Occurrence and content of hydroxycinnamic and hydroxybenzoic acid compounds in foods.

Phenolic acid compounds seem to be universally distributed in plants. They have been the subject of a great number of chemical, biological, agricultural, and medical studies. Hydroxycinnamic acid compounds occur most frequently as simple esters with hydroxy carboxylic acids or glucose, while the hydroxybenzoic acid compounds are present mainly in the form of glucosides. Furthermore, phenolic acids may occur in food plants as esters or glycosides conjugated with other natural compounds such as flavonoids, alcohols, hydroxyfatty acids, sterols, and glucosides. Also, hydroxycinnamic acid amides appear to be common constituents. The occurrence of the different natural phenolic acid compounds in foods is reviewed, and data of the content in fruit, vegetables, and spices are given. The distribution of the main phenolic acid compounds in food plants as well as their changes during development and maturation of fruits are considered. Furthermore, the hydroxycinnamic acids bound to cell wall polymers, the phenolic acid compounds in coffee, cereals, oil seed, and tree nuts, and the analysis of phenolic acid derivatives are reviewed.

[1]  K. Herrmann.  Über den „Gerbstoff”︁ der Labiatenblätter , 1960 .

[2]  C. Nagel,et al.  Hydroxycinnamic Acid-Tartaric Acid Ester Content in Mature Grapes and During the Maturation of White Riesling Grapes , 1978, American Journal of Enology and Viticulture.

[3]  H. Pooter,et al.  N-feruloylglycyl-l-phenylalanine: A sequence in barley proteins , 1973 .

[4]  K. Herrmann,et al.  Esters and glucosides of hydroxycinnamic acids in vegetables , 1986 .

[5]  B. Schuster,et al.  Hydroxybenzoic and hydroxycinnamic acid derivatives in soft fruits , 1985 .

[6]  V. Lattanzio,et al.  Changes in phenolic compounds during the development and cold storage of artichoke (Cynara scolymus L.) heads , 1987 .

[7]  E. Haslam,et al.  399. Synthesis and properties of some hydroxycinnamoyl esters of quinic acid , 1964 .

[8]  R. Cartwright,et al.  Theogallin, a polyphenol occurring in tea , 1954 .

[9]  V. L. Singleton,et al.  Caftaric and coutaric acids in fruit of Vitis , 1986 .

[10]  P. Kolattukudy,et al.  Evidence for Covalently Attached p-Coumaric Acid and Ferulic Acid in Cutins and Suberins. , 1975, Plant physiology.

[11]  H. Chiji,et al.  Two Phenolic Amides in the Seed Balls of Sugar Beet (Beta vulgaris L. var. saccharifera Alefeld) , 1984 .

[12]  A. Kato,et al.  Isolation of methyl ferulate from rice bran oil , 1971 .

[13]  F. Sosulski,et al.  Composition of free and hydrolyzable phenolic acids in defatted flours of ten oilseeds , 1984 .

[14]  Takeshi Matsumoto,et al.  Serotobenine, a Novel Phenolic Amide from Safflower Seeds (Carthamus tinctorius L.) , 1985 .

[15]  F. Sosulski,et al.  Composition of free and hydrolyzable phenolic acids in the flours and hulls of ten legume species , 1984 .

[16]  J. Macheix,et al.  Tissue compartmentation of phenylpropanoid metabolism in tomatoes during growth and maturation , 1985 .

[17]  P. Scheuer,et al.  Isolation of glyceryl esters of caffeic and p-coumaric acids from pineapple stems , 1976 .

[18]  K. Herrmann,et al.  Analysis of methyl and ethyl esters of hydroxybenzoic and hydroxycinnamic acids in plant material , 1982 .

[19]  M. Yalpani,et al.  The phenolic acids of Pistachia vera , 1983 .

[20]  Susumu Watanabe,et al.  The Structures of Acylated Anthocyanins in Eggplant and Perilla and the Position of Acylation , 1966 .

[21]  K. Herrmann,et al.  Analytical and preparative high-performance liquid chromatography of hydroxycinnamic acid esters , 1983 .

[22]  A. Ehmann.  N-(p-coumaryl)-tryptamine and N-ferulyltryptamine in kernels of Zea mays. , 1974 .

[23]  F. Sosulski,et al.  Phenolic acids in oilseed flours. , 1983, Die Nahrung.

[24]  K. Herrmann,et al.  ᴅ-( + )-Dikaffeoyl-Weinsäure aus Endivien ( Cichorium endivia L.) / ᴅ-( + ) -Dicaffeoyl Tartaric Acid from Endives (Cichorium endivia L .) , 1974 .

[25]  T. Adzet,et al.  High-performance liquid chromatography of caffeoylquinic acid derivatives of Cynara scolymus L. leaves , 1985 .

[26]  Gary W. Sanderson,et al.  The Chemistry of Tea and Tea Manufacturing , 1972 .

[27]  M. Winter,et al.  Bestimmung von Hydroxyzimtsaure-Derivaten in Gemüse , 1987 .

[28]  K. Herrmann.  Die phenolischen Inhaltsstoffe des Obstes , 1973 .

[29]  C. Nagel,et al.  High-pressure liquid chromatographyic analysis of hydroxycinnamic acid—tartaric acid esters and their glucose esters in vitis vinifera☆ , 1978 .

[30]  C. Nagel,et al.  Changes in the Anthocyanins, Flavonoids and Hydroxycinnamic Acid Esters during Fermentation and Aging of Merlot and Cabernet Sauvignon , 1979, American Journal of Enology and Viticulture.

[31]  G. Robertson,et al.  Salicylic acid in fresh and canned fruit and vegetables , 1981 .

[32]  William F. Haddon,et al.  Caffeyl esters of glucaric acid in Lycopersicon esculentum leaves , 1981 .

[33]  S. Klick,et al.  Glucosides and glucose esters of hydroxybenzoic acids in plants , 1988 .

[34]  B. Stengel,et al.  Notizen: Kämpferol-3-(O-sinapoylsophorosid)-7-glucosid, ein neues Flavonoid aus Brassica napus L. (Cruciferae)/Kaempferole-3-(O-sinapoylsophoroside)-7-glucoside, a New Flavonoid from Brassica napus L. (Cruciferae) , 1976 .

[35]  F. Sosulski,et al.  Chlorogenic acid-protein interactions in sunflower. , 1974, Journal of agricultural and food chemistry.

[36]  K. Herrmann,et al.  Analysis of hydroxybenzoic and hydroxycinnamic acids in plant material : II. Determination by gas-liquid chromatography , 1980 .

[37]  M. Linscheid,et al.  The Structures of Sinapic Acid Esters and Their Metabolism in Cotyledons of Raphanus sativus , 1980 .

[38]  K. Herrmann,et al.  4-(β-D-glucopyranosyloxy)benzoic acid, a characteristic phenolic constituent of the Apiaceae , 1984 .

[39]  K. Herrmann,et al.  [On the occurrence of proanthocyanidins, leucoanthocyanidins and catechins in vegetables (author's transl)]. , 1976, Zeitschrift fur Lebensmittel-Untersuchung und -Forschung.

[40]  C. Nagel,et al.  Separation and Purification of Hydroxycinnamic Acid Derivatives in Cranberries , 1982 .

[41]  L. Nagels,et al.  High-performance liquid chromatographic separation of naturally occurring esters of phenolic acids , 1980 .

[42]  D. Nevins,et al.  Isolation and identification of O-(5-O-feruloyl-α-l-arabinofuranosyl)-1(→3)-O-β-d-xylopyranosyl-(1→4)-d-xylopyranose as a component of Zea shoot cell-walls☆ , 1985 .

[43]  B. Möller,et al.  Analysis of quinic acid esters of hydroxycinnamic acids in plant material by capillary gas chromatography and high-performance liquid chromatography , 1982 .

[44]  K. Herrmann,et al.  Changes in catechins and hydroxycinnamic acid derivatives during development of apples and pears. , 1974, Journal of the science of food and agriculture.

[45]  G. Oriente,et al.  Chicoric acid (dicaffeyltartic acid): Its isolation from chicory (Chicorium intybus) and synthesis , 1958 .

[46]  B. Möller,et al.  Quinic acid esters of hydroxycinnamic acids in stone and pome fruit , 1983 .

[47]  M. Nishijima,et al.  Benzoic acid in fruits and fruit products , 1983 .

[48]  K. Herrmann,et al.  Isolierung und Identifizierung der Flavon(ol)-O-glykoside in Kümmel (Carum carvi L.), Fenchel (Foeniculum vulgare Mill.), Anis (Pimpinella anisum L.) und Koriander (Coriandrum sativum L.) und von Flavon-C-glykosiden im Anis , 1977 .

[49]  M. Amiot,et al.  Importance and evolution of phenolic compounds in olive during growth and maturation , 1986 .

[50]  K. Hasegawa,et al.  Raphanusol A, a new growth inhibitor from sakurajima radish seedlings , 1982 .

[51]  V. L. Singleton,et al.  Compositional changes in ripening grapes: Caftaric and coutaric acids , 1986 .

[52]  S. Fry,et al.  Barley endosperm cell walls contain a feruloylated arabinoxylan and a non-feruloylated β-glucan , 1986 .

[53]  M. Matsumoto,et al.  Sinapic acid and methyl sinapate in rapeseed lipids. , 1971, Biochimica et biophysica acta.

[54]  D. L. Wetzel,et al.  High-performance liquid chromatographic determination of ferulic acid in wheat milling fractions as a measure of bran contamination. , 1987, Journal of chromatography.

[55]  M. Clifford,et al.  The chlorogenic acids content of coffee substitutes , 1987 .

[56]  E. Baker,et al.  Phenolic constituents of tomato fruit cuticles , 1980 .

[57]  C. Nagel,et al.  Identification of the Hydroxycinnamtic Acid Derivatives in Cranberries , 1982 .

[58]  K. Herrmann.  Hydroxyzimtsäuren und Hydroxybenzoesäuren enthaltende Naturstoffe in Pflanzen , 1978 .

[59]  A. D. Webb,et al.  Structures of Acylated Anthocyan Pigments in Vitis vinifera variety Tinta Pinheira. II. Position of Acylation , 1965 .

[60]  T. Goto,et al.  Structure of Three Diacylated Anthocyanins Isolated from Red Cabbage, Brassica oleracea , 1987 .

[61]  A. Vaccari,et al.  Anthocyanins of Sunflower (Helianthus annuus) , 1982 .

[62]  L. Trugo,et al.  A study of the effect of roasting on the chlorogenic acid composition of coffee using HPLC , 1984 .

[63]  C. Nagel,et al.  High-Pressure Liquid Chromatographic Separation of Anthocyanins of Vitis Vinifera , 1978, American Journal of Enology and Viticulture.

[64]  F. Sosulski,et al.  Phenolic acids in rapeseed and mustard , 1983 .

[65]  R. Hartley,et al.  Phenolic constituents of the cell walls of monocotyledons , 1980 .

[66]  K. Herrmann,et al.  Die Gehalte an Hydroxyzimtsaure-Verbindungen und Catechinen in Kern- und Steinobst , 1988 .

[67]  J. Powers,et al.  The Hydroxycinnamic Acid Tartaric Acid Ester Content of Musts and Grape Varieties Grown in the Pacific Northwest , 1979, American Journal of Enology and Viticulture.

[68]  H. Neukom,et al.  Ferulic Acid as a Component of a Glycoprotein from Wheat Flour , 1963, Nature.

[69]  H. Klosterman,et al.  The Glucosides of Flaxseed. II. Linocaffein1 , 1959 .

[70]  O. Olsen,et al.  2-O-(p-coumaroyl)-L-malate, 2-O-caffeoyl-L-malate and 2-O-feruloyl-L-malate in Raphanus sativus , 1984 .

[71]  D. Metzler,et al.  3-O-Caffeoylshikimic acid (dactylifric acid) and its isomers, a new class of enzymic browning substrates. , 1964, Biochemical and biophysical research communications.

[72]  W. R. Forbus,et al.  Comparative GLC‐MS Analysis of Phenolic Acids of Selected Tree Nuts , 1983 .

[73]  J. Harborne.  Plant polyphenols—XI. , 1964 .

[74]  D. G. Daniels,et al.  Antioxidants in oats : Glyceryl esters of caffeic and ferulic acids , 1968 .

[75]  A. B. Durkee,et al.  FERULIC ACID AND OTHER PHENOLICS IN OAT SEEDS (Avena sativa L. Var Hinoat) , 1977 .

[76]  Y. Fujimoto,et al.  3-Caffeoyl-4-sinapoylquinic acid, a novel lipoxygenase inhibitor from Gardeniae fructus. , 1987, Chemical & pharmaceutical bulletin.

[77]  K. Herrmann,et al.  The phenolics of fruits , 1975, Zeitschrift fur Lebensmittel-Untersuchung und -Forschung.

[78]  O. Olsen,et al.  4-Hydroxybenzoylcholine: A natural product present in Sinapis alba , 1982 .

[79]  F. Hayase,et al.  Antioxidative components of sweet potatoes. , 1984, Journal of nutritional science and vitaminology.

[80]  V. Cheynier,et al.  Characterization of 2-S-glutathionyl caftaric acid and its hydrolysis in relation to grape wines , 1986 .

[81]  Identification o f the Major Anthocyanin o f Carrot Cells in Tissue Culture as Cyanidin 3-(Sinapoylxylosylglucosylgalactoside) , 1983 .

[82]  Ulrich Engelhardt,et al.  Chlorogensänren in Kaffee-Ersatzstoffen , 1986 .

[83]  L. Trugo,et al.  Chlorogenic acid composition of instant coffees. , 1984, The Analyst.

[84]  J. Sapis,et al.  Browning capacity of grapes. 3. Changes and importance of hydroxycinnamic acid-tartaric acid esters during development and maturation of the fruit , 1983 .

[85]  R. Kido,et al.  Caffeoyltryptophan from green robusta coffee beans , 1987 .

[86]  W. Heimann,et al.  ber das Vorkommen der Hydroxyzimtsuren im Gemse@@@About the occurrence of hydroxycinnamic acids in vegetables: III. Mitteilung ber die im Kopfsalat hauptschlich vorkommende Kaffeesure-Verbindung@@@III. About the Main Caffeic Acid Component of Lettuce , 1971 .

[87]  V. Wray,et al.  (E)-O-p-Coumaroyl-, (E)-O-Feruloyl-derivatives of glucaric acid in citrus , 1988 .

[88]  L. Hogge,et al.  Free, esterified, and insoluble-bound phenolic acids. 3. Composition of phenolic acids in cereal and potato flours , 1982 .

[89]  E. Haslam,et al.  The caffeine—potassium chlorogenate molecular complex , 1986 .

[90]  R. Hartley,et al.  Occurrence and nature of ferulic acid substitution of cell-wall polysaccharides in graminaceous plants , 1983 .

[91]  C. Nagel,et al.  Characterization of Cranberry Benzoates and Their Antimicrobial Properties , 1986 .

[92]  J. Harborne,et al.  Distribution of charged flavones and caffeylshikimic acid in Palmae , 1974 .

[93]  N. L. Lahiry,et al.  CHARACTERIZATION OF THE CHLOROGENIC ACID BINDING FRACTION IN LEAF PROTEIN CONCENTRATION , 1977 .

[94]  D. Thompson.  Chlorogenic Acid and Other Phenolic Compounds in Fourteen Sweet Potato Cultivars , 1981 .

[95]  W. Oettmeier,et al.  Notizen: p-coumaroyl-meso-tartaric acid from Spinach Chloroplast Preparations , 1972, Zeitschrift fur Naturforschung. Teil B. Anorganische Chemie, organische Chemie, Biochemie, Biophysik, Biologie.

[96]  D. G. Daniels,et al.  Antioxidants in oats: Mono-esters of caffeic and ferulic acids , 1967 .

[97]  K. Herrmann,et al.  ber die Phenolsuren des Gemses: III. Hydroxyzimtsuren und Hydroxybenzoesuren des Wurzelgemses , 1975 .

[98]  Portland Press Ltd.  IUPAC Commission on the Nomenclature of Organic Chemistry (CNOC) and IUPAC-IUB Commission on Biochemical Nomenclature (CBN). Nomenclature of cyclitols. Recommendations, 1973. , 1976, The Biochemical journal.

[99]  B. Schuster,et al.  4-O-β-ᴅ-Glucosides of Hydroxybenzoic and Hydroxycinnamic Acids — Their Synthesis and Determination in Berry Fruit and Vegetable , 1986 .

[100]  N. Lewis,et al.  5-hydroxyferulic acid in Zea mays and Hordeum vulgare cell walls , 1987 .

[101]  D. Strack,et al.  Accumulation and enzymatic synthesis of 2-O-acetyl-3-O-(p-coumaroyl)-meso-tartaric acid in spinach cotyledons , 1986 .

[102]  H. Neukom,et al.  Diferulic acid as a possible crosslink in hemicelluloses from wheat germ. , 1976 .

[103]  D. Frost,et al.  The theaflavins of black tea , 1973 .

[104]  K. Tadera,et al.  Isolation and Chemical Structure of a New Fluorescent Compound in Spinach Leaves , 1971 .

[105]  A. Bacic,et al.  Release of Ferulic Acid Esters From Barley Aleurone. II. Characterization of the Feruloyl Compounds Released in Response to GA3 , 1985 .

[106]  C. Nagel,et al.  The Caffeoyl Tartrate Content of White Riesling Wines from California, Washington, and Alsace , 1985, American Journal of Enology and Viticulture.

[107]  E. Roberts,et al.  Theogallin, a polyphenol occurring in tea. II.—Identification as a galloylquinic acid , 1958 .

[108]  R. Kido,et al.  3-O-caffeoyl-4-O-feruloylquinic acid from green robusta coffee beans , 1986 .

[109]  K. Herrmann,et al.  Analysis of hydroxycinnamic acid esters and their glucosides by reversed-phase high-performance liquid chromatography after polyamide separation , 1984 .

[110]  J. Azuma,et al.  Isolation and Identification of a New Feruloylated Tetrasaccharide from Bagasse Lignin-Carbohydrate Complex Containing Phenolic Acid , 1987 .

[111]  W. Henning.  Schnelle Sinapin-Bestimmung mit Ionen-Paar HPLC aus Speisesenf und Senfsaaten , 1982 .

[112]  Swain Ar,et al.  Salicylates in foods. , 1985 .

[113]  V. Wray,et al.  Ferulic acid esters of sugar carboxylic acids from primary leaves of rye (secale cereale) , 1986 .

[114]  C. V. Sumere,et al.  Separation of phenolics (benzoic acids, cinnamic acids, phenylacetic acids, quinic acid esters, benzaldehydes and acetophenones, miscellaneous phenolics) and coumarins by reversed-phase high-performance liquid chromatography , 1983 .

[115]  V. Wray,et al.  2′-(E)-O-p-coumaroylgalactaric acid and 2′-(E)-O-feruloylgalactaric acid in citrus , 1987 .

[116]  Yuzuru Suzuki,et al.  Studies on a New p -Coumaryl Derivative Isolated from Spinach Leaves:Part II. Determination of Chemical Structuret , 1970 .

[117]  A. D. Webb,et al.  Structures of Acylated Anthocyan Pigments in Vitis vinifera Variety Tinta Pinheira. Identification of Anthocyanidin, Sugar, and Acid Moieties , 1965 .

[118]  K. Herrmann,et al.  The phenolics of fruits , 1974 .

[119]  M. Shimizu,et al.  A new triterpenoid alcohol, 24-methylenecycloartanol, as its ferulate, from rice bran oil. , 1958, Chemical and pharmaceutical bulletin.

[120]  A. Salomonsson,et al.  Distribution of insoluble bound phenolic acids in barley grain , 1984 .

[121]  W. Koch,et al.  Acylierte Anthocyane III. , 1965 .

[122]  H. Blundstone.  Hydroxycinnamic acid derivatives of rheum rhaponticum , 1970 .

[123]  V. Wray,et al.  Coumaroyl-, caffeoyl- and feruloyltartronates and their accumulation in mung bean , 1985 .

[124]  K. Herrmann,et al.  Die phenolischen Inhaltsstoffe des Obstes IV. Die phenolischen Inhaltsstoffe der Brombeeren und Himbeeren und deren Veränderungen wahrend Wachstum und Reife der Früchte , 1974 .

[125]  N. Shibuya.  Phenolic acids and their carbohydrate esters in rice endosperm cell walls , 1984 .

[126]  V. Wray,et al.  12-disinapolylglucose accumulated in cotyledons of dark-grown raphanus sativus seedlings , 1984 .

[127]  M. Clifford.  Coffee bean dicaffeoylquinic acids , 1986 .

[128]  K. Herrmann,et al.  [V. The phenolics of strawberries and their changes during development and ripeness of the fruits (author's transl)]. , 1975, Zeitschrift fur Lebensmittel-Untersuchung und -Forschung.

[129]  E. Sondheimer.  On the distribution of caffeic acid and the chlorogenic acid isomers in plants. , 1958, Archives of biochemistry and biophysics.

[130]  E. Guittet,et al.  Ether linkage between phenolic acids and lignin fractions from wheat straw , 1985 .

[131]  W. Pilnik,et al.  Measurement of chlorogenic acid and flavonol glycosides in apple juice by a chromatographic-fluorometric method , 1973 .

[132]  K. Herrmann,et al.  Analysis of hydroxybenzoic and hydroxycinnamic acids in plant material. I. Sample preparation and thin-layer chromatography. II. Determination by gas-liquid chromatography. , 1980 .

[133]  Claude Martin,et al.  The distribution of hydroxycinnamic acid amides in flowering plants , 1978 .

[134]  A. Wheeler,et al.  Conversion of tryptophan to auxin by phenolic esters from leaves of dwarf french bean (Phaseolus vulgaris L.) , 1968 .

[135]  J. Adamovics,et al.  Ferulates from cork layers of Solanum tuberosum and Pseudotsuga menziesii , 1977 .

[136]  K. Herrmann,et al.  Hydroxyzimtsäureester der Kohlarten und der Gartenkresse , 1983 .

[137]  S. Klick,et al.  Analysis of naturally occurring hydroxybenzoic acid glucosides and hydroxybenzoyl glucoses and their behaviour on a polyamide column , 1988 .

[138]  K. Herrmann,et al.  Die phenolischen Inhaltsstoffe des Obstes , 1975 .

[139]  S. Fry.  Phenolic components of the primary cell wall. Feruloylated disaccharides of D-galactose and L-arabinose from spinach polysaccharide. , 1982, The Biochemical journal.