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Molecules (Basel, Switzerland) Feb 2012Originating in the grapes, anthocyanins and their derivatives are the crucial pigments responsible for the red wine color. During wine maturation and aging, the... (Review)
Review
Originating in the grapes, anthocyanins and their derivatives are the crucial pigments responsible for the red wine color. During wine maturation and aging, the concentration of monomeric anthocyanins declines constantly, while numerous more complex and stable anthocyanin derived pigments are formed, mainly including pyranoanthocyanins, polymeric anthocyanins produced from condensation between anthocyanin and/or flavan-3-ols directly or mediated by aldehydes. Correspondingly, their structural modifications result in a characteristic variation of color, from purple-red color in young red wines to brick-red hue of the aged. Because of the extreme complexity of chemical compounds involved, many investigations have been made using model solutions of know composition rather than wine. Thus, there is a large amount of research still required to obtain an overall perspective of the anthocyanin composition and its change with time in red wines. Future findings may well greatly revise our current interpretation of the color in red wines. This paper summarizes the most recent advances in the studies of the anthocyanins derived pigments in red wines, as well as their color evolution.
Topics: Anthocyanins; Color; Mass Spectrometry; Polymers; Wine
PubMed: 23442981
DOI: 10.3390/molecules17021483 -
Anthocyanin regulatory and structural genes associated with violet flower color of Matthiola incana.Planta Feb 2020MiMYB1 and MibHLH2 play key roles in anthocyanin biosynthesis in Matthiola incana flowers. We established a transient expression system using Turnip mosaic virus vector...
MiMYB1 and MibHLH2 play key roles in anthocyanin biosynthesis in Matthiola incana flowers. We established a transient expression system using Turnip mosaic virus vector in M. incana. Garden stock (Matthiola incana (L.) R. Br.) is a popular flowering plant observed from winter to spring in Japan. Here we observed that anthocyanin accumulation in 'Vintage Lavender' increased with flower development, whereas flavonol accumulation remained constant throughout flower development. We obtained five transcription factor genes, MiMYB1, MibHLH1, MibHLH2, MiWDR1, and MiWDR2, from M. incana floral cDNA contigs. Yeast two-hybrid analyses revealed that MiMYB1 interacted with MibHLH1, MibHLH2, and MiWDR1, but MiWDR2 did not interact with any transcription factor. Expression levels of MiMYB1 and MibHLH2 increased in petals during floral bud development. Their expression profiles correlated well with the temporal profiles of MiF3'H, MiDFR, MiANS, and Mi3GT transcripts and anthocyanin accumulation profile. On the other hand, MibHLH1 was expressed weakly in all organs of 'Vintage Lavender'. However, high expression levels of MibHLH1 were detected in petals of other cultivars with higher levels of anthocyanin accumulation than 'Vintage Lavender'. MiWDR1 and MiWDR2 maintained constant expression levels in petals during flower development and vegetative organs. Transient MiMYB1 expression in 1-month-old M. incana seedlings using a Turnip mosaic virus vector activated transcription of the endogenous anthocyanin biosynthetic genes MiF3'H, MiDFR, and MiANS and induced ectopic anthocyanin accumulation in leaves. Therefore, MiMYB1 possibly interacts with MibHLH2 and MiWDR1, and this trimeric protein complex activates the transcription of anthocyanin biosynthetic genes in M. incana flowers. Moreover, MibHLH1 acts as an enhancer of anthocyanin biosynthesis with the MiMYB1-MibHLH2-MiWDR1 complex. This study revealed the molecular mechanism involved in the regulation of anthocyanin accumulation levels in M. incana flowers.
Topics: Anthocyanins; Biosynthetic Pathways; Brassicaceae; Flavonoids; Flowers; Gene Expression Regulation, Plant; Genes, Plant; Pigmentation; Potyvirus; Protein Binding; Seedlings; Time Factors; Nicotiana
PubMed: 32036464
DOI: 10.1007/s00425-020-03351-z -
Molecules (Basel, Switzerland) Nov 2019Research on the bioavailability of anthocyanins has focused, historically, on the non-flavonoid (C-C) products that arise from anthocyanins in vivo. However, this review... (Review)
Review
Research on the bioavailability of anthocyanins has focused, historically, on the non-flavonoid (C-C) products that arise from anthocyanins in vivo. However, this review focuses on the products of anthocyanins that still possess the flavonoid structure (C-C-C). Described herein are aspects of the in vivo pool of C-C-C anthocyanin-derived intermediates. Properties related to molecular size, shape, and polarity conveyed by six major anthocyanidin structures are discussed. The presence of a glycoside or not, and a variety of possible phase 2 conjugates, gives rise to a chemically diverse pool of C-C-C intermediates. Chemical properties influence the in vivo stability of anthocyanin-derived products, as well as their suitability as a substrate for xenobiotic conjugation and transport, and their association with the biomatrix. The flavonoid structure is associated with bioactivity and the particular properties of these C-C-C products of anthocyanins determines their deposition in the body, which may influence in vivo processes and ultimately health outcomes.
Topics: Animals; Anthocyanins; Biological Availability; Humans; Xenobiotics
PubMed: 31703276
DOI: 10.3390/molecules24224024 -
Chemical Reviews May 2016Natural anthocyanin pigments/dyes and phenolic copigments/co-dyes form noncovalent complexes, which stabilize and modulate (in particular blue, violet, and red) colors... (Review)
Review
Natural anthocyanin pigments/dyes and phenolic copigments/co-dyes form noncovalent complexes, which stabilize and modulate (in particular blue, violet, and red) colors in flowers, berries, and food products derived from them (including wines, jams, purees, and syrups). This noncovalent association and their electronic and optical implications constitute the copigmentation phenomenon. Over the past decade, experimental and theoretical studies have enabled a molecular understanding of copigmentation. This review revisits this phenomenon to provide a comprehensive description of the nature of binding (the dispersion and electrostatic components of π-π stacking, the hydrophobic effect, and possible hydrogen-bonding between pigment and copigment) and of spectral modifications occurring in copigmentation complexes, in which charge transfer plays an important role. Particular attention is paid to applications of copigmentation in food chemistry.
Topics: Anthocyanins; Color; Coloring Agents; Hydrogen Bonding; Phenols; Pigments, Biological
PubMed: 26959943
DOI: 10.1021/acs.chemrev.5b00507 -
Plant Signaling & Behavior Jan 2011Light is the ultimate energy source for photo-autotrophs on earth. For green plants, however, it can also be toxic under certain stressful environmental conditions and... (Review)
Review
Light is the ultimate energy source for photo-autotrophs on earth. For green plants, however, it can also be toxic under certain stressful environmental conditions and at critical developmental stages. Anthocyanins, a class of flavonoids, act as an effective screening mechanism that allows plant survival and proliferation under occasional periods of harmful irradiation through modulation of light absorption. Apart from light-sensing through photoreceptors such as phytochrome and cryptochrome, plants use the photosynthetic electron transfer (PET) chain to integrate light information. The redox status of the plastoquinone (PQ) pool of the PET chain regulates anthocyanin biosynthesis genes, together with the plant hormone ethylene and plant hormone-like sugars. A complex signaling apparatus in acyanic cells appears to transduce information to cyanic cells to regulate anthocyanin production through an intercellular signaling pathway that remains largely uncharacterized. This review will highlight recent advances in this field and their implications for the regulation of anthocyanin pigmentation.
Topics: Anthocyanins; Arabidopsis; Ethylenes; Light; Photosynthesis; Pigmentation
PubMed: 21248473
DOI: 10.4161/psb.6.1.14082 -
Genes Aug 2020Purple or black carrots ( ssp. var. Alef) are characterized by their dark purple- to black-colored roots, owing their appearance to high anthocyanin concentrations. In... (Review)
Review
Purple or black carrots ( ssp. var. Alef) are characterized by their dark purple- to black-colored roots, owing their appearance to high anthocyanin concentrations. In recent years, there has been increasing interest in the use of black carrot anthocyanins as natural food dyes. Black carrot roots contain large quantities of mono-acylated anthocyanins, which impart a measure of heat-, light- and pH-stability, enhancing the color-stability of food products over their shelf-life. The genetic pathway controlling anthocyanin biosynthesis appears well conserved among land plants; however, different variants of anthocyanin-related genes between cultivars results in tissue-specific accumulations of purple pigments. Thus, broad genetic variations of anthocyanin profile, and tissue-specific distributions in carrot tissues and organs, can be observed, and the ratio of acylated to non-acylated anthocyanins varies significantly in the purple carrot germplasm. Additionally, anthocyanins synthesis can also be influenced by a wide range of external factors, such as abiotic stressors and/or chemical elicitors, directly affecting the anthocyanin yield and stability potential in food and beverage applications. In this study, we critically review and discuss the current knowledge on anthocyanin diversity, genetics and the molecular mechanisms controlling anthocyanin accumulation in carrots. We also provide a view of the current knowledge gaps and advancement needs as regards developing and applying innovative molecular tools to improve the yield, product performance and stability of carrot anthocyanin for use as a natural food colorant.
Topics: Anthocyanins; Biological Products; Chemical Phenomena; Daucus carota; Food Coloring Agents; Food Industry; Gene Expression Regulation, Plant; Genetic Association Studies; Genome, Plant; Genomics; Pigmentation; Plant Proteins; Quantitative Trait, Heritable
PubMed: 32784714
DOI: 10.3390/genes11080906 -
The New Phytologist Dec 2022Due to their sessile nature, plants cannot escape adverse environmental conditions and evolved mechanisms to cope with sudden environmental changes. The reaction to... (Review)
Review
Due to their sessile nature, plants cannot escape adverse environmental conditions and evolved mechanisms to cope with sudden environmental changes. The reaction to variations in abiotic factors, also summarized as acclimation response, affects all layers of cellular functions and involves rapid modification of enzymatic activities, the metabolome, proteome and transcriptome on different timescales. One trait of plants acclimating to high light (HL) is the rapid transcriptional activation of the flavonoid biosynthesis (FB) pathway resulting in the accumulation of photoprotective and antioxidative flavonoids, such as flavonols and anthocyanins, in the leaf tissue. Although enormous progress has been made in identifying enzymes and transcriptional regulators of FB by forward and reverse genetic approaches in the past, the signals and signalling pathways permitting the conditional activation of FB in HL are still debated. With this Tansley Insight, we summarize the current knowledge on the proposed signals and downstream factors involved in regulating FB and will discuss their contribution to, particularly, HL-induced accumulation of anthocyanins.
Topics: Anthocyanins; Gene Expression Regulation, Plant; Plant Proteins; Flavonoids; Transcriptome; Plants
PubMed: 36110042
DOI: 10.1111/nph.18488 -
BMC Plant Biology Jan 2022Fruits are vital food resources as they are loaded with bioactive compounds varying with different stages of ripening. As the fruit ripens, a dynamic color change is... (Review)
Review
BACKGROUND
Fruits are vital food resources as they are loaded with bioactive compounds varying with different stages of ripening. As the fruit ripens, a dynamic color change is observed from green to yellow to red due to the biosynthesis of pigments like chlorophyll, carotenoids, and anthocyanins. Apart from making the fruit attractive and being a visual indicator of the ripening status, pigments add value to a ripened fruit by making them a source of nutraceuticals and industrial products. As the fruit matures, it undergoes biochemical changes which alter the pigment composition of fruits.
RESULTS
The synthesis, degradation and retention pathways of fruit pigments are mediated by hormonal, genetic, and environmental factors. Manipulation of the underlying regulatory mechanisms during fruit ripening suggests ways to enhance the desired pigments in fruits by biotechnological interventions. Here we report, in-depth insight into the dynamics of a pigment change in ripening and the regulatory mechanisms in action.
CONCLUSIONS
This review emphasizes the role of pigments as an asset to a ripened fruit as they augment the nutritive value, antioxidant levels and the net carbon gain of fruits; pigments are a source for fruit biofortification have tremendous industrial value along with being a tool to predict the harvest. This report will be of great utility to the harvesters, traders, consumers, and natural product divisions to extract the leading nutraceutical and industrial potential of preferred pigments biosynthesized at different fruit ripening stages.
Topics: Anthocyanins; Carotenoids; Fruit; Gene Expression Regulation, Plant; Genes, Plant; Pigments, Biological
PubMed: 35016620
DOI: 10.1186/s12870-021-03411-w -
The Plant Journal : For Cell and... Jul 2021Anthocyanins play an important role in the growth of plants, and are beneficial to human health. In plants, the MYB-bHLH-WD40 (MBW) complex activates the genes for...
Anthocyanins play an important role in the growth of plants, and are beneficial to human health. In plants, the MYB-bHLH-WD40 (MBW) complex activates the genes for anthocyanin biosynthesis. However, in rice, the WD40 regulators remain to be conclusively identified. Here, a crucial anthocyanin biosynthesis gene was fine mapped to a 43.4-kb genomic region on chromosome 2, and a WD40 gene OsTTG1 (Oryza sativa TRANSPARENT TESTA GLABRA1) was identified as ideal candidate gene. Subsequently, a homozygous mutant (osttg1) generated by CRISPR/Cas9 showed significantly decreased anthocyanin accumulation in various rice organs. OsTTG1 was highly expressed in various rice tissues after germination, and it was affected by light and temperature. OsTTG1 protein was localized to the nucleus, and can physically interact with Kala4, OsC1, OsDFR and Rc. Furthermore, a total of 59 hub transcription factor genes might affect rice anthocyanin biosynthesis, and LOC_Os01g28680 and LOC_Os02g32430 could have functional redundancy with OsTTG1. Phylogenetic analysis indicated that directional selection has driven the evolutionary divergence of the indica and japonica OsTTG1 alleles. Our results suggest that OsTTG1 is a vital regulator of anthocyanin biosynthesis, and an important gene resource for the genetic engineering of anthocyanin biosynthesis in rice and other plants.
Topics: Anthocyanins; Gene Expression Regulation, Plant; Haplotypes; Oryza; Phylogeny; Plant Proteins; Plants, Genetically Modified; Polymorphism, Single Nucleotide; Selection, Genetic; Transcription Factors; Two-Hybrid System Techniques; WD40 Repeats
PubMed: 33884679
DOI: 10.1111/tpj.15285 -
Molecules (Basel, Switzerland) Sep 2019Anthocyanin (AC) is widely used as supplement of eye health in Europe and in East Asia. In this review, I describe AC effects to clarify the mechanism is important in... (Review)
Review
Anthocyanin (AC) is widely used as supplement of eye health in Europe and in East Asia. In this review, I describe AC effects to clarify the mechanism is important in order to understand the effects of AC on vision health. The bioavailability of AC is quite low but, reported as intact form and many kinds of metabolite. And AC passes through the blood-aqueous fluid barrier and blood-retinal barrier. In vitro study, AC had a relaxing effect on ciliary muscle which is important to treat both myopia and glaucoma. And AC stimulate the regeneration of rhodopsin in frog rod outer segment. Furthermore, AC could inhibit the axial length and ocular length elongation in a negative lens-induced chick myopia model. In addition, we summarized clinical studies of AC intake improved dark adaptation and transient myopic shift and the improvement on retinal blood circulation in normal tension glaucoma patients.
Topics: Animals; Anthocyanins; Biological Availability; Dark Adaptation; Eye; Tissue Distribution; Vision, Ocular
PubMed: 31514422
DOI: 10.3390/molecules24183311