N-acylserotonins containing saturated C22 to C26 fatty acids with minor contribution of C27 to C30 homologues. The main component was N-lignocerylserotonin and the content of odd carbon-atom-number fatty acids was unusually high among the homologues. The suggested structure of the investigated compounds was additionally confirmed by their chemical synthesis. Synthetic N-acylserotonins showed pronounced inhibition of membrane lipid peroxidation of liposomes prepared from chloroplast lipids, especially when the peroxidation was initiated by a water-soluble azo-initiator, AIPH. Comparative studies of the reaction rate constants of the N-acylserotonins and tocopherols with a stable radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) in solvents of different polarity revealed that N-acylserotonins showed similar activity to δ-tocopherol in this respect. The described compounds have been not reported before either in plants or in animals. This indicates that we have identified a new class of plant lipids with antioxidant properties that could have promising pharmacological activities.
Colloids and Surfaces B: Biointerfaces
International Journal of Molecular Sciences, 2021
Plant prenyllipids, especially isoprenoid chromanols and quinols, are very efficient low-molecula... more Plant prenyllipids, especially isoprenoid chromanols and quinols, are very efficient low-molecular-weight lipophilic antioxidants, protecting membranes and storage lipids from reactive oxygen species (ROS). ROS are byproducts of aerobic metabolism that can damage cell components, they are also known to play a role in signaling. Plants are particularly prone to oxidative damage because oxygenic photosynthesis results in O2 formation in their green tissues. In addition, the photosynthetic electron transfer chain is an important source of ROS. Therefore, chloroplasts are the main site of ROS generation in plant cells during the light reactions of photosynthesis, and plastidic antioxidants are crucial to prevent oxidative stress, which occurs when plants are exposed to various types of stress factors, both biotic and abiotic. The increase in antioxidant content during stress acclimation is a common phenomenon. In the present review, we describe the mechanisms of ROS (singlet oxygen, sup...
Scientific reports, Jun 4, 2024
Science of The Total Environment, Jan 31, 2024
Biomolecules
We have found 15 previously unknown compounds in seeds of lemon and other citrus species, such as... more We have found 15 previously unknown compounds in seeds of lemon and other citrus species, such as tangerine, grapefruit and pomelo. The structure of these compounds was characterized by HR–MS spectrometry, fluorescence spectroscopy and chemical synthesis. These compounds were predominantly long-chain (C20–C25), saturated acyl-Nω-methylserotonins with the main contribution of C22 and C24 homologues, usually accounting for about 40% and 30% of all acylserotonins, respectively. The other, previously undescribed, minor compounds were branched-chain acylserotonins, as well as normal-chain acylserotonins, recently found in baobab seed oil. Within the seed, acylserotonins were found nearly exclusively in the inner seed coat, where probably their biosynthesis proceeds. On the other hand, lemon seedlings contained only trace amounts of these compounds that were not found in adult leaves. The compounds identified in the present studies were shown to have antioxidant properties in vitro, using...
Metabolites
Here we present comparative data on the inhibition of lipid peroxidation by a variety of tocochro... more Here we present comparative data on the inhibition of lipid peroxidation by a variety of tocochromanols in liposomes. We also show for the first time the potential neuroprotective role of all the vitamin E homologues investigated on the neuronally differentiated human neuroblastoma SH-SY5Y cell line. α-Tocopherol had nearly no effect in the inhibition of lipid peroxidation, while β-, γ-, and δ-tocopherols inhibited the reaction completely when it was initiated in a lipid phase. Similar effects were observed for tocotrienol homologues. Moreover, in this respect plastochromanol-8 was as effective as β-, γ-, and δ-tocochromanols. When the prenyllipids were investigated in a 1,1-diphenyl-2-picrylhydrazyl (DPPH) test and incorporated into different lipid carriers, the radical oxidation was most pronounced in liposomes, followed by mixed micelles and the micellar system. When the reaction of tocochromanols was examined in niosomes, the oxidation was most pronounced for α-tocopherol and pl...
The effect of tocopherols, tocotrienols and plastochromanol-8 in the inhibition of lipid peroxida... more The effect of tocopherols, tocotrienols and plastochromanol-8 in the inhibition of lipid peroxidation of liposomes prepared from natural chloroplast lipids, initiated by both water-soluble and lipid soluble azo-compounds, has been studied. In the case of tocopherols, α-tocopherol showed nearly no effect in the inhibition of lipid peroxidation, while β-, γ- and δ-tocopherols inhibited the reaction completely when it was initiated by lipid-soluble AMVN. Similar effects were observed for tocotrienol homologues. In the investigated reaction plastochromanol-8 was as effective as β-, γ- and δ-tocochromanols. When peroxidation was initiated by water-soluble AIPH in liposomes, the order and extent of inhibition was similar to those of AMVN initiator. However, in this case, α-tocopherol and α-tocotrienol showed more pronounced inhibition. When the prenyllipids were investigated in DPPH test, when incorporated into soy lipid liposomes, mixed micelles and micelles, DPPH oxidation was most pron...
Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids, 2021
During analysis of components of baobab (Adansonia digitata) seed oil, several new fluorescent co... more During analysis of components of baobab (Adansonia digitata) seed oil, several new fluorescent compounds were detected in HPLC chromatograms that were not found previously in any seed oils investigated so far. After preparative isolation of these compounds, structural analysis by NMR spectroscopy, UHPLC-HR-MS, GC-FID and spectroscopic methods were applied and allowed identification of these substances as series of N-acylserotonins containing saturated C22 to C26 fatty acids with minor contribution of C27 to C30 homologues. The main component was N-lignocerylserotonin and the content of odd carbon-atom-number fatty acids was unusually high among the homologues. The suggested structure of the investigated compounds was additionally confirmed by their chemical synthesis. Synthetic N-acylserotonins showed pronounced inhibition of membrane lipid peroxidation of liposomes prepared from chloroplast lipids, especially when the peroxidation was initiated by a water-soluble azo-initiator, AIPH. Comparative studies of the reaction rate constants of the N-acylserotonins and tocopherols with a stable radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) in solvents of different polarity revealed that N-acylserotonins showed similar activity to δ-tocopherol in this respect. The described compounds have been not reported before either in plants or in animals. This indicates that we have identified a new class of plant lipids with antioxidant properties that could have promising pharmacological activities.
Colloids and Surfaces B: Biointerfaces
International Journal of Molecular Sciences, 2021
Plant prenyllipids, especially isoprenoid chromanols and quinols, are very efficient low-molecula... more Plant prenyllipids, especially isoprenoid chromanols and quinols, are very efficient low-molecular-weight lipophilic antioxidants, protecting membranes and storage lipids from reactive oxygen species (ROS). ROS are byproducts of aerobic metabolism that can damage cell components, they are also known to play a role in signaling. Plants are particularly prone to oxidative damage because oxygenic photosynthesis results in O2 formation in their green tissues. In addition, the photosynthetic electron transfer chain is an important source of ROS. Therefore, chloroplasts are the main site of ROS generation in plant cells during the light reactions of photosynthesis, and plastidic antioxidants are crucial to prevent oxidative stress, which occurs when plants are exposed to various types of stress factors, both biotic and abiotic. The increase in antioxidant content during stress acclimation is a common phenomenon. In the present review, we describe the mechanisms of ROS (singlet oxygen, sup...