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Background: Hyperlipidemia is a worldwide health problem and a significant risk factor for cardiovascular diseases; therefore, it imposes a heavy burden on society and healthcare. It has been reported that flavonoids can increase energy expenditure and fat oxidation, be anti-inflammatory, and reduce lipid factor levels, which may reduce the risk of hyperlipidemia. However, the relationship between the prevalence of hyperlipidemia and dietary flavonoid intake in the population remains unclear. Methods: This study included 8,940 adults from the 2007-2010 and 2017-2018 National Health and Nutrition Examination Surveys (NHANES). The relationship between dietary flavonoid intake and the prevalence of hyperlipidemia was analyzed using weighted logistic regression and weighted restricted cubic spline. Results: We found an inverse relationship between subtotal catechins intake and hyperlipidemia prevalence in the third quartile [0.74 (0.56, 0.98), p = 0.04] compared with the first quartile. The prevalence of hyperlipidemia and total flavan-3-ol intake in the third quartile were inversely correlated [0.76 (0.59, 0.98), p = 0.03]. Total anthocyanin intake was inversely related to the prevalence of hyperlipidemia in the third quartile [0.77 (0.62, 0.95), p = 0.02] and the fourth quartile [0.77 (0.60, 0.98), p = 0.04]. The prevalence of hyperlipidemia was negatively correlated with total flavonols intake in the fourth quartile [0.75 (0.60, 0.94), p = 0.02]. Using restricted cubic splines analysis, we found that subtotal catechins intake and total flavan-3-ol intake had a nonlinear relationship with the prevalence of hyperlipidemia. Conclusion: Our study may provide preliminary research evidence for personalizing improved dietary habits to reduce the prevalence of hyperlipidemia.

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Background: Hypertension is one of the major risk factors for cardiovascular disease. Dietary flavonoids have been reported to reduce inflammation, protect against oxidative stress, protect the vascular endothelium, and improve vascular health. However, the relationship between dietary flavonoid intake and the prevalence of hypertension remains controversial. Methods: This study included 8010 adults from the 2007-2010 and 2017-2018 National Health and Nutrition Examination Surveys (NHANES). The relationship between dietary flavonoid intake and the prevalence of hypertension was explored by weighted logistic regression and weighted restricted cubic spline. Results: We found an inverse relationship between total anthocyanin intake and the prevalence of hypertension in the fourth quartile compared with the first quartile [0.81(0.66,0.99), p = 0.04]. Moreover, the prevalence of hypertension tended to decrease with increasing total anthocyanin intake in participants over 60 years of age. In addition, we found a U-shaped relationship between the prevalence of hypertension and total flavan-3-ol intake. Total flavan-3-ol intake was inversely associated with hypertension prevalence in the third quartile compared with the first quartile [0.79 (0.63,0.99), p = 0.04]. Moreover, there was a significant negative association between the prevalence of hypertension and total flavan-3-ol intake when total flavan-3-ol intake was below 48.26 mg/day. Conclusion: Our study found a negative association between the prevalence of hypertension and moderate total anthocyanins intake and total flavan-3-ols intake. Our study provides evidence from a population-based study for a negative association between dietary flavonoid intake and the prevalence of hypertension.

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Astringency influences the sensory characteristics and flavor quality of table grapes. We tested the astringency sensory attributes of berries and investigated the concentration of flavan-3-ols/proanthocyanidins (PAs) in skins after the application of the plant growth regulators CPPU and GA3 to the flowers and young berries of the "Summer Black" grape. Our results showed that CPPU and GA3 applications increase sensory astringency perception scores and flavan-3-ol/proanthocyanidin concentrations. Using integrated transcriptomic and proteomic analysis, differentially expressed transcripts and proteins associated with growth regulator treatment were identified, including those for flavonoid biosynthesis that contribute to the changes in sensory astringency levels. Transient overexpression of candidate astringency-related regulatory genes in grape leaves revealed that VvWRKY71, in combination with VvMYBPA1 and VvMYC1, could promote the biosynthesis of proanthocyanidins, while overexpression of VvNAC83 reduced the accumulation of proanthocyanidins. However, in transient promoter studies in Nicotiana benthamiana, VvWRKY71 repressed the promoter of VvMYBPA2, while VvNAC83 had no significant effect on the promoter activity of four PA-related genes, and VvMYBPA1 was shown to activate its own promoter. This study provides new insights into the molecular mechanisms of sensory astringency formation induced by plant growth regulators in grape berries.

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The discovery of novel flavonoids and elucidation of their biosynthesis are fundamental to understanding their roles in plants and their benefits for human and animal health. Here, we report a new pathway for polymerization of a group of novel oligomeric flavonoids in plants. We engineered red cells for discovering genes of interest involved in the flavonoid pathway and identified a gene encoding a novel flavanol polymerase (FP) localized in the central vacuole. FP catalyzes the polymerization of flavanols, such as epicatechin and catechin, to produce yellowish dimers or oligomers. Structural elucidation shows that these compounds feature a novel oligomeric flaven-flavan (FF) skeleton linked by interflavan-flaven and interflaven bonds, distinguishing them from proanthocyanidins and dehydrodicatechins. Detailed chemical and physical characterizations further confirmed the novel FFs as flavonoids. Mechanistic investigations demonstrated that FP polymerizes flavan-3-ols and flav-2-en-3-ol carbocation, forming dimeric or oligomeric flaven-4→8-flavans, which we term "papanridins." Data from transgenic experiments, mutant analysis, metabolic profiling, and phylogenetic analyses show that the biosynthesis of papanridins is prevalent in cacao, grape, blueberry, corn, rice, Arabidopsis, and other species in the plant kingdom. In summary, our study discoveries a group of novel oligomeric flavonoids, namely papanridins, and reveals that a novel FP-mediated polymerization mechanism for the biosynthesis of papanridins in plants.

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SCOPE: Dietary flavan-3-ols are known to mediate cardiovascular benefits. Currently, it is assumed that the levels of flavan-3-ol catabolites detected in humans, 5-(3',4'-dihydroxyphenyl)-γ-valerolactone (γVL) and 5-(3',4'-dihydroxyphenyl)-γ-valeric acid (γVA), and their corresponding phase II metabolites, are determined exclusively by the action of the gut microbiome. However, a family of human proteins, paraoxonase (PON), can theoretically hydrolyze γVL metabolites into the corresponding γVAs. This study aims to determine if PON is involved in γVL and γVA metabolism in humans. METHODS AND RESULTS: A rapid conversion of γVL into γVA is detected in serum ex vivo (half-life = 9.8 ± 0.3 min) that is catalyzed by PON1 and PON3 isoforms. Phase II metabolites of γVL are also reacted with PON in serum. Following an intake of flavan-3-ol in healthy males (n = 13), the profile of γVA metabolites detected is consistent with that predicted from the reactivity of γVL metabolites with PON in serum. Furthermore, common PON polymorphisms are evaluated to assess the use of γVL metabolites as biomarkers of flavan-3-ol intake. CONCLUSION: PONs are involved in flavan-3-ol metabolic pathway in humans. PON polymorphisms have a minor contribution to inter-individual differences in the levels of γVL metabolites, without affecting their use as a nutritional biomarker.

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Recent years have seen an increase in research focusing on the amelioration of apple pomace waste for use in the food and nutraceutical industries. Much of this work has concentrated on the characterisation of the polyphenol composition of apple pomace materials to determine their role in conferring nutritional and health benefits. Although apples contain substantial quantities of polymeric procyanidins (condensed tannins), this class of compounds has received limited attention in apple research. This study quantified the polymeric procyanidins in apple pomace extracts using a rapid, methyl-cellulose precipitation (MCP) approach for the first time. In addition, a non-targeted metabolomics approach was applied to determine the most abundant phenolic classes present. Polymeric procyanidins were found to be the most abundant type of polyphenol in apple pomace extracts and were generally oligomeric in nature. Multivariate statistical analysis revealed that the ferric-reducing antioxidant power (FRAP) was most strongly correlated with the polymeric procyanidin concentration. Noting that polymeric procyanidins may not cross the cell layer to exert antioxidant activity in vivo, their presence in apple pomace extracts may therefore overestimate the FRAP. This work highlights the importance of polymeric procyanidins in the phenolic diversity of apple pomaces, and it is proposed that in future studies, rapid MCP assays may be used for their quantification.

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Condensed tannins (CT) in wine are derived from the seeds and skins of grapes, and their composition and content contribute to the bitterness/astringency characteristics and ageing potential of the wine. Global warming has accelerated the ripening process of grape berries, making them out of sync with seed ripening. To understand the influence of berry ripening on the seed CT composition and content, we analyzed the changes in the soluble and insoluble CT in the seeds of 'Cabernet Sauvignon' grapes from two vineyards over two years. The results showed that the seed-soluble CT presented a slight downward trend in fluctuation during grape berry development, while the insoluble CT increased continuously before the véraison and remained at a high level afterwards. Relatively speaking, a lower sugar increment in developing grape berries favored the conversion of seed CT towards a higher degree of polymerization. The terminal unit of soluble CT was dominated by epigallocatechin gallate, the content of which decreased as the seeds matured. It is suggested that the seeds should be fully matured to reduce this bitter component in tannins. This study provides a reference for us to control the grape ripening process and produce high-quality grapes for wine making.

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BACKGROUND: Although experimental evidence supports anticancer effects of flavonoids, the influence of flavonoid intake on colorectal cancer (CRC) survival remains unknown. OBJECTIVES: This study aimed to assess the association of postdiagnostic flavonoid intake with mortality. METHODS: We prospectively assessed the association of postdiagnostic flavonoid intake with CRC-specific and all-cause mortality in 2552 patients diagnosed with stage I-III CRC in 2 cohort studies-the Nurses' Health Study and the Health Professionals Follow-up Study. We assessed the intake of total flavonoids and their subclasses using validated food frequency questionnaires. We used the inverse probability-weighted multivariable Cox proportional hazards regression model to calculate the hazard ratio (HR) of mortality after adjusting for prediagnostic flavonoid intake and other potential confounders. We performed spline analysis to evaluate dose-response relationships. RESULTS: The mean [standard deviation (SD)] age of patients at diagnosis was 68.7 (9.4) y. During 31,026 person-y of follow-up, we documented 1689 deaths, of which 327 were due to CRC. The total flavonoid intake was not associated with mortality, but a higher intake of flavan-3-ols was suggestively associated with lower CRC-specific and all-cause mortality, with multivariable HR (95% CI) per 1-SD increases of 0.83 (0.69-0.99; P = 0.04) and 0.91 (0.84-0.99; P = 0.02), respectively. The spline analysis showed a linear relationship between postdiagnostic flavan-3-ol intake and CRC-specific mortality (P = 0.01 for linearity). As the major contributor to flavan-3-ol intake, tea showed an inverse association with CRC-specific and all-cause mortality, with multivariable HRs per 1 cup/d of tea of 0.86 (0.75-0.99; P = 0.03) and 0.90 (0.85-0.95; P < 0.001), respectively. No beneficial associations were found for other flavonoid subclasses. CONCLUSIONS: Higher intake of flavan-3-ol after CRC diagnosis was associated with lower CRC-specific mortality. Small, readily achievable increases in the intake of flavan-3-ol-rich foods, such as tea, may help improve survival in patients with CRC.

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Thirteen varieties of feijoa (Feijoa sellowiana) fruit were collected and the physical and chemical properties of feijoa peel, flesh, seed, and leaf were analyzed. Large diversities in the physicochemical characteristics and phenolic and volatile composition among various parts and between different varieties of feijoa were observed. Degrees Brix of whole fruits ranged from 10.1 (Anatoki) to 18.0 (No. 2) °Brix. Procyanidin B-type tetramer, procyanidin B-type dimer, and procyanidin C-type trimer had the highest concentrations in all parts and varieties of feijoa. Caffeoyl glucose, dihydroferulic acid 4-O-glucuronide, galloyl glucose, and lariciresinol-sesquilignan were detected in feijoa fruits and leaves. A total of 105 esters, 68 terpenes, 20 alcohols, 31 hydrocarbons, 12 aldehydes, and 11 ketones were related to aromatic attributes of fruits and leaves. Early season and mid-season varieties had larger variations in the chemical properties than late-season varieties. Anatoki, Kakariki, and No.1, have the potential to be developed for attractive flavor and functional properties.

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Flavan-3-ols, including the flavan-3-ol monomer (-)-epicatechin, are dietary bioactives known to mediate beneficial cardiovascular effects in humans. Recent studies showed that flavan-3-ols could interact with methylxanthines, evidenced by an increase in flavan-3-ol bioavailability with a concomitant increase in flavan-3-ol intake-mediated vascular effects. This study aimed at elucidating flavan-3-ol-methylxanthine interactions in humans in vivo by evaluating the specific contributions of theobromine and caffeine on flavan-3-ol bioavailability. In ileostomists, the effect of methylxanthines on the efflux of flavan-3-ol metabolites in the small intestine was assessed, a parameter important to an understanding of the pharmacokinetics of flavan-3-ols in humans. In a randomized, controlled, triple cross-over study in volunteers with a functional colon (n = 10), co-ingestion of flavan-3-ols and cocoa methylxanthines, mainly represented by theobromine, increased peak circulatory levels (Cmax) of flavan-3-ols metabolites (+21 ± 8%; p < 0.05). Conversely, caffeine did not mediate a statistically significant effect on flavan-3-ol bioavailability (Cmax = +10 ± 8%, p = n.s.). In a subsequent randomized, controlled, double cross-over study in ileostomists (n = 10), cocoa methylxanthines did not affect circulatory levels of flavan-3-ol metabolites, suggesting potential differences in flavan-3-ol bioavailability compared to volunteers with a functional colon. The main metabolite in ileal fluid was (-)-epicatechin-3'-sulfate, however, no differences in flavan-3-ol metabolites in ileal fluid were observed after flavan-3-ol intake with and without cocoa methylxanthines. Taken together, these results demonstrate a differential effect of caffeine and theobromine in modulating flavan-3-ol bioavailability when these bioactives are co-ingested. These findings should be considered when comparing the effects mediated by the intake of flavan-3-ol-containing foods and beverages and the amount and type of methylxanthines present in the ingested matrixes. Ultimately, these insights will be of value to further optimize current dietary recommendations for flavan-3-ol intake. CLINICAL TRIAL REGISTRATION NUMBER: This work was registered at clinicaltrials.gov as NCT03526107 (study part 1, volunteers with functional colon) and NCT03765606 (study part 2, volunteers with an ileostomy).

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The influence and its mechanism of ultrasound on acetaldehyde/glyoxylic acid competing bridged the polymerization coloration of flavan-3-ols in model wine solution were investigated by high-performance liquid chromatography-mass spectrometry (HPLC-MS) and kinetics and thermodynamic model. The results indicate that ultrasound could significantly accelerate the polymerization coloration and further modify wine color. In addition, the polymerization reaction conformed first-order reaction model, and the reaction rate constant (k) values were markedly increased by ultrasound, accelerating the coloration reaction, especially in the model wine containing glyoxylic acid. Besides, the polymerization processing was non-spontaneous and endothermic according to the thermodynamic analysis. In conclusion, ultrasound was indeed conducive to accelerate glyoxylic acid/acetaldehyde-bridged the polymerization of flavan-3-ols and further effect the wine color, which could provide a theoretical basis for the scientific analysis of the mechanism of ultrasound modifying wine color.

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The high accumulation of galloylated flavan-3-ols in Camellia sp. is a noteworthy phenomenon. We identified a flavan-3-ol galloylation-related functional gene cluster in tannin-rich plant Camellia sp., which included UGT84A22 and SCPL-AT gene clusters. We investigated the possible correlation between the accumulation of metabolites and the expression of SCPL-ATs and UGT84A22. The results revealed that C. sinensis, C. ptilophylla, and C. oleifera accumulated galloylated cis-flavan-3-ols (EGCG), galloylated trans-flavan-3-ols (GCG), and hydrolyzed tannins, respectively; however, C. nitidissima did not accumulate any galloylated compounds. C. nitidissima exhibited no expression of SCPL-AT or UGT84A22, whereas the other three species of Camellia exhibited various expression patterns. This indicated that the functions of the paralogs of SCPL-AT vary. Enzymatic analysis revealed that SCPL5 was neofunctionalized as a noncatalytic chaperone paralog, a type of chaerone-like protein, associating with flavan-3-ol galloylation; moreover, CsSCPL4 was subfunctionalized in association with the galloylation of cis- and trans-flavan-3-ols. In C. nitidissima, an SCPL4 homolog was noted with mutations in two cysteine residues forming a disulfide bond, which suggested that this homolog was defunctionalized. The findings of this study improve our understanding of the functional diversification of SCPL paralogs in Camellia sp.

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Theobroma grandiflorum, T. bicolor and T. subincanum represent underutilized genetic resources for cocoa quality. The bioactive components and flavor volatiles of different bean genotypes of these species were profiled and compared with those of T. cacao. T. bicolor and T. grandiflorum had different profiles of methylxanthines and polyphenols from T. bicolor and T. cacao. T. subincanum and T. grandiflorum were rich in theacrine and flavones. T. grandiflorum, T. bicolor and T. subincanum beans generally had less phenolics than T. cacao. Roasting decreased the concentrations of polyphenols and methylxanthines in the beans. Roasted T. grandiflorum and T. subincanum beans had higher concentrations of pyrazines and esters than T. cacao. T. grandiflorum and T. subincanum beans had more odor-active volatiles than T. cacao. Overall, the underutilized Theobroma species have potential to be exploited to improve the flavor and nutritional quality of cocoa products.

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Dehydrodicatechins resulting from (epi)catechin oxidation have been investigated in different foods and natural products, but they still offer some analytical challenges. The purpose of this research is to develop a method using ultra-high performance liquid chromatography coupled with trapped ion mobility spectrometry and tandem mass spectrometry (UHPLC-ESI-TIMS-QTOF-MS/MS) to improve the characterization of dehydrodicatechins from model solutions (oxidation dimers of (+)-catechin and/or (-)-epicatechin). Approximately 30 dehydrodicatechins were detected in the model solutions, including dehydrodicatechins B with ß and ε-interflavanic configurations and dehydrodicatechins A with γ-configuration. A total of 11 dehydrodicatechins B, based on (-)-epicatechin, (+)-catechin, or both, were tentatively identified in a grape seed extract. All of them were of ß-configuration, except for one compound that was of ε-configuration. TIMS allowed the mobility separation of chromatographically coeluted isomers including dehydrodicatechins and procyanidins with similar MS/MS fragmentation patterns that would hardly be distinguished by LC-MS/MS alone, which demonstrates the superiority of TIMS added to LC-MS/MS for these kinds of compounds. To the best of our knowledge, this is the first time that ion mobility spectrometry (IMS) was applied to the analysis of dehydrodicatechins. This method can be adapted for other natural products.

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Background and Aim: Angiostrongylus eosinophilic meningitis is caused by larvae of the rat lungworm Angiostrongylus cantonensis. It manifests as meningitis, radiculitis, cranial nerve abnormalities, and encephalitis, which can be fatal. A flavan-3-ol compound isolated from the bark of Calophyllum macrophyllum Scheff. has several medicinal properties, including antioxidant, anti-inflammatory, antidiabetic, and antibacterial activities. This compound is stronger than other types of flavan-3-ols such as catechin. This study aimed to identify the hydroxylation pattern of this flavan-3-ol compound and evaluated its potential as an anti-meningitis drug, using an in silico approach through pharmacophore and molecular docking methods. Materials and Methods: Pharmacokinetic and toxicological data were analyzed and supported by the server http://www.swissadme.ch/index.php and https://tox-new.charite.de/protox_II/index.php. The hydroxylation pattern of the flavan-3-ol compound was identified using shear reagents (MeOH, NaOH, NaOAc, HCl, and AlCl3). The CviR receptor (pdb id.3QP5) was used in the in silico approach, and seven ligands were downloaded from PubChem in "SMILES" format. Results: The spectroscopic analysis conducted using the shear reagents confirmed that the flavan-3-ol compound has a "p-diOH" pattern on the cinnamoyl ring. Pharmacophore analysis revealed this compound "hit" with pharmacophore features, and molecular docking analysis showed that this compound has a strong affinity with both receptors. Conclusion: The flavan-3-ol compound is a potential drug candidate for meningitis caused by pathogenic bacteria and the worm A. cantonensis. This result was supported by the pharmacokinetic profile, which had a very low toxicity level to the host. However, further investigation is required to confirm the data in vitro and in vivo.

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Tetrapleura tetraptera is a medicinal plant used in East and West Africa to treat inflammation and related diseases. From the stem bark of the plant, three previously undescribed flavan-3-ol derivatives named (2R,3S)-3,3',5',7-tetrahydroxy-4'-methoxyflavane (1), (2R,3S)-3',5',7-trihydroxy-4'-methoxyflavane-3-O-ß-D-glucopyranoside (2), and (2R,3S,4S)-3,3',4,5',7-pentahydroxy-4'-methoxyflavane (3) were isolated with three known analogues. The structural elucidation of the compounds was performed based on NMR spectroscopy and HRMS data analyses. The absolute configurations around the stereogenic carbons were determined using Circular Dichroism (ECD) and density functional theory (DFT) calculations. The cytotoxicity of the isolated compounds was tested using resazurin reduction assay. Compound 1 was moderately active against both recalcitrant leukemia cell lines with IC50 values of 21.90 µM towards CCRF-CEM and 50.80 towards CEM/ADR5000. Similar level of activity was observed for compound 3 against CCRF-CEM cell line, IC50 = 35.50 µM. All the tested compounds were not cytotoxic compared with the standard drug, doxorubicin, with IC50 values of 0.0075 against CCRF-CEM and 24.30 µM against CEM/ADR5000.

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Cynomorium songaricum is a traditional medicine and also a food material that is eaten raw or processed as tea or beverages. As a featured plant in semi-desert grasslands, C. songaricum is also eaten by the cattle and sheep in the area. This research study fed dairy sheep C. songaricum to determine the flavan-3-ols in sheep milk. Catechin (Cat), epicatechin (Epi), procyanidin A1 (A1), procyanidin A2 (A2), and procyanidin B1 (B1) were detected in sheep milk with the concentration being Epi > A2 > Cat > B1 > A1 at 24 h after the administration of C. songaricum. Neither A1 nor A2 were detected in the methanol extract of C. songaricum. Cysteine degradation of the plant revealed that in addition to Epi, A2 was the extending unit of the polymeric flavan-3-ols in C. songaricum, indicating that A2 is released digestively from the polymers and enters the milk. Procyanidin B-1 was converted to A1 on incubation in raw but not heated milk, indicating that the A1 in milk is the enzymatically transformed product of B1. Accelerated oxidation showed that the flavan-3-ols, B1, Cat, and Epi significantly protects the unsaturated triacyglycerols in the milk from oxidation. The flavan-3-ol could slow down the oxidation of glutathione and the latter may play an important role in preventing the milk triglycerides from oxidation. Flavan-3-ols are polyphenols with many health benefits. The present research revealed the antioxidant activities of flavan-3-ols that could be absorbed to sheep milk, adding new evidences for the values of these flavan-3-ols and for the milk.

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Serine carboxypeptidase-like acyltransferases (SCPL-ATs) play a vital role in the diversification of plant metabolites. Galloylated flavan-3-ols highly accumulate in tea (Camellia sinensis), grape (Vitis vinifera), and persimmon (Diospyros kaki). To date, the biosynthetic mechanism of these compounds remains unknown. Herein, we report that two SCPL-AT paralogs are involved in galloylation of flavan-3-ols: CsSCPL4, which contains the conserved catalytic triad S-D-H, and CsSCPL5, which has the alternative triad T-D-Y. Integrated data from transgenic plants, recombinant enzymes, and gene mutations showed that CsSCPL4 is a catalytic acyltransferase, while CsSCPL5 is a non-catalytic companion paralog (NCCP). Co-expression of CsSCPL4 and CsSCPL5 is likely responsible for the galloylation. Furthermore, pull-down and co-immunoprecipitation assays showed that CsSCPL4 and CsSCPL5 interact, increasing protein stability and promoting post-translational processing. Moreover, phylogenetic analyses revealed that their homologs co-exist in galloylated flavan-3-ol- or hydrolyzable tannin-rich plant species. Enzymatic assays further revealed the necessity of co-expression of those homologs for acyltransferase activity. Evolution analysis revealed that the mutations of the CsSCPL5 catalytic residues may have taken place about 10 million years ago. These findings show that the co-expression of SCPL-ATs and their NCCPs contributes to the acylation of flavan-3-ols in the plant kingdom.

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Red wine is a very complex medium in which condensed tannins undergo many modifications during winemaking and bottle ageing. These reactions have an impact on the organoleptic properties. This work aimed to highlight tannins evolution related to wine evolution by studying three vintages of Syrah wines. An accelerated oxidation was also undertaken in order to evaluate the ability of this oxidation to imitate natural evolution. After chemical depolymerization of the tannins, the monitoring of 6 types of markers at two oxidation levels was investigated. An evolution of the tannin oxidation state during ageing evidenced by the increase of the markers of the second oxidation level was observed. In the 2018 oxidized wine sample, the first oxidation level markers were similar to the 2014 vintage but the second oxidation level markers were higher than other vintages, indicating a more advanced state of tannin oxidation.

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Ebola virus disease (EVD), a disease caused by infection with Ebola virus (EBOV), is characterized by hemorrhagic fever and a high case fatality rate. With limited options for the treatment of EVD, anti-Ebola viral therapeutics need to be urgently developed. In this study, over 500 extracts of medicinal plants collected in the Lingnan region were tested against infection with Ebola-virus-pseudotyped particles (EBOVpp), leading to the discovery of Maesa perlarius as an anti-EBOV plant lead. The methanol extract (MPBE) of the stems of this plant showed an inhibitory effect against EBOVpp, with an IC50 value of 0.52 µg/mL, which was confirmed by testing the extract against infectious EBOV in a biosafety level 4 laboratory. The bioassay-guided fractionation of MPBE resulted in three proanthocyanidins (procyanidin B2 (1), procyanidin C1 (2), and epicatechin-(4ß→8)-epicatechin-(4ß→8)-epicatechin-(4ß→8)-epicatechin (3)), along with two flavan-3-ols ((+)-catechin (4) and (-)-epicatechin (5)). The IC50 values of the compounds against pseudovirion-bearing EBOV-GP ranged from 0.83 to 36.0 µM, with 1 as the most potent inhibitor. The anti-EBOV activities of five synthetic derivatives together with six commercially available analogues, including EGCG ((-)-epigallocatechin-3-O-gallate (8)), were further investigated. Molecular docking analysis and binding affinity measurement suggested the EBOV glycoprotein could be a potential molecular target for 1 and its related compounds.

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