MgH2@Mg(BH4)2 Core-Shell-like Nanostructures: Synthesis, Hydrolysis Performance, and Promotion Mechanism.

The hydrolysis of hydrides, represented by MgH2, delivers substantial capacity and presents an appealing prospect for an on-site hydrogen supply. However, the sluggish hydrolysis kinetics and low hydrogen yield of MgH2 caused by the formation of a passivation Mg(OH)2 layer hinder its practical application. Herein, we present a dual strategy encompassing microstructural design and compounding, leading to the successful synthesis of a core-shell-like nanostructured MgH2@Mg(BH4)2 composite, which demonstrates excellent hydrolysis performance. Specifically, the optimal composite with a low Ea of 9.05 kJ mol-1 releases 2027.7 mL g-1 H2 in 60 min, and its hydrolysis rate escalates to 1356.7 mL g-1 min-1 H2 during the first minute at room temperature. The nanocoating Mg(BH4)2 plays a key role in enhancing the hydrolysis kinetics through the release of heat and the formation of local concentration of Mg2+ field after its hydrolysis. This work offers an innovative concept for the design of hydrolysis materials.

Genome-wide identification and transcriptome profiling expression analysis of the U-box E3 ubiquitin ligase gene family related to abiotic stress in maize (Zea mays L.).

BACKGROUND: The U-box gene family encodes E3 ubiquitin ligases involved in plant hormone signaling pathways and abiotic stress responses. However, there has yet to be a comprehensive analysis of the U-box gene family in maize (Zea mays L.) and its responses to abiotic stress. RESULTS: In this study, 85 U-box family proteins were identified in maize and were classified into four subfamilies based on phylogenetic analysis. In addition to the conserved U-box domain, we identified additional functional domains, including Pkinase, ARM, KAP and Tyr domains, by analyzing the conserved motifs and gene structures. Chromosomal localization and collinearity analysis revealed that gene duplications may have contributed to the expansion and evolution of the U-box gene family. GO annotation and KEGG pathway enrichment analysis identified a total of 105 GO terms and 21 KEGG pathways that were notably enriched, including ubiquitin-protein transferase activity, ubiquitin conjugating enzyme activity and ubiquitin-mediated proteolysis pathway. Tissue expression analysis showed that some ZmPUB genes were specifically expressed in certain tissues and that this could be due to their functions. In addition, RNA-seq data for maize seedlings under salt stress revealed 16 stress-inducible plant U-box genes, of which 10 genes were upregulated and 6 genes were downregulated. The qRT-PCR results for genes responding to abiotic stress were consistent with the transcriptome analysis. Among them, ZmPUB13, ZmPUB18, ZmPUB19 and ZmPUB68 were upregulated under all three abiotic stress conditions. Subcellular localization analysis showed that ZmPUB19 and ZmPUB59 were located in the nucleus. CONCLUSIONS: Overall, our study provides a comprehensive analysis of the U-box gene family in maize and its responses to abiotic stress, suggesting that U-box genes play an important role in the stress response and providing insights into the regulatory mechanisms underlying the response to abiotic stress in maize.

Identification and Expression Analysis of the Nucleotidyl Transferase Protein (NTP) Family in Soybean (Glycine max) under Various Abiotic Stresses.

Nucleotidyl transferases (NTPs) are common transferases in eukaryotes and play a crucial role in nucleotide modifications at the 3' end of RNA. In plants, NTPs can regulate RNA stability by influencing 3' end modifications, which in turn affect plant growth, development, stress responses, and disease resistance. Although the functions of NTP family members have been extensively studied in Arabidopsis, rice, and maize, there is limited knowledge about NTP genes in soybeans. In this study, we identified 16 members of the NTP family in soybeans, including two subfamilies (G1 and G2) with distinct secondary structures, conserved motifs, and domain distributions at the protein level. Evolutionary analysis of genes in the NTP family across multiple species and gene collinearity analysis revealed a relatively conserved evolutionary pattern. Analysis of the tertiary structure of the proteins showed that NTPs have three conserved aspartic acids that bind together to form a possible active site. Tissue-specific expression analysis indicated that some NTP genes exhibit tissue-specific expression, likely due to their specific functions. Stress expression analysis showed significant differences in the expression levels of NTP genes under high salt, drought, and cold stress. Additionally, RNA-seq analysis of soybean plants subjected to salt and drought stress further confirmed the association of soybean NTP genes with abiotic stress responses. Subcellular localization experiments revealed that GmNTP2 and GmNTP14, which likely have similar functions to HESO1 and URT1, are located in the nucleus. These research findings provide a foundation for further investigations into the functions of NTP family genes in soybeans.

Identification and expression of the CCO family during development, ripening and stress response in banana.

Plant hormone abscisic acid (ABA) plays an important role in plant growth, development and response to biotic / abiotic stressors. Thus, it is necessary to investigate the crucial genes associated with ABA synthesis. Currently, the carotenoid cleavage oxygenases (CCOs) family that function as the key step for ABA synthesis are not well understood in banana. In this study, 13 MaCCO genes and 12 MbCCO genes, divided into NCED subgroup and CCD subgroup, were identified from the banana genome, and their evolutionary relationship, protein motifs, and gene structures were also determined. Transcriptomic analysis suggested the involvement of CCO genes in banana development, ripening, and response to abiotic and biotic stressors, and homologous gene pairs showed homoeologue expression bias in the A or B subgenome. Our results identified MaNCED3A, MaCCD1, and MbNCED3B as the genes with the highest expression during fruit development and ripening. MaNCED5 / MbNCED5 and MaNCED9A might respond to abiotic stress, and MaNCED3A, 3B, 6 A, 9 A, and MbNCED9A showed transcriptional changes that could be a response to Foc4 infection. These findings may contribute to the characterization of key enzymes involved in ABA biosynthesis, as well as to identify potential targets for the genetic improvement of banana.

Silybin suppresses ovarian cancer cell proliferation by inhibiting isocitrate dehydrogenase 1 activity.

Metabolic reprogramming is a sign of malignant tumors, and targeting the metabolism of tumor cells has become a promising therapeutic approach. Here, we report that Silybin (a nontoxic flavonoid commonly used for liver protection) exhibits prominent anti-tumor effects on human ovarian cancer cells. Treatment of an ovarian cancer cell line with Silybin interfered with glutamine metabolism and the tricarboxylic acid cycle. We applied the drug affinity responsive target stability approach to show that Silybin binds to isocitrate dehydrogenase 1 (IDH1). This combination leads to reduced phosphorylation of IDH1 and inhibits enzyme activity. IDH1 dysfunction significantly increases the ratio of NADP/NADPH in the cell, causing an increase in reactive oxygen species generation. Immunohistochemistry demonstrated that IDH1 was increased in ovarian cancer samples compared with normal para-tumoral tissues. Xenograft murine experiments indicated that Silybin administered orally suppressed the growth of the tumor formed by ovarian cancer cells. In combination, our data strongly suggest that Silybin targets IDH1 in ovarian cancer cells and may be a novel treatment candidate.

SHARPIN promotes cell proliferation of cholangiocarcinoma and inhibits ferroptosis via p53/SLC7A11/GPX4 signaling.

SHARPIN is a tumor-associated gene involved in the growth and proliferation of many tumor types. A function of SHARPIN in cholangiocarcinoma (CCA) is so far unclear. Here, we studied the role and function of SHARPIN in CCA and revealed its relevant molecular mechanism. The expression of SHARPIN was analyzed in cholangiocarcinoma tissues from patients using immunohistochemistry, quantitative PCR, and western blot analysis. Expression of SHARPIN was suppressed/overexpressed by siRNA silencing or lentiviral overexpression vector, and the effect on cell proliferation was determined by the CCK-8 assay and flow cytometry. Accumulation of reactive oxygen species was measured with MitoTracker, and JC-1 staining showed mitochondrial fission/fusion and mitochondrial membrane potential changes as a result of the silencing or overexpression. The ferroptosis marker solute carrier family 7 member 11 (SLC7A11), glutathione peroxidase 4 (GPX4), and the antioxidant enzymes superoxide dismutase 1 (SOD-1) and SOD-2 were analyzed by western blot. The results showed that SHARPIN expression was increased in CCA tissue, and this was involved in cell proliferation. SHARPIN silencing resulted in accumulated reactive oxygen species, reduced mitochondrial fission, and a reduced mitochondrial membrane potential. Silencing of SHARPIN inhibited the ubiquitination and degradation of p53, and downregulated levels of SLC7A11, GPX4, SOD-1, and SOD-2, all of which contributed to excessive oxidative stress that leads to ferroptosis. Overexpression of SHARPIN would reverse the above process. The collected data suggest that in CCA, SHARPIN-mediated cell ferroptosis via the p53/SLC7A11/GPX4 signaling pathway is inhibited. Targeting SHARPIN might be a promising approach for the treatment of CCA.

A Review on Stems Composition and Their Impact on Wine Quality.

Often blamed for bringing green aromas and astringency to wines, the use of stems is also empirically known to improve the aromatic complexity and freshness of some wines. Although applied in different wine-growing regions, stems use remains mainly experimental at a cellar level. Few studies have specifically focused on the compounds extracted from stems during fermentation and maceration and their potential impact on the must and wine matrices. We identified current knowledge on stem chemical composition and inventoried the compounds likely to be released during maceration to consider their theoretical impact. In addition, we investigated existing studies that examined the impact of either single stems or whole clusters on the wine quality. Many parameters influence stems' effect on the wine, especially grape variety, stem state, how stems are incorporated, when they are added, and contact duration. Other rarely considered factors may also have an impact, including vintage and ripening conditions, which could affect the lignification of the stem.

Identification of RNA helicases in Medicago truncatula and their expression patterns under abiotic stress.

RNA helicase catalyzes the denaturation of DNA or the unwinding of double-stranded RNA. It is vital to RNA splicing, transport, editing, degradation and the initiation of protein translation. However, the function of RNA helicase in Medicago truncatula has rarely been reported. In this study, 170 putative RNA helicase genes were identified in the M. truncatula genome, and classified into three subfamilies based on the presence of either a DEAD-box (52 genes), DEAH-box (38 genes), or DExD/H-box (80 genes) in their coding regions. Additionally, conserved helicase_C domains and other functional domains (e.g., the HA2, DUF, and ZnF domains) were also present in these genes. Chromosomal mapping and synteny analyses showed that there were tandem and segment duplications of RNA helicase genes. Furthermore, transcriptome and real-time PCR analysis showed that the expression of 35 RNA helicase genes was affected by abiotic stress. To be specific, 17, 12 and 19 genes were regulated by salt, drought and cold stress, respectively. It is worth noting that MtDEAD8, MtDEAH3, MtDExD/H18 and MtDExD/H23 responded to all three types of stress. These results provide valuable information for understanding the RNA helicase genes in M. truncatula and their abiotic stress-related functions. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s12298-021-01087-y.

Crown Procyanidin Tetramer: A Procyanidin with an Unusual Cyclic Skeleton with a Potent Protective Effect against Amyloid-ß-Induced Toxicity.

The structure of a new procyanidin tetramer, which we call a crown procyanidin tetramer, with an unprecedented macrocyclic structure has been characterized for the first time. Its comprehensive spectroscopic analysis revealed that it is a symmetric procyanidin tetramer composed of four (-)-epicatechin sub-units linked alternatively via 4ß→8 or 4ß→6 B-type interflavanyl linkages to form the macrocyclic structure. This NMR-characterized carbon skeleton has never been reported before for procyanidins in grape or in wine, neither in the plant kingdom. Surprisingly, the crown procyanidin tetramer appeared to be specifically localized in grape skin, contrasting with the oligomeric and polymeric procyanidins present in seed, skin, and bunch stem. Moreover, this crown procyanidin tetramer showed promising protective effects against amyloid-ß induced toxicity.

PGC-1α activation: a therapeutic target for type 2 diabetes?

Peroxisome proliferator-activated receptor-γ coactivator-1α (PGC-1α) has gained popularity as a very attractive target for diabetic therapies due to its role in lipid and glucose metabolism. Pharmacological activation of PGC-1α is thought to elicit health benefits. However, this notion has been questioned by increasing evidence, which suggests that insulin resistant is exacerbated when PGC-1α expression is far beyond normal physiological limits and is prevented under the condition of PGC-1α deficiency. This narrative review suggests that PGC-1α, as a master metabolic regulator, exerts roles in insulin sensitivity in a tissue-specific manner and in a physical activity/age-dependent fashion. When using PGC-1α as a target for therapeutic strategies against insulin resistance and T2DM, we should take these factors into consideration.Level of evidence: Level V, narrative review.

ß-hydroxy-ß-methyl butyrate promotes leucine metabolism and improves muscle fibre composition in growing pigs.

The aim of this study was to investigate the effects of excess leucine (Leu) vs. its metabolites α-ketoisocaproate (KIC) and ß-hydroxy-ß-methyl butyrate (HMB) on Leu metabolism, muscle fibre composition and muscle growth in growing pigs. Thirty-two pigs with a similar initial weight (9.55 ± 0.19 kg) were fed 1 of 4 diets for 45 days: basal diet, basal diet + 1.25% L-Leu, basal diet + 1.25% KIC-Ca, basal diet + 0.62% HMB-Ca. Results indicated that relative to the basal diet and HMB groups, Leu and KIC groups exhibited increased Leu concentrations and decreased concentrations of isoleucine, valine and EAAs in selected muscle (p < 0.05) and had lower mRNA levels of MyHC I and higher expression of MyHC IIx/IIb (p < 0.05), and there was no significant difference between the basal and HMB-supplemented groups. Moreover, the mRNA expression levels of AMPKα and UCP3 were higher but the myostatin mRNA levels were lower in the soleus muscle of the HMB group than those from other groups (p < 0.05). These findings demonstrated that doubling dietary Leu content exerted growth-depressing effects in growing pigs; dietary KIC supplementation induced muscular branched-chain amino acid imbalance and promoted muscle toward a more glycolytic phenotype; while dietary HMB supplementation promoted the generation of more oxidative muscle types and increased muscle growth specially in oxidative skeletal muscle, and these effects of HMB might be associated with the AMPKα-Sirt1-PGC-1α axis and mitochondrial biogenesis.

The glutamine-alpha-ketoglutarate (AKG) metabolism and its nutritional implications.

L-Glutamine is a nutritionally semi-essential amino acid for proper growth in most cells and tissues, and plays an important role in the determination and guarding of the normal metabolic processes of the cells. With the help of transport systems, extracellular L-glutamine crosses the plasma membrane and is converted into alpha-ketoglutarate (AKG) through two pathways, namely, the glutaminase (GLS) I and II pathway. Reversely, AKG can be converted into glutamine by glutamate dehydrogenase (GDH) and glutamine synthetase (GS), or be converted into CO2 via the tricarboxylic acid (TCA) cycle and provide energy for the cells. Different steps of glutamine metabolism (the glutamine-AKG axis) are regulated by several factors, rendering the glutamine-AKG axis a potential target to counteract cancer. Moreover, intracellular glutamine plays an important role in cellular homeostasis not only as a precursor for protein synthesis, but also for its nutritional roles in cell growth, lipid metabolism, insulin secretion, and so on. The main objective of this review is to highlight the metabolic pathways of glutamine to AKG, with special emphasis on nutritional and therapeutic use of glutamine-AKG axis to improve the health and well-being of animals and humans.

Structures of polymeric pigments in red wine and their derived quantification markers revealed by high-resolution quadrupole time-of-flight mass spectrometry.

RATIONALE: The quantification of polymeric pigment families in red wine through their derived quantification markers released during phloroglucinolysis will allow the understanding of their formation kinetics and evolutions during aging which has not been achieved until now and is in urgent need. The identification of these quantification markers was achieved by high-resolution mass spectrometry (HRMS) in this study. METHODS: HRMS was used to clarify the fragmentation patterns in positive mode of polymeric pigments and identify their derived quantification markers released during phloroglucinolysis. RESULTS: With HRMS, identification of (epi)catechin-malvidin-3-O-glucoside adducts was simplified to MS/MS, and the fragmentation pattern of malvidin-3-O-glucoside-(epi)catechin adducts was clearly demonstrated. The attribution of four detected ions at m/z 1071.2765 in red wine to the trimeric structure of (epi)catechin-[malvidin-3-O-glucoside-A type linkage-(epi)catechin] and [malvidin-3-O-glucoside-A type linkage-(epi)catechin]-(epi)catechin was achieved for the first time by MS/MS and evidence given by phloroglucinolysis. Moreover, four kinds of derived quantification markers released from polymeric pigments during phloroglucinolysis were also identified. CONCLUSIONS: The fragmentation pathways of polymeric pigments in red wine and their derived quantification markers released during acidic chemical depolymerisation were clarified which will allow their quantification in red wine.

Phylogenic diversity and tissue specificity of fungal endophytes associated with the pharmaceutical plant, Stellera chamaejasme L. revealed by a cultivation-independent approach.

The fungal endophytes associated with medicinal plants have been demonstrated as a reservoir with novel natural products useful in medicine and agriculture. It is desirable to explore the species composition, diversity and tissue specificity of endophytic fungi that inhabit in different tissues of medicinal plants. In this study, a culture-independent survey of fungal diversity in the rhizosphere, leaves, stems and roots of a toxic medicinal plant, Stellera chamaejasme L., was conducted by sequence analysis of clone libraries of the partial internal transcribed spacer region. Altogether, 145 fungal OTUs (operational taxonomic units), represented by 464 sequences, were found in four samples, of these 109 OTUs (75.2 %) belonging to Ascomycota, 20 (13.8 %) to Basidiomycota, 14 (9.7 %) to Zygomycota, 1 (0.7 %) to Chytridiomycota, and 1 (0.7 %) to Glomeromycota. The richness and diversity of fungal communities were strongly influenced by plant tissue environments, and the roots are associated with a surprisingly rich endophyte community. The endophyte assemblages associated with S. chamaejasme were strongly shaped by plant tissue environments, and exhibited a certain degree of tissue specificity. Our results suggested that a wide variety of fungal assemblages inhabit in S. chamaejasme, and plant tissue environments conspicuously influence endophyte community structure.

Isolation and identification of chemical constituents from the bacterium Bacillus sp. and their nematicidal activities.

A strain SMrs28 was isolated from the rhizosphere soil of a toxic plant Stellera chamaejasme and identified as Bacillus sp. on the basis of morphological and partial 16S rRNA gene sequence analysis. The crude extract of SMrs28 fermentation broth showed strong nematocidal activities in preliminary test. To define the active nematocidal metabolites of SMrs28, a novel compound (1), 4-oxabicyclo[3.2.2]nona-1(7), 5,8-triene, along with five known compounds (2-6), were isolated from the strain by various column chromatographic techniques and characterized on the basis of spectroscopic analysis. Results of the in vitro nematicidal tests showed that the metabolites presented different levels of activity at certain exposure conditions. Compounds (1-3) displayed LC50 values of 904.12, 451.26, 232.98 µg/ml and 1594.0, 366.62, 206.38 µg/ml against Bursaphelenchus xylophilus and Ditylenchus destructor at 72 h, respectively. This is the first report of the nematicidal activity of the compounds as constituents of Bacillus sp.. Our findings help to find potential chemical structures to develop nematicides from microbial source for the management of nematode-infected plant diseases.

Hypersensitive quantification of major astringency markers in food and wine by substoichiometric quenching of silicon-rhodamine conjugates.

Tannins are chemically diverse polyphenols in plant-derived products that not only show diverse biological activities but also play a crucial role in determining the sensory attributes of food and beverages. Therefore, their accurate and cost-effective quantification is essential. Here, we identified a novel fluorescence quenching mechanism of different synthetic rhodamine fluorophores, with a high selectivity towards tannic acid (TA) and catechin-3-gallate (C3G) compared to a structurally diverse panel of tannins and polyphenols. Specific chemical conjugates of silicon-rhodamine with alkyl linkers attached to bulky apolar moieties had a limit of detection near 500 pM and a linear range spanning 5-100 nM for TA. We validated the assay on 18 distinct red wine samples, which showed high linearity (R2 = 0.92) with methylcellulose precipitation with no interference from anthocyanins. In conclusion, a novel assay was developed and validated that allows the sensitive and selective quantification of major astringency markers abundant in food and beverages.

Development of Distillation Sensors for Spirit Beverages Production Monitoring Based on Impedance Spectroscopy Measurement and Partial Least-Squares Regression.

During spirit beverages production, the distillate is divided into three parts: the head, the heart, and the tail. Acetaldehyde and ethanol are two key markers which allow the correct separation of distillate. Being toxic, the elimination of the head part, which contains a high concentration of acetaldehyde, is crucial to guarantee the consumer's health and security. Plus, the tail should be separated from the heart based on ethanol concentration. Nowadays, online or in-line sensors for acetaldehyde monitoring during distillation do not exist, and the online sensors for alcohol monitoring, based on density measurement, remain expensive for producers. In this work, we demonstrate the development of distillation monitoring sensors based on electrical impedance spectroscopy (EIS) measurements, combined with PLS-R (partial least-squares regression) modeling. Four types of sensors are proposed and tested with wine-based distillates. Using PLS-R, the best correlations were found for one electrode, named "SpotsSym". With an R 2 up to 89.9% for acetaldehyde concentration prediction and an R 2 up to 86.8% for ethanol, the obtained results indicate the promising potential of the proposed approach. To our knowledge, this is the first report of sensors capable of simultaneously measuring ethanol and acetaldehyde concentrations. Furthermore, these sensors offer the advantages of being low cost and nondestructive. Based on these results, the development of an in-line distillation monitoring system is possible in the near future, providing a promising tool for spirit beverages producers.

Alloying Pt into Ni partially amorphous for promoted alkaline hydrogen production.

Aiming at the sluggish water dissociation step in alkaline hydrogen evolution reaction (HER), the platinum-nickel alloy material (PtNi10/C) featuring unique crystalline/amorphous structure supported on carbon black is deliberately designed and fabricated via a reversely rapid co-precipitation and mild thermal reduction strategy. Electrochemical results show that only 66 mV of overpotential is needed for PtNi10/C to drive a current density of 10 mA cm-2 at a lower platinum loading (8.3 µgPt cm-2 geo), which is much lower than that of other catalysts with a single metal source(S-Ni/C and S-Pt/C) and even the commercial Pt/C catalyst (20 wt%). The target catalyst also exhibits smaller tafel slope value (16.73 mV dec-1) and electrochemical impedance value, enabling a fast kinetics rate for water dissociation. Partial crystallization facilitates moderate adsorption of intermediates, while the high-valence Ni(II) and Pt(II) species serve as pivotal driving force for the kinetic dissociation of water. The unique microstructure of PtNi10/C shows a remarkable advantage toward HER in alkaline but acidic medium. In addition, other transition metal-based catalysts following the similar protocol are also fabricated and present varying degrees of HER performance. Hence, the facile and rapid co-precipitation/thermal reduction strategy proposed in this study provides some guidelines for designing high-efficiency alkaline HER catalysts.

Lactate inhibits interferon-α response in ovarian cancer by inducing STAT1 ubiquitin degradation.

The emergence of lactate, produced by lactate dehydrogenase A (LDHA), as an important regulator of the immune response in tumor development has garnered attention in recent research. But, many questions still need to be clarified regarding the relationship between lactate and anti-tumor immunity. Here, we reported that both exogenous and endogenous lactate reduced the protein level and activation of the signal transducer and activator of transcription 1(STAT1) in ovarian cancer cells. As a consequence, the expression of IFNα-STAT1 regulated genes was weakened. This, in turn, weakened the antitumor effect of IFNα by impeding NKT and CD8+T cells recruitment. Strikingly, we found that LDHA knockdown did not result in the downregulation of STAT1 mRNA level in ovarian cancer cells. Instead, we observed that lactate triggered the degradation of STAT1 through the proteasomal pathway. Notably, we identified that lactate reduced the stability of STAT1 by promoting the expression of F-box only protein 40 (Fbxo40). This protein interacts with STAT1 and potentially acts as an E3 ubiquitin ligase, leading to the induction of STAT1 polyubiquitination and degradation. Importantly, ectopic over-expression of the Fbxo40 gene significantly inhibited the expression of ISGs in LDHA knockdown cells. In the TCGA tumor data, we observed that high expression of Fbxo40 negatively correlates with overall survival in ovarian cancer patients. Collectively, our findings reveal lactate as a negative regulator of the IFNα-STAT1 signaling axis in ovarian cancer. This discovery suggests that strategies aimed at targeting lactate for ovarian cancer prevention and treatment should consider the impact on the IFNα-STAT1 response.

Evolution of the Crown Procyanidins' Tetramer during Winemaking and Aging of Red Wine.

Condensed tannins play a major role in the quality of red wine. After grape extraction, they quickly evolve thanks to different oxidation mechanisms. Recently, NMR identified a new sub class of condensed tannins, named crown procyanidins, in red wine. The crown procyanidins' tetramer exhibits a macrocyclic structure composed of four (-)-epicatechin with an unusual cavity in the center of the molecule. These new tannins exposed a higher polarity than the linear tannins. In this work, the evolution kinetics of these crown procyanidins during the winemaking process and after aging of red wine in bottles were studied. Samples' quantification was analyzed by UPLC-UV-Q-TOF. The concentration of cyclic and non-cyclic procyanidins was compared. During the winemaking process, crown procyanidins are mainly extracted at the beginning of the alcoholic fermentation and they remain stable until the end of the winemaking process. The high polarity and solubility of this new molecule in water was confirmed. During the aging of red wine in bottles, crown procyanidins' concentrations are stable, whereas the non-cyclic tannins decrease dramatically. Finally, a strong oxygenation experiment confirmed the crown procyanidins' resistance to oxidation and unique skills.