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Anthocyanins (ACNs) are plant secondary metabolites from the flavonoid family. Red to blue fruits are major dietary sources of ACNs (up to 1 g/100 g FW), being cyanidin-3-O-glucoside (Cy3G) one of the most widely distributed. Cy3G confers a red hue to fruits, but its content in raspberries and strawberries is low. It has a good radical scavenging capacity (RSC) against superoxide but not hydroxyl radicals, and its oxidative potential is pH-dependent (58 mV/pH unit). After intake, Cy3G can be metabolized (phases I, II) by oral epithelial cells, absorbed by the gastric epithelium (1%–10%) and it is gut-transformed (phase II & microbial metabolism), reaching the bloodstream (<1%) and urine (about 0.02%) in low amounts. In humans and Caco-2 cells, Cy3G’s major metabolites are protocatechuic acid and phloroglucinaldehyde which are also subjected to entero-hepatic recycling, although caffeic acid and peonidin-3-glucoside seem to be strictly produced in the large bowel and renal tissues. Solid evidence supports Cy3G’s bioactivity as DNA-RSC, gastro protective, anti-inflammatory, anti-thrombotic chemo-preventive and as an epigenetic factor, exerting protection against Helicobacter pylori infection, age-related diseases, type 2 diabetes, cardiovascular disease, metabolic syndrome and oral cancer. Most relevant mechanisms include RSC, epigenetic action, competitive protein-binding and enzyme inhibition. These and other novel aspects on Cy3G’s physical-chemistry, foodomics, and health effects are discussed.

The flowers of twenty-three cultivars of Dendranthema grandiflorum Ramat. were investigated to determine anthocyanin and carotenoid levels and to confirm the effects of the pigments on the flower colors using high-performance liquid chromatography (HPLC) and electrospray ionization-mass spectrometry (ESI-MS). The cultivars contained the anthocyanins cyanidin 3-glucoside (C3g) and cyanidin 3-(3ʺ-malonoyl) glucoside (C3mg) and the following carotenoids: lutein, zeaxanthin, β-cryptoxanthin, 13-cis-β-carotene, α-carotene, trans-β-carotene, and 9-cis-β-carotene. The cultivar “Magic” showed the greatest accumulation of total and individual anthocyanins, including C3g and C3gm. On the other hand, the highest level of lutein and zeaxanthin was noted in the cultivar “Il Weol”. The cultivar “Anastasia” contained the highest amount of carotenoids such as trans-β-carotene, 9-cis-β-carotene, and 13-cis-β-carotene. The highest accumulation of β-cryptoxanthin and α-carotene was noted in the cultivar “Anastasia” and “Il Weol”. Our results suggested that ‘Magic”, “Angel” and “Relance’ had high amounts of anthocyanins and showed a wide range of red and purple colors in their petals, whereas “Il Weol’, “Popcorn Ball’ and “Anastasia” produced higher carotenoid contents and displayed yellow or green petal colors. Interestingly, “Green Pang Pang”, which contained a high level of anthocyanins and a medium level of carotenoids, showed the deep green colored petals. “Kastelli”, had high level of carotenoids as well as a medium level of anthocyanins and showed orange and red colored petals. It was concluded that each pigment is responsible for the petal’s colors and the compositions of the pigments affect their flower colors and that the cultivars could be a good source for pharmaceutical, floriculture, and pigment industries.

Raspberry fruits are a valuable source of bioactive compounds. The study used the modification of the substrate (coconut fibre), consisting of the use of various organic and mineral additives, in the soilless cultivation of raspberries. The additives influenced the biosynthesis of bioactive compounds in the raspberry fruits by modifying the sorption properties and the abundance of the substrate. The influence of the additives on the content of polyphenols was determined as well as their profile (UPLC-MS), antioxidant potential (ABTS), vitamin C content, and the activity of selected enzymes that are markers of stress and resistance to abiotic factors. In the study, a significant effect of these additives was observed on the biosynthesis of polyphenols in raspberry fruit. The highest increase in the content of these compounds in relation to the control sample (substrate—100% coconut fibre), namely 37.7%, was recorded in the case of fruit produced on coconut substrate enriched with sheep wool. These fruits were also characterised by a significantly different profile of these compounds. These changes were caused by readily available ammonium nitrogen and free amino acids in the decomposition of proteins contained in the sheep wool. This was confirmed by the recorded content of chlorophyll SPAD in the plant leaves and the activity of selected enzymes, which proves a low level of stress and good condition of the plants.

We used blue berries of bilberry (Vaccinium myrtillus) to comprehensively characterise flavonoid-regulating R2R3 MYBs, which revealed a new type of co-regulation in anthocyanin biosynthesis between members of MYBA-, MYBPA1- and MYBPA2-subgroups. VmMYBA1, VmMYBPA1.1 and VmMYBPA2.2 expression was elevated at berry ripening and by abscisic acid treatment. Additionally, VmMYBA1 and VmMYBPA1.1 expression was strongly downregulated in a white berry mutant. Complementation and transient overexpression assays confirmed VmMYBA1 and VmMYBA2 to induce anthocyanin accumulation. Promoter activation assays showed that VmMYBA1, VmMYBPA1.1 and VmMYBPA2.2 had similar activity towards dihydroflavonol 4-reductase (DFR) and anthocyanidin synthase (ANS), but differential regulation activity for UDP-glucose flavonoid 3-O-glucosyltransferase (UFGT) and flavonoid 3′5′-hydroxylase (F3′5′H) promoters. Silencing of VmMYBPA1.1 in berries led to the downregulation of key anthocyanin and delphinidin biosynthesis genes. Functional analyses of other MYBPA regulators, and a member of novel MYBPA3 subgroup, associated them with proanthocyanidin biosynthesis and F3′5′H expression. The existence of 18 flavonoid-regulating MYBs indicated gene duplication, which may have enabled functional diversification among MYBA, MYBPA1 and MYBPA2 subgroups. Our results provide new insights into the intricate regulation of the complex anthocyanin profile found in blue-coloured berries involving regulation of both cyanidin and delphinidin branches.

The C-S-A gene system determines rice hull pigmentation. A conserved color-producing model reveals the independent origin and evolution of the anthocyanin biosynthesis pathway in rice. Abstract Floral organs in rice (Oryza sativa) can be purple, brown, or red in color due to the accumulation of flavonoids, but the molecular mechanism underlying specific organ pigmentation is not clear. Here, we propose a C-S-A gene model for rice hull pigmentation and characterize it through genetic, molecular, and metabolomic approaches. Furthermore, we conducted phylogenetic studies to reveal the evolution of rice color. In this gene system, C1 encodes a R2R3-MYB transcription factor and acts as a color-producing gene, and S1 encodes a bHLH protein that functions in a tissue-specific manner. C1 interacts with S1 and activates expression of A1, which encodes a dihydroflavonol reductase. As a consequence, the hull is purple where functional A1 participation leads to high accumulation of cyanidin 3-O-glucoside. Loss of function of A1 leads to a brown hull color due to accumulation of flavonoids such as hesperetin 5-O-glucoside, rutin, and delphinidin 3-O-rutinoside. This shows a different evolutionary pathway of rice color in japonica and indica, supporting independent origin of cultivars in each subspecies. Our findings provide a complete perspective on the gene regulation network of rice color formation and supply the theoretical basis for extended application of this beneficial trait.

Mulberry fruits are known as rich sources of anthocyanins and are consumed in syrup form after the addition of sugar and acid; however, there is little information on the anthocyanin composition and antioxidant activity of mulberries of different cultivars and their changes during processing. To address this, the antioxidant activity and anthocyanin composition of 12 cultivar mulberry fruit cultivars were investigated by high-performance liquid chromatography and ultra-high-performance liquid chromatography coupled with electrospray ionization/quadrupole time-of-flight. Additionally, different quantities of citric acid were used to evaluate antioxidant activities and anthocyanin composition of mulberry syrup. Sixteen anthocyanins were identified in mulberry fruits using accurate mass spectrometry. Several anthocyanins were tentatively identified for the first time in mulberry fruits and include: malvidin hexoside, cyanidin malonyl hexose hexoside, cyanidin pentoside, cyanidin malonyl hexoside, petunidin deoxyhexose hexoside, and cyanidin deoxyhexoside. The major anthocyanin in mulberries was cyanidin-3-O-glucoside, followed by cyanidin-3-O-rutinoside. Morus Alba L. Iksu showed the highest cyanidin-3-O-glucoside content (8.65 mg/g dry weight) among 12 mulberry fruit cultivars. As citric acid levels increased, mulberry syrup showed significantly higher antioxidant activity (p < 0.05).

Alzheimer’s disease (AD), due to its spread, has become a global health priority, and is characterized by senile dementia and progressive disability. The main cause of AD and other neurodegenerations (Huntington, Parkinson, Amyotrophic Lateral Sclerosis) are aggregated protein accumulation and oxidative damage. Recent research on secondary metabolites of plants such as polyphenols demonstrated that they may slow the progression of AD. The flavonoids’ mechanism of action in AD involved the inhibition of acetylcholinesterase, butyrylcholinesterase, Tau protein aggregation, β-secretase, oxidative stress, inflammation, and apoptosis through modulation of signaling pathways which are implicated in cognitive and neuroprotective functions, such as ERK, PI3-kinase/Akt, NFKB, MAPKs, and endogenous antioxidant enzymatic systems. This review focuses on flavonoids and their role in AD, in terms of therapeutic potentiality for human health, antioxidant potential, and specific AD molecular targets.

Anthocyanins are natural pigments abundant in various fruits and berries that are involved in the prevention of various chronic diseases. Their low concentrations in plasma and urine are explained in part by their complex chemistry and the formation of still uncharacterised metabolites. The aim of the present study was to follow the distribution of anthocyanins in the body using 14C-labelled cyanidin 3-O-glucoside (Cy3G) fed by gavage to mice. After the administration of 22·2 kBq 14C-Cy3G (0·93 mg), radioactivity was detected in most organs tested over the following 24 h with a peak observed in inner tissues at 3 h. The major fraction of the radioactivity (44·5 %) was found in the faeces collected 24 h after ingestion. At 3 h after oral administration of 141 kBq 14C-Cy3G (4·76 mg), most of the radioactivity (87·9 % of intake) was recovered in the gastrointestinal (GI) tract, especially in the small intestine (50·7 %) and the caecum (23 %). At this time, 3·3 % of the radioactivity was detected in urine. There was minimal accumulation (0·76 %) of radioactivity in tissues outside the GI tract. Distribution of radioactivity varied among organs, with liver, gallbladder and kidneys showing the highest radioactivity. Taken as a whole, these results show that Cy3G is poorly absorbed in the mouse.

Wild and cultivated rice show a significant difference in anthocyanin biosynthesis in the leaf. The regulation system of anthocyanin biosynthesis in rice leaf and the causal mechanism of the difference in this biosynthesis between wild and cultivated rice remain largely unknown. In this study, a genome-wide association study and transcriptome analysis were performed to identify the determinant factors and dissect the regulatory system for anthocyanin biosynthesis in rice leaves. OsC1, OsRb and OsDFR were identified as the determinants of anthocyanin biosynthesis in rice leaves. Artificial selection of certain null mutations of OsC1 and OsRb was the main causal mechanism underlying the loss of anthocyanin pigmentation in most cultivated rice. OsP1 and the MYB-bHLH-WD40 complexes regulate anthocyanin biosynthetic genes in rice leaves with partial functional overlap. OsP1 specifically activates upstream biosynthetic genes (OsCHS, OsCHI and OsF3’H) for anthocyanin biosynthesis, whereas the ternary MYB-bHLH-WD40 complex activates all anthocyanin biosynthetic genes including OsCHS, OsCHI, OsF3’H, OsF3H, OsDFR and OsANS. OsC1 and OsRb are tissue-specific regulators that do not influence anthocyanin biosynthesis in the pericarp. Our results reveal the determinant factors, regulatory system and domestication of anthocyanin biosynthesis in rice leaves, and show the potential of engineering anthocyanin biosynthesis in rice.

Butterfly pea flower have great sensory attraction, but they have not yet been used widely in Vietnam. Extracts of butterfly pea flowers can be used conveniently as a natural blue colorant for food products. In this study, the identification of anthocyanin compounds in butterfly pea flowers was performed by UPLC coupled with a UV and Mass spectrometer instrument. Positive and negative ion electrospray MS/MS chromatograms and spectra of the anthocyanin compounds were determined. By analyzing the chromatograms and spectra for each ion, five anthocyanins were identified in the butterfly pea flower extract; these were delphinidin-3-(6″-p-coumaroyl)-rutinoside, cyanidin 3-(6″-p-coumaroyl)-rutinoside, delphinidin-3-(p-coumaroyl) glucose in both cis- and trans- isomers, cyanidin-3-(p-coumaroyl-glucoside) and delphinidin-3-pyranoside. Additionally, based on their intensity, it was determined that cyanidin-3-(p-coumaroyl-glucoside) was the most abundant anthocyanin, followed by cyanidin 3-(6″-p-coumaroyl)-rutinoside, delphinidin-3-(p-coumaroyl-glucoside), delphinidin-3-(6″-p-coumaroyl)-rutinoside and delphinidin-3-pyranoside. In this study, cyanidin derivatives were discovered in butterfly pea flower extract, where these compounds had not been detected in previous studies.