Flavonoids, including proanthocyanidins (PAs), anthocyanins and flavonols are essential secondary metabolites that contribute to the nutritional value and sensory quality of grape berry and red wine. Advances in molecular biology technology have led to substantial progress in understanding the regulation of flavonoid biosynthesis. The influence of terroir on grape berries and wine has garnered increasing attention, yet its comprehensive regulatory network remains underexplored. In terms of application, environmental factors such as water, light, and temperature are more easily regulated in grapevines compared to soil conditions. Therefore, we summarize their effects on flavonoid content and composition, constructing a network that links environmental factors, hormones, and metabolites to provide a deeper understanding of the underlying mechanisms. This review enriches the knowledge of the regulatory network mechanisms governing flavonoid responses to environmental factors in grapes.

The objectives of this research were to analyze anthocyanins in blue honeysuckle (Lonicera caerulea L.), bilberry (Vaccinium vitis-idaea L), and cranberry (Vaccinium macrocarpon Ait.), using HPLC-ESI-QTOF-MS2, Fourteen, fifteen, and eight anthocyanins were identified in blue honeysuckle, bilberry, and cranberry, respectively. Cyanidin-3-glucoside (C3G) and peonidin-3-glucoside were detected in all three types of berries, with blue honeysuckle showing the highest C3G content at 5686.28 mg/100 g DW. Total phenolic content (TPC) and total flavonoid content (TFC), along with ABTS, DPPH, and FRAP assays, were measured. Blue honeysuckle exhibited the highest levels of TPC and TFC. The SOD, POD, and CAT activities in blue honeysuckle were 1761.17 U/g, 45,525.65 U/g, and 1043.24 U/g, respectively, which were significantly superior to those in bilberry and cranberry. The antioxidant mechanisms of these enzymes were investigated by molecular docking, C3G showed a higher affinity for POD, confirming the effectiveness of C3G as an antioxidant.

In this research, accelerated aroma release experiments and malvidin-3-O-glucoside copigmentation experiments in model red wine solutions were designed to investigate the abilities and molecular mechanisms of mannoproteins in modulating olfactory/chromatic properties of red wines. Results indicate that under orthonasal condition, mannoprotein MP2 was promising aroma modulator due to its predictable behaviors in expelling and retaining the aroma compounds during different periods. Low field nuclear magnetic resonance and molecular dynamic simulation proved that the modulation ability of MP2 should be explained by its transitionary interacting preferences with water/aroma compound molecules. Retronasal results show that the release of aroma compounds and olfactory perceptions were irregular and difficult to predict, probably due to the complexity of the retronasal condition. All mannoproteins protected malvidin-3-O-glucoside and quercetin via the formation of binary/ternary complexes, and quercetin was found prior to be protected than malvidin-3-O-glucoside. Principal mannoprotein A0A6C1DV26 might be the critical malvidin-3-O-glucoside protector. With the presence of quercetin, principal mannoproteins B3LQU1/B5VL26 in mannoprotein MP1 might exhibit intramolecular and/or intermolecular mechanisms that strengthened the hyperchromic effect, thus enhanced the copigmentation.

Due to its high polyphenol content, black rice plays a significant role in good nutrition; however, these antioxidant compounds are affected by heat treatments required for the rice consumption. The aim of this work was to investigate how cooking affects the composition of Artemide black rice, comparing innovative methods, such as sous vide, with traditional domestic techniques (risotto and pilaf). Proteins and ashes were not affected by cooking, except for pilaf rice, where a 42 % ashes decrease was observed; fiber content increased after all cooking methods, reaching a 29 % increase in the risotto. Antioxidant activity, total polyphenols, anthocyanins and proanthocyanidins were reduced on average of 40 %, 34 %, 43 % and 39 %, respectively. Individual anthocyanins decreased, while phenolic acids and other flavonoids presented different behaviours, also depending if considered in their free or bound form. Cyanidin-3-O-glucoside was reduced up to 56 % in the sous vide cooked rice at 99 °C, and only by 45 % and 37 % in the risotto and sous vide cooked rice at 89 °C, respectively. Traditional risotto preparation and the innovative sous vide cooking at 89 °C also maintained the highest antioxidant polyphenols content, saving 63 % of the antioxidant activity in respect to the raw black rice. Concluding, these last techniques can be suggested for a better preservation of bioactive compounds.

The clear juice fermentation technique for white wines suggests that white grape seeds, rich in flavan-3-ols and proanthocyanidins, are not effectively utilized in the winemaking process. This study incorporated \'Gewürztraminer\' grape seeds into \'Cabernet Sauvignon\' must before cold soak to investigate how the resultant red wines\' phenolic compound profiles, color, and astringency were affected. The results showed that adding seeds primarily inhibited the leaching of flavan-3-ols from both skins and seeds. A significant increase in the levels of flavan-3-ols, tannins, and phenolic acids, as well as direct and aldehyde-bridged flavan-3-ol-anthocyanin polymers, were observed in the wines with additional seeds. This led to the improvement in the wine\' red hue and its resistance to SO2 bleaching. Furthermore, the wine added with seeds exhibited stronger astringency compared to those without. The findings provide a promising winemaking strategy to improve color stability and intensify the astringency of red wines through the utilization of grape seeds.

The benefits of citrus fruits are strongly associated with their secondary metabolites. In this study, we conducted widely targeted metabolomics analyses to compare the variability of the ingredients in four scion-rootstock combinations. A total of 376 differential metabolites were obtained by a multivariate statistical analysis, and a KEGG pathway analysis showed that the enriched metabolic pathways were mainly related to the biosynthesis of flavonoids as well as lipid metabolism. The anthocyanin-targeted metabolomic features showed that cyanidin 3-O-glucoside, cyanidin 3-O-(6-O-malonyl-beta-D-glucoside), cyanidin 3-O-sophoroside, and cyanidin 3-O-xyloside were the pigments responsible for the red color of Tarocco. A lipid metabolomics analysis revealed that when Tarocco was hetero-grafted with rootstock H, there was an increase in the content of each lipid subclass, accompanied by an increase in the levels of unsaturated fatty acids, including polyunsaturated linoleic and linolenic acids, thus impacting the ratio of unsaturated fatty acids to saturated fatty acids. Additionally, we determined their antioxidant capacity (\'Trifoliate orange\' (Z) > \'Citrange\' (ZC) > \'Hongju\' (H) > \'Ziyang Xiangcheng\' (X)) using in vitro assays. Finally, we utilized a network pharmacology analysis to explore the antioxidant mechanisms and potential pharmacological ingredients; we obtained 26 core targets proteins and 42 core metabolites associated with oxidative damage, providing a basis for future preventive and therapeutic applications of these metabolites.

In this study, a series of novel nanofibers based on gelatin (GA) loading with purple potato anthocyanin (PPA) and syringic acid (SA) were obtained by electrospinning technology. The effects of SA on mechanical properties, thermal stability, antioxidant capacity, and antimicrobial activity of the GA/PPA nanofibers were systematically characterized. The scanning electron microscopy observation results revealed a smooth surface on the nanofibers. The incorporation of SA enhanced the viscosity of the electrospun solutions, and it increased the average diameter of nanofibers from 0.17 μm to 0.28 μm. The tensile strength and thermal stability of the obtained nanofibers were enhanced with the addition of a suitable level of SA (1.5%, w/v), which strengthened the intermolecular interaction. The GA/PPA/SA nanofibers presented over 80% antioxidant capacity and strong antibacterial activity against E. coli and S. aureus. Meanwhile, the sensitivity responses of nanofibers to NH3 revealed that GA/PPA/SA II nanofibers (1.5% w/v SA) presented good sensitivity of colorimetric behavior to ammonia. A pork spoilage test was performed to evaluate practical application of the nanofibers, and an obvious color change (dark purple to green) was observed. These results indicated GA/PPA/SA II nanofibers can be utilized as an active and intelligent multipurpose packaging material to preserve and track the freshness of pork.

BACKGROUND: Synchronous degradation between anthocyanin and vitamin C was found in fruit and vegetable juice matrices. To investigate whether the C-ring of anthocyanin is the key site of this interaction, cyanidin with four different C-ring modifications (3-glucosylation, 3,5-diglucosylation, 6″-malonylation, pyranylation) was added to vitamin C-containing apple juice, and the changes of anthocyanin retention, vitamin C retention, color, antioxidative activity and differential metabolites were analyzed.
RESULTS: The anthocyanin retention was in the order of pyranylation >6″-malonylation >3,5-diglucosylation >3-glucosylation. The vitamin C retention was in the order of 6″-malonylation > pyranylation >3,5-diglucosylation >3-glucosylation. The order of color stability was the same as that of anthocyanin retention, and the order of antioxidative activity was opposite to that of vitamin C retention. The results showed that modification at the C-ring limited the activity of anthocyanin, and suggested that the C-ring was one of the key sites for anthocyanin and vitamin C interaction. The shared differential metabolite of all apple juice matrices added with different anthocyanins was trans-hinokiresinol, which was likely generated from anthocyanin skeleton reacted with certain compounds in apple juice.
CONCLUSIONS: This study showed that modification of the anthocyanin C-ring could affect the anthocyanin and vitamin C interaction to some extent, which provided valuable insights for the application of anthocyanin C-ring modification in shelf-life quality control of typical fruit and vegetable beverages with the coexistence of anthocyanin and vitamin C. © 2024 Society of Chemical Industry.

BACKGROUND: In the past two decades, the impacts of Helium-Neon (He-Ne) laser on stress resistance and secondary metabolism in plants have been studied, but the signaling pathway which by laser regulates this process remains unclear. Therefore, the current study sought to explore the role of RBOH-dependent signaling in He-Ne laser-induced salt tolerance and elicitation of secondary metabolism in Salvia officinalis. Seeds were primed with He-Ne laser (6 J cm- 2) and peroxide hydrogen (H2O2, 5 mM) and 15-old-day plants were exposed to two salinity levels (0, 75 mM NaCl).
RESULTS: Salt stress reduced growth parameters, chlorophyll content and relative water content (RWC) and increased malodialdehyde (MDA) and H2O2 contents in leaves of 45-old-day plants. After 48 h of salt exposure, higher transcription levels of RBOH (encoding NADPH oxidase), PAL (phenylalanine ammonia-lyase), and RAS (rosmarinic acid synthase) were recorded in leaves of plants grown from seeds primed with He-Ne laser and/or H2O2. Despite laser up-regulated RBOH gene in the early hours of exposing to salinity, H2O2 and MDA contents were lower in leaves of these plants after 30 days. Seed pretreatment with He-Ne laser and/or H2O2 augmented the accumulation of anthocyanins, total phenol, carnasol, and rosmarinic acid and increased total antioxidant capacity under non-saline and more extensively at saline conditions. Indeed, these treatments improved RWC, and K+/Na+ ratio, enhanced the activities of superoxide dismutase and ascorbate peroxidase and proline accumulation, and significantly decreased membrane injury and H2O2 content in leaves of 45-old-day plants under salt stress. However, applying diphenylene iodonium (DPI as an inhibitor of NADPH oxidase) and N, N-dimethyl thiourea (DMTU as a H2O2 scavenger) after laser priming reversed the aforementioned effects which in turn resulted in the loss of laser-induced salt tolerance and secondary metabolism.
CONCLUSIONS: These findings for the first time deciphered that laser can induce a transient RBOH-dependent H2O2 burst, which might act as a downstream signal to promote secondary metabolism and salt stress alleviation in S. officinalis plants.

Proteins have been studied and applied to improve the stability of anthocyanins (ACNs), but the changes in the pH microenvironment during the preparation of steady-state systems are often ignored, and more attention is given to the stability of the system after preparation. In this study, we propose the \"anthocyanin front-end homeostasis strategy\", which involves designing a system can protect anthocyanins under acidic conditions so that more anthocyanin prototypes can be loaded inside the protein. Anthocyanins are encapsulated in liposomes (Lip) at pH 3.0 and combined with casein methacrylate (CSMA) to form Anthocyanin-loaded liposomes/CSMA hydrogel (Lip@ACNs/CSMA), with good physical properties and good blood compatibility. The system increased the hydrogen peroxide scavenging capacity by 1.16 mg Vc equiv./mg ACNs and the cellular antioxidant activity by 17.55 μM quercetin/100 mg ACNs, the photo and thermal storage stability increased by 36.50 % and 30.71 %, the digestive rate increased by 17.50 %, and the biological availability increased by 0.0049 mg/mL. This study designed a liposome casein hydrogel as an efficient front-end homeostatic anthocyanin loading system and provided a new approach for improving the stability of anthocyanins.