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Background The bast fiber crop ramie can be used as high-quality forage resources, especially in tropical or subtropical region where there is lack of high-quality protein feed. Hongxuan No.1 (HX_1) is a unique ramie variety with a light reddish brown leaf color, which is obviously different from elite cultivar, Zhongzhu No.1 (ZZ_1, green leaf). While, the regulatory mechanism of color difference or secondary metaboliates synthesis between these two varieties have not been studied. Results In this study, phenotypic, transcriptomic and metabolomic analysis of HX_1 and ZZ_1 were conducted to elucidate the mechanism of leaf color formation. Chromaticity value and pigment content measuring showed that anthocyanin was the main metabolites imparting the different leaf color phenotype between the two varieties. Based on LC/MS, at least 14 anthocyanins were identified in leaves of HX_1 and ZZ_1, and the HX_1 showed the higher relative content of malvidin-, pelargonidin-,and cyanidin-based anthocyanins. Transcriptome and metabolome co-analysis revealed that the up-regulated expression of flavonoids synthesis gene was positively correlated with total anthocyanins accumulation in ramie leaf, and the differentfially expression of “blue gene” (F3’5’H) and the “red gene” (F3’H) in leaves bring out HX_1 metabolic flow more input into the cyanidin branch. Furthermore, the enrichment of glycosylated modification pathway (UGT and AT) and the expression of flavonoid 3-O-glucosyl transferase (UFGT), anthocyanidin reductase (ANR), in leaves were significantly influenced the diversity of anthocyanins between HX_1 and ZZ_1. Conclusions Phenotypic, transcriptomic and metabolomic analysis of HX_1 and ZZ_1 indicated that the expression levels of genes related to anthocyanin metabolism contribute to the color formation of ramie variety. Anthocyanins are important plant secandary metabilates with many physiological functions, the results of this study will deepened our understanding of ramie leaf color formation, and provided basis for molecular breeding of functional forage ramie.

Yellow to red colored betalains are a chemotaxonomic feature of Caryophyllales, while in most other plant taxa, anthocyanins are responsible for these colors. The carnivorous plant family Nepenthaceae belongs to Caryophyllales; here, red‐pigmented tissues seem to attract insect prey. Strikingly, the chemical nature of red color in Nepenthes has never been elucidated. Although belonging to Caryophyllales, in Nepenthes, some molecular evidence supports the presence of anthocyanins rather than betalains. However, there was previously no direct chemical proof of this. Using ultra‐high‐performance liquid chromatography‐electrospray ionization‐high‐resolution mass spectrometry, we identified cyanidin glycosides in Nepenthes species and tissues. Further, we reveal the existence of a complete set of constitutively expressed anthocyanin biosynthetic genes in Nepenthes. Thus, here we finally conclude the long‐term open question regarding red pigmentation in Nepenthaceae., Red colors are widely distributed in tissues of carnivorous Nepenthes plants. However, whether these colors are due to the presence of anthocyanins or betalains remained unclear. Here, we employed ultra‐high‐performance liquid chromatography‐electrospray ionization‐high‐resolution mass spectrometry and identified different cyanidin glycosides in Nepenthes species and tissues. In addition, the existence of a complete set of constitutively expressed anthocyanin biosynthetic genes in Nepenthes is shown.

The objective of the present work was to evaluate polyphenols, trace elements and compounds with antioxidant, antimicrobial and anti-hypertensive activity in wild strawberries cultivated in Southern Brazil. Fruits present high fiber, iron, potassium and sodium concentrations. Polyphenolic content was 242.12 mg of gallic acid equivalent per 100g and monomeric anthocyanin concentration was 100.50 mg of cyanidin 3-glucoside per 100g. Wild strawberries presented the capacity of scavenging 89% of ABTS•+ radical and 61% of DPPH• radicals and chelating power of 3.1, meanwhile the inhibition of the angiotensin-converting enzyme I activity was 12.5%. Fruits presented compounds with capacity to inhibit Staphylococcus aureus, Bacillus cereus, Listeria monocytogenes and Aeromonas hydrophyla. Thus, wild strawberries are important source of functional compounds and their consumption is a way to promote the Brazilian biodiversity and improve human diet.

The CRISPR/Cas9 system is a remarkably promising tool for targeted gene mutagenesis, and becoming ever more popular for modification of ornamental plants. In this study we performed the knockout of flavonoid 3′-hydroxylase (F3′H) with application of CRISPR/Cas9 in the red flowering poinsettia (Euphorbia pulcherrima) cultivar ‘Christmas Eve’, in order to obtain plants with orange bract colour, which accumulate prevalently pelargonidin. F3′H is an enzyme that is necessary for formation of cyanidin type anthocyanins, which are responsible for the red colour of poinsettia bracts. Even though F3′H was not completely inactivated, the bract colour of transgenic plants changed from vivid red (RHS 45B) to vivid reddish orange (RHS 33A), and cyanidin levels decreased significantly compared with the wild type. In the genetically modified plants, an increased ratio of pelargonidin to cyanidin was observed. By cloning and expression of mutated proteins, the lack of F3′H activity was confirmed. This confirms that a loss of function mutation in the poinsettia F3′H gene is sufficient for obtaining poinsettia with orange bract colour. This is the first report of successful use of CRISPR/Cas9 for genome editing in poinsettia. Supplementary Information The online version contains supplementary material available at 10.1007/s11240-021-02103-5., Key message Genome edited poinsettia plants show loss-of-function mutations in the F3’H gene introduced by CRISPR/Cas9. This is sufficient to change the bract colour from red to reddish orange. Supplementary Information The online version contains supplementary material available at 10.1007/s11240-021-02103-5.

Background: The genus Acer contains around 200 species, with more than 400 garden varieties. There is considerable diversity in these species and garden varieties, and each can be characterized by morphology and chemical composition. The red appearance of Acer leaves is due to anthocyanin compounds, including cyanidin glycosides, delphinidin glycosides, and galloylated anthocyanins. Few studies have investigated the diversity of anthocyanin compounds in garden varieties, and no studies have examined the pharmacological effects of these compounds. Objective: The purpose of this study was to identify the anthocyanins of Acer palmatum cv. ‘Chishio’, a garden variety of A. palmatum and evaluate their antiproliferative and antioxidant activities. Methods: A methanol extract of fresh leaves was partitioned with ethyl acetate. The extract was purified by column chromatography and compounds were subsequently identified by 1H and 13C NMR and ESI-HRMS. Antiproliferative activity was evaluated by 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4- sulfophenyl)-2H-tetrazolium, inner salt (MTS) colorimetric assay. The antioxidant assay was evaluated by scavenging activity using the stable radical DPPH. Results: The anthocyanins cyanidin-3-O-(6''-O-α-rhamnopyranosyl- β-glucopyranoside), cyanidin-3-O- β- glucopyranoside, cyanidin-3-O-[2''-O-(galloyl)-6''-O-(rhamnosyl)-β-glucoside], and cyanidin-3-O-[2''-O-(galloyl)- β-glucopyranoside] were isolated from A. palmatum cv. ‘Chishio’. All four anthocyanin compounds showed antiproliferative activity against LLC and T47D cells, and galloylated anthocyanin showed antiproliferative activity against C3H10T1/2 cells. All four anthocyanins inhibited the activity of DPPH radicals in a dosedependent manner. Conclusion: Maple anthocyanins could be a new cancer therapeutic agent or prophylactic medicine.

The Ginkgo extract EGb 761® manufactured with leaves of Ginkgo biloba has been continuously produced over decades at a large scale and is used as a clinically proven remedy for, among other things, the improvement of age-associated cognitive impairment and quality of life in patients with mild dementia. It belongs to the class of extracts addressed as quantified extracts according to the European Pharmacopeia. Accordingly, several compounds (e.g., flavone glycosides and terpene trilactones) are acknowledged to contribute to its clinical efficacy. Covering only about 30% of the mass balance, these characterized compounds are accompanied by a larger fraction of additional compounds, which might also contribute to the clinical efficacy and safety of the extract. As part of our systematic research to fully characterize the constituents of Ginkgo extract EGb 761, we focus on the structural class of proanthocyanidins in the present study. Structural insights into the proanthocyanidins present in EGb 761 and a quantitative method for their determination using HPLC are shown. The proanthocyanidins were found to be of oligomeric to polymeric structure, which yield delphinidin and cyanidin as main building blocks after acidic hydrolysis. A validated HPLC method for quantification of the anthocyanidins was developed in which delphinidin and cyanidin were detected after hydrolysis of the proanthocyanidins. The content of proanthocyanidins in Ginkgo extract EGb 761 was found to be approximately 7%.

Topicality. For today, the search for promising plants with a high content of anthocyanins to create safe herbal medicines is an urgent problem of modern science. Aim. To study the presence and severity of the cytotoxic activity of the dry extract of Gebu Dahlia variety flowers, the qualitative analysis and quantify the amount of anthocyanins in flowers of this variety. Materials and methods. For the study, the dry extract of Gebu flowers was obtained. The cytotoxicity analysis of 1 %; 0.5 %; 0.25 %; 0.125 %; 0.0625 % solutions of the extract were performed by microscopy on red bone marrow (RBM) cells of rats at an exposure of 15, 45, 90 minutes. The spectrophotometric study and high-performance liquid chromatography were used to assess the quantitative and qualitative content of the amount of anthocyanins. Results and discussion. The results obtained indicate that the viability of RBM cells is affected by the concentration of the extract and exposure: in the concentrations of 0.063-0.125 % no toxic effect of the extract was detected, while 0.25-1 % solutions were able to show cytostatic properties. The content of anthocyanin amount in the flowers was determined (1.8 % ± 0.02); 18 substances were identified, among them substances from the groups of cyanidin (54.7 %) and delphinidin (28 %) predominated. Conclusions. The first stage of testing of the dry extract from Gebu Dahlia variety flowers for potential toxicity has been carried out: the extract is potentially non-toxic in the lowest of the concentrations studied. For the first time, the content of anthocyanins in flowers of Gebu Dahlia variety has been determined, 18 substances from the groups of delphinidin, cyanidin, petunidine, peonidine, malvidin have been identified.

Blue flowers, which are rare, have long been a focus for researchers engaged in colored flower breeding. In this study, Plumbago auriculata, a plant with blue flowers, and its white flower forma Plumbago auriculata f. alba were used as research materials. Flower color quantification, environmental scanning electron microscopy (ESEM) observation of petal epidermal cells, and determination of the cell sap pH were carried out; moreover, metabolomic analysis was used to analyze the flavonoid metabolites of both types of petals. The results showed that the flower color of P. auriculata was bluish violet, and there was no significant difference in the epidermal cell distribution of the white and blue petals. The key substance that determined the bluish violet flower color was cyanidin-3-O-(6″-p-coumaroylglucoside) (Cy3-pC·G). Compared to the white petal cells, the blue petal cells exhibited up to 40 upregulated flavonoid compounds that were copigments. Together with the significantly increased pH (5.92 ± 0.12) of the petal cell sap, these copigments affected the color presentation of Cy3-pC·G, causing the final petal color of P. auriculata to be bluish violet. The results of this study indicate that cyanidin is an important anthocyanidin in blue flowers, which provides new insights into the breeding of blue flowers.

Ficus species have been used as a typical component in food and folk medicine in Asia for centuries. However, little is known regarding the bioactivity and genotoxicity of the recently identified Ficus dubia (FD), an indigenous plant of the tropical evergreen rain forest. FD is unique from other Ficus species because of its highly sought‐after red‐brown latex. Antioxidant properties together with phenolic and flavonoid contents of FD were elucidated. Health‐promoting characteristics were examined by studying the inhibition of enzymes as a drug target for diabetes, hypertension, Alzheimer's disease, and obesity, together with anticancer ability against human colorectal adenocarcinoma, human hepatocellular carcinoma, human ovarian carcinoma, human prostate adenocarcinoma, and human lung carcinoma. Besides, FD genotoxicity was tested using the Drosophila wing spot test. Results showed that both FD root and latex exhibited antioxidant activity due to the presence of phenolics and flavonoids, specifically caffeic acid and cyanidin. The ethanolic fraction of FD root demonstrated a potent antidiabetic mechanism underlying α‐glucosidase inhibitory activity similar to acarbose. This fraction also suppressed lung and ovarian cancer growth, possibly by G1 and G2/M arrest, respectively. All tested fractions lacked mutagenicity in vivo. Results indicated that FD can be developed as novel antidiabetic compounds; however, its bioactive compounds should be further identified., explored phenolic profile, health‐promoting activity, and genotoxicity assessment of Ficus dubia (FD), an indigenous plant of the tropical evergreen rain forest. Results indicated that FD can be developed as novel antidiabetic and anticancer compounds.

Corydalis ambigua (Japanese name, Ezoengosaku) flowers bloom with blue to purplish petals in early spring in Hokkaido prefecture. In this study, a mechanism for blue petal coloration by ferric ions and keampferol glycoside was elucidated. Blue petals and cell sap exhibited similar visible (Vis) spectra, with λmax at approximately 600 nm and circular dichroism (CD) with positive exciton-type Cotton effects in the Vis region. Analysis of the organic components of the petals confirmed cyanidin 3-O-sambubioside and kaempferol 3-O-sambubioside as the major flavonoids. Mg, Al, and Fe were detected in petals using atomic emission spectroscopy. Color, Vis absorption, and CD consistent with those of blue petals were reproduced by mixing cyanidin 3-O-sambubioside, kaempferol 3-O-sambubioside, and Fe3+ in a buffered aqueous solution at pH 6.5. Both Fe3+ and flavonol were essential for blue coloration.

Background: Our liver has a variety of vital functions including removing poisons, storing energy, immunological roles, and secretory and excretory functions. It may face some kinds of diseases caused by viruses, hepatotoxic chemicals, drugs, alcohol, and inherited disorders. Oxidative stress and inflammation are in the core of mechanisms of liver damages induced by viruses or chemical agents. Summary: Morus nigra (M. nigra), generally known as black mulberry, exhibited wide-spectrum pharmacological effects including antidiabetic, antinociceptive, anticancer, and hepatoprotective activities. Different parts of this plant particularly the fruit and leaf have shown beneficial effects on hepatocytes in cell culture and animal models of liver damages induced by chemicals (e.g., CCl4), drugs (e.g., paracetamol), diet (e.g., high fat), diabetes, etc. The beneficial effects of M. nigra on the liver are attributed to the presence of considerable amounts of phenolic compounds such as anthocyanins, flavonols, and phenolic acids. The present review is aimed to focus on the hepatoprotective activities of M. nigra and its phytochemicals and the mechanisms responsible for these activities. Key Messages: The evidence reviewed in this study can help design clinical trials on M. nigra in patients with liver disorders and develop a hepatoprotective herbal medicine.

The pericarp of longan (Dimocarpus longan Lour.) is rich in secondary metabolites and typically yellow-brown or gray-yellow in appearance. Here, we obtained a specific longan type, called red pericarp (RP) longan, which has a strong red pericarp. To understand the coloring mechanism of RP longan, metabolome and transcriptome data were used to analyze its secondary metabolites and molecular mechanism. From the results of liquid chromatography tandem mass spectrometry, 597 substances were identified in RP longan and 'Shixia' (SX) longan. Among these substances, 33 (mostly including flavonoids) were found in RP longan and 23 (mostly containing phenolic acids) were identified in SX longan. We identified five types of anthocyanins in longan pericarp, including three cyanidin derivatives, one delphinidin derivative, and one pelargonidin derivative. Three cyanidin derivatives, which contained cyanidin 3-O-glucoside, cyanidin 3-O-6″-malonyl-glucoside, and cyanidin O-syringic acid, were the primary components of anthocyanidins, and they only existed in RP longan. Delphinin 3-O-glucoside existed only in SX longan, and pelargonin O-rutinoside existed in RP and SX longan. However, their contents were extremely low. The structural genes F3H, F3'H, UFGT, and GST and the controlling genes containing MYB, bHLH, NAC, and MADS in the biosynthetic pathway of anthocyanin were significantly upregulated in RP longan. In summary, the strong red hue of RP longan is due to the accumulation of cyanidin derivatives in its pericarp, and the genes F3'H and F3'5'H may play an important role in selecting which component of anthocyanins will be synthesized. These results can provide scientific guidance for understanding and developing bioactive compounds from longan fruits.

Anthocyanins and PAs are the two most common flavonoids, which are widely present among diverse species. Great progress has been made in their synthesis and regulation. In this study, we analyzed the metabolic fluxes from their synthetic precursor leucoanthocyanins, which were obtained by overexpression of dihydroflavonol 4-reductase (DFR) in vitro and in vivo. The unstable product leucocyanidin generated in the CsDFRa enzymatic reaction was easily converted into C-type carbocations under weak acidic conditions, which could be further involved in the synthesis of C-type PAs in vitro. Additionally, the metabolites in tobacco overexpressing CsDFRa and Arabidopsis thaliana DFR and anthocyanidin synthase (ANS) mutants were investigated. In CsDFRa transgenic tobacco, the content of anthocyanins in the petals was greatly increased, but no catechin or PA was detected. In A. thaliana, EC-type carbocation was mainly accumulated in the wild type (WT), and the C-type carbocation was only detected in the ans mutant. In tea plant, the accumulation of C-type PAs is strong positively correlated with the expression of CsDFRa. In summary, leucocyanidin is not only involved in the synthesis of downstream anthocyanin and epicatechin but also can be converted into C-type carbocation to participate in the synthesis of C-type PAs. Hence, from leucocyanidin, three metabolic fluxes were formed toward catechin, cyanidin, and C-type carbocation. These results enriched the metabolic fluxes of leucoanthocyanins and further elaborated the roles of DFR in the process of C-type PA formation.

Radish (Raphanus sativus) is an important worldwide vegetable with a wide variety of colors that affect its appearance and nutritional quality. However, the large-scale detection, identification, and quantification of flavonoids in multicolor radish have rarely been studied. To uncover the diversity and accession-specific flavonoids in radish, liquid chromatography electrospray ionization-tandem mass spectrometry was used to analyze the metabolic profiles in the skin and flesh of six colored radish accessions: light-red Manshenhong, dark-red Touxinhong (TXH), purple Zijinling (ZJL), Xinlimei with red flesh (XLMF) and green skin, white Shizhuangbai (SZB), and black radish. In total, 133 flavonoids, including 16 dihydroflavones, 44 flavones, 14 flavonoids, 9 anthocyanins, and 28 flavonols, were characterized. The flavonoid metabolic profiles differed among the different colored radishes. Red and purple radishes contained similar anthocyanin compounds responsible for color pigmentation, including red cyanidin, callistephin, and pelargonin. Purple ZJL was most enriched with cyanidin o-syringic acid and cyanin, whereas callistephin and pelargonin were more abundant in dark-red TXH. Additionally, the black and white radishes shared similar anthocyanin and flavonoid profiles, suggesting that the color of black radishes was not caused by anthocyanin but by other metabolites. The metabolites in colored radishes that differed from SZB were mainly involved in the biosynthesis of plant secondary metabolites, such as flavonoid, flavone, flavonol, isoflavonoid, and phenylpropanoid biosynthesis. This study provides new insights into the differences in metabolite profiles among radishes with different skin and flesh colors. The results will be useful for aiding the cultivation of valuable new radish varieties.

It is shown that the selectivity of the separation of 15 anthocyanins from an extract of bilberries (3-galactosides, 3-glucosides and 3-arabinosides of the five main anthocyanins: cyanidin, peonidin, delphinidin, petunidin, and malvidin) with eluents containing acetonitrile and 10 vol % HCOOH in water can be controlled by varying the concentration of acetonitrile and separation temperature. A gradient mode at a separation temperature of 25°C is proposed for the rapid separation of all components without the introduction of methanol into the mobile phase. The developed method is used to determine anthocyanins in a number of commercial fruit products of plants of the Vaccinium family: bilberries, bog bilberries, cranberries, and lingonberries. A chromatographic version for eliminating the absorbance of polymer anthocyanins in the determination of monomeric compounds in complex mixtures is proposed as an alternative to differential spectrophotometry.

Three O-methyl anthocyanidin 3-O-β-D-glucopyranosides were isolated from bilberry extract on a large-scale basis together with two non O-methyl analogues. Anthocyanidin 3-O-β-D-galactopyranosides were removed from bilberry extract together with parts of anthocyanidin 3-O-α-L-arabinopyranosides after treatment with β-galactosidase. The remaining arabinopyranosides were removed by applying acid catalytic hydrolysis. The amounts of anthocyanins recovered as flavylium trifluoroacetic acid salt were as follows: 630 mg for petunidin 3-O-β-D-glucopyranoside, 423 mg for peonidin 3-O-β-D-glucopyranoside, 588 mg for malvidin 3-O-β-D-glucopyranoside, 877 mg for delphinidin 3-O-β-D-glucopyranoside, and 742 mg for cyanidin 3-O-β-D-glucopyranoside.

Background Pomegranate (Punica granatum) is one of the oldest known edible fruit. Recently, there has been an increased interest in this fruit as a functional food for health benefits due to its use in disease prevention and promotion of overall health wellness. Objective This study aims to investigate the effects of pomegranate extract for the development of non-opioid substitution therapy for in-vitro and in-vivo studies. Materials and methods Anthocyanin contents consisting of cyanidin 3-glucoside, diglucoside, and pelargonidin 3-glucoside, diglucoside were detected and quantified in pomegranate extract using high-performance liquid chromatography. The optimum dosage of the extract was determined based on the regulation of MORs and cAMP proteins in U-87 cells. Co-treatment of the extract with morphine was performed to evaluate its potency in reducing the concentration levels of MORs and cAMP. For animal studies, rats were divided into two major groups representing both acute and chronic morphine-induced treatments and the Morris water maze (MWM) study was employed after treatment for each rat. The rats were sacrificed after the treatments and serum samples were collected to evaluate the levels of CREB and BDNF. Results The results indicated that each of the anthocyanin content tested in the study was present in the pomegranate extract. Additionally, in-vitro studies using pomegranate extract treatment showed that the extract was effective in decreasing the MORs and cAMP protein levels in U-87 cells at a concentration of 0.125 mg/mL. The memory impairment based on the MWM study in rats was also subsequently improved after treatment with pomegranate extract as compared to treatment with morphine. The blood serum derived from the rats treated with pomegranate extract also showed a significant decrease in CREB level and an increase in BDNF as compared to rats treated with morphine. Conclusion In conclusion, this study substantiates the potency of pomegranate extract as a non-opioid substitution therapy for in-vitro and in-vivo studies.

Chaura (Gaultheria poeppigii) is a plant species native from Southern Chile, which produces a berry fruit with potential beneficial health effects due to its content of phenolic compounds. The qualitative and quantitative determination of the phenolic compounds from fruits of different colored genotypes (white-, pink- and red-colored) collected from the Osorno volcano and the Conguillio National Park (CNP) in southern Chile were analyzed by mass spectrometry (HPLC-DAD-ESI-MS/MS) and HPLC-DAD, respectively. The total content of phenolic compounds was evaluated by the Folin-Ciocalteu method, and its antioxidant activity by the CUPRAC, TEAC and DPPH methods. Four anthocyanins were detected, with glycosylated derivatives of delphinidin and cyanidin being the most abundant. Fruits with more coloration had higher anthocyanin concentrations. Six flavonols were detected, with quercetin derivatives being the most abundant. The highest concentration of total flavonols reached 0.41 mg g-1 in red colored fruits. The profiles of phenolic compounds showed differences between fruits depending on both the color and the area of collection. Finally, it would be interesting to evaluate the genetic profiles of chaura to determine whether this variation in phenolics and colorations is dependent on the geographical location or dependent on the genotype of the plant.

Background The beneficial rhizobacterium, Pseudomonas fluorescens N 21.4, and its metabolic elicitors were inoculated in commercial cultivars of blackberry plants (Rubus cv. Loch Ness). Phenolic compounds present in red and black fruit and the expression of structural marker genes of the phenylpropanoid pathway during fruit ripening were studied. Results An inverse relationship between gene expression and accumulation of metabolites was seen, except for the RuDFR gene, which had a direct correlation with cyanidin 3-O-glucoside synthesis, increasing its content 1.3 times when RuDFR was overexpressed in the red fruit of plants inoculated with the metabolic elicitors of P. fluorescens N 21.4, compared with red fruit of plants inoculated with N 21.4. The RuCHS gene also had a fundamental role in the accumulation of metabolites. Both rhizobacterium and metabolic elicitors triggered the flavonoid metabolism, enhancing the catechin and epicatechin content between 1.1 and 1.6 times in the case of red fruit and between 1.1 and 1.8 times in the case of black fruit. Both treatments also boosted the anthocyanin, quercetin, and kaempferol derivative content, highlighting the effects of metabolic elicitors in red fruit and the effects of live rhizobacterium in black fruit. Conclusion The metabolic elicitors' capacity to modulate gene expression and to increase secondary metabolites content was demonstrated. This work therefore suggests that they are effective, affordable, easily manageable, and ecofriendly plant inoculants that complement, or are alternatives to, beneficial rhizobacteria. © 2020 Society of Chemical Industry.

Young buds of Toona sinensis (A. Juss.) Roem with abundant flavonoids have aroused considerable attention for their health benefits. In this study, the diversity of anthocyanins (two cyanidin glycosides) and flavonols (11 quercetin and kaempferol derivatives) of five dominant cultivars of T. sinensis were analysed using HPLC–DAD and HPLC–ESI–MS/MS, and their antioxidant activities were evaluated with DPPH, FRAP and ORAC assays. Results showed that these characteristics were significantly cultivar-dependent (P

Syzygium cumini (S. cumini) is an underutilized fruit of tropical and subtropical regions with various bioactive compounds distributed in all parts of the plant. The fruit and its by-products, such as seeds, have both nutritional and medicinal value. However, fruit and seeds have not been fully considered as potential functional food ingredients to develop foods with promising health benefits. Based on the available information in the literature, fruit and seed are rich in phytochemicals, such as myricetin, oxalic acid, gallic acid, citronellol, cyanidin diglucoside, hotrienol, phytosterols, flavonoids, carotenoids and polyphenols as well as micronutrients. In addition, they were reported to possess several beneficial health properties. Further, research in this area would provide valuable information for their potential utilization as functional food ingredients. This review presents comprehensive information about the bioactive compounds and nutraceutical properties of S. cumini fruit and seeds, as well as the potential of using them as functional food ingredients.

In this study, the stability of a submicron emulsion to protect an extract obtained from sea grape fruit (Coccoloba uvifera L.) was evaluated. Extract characterization by MS-HPLC revealed the presence of 3 anthocyanins (cyanidin 3-glucoside, malvidin 3-glucoside, and delphinidin 3-glucoside), the content of total phenols was 263.86 ± 1.86 mg gallic acid equivalent/100 g, with an antioxidant capacity determined by ABTS and DPPH of 128.95 ± 1.00 and 26.18 ± 0.60 μg Trolox equivalents/mL, respectively. A submicron emulsion (0.424 μm) by Ultrasound with monomodal distribution, stable over time and low viscosity (1.94 mPa s) classified as a shear-thinning fluid was obtained. The thermogravimetric analysis (TGA) demonstrated the stability of the C. uvifera extract in the emulsion, which is thermostable (212 °C). These emulsions can be added into a beverage as a nutraceutical, dried for later use as pills or incorporated in foods.

Currently, gastric cancer (GC) and gallbladder cancer (GBC) constitute important causes of human deaths related to cancer worldwide. In the last years, several researches are focused on the role of dietary compounds in preventing cancers. The consumption of fruits with high antioxidants, mainly anthocyanins, represents a good option to reduce the risk of chronic human diseases. Calafate (Berberis microphylla G. Forst.) berries, recognized by their remarkable antioxidant properties and high content of anthocyanins, appear as a new alternative to treat degenerative diseases of public interest. The present work was aimed to evaluate the impact of crude and anthocyanin-rich extracts from Calafate fruits on in vitro cell viability and migration capacity of gastric (AGC) and gallbladder (G415) human cancer cell lines, as related with their antioxidant properties. Crude and anthocyanin-rich extracts were obtained from fruits of Calafate grown under field conditions in the south of Chile. Antioxidants, phenols, anthocyanins, and anthocyanidins were determined. In vitro cell viability and migration of AGS and G415 human cancer cell lines at different concentrations of extracts (25–800 μg mL−1) were determined. Anthocyanin-rich extracts of Calafate berries showed comparable antioxidant activity (up to 1200 μg Trolox eq. g−1DW), slightly lower total phenolic content (12%), but higher total anthocyanin content (25%) compared to the crude extract. The major anthocyanidin molecule detected in both extracts was delphinidin, followed by malvidin, and low concentrations of petunidin, cyanidin, and peonidin. As expected, all of these compounds were detected in higher levels in anthocyanin-rich extracts (up to 2-fold). Noteworthy, our study revealed that Calafate fruit extracts strongly decrease in vitro viability and migration capacity of gastric carcinoma (AGC model) and gallbladder carcinoma (G415 model) human cell lines; however, the anthocyanin-rich extract displayed higher inhibitory effects (up to 70%) compared to crude extracts. These findings allow suggesting that the in vitro antiproliferative potential of Calafate fruit extract is strongly related to the anthocyanin concentration, especially delphinidin.

Cyanidin 3,5-di-O-glucoside anthocyanin was extracted from red rose flower petals and used as reducing and capping agent for the green synthesis of anisotropic gold nanoparticles (Au NPs). Transmission electron microscope (TEM) images indicated that the Au NPs have large number of small spheres of gold. Surface plasmon resonance band position strongly depended on the [HAuCl4] and [anthocyanin]. Cationic surfactant distinctly changed the shape, size, number of NPs, and size distribution of Au nanodisks at room temperature. Conventional techniques were used to the estimate the antiradical and antimicrobial activities of the cyanidin 3,5-di-O-glucoside anthocyanin and gold NPs. The 2,2-diphenyl-l-picrylhydrazyl nitrogen radical (DPPH·), two bacteria strains (Staphylococcus aureus and Escherichia coli), and two yeast strains (Candida albicans ATCC 10231 and Candida parapsilosis ATCC 22019) were used to determine the antioxidant and antimicrobial properties of CTAB-capped gold NPs. Eosin yellow photocatalytic degradation followed apparent first-order kinetics with activation energies of 54.4 kJ/mol and 39.5 kJ/mol, respectively, for oxidative and sunlight catalyzed paths. The photocatalytic rates drastically inhibited with scavengers, demonstrating that the reactive radical oxygen species (HO· and O2−·), holes (h+) and electrons (e−) played major role in the degradation.

Titanbicus (TB), a hybrid of Hibiscus moscheutos × H. coccineus (Medic.) Walt., has potential to be used as an edible flower. In this study, proximate nutritional content, anthocyanin content, total polyphenol content (TPC), and antioxidant activities in vitro and in vivo were investigated. Three cultivars of TB, namely Artemis (AR), Rhea (R), and Adonis (AD), were used as materials. Protein and carbohydrates were the primary macronutrients, while crude fat and ash were detected in trace amounts. Cyanidin 3-glucoside (Cy3-G) and cyanidin 3-sambubioside (Cy3-Sam), were identified in all TBs. The highest anthocyanin content was observed in AD (47.09 ± 1.45 mg/g extract), followed by R and AR (6.04 ± 0.20 and 2.72 ± 0.11 mg/g extract, respectively). The TPC of AD (225.01 ± 1.97 mg/g extract) was greater than that of AR and R (185.41 ± 3.24 and 144.10 ± 1.71 mg/g extract, respectively). AD exhibited the strongest in vitro antioxidant activity in hydrophilic oxygen radical absorbance capacity, compared to the other two TBs. In addition, AD extract suppressed the generation of reactive oxygen species in caudal fin of wounded zebrafish. Antioxidant activities of AD appeared to be related to its total anthocyanin content, Cy3-G, Cy3-Sam, and TPC. Our findings indicate that TB, particularly the AD cultivar, would be an attractive source of bioactive compounds with antioxidant activities, and can improve both nutritional value and appearance of food.

Sweet sorghum (Sorghum bicolor) is one of the most important cereal crops in the world with colorful seeds. To study the diversity and cultivar-specificity of phytochemicals in sweet sorghum seeds, widely targeted metabolomics was used to analyze the metabolic profiles of the white, red, and purple seeds from three sweet sorghum cultivars Z6, Z27, and HC4. We identified 651 metabolites that were divided into 24 categories, including fatty acids, glycerolipids, flavonoids, benzoic acid derivatives, anthocyanins, and nucleotides and its derivatives. Among them, 217 metabolites were selected as significantly differential metabolites which could be related to the seed color by clustering analysis, principal component analysis (PCA), and orthogonal signal correction and partial least squares-discriminant analysis (OPLS-DA). A significant difference was shown between the red seed and purple seed samples, Z27 and HC4, in which 106 were downregulated and 111 were upregulated. The result indicated that 240 metabolites were significantly different, which could be related to the purple color with 58 metabolites downregulated and 182 metabolites upregulated. And 199 metabolites might be involved in the red phenotype with 54 downregulated and 135 upregulated. There were 45 metabolites that were common to all three cultivars, while cyanidin O-malonyl-malonyl hexoside, cyanidin O-acetylhexoside, and cyanidin 3-O-glucosyl-malonylglucoside were significantly upregulated red seeds, which could be the basis for the variety of seed colors. Generally, our findings provide a comprehensive comparison of the metabolites between the three phenotypes of S. bicolor and an interpretation of phenotypic differences from the point of metabolomics.

In this work, we studied the potential photoprotective effect of Ipomoea horsfalliae Hook., Convolvulaceae, flower extract. Ipomoea horsfalliae is a plant that grows in tropical and subtropical regions. I. horsfalliae ethanolic extracts were analyzed by ultra-high efficiency liquid chromatography–high-resolution mass spectrometry. Dicaffeoylquinic acid, chlorogenic acid, scopoletin, glycosylated cyanidin, pelargonidin, and kaempferol were identified as major components of I. horsfalliae flower extract. In vitro biossays were used to evaluate cytotoxic and sensitizing effects of the extracts, and their photoprotective effect was evaluated in BALB/c mice. Morphological and histopathological observation of the skin tissues from mice suggested that UV-B-induced edema was significantly inhibited by treatment with I. horsfalliae flower extract. It was not cytotoxic for both cancerous and normal cells, and no sensitizing effect was observed. I.horsfalliae flower extract appears to be a good starting point for research programs leading to the development of natural skin care products.

α-Glucosidase inhibitors are widely used to suppress postprandial glycemia in the treatment of type 2 diabetes mellitus. The present study evaluated the in vitro α-glucosidase inhibitory activity of three major pigment constituents of Cinnamomum camphora fruit, namely cyanidin, cyanidin 3-rutinoside, and cyanidin-3-O-glucoside. We found that cyanidin exerted strong inhibitory activity on α-glucosidase, with IC50 of 5.293 × 10−3 mM, whereas cyanidin 3-rutinoside and cyanidin-3-O-glucoside did not show inhibitory activity on α-glucosidase. The inhibitory activity of cyanidin was stronger than that of acarbose (IC50 1.644 mM), the current most commonly used drug for postprandial glycemia. Kinetic analysis indicated that cyanidin inhibited α-glucosidase through competition, with a Ki value of 0.0183 mM. Fluorescence spectrum titration showed only one binding site between cyanidin and α-glucosidase, and the binding constant was calculated. Further, molecular docking was conducted to simulate the binding interactions between cyanidin and α-glucosidase. Cyanidin was found to interact with several residues close to the catalytic site of α-glucosidase through π-π stack interaction and hydrogen bonds. The calculated binding energy of the cyanidin and enzyme complex was −105.031 kJ/mol. Molecular simulation and calculation showed that the van der Waals force played an essential role in the binding of α-glucosidase and cyanidin.

Background: Inflammatory mediators produced by cyclooxygenase (COX) and lipoxygenase (LOX) pathways are responsible for many human diseases, such as cancer, arthritis, and neurological disorders. Flavonoid-containing plants, such as Ipomoea batatas leaves, have shown potential anti-inflammatory activity. Objectives: This study aimed to predict the actions of 10 compounds in I. batatas leaves, which are YGM–0a [cyanidin 3–0–sophoroside–5–0–glucosede], YGM–0f [cyanidin 3–O–(2–0–(6–0–(E)–p–coumaroyl–β–D–glucopyranosyl)–β–D–glucopyranoside)–5–0–β–D–glucopyranoside], YGM–1a [cyanidin 3–(6,6′–caffeylp–hydroxybenzoylsophoroside) –5–glucoside], YGM–1b [cyanidin 3–(6,6′–dicaffeylsophor-oside)–5–glucoside], YGM–2 [cyanidin 3–(6–caffeylsophoroside)–5–glucoside], YGM–3 [cyanidin 3–(6,6′–caffeyl-ferulylsophoroside)–5–glucoside], YGM–4b [peonidin 3–(6,6′–dicaffeylsophoroside)–5– glucoside], YGM–5a [peonidin 3–(6,6′–caffeylphydroxybenzo-ylsophoroside)–5–gluco-side], YGM–5b [cyanidin 3–6–caffeylsophoroside)–5–glucosede], and YGM–6 [peonidin 3–(6,6′–caffeylferulylsophoroside)–5–glucoside] as LOX inhibitors, and also predict the stability of ligand–LOX complex. Materials and Methods: The compounds were screened through docking studies using PLANTS. Also, the molecular dynamics simulation was conducted using GROMACS at 310K. Results: The results showed that the most significant binding affinity toward LOX was shown by YGM–0a and YGM–0a, and the LOX complex in molecular dynamics simulation showed stability for 20 ns. Conclusion: Based on Docking Studies and Molecular Dynamics Simulation of I. Batatas Leaves compounds, YGM-0a was shown to be the most probable LOX inhibitor.

In this study, eight different pomegranate (Punica granatum L.) cultivars from Turkey were evaluated for their antioxidant and cytotoxic effects on the MCF-7 breast cancer cell lines and MCF-10A breast fibrocystic epithelial cell lines with a focus on their chemical compositions by LC-MS/MS. Cell lines were treated with pomegranate juice extracts in different doses at selected time intervals (24th, 48th, and 72nd hour). Afterwards, WST-1 cell proliferation assay was performed to investigate the cytotoxicity of the extracts. Accordingly, all extracts decreased the cell viability of MCF-7 breast cancer cell lines and had no cytotoxic effect on the cell viability of MCF-10A cell lines. Among eight extracts, P7 (Izmir 1513), which was rich in anthocyanins such as cyanidin chloride (69.76 +/- 8.02 mu g/g extract), cyanidin-3-O-glucoside (903.66 +/- 101.89 mu g/g extract), and punicalagin (992.09 +/- 174.53 mu g/g extract), was found to demonstrate the strongest cytotoxic activity on MCF-7 breast cancer cell lines by decreasing the cell viability in half at 24th hour with an IC50 value of 49.08 mu g/ml. Practical applications Eight commercially valuable pomegranate (Punica granatum) cultivars from Turkey were examined. Pelargonidin, cyanidin, cyanidin-3-O-gl, callistephin, and delphinidin-3-O-gl were quantified. Two cultivars (P1 and P3) showed comparatively higher antioxidant effects. A cultivar (P7) showed strongest cytotoxic activity against MCF-7 breast cancer cell line. The cultivars have potential to be used as natural antioxidant and anticancer agents.

In this research, the effects of drying method, storage temperature, and color protector glucose on anthocyanin preservation in the Lycium ruthenicum Murr. fruit were studied. Compared with hot-air drying, vacuum freeze-drying preserved about 5.8-fold more anthocyanins. The half-life of anthocyanins in the freeze-dried fruit samples with glucose was 3.6 days, 1.8 days, and 1.7 days at 4 °C, 20 °C, and 37 °C, respectively. On the other hand, the half-life values without glucose addition were 2.2 days, 2.3 days, and 2.1 days at each temperature, respectively, indicating that glucose protected anthocyanins at low temperature. The composition and contents of anthocyanins and anthocyanidins in the freeze-dried Lycium ruthenicum Murr., stored for 20 days, were investigated with a HPLC-MS/MS setup. It was found that most anthocyanidins in Lycium ruthenicum Murr. are linked with coumaroyl glucose to form anthocyanins, while glycosylated and acetyl-glycosylated anthocyanins were also detected. Five anthocyanidins were detected: delphinidin, cyanidin, petunidin, malvidin, and peonidin, and delphinidin accounts for about half of the total amount of anthocyanidins. It is much more economic to conserve anthocyanins in situ with freeze-drying methods and to store the fruits at low temperatures with glucose.

This study aimed to investigate the thermal stability and biological activities of the phytochemicals from the red onion skins extract, which are a rich source of anthocyanins. Eight anthocyanins were identified in the extract by high-performance liquid chromatography, the most abundant ones being cyanidin 3-O-laminaribioside and cyanidin 3-O-(6″-malonoyl-laminaribioside). The study also involved the assessment of the thermal degradation kinetics of anthocyanins and antioxidant activity in the 75–155 °C temperature range. The thermal degradation kinetics was described using the first-order kinetics model. In terms of thermal stability, increasing the temperature resulted in lower half-life values (t1/2) and higher degradation rate constant values (k) for both anthocyanins and antioxidant activity. The thermodynamic parameters revealed that the phytochemicals’ degradation is a non-spontaneous and endothermic reaction. Furthermore, the inhibitory effect of the extract was investigated against the enzymes affiliated with metabolic syndrome, oxidative stress, and inflammatory process diseases. Thus, we also demonstrated that the red onion skins extract exerted inhibitory activity on α-glucosidase, α-amylase, lipase, and lipoxygenase. Considering the high content of bioactives and various biological properties, the red onion skins extract is suitable for multiple applications.

The Himalayan wild berries Myrica esculenta, Duchesnea indica, Prunus cerasoides, and Berberis lycium were studied for the first time for polyphenolic compositions using high-performance liquid chromatography/electrospray ionization tandem mass spectrometry. The chemical analysis of extracts resulted in the identification of 69 polyphenols, including 11 anthocyanins, 28 phenolic acids, 19 flavanoids, 10 ellagitannins, and 1 dihydrochalcone. The caffeoylquinic acids, quercetin, kaempferol, and cyanidin are the common moieties in studied wild berries. In addition, seven phenolic compounds, that is, gallic acid, vanillic acid, caffeic acid, rutin, ferulic acid, quercetin, and myricetin were quantified. Among anthocyanins, cyanidin-3-O-glucoside was the majorly quantified anthocyanin that ranged from 2.52 to 6.18% followed by delphinidin-3-O-glucoside (0.6%-5.53%). The samples were assessed for total phenolics, total anthocyanin content, and antioxidant potential. The results showed that M. esculenta and B. lycium had the highest total phenolic and anthocyanin content and exhibited promising antioxidant activity with IC50 of 32.100 ± 0.42 and 48.44 ± 0.46 μg/mL, respectively. Principal component analysis was able to clearly differentiate between four underutilized Himalayan wild edible berries. The wide variability of polyphenolic constituents supports the consumption of these berries not only to achieve the nutrient requirements among local people but also as promising sources of antioxidants for the food industry.

Color is an essential agronomic trait and the consumption of high anthocyanin containing vegetables in daily diet does provide benefits to human health, but the mechanisms on anthocyanin accumulation in tender pods of okra (Abelmoschus esculentus L.) were totally unknown. In this study, a wide characterization and quantitation of anthocyanins and flavonols in tender pods of 15 okra varieties were performed by UHPLC-Q-Orbitrap HRMS for the first time. Two major anthocyanins (delphinidin 3-O-sambubioside and cyanidin 3-O-sambubioside) and six kinds of flavonol glycosides (most are quercetin-based) were identified and quantified. The coloration of the purple okra pod mainly arises from the accumulation of both delphinidin 3-O-sambubioside and cyanidin 3-O-sambubioside in most of purple varieties (Hong Yu, Bowling Red and Burgundy), except Jing Orange. The significant differences in the compositions and contents of anthocyanins are responsible for the pod color ranging from brick-red to purplish-red among the various okra cultivars. Furthermore, four representative okra cultivars exhibiting obvious differences in anthocyanin accumulation were further analyzed with transcriptome and more than 4000 conserved differentially expressed genes were identified across the three compared groups (B vs. BR, B vs. HY and B vs. JO). Based on the comprehensive analysis of transcriptomic data, it was indicated that MBW complex consisting of AeMYB114, AeTT8, and AeTTG1 and other transcriptional factors coordinately regulate the accumulation of anthocyanins via the transcriptional regulation of structural genes. Moreover, four independent working models explaining the diversities of anthocyanin pigmentation in okra pods were also proposed. Altogether, these results improved our understanding on anthocyanin accumulation in okra pods, and provided strong supports for the development of okra pod as a functional food in the future.

Effect of low temperature and low oxygen concentration on biochemical attributes, antioxidant enzyme activities, phenolics profile and expression of phenylpropanoid pathway-related genes was investigated in crabapple (Malus profusion) fruit. Crabapple fruit were kept at room temperature (RT, 20 ± 2 °C and 25 ± 2 °C alternatively at 12 h cycle) or low temperature (LT, 10 ± 2 °C and 25 ± 2 °C alternatively at 12 h cycle) and supplemented with either normal oxygen (21%) or low oxygen levels (5%) for 9 days. Results revealed higher concentrations of soluble solids, titratable acids, and ascorbic acid in fruit stored at LT + 5% O2. Likewise, total phenolics, peroxidase activity, and 2,2´-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)-radical scavenging activity were observed to be significantly higher in fruit stored at low temperature (LT + 5% O2 > LT + 21% O2), followed by those stored at room temperature (RT + 5% O2 > RT + 21% O2). In contrast, H2O2 and malondialdehyde contents were significantly enhanced in fruit stored at room temperature (RT + 21% O2 and RT + 5% O2), whereas fruit stored at low temperature showed minimum inhibition in superoxide dismutase, catalase and ascorbate peroxidase activities. In addition, low temperature induced biosynthesis of phenolic acids, whereas no considerable changes were observed in flavanols and dihydrochalcones during storage. Low temperature and oxygen conditions (LT + 5% O2) significantly enhanced the biosynthesis of flavonols (glycosylated quercetin derivatives) and cyanidin 3-galactoside, compared to LT + 21% O2, RT + 5% O2 and RT + 21% O2 conditions. In addition, low temperature also up-regulated the expression of MpFLS and MpUFGT in fruit tissues. Moreover, correlation analysis suggested positive association of antioxidant capacity with the biosynthesis of flavonols and anthocyanins in fruit stored at LT + 5% O2.

For various reasons, histologists in several parts of the world have tried to replace hematoxylin and eosin with locally available plant dyes of the anthocyanin family. Blue or violet nuclear stains have been created by combining an anthocyanin with iron or aluminum ions at low pH. Obtaining a pink or red cytoplasmic counterstain, however, has not been achieved previously, even with a red solution of anthocyanin, because the chemistry of the colorant does not allow bonding to cytoplasmic materials and collagen. We used two extracts from the petals of common mallow, Malva sylvestris, to create both a blue nuclear stain and a red counterstain. The two extracts contained two chemically distinct types of anthocyanins. The first extract contains vic-hydroxyls capable of complexing aluminum ions; its flavylium core is cationic. The second type lacks vic-hydroxyls on its core structure, but includes pendant glucosides that contain a malonic acid ester with a free carboxyl substituent. The precise identity of the first anthocyanin currently is unknown, but likely is one or more of the common anthocyanins such as cyanidin, delphinidin or petunidin, which complex readily with aluminum. The second anthocyanin is malonated malvidin, which does not complex with aluminum, but is anionic at the pH used here. The overall visual effect of applying the two anthocyanin extracts is remarkably similar to that of hemalum plus eosin.

The red color formation of Acer mandshuricum leaves is caused by the accumulation of anthocyanins primarily, but the molecular mechanism researches which underlie anthocyanin biosynthesis in A. mandshuricum were still lacking. Therefore, we combined the transcriptome and metabolome and analyzed the regulatory mechanism and accumulation pattern of anthocyanins in leaf color change periods in three different leaf color states. In our results, 26 anthocyanins were identified. Notably, the metabolite cyanidin 3-O-glucoside was found that significantly correlated with the color formation, was the predominant metabolite in anthocyanin biosynthesis of A. mandshuricum. By the way, two key structural genes ANS (Cluster-20561.86285) and BZ1 (Cluster-20561.99238) in anthocyanidin biosynthesis pathway were significantly up-regulated in RL, suggesting that they might enhance accumulation of cyanidin 3-O-glucoside which is their downstream metabolite, and contributed the red formation of A. mandshuricum leaves. Additionally, most TFs (e.g., MYBs, bZIPs and bHLHs) were detected differentially expressed in three leaf color stages that could participate in anthocyanin accumulation. This study sheds light on the anthocyanin molecular regulation of anthocyanidin bio-synthesis and accumulation underlying the different leaf color change periods in A. mandshuricum, and it could provide basic theory and new insight for the leaf color related genetic improvement of A. mandshuricum.

Flavonoids play important roles in regulating plant growth and development. In this study, three kaempferol 3-O-glycosides were identified and mainly accumulated in flowers but not in leaves or fruits ofMalus. InMalus, flower petal color is normally white, but some genotypes have red flowers containing anthocyanin. Anthocyanin biosynthesis appears to be in competition with kaempferol 3-O-glycosides production and controlled by the biosynthetic genes. The white flowerMalusgenotypes had better-developed seeds than the red flower genotypes. In flowers, the overexpression ofMYB10inMalus domesticaenhanced the accumulation of anthocyanin, but decreased that of kaempferol 3-O-glycosides. After pollination the transgenic plants showed slower pollen tube growth and fewer developed seeds. Exogenous application of different flavonoid compounds suggested that kaempferol 3-O-glycosides, especially kaempferol 3-O-rhamnoside, regulated pollen tube growth and seed set rather than cyanidin or quercetin 3-O-glycosides. It was found that kaempferol 3-O-rhamnoside might regulate pollen tube growth through effects on auxin, the Rho of plants (ROP) GTPases, calcium and the phosphoinositides signaling pathway. With the inhibition of auxin transport, the transcription levels of Heat Shock Proteins (HSPs) and ROP GTPases were downregulated while the levels were not changed or even enhanced when blocking calcium signaling, suggesting that HSPs and ROP GTPases were downstream of auxin signaling, but upstream of calcium signaling. In summary, kaempferol glycoside concentrations in pistils correlated with auxin transport, the transcription of HSPs and ROP GTPases, and calcium signaling in pollen tubes, culminating in changes to pollen tube growth and seed set.

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.

Consumption of fresh fruit is known to protect against non-communicable diseases due to the fruit's content in compounds with an antioxidant capacity, among them is polyphenols. Asian plums (Prunus salicina L.) accumulate more than 40 phenolic compounds, with a remarkable diversity in their profiles, depending on the variety and environmental conditions. Although candidate genes have been indicated to control this trait, the loci controlling its phenotypic variation have not yet been defined in this species. The aim of this work was to identify the quantitative trait Loci (QTL) controlling the phenolic compounds content in the Asian plum skin and flesh. Using UHPLC-DAD-Orbitrap-MS, we determined that cyanidin-3-glucoside and cyanidin-3-rutinoside are the main anthocyanins in Asian plums. Other anthocyanins found to a lesser extent were tentatively identified as cyanidin bound to different sugar and procyanidin moieties. Then we phenotyped fruits of 92 and 80 F1 seedlings from the cross < “98.99” × “Angeleno”> (98 Ang) for two harvest seasons. We used HPLC-DAD to quantify single anthocyanin and spectrophotometric techniques to determine the total content of phenols, flavonoids, procyanidins, and antioxidant activity (DPPH and FRAP). To determine the phenotype-genotype association of phenolic compounds content, phenotypic values (adjusted by linear mixed-effects models), genotypic data and linkage maps were analyzed with the multiple QTL model (MQM) approach. We found a total of 21 significant trait-marker associations: 13 QTLs segregating from “98.99” and 8 QTLs from “Angeleno.” From these associations, 8 corresponded to phenolic compound content in the flesh and 13 in the skin. Phenotype variance was explained by the detected loci, ranging from 12.4 to 27.1%. The identified loci are related to the content of cyanidin-3-glucoside (LG4), cyanidin-3-rutinoside (LG4), total flavonoids and procyanidins (LG5 and LG8), and minor anthocyanin compounds (LG3 and LG4). These results will help improve the efficiency of breeding programs for the generation of Asian plum varieties with high phenolic compound content., This work has been funded by the National Agency of Research and Development (ANID), Chile: Fondecyt start into Research No. 11150662, Fondecyt Regular No. 1191446, and FONDEF Project IT17I0069 Sweet Pekeetah: un modelo tecnológico-comercial para una nueva variedad chilena de fruta; BB and CS-A were supported by BECAS DE DOCTORADO NACIONAL/2020 No. 21200330 and 21191605, respectively. The work of JS was supported by the Ministry of Science and Innovation of Spain through Juan de la Cierva incorporation contract (IJC2018-036623-I)

Предпочтения производителей и потребителей пищевых продуктов ориентированы на использование натуральных ингредиентов, в том числе натуральных красителей. Признанным источником красных пищевых красителей – антоцианов является дикорастущая ягода – клюква обыкновенная Vaccinium oxycoccos L. Разработка эффективной технологии переработки ягод, обеспечивающей наиболее полную экстракцию в сок антоциановых соединений, позволит получать ягодные соковые ингредиенты с высоким содержанием природных антоциановых красителей и других биологически активных веществ ягод для применения в составе рецептур пищевых продуктах. Проведены исследования по экспериментальному обоснованию и разработке условий предварительной обработки ягод клюквы при получении сока с применением различных способов (бланширование, СВЧ, УЗ, ферментативная обработка), обеспечивающие наиболее полную экстракцию в сок антоциановых соединений. Установлено, что проведение предварительной обработки ягод клюквы при получении сока с помощью пресса оказывает существенное влияние на выход сока, экстракцию антоцианов и антиоксидантную активность сока. Экспериментально установлено, что применение УЗ и СВЧ предобработки ягод клюквы в разработанных условиях способствует увеличению выхода сока на 16-27 мас. (или об.)%, антоцианов - в 1,5-1,9 раза, антиоксидантной активности сока- в 1,1 и 1,2 раза. Более эффективными являются предварительная стадия бланширования и проведение ферментативной обработки с использованием МЭК на основе Фруктоцим П-6Л и Laminex BG2: выход сока увеличивается в 2,5 и 1,3 раза, антоцианов – в 3,0 и 2,2 раза, антиоксидантная активность сока возрастает в 1,3 и 1,25 раза соответственно по сравнению с аналогичными показателями, установленными для соков, полученных из ягод клюквы, не подвергавшихся предварительной обработке. Выявлено, что проведение предобработки ягод клюквы не приводит к качественным изменениям состава антоциановых соединений сока и их количественных соотношений. Показано, что антоциановый профиль клюквенных соков представлен шестью антоцианами на основе цианидина и пеонидина, углеводными компонентами выступают глюкоза, галактоза, арабиноза. Преобладающими антоцианами являются цианидин-3-галактозид (24,6-25,0%) и пеонидин-3-галактозид (28,7-31,4%).

Juçara fruit pomace is one of the most abundant byproducts of the pulp-making process, generally discarded despite their attractive nutritional content. In this sense, this study aimed to investigate the potential of juçara fruit pomace as an alternative source of starch and natural dyes. Starch extracted from juçara seed (JS) was characterized in approximate composition, crystallinity, thermal profile, morphology, and equilibrium moisture data. Total phenolic content, anthocyanins content, and in vitro antioxidant capacity were assessed for the juçara seedless pomace (JSP). JSP is rich in monomeric anthocyanins (7.19 to 7.23 mg cyanidin 3-O-glycoside/g dry matter [dm]), presents high antioxidant potential, elevated dietary fibers (72.7% dm), considerable amount of lipids (12.8% dm), low protein content, and ash traces. JS is a rich carbon source (76.91% fibers [dm]; 12.21% amylaceous reserve). Being high in carbohydrates, mainly starch, it can be classified as high starch content flour (juçara seed starch-flour [JSS-F]). JSS-F presented B-type crystallinity and conventional starch-like thermal stability. JSS-F exhibited type III sorption isotherm behavior and the Gugghenheim-Anderson-DeBoer model adequately represented the moisture equilibrium data. As a nutritive source of bioactive compounds and starch, juçara pomace should be regarded as a coproduct to be explored as an alternative natural ingredient to food, pharmaceutical, and chemical industries. PRACTICAL APPLICATION: Juçara agroindustrial residues (pomace and seeds) are a promising source of antioxidants and unconventional starch, which are usually discarded after depulping, representing approximately 74% of the fruits. Juçara pomace can be used to produce flour with marketing potential due to their functional properties and nutritional value. This flour can be incorporated directly into formulations or be used in extraction processes to obtain components of interest, for example, anthocyanins, to be used as a natural food dye. Starch can be extracted from juçara seeds, presenting adequate technological properties for partial replacement of conventional starches.

Spray carnation cultivars of the Mini Tiara series have unique, narrow sword-shaped petals with various colours, and were bred through bud mutations from pink-flowered 'Mini Tiara Pink' (MP) and pink, creamy-flowered 'Mini Tiara Cream' (MC). MP had pelargonidin glucoside as a major pigment, whereas the pale purple-flowered cultivar 'Mini Tiara Lilac' derived from MC had cyanidin glucoside as a major anthocyanin. Furthermore, orange-flowered 'Mini Tiara Sunny' (MS) had both pelargonidin glucoside and chalcononaringenin 2'-glucoside. Thus, the variation in petal colour in the Mini Tiara series was produced by the difference in the amount and types of flavonoid pigment in the petals. Additionally, MS produced several kinds of flower colour mutation and showed a high frequency of flower colour mutation compared with the other cultivars. Therefore, the Mini Tiara series is not only a highly commercial product for the flower market but also useful material for the study of petal colour mutability in carnations.

espanolMediante el uso de diferentes tecnicas cromatograficas se obtuvieron extractos ricos en polifenoles (antocianinas). A partir de los extractos purificados se identificaron por primera vez las antocianinas mayoritarias del fruto de Monnina Obtusifolia: una piroantocianina y tres antocianinas derivadas de delfinidina, cianidina y peonidina. Se evaluo ademas la contribucion relativa de diferentes tipos de fracciones aisladas del fruto (extractos crudos, purificados y compuestos puros) sobre sus propiedades antioxidantes. La antocianina con mayor poder para capturar el radical sintetico ABTS˙+ fue el compuesto derivado de delfinidina. Se encontro que las agliconas con un solo un grupo OH en el anillo B (4'-OH) presentan menor actividad antioxidante, comparado con compuestos que poseen agrupacion 3',4' di-OH sustituidos como los derivados de delfinidina y cianidina. El analisis de la capacidad reductora de Folin-Ciocalteau y la capacidad antioxidante equivalente al trolox de las fracciones aisladas sugieren que el fruto de Monnina Obtusifolia puede ser considerado como una fuente importante de compuestos bioactivos, para su uso en la industria. EnglishThrough the use of different chromatographic techniques extracts rich in polyphenols (anthocyanins) were obtained. From the purified extracts, the main anthocyanins of the Monnina Obtusifolia fruit were identified for the first time: one pyroanthocyanin and three anthocyanins derived from delphinidin, cyanidin and peonidin. The relative contribution of different types of fractions isolated from the fruit (raw extracts, purified and pure compounds) on their antioxidant properties was also evaluated. The anthocyanin with greater power to capture the synthetic radical ABTS˙+ was the compound derived from delphinidin. It was found that aglycones with only one OH group in the B ring (4'-OH) have lower antioxidant activity; compared to compounds possessing 3 ', 4' di-OH substituted group such as delphinidin and cyanidin derivatives. The analysis of the reducing capacity of Folin-Ciocalteau and the antioxidant capacity equivalent to trolox of the isolated fractions suggest that the fruit of Monnina Obtusifolia can be considered as an important source of bioactive compounds, for its use in the industry.

This study aims to link morphological and physico-chemical parameters with maturity stages of Natal plum (Carissa macrocarpa), an edible southern African fruit. Harvesting via an integrative holistic approach is recommended for optimal quality and functional compounds. Fruits at dark green (M1), light green (M2), colour break or pink (M3), red (M4), dark red (M5) stages were harvested in 2016 and 2017 seasons. The principal component analysis illustrated the colour value a* (redness), fruit weight, size (length and width), sugars (glucose and fructose), ascorbic acid content, cyanidin derivatives (cyanidin-3-O-pyranoside, cyanidin 3-O-β-sambubioside, cyanidin-3-O-glucoside), naringenin 4′-O-glucoside, and antioxidant property (FRAP) were higher in the following order of maturity stages M5 > M4 > M3 > M2 > M1. Quercetin 3-O-rhamnosyl galactoside and glucoside were higher in green (h° higher) firm M1 to M3 stages. A strong correlation exists between fruit weight, size, a* value and cyanidin derivatives or naringenin 4′-O-glucoside or ascorbic acid content or antioxidant activity. Thus, the M4 and M5 stages of Natal plum can serve as functional food.

The berries from the native Chilean Gaultheria phillyreifolia and G. poeppigii are appreciated for their sweet taste and aroma. Fruits from both species were investigated for their secondary metabolite composition and antioxidant activity. The extracts were submitted to membrane chromatography to separate anthocyanins from copigments. Four anthocyanins were isolated by counter-current chromatography (CCC) and identified as cyanidin galactoside, cyanidin arabinoside, delphinidin galactoside and delphinidin arabinoside. From the copigments, CCC allowed the separation of quercetin(Q)-3-arabinoside, Q-3-rutinoside Q-3-rhamnoside and 3-caffeoylquinic acid. Additionally, the iridoids monotropein-10-trans-coumarate, monotropein-10-trans-cinnamate and 6α-hydroxy-dihydromonotropein-10-trans-cinnamate were isolated. The latter two iridoids are reported here for the first time. Some 34 other compounds were tentatively identified by HPLC-DAD-ESI-MSn. The antioxidant activity showed differences between anthocyanins and copigments from both species. Main compounds were quantified and submitted to a Partial-Least Square Discriminant Analysis (PLS-DA). This is the first report on the isolation of phytochemicals from the selected Chilean Gaultheria species.

Fall-seeded rye improve their frost resistance during a cold acclimation period in the fall, which is often associated with an accumulation of red/purple-colored anthocyanins in plant tissues. The pigments provide antioxidant activity and are proposed to scavenge excess reactive oxygen species (ROS) and mitigate light stress occurring during cold exposure. The relationship between anthocyanin and winter hardiness in rye (Secale cereale L.) was assessed by analyzing 96 genotypes with varying levels of winter survival. HPLC-QTOF MS/MS analyses of tissue extracts prepared from cold-acclimated plants revealed presence of accumulated anthocyanins in leaves of 74 genotypes and 51 of these showed low levels of anthocyanins presence in crown tissues. An overall higher abundance and diversity of anthocyanins was noted for the most cold-hardy as compared to the less hardy genotypes. A total of 18 anthocyanins originating from the pelargonidin, cyanidin, and delphinidin precursors were identified, of which the glycosylated cyanidins were accumulated in 37 of the 39 most winter hardy genotypes, but only detected in six of the 38 most tender genotypes. The link between anthocyanin concentration and profiles with winter-hardiness levels for the 96 rye genotypes suggested a role for cyanidin-derived anthocyanins in mediating enhanced winter hardiness in rye.

International audience; Plant material rich in anthocyanins has been historically used in traditional medicines, but only recently have the specific pharmacological properties of these compounds been the target of extensive studies. In addition to their potential to modulate the development of various diseases, coloured anthocyanins are valuable natural alternatives commonly used to replace synthetic colourants in food industry. Exploitation of microbial hosts as cell factories is an attractive alternative to extraction of anthocyanins and other flavonoids from plant sources or chemical synthesis. In this study, we present the lactic acid bacterium Lactococcus lactis as an ideal host for the production of high-value plant-derived bioactive anthocyanins using green tea as substrate. Besides the anticipated red-purple compounds cyanidin and delphinidin, orange and yellow pyranoanthocyanidins with unexpected methylation patterns were produced from green tea by engineered L. lactis strains. The pyranoanthocyanins are currently attracting significant interest as one of the most important classes of anthocyanin derivatives and are mainly formed during the aging of wine, contributing to both colour and sensory experience.

The metabolic processes involved in fig production are influenced by macro- and micronutrients supply to the trees during the growing season. Potassium is an essential plant nutrient that influences growth and fruit quality. In this study, the effect of foliar potassium sulphate (K2SO4) application on biochemical composition and antioxidant activity of fig was assessed in cv. Bouhouli, a commonly cultivated cultivar in Djebba (Northwest of Tunisia). Foliar potassium sulphate supply at 2% on Bouhouli trees were applied twice during the fruit growth. Results exhibited that potassium fertilization induces a significant change in total phenolic, flavonoid contents and radical scavenging activity in total fruit and achenes compared to the control. A strong correlation was observed between antioxidant activity and different phenolic compounds. The total fruit and achenes methanol extracts possess, respectively, the highest values of polyphenol by 29.3 and 25.1 mg GAE/g DW compared to the control. Similarly, the flavonoids content was increased in methanol extracts, respectively, by 36 and 48%. HPLC analyses revealed the influence of potassium on concentrations of phenolic compounds in fig sprayed with K2SO4. Among the polyphenols, the chlorogenic acid, cyanidin 3-rutinoside and cyanidin 3,5-diglucoside contents increased from 0.87 to 1.70 mg/g DW under potassium spray, whereas those compounds were not detected in fig achenes. The present study provides clear evidence that potassium sulphate can be used to manipulate total phenolic concentrations in fig with strong antioxidant potential that could be benefits to human health. Thus, potassium sulphate application at 2% could improve nutritional and qualitative attributes of fig.

The occurrence of allergy-mediated inflammatory diseases such as asthma and atopic dermatitis have increased, but comprehensive treatment remains difficult. Previous studies have shown that Schisandra chinensis Baill has antioxidant, antidiabetic, and antitumorigenic effects. Cyanidin 3-rutinoside (CR) is the major anthocyanin pigment of S. chinensis. However, the biological effects of CR have been rarely studied to date. Therefore, the aim of this study was to investigate the regulatory effects of CR on phorbol-12-myristate-13-acetate (PMA)/A23187-induced allergic inflammation in vitro. CR inhibited the secretion of inflammatory cytokines such as interleukin-6 and tumor necrosis factor-α, and it also suppressed the phosphorylation of nuclear factor-kappa B. These results show that CR ameliorated PMA/A23187-induced allergic inflammation via the suppression of inflammatory cytokines in HMC-1 cells. Therefore, CR has potential as a therapeutic agent for allergic diseases.