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13270-61-6

13270-61-6 | 1-Benzopyrylium, 3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-

CAS No: 13270-61-6 Catalog No: AG001115 MDL No:

Product Description

Catalog Number:
AG001115
Chemical Name:
1-Benzopyrylium, 3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-
CAS Number:
13270-61-6
Molecular Formula:
C15H11O7+
Molecular Weight:
303.2436
IUPAC Name:
2-(3,4,5-trihydroxyphenyl)chromenylium-3,5,7-triol
InChI:
InChI=1S/C15H10O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-5H,(H5-,16,17,18,19,20,21)/p+1
InChI Key:
JKHRCGUTYDNCLE-UHFFFAOYSA-O
SMILES:
Oc1cc(O)c2c(c1)[o+]c(c(c2)O)c1cc(O)c(c(c1)O)O
UNII:
031A4BN94T

Properties

Complexity:
380  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
303.05g/mol
Formal Charge:
1  
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
6  
Isotope Atom Count:
0
Molecular Weight:
303.246g/mol
Monoisotopic Mass:
303.05g/mol
Rotatable Bond Count:
1  
Topological Polar Surface Area:
122A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0

Literature

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Delphinidin suppresses ultraviolet B-induced cyclooxygenases-2 expression through inhibition of MAPKK4 and PI-3 kinase. Carcinogenesis 20091101
Chemical composition and phenolic compound profile of mortiño (Vaccinium floribundum Kunth). Journal of agricultural and food chemistry 20090923
The potato R locus codes for dihydroflavonol 4-reductase. TAG. Theoretical and applied genetics. Theoretische und angewandte Genetik 20090901
Molecular identification of 1-Cys peroxiredoxin and anthocyanidin/flavonol 3-O-galactosyltransferase from proanthocyanidin-rich young fruits of persimmon (Diospyros kaki Thunb.). Planta 20090901
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Delphinidin inhibits a broad spectrum of receptor tyrosine kinases of the ErbB and VEGFR family. Molecular nutrition & food research 20090901
Characterization and quantification of anthocyanins in red kiwifruit ( Actinidia spp.). Journal of agricultural and food chemistry 20090812
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Aldose reductase inhibitors from Litchi chinensis Sonn. Journal of enzyme inhibition and medicinal chemistry 20090801
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Bilberry and its main constituents have neuroprotective effects against retinal neuronal damage in vitro and in vivo. Molecular nutrition & food research 20090701
Delphinidin ameliorates beta-amyloid-induced neurotoxicity by inhibiting calcium influx and tau hyperphosphorylation. Bioscience, biotechnology, and biochemistry 20090701
Characterization of anthocyanins in caucasian blueberries (Vaccinium arctostaphylos L.) native to Turkey. Journal of agricultural and food chemistry 20090624
Effect of Vaccinium myrtillus and its polyphenols on angiotensin-converting enzyme activity in human endothelial cells. Journal of agricultural and food chemistry 20090610
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Hypoglycemic activity of a novel anthocyanin-rich formulation from lowbush blueberry, Vaccinium angustifolium Aiton. Phytomedicine : international journal of phytotherapy and phytopharmacology 20090501
Light-induced vegetative anthocyanin pigmentation in Petunia. Journal of experimental botany 20090501
Chemical studies on different color development in blue- and red-colored sepal cells of Hydrangea macrophylla. Bioscience, biotechnology, and biochemistry 20090501
Fyn kinase is a direct molecular target of delphinidin for the inhibition of cyclooxygenase-2 expression induced by tumor necrosis factor-alpha. Biochemical pharmacology 20090401
Delphinidin modulates the DNA-damaging properties of topoisomerase II poisons. Chemical research in toxicology 20090316
Isolation and structural identification of the anthocyanin components of red kiwifruit. Journal of agricultural and food chemistry 20090311
Delphinidin, an anthocyanidin in pigmented fruits and vegetables, induces apoptosis and cell cycle arrest in human colon cancer HCT116 cells. Molecular carcinogenesis 20090301
Post-veraison sunlight exposure induces MYB-mediated transcriptional regulation of anthocyanin and flavonol synthesis in berry skins of Vitis vinifera. Journal of experimental botany 20090301
Anthocyanin composition and oxygen radical scavenging capacity (ORAC) of milled and pearled purple, black, and common barley. Journal of agricultural and food chemistry 20090211
Eugenia jambolana Lam. berry extract inhibits growth and induces apoptosis of human breast cancer but not non-tumorigenic breast cells. Journal of agricultural and food chemistry 20090211
Targeting STAT1 by myricetin and delphinidin provides efficient protection of the heart from ischemia/reperfusion-induced injury. FEBS letters 20090204
Structure of anthocyanins from Eugenia jambolana fruit. Natural product communications 20090201
Enzymatic hemisynthesis of metabolites and conjugates of anthocyanins. Journal of agricultural and food chemistry 20090128
Generation of a predicted protein database from EST data and application to iTRAQ analyses in grape (Vitis vinifera cv. Cabernet Sauvignon) berries at ripening initiation. BMC genomics 20090101
Viscous food matrix influences absorption and excretion but not metabolism of blackcurrant anthocyanins in rats. Journal of food science 20090101
Water deficit alters differentially metabolic pathways affecting important flavor and quality traits in grape berries of Cabernet Sauvignon and Chardonnay. BMC genomics 20090101
In vitro vasorelaxation mechanisms of bioactive compounds extracted from Hibiscus sabdariffa on rat thoracic aorta. Nutrition & metabolism 20090101
Preventive effects of nutritional doses of polyphenolic molecules on cardiac fibrosis associated with metabolic syndrome: involvement of osteopontin and oxidative stress. Journal of agricultural and food chemistry 20081224
Dietary polyphenols identified as intracellular protein kinase A inhibitors. European journal of nutrition 20081201
Structure of commelinin, a blue complex pigment from the blue flowers of Commelina communis. Proceedings of the Japan Academy. Series B, Physical and biological sciences 20081201
Delphinidin attenuates neoplastic transformation in JB6 Cl41 mouse epidermal cells by blocking Raf/mitogen-activated protein kinase kinase/extracellular signal-regulated kinase signaling. Cancer prevention research (Philadelphia, Pa.) 20081201
Structures and antioxidant activity of anthocyanins in many accessions of eggplant and its related species. Journal of agricultural and food chemistry 20081112
Optimization of the extraction of anthocyanin from Bokbunja (Rubus coreanus Miq.) marc produced during traditional wine processing and characterization of the extracts. Bioresource technology 20081101
Delphinidin, a dietary anthocyanidin in pigmented fruits and vegetables: a new weapon to blunt prostate cancer growth. Cell cycle (Georgetown, Tex.) 20081101
Inhibitory effect of fermented papaya preparation on hydroxyl radical generation from methylguanidine. Journal of clinical biochemistry and nutrition 20081101
Molecular structure and antioxidant properties of delphinidin. The journal of physical chemistry. A 20081023
A dietary anthocyanidin delphinidin induces apoptosis of human prostate cancer PC3 cells in vitro and in vivo: involvement of nuclear factor-kappaB signaling. Cancer research 20081015
Impact of delphinidin on the maintenance of DNA integrity in human colon carcinoma cells. Journal of agricultural and food chemistry 20081008
Identification and quantification of phenolic compounds in grapes by HPLC-PDA-ESI-MS on a semimicro separation scale. Journal of agricultural and food chemistry 20081008
Inhibition of epidermal growth factor receptor signaling pathway by delphinidin, an anthocyanidin in pigmented fruits and vegetables. International journal of cancer 20081001
Identification of target genes for a MYB-type anthocyanin regulator in Gerbera hybrida. Journal of experimental botany 20081001
Anthocyanin degradation of blueberry-aronia nectar in glass compared with carton during storage. Journal of food science 20081001
Effects of black soybean [Glycine max (L.) Merr.] seed coats and its anthocyanidins on colonic inflammation and cell proliferation in vitro and in vivo. Journal of agricultural and food chemistry 20080924
Biochemical profiling and chemometric analysis of seventeen UK-grown black currant cultivars. Journal of agricultural and food chemistry 20080827
Delphinidin inhibits cell proliferation and invasion via modulation of Met receptor phosphorylation. Toxicology and applied pharmacology 20080815
Changes of anthocyanins, anthocyanidins, and antioxidant activity in bilberry extract during dry heating. Journal of food science 20080801
Fruit quality, antioxidant capacity, and flavonoid content of organically and conventionally grown blueberries. Journal of agricultural and food chemistry 20080723
Inhibition of proteasome activity by anthocyanins and anthocyanidins. Biochemical and biophysical research communications 20080718
The anthocyanidin delphinidin mobilizes endogenous copper ions from human lymphocytes leading to oxidative degradation of cellular DNA. Toxicology 20080710
Dietary agents for chemoprevention of prostate cancer. Cancer letters 20080708
Multi-substrate flavonol O-glucosyltransferases from strawberry (Fragaria x ananassa) achene and receptacle. Journal of experimental botany 20080701
PGK1 induction by a hydrogen peroxide treatment is suppressed by antioxidants in human colon carcinoma cells. Bioscience, biotechnology, and biochemistry 20080701
Comparison of delphinidin, quercetin and (-)-epigallocatechin-3-gallate as inhibitors of the EGFR and the ErbB2 receptor phosphorylation. Molecular nutrition & food research 20080701
Azuki bean juice lowers serum triglyceride concentrations in healthy young women. Journal of clinical biochemistry and nutrition 20080701
Arabidopsis R2R3-MYB transcription factor AtMYB60 functions as a transcriptional repressor of anthocyanin biosynthesis in lettuce (Lactuca sativa). Plant cell reports 20080601
Characterization and quantification of anthocyanins in grape juices obtained from the grapes cultivated in Korea by HPLC/DAD, HPLC/MS, and HPLC/MS/MS. Journal of food science 20080601
Increasing antioxidant activity and reducing decay of blueberries by essential oils. Journal of agricultural and food chemistry 20080528
Delphinidin, a dietary anthocyanidin, inhibits platelet-derived growth factor ligand/receptor (PDGF/PDGFR) signaling. Carcinogenesis 20080501
Determination of anthocyanins and exploration of relationship between their composition and petal coloration in crape myrtle (Lagerstroemia hybrid). Journal of integrative plant biology 20080501
Protective effects of purple grape juice on carbon tetrachloride-induced oxidative stress in brains of adult Wistar rats. Journal of medicinal food 20080301
Relaxation induced by red wine polyphenolic compounds in rat pulmonary arteries: lack of inhibition by NO-synthase inhibitor. Fundamental & clinical pharmacology 20080201
New polyphenols active on beta-amyloid aggregation. Bioorganic & medicinal chemistry letters 20080115
Effects of anthocyanin and carotenoid combinations on foliage and immature fruit color of Capsicum annuum L. The Journal of heredity 20080101
Molecular aspects of Anthocyanin fruit tomato in relation to high pigment-1. The Journal of heredity 20080101
Cloning and characterization of the UDP-glucose:anthocyanin 5-O-glucosyltransferase gene from blue-flowered gentian. Journal of experimental botany 20080101
Dietary flavonoid sources in Australian adults. Nutrition and cancer 20080101
Analysis of expressed sequence tags from Actinidia: applications of a cross species EST database for gene discovery in the areas of flavor, health, color and ripening. BMC genomics 20080101
(13)C CPMAS NMR and DFT calculations of anthocyanidins. Solid state nuclear magnetic resonance 20080101
[Analysis of anthocyanins in dietary supplements containing blueberry extract]. Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan 20080101
Plasma, tissue and urinary levels of aloin in rats after the administration of pure aloin. Nutrition research and practice 20080101
Identification and quantification of anthocyanin pigments in colored rice. Nutrition research and practice 20080101
Molar absorptivities and reducing capacity of pyranoanthocyanins and other anthocyanins. Journal of agricultural and food chemistry 20071226
Saskatoon and wild blueberries have higher anthocyanin contents than other Manitoba berries. Journal of agricultural and food chemistry 20071226
Development and validation of an LC-MS/MS analysis for simultaneous determination of delphinidin-3-glucoside, cyanidin-3-glucoside and cyanidin-3-(6-malonylglucoside) in human plasma and urine after blood orange juice administration. Journal of separation science 20071201
Anthocyanins present in selected tropical fruits: acerola, jambolão, jussara, and guajiru. Journal of agricultural and food chemistry 20071114
Purification and characterization of UDP-glucose: anthocyanin 3',5'-O-glucosyltransferase from Clitoria ternatea. Planta 20071101
Engineering of the rose flavonoid biosynthetic pathway successfully generated blue-hued flowers accumulating delphinidin. Plant & cell physiology 20071101
Spectrophotometric method for quantitative determination of total anthocyanins and quality characteristics of roselle (Hibiscus sabdariffa). Planta medica 20071101
Survey of bioactive components in Western Canadian berries. Canadian journal of physiology and pharmacology 20071101
Anthocyanins and other polyphenolics in American elderberry (Sambucus canadensis) and European elderberry (S. nigra) cultivars. Journal of the science of food and agriculture 20071101
HPLC-PDA-MS/MS of anthocyanins and carotenoids from dovyalis and tamarillo fruits. Journal of agricultural and food chemistry 20071031
Reactivity of anthocyanins and pyranoanthocyanins. Studies on aromatic hydrogen-deuterium exchange reactions in methanol. Journal of agricultural and food chemistry 20071003
Cytoprotective effect of anthocyanins against doxorubicin-induced toxicity in H9c2 cardiomyocytes in relation to their antioxidant activities. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20071001
Limited stability in cell culture medium and hydrogen peroxide formation affect the growth inhibitory properties of delphinidin and its degradation product gallic acid. Molecular nutrition & food research 20070901
Influence of vine vigor on grape (Vitis vinifera L. Cv. Pinot Noir) anthocyanins. 1. Anthocyanin concentration and composition in fruit. Journal of agricultural and food chemistry 20070808
Influence of vine vigor on grape (Vitis vinifera L. Cv. Pinot Noir) anthocyanins. 2. Anthocyanins and pigmented polymers in wine. Journal of agricultural and food chemistry 20070808
Anthocyanins in berries of ribes including gooseberry cultivars with a high content of acylated pigments. Journal of agricultural and food chemistry 20070711
Biosynthesis of malonylated flavonoid glycosides on the basis of malonyltransferase activity in the petals of Clitoria ternatea. Journal of plant physiology 20070701
Relationship between phenolic compounds, anthocyanins content and antioxidant activity in colored barley germplasm. Journal of agricultural and food chemistry 20070613
Identification of dimeric anthocyanins and new oligomeric pigments in red wine by means of HPLC-DAD-ESI/MSn. Journal of mass spectrometry : JMS 20070601
Anthocyanin-rich grape extract blocks breast cell DNA damage. Journal of medicinal food 20070601
Differential response related to genotoxicity between eggplant (Solanum melanogena) skin aqueous extract and its main purified anthocyanin (delphinidin) in vivo. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20070501
Improved high performance liquid chromatographic separation of anthocyanin compounds from grapes using a novel mixed-mode ion-exchange reversed-phase column. Journal of chromatography. A 20070427
Effect of anthocyanin fractions from selected cultivars of Georgia-grown blueberries on apoptosis and phase II enzymes. Journal of agricultural and food chemistry 20070418
7-Polyacylated delphinidin 3,7-diglucosides from the blue flowers of Leschenaultia cv. Violet Lena. Phytochemistry 20070301
Anthocyanin 3-galactosides from Cornus alba 'Sibirica' with glucosidation of the B-ring. Phytochemistry 20070301
Redirection of anthocyanin synthesis in Osteospermum hybrida by a two-enzyme manipulation strategy. Phytochemistry 20070301
High-molecular-weight polyphenols from oolong tea and black tea: purification, some properties, and role in increasing mitochondrial membrane potential. Bioscience, biotechnology, and biochemistry 20070301
Perianth bottom-specific blue color development in Tulip cv. Murasakizuisho requires ferric ions. Plant & cell physiology 20070201
Anthocyanidins inhibit migration of glioblastoma cells: structure-activity relationship and involvement of the plasminolytic system. Journal of cellular biochemistry 20070101
Delphinidin, an anthocyanidin in pigmented fruits and vegetables, protects human HaCaT keratinocytes and mouse skin against UVB-mediated oxidative stress and apoptosis. The Journal of investigative dermatology 20070101
Comparison of plants used for skin and stomach problems in Trinidad and Tobago with Asian ethnomedicine. Journal of ethnobiology and ethnomedicine 20070101
Ethnoveterinary medicines used for ruminants in British Columbia, Canada. Journal of ethnobiology and ethnomedicine 20070101
Analysis of flavonoids in flower petals of soybean near-isogenic lines for flower and pubescence color genes. The Journal of heredity 20070101
Tissue-specific mRNA expression profiling in grape berry tissues. BMC genomics 20070101
Transcriptional control of anthocyanin biosynthetic genes in extreme phenotypes for berry pigmentation of naturally occurring grapevines. BMC plant biology 20070101
[Analysis of anthocyanin content in bilberry (Vaccinium myrtillus L.) fruit crude drugs by high-performance liquid chromatography method]. Medicina (Kaunas, Lithuania) 20070101
An overview of DNA and RNA bindings to antioxidant flavonoids. Cell biochemistry and biophysics 20070101
Study of diversity of anthocyanin composition in bilberry (Vaccinium myrtillus L.) fruits. Medicina (Kaunas, Lithuania) 20070101
Protective actions of Rubus coreanus ethanol extract on collagenous extracellular matrix in ultraviolet-B irradiation-induced human dermal fibroblasts. Nutrition research and practice 20070101
Flavonoid content of U.S. fruits, vegetables, and nuts. Journal of agricultural and food chemistry 20061227
Phenolics of Arbutus unedo L. (Ericaceae) fruits: identification of anthocyanins and gallic acid derivatives. Journal of agricultural and food chemistry 20061227
Characterization of hemiacetal forms of anthocyanidin 3-O-beta-glycopyranosides. Journal of agricultural and food chemistry 20061213
Effect of shading on accumulation of flavonoid compounds in (Vitis vinifera L.) pinot noir fruit and extraction in a model system. Journal of agricultural and food chemistry 20061101
Monomers of condensed tannins affect the larval exsheathment of parasitic nematodes of ruminants. Journal of agricultural and food chemistry 20061004
Delphinidin and cyanidin inhibit PDGF(AB)-induced VEGF release in vascular smooth muscle cells by preventing activation of p38 MAPK and JNK. British journal of pharmacology 20061001
High-performance liquid chromatography with photodiode array detection (HPLC-DAD)/HPLC-mass spectrometry (MS) profiling of anthocyanins from Andean Mashua Tubers (Tropaeolum tuberosum Ruíz and Pavón) and their contribution to the overall antioxidant activity. Journal of agricultural and food chemistry 20060920
Effect of clarification techniques and rat intestinal extract incubation on phenolic composition and antioxidant activity of black currant juice. Journal of agricultural and food chemistry 20060906
Bioavailability and tissue distribution of anthocyanins in bilberry (Vaccinium myrtillus L.) extract in rats. Journal of agricultural and food chemistry 20060906
Superoxide radical- and peroxynitrite-scavenging activity of anthocyanins; structure-activity relationship and their synergism. Free radical research 20060901
Bioactive depsides and anthocyanins from jaboticaba (Myrciaria cauliflora). Journal of natural products 20060801
Comparison of the anthocyanin composition during ripening of Syrah grapes grown using organic or conventional agricultural practices. Journal of agricultural and food chemistry 20060726
Gastrointestinal uptake of nasunin, acylated anthocyanin in eggplant. Journal of agricultural and food chemistry 20060726
Anthocyanin composition in black, blue, pink, purple, and red cereal grains. Journal of agricultural and food chemistry 20060628
Polyphenols in wild and weedy Mexican common beans (Phaseolus vulgaris L.). Journal of agricultural and food chemistry 20060614
Concentrations of anthocyanins in common foods in the United States and estimation of normal consumption. Journal of agricultural and food chemistry 20060531
Preparative isolation and NMR characterization of carboxypyranoanthocyanins. Journal of agricultural and food chemistry 20060517
Delphinidin, a dietary anthocyanidin, inhibits vascular endothelial growth factor receptor-2 phosphorylation. Carcinogenesis 20060501
Characterization and quantification of anthocyanins in selected artichoke (Cynara scolymus L.) cultivars by HPLC-DAD-ESI-MSn. Analytical and bioanalytical chemistry 20060401
Two different transposable elements inserted in flavonoid 3',5'-hydroxylase gene contribute to pink flower coloration in Gentiana scabra. Molecular genetics and genomics : MGG 20060301
Interaction of antioxidant flavonoids with tRNA: intercalation or external binding and comparison with flavonoid-DNA adducts. DNA and cell biology 20060201
New flavanol-anthocyanin condensed pigments and anthocyanin composition in guatemalan beans (Phaseolus spp.). Journal of agricultural and food chemistry 20060125
Anthocyanidins decrease endothelin-1 production and increase endothelial nitric oxide synthase in human endothelial cells. Molecular nutrition & food research 20060101
Natural flavonoids are potent inhibitors of glycogen phosphorylase. Molecular nutrition & food research 20060101
Colour variation in red grapevines (Vitis vinifera L.): genomic organisation, expression of flavonoid 3'-hydroxylase, flavonoid 3',5'-hydroxylase genes and related metabolite profiling of red cyanidin-/blue delphinidin-based anthocyanins in berry skin. BMC genomics 20060101
Anthocyanins in berries of Maqui (Aristotelia chilensis (Mol.) Stuntz). Phytochemical analysis : PCA 20060101
Electron spin resonance spectroscopy studies on the free radical scavenging activity of wine anthocyanins and pyranoanthocyanins. Molecular nutrition & food research 20051201
Flavonoids in flowers of 16 Kalanchoë blossfeldiana varieties. Phytochemistry 20051201
Nasunin from eggplant consists of cis-trans isomers of delphinidin 3-[4-(p-coumaroyl)-L-rhamnosyl (1-->6)glucopyranoside]-5-glucopyranoside. Journal of agricultural and food chemistry 20051130
Anthocyanins from red wine--their stability under simulated gastrointestinal digestion. Phytochemistry 20051101
Screening for anthocyanins using high-performance liquid chromatography coupled to electrospray ionization tandem mass spectrometry with precursor-ion analysis, product-ion analysis, common-neutral-loss analysis, and selected reaction monitoring. Journal of chromatography. A 20051014
Anthocyanin-flavanol condensation products from black currant (Ribes nigrum L.). Journal of agricultural and food chemistry 20051005
Effects of anthocyanidin on the inhibition of proliferation and induction of apoptosis in human gastric adenocarcinoma cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20051001
Anthocyanidins modulate the activity of human DNA topoisomerases I and II and affect cellular DNA integrity. Chemical research in toxicology 20050901
Evaluation of the phenolic content in the aerial parts of different varieties of Cichorium intybus L. Journal of agricultural and food chemistry 20050810
Anthocyanidins inhibit cyclooxygenase-2 expression in LPS-evoked macrophages: structure-activity relationship and molecular mechanisms involved. Biochemical pharmacology 20050801
Delphinidin 3-sambubioside, a Hibiscus anthocyanin, induces apoptosis in human leukemia cells through reactive oxygen species-mediated mitochondrial pathway. Archives of biochemistry and biophysics 20050801
Delphinidin 3-O-(2-O-beta-D-Glucopyranosyl-alpha-l-arabinopyranoside): a novel anthocyanin identified in Beluga black lentils. Journal of agricultural and food chemistry 20050615
DNA interaction with naturally occurring antioxidant flavonoids quercetin, kaempferol, and delphinidin. Journal of biomolecular structure & dynamics 20050601
Some advances in the knowledge of grape, wine and distillates chemistry as achieved by mass spectrometry. Journal of mass spectrometry : JMS 20050601
Preformed and induced chemical resistance of tea leaf against Exobasidium vexans infection. Journal of chemical ecology 20050601
Systematic identification and characterization of anthocyanins by HPLC-ESI-MS/MS in common foods in the United States: fruits and berries. Journal of agricultural and food chemistry 20050406
Anthocyanin antioxidant activity and partition behavior in whey protein emulsion. Journal of agricultural and food chemistry 20050323
Identification of anthocyanins in Rhamnus alaternus L. berries. Journal of agricultural and food chemistry 20050309
Induction of apoptosis by the Anthocyanidins through regulation of Bcl-2 gene and activation of c-Jun N-terminal kinase cascade in hepatoma cells. Journal of agricultural and food chemistry 20050309
A blend of polyphenolic compounds explains the stimulatory effect of red wine on human endothelial NO synthase. Nitric oxide : biology and chemistry 20050301
Human tumor cell growth inhibition by nontoxic anthocyanidins, the pigments in fruits and vegetables. Life sciences 20050211
Insulin secretion by bioactive anthocyanins and anthocyanidins present in fruits. Journal of agricultural and food chemistry 20050112
Pomegranate fruit extract modulates UV-B-mediated phosphorylation of mitogen-activated protein kinases and activation of nuclear factor kappa B in normal human epidermal keratinocytes paragraph sign. Photochemistry and photobiology 20050101
Anthocyanins protect against A2E photooxidation and membrane permeabilization in retinal pigment epithelial cells. Photochemistry and photobiology 20050101
Characterization of anthocyanins and pyranoanthocyanins from blood orange [Citrus sinensis (L.) Osbeck] juice. Journal of agricultural and food chemistry 20041201
Comparison of anthocyanin pigment and other phenolic compounds of Vaccinium membranaceum and Vaccinium ovatum native to the Pacific Northwest of North America. Journal of agricultural and food chemistry 20041117
Identification of flavonoids in Hakmeitau beans (Vigna sinensis) by high-performance liquid chromatography-electrospray mass spectrometry (LC-ESI/MS). Journal of agricultural and food chemistry 20041103
Identification of delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3'-O-beta-glucoside, a postulated intermediate in the biosynthesis of ternatin C5 in the blue petals of Clitoria ternatea (butterfly pea). Chemistry & biodiversity 20041101
Liquid chromatographic-mass spectrometric analysis of anthocyanin composition of dark blue bee pollen from Echium plantagineum. Journal of chromatography. A 20041029
Liquid chromatography-mass spectrometry identification of anthocyanins of isla oca (Oxalis tuberosa, Mol.) tubers. Journal of chromatography. A 20041029
The substitution pattern of anthocyanidins affects different cellular signaling cascades regulating cell proliferation. Molecular nutrition & food research 20040901
Effect of the maceration technique on the relationships between anthocyanin composition and objective color of Syrah wines. Journal of agricultural and food chemistry 20040811
Delphinidin accumulation is associated with abnormal flower development in petunias. Phytochemistry 20040801
Antioxidant and cellular activities of anthocyanins and their corresponding vitisins A--studies in platelets, monocytes, and human endothelial cells. Journal of agricultural and food chemistry 20040602
Structural dependence of HPLC separation pattern of anthocyanins from Bilberry (Vaccinium myrtillus L.). Chemical & pharmaceutical bulletin 20040501
Production of highly 13C-labeled polyphenols in Vitis vinifera cell bioreactor cultures. Journal of biotechnology 20040429
Absorption and metabolism of delphinidin 3-O-beta-D-glucopyranoside in rats. Free radical biology & medicine 20040401
Comparison of HPLC methods for determination of anthocyanins and anthocyanidins in bilberry extracts. Journal of agricultural and food chemistry 20040225
Fruit maturity and juice extraction influences ellagic acid derivatives and other antioxidant polyphenolics in muscadine grapes. Journal of agricultural and food chemistry 20040128
Anthocyanidins inhibit activator protein 1 activity and cell transformation: structure-activity relationship and molecular mechanisms. Carcinogenesis 20040101
Absorption and metabolism of delphinidin 3-O-beta-D-glucoside in rats. BioFactors (Oxford, England) 20040101
Antioxidant activity of extracts, condensed tannin fractions, and pure flavonoids from Phaseolus vulgaris L. seed coat color genotypes. Journal of agricultural and food chemistry 20031231
Anthocyanin profile of Korean cultivated kidney bean (Phaseolus vulgaris L.). Journal of agricultural and food chemistry 20031119
Flavonoid composition related to petal color in different lines of Clitoria ternatea. Phytochemistry 20031101
Cloning and expression of a putative cytochrome P450 gene that influences the colour of Phalaenopsis flowers. Biotechnology letters 20031101
Quantification of anthocyanins in commercial black currant juices by simple high-performance liquid chromatography. Investigation of their pH stability and antioxidative potency. Journal of agricultural and food chemistry 20030924
Anthocyanidins induce apoptosis in human promyelocytic leukemia cells: structure-activity relationship and mechanisms involved. International journal of oncology 20030901
Antioxidant activity of the anthocyanin from carrot (Daucus carota) callus culture. International journal of food sciences and nutrition 20030901
New perspectives on proanthocyanidin biochemistry and molecular regulation. Phytochemistry 20030901
Characterization of anthocyanins from the fruits of baguaçu (Eugenia umbelliflora Berg). Journal of agricultural and food chemistry 20030827
Involvement of cyclin-dependent pathway in the inhibitory effect of delphinidin on angiogenesis. Cardiovascular research 20030801
Biochemical and molecular characterization of a novel UDP-glucose:anthocyanin 3'-O-glucosyltransferase, a key enzyme for blue anthocyanin biosynthesis, from gentian. Plant physiology 20030701
Delphinidin, an active compound of red wine, inhibits endothelial cell apoptosis via nitric oxide pathway and regulation of calcium homeostasis. British journal of pharmacology 20030701
Inhibition of linoleic acid hydroperoxide-induced toxicity in cultured human fibroblasts by anthocyanidins. Bioscience, biotechnology, and biochemistry 20030601
Anthocyanin composition of Cabernet Sauvignon and Tempranillo grapes at different stages of ripening. Journal of agricultural and food chemistry 20030521
A rationale for the shift in colour towards blue in transgenic carnation flowers expressing the flavonoid 3',5'-hydroxylase gene. Phytochemistry 20030501
Bioavailability of anthocyanidin-3-glucosides following consumption of red wine and red grape juice. Canadian journal of physiology and pharmacology 20030501
Characterization of anthocyanins in grape juices by ion trap liquid chromatography-mass spectrometry. Journal of agricultural and food chemistry 20030326
Sepal color variation of Hydrangea macrophylla and vacuolar pH measured with a proton-selective microelectrode. Plant & cell physiology 20030301
Delphinidin inhibits endothelial cell proliferation and cell cycle progression through a transient activation of ERK-1/-2. Biochemical pharmacology 20030215
Anthocyanins protect against DNA damage induced by tert-butyl-hydroperoxide in rat smooth muscle and hepatoma cells. Mutation research 20030205
Antioxidant activity of anthocyanins and their aglycons. Journal of agricultural and food chemistry 20030129
Induction of apoptosis in cancer cells by Bilberry (Vaccinium myrtillus) and the anthocyanins. Journal of agricultural and food chemistry 20030101
Selective accumulation of delphinidin derivatives in tobacco using a putative flavonoid 3',5'-hydroxylase cDNA from Campanula medium. Bioscience, biotechnology, and biochemistry 20030101
Purification of anthocyanins from species of Banksia and Acacia using high-voltage paper electrophoresis. Phytochemical analysis : PCA 20030101
Inhibition of proliferation of human cancer cells and cyclooxygenase enzymes by anthocyanidins and catechins. Nutrition and cancer 20030101
[Polyphenols and anthocyanins in fruits, grapes juices and wines, and evaluation of their antioxidant activity]. Medicina (Kaunas, Lithuania) 20030101
Absorption of anthocyanins from blueberries and serum antioxidant status in human subjects. Journal of agricultural and food chemistry 20021218
Varietal differences among the polyphenol profiles of seven table grape cultivars studied by LC-DAD-MS-MS. Journal of agricultural and food chemistry 20020925
Antioxidant activity of black currant anthocyanin aglycons and their glycosides measured by chemiluminescence in a neutral pH region and in human plasma. Journal of agricultural and food chemistry 20020828
Anthocyanins from flowers of Cichorium intybus. Phytochemistry 20020601
Acylated anthocyanins from the blue-violet flowers of Anemone coronaria. Phytochemistry 20020601
Effects of prodelphinidins isolated from Ribes nigrum on chondrocyte metabolism and COX activity. Naunyn-Schmiedeberg's archives of pharmacology 20020601
Ellagic acid and flavonoid antioxidant content of muscadine wine and juice. Journal of agricultural and food chemistry 20020522
Anthocyanins from black currants (Ribes nigrum L.). Journal of agricultural and food chemistry 20020522
Characterization, quantification, and bioactivities of anthocyanins in Cornus species. Journal of agricultural and food chemistry 20020424
Flavonoid and carbohydrate contents in Tropea red onions: effects of homelike peeling and storage. Journal of agricultural and food chemistry 20020327
Red wine polyphenols increase calcium in bovine aortic endothelial cells: a basis to elucidate signalling pathways leading to nitric oxide production. British journal of pharmacology 20020301
Inhibitory effects of anthocyanins and other phenolic compounds on nitric oxide production in LPS/IFN-gamma-activated RAW 264.7 macrophages. Journal of agricultural and food chemistry 20020213
Antioxidant activities of pomegranate fruit extract and its anthocyanidins: delphinidin, cyanidin, and pelargonidin. Journal of agricultural and food chemistry 20020102
Antioxidant properties of gallocatechin and prodelphinidins from pomegranate peel. Redox report : communications in free radical research 20020101
Identification and quantification of galloyl derivatives, flavonoid glycosides and anthocyanins in leaves of Pistacia lentiscus L. Phytochemical analysis : PCA 20020101
Anthocyanin composition of the fruit of Coriaria myrtifolia L. Phytochemical analysis : PCA 20020101
Anthocyanin-rich extract decreases indices of lipid peroxidation and DNA damage in vitamin E-depleted rats. Free radical biology & medicine 20011101
Deep blue anthocyanins from blue Dianella berries. Phytochemistry 20011101
Acylated anthocyanidin 3-sophoroside-5-glucosides from Ajuga reptans flowers and the corresponding cell cultures. Phytochemistry 20011001
Determination of anthocyanidins in berries and red wine by high-performance liquid chromatography. Journal of agricultural and food chemistry 20010901
Preparative-scale isolation of four anthocyanin components of black currant (Ribes nigrum L.) fruits. Journal of agricultural and food chemistry 20010301
Orally administered delphinidin 3-rutinoside and cyanidin 3-rutinoside are directly absorbed in rats and humans and appear in the blood as the intact forms. Journal of agricultural and food chemistry 20010301
Anthocyanins from red flower tea (Benibana-cha), Camellia sinensis. Phytochemistry 20010201
The anthocyanidins cyanidin and delphinidin are potent inhibitors of the epidermal growth-factor receptor. Journal of agricultural and food chemistry 20010201
Acid mediated hydrolysis of blueberry anthocyanins. Chemical & pharmaceutical bulletin 20010101
Proanthocyanidins of mountain birch leaves: quantification and properties. Phytochemical analysis : PCA 20010101

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