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Keywords = Δ1-pyrroline

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21 pages, 3939 KiB  
Article
The Proline Dehydrogenase Gene CsProDH1 Regulates Homeostasis of the Pro-P5C Cycle Under Drought Stress in Tea Plants
by Deng Deng, Qinqin Gao, Rou Zeng, Jie Jiang, Qiang Shen, Yuanchun Ma, Wanping Fang and Xujun Zhu
Int. J. Mol. Sci. 2025, 26(7), 3121; https://doi.org/10.3390/ijms26073121 - 28 Mar 2025
Viewed by 615
Abstract
The homeostasis of the proline-Δ1-pyrroline-5-carboxylate (Pro-P5C) cycle, mediated by proline dehydrogenase (ProDH), plays a critical role in plants in response to abiotic stresses. The biological function of gene CsProDH1 under drought stress and its effects on amino acid metabolism and photosynthesis [...] Read more.
The homeostasis of the proline-Δ1-pyrroline-5-carboxylate (Pro-P5C) cycle, mediated by proline dehydrogenase (ProDH), plays a critical role in plants in response to abiotic stresses. The biological function of gene CsProDH1 under drought stress and its effects on amino acid metabolism and photosynthesis through proline metabolism were investigated. Enzymatic characterization of the CsProDH1 protein was conducted in vitro. Overexpression of CsProDH1 aggravated plant stress, as evident by reduced photosynthetic efficiency and increased reactive oxygen species, which activated the Pro-P5C cycle. In contrast, silencing CsProDH1 enhanced plant drought resistance, increased proline accumulation, and protected photosynthesis. Studies indicate that exogenous amino acid application mitigates drought-induced physiological impairments in plants by maintaining cellular homeostasis, with particular efficacy observed in enhancing tea plant drought resilience through improved osmotic adjustment and antioxidant capacity. This study uncovers the significant role of CsProDH1 in plant drought resistance and its regulatory mechanism, offering potential gene targets and application strategies for enhancing crop drought resistance. Full article
(This article belongs to the Special Issue Molecular Insights and Regulation Mechanisms of Tea Quality)
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19 pages, 3457 KiB  
Article
Cross-Stressful Adaptation to Drought and High Salinity Is Related to Variable Antioxidant Defense, Proline Metabolism, and Dehydrin b Expression in White Clover
by Yao Ling, Duo Wang, Yan Peng, Dandan Peng and Zhou Li
Agronomy 2025, 15(1), 126; https://doi.org/10.3390/agronomy15010126 - 7 Jan 2025
Cited by 1 | Viewed by 1091
Abstract
A previous exposure to drought priming (DP) or salt priming (SP) could significantly improve future tolerance to both the same and different abiotic stresses, which is an effective mitigation strategy for plants to adapt to changing environmental conditions. If the type of stress [...] Read more.
A previous exposure to drought priming (DP) or salt priming (SP) could significantly improve future tolerance to both the same and different abiotic stresses, which is an effective mitigation strategy for plants to adapt to changing environmental conditions. If the type of stress priming is different from subsequent abiotic stress, this indicates that plants are trained to acquire cross tolerance. The objective of this study was to explore DP-regulated cross tolerance to salt stress and SP-induced cross tolerance to drought associated with changes in growth, antioxidant defense, proline metabolism, and the expression of the dehydration-responsive gene Dehydrin b involved in the stabilization of membrane systems, cryoprotection of intracellular proteins, and enhancement in water retention capacity in white clover (Trifolium repens). Plants were pretreated by initial DP or SP and then subjected to subsequent salt stress or drought stress for 10 days, respectively. The results demonstrated that DP significantly increased number of roots during subsequent salt stress, whereas SP significantly improved stem length, root length, and number of roots under drought stress, which indicated that the SP exhibited more pronounced and positive effects on mitigating subsequent drought-induced growth retardant. Both salt stress and drought resulted in significant increases in electrolyte leakage and contents of superoxide anion, hydrogen peroxide, and malonaldehyde due to reduced superoxide dismutase, peroxide, and catalase, as well as key enzyme activities in the ascorbate–glutathione cycle. SP or DP could significantly enhance these enzyme activities to alleviate subsequent drought- or salt-induced oxidative damage. SP or DP also significantly improved the accumulation of proline contributing to better water homeostasis by promoting biosynthetic enzyme activities (Δ1-pyrroline-5-carboxylate synthetase and aminotransferase) and restricting proline dehydrogenase activity for proline degradation under drought or salt stress, respectively. In addition, SP significantly up-regulated the expression of dehydrin b under drought stress, but DP failed to induce the expression of dehydrin b in response to subsequent salt stress. The current findings proved that the pre-exposure of white clover plants to DP or SP could effectively mitigate the negative effects of subsequent salt stress or drought related to some common and different pathways. Plants pretreated by initial DP or SP exhibited better adaption to subsequent different stress by regulating growth, physiological, metabolic, and transcriptional changes. Full article
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15 pages, 1852 KiB  
Article
Rice–Potato Rotation Pattern Affects 2-Acetyl-1-Pyrroline Biosynthesis and Productivity in Aromatic Rice Grains
by Fengqin Hu, Congcong Shen, Dehao Feng, Shuangbing Zhu, Jian Lu, Jianqiang Zhu, Xianjin Qiu, Kai Chen, Bin Du and Jianlong Xu
Agronomy 2025, 15(1), 97; https://doi.org/10.3390/agronomy15010097 - 1 Jan 2025
Viewed by 1201
Abstract
Aromatic rice has gained significant attention due to its high economic and nutritional value. 2-Acetyl-1-pyrroline (2-AP), a key aroma compound in aromatic rice, plays a crucial role in elucidating the aroma characteristics of aromatic rice. However, there is no report on the effect [...] Read more.
Aromatic rice has gained significant attention due to its high economic and nutritional value. 2-Acetyl-1-pyrroline (2-AP), a key aroma compound in aromatic rice, plays a crucial role in elucidating the aroma characteristics of aromatic rice. However, there is no report on the effect of aromatic rice in rice–potato rotation on aroma characteristics. In order to study the influences of winter-planted potatoes on the yield, quality, and 2-AP biosynthesis of aromatic rice grains, the commonly cultivated aromatic rice variety Meixiangzhan-2 and the potato cultivar Huashu-5 were selected as experimental materials for a three-year consecutive field experiment with different tillage patterns consisting of rice–winter fallow as the control group (CK) and rice–potato rotation as the experimental group (RP). The results indicated that the RP treatment enhanced the soil nutrient content and decreased the bulk density. Compared with CK, RP treatment increased the effective panicle number by 10.88% and grain number per panicle by 8.82%, thereby increasing the yield by 11.99%. Meanwhile, RP treatment improved the brown rice rate by 2.61%, milled rice rate by 4.53%, head milled rice rate by 7.51%, and crude protein content by 6.98%. Regarding 2-AP biosynthesis in grains, in contrast to CK, the RP treatment raised the levels of related precursors (Δ1-pyrroline, Δ1-pyrrolidine-5-carboxylic acid, and proline increased by 8.95%, 18.14%, and 13.75%, respectively) and enzymes (proline dehydrogenase, ornithine transaminase, and diamine oxidase increased by 18.37%, 14.61%, and 11.36%, respectively) in its synthesis pathway, thereby facilitating the accumulation of 2-AP. Furthermore, we also observed a more stable yield and grain 2-AP content in aromatic rice under RP treatment. Overall, with regard to enhancing the aromatic rice yield and aroma, the rice–potato rotation system can be contemplated for vigorous promotion. Full article
(This article belongs to the Section Innovative Cropping Systems)
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18 pages, 2360 KiB  
Article
Effects of Melatonin Pre- and Post-Drought Treatment on Oxidative Stress Markers and Expression of Proline-Related Transcripts in Young Wheat Plants
by Zornitsa Katerova, Dessislava Todorova, Irina I. Vaseva, Elena Shopova, Margarita Petrakova, Martin Iliev and Iskren Sergiev
Int. J. Mol. Sci. 2024, 25(22), 12127; https://doi.org/10.3390/ijms252212127 - 12 Nov 2024
Cited by 2 | Viewed by 1091
Abstract
Wheat can tolerate a mild water deficit, but prolonged drought causes a number of detrimental physiological changes resulting in a substantial decrease in productivity. The present study evaluates the potential of the natural plant growth regulator melatonin to alleviate the negative effects of [...] Read more.
Wheat can tolerate a mild water deficit, but prolonged drought causes a number of detrimental physiological changes resulting in a substantial decrease in productivity. The present study evaluates the potential of the natural plant growth regulator melatonin to alleviate the negative effects of moderate drought in two Bulgarian winter wheat cultivars at the early vegetative stage. Melatonin doses of 75 µM were root-supplemented 24 h before or after the stress period. The levels of several biometric parameters, osmolyte content and stress indicators as well as the expression of genes coding for key enzymes of the proline biosynthesis pathway were analyzed in leaves at the end of the drought stress and after two and four days of recovery. Applied alone, melatonin did not exert significant effects on most of the monitored parameters. Water deprivation negatively affected seedlings’ fresh weight and water content and increased the stress markers and osmolyte levels. These were accompanied by a high accumulation of TaP5CS and TaP5CR transcripts coding for the enzymes Δ-pyrroline-5-carboxylate synthase and Δ-pyrroline-5-carboxylate reductase, respectively. The effect of melatonin in reducing drought stress was similar whether applied before or after exposure, though slightly more effective when used as a pre-treatment. Full article
(This article belongs to the Special Issue Recent Research in Plant Abiotic Stress)
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24 pages, 6486 KiB  
Article
Unexpected Course of Reaction Between (1E,3E)-1,4-Dinitro-1,3-butadiene and N-Methyl Azomethine Ylide—A Comprehensive Experimental and Quantum-Chemical Study
by Mikołaj Sadowski and Karolina Kula
Molecules 2024, 29(21), 5066; https://doi.org/10.3390/molecules29215066 - 26 Oct 2024
Cited by 17 | Viewed by 1974
Abstract
In recent times, interest in the chemistry of conjugated nitrodienes is still significantly increasing. In particular, the application of these compounds as building blocks to obtain heterocycles is a popular object of research. Therefore, in continuation of our research devoted to the topic [...] Read more.
In recent times, interest in the chemistry of conjugated nitrodienes is still significantly increasing. In particular, the application of these compounds as building blocks to obtain heterocycles is a popular object of research. Therefore, in continuation of our research devoted to the topic of conjugated nitrodienes, experimental and quantum-chemical studies of a cycloaddition reaction between (1E,3E)-1,4-dinitro-1,3-butadiene and N-methyl azomethine ylide have been investigated. The computational results present that the tested reaction is realized through a pdr-type polar mechanism. In turn, the experimental study shows that in a course of this cycloaddition, only one reaction product in the form of 1-methyl-3-(trans-2-nitrovinyl)-Δ3-pyrroline is created. The constitution of this compound has been confirmed via spectroscopic methods. Finally, ADME analysis indicated that the synthesized Δ3-pyrroline exhibits biological potential, and it is a good drug candidate according to Lipinski, Veber and Egan rules. Nevertheless, PASS simulation showed that the compound exhibits weak antimicrobial, inhibitory and antagonist properties. Preliminary in silico research shows that although the obtained Δ3-pyrroline is not a good candidate for a drug, the presence of a nitrovinyl moiety in its structure indicates that the compound is an initial basis for further modifications. Full article
(This article belongs to the Special Issue Heterocyclic Compounds: Synthesis, Application and Theoretical Study)
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20 pages, 18707 KiB  
Article
Salicylic Acid and Melatonin Synergy Enhances Boron Toxicity Tolerance via AsA–GSH Cycle and Glyoxalase System Regulation in Fragrant Rice
by Muhammad Imran, Emilie Widemann, Sarfraz Shafiq, Ali Bakhsh, Xiaoyuan Chen and Xiangru Tang
Metabolites 2024, 14(10), 520; https://doi.org/10.3390/metabo14100520 - 26 Sep 2024
Cited by 2 | Viewed by 1381
Abstract
Background: Boron is an essential micronutrient for plant growth and productivity, yet excessive boron leads to toxicity, posing significant challenges for agriculture. Fragrant rice is popular among consumers, but the impact of boron toxicity on qualitative traits of fragrant rice, especially aroma, remains [...] Read more.
Background: Boron is an essential micronutrient for plant growth and productivity, yet excessive boron leads to toxicity, posing significant challenges for agriculture. Fragrant rice is popular among consumers, but the impact of boron toxicity on qualitative traits of fragrant rice, especially aroma, remains largely unexplored. The individual potentials of melatonin and salicylic acid in reducing boron toxicity are less known, while their synergistic effects and mechanisms in fragrant rice remain unclear. Methods: Thus, this study investigates the combined application of melatonin and salicylic acid on fragrant rice affected by boron toxicity. One-week-old seedlings were subjected to boron (0 and 800 µM) and then treated with melatonin and salicylic acid (0 and 100 µM, for 3 weeks). Results: Boron toxicity significantly impaired photosynthetic pigments, plant growth, and chloroplast integrity while increasing oxidative stress markers such as hydrogen peroxide, malondialdehyde, methylglyoxal, and betaine aldehyde dehydrogenase. Likewise, boron toxicity abridged the precursors involved in the 2-acetyl-1-pyrroline (2-AP) biosynthesis pathway. However, individual as well as combined application of melatonin and salicylic acid ameliorated boron toxicity by strengthening the antioxidant defense mechanisms—including the enzymes involved during the ascorbate–glutathione (AsA–GSH) cycle and glyoxalase system—and substantially improved 2-AP precursors including proline, P5C, Δ1-pyrroline, and GABA levels, thereby restoring the 2-AP content and aroma. These findings deduce that melatonin and salicylic acid synergistically alleviate boron toxicity-induced disruptions on the 2-AP biosynthesis pathway by improving the 2-AP precursors and enzymatic activities, as well as modulating the physio-biochemical processes and antioxidant defense system of fragrant rice plants. Conclusions: The findings of this study have the potential to enhance rice productivity and stress tolerance, offering solutions to improve food security and sustainability in agricultural practices, particularly in regions affected by environmental stressors. Full article
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18 pages, 4334 KiB  
Article
Ascorbic Acid Improves Tomato Salt Tolerance by Regulating Ion Homeostasis and Proline Synthesis
by Xianjun Chen, Hongwei Han, Yundan Cong, Xuezhen Li, Wenbo Zhang, Jinxia Cui, Wei Xu, Shengqun Pang and Huiying Liu
Plants 2024, 13(12), 1672; https://doi.org/10.3390/plants13121672 - 17 Jun 2024
Cited by 7 | Viewed by 1900
Abstract
In this study, processing tomato (Solanum lycopersicum L.) ‘Ligeer 87-5’ was hydroponically cultivated under 100 mM NaCl to simulate salt stress. To investigate the impacts on ion homeostasis, osmotic regulation, and redox status in tomato seedlings, different endogenous levels of ascorbic acid [...] Read more.
In this study, processing tomato (Solanum lycopersicum L.) ‘Ligeer 87-5’ was hydroponically cultivated under 100 mM NaCl to simulate salt stress. To investigate the impacts on ion homeostasis, osmotic regulation, and redox status in tomato seedlings, different endogenous levels of ascorbic acid (AsA) were established through the foliar application of 0.5 mM AsA (NA treatment), 0.25 mM lycorine (LYC, an inhibitor of AsA synthesis; NL treatment), and a combination of LYC and AsA (NLA treatment). The results demonstrated that exogenous AsA significantly increased the activities and gene expressions of key enzymes (L-galactono-1,4-lactone dehydrogenase (GalLDH) and L-galactose dehydrogenase (GalDH)) involved in AsA synthesis in tomato seedling leaves under NaCl stress and NL treatment, thereby increasing cellular AsA content to maintain its redox status in a reduced state. Additionally, exogenous AsA regulated multiple ion transporters via the SOS pathway and increased the selective absorption of K+, Ca2+, and Mg2+ in the aerial parts, reconstructing ion homeostasis in cells, thereby alleviating ion imbalance caused by salt stress. Exogenous AsA also increased proline dehydrogenase (ProDH) activity and gene expression, while inhibiting the activity and transcription levels of Δ1-pyrroline-5-carboxylate synthetase (P5CS) and ornithine-δ-aminotransferase (OAT), thereby reducing excessive proline content in the leaves and alleviating osmotic stress. LYC exacerbated ion imbalance and osmotic stress caused by salt stress, which could be significantly reversed by AsA application. Therefore, exogenous AsA application increased endogenous AsA levels, reestablished ion homeostasis, maintained osmotic balance, effectively alleviated the inhibitory effect of salt stress on tomato seedling growth, and enhanced their salt tolerance. Full article
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17 pages, 2717 KiB  
Article
Proline Metabolism in Response to Climate Extremes in Hairgrass
by Qiaoyu Luo, Yonggui Ma, Huichun Xie, Feifei Chang, Chiming Guan, Bing Yang and Yushou Ma
Plants 2024, 13(10), 1408; https://doi.org/10.3390/plants13101408 - 18 May 2024
Cited by 4 | Viewed by 1374
Abstract
Hairgrass (Deschampsia caespitosa), a widely distributed grass species considered promising in the ecological restoration of degraded grassland in the Qinghai-Xizang Plateau, is likely to be subjected to frequent drought and waterlogging stress due to ongoing climate change, further aggravating the degradation [...] Read more.
Hairgrass (Deschampsia caespitosa), a widely distributed grass species considered promising in the ecological restoration of degraded grassland in the Qinghai-Xizang Plateau, is likely to be subjected to frequent drought and waterlogging stress due to ongoing climate change, further aggravating the degradation of grassland in this region. However, whether it would acclimate to water stresses resulting from extreme climates remains unknown. Proline accumulation is a crucial metabolic response of plants to challenging environmental conditions. This study aims to investigate the changes in proline accumulation and key enzymes in hairgrass shoot and root tissues in response to distinct climate extremes including moderate drought, moderate waterlogging, and dry–wet variations over 28 days using a completely randomized block design. The proline accumulation, contribution of the glutamate and ornithine pathways, and key enzyme activities related to proline metabolism in shoot and root tissues were examined. The results showed that water stress led to proline accumulation in both shoot and root tissues of hairgrass, highlighting the importance of this osmoprotectant in mitigating the effects of environmental challenges. The differential accumulation of proline in shoots compared to roots suggests a strategic allocation of resources by the plant to cope with osmotic stress. Enzymatic activities related to proline metabolism, such as Δ1-pyrroline-5-carboxylate synthetase, ornithine aminotransferase, Δ1-pyrroline-5-carboxylate reductase, Δ1-pyrroline-5-carboxylate dehydrogenase, and proline dehydrogenase, further emphasize the dynamic regulation of proline levels in hairgrass under water stress conditions. These findings support the potential for enhancing the stress resistance of hairgrass through the genetic manipulation of proline biosynthesis and catabolism pathways. Full article
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20 pages, 4473 KiB  
Article
How Do Molecular Tweezers Bind to Proteins? Lessons from X-ray Crystallography
by Arthur T. Porfetye, Patricia Stege, Rocio Rebollido-Rios, Daniel Hoffmann, Thomas Schrader and Ingrid R. Vetter
Molecules 2024, 29(8), 1764; https://doi.org/10.3390/molecules29081764 - 12 Apr 2024
Cited by 2 | Viewed by 1944
Abstract
To understand the biological relevance and mode of action of artificial protein ligands, crystal structures with their protein targets are essential. Here, we describe and investigate all known crystal structures that contain a so-called “molecular tweezer” or one of its derivatives with an [...] Read more.
To understand the biological relevance and mode of action of artificial protein ligands, crystal structures with their protein targets are essential. Here, we describe and investigate all known crystal structures that contain a so-called “molecular tweezer” or one of its derivatives with an attached natural ligand on the respective target protein. The aromatic ring system of these compounds is able to include lysine and arginine side chains, supported by one or two phosphate groups that are attached to the half-moon-shaped molecule. Due to their marked preference for basic amino acids and the fully reversible binding mode, molecular tweezers are able to counteract pathologic protein aggregation and are currently being developed as disease-modifying therapies against neurodegenerative diseases such as Alzheimer’s and Parkinson’s disease. We analyzed the corresponding crystal structures with 14-3-3 proteins in complex with mono- and diphosphate tweezers. Furthermore, we solved crystal structures of two different tweezer variants in complex with the enzyme Δ1-Pyrroline-5-carboxyl-dehydrogenase (P5CDH) and found that the tweezers are bound to a lysine and methionine side chain, respectively. The different binding modes and their implications for affinity and specificity are discussed, as well as the general problems in crystallizing protein complexes with artificial ligands. Full article
(This article belongs to the Section Bioorganic Chemistry)
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17 pages, 3895 KiB  
Article
ChaWRKY40 Enhances Drought Tolerance of ‘Dawei’ Hazelnuts by Positively Regulating Proline Synthesis
by Pengfei Zhang, Ruiqiang Chao, Liping Qiu, Wenjing Ge, Jinjun Liang and Pengfei Wen
Forests 2024, 15(3), 407; https://doi.org/10.3390/f15030407 - 21 Feb 2024
Cited by 3 | Viewed by 1830
Abstract
Hazelnuts are among the most important nuts worldwide. Drought has severely restricted the development of the hazelnut industry in the wake of global warming and lack of water resources. Δ-1-pyrroline-5-carboxylic acid synthase (P5CS) is closely related to drought stress as the rate-limiting enzyme [...] Read more.
Hazelnuts are among the most important nuts worldwide. Drought has severely restricted the development of the hazelnut industry in the wake of global warming and lack of water resources. Δ-1-pyrroline-5-carboxylic acid synthase (P5CS) is closely related to drought stress as the rate-limiting enzyme of proline synthesis. WRKY40 had been proven to be an important transcription factor regulating drought tolerance in several plants. In this study, the hybrid hazelnut ‘Dawei’ exhibiting drought tolerance was used as the test material. Tests for simulated drought stress and ChaWRKY40 overexpression, and the yeast one-hybrid assay were performed. The results showed that the relative water content of leaves gradually decreased, but the proline content, electrolyte leakage, and expression of ChaWRKY40 and ChaP5CS increased with increasing PEG-6000 concentration in the leaves. A transient ChaWRKY40 overexpression trial indicated that overexpression of ChaWRKY40 improved the proline content and the transcription level of ChaP5CS. The Y1H experiment suggested that ChaWRKY40 directly binds to the W-box-acting element (W-box) on the promoter of ChaP5CS. In conclusion, ChaWRKY40 may increase the proline content by positively regulating the expression of the ChaP5CS gene, thereby improving the drought resistance of hazelnuts. Full article
(This article belongs to the Special Issue Advances in Hazelnut Germplasm and Genetic Improvement)
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19 pages, 4390 KiB  
Article
Proline Metabolism in WHO G4 Gliomas Is Altered as Compared to Unaffected Brain Tissue
by Magdalena M. Sawicka, Karol Sawicki, Marek Jadeszko, Katarzyna Bielawska, Elżbieta Supruniuk, Joanna Reszeć, Izabela Prokop-Bielenia, Barbara Polityńska, Mateusz Jadeszko, Magdalena Rybaczek, Eryk Latoch, Krzysztof Gorbacz, Tomasz Łysoń and Wojciech Miltyk
Cancers 2024, 16(2), 456; https://doi.org/10.3390/cancers16020456 - 21 Jan 2024
Cited by 3 | Viewed by 2408
Abstract
Proline metabolism has been identified as a significant player in several neoplasms, but knowledge of its role in gliomas is limited despite it providing a promising line of pursuit. Data on proline metabolism in the brain are somewhat historical. This study aims to [...] Read more.
Proline metabolism has been identified as a significant player in several neoplasms, but knowledge of its role in gliomas is limited despite it providing a promising line of pursuit. Data on proline metabolism in the brain are somewhat historical. This study aims to investigate alterations of proline metabolism in gliomas of WHO grade 4 (GG4) in the context of the brain. A total of 20 pairs of samples were studied, consisting of excised tumor and unaffected brain tissue, obtained when partial brain resection was required to reach deep-seated lesions. Levels of proline oxidase/proline dehydrogenase (POX/PRODH), Δ1-pyrroline-5-carboxylate reductases (PYCR1/2/3), prolidase (PEPD), and metalloproteinases (MMP-2, MMP-9) were assessed, along with the concentration of proline and proline-related metabolites. In comparison to normal brain tissue, POX/PRODH expression in GG4 was found to be suppressed, while PYCR1 expression and activity of PEPD, MMP-2, and -9 were upregulated. The GG4 proline concentration was 358% higher. Hence, rewiring of the proline metabolism in GG4 was confirmed for the first time, with a low-POX/PRODH/high-PYCR profile. High PEPD and MMPs activity is in keeping with GG4-increased collagen turnover and local aggressiveness. Further studies on the mechanisms of the interplay between altered proline metabolism and the GG4 microenvironment are warranted. Full article
(This article belongs to the Special Issue Novel Insights into Glioblastoma and Brain Metastases)
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13 pages, 2620 KiB  
Article
A Simple Entry to the 5,8-Disubstituted Indolizidine Skeleton via Hetero Diels-Alder Reaction
by Juan Francisco Rodríguez-Caro, María M. Afonso and José Antonio Palenzuela
Molecules 2023, 28(21), 7316; https://doi.org/10.3390/molecules28217316 - 28 Oct 2023
Viewed by 1924
Abstract
The 5,8-disubstituted indolizidines are the largest family of indolizidines isolated from the skin of amphibians. These compounds exhibit interesting biological activities such as noncompetitive blockers of nicotinic receptors. In this paper, we present a short, simple, and general synthesis of these alkaloids based [...] Read more.
The 5,8-disubstituted indolizidines are the largest family of indolizidines isolated from the skin of amphibians. These compounds exhibit interesting biological activities such as noncompetitive blockers of nicotinic receptors. In this paper, we present a short, simple, and general synthesis of these alkaloids based on the hetero Diels–Alder reaction between suitable monoactivated dienes and Δ1-pyrroline as the dienophile. The selectivity of the process is explained based on computational studies. Concise synthesis of the indolizidine alkaloid 181B from a hetero Diels–Alder reaction was accomplished in four steps. Full article
(This article belongs to the Section Organic Chemistry)
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19 pages, 4429 KiB  
Article
Proline Metabolism Process and Antioxidant Potential of Lycium ruthenicum Murr. in Response to NaCl Treatments
by Richard John Tiika, Huirong Duan, Hongshan Yang, Guangxin Cui, Fuping Tian, Yongtao He, Yanjun Ma and Yi Li
Int. J. Mol. Sci. 2023, 24(18), 13794; https://doi.org/10.3390/ijms241813794 - 7 Sep 2023
Cited by 6 | Viewed by 1728
Abstract
Salinity influences the level of antioxidants and proline content, which are both involved in the regulation of stress responses in plants. To examine the interplay between the antioxidant system and proline metabolism in plant stress acclimation, explants of Lycium ruthenicum were subjected to [...] Read more.
Salinity influences the level of antioxidants and proline content, which are both involved in the regulation of stress responses in plants. To examine the interplay between the antioxidant system and proline metabolism in plant stress acclimation, explants of Lycium ruthenicum were subjected to NaCl treatments, and the growth characteristics, antioxidant enzyme activities, proline accumulation, and metabolic enzyme content were analyzed. The results revealed that NaCl concentrations between 50 to 150 mM have a positive effect on the growth of L. ruthenicum explants. Increasing NaCl concentrations elevated the activities of superoxide dismutase (SOD) and catalase (CAT), while hydrogen peroxide (H2O2) content was inhibited, suggesting that the elevated antioxidants play a central protective role in superoxide anion (O2•−) and H2O2 scavenging processes in response to NaCl treatments. Also, high proline levels also protect antioxidant enzyme machinery, thus protecting the plants from oxidative damage and enhancing osmotic adjustment. Increasing levels of pyrroline-5-carboxylate synthetase (P5CS), pyrroline-5-carboxylate reductase (P5CR), and ornithine-δ-aminotransferase (δ-OAT) were observed, resulting in elevated level of proline. In addition, the expression levels of LrP5CS1, -2, -3, LrOAT-1, and -2 were promoted in NaCl treatments. According to the combined analysis of metabolic enzyme activities and their relative expression, it is confirmed that the glutamate (Glu) pathway is activated in L. ruthenicum faced with different levels of NaCl concentrations. However, Glu supplied by δ-OAT is fed back into the main pathway for proline metabolism. Full article
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23 pages, 3580 KiB  
Article
The Knockdown of AUXIN RESPONSE FACTOR 2 Confers Enhanced Tolerance to Salt and Drought Stresses in Tomato (Solanum lycopersicum L.)
by Ibtihaj El Mamoun, Sarah Bouzroud, Mohamed Zouine and Abdelaziz Smouni
Plants 2023, 12(15), 2804; https://doi.org/10.3390/plants12152804 - 28 Jul 2023
Cited by 13 | Viewed by 2261
Abstract
Auxin response factors (ARFs) act as key elements of the auxin-signaling pathway and play important roles in the process of a plant’s growth, development, and response to environmental conditions. We studied the implication of the SlARF2 gene in the tomato response [...] Read more.
Auxin response factors (ARFs) act as key elements of the auxin-signaling pathway and play important roles in the process of a plant’s growth, development, and response to environmental conditions. We studied the implication of the SlARF2 gene in the tomato response to salt (150 mM of NaCl) and drought (15% PEG 20000) stresses. The functional characterization of SlARF2 knockdown tomato mutants revealed that the downregulation of this gene enhanced primary root length and root branching and reduced plant wilting. At the physiological level, the arf2 mutant line displayed higher chlorophyll, soluble sugars, proline, and relative water contents as well as lower stomatal conductance and a decreased malondialdehyde content. Moreover, SlARF2 knockdown tomato mutants demonstrated higher activities of the antioxidant enzymes superoxide dismutase (SOD) and catalase (CAT) under salt and drought stresses than the wild type. Indeed, the stress tolerance of the arf2 mutant was also reflected by the upregulation of stress-related genes involved in ROS scavenging and plant defense, including SOD, CAT, dehydration-responsive element-binding protein, and early responsive to dehydration, which can ultimately result in a better resistance to salt and drought stresses. Furthermore, the transcriptional levels of the Δ1-pyrroline-5-carboxylate synthase (P5CS) gene were upregulated in the arf2 mutant after stress, in correlation with the higher levels of proline. Taken together, our findings reveal that SlARF2 is implicated in salt and drought tolerance in tomato and provides some considerable elements for improving the abiotic stress tolerance and increasing the crop yields of tomato. Full article
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16 pages, 1881 KiB  
Article
Contributing to Biochemistry and Optoelectronics: Pyrrolo[1′,2′:2,3]imidazo[1,5-a]indoles and Cyclohepta[4,5]pyrrolo[1,2-c]pyrrolo[1,2-a]imidazoles via [3+2] Annulation of Acylethynylcycloalka[b]pyrroles with Δ1-Pyrrolines
by Ludmila A. Oparina, Nikita A. Kolyvanov, Igor A. Ushakov, Lina P. Nikitina, Olga V. Petrova, Lyubov N. Sobenina, Konstantin B. Petrushenko and Boris A. Trofimov
Int. J. Mol. Sci. 2023, 24(4), 3404; https://doi.org/10.3390/ijms24043404 - 8 Feb 2023
Cited by 5 | Viewed by 3592
Abstract
Available pyrrolylalkynones with tetrahydroindolyl, cycloalkanopyrrolyl, and dihydrobenzo[g]indolyl moieties, acylethynylcycloalka[b]pyrroles, are readily annulated with Δ1-pyrrolines (MeCN/THF, 70 °C, 8 h) to afford a series of novel pyrrolo[1′,2′:2,3]imidazo[1,5-a]indoles and cyclohepta[4,5]pyrrolo[1,2-c]pyrrolo[1,2-a]imidazoles functionalized with an [...] Read more.
Available pyrrolylalkynones with tetrahydroindolyl, cycloalkanopyrrolyl, and dihydrobenzo[g]indolyl moieties, acylethynylcycloalka[b]pyrroles, are readily annulated with Δ1-pyrrolines (MeCN/THF, 70 °C, 8 h) to afford a series of novel pyrrolo[1′,2′:2,3]imidazo[1,5-a]indoles and cyclohepta[4,5]pyrrolo[1,2-c]pyrrolo[1,2-a]imidazoles functionalized with an acylethenyl group in up to an 81% yield. This original synthetic approach contributes to the arsenal of chemical methods promoting drug discovery. Photophysical studies show that some of the synthesized compounds, e.g., benzo[g]pyrroloimidazoindoles, are prospective candidates for TADF emitters of OLED. Full article
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