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Chalcone synthase (CHS) and chalcone isomerase (CHI) catalyze the first two committed steps of the flavonoid pathway that plays a pivotal role in the growth and reproduction of land plants, including UV protection, pigmentation, symbiotic nitrogen fixation, and pathogen resistance. Based on the obtained X-ray crystal structures of CHS, CHI, and chalcone isomerase-like protein (CHIL) from the same monocotyledon, Panicum virgatum, along with the results of the steady-state kinetics, spectroscopic/thermodynamic analyses, intermolecular interactions, and their effect on each catalytic step are proposed. In addition, PvCHI’s unique activity for both naringenin chalcone and isoliquiritigenin was analyzed, and the observed hierarchical activity for those type-I and -II substrates was explained with the intrinsic characteristics of the enzyme and two substrates. The structure of PvCHS complexed with naringenin supports uncompetitive inhibition. PvCHS displays intrinsic catalytic promiscuity, evident from the formation of p-coumaroyltriacetic acid lactone (CTAL) in addition to naringenin chalcone. In the presence of PvCHIL, conversion of p-coumaroyl-CoA to naringenin through PvCHS and PvCHI displayed ~400-fold increased Vmax with reduced formation of CTAL by 70%. Supporting this model, molecular docking, ITC (Isothermal Titration Calorimetry), and FRET (Fluorescence Resonance Energy Transfer) indicated that both PvCHI and PvCHIL interact with PvCHS in a non-competitive manner, indicating the plausible allosteric effect of naringenin on CHS. Significantly, the presence of naringenin increased the affinity between PvCHS and PvCHIL, whereas naringenin chalcone decreased the affinity, indicating a plausible feedback mechanism to minimize spontaneous incorrect stereoisomers. These are the first findings from a three-body system from the same species, indicating the importance of the macromolecular assembly of CHS-CHI-CHIL in determining the amount and type of flavonoids produced in plant cells.

FLH 13-11 is an F1 interspecific hybrid muscadine grape genotype that was developed to produce new anthocyanins for pigment color stability. This hybrid resulted from a cross between ‘Marsh’ (Vitis munsoniana) and ‘Magoon’ (V. rotundifolia) and has been cultivated for the wine and juice industry. This report characterizes anthocyanins produced in fully ripe berries and reveals a significant difference in total anthocyanin contents from two continuous cropping seasons. High-performance liquid chromatography with a diode array detector (HPLC-DAD) and HPLC–quadrupole time-of-flight tandem mass spectrometry (HPLC-qTOF-MS/MS) were used to profile anthocyanins in berries. The resulting data showed that fourteen anthocyanins were detected, six from 2011 and nine from 2012, with only one produced in both seasons. However, the anthocyanidin profiles of the berries were the same. Five anthocyanins were annotated as diglucosides of anthocyanidins based on MS/MS features, including delphinidin 3,5-diglucoside produced in both seasons, cyanidin 3,5-diglucoside mainly formed in 2011, petunidin 3,5-diglucoside, malvidin 3,5-diglucoside, and peonidin 3,5-glucoside only detected in 2012. Also, three anthocyanidin-diglucoside-like anthocyanins and three monoglucosides, including peonidin 3-glucoside, delphinidin 3-glucoside like, and pelargonidin 3-glucoside-like anthocyanins, were detected in 2011 and 2012, respectively. These results indicate that FLH 13-11 can produce both anthocyanidin-diglucosides and -monoglucosides, and their biosynthesis is closely dependent on cropping years.

To improve the control and detection methods of thiabendazole (TBZ), a fungicide and parasiticide often used in food products, we investigated the performance of the SERS technique applied to frozen blueberry fruits available on the market. TBZ-treated fruit extracts provided a multiplexed SERS feature, where the SERS bands of TBZ could be distinctly recorded among the characteristic anthocyanidins from blueberries. Quantitative SERS of TBZ in a concentration range from 20 µM to 0.2 µM has been achieved in solutions. However, quantitative multiplexed SERS is challenging due to the gradually increasing spectral background of polyphenols from extracts, which covers the TBZ signal with increasing concentration. The strategy proposed here was to employ food bentonite to filter a substantial amount of flavonoids to allow a higher SERS signal-to-background recording and TBZ recognition. Using bentonite, the LOD for SERS analysis of blueberry extracts provided a detection limit of 0.09 µM. From the relative intensity of the specific SERS bands as a function of concentration, we estimated the detection capability of TBZ to be 0.0001 mg/kg in blueberry extracts, which is two orders of magnitude lower than the maximum allowed by current regulations.

Numerous studies have provided evidence that diets rich in anthocyanins show a broad spectrum of health benefits. Anthocyanins in nature are usually found in the form of glycosides. Their aglycone forms are called anthocyanidins. The chemical structure of anthocyanins is based on the flavylium cation, but they differ in the position and number of substituents. However, the bioactives and foods that contain them are frequently treated as a uniform group of compounds exhibiting the same biological activity, without paying attention to the structural differences between individual anthocyanidins. The aim of this study was to find out how structural differences impact the biological activity of the six most common dietary anthocyanidins, i.e., delphinidin (Dp), petunidin (Pt), cyanidin (Cd), malvidin (Mv), pelargonidin (Pg) and peonidin (Po). The study concentrated on redox-related phenomena and compared the following parameters: antioxidant activity (measured using various methods: spectrophotometric tests (ABTS, DPPH), ORAC assay and CAA test (cellular antioxidant activity)), the ability to inhibit growth of human colon cancer cells (HT29; determined using MTT assay), and the ability of studied compounds to protect DNA from oxidative damage (comet assay). Based on the obtained results, the relationship between the structure of studied anthocyanidins and their biological activity was assessed. The obtained results revealed that the number and position of the hydroxyl and methoxy groups in the anthocyanidin structure strongly influenced not only the color of anthocyanidins but most of all their antioxidant and biological activities.

Purple Chinese cabbage (PCC) has become a new breeding trend due to its attractive color and high nutritional quality since it contains abundant anthocyanidins. With the aim of rapid evaluation of PCC anthocyanidins contents and screening of breeding materials, a fast quantitative detection method for anthocyanidins in PCC was established using Near Infrared Spectroscopy (NIR). The PCC samples were scanned by NIR, and the spectral data combined with the chemometric results of anthocyanidins contents obtained by high-performance liquid chromatography were processed to establish the prediction models. The content of cyanidin varied from 93.5 mg/kg to 12,802.4 mg/kg in PCC, while the other anthocyanidins were much lower. The developed NIR prediction models on the basis of partial least square regression with the preprocessing of no-scattering mode and the first-order derivative showed the best prediction performance: for cyanidin, the external correlation coefficient (RSQ) and standard error of cross-validation (SECV) of the calibration set were 0.965 and 693.004, respectively; for total anthocyanidins, the RSQ and SECV of the calibration set were 0.966 and 685.994, respectively. The established models were effective, and this NIR method, with the advantages of timesaving and convenience, could be applied in purple vegetable breeding practice.

Anthocyanins are a major group of plant pigments that have antioxidant activities. Pigments play a major role in human health and have attracted a lot of attention globally. Many factors affect anthocyanin yields, such as solvent type, incubation time, solvent-to-sample ratio, sample type, and temperature. The first parameter was tested, and the rest were considered constant in this experiment. A total of nine organic and water-based solvents (methanol and chloroform: methanol, acetone, ethanol, water) and their combinations were compared to extract anthocyanins from freshly-pureed strawberries. Solvents changed anthocyanin yield, color parameters, and profile. The color parameters of a* values lower than 30, L* values higher than 85, hue angle more than 40, and chroma less than 30 indicated some color degradation in strawberry anthocyanins. Therefore, the best solvents for anthocyanin assessment were methanol and methanol: water. The second-best solvent was the pH differential buffers. Other solvents such as ethanol, chloroform: methanol, water, and water-based solvents extracted considerable amounts of anthocyanins; however, they showed some degree of color degradation, evidenced by the color parameters. Acetone did not yield a stable extract which degraded over 48 h of storage at 4 °C. The extraction solvent determined the main anthocyanin of the anthocyanins profile. Pelargonidin was the major anthocyanin in chloroform: methanol solvent, while delphinidin was dominant in all other solvents.

Psb28 is a soluble protein in the photosystem II (PSII) complex, but its role in the drought stress response of wheat remains unclear. Here, we functionally characterized the TaPsb28 gene, which positively regulates drought tolerance in wheat. When the full-length 546-bp TaPsb28 cDNA was transferred into Arabidopsis thaliana, it was located in the guard cell chloroplast around the stroma. Overexpression of TaPsb28 conferred drought tolerance, as exhibited by the increases in the survival rate. Transgenic plants maintained lower MDA content and higher chlorophyll content by inducing chlorophyll synthase (ChlG) gene transcription. The content of abscisic acid (ABA) and zeatin increased significantly in wild-type (WT) plants under drought stress, and the transcriptional expression levels of RD22, dihydroflavonol 4-reductase (DFR) and anthocyanin reductase (ANR) genes were induced, thus enhancing the contents of endogenous cyanidin, delphinidin, and proanthocyanidins. However, in transgenic plants, although anthocyanins were further aggregated, the ABA increase was inhibited, zeatin was restored to the control level under drought stress, and stomatal closure was promoted. These findings indicate ABA and zeatin have opposite synergistic effects in the process of drought tolerance caused by TaPsb28 because only after the effect of zeatin is alleviated can ABA better play its role in promoting anthocyanin accumulation and stomatal closure, thus enhancing the drought tolerance of transgenic plants. The results suggest that overexpression of TaPsb28 exerts a positive role in the drought response by influencing the functional metabolism of endogenous hormones. The understanding acquired through the research laid a foundation for further in-depth investigation of the function of TaPsb28 in drought resistance in wheat, especially its relationship with anthocyanidin accumulation.

Anthocyanidins are found in nature mainly as pelargonidin, cyanidin, peonidin, delphinidin, petunidin, and malvidin derivatives. These compounds are found free or as glycoside derivatives which are responsible for the color (red, blue, and violet) of some foods and are responsible for attracting seed dispersers. They are grouped into 3-hydroxyanthocyanidins, 3-deoxyanthocyanidins (3D-anth), and O-methylated anthocyanidins. A new method was developed and validated to quantify 3D-anth in plant-rich extracts. To test the new method, Arrabidaea chica Verlot was selected as it is widely used in folk medicine, and it is rich in 3D-anth. The new method was developed by HPLC-DAD and expressed 3D-anth as carajurin content. Carajurin was chosen as the reference standard due to its role as a biological marker for the antileishmanial activity for A. chica. The selected method used a silica-based phenyl column, a mobile phase composed of potassium dihydrogen phosphate buffer, acetonitrile, and methanol, in a gradient elution mode and detection at 480 nm. The method reliability was confirmed by verifying selectivity, linearity, precision, recovery, and robustness. This method contributes to quality control and development of a possible active pharmaceutical ingredient from A. chica as well as it can be used to evaluate 3D-anth in plant extracts with chemical ecology interest.

Anthocyanins are water-soluble pigments characterized by various intense colors found in fruits and vegetables. Scientific studies have shown growing evidence to support their health benefits. Therefore, estimating the anthocyanin content in food is essential to identify the ideal analytical method. Moreover, due to the instability of plant anthocyanins, it is important to select and optimize their extraction, separation and qualitative and quantitative analysis, steps that are indispensable and important in their study. The present article reviews the latest procedures for extracting anthocyanins from various food matrices and analytical methods for their quantification. Therefore, various forms of preliminary treatments of samples for anthocyanin extraction, extraction procedures for various fruits, vegetables and cereals, purification of samples and quantification of anthocyanins are highlighted and evaluated. Using ultrasound-assisted extraction (UAE) might be effective for anthocyanin extraction and the Amberlite XAD-7HP method is the most effective for purifying anthocyanins. Combining the liquid chromatography (LC) method with electrospray ionization (ESI) and mass spectrometry (MS) or quadrupole time-of-flight (QTOF) with mass spectrometry (MS) better quantifies the anthocyanins in the food complex samples. Therefore, the extraction and separation of anthocyanins and their qualitative and quantitative analyses are essential steps in their research. As a result, the study concentrates on a detailed characterization of various qualitative and quantitative analytical methodologies, while briefly describing the main anthocyanin extraction processes.

Anthocyanidins, the aglycons of anthocyanins, are known, beyond their function in plants, also as compounds with a wide range of biological and pharmacological activities, including cytostatic effect against various cancer cells. The nature and position of the substituents in the flavylium cation is essential for such biological properties, as well as the equilibrium between the multistate of the different chemical species that are generated by the flavylium cation, including quinoidal base, hemiketal, and cis- and trans-chalcones. In this work, eight new flavylium derivatives were synthesized, characterized for confirmation of the structure by FT-IR and 2D-NMR, and investigated in vitro as possible cytostatic compounds against HCT116 and HepG2 cancer cells. The most active two compounds were explored for their halochromic properties that can influence the biological activity and subjected to molecular encapsulation in β-cyclodextrin derivatives in order to increase their solubility in water and bioavailability. The anticancer effect was influenced by the position (6-, 7-, or 8-) of the methoxy group in the β-ring of the methoxy-4′-hydroxy-3′-methoxyflavylium cation, while the study of the halochromic properties revealed the important role played by the chalcone species of the pH-dependent multistate in both the uncomplexed and inclusion complex forms of these anthocyanidins.

Flavonoids and proanthocyanidins (PACs) have been the subject of intense scientific investigations, both for their antioxidant properties and anti-adhesion activity against uropathogenic bacteria. We investigated the metabolomics and antioxidant capacity of SP4TM, a patent-pending formulation based on a mixture of plant extracts with a high content of bioactive PACs and other polyphenols. The total content of polyphenols (885.51 ± 14.19 mg/g), flavonoids (135.52 ± 8.98 mg/g), anthocyanins (54.84 ± 2.97 mg/g), and PACs (379.43 ± 12.44 mg/g) was quantified using UV-Vis assays. Use of HPLC-ESI-MS/MS revealed the presence of 5 flavanols (100.77 ± 3.90 mg g−1 d.wt), 11 flavonols (59.96 ± 1.83 mg g−1 d.wt), and 8 anthocyanins (46.96 ± 1.59 mg g−1 d.wt), whereas MALDI-TOF MS showed that SP4TM contains PACs with one or more type-A interflavan bonds at each degree of polymerization. Regarding antioxidant properties, LUCS technology on HepG2 cells evidenced the ability of SP4TM to neutralize intracellular free radicals, inhibit membrane lipid peroxidation, quench H2O2, and reduce free radicals mainly through chelating mechanism, as demonstrated by a higher FRAP value (2643.28 ± 39.86 mmol/g) compared with ABTS (139.92 ± 6.16 mmol/g) and DPPH (89.51 ± 3.91 mmol/g). Finally, the SP4TM type-A PAC content strongly prevented bacterial adhesion of P-fimbriated uropathogenic Escherichia coli (0.23 mg/mL). In conclusion, SP4TM has a strong antioxidant capacity involving multitarget mechanisms and is a potential supplement to fight urinary tract infections due to its ability to inhibit uropathogenic E. coli adhesion.

Background: Anthocyanidins are a kind of water-soluble flavonoids widely found in flowers and fruits of many plants. Although the beneficial effect of anthocyanidins in cancer prevention has been discussed, the value of anthocyanidins in lung cancer prevention requires further investigation. In this study, we aimed to explore the role of dietary anthocyanidins in the prevention of lung cancer in population-based prospective studies. Methods: Data of participants in this study were collected from the Prostate, Lung, Colorectal, and Ovarian Cancer Screening Trial. Hazard ratios (HRs) and 95% confidence intervals (CIs) were calculated in Cox proportional hazards regression for the association of dietary anthocyanidins and lung cancer risk. The dose-response relationship was explored between total anthocyanidins and the incidence of lung cancer. Results: A total of 97,993 participants were included in this study. The calculated HRs showed a trend that a higher quartile of total anthocyanidins indicated lower risk of lung cancer after adjusting for covariates (HRQ4vsQ1: 0.63; 95% CI: 0.55,0.73; p for trend < 0.001). A non-linear association between total anthocyanidins and lung cancer risk was found in the restricted cubic spline model. Conclusion: A protective association between dietary anthocyanidins and risk of lung cancer in Americans was investigated.

Mulberry (Morus spp., Moraceae) is an important economic crop plant and is rich in flavonoids and anthocyanidins in ripe fruits. Anthocyanins are glycosides of anthocyanidins. Flavanone 3-hydroxylase (F3H) catalyzes the conversion of naringenin into dihydroflavonols and is responsible for the biosynthesis of flavonols and anthocyanidins. In this study, MazsF3H was cloned and characterized from Morus atropurpurea var. Zhongshen 1. Conserved motif analysis based on alignment and phylogenetic analysis indicated that MazsF3H belonged to 2-oxoglutarate-dependent dioxygenase and MazsF3H clustered with F3Hs from other plants. MazsF3H was located in both nucleus and cytosol. MazsF3H was expressed in stems, leaves, stigmas and ovaries, except buds. F3H expression levels showed a positive and close relationship with anthocyanin content during the anthocyanin-rich fruit ripening process, while it showed a negative correlation with anthocyanin content in LvShenZi, whose fruits are white and would not experience anthocyanin accumulation during fruit ripening. Significantly different F3H expression levels were also found in different mulberry varieties that have quite different anthocyanin contents in ripe fruits. Overexpression MazsF3H in tobacco showed unexpected results, including decreased anthocyanin content. Down-regulation of F3H expression levels resulted in co-expression of the genes involved in anthocyanin biosynthesis and a significant decrease in anthocyanin content, but the change in total flavonoid content was subtle. Our results indicated that F3H may play quite different roles in different varieties that have quite different fruit colors. In addition, possible complex regulation of flavonoid biosynthesis should be further explored in some of the featured plant species.

As water-soluble flavonoid derivatives, anthocyanidins and anthocyanins are the plants pigments mostly rich in berries, pomegranate, grapes, and dark color fruits. Many bioactivity properties of these advantageous phytochemicals have been reported; among them, their significant abilities in the suppression of tumor cells are of the promising therapeutic features, which have recently attracted great attention. The prostate malignancy, is considered the 2nd fatal and the most distributed cancer type in men worldwide. The present study was designated to gather the preclinical and clinical studies evaluating potencies of anthocyanidins/anthocyanins for the treatment and prevention of this cancer type for the first time. In general, findings confirm that the anthocyanins (especifically cyanidin-3-O-glucoside) indicated higher activity against prostatic neoplasms compared to their correlated anthocyanidins (e.g., delphinidin); in which potent anti-inflammatory, apoptosis, and anti-proliferative activities were analyzed. Complementary anti-prostate cancer assessment of diverse naturally occurred anthocyanidins/anthocyanins and their synthetically optimized derivatives through preclinical experiments and eventually confirmed by clinical trials can promisingly lead to discover natural-based chemotherapeutic drug options.

Peptic ulcers are lesions that affect the gastrointestinal tract and that can be triggered by external factors such as alcohol use. This study investigated the gastroprotective role of two anthocyanidins, malvidin and cyanidin chloride, in an ethanol-induced gastric ulcer model in male and female mice (ovariectomized and supplemented with 17β-estradiol or not) and aimed to evaluate the effectiveness of anthocyanidins in preventing the formation of lesions and to identify the underlying mechanisms, while considering hormonal differences. Moreover, in silico comparative analysis was performed to predict the properties and biological behaviors of the molecules. We observed that the hormonal status did not interfere with the gastroprotective action of malvidin, although antioxidant mechanisms were modulated differently depending on sex. On the other hand, cyanidin showed gastroprotective activity at different doses, demonstrating that, for the same experimental model, there is a need to adjust the effective dose depending on sex. In silico analysis showed that, despite being structurally similar, the interaction with receptors and target proteins in this study (myeloperoxidase, superoxide dismutase, catalase, and reduced glutathione) differed between the two molecules, which explains the difference observed in in vivo treatments.

Until now, several studies have looked at the issue of anthocyanin and cancer, namely the preventive and inhibitory effects of anthocyanins, as well as the underlying molecular processes. However, no targeted review is available regarding the anticarcinogenic effects of delphinidin and its glycosides on various cancers and their plausible molecular mechanisms. Considerable evidence shows significant anticancer properties of delphinidin-rich preparations and delphinidin alone both in vitro and in vivo. This review covers the in vitro and preclinical implications of delphinidin-mediated cell protection and cancer prevention; thus, we strongly recommend that delphinidin-rich preparations be further investigated as potential functional food, dietary antioxidant supplements, and natural health products targeting specific chronic diseases, including cancer. In addition to in vitro investigations, future research should focus on more animal and human studies to determine the true potential of delphinidin.

Natural pigments, including carotenoids, flavonoids and anthocyanidins, determine the attractive color of fruits. These natural pigments are essential secondary metabolites, which play multiple roles in the whole life cycle of plants and are characterized by powerful antioxidant activity. After decades of research and development, multiple benefits of these natural pigments to human health have been explored and recognized and have shown bright application prospects in food, medicine, cosmetics and other industries. In this paper, the research progress of natural fruit pigments in recent years was reviewed, including the structural characteristics and classification, distribution in fruits and analysis methods, biosynthetic process, antioxidant capacity and mechanism, bioaccessibility and bioavailability, and health benefits. Overall, this paper summarizes the recent advances in antioxidant activity and other biological functions of natural fruit pigments, which aims to provide guidance for future research.

In the past century, plant biostimulants have been increasingly used in agriculture as innovative and sustainable practice. Plant biostimulants have been mainly investigated as potential agents able to mitigate abiotic stress. However, few information is available about their ability to influence fruit quality or change fruit phytochemical composition. In particular, very little is known about their effects on anthocyanin synthesis and accumulation. Due to the increasing demand of consumers for healthier foods with high nutraceutical values, this review tries to fill the gap between anthocyanin content and biostimulant application. Here, we elucidate the chemical structure, biosynthetic pathway, plant distribution, and physiological role of anthocyanins in plants. Moreover, we discuss the potential implications for human health derived from the consumption of foods rich in these molecules. Finally, we report on literature data concerning the changes in anthocyanin content and profile after the application of biostimulant products on the most common anthocyanin-containing foods.

3-Bromopyruvic acid (3-BP) is a promising anticancer compound. Two ovary cancer (OC) cell lines, PEO1 and SKOV3, showed relatively high sensitivity to 3-BP (half maximal inhibitory concentration (IC50) of 18.7 and 40.5 µM, respectively). However, the further sensitization of OC cells to 3-BP would be desirable. Delphinidin (D) has been reported to be cytotoxic for cancer cell lines. We found that D was the most toxic for PEO1 and SKOV3 cells from among several flavonoids tested. The combined action of 3-BP and D was mostly synergistic in PEO1 cells and mostly weakly antagonistic in SKOV3 cells. The viability of MRC-5 fibroblasts was not affected by both compounds at concentrations of up to 100 µM. The combined action of 3-BP and D decreased the level of ATP and of dihydroethidium (DHE)-detectable reactive oxygen species (ROS), cellular mobility and cell staining with phalloidin and Mitotracker Red in both cell lines but increased the 2’,7’-dichlorofluorescein (DCFDA)-detectable ROS level and decreased the mitochondrial membrane potential and mitochondrial mass only in PEO1 cells. The glutathione level was increased by 3-BP+D only in SKOV3 cells. These differences may contribute to the lower sensitivity of SKOV3 cells to 3-BP+D. Our results point to the possibility of sensitization of at least some OC cells to 3-BP by D.

Wine is one of the most consumed beverages around the world. It is composed of alcohols, sugars, acids, minerals, proteins and other compounds, such as organic acids and volatile and phenolic compounds (also called polyphenols). Polyphenols have been shown to be highly related to both (i) wine quality (color, flavor, and taste) and (ii) health-promoting properties (antioxidant and cardioprotective among others). Polyphenols can be grouped into two big families: (i) Flavonoids, including anthocyanidins, flavonols, flavanols, hydrolysable and condensed tannins, flavanones, flavones and chalcones; and (ii) Non-flavonoids, including hydroxycinnamic acids, hydroxybenzoic acids, stilbenes, tyrosol and hydroxytyrosol. Each group affects in some way the different properties of wine to a greater or a lesser extent. For that reason, the phenolic composition can be managed to obtain singular wines with specific, desirable characteristics. The current review presents a summary of the ways in which the phenolic composition of wine can be modulated, including (a) invariable factors such as variety, field management or climatic conditions; (b) pre-fermentative strategies such as maceration, thermovinification and pulsed electric field; (c) fermentative strategies such as the use of different yeasts and bacteria; and (d) post-fermentative strategies such as maceration, fining agents and aging. Finally, the different extraction methods and analytical techniques used for polyphenol detection and quantification have been also reviewed.

Anthocyanins are polyphenol compounds that render various hues of pink, red, purple, and blue in flowers, vegetables, and fruits. Anthocyanins also play significant roles in plant propagation, ecophysiology, and plant defense mechanisms. Structurally, anthocyanins are anthocyanidins modified by sugars and acyl acids. Anthocyanin colors are susceptible to pH, light, temperatures, and metal ions. The stability of anthocyanins is controlled by various factors, including inter and intramolecular complexations. Chromatographic and spectrometric methods have been extensively used for the extraction, isolation, and identification of anthocyanins. Anthocyanins play a major role in the pharmaceutical; nutraceutical; and food coloring, flavoring, and preserving industries. Research in these areas has not satisfied the urge for natural and sustainable colors and supplemental products. The lability of anthocyanins under various formulated conditions is the primary reason for this delay. New gene editing technologies to modify anthocyanin structures in vivo and the structural modification of anthocyanin via semi-synthetic methods offer new opportunities in this area. This review focusses on the biogenetics of anthocyanins; their colors, structural modifications, and stability; their various applications in human health and welfare; and advances in the field.

Arrabidaea chica Verlot (crajiru) is a plant used in folk medicine as an astringent, anti-inflammatory, wound healing and to treat fungal and viral diseases such as measles chickenpox and herpes. Arrabidaea chica has several morphotypes recognized but little is known about its chemical variability. In the present study the anthocyanidin profile of A. chica morphotypes collected in two seasons (summer and winter) have been examined and their activity against Leishmania infection compared. High-performance liquid chromatography coupled to a diode-array detector (HPLC-DAD-UV) and by tandem mass spectrometry with electrospray ionization (ESI-MS/MS) were used for anthocyanidin separation and identification. Antileishmanial activity was measured against promastigote forms of Leishmania amazonensis. Multivariate analysis, principal component analysis (PCA) and Pearson’s correlation were performed to classify morphotypes accordingly to their anthocyanidin profile. The presence of 6,7,3′,4′-tetrahydroxy-5-methoxyflavylium (3′-hydroxy-carajurone) (1), carajurone (2), 6,7,3′-trihydroxy-5,4′-dimethoxy-flavylium (3′-hydroxy-carajurin) (3) and carajurin (4), and three unidentified anthocyanidins were detected. Two different groups were recognized: group I containing 3′-hydroxy-carajurone; and group II with high content of carajurin. Among anthocyanidins identified in the extracts, only carajurin showed significant statistical correlation (p = 0.030) with activity against L. amazonensis. Carajurin could thus be considered as a pharmacological marker for the antileishmanial potential of the species.

Anthocyanins are a class of water-soluble flavonoids widely present in fruits and vegetables. Dietary sources of anthocyanins include red and purple berries, grapes, apples, plums, cabbage, or foods containing high levels of natural colorants. Cyanidin, delphinidin, malvidin, peonidin, petunidin, and pelargonidin are the six common anthocyanidins. Following consumption, anthocyanin, absorption occurs along the gastrointestinal tract, the distal lower bowel being the place where most of the absorption and metabolism occurs. In the intestine, anthocyanins first undergo extensive microbial catabolism followed by absorption and human phase II metabolism. This produces hybrid microbial–human metabolites which are absorbed and subsequently increase the bioavailability of anthocyanins. Health benefits of anthocyanins have been widely described, especially in the prevention of diseases associated with oxidative stress, such as cardiovascular and neurodegenerative diseases. Furthermore, recent evidence suggests that health-promoting effects attributed to anthocyanins may also be related to modulation of gut microbiota. In this paper we attempt to provide a comprehensive view of the state-of-the-art literature on anthocyanins, summarizing recent findings on their chemistry, biosynthesis, nutritional value and on their effects on human health.

Alzheimer’s disease (AD) is a progressive neurodegenerative disorder. To fight the disease, natural products, including mulberry, with antioxidant activities and inhibitory activities against key enzymes (acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and beta-secretase 1 (BACE-1)) are of interest. However, even in the same cultivars, mulberry trees grown in different populated locations might possess disparate amounts of phytochemical profiles, leading to dissimilar health properties, which cause problems when comparing different cultivars of mulberry. Therefore, this study aimed to comparatively investigate the phytochemicals, antioxidant activities, and inhibitory activities against AChE, BChE, and BACE-1, of twenty-seven Morus spp. cultivated in the same planting area in Thailand. The results suggested that Morus fruit samples were rich in phenolics, especially cyanidin, kuromanin, and keracyanin. Besides, the aqueous Morus fruit extracts exhibited antioxidant activities, both in single electron transfer (SET) and hydrogen atom transfer (HAT) mechanisms, while strong inhibitory activities against AD key enzymes were observed. Interestingly, among the twenty-seven Morus spp., Morus sp. code SKSM 810191 with high phytochemicals, antioxidant activities and in vitro anti-AD properties is a promising cultivar for further developed as a potential mulberry resource with health benefits against AD.

Alzheimer’s disease (AD) is the most common form of dementia, characterized by chronic neuron loss and cognitive problems. Aggregated amyloid beta (Aβ) peptides, a product of cleaved amyloid precursor protein (APP) by beta-secretase 1 (BACE-1), have been indicated for the progressive pathogenesis of AD. Currently, screening for anti-AD compounds in foodstuffs is increasing, with promising results. Hence, the purpose of this study was to investigate the extraction conditions, phytochemical contents, and anti-AD properties, targeting Aβ peptides of Morus cf. nigra ‘Chiang Mai’ (MNCM) both in vitro and in vivo. Data showed that the aqueous extract of MNCM contained high amounts of cyanidin, keracyanin, and kuromanin as anthocyanidin and anthocyanins. The extract also strongly inhibited cholinesterases and BACE-1 in vitro. Moreover, MNCM extract prevented Aβ-induced neurotoxicity and promoted neurite outgrowth in neuronal cells. Interestingly, MNCM extract reduced Aβ1–42 peptides and improved locomotory coordination of Drosophila co-expressing human APP and BACE-1, specifically in the brain. These findings suggest that MNCM may be useful as an AD preventive agent by targeting Aβ formation.

Recent in vitro and in vivo studies on anthocyanins confirmed numerous health-promoting effects in humans. Daily anthocyanin intake can be estimated via food databases, but the amount absorbed by the organism still remains uncertain because anthocyanin bioavailability is yet to be elucidated in its entirety. For this purpose, suitable and validated methods of sample preparation and analysis are required. Therefore, a sample preparation method for anthocyanin metabolite analysis in plasma was successfully established and validated. The validation yielded acceptable results for the anthocyanins in terms of recovery (54−108%) and precision (coefficient of variation (CV) < 15%). The UHPLC-MS method used in the consecutive reaction monitoring (CRM) mode was sufficiently sensitive, resulting in limits of detection

Strawberries and blueberries are two of the most commonly consumed berries. Berries, in general, are characterized by their highly nutritive compounds, including minerals, vitamins, fatty acids, and dietary fiber, as well as their high content and wide diversity of bioactive compounds, such as phenolic compounds and organic acids. These bioactive compounds have been associated with protective effects against chronic diseases, such as cardiovascular disease, cancer, Alzheimer’s and other disorders. In this paper 16 human intervention studies investigating the beneficial health effects of dietary strawberry or blueberry consumption on inflammation, cardiovascular disease or cognitive function and mental health are reviewed.

Purple Chinese cabbage (PCC) has become a new breeding trend due to its attractive color and high nutritional quality since it contains abundant anthocyanidins. With the aim of rapid evaluation of PCC anthocyanidins contents and screening of breeding materials, a fast quantitative detection method for anthocyanidins in PCC was established using Near Infrared Spectroscopy (NIR). The PCC samples were scanned by NIR, and the spectral data combined with the chemometric results of anthocyanidins contents obtained by high-performance liquid chromatography were processed to establish the prediction models. The content of cyanidin varied from 93.5 mg/kg to 12,802.4 mg/kg in PCC, while the other anthocyanidins were much lower. The developed NIR prediction models on the basis of partial least square regression with the preprocessing of no-scattering mode and the first-order derivative showed the best prediction performance: for cyanidin, the external correlation coefficient (RSQ) and standard error of cross-validation (SECV) of the calibration set were 0.965 and 693.004, respectively; for total anthocyanidins, the RSQ and SECV of the calibration set were 0.966 and 685.994, respectively. The established models were effective, and this NIR method, with the advantages of timesaving and convenience, could be applied in purple vegetable breeding practice.

This paper summarizes the information on the occurrence of phenolic compounds in apple (Malus x domestica Borkh.) fruit and juice, with special reference to their health related properties. As phytochemical molecules belonging to polyphenols are numerous, we will focus on the main apples phenolic compounds with special reference to changes induced by apple cultivar, breeding approaches, fruit postharvest and transformation into juice.

The grains and sprouts of colored wheat genotypes (having blue, purple and yellow colored grains) contain specific anthocyanidins, such as pelargonidin and cyanidin derivatives, that produce beneficial health effects. The objective of the presented study is to compare the antioxidant capacity and contents of bioactive phytochemicals in grains and sprouts of wheat genotypes that differ in grain color. The methods α, α-diphenyl-β-picrylhydrazyl (DPPH) and 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) scavenging activities, together with spectrophotometrical and high-performance thin-layer chromatography (HPTLC) methods, were used to study the presence of total phenolics, flavonoids, anthocyanins and anthocyanidins (pelargonidin, peonidin, cyanidin, delphinidin) content. It was predicted that the sprouts of all colored wheat genotypes would have significantly higher total flavonoids, total phenolics, anthocyanidin levels and antioxidant activity than the grains. The correlation results between antioxidant activity and contents of bioactive phytochemicals in grains and sprouts of colored wheat genotypes have shown a high correlation for cyanidin and pelargonidin, especially in grains, as well as quercetin in sprouts. It was found that total anthocyanin, quercetin and pelargonidin contents were significantly higher in the sprouts of the purple wheat genotypes than in the blue or yellow wheat genotypes. Delphinidin was detected at a higher level in the grains than in the sprouts of the blue wheat genotypes. Peonidin was present at very low quantities in the grains of all colored wheat genotypes. The sprouts of the purple wheat genotypes, among the colored wheat genotypes, had the highest pelargonidin, cyanidin and quercetin contents and, therefore, can be a promising source for functional food use.

Blueberry juice processing includes multiple steps and each one affects the chemical composition of the berries, including thermal degradation of anthocyanins. Not-from-concentrate juice was made by heating and enzyme processing blueberries before pressing, followed by ultrafiltration and pasteurization. Using LC–MS/MS, major and minor anthocyanins were identified and semi-quantified at various steps through the process. Ten anthocyanins were identified, including 5 arabinoside and 5 pyrannoside anthocyanins. Three minor anthocyanins were also identified, which apparently have not been previously reported in rabbiteye blueberries. These were delphinidin-3-(p-coumaroyl-glucoside), cyanidin-3-(p-coumaroyl-glucoside), and petunidin-3-(p-coumaroyl-glucoside). Delphinidin-3-(p-coumaroyl-glucoside) significantly increased 50% after pressing. The five known anthocyanidins—cyanidin, delphinidin, malvidin, peonidin, and petunidin—were also quantitated using UPLC–UV. Raw berries and press cake contained the highest anthocyanidin contents and contribute to the value and interest of press cake for use in other food and non-food products. Losses of 75.7% after pressing and 12% after pasteurization were determined for anthocyanidins during not-from-concentrate juice processing.

Anthocyanins are a major group of plant pigments that have antioxidant activities. Pigments play a major role in human health and have attracted a lot of attention globally. Many factors affect anthocyanin yields, such as solvent type, incubation time, solvent-to-sample ratio, sample type, and temperature. The first parameter was tested, and the rest were considered constant in this experiment. A total of nine organic and water-based solvents (methanol and chloroform: methanol, acetone, ethanol, water) and their combinations were compared to extract anthocyanins from freshly-pureed strawberries. Solvents changed anthocyanin yield, color parameters, and profile. The color parameters of a* values lower than 30, L* values higher than 85, hue angle more than 40, and chroma less than 30 indicated some color degradation in strawberry anthocyanins. Therefore, the best solvents for anthocyanin assessment were methanol and methanol: water. The second-best solvent was the pH differential buffers. Other solvents such as ethanol, chloroform: methanol, water, and water-based solvents extracted considerable amounts of anthocyanins; however, they showed some degree of color degradation, evidenced by the color parameters. Acetone did not yield a stable extract which degraded over 48 h of storage at 4 °C. The extraction solvent determined the main anthocyanin of the anthocyanins profile. Pelargonidin was the major anthocyanin in chloroform: methanol solvent, while delphinidin was dominant in all other solvents.

Anthocyanidins are found in nature mainly as pelargonidin, cyanidin, peonidin, delphinidin, petunidin, and malvidin derivatives. These compounds are found free or as glycoside derivatives which are responsible for the color (red, blue, and violet) of some foods and are responsible for attracting seed dispersers. They are grouped into 3-hydroxyanthocyanidins, 3-deoxyanthocyanidins (3D-anth), and O -methylated anthocyanidins. A new method was developed and validated to quantify 3D-anth in plant-rich extracts. To test the new method, Arrabidaea chica Verlot was selected as it is widely used in folk medicine, and it is rich in 3D-anth. The new method was developed by HPLC-DAD and expressed 3D-anth as carajurin content. Carajurin was chosen as the reference standard due to its role as a biological marker for the antileishmanial activity for A. chica . The selected method used a silica-based phenyl column, a mobile phase composed of potassium dihydrogen phosphate buffer, acetonitrile, and methanol, in a gradient elution mode and detection at 480 nm. The method reliability was confirmed by verifying selectivity, linearity, precision, recovery, and robustness. This method contributes to quality control and development of a possible active pharmaceutical ingredient from A. chica as well as it can be used to evaluate 3D-anth in plant extracts with chemical ecology interest.

Flavonoids and proanthocyanidins (PACs) have been the subject of intense scientific investigations, both for their antioxidant properties and anti-adhesion activity against uropathogenic bacteria. We investigated the metabolomics and antioxidant capacity of SP4 TM , a patent-pending formulation based on a mixture of plant extracts with a high content of bioactive PACs and other polyphenols. The total content of polyphenols (885.51 ± 14.19 mg/g), flavonoids (135.52 ± 8.98 mg/g), anthocyanins (54.84 ± 2.97 mg/g), and PACs (379.43 ± 12.44 mg/g) was quantified using UV-Vis assays. Use of HPLC-ESI-MS/MS revealed the presence of 5 flavanols (100.77 ± 3.90 mg g -1 d.wt), 11 flavonols (59.96 ± 1.83 mg g -1 d.wt), and 8 anthocyanins (46.96 ± 1.59 mg g -1 d.wt), whereas MALDI-TOF MS showed that SP4 TM contains PACs with one or more type-A interflavan bonds at each degree of polymerization. Regarding antioxidant properties, LUCS technology on HepG2 cells evidenced the ability of SP4 TM to neutralize intracellular free radicals, inhibit membrane lipid peroxidation, quench H 2 O 2 , and reduce free radicals mainly through chelating mechanism, as demonstrated by a higher FRAP value (2643.28 ± 39.86 mmol/g) compared with ABTS (139.92 ± 6.16 mmol/g) and DPPH (89.51 ± 3.91 mmol/g). Finally, the SP4 TM type-A PAC content strongly prevented bacterial adhesion of P-fimbriated uropathogenic Escherichia coli (0.23 mg/mL). In conclusion, SP4 TM has a strong antioxidant capacity involving multitarget mechanisms and is a potential supplement to fight urinary tract infections due to its ability to inhibit uropathogenic E. coli adhesion.