The chemistry of anthocyanins, anthocyanidins and related flavylium salts

[1]  C. F. Timberlake,et al.  Flavylium salts, anthocyanidins and anthocyanins. I. Structural transformations in acid solutions. , 1967, Journal of the science of food and agriculture.

[2]  Z. Kertesz,et al.  THE KINETICS OF THE OXIDATION OF STRAWBERRY ANTHOCYANIN BY HYDROGEN PEROXIDE , 1952 .

[3]  The Synthesis and Structure of Benzopyrylium (Chromylium) Salts. , 1936 .

[4]  L. Jurd Anthocyanidins and related compounds—XVII : Reactions of flavylium salts and 2-hydroxychalcones with hydroxylamine and hydrazine , 1975 .

[5]  J. Harborne,et al.  Two distinctive anthocyanin patterns in the commelinaceae , 1980 .

[6]  L. Jurd Anthocyanidins and related compounds—VIII : Condensation reactions of flavylium salts with 5,5-dimethyl-1,3-cyclohexanedione in acid solutions , 1965 .

[7]  L. Zechmeister,et al.  Synthese des Pelargonidins und Cyanidins , 1924 .

[8]  R. Brouillard,et al.  Mechanism of the structural transformations of anthocyanins in acidic media , 1977 .

[9]  R. Brouillard,et al.  Chemistry of anthocyanin pigments. 3. Relaxation amplitudes in pH-jump experiments , 1978 .

[10]  W. Ollis,et al.  The neoflavanoid group of natural products—III: The synthesis and nuclear magnetic resonance spectra of the dalbergiones , 1965 .

[11]  Marguerite M. Wilkinson,et al.  High-pressure liquid chromatography of anthocyanidins , 1977 .

[12]  G. Hrazdina,et al.  CO‐PIGMENTATION OF ANTHOCYANINS UNDER PHYSIOLOGICAL CONDITIONS , 1978 .

[13]  G. Hrazdina,et al.  High-pressure liquid chromatographic separation of 3-glucosides, 3,5-diglucosides, 3-(6-O-p-coumaryl)glucosides and 3-(6-O-p-coumarylglucoside)-5-glucosides of anthocyanidins , 1978 .

[14]  B. Bielski,et al.  Kinetics of the interaction of HO/sub 2/ and O/sub 2//sup -/ radicals with hydrogen peroxide. The Haber--Weiss reaction. [Gamma radiation] , 1979 .

[15]  R. Wrolstad,et al.  Polyvinylpyrrolidone column chromatography of strawberry, rhubarb, and raspberry anthocyanins , 1971 .

[16]  N. Saitǒ,et al.  Cyanidin bromide monohydrate (3,5,7,3',4'-pentahydroxyflavylium bromide monohydrate) , 1977 .

[17]  T. King,et al.  813. The synthesis of flavan-2 : 3-diols (dihydro-α : 2-dihydroxy-chalcones) , 1958 .

[18]  J. G. Sweeny,et al.  Synthesis of anthocyanidins—I: The oxidative generation of flavylium cations using benzoquinones , 1977 .

[19]  C. F. Timberlake,et al.  Fast atom bombardment mass spectrometry of the anthocyanins violanin and platyconin , 1983 .

[20]  T. Goto,et al.  Heavenly blue anthocyanin II trans-4-0-(6-0-(trans-3-0-(β -d-glucopyranosyl)caffeyl)-β-d-glucopyranosyl)- caffeic acid, a novel component in heavenly blue anthocyanin , 1981 .

[21]  L. Jurd,et al.  Anthocyanidins and related compounds—VII : Reactions of flavylium salts with 5,5-dimethyl-1,3-cyclohexanedione at pH 5·8 , 1965 .

[22]  D. Skingle,et al.  Corrigenda - Flavan derivatives. XVIII. Synthesis of hemiketals containing the peltogynol ring system : 3 (3') - hydroxyisochromano (4',3':2, 3) chromans. Conversion of 2'-hydroxychdcones into flav-3-enes and its biosyntheticimplications , 1967 .

[23]  W. Cummings,et al.  872. Polymerisation of flavans. Part II. The condensation of 4′-methoxyflavan with phenols , 1958 .

[24]  R. H. Schuler,et al.  The electron spin resonance spectra of radical intermediates in the oxidation of ascorbic acid and related substances. , 1972, Journal of the American Chemical Society.

[25]  B. Mcloughlin A novel reduction of carbonyl to methylene by the action of sodium borohydride , 1969 .

[26]  P. Karrer,et al.  Die Konstitution des „574‐Chromogens”︁ oder Hepaxanthins aus Lebertran , 1945 .

[27]  L. Jurd Anthocyanins and Related Compounds. I. Structural Transformations of Flavylium Salts in Acidic Solutions , 1963 .

[28]  H. Fuwa,et al.  Major Anthocyanin of Bolivian Purple Corn (Zea mays L.) , 1979 .

[29]  S. Tanchev,et al.  Kinetics of thermal degradation of some anthocyanidin-3,5-diglucosides , 1974 .

[30]  L. Jurd,et al.  Anthocyanidins and related compounds—XIV : Reductive dimerization of flavylium salts by metals , 1968 .

[31]  R. Robinson,et al.  CX.—The synthesis and constitution of certain pyranol salts related to brazilein and haematein , 1908 .

[32]  T. Hoshino,et al.  Self-association of some anthocyanins in neutral aqueous solution , 1981 .

[33]  G. Hrazdina Sodium borohydride reduction of anthocyanidins , 1972 .

[34]  W. Ollis,et al.  The neoflavanoid group of natural products—II.: The examination of Machaerium scleroxylon and some biogenetic proposal regarding the neoflavanoids , 1965 .

[35]  L. Jurd Formation of flavans in reactions of 4‐hydroxycoumarin with flavylium salts , 1981 .

[36]  R. Robinson,et al.  XXVI.—A synthesis of pyrylium salts of anthocyanidin type. Part V. The synthesis of cyanidin chloride and of delphinidin chloride , 1925 .

[37]  K. Bell Reductive removal by sodium borohydride of side-chain oxygen from phenolic ketones , 1969 .

[38]  G. Hrazdina 1. RECENT TECHNIQUES IN THE ANALYSIS OF ANTHOCYANINS IN FRUITS AND BEVERAGES , 1979 .

[39]  D. Strack,et al.  Polyamide column chromatography for resolution of complex mixtures of anthocyanins , 1975 .

[40]  G. Janzsó,et al.  The reactions of flavonoids with p-tosylhydrazine , 1966 .

[41]  G. Hrazdina,et al.  ANTHOCYANINS AS FOOD COLORANTS: EFFECT OF pH ON THE FORMATION OF ANTHOCYANIN‐RUTIN COMPLEXES , 1979 .

[42]  T. Somers Wine Tannins—Isolation of Condensed Flavonoid Pigments by Gel-Filtration , 1966, Nature.

[43]  L. Jurd,et al.  The formation of metal and “co-pigment” complexes of cyanidin 3-glucoside , 1966 .

[44]  C. F. Timberlake,et al.  Flavylium salts, anthocyanidins and anthocyanins. II. Reactions with sulphur dioxide. , 1967, Journal of the science of food and agriculture.

[45]  P. Karrer,et al.  Pflanzenfarbstoffe XL. Zur Kenntnis des oxydativen Abbaus der Anthocyane. Konstitution des Malvons , 1932 .

[46]  N. Harada,et al.  Evidence for the self-association of anthocyanins IV. PMR spectroscopic evidence for the vertical stacking of anthocyanin molecules , 1982 .

[47]  R. Robinson,et al.  Conversion of Flavonols into Anthocyanidins , 1950, Nature.

[48]  A. W. Johnson,et al.  69. A new synthesis of benzopyrylium salts , 1947 .

[49]  C. F. Timberlake,et al.  Anthocyanins: colour augmentation with catechin and acetaldehyde. , 1977, Journal of the science of food and agriculture.

[50]  L. Jurd Quinones and quinone-methides—I : Cyclization and dimerisation of crystalline ortho-quinone methides from phenol oxidation reactions , 1977 .

[51]  L. Jurd,et al.  Anthocyanins and related compounds—VI , 1965 .

[52]  G. Hrazdina Column chromatographic isolation of the anthocyanidin-3,5-diglucosides from grapes , 1970 .

[53]  K. Norris,et al.  Anthocyanin, flavonol copigments, and pH responsible for larkspur flower color , 1975 .

[54]  A. Löwenbein,et al.  Über 2,3,4‐trisubstituierte Chromenylradikale , 2022 .

[55]  N. Nybom Thin-Layer Chromatographic Analysis of Anthocyanidins , 1964 .

[56]  L. Jurd Cinnamyl alcohol : Polyphenol condensations in aqueous solutions , 1969 .

[57]  J. H. Elbe,et al.  High Performance Liquid Chromatography of Plant Pigments – A Review , 1982 .

[58]  K. Freudenberg,et al.  Die Umwandlung des Cyanidins in Catechin. 20. Mitteilung über Gerbstoffe und ähnliche Verbindungen , 1925 .

[59]  R. Robinson,et al.  CCCLXXIV.—Experiments on the synthesis of the anthocyanins. Part VIII. A synthesis of œnin chloride , 1931 .

[60]  T. Somers Resolution and analysis of total phenolic constituents of grape pigment , 1967 .

[61]  G. Mcgall,et al.  Hydration of the flavylium ion. 2. The 4'-hydroxyflavylium ion , 1982 .

[62]  K. Freudenberg,et al.  Umwandlungen der Anthocyanidine und Catechine. (28. Mitteilung über Gerbstoffe und ähnliche Verbindungen) , 1935 .

[63]  J. Harborne The chromatographic identification of anthocyanin pigments , 1958 .

[64]  R. Wrolstad,et al.  Color Degradation in an Ascorbic Acid‐Anthocyanin‐Flavanol Model System , 1981 .

[65]  T. H. Regan,et al.  Formation of dimers from flavylium salts , 1967 .

[66]  R. Robinson,et al.  CVII.—A synthesis of pyrylium salts of anthocyanidin type. Part XIX. A synthesis of delphinidin chloride not involving a demethylation process, and syntheses of hirsutidin chloride and of delphinidin chloride 3′-methyl ether, possibly identical with petunidin chloride , 1930 .

[67]  R. Brouillard Origin of the exceptional colour stability of the Zebrina anthocyanin , 1981 .

[68]  C. Walling Fenton's reagent revisited , 1975 .

[69]  R. Robinson,et al.  XXV.—A synthesis of pyrylium salts of anthocyanidin type. Part III. A new synthesis of pelargonidin chloride , 2022 .

[70]  L. Jurd Anthocyanins and Related Compounds. III. Oxidation of Substituted Flavylium Salts to 2-Phenylbenzofurans , 1964 .

[71]  L. Merlini,et al.  Constituents of dragon's blood. Part II. Structure and oxidative conversion of a novel secobiflavonoid , 1976 .

[72]  M. Gadret,et al.  Structure du chlorure d'apigéninidine monohydraté , 1974 .

[73]  J. Harborne,et al.  Plant polyphenols—XVI. , 1967 .

[74]  T. Hoshino,et al.  Evidences of the self-association of anthocyanins I. Circular Dichroism of cyanin anhydrobase , 1980 .

[75]  Geza Hrazdina,et al.  Structural aspects of anthocyanin-flavonoid complex formation and its role in plant color , 1981 .

[76]  J. Vanallan,et al.  Reduction of some flavylium salts with sodium borohydride , 1967 .

[77]  L. Merlini,et al.  Constituents of Dragon's blood. Part I. Structure and absolute configuration of new optically active flavans , 1971 .

[78]  T. Hoshino,et al.  A proposed structure of commelinin, a sky-blue anthocyanin complex obtained from the flower petals of , 1979 .

[79]  K. Yoshitama An acylated delphinidin 3-rutinoside-5,3′,5′-triglucoside from Lobelia erinus , 1977 .

[80]  H. Decker,et al.  Synthese von Derivaten des Phenopyryliums , 1907 .

[81]  K. Norris,et al.  Co-pigmentation of anthocyanins in plant tissues and its effect on color , 1972 .

[82]  A. Löwenbein Über 2.4-Diaryl-chromene. (In Gemeinschaft mit E. Pongrácz und E. A. Spiess) , 1924 .

[83]  P. Markakis,et al.  Anthocyanins and their stability in foods , 1974 .

[84]  L. Jurd,et al.  Anthocyanins and related compounds—VI : Flavylium salt—phloroglucinol condensation products , 1965 .

[85]  L. Jurd,et al.  Anthocyanins and Related Compounds. II. Structural Transformations of Some Anhydro Bases , 1963 .

[86]  H. Hundt,et al.  Synthesis of condensed tannins. Part 3. Chemical shifts for determining the 6- and 8-bonding positions of ‘terminal of’(+)-catechin units , 1981 .

[87]  L. Jurd Biogenetic-type syntheses of obtusastyrene and 4-methoxydalbergione. , 1969, Tetrahedron letters.

[88]  The identification of poinsettia cultivars by HPLC analysis of their anthocyanin content , 1979 .

[89]  L. Jurd,et al.  Quinones and quinone methides—II: cyclization and hydration reactions of 2-cinnamyl-5-methoxy-1,4-benzoquinones , 1978 .

[90]  Z. Kertesz,et al.  PARTICIPATION OF ASCORBIC ACID IN THE DESTRUCTION OF ANTHOCYANIN IN STRAWBERRY JUICE AND MODEL SYSTEMSa , 1953 .

[91]  T. Somers The polymeric nature of wine pigments , 1971 .

[92]  R. Robinson,et al.  CLVI.—A synthesis of pyrylium salts of anthocyanidin type. Part VI. Polyhydroxyflavylium salts related to chrysin, apigenin, lotoflavin, luteolin, galangin, fisetin, and morin , 2022 .

[93]  J. G. Sweeny,et al.  Synthesis of anthocyanidins—II : The synthesis of 3-deoxyanthocyanidins from 5-hydroxy-flavanones , 1977 .

[94]  T. Emilewicz,et al.  Synthese des 3-Oxyflavons , 1898 .

[95]  K. Freudenberg,et al.  Der Quebracho‐gerbstoff. 27. Mitteilung über Gerbstoffe und ähnliche Verbindungen , 1934 .

[96]  A. Zanarotti Synthesis of a flav-3-en-3-ol via cinnamylphenol , 1983 .

[97]  Kenzo Abe,et al.  Chromatographic and spectral characterization of 3′-glycosylation in anthocyanidins , 1977 .

[98]  F. Kröhnke,et al.  Reaktionen cyclischer Oxonium‐Ionen mit nucleophilen Partnern , 1959 .

[99]  R. Robinson,et al.  XXVI.—A synthesis of pyrylium salts of anthocyanidin type. Part IV. Flavylium salts related to chrysin, apigenin, and luteolin , 2022 .

[100]  T. Goto,et al.  PMR spectra of natural acylated anthocyanins determination of stereostructure of awobanin, shisonin and violanin , 1978 .

[101]  D. Mullick Thin layer chromatography of anthocyanidins. I. Techniques and solvents for two-dimensional chromatography. , 1969, Journal of chromatography.

[102]  R. Robinson,et al.  CLXIV.—A synthesis of pyrylium salts of anthocyanidin type. Part VIII. A new synthesis of pelargonidin chloride and of galanginidin chloride , 1925 .

[103]  J. Harborne Plant polyphenols IX. The glycosidic pattern of anthocyanin pigments , 1963 .

[104]  L. Jurd Anthocyanidins and related compounds—XI: Catechin-flavylium salt condensation reactions , 1967 .

[105]  J. G. Sweeny,et al.  Synthesis of anthocyanidins-III: Total synthesis of apigeninidin and luteolinidin chlorides , 1977 .

[106]  T. White,et al.  775. The conversion of flavonols into anthocyanidins , 1957 .

[107]  F. J. Francis Chapter 7 – Analysis of Anthocyanins , 1982 .

[108]  R. Cricchio,et al.  Biogenetic-like synthesis of flav-3-enes from o-cinnamylphenols. , 1969, Tetrahedron letters.

[109]  R. Robinson Über die Synthese von Anthocyaninen , 1934 .

[110]  J. Clark‐Lewis,et al.  Flavan derivatives. XXXII. Structures and N.M.R. spectra of Flav-2-enes and Flav-3-enes; Hydroboration and hydroxylation of Flav-3-enes , 1971 .

[111]  R. Wizinger,et al.  Beitrag zur Kenntnis der 2‐Aryl‐benzopyryliumsalze , 1951 .

[112]  W. Forbes,et al.  The chemistry of extractives from hardwoods. Part XXV.(—)-epiAfzelechin, a new member of the catechin series , 1955 .

[113]  K. Freudenberg,et al.  Zur Kenntnis der Catechine und Catechingerbstoffe , 1954 .

[114]  R. Brouillard,et al.  Chemistry of anthocyanin pigments. 2. Kinetic and thermodynamic study of proton transfer, hydration, and tautomeric reactions of malvidin 3-glucoside , 1977 .

[115]  G. Hrazdina,et al.  Oxidation products of acylated anthocyanins under acidic and neutral conditions , 1974 .

[116]  R. McClelland,et al.  Hydration of the flavylium ion , 1980 .

[117]  R. Molyneux,et al.  The reductive acetylation of quercetin , 1967 .

[118]  N. Harada,et al.  Chiral exciton coupled stacking of anthocyanins: interpretation of the origin of anomalous CD induced by anthocyanin association , 1981 .

[119]  P. Karrer,et al.  Über die Reduktion der Pyryliumsalze mit Lithiumaluminiumhydrid , 1950 .

[120]  L. Jurd Anthocyanidins and related compounds—XIII : Hydrogen peroxide oxidation of flavylium salts , 1968 .

[121]  F. J. Francis,et al.  EFFECT OF FLAVONOLS ON ASCORBIC ACID AND ANTHOCYANIN STABILITY IN MODEL SYSTEMS , 1974 .

[122]  H. Tamura,et al.  Structure of gentiodelphin, an acylated anthocyanin isolated from Gentiana Makinoi, that is stable in dilute aqueous solution , 1982 .

[123]  T. Goto,et al.  Structure confirmation of tris-deacyl heavenly blue anthocyanin, an alkaline hydrolysis product of heavenly blue anthocyanin obtained from flower of morning glory "heavenly blue" , 1981 .

[124]  V. L. Singleton,et al.  Naturally occurring food toxicants: phenolic substances of plant origin common in foods. , 1981, Advances in food research.

[125]  T. Hoshino,et al.  The stabilizing effect of the acyl group on the co-pigmentation of acylated anthocyanins with C-glucosylflavones , 1980 .

[126]  R. Fèvre 105. The acid condensation of salicylaldehyde with acetylacetone, ethyl acetoacetate, and pyruvic acid , 1934 .

[127]  K. Norris,et al.  Anthocyanin and pH in the color of ‘Heavenly Blue’ morning glory , 1977 .

[128]  H. Decker,et al.  Ueber Phenopyrylium und höhere homologe und isologe Pyryliumringe , 1907 .

[129]  M. Bourzeix,et al.  Estimation qualitative et quantitative de la matière colorante des jus et vins de fruits , 1980 .

[130]  R. Brouillard,et al.  Chemistry of anthocyanin pigments. 6. Kinetic and thermodynamic study of hydrogen sulfite addition to cyanin. Formation of a highly stable Meisenheimer-type adduct derived from a 2-phenylbenzopyrylium salt , 1980 .

[131]  P. Cansfield,et al.  Chromatography of Anthocyanins on Columns of Insoluble Polyvinylpyrrolidone , 1971 .

[132]  L. Jurd The synthesis of coumestrol from a flavylium salt , 1963 .

[133]  Antonio Zanarotti,et al.  Preparation and reactivity of 2,6—dimethoxy—4—allylidene—2,5—cyclohexadien—1—one (vinyl quinone methide) a novel synthesis of sinapyl alcohol , 1982 .