Skip to main content

Gallic Acid Derivatives and Hydrolyzable Tannins

  • Chapter
Natural Products of Woody Plants

Part of the book series: Springer Series in Wood Science ((SSWOO))

Abstract

Gallic acid and its derivatives as they occur in extracts of oak-galls constitute a chemical reagent of considerable antiquity. The blue-black color produced when an aqueous infusion is treated with salts of iron was first described by Pliny; its use in the analysis of mineral waters and as a component of invisible ink were noted as early as the sixteenth century. The eminent Swedish chemist Scheele first isolated gallic acid from oak-galls toward the end of the eighteenth century and the acid was named gallic by Braconnot in reference to its origin in plant galls. One of the first published preparations of gallic acid, however, is that of Sir Humphrey Davy (79) in the Journal of the Royal Institute (1803); he followed a directive from the trustees and governors to present a series of lectures on ‘the chemical principles of the art of tanning.’ This incident vividly illustrates the intimate relationship, for both scientific and historical reasons, that studies of the chemistry and biochemistry of gallic acid and its derivatives have with those of the vegetable tannins and ultimately the proanthocyanidins (142).

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Armitage R, Bayliss GS, Gramshaw JG, Haslam E, Haworth RD, Jones K, Searle T 1961 Gallotannins, Part 3. The Constitution of Chinese, Turkish, sumac and tara tannins. J Chem Soc 1842–1853

    Google Scholar 

  2. Bate-Smith E C 1962 The phenolic constituents of plants and their taxonomic significance. J Linn Soc London Bot 95–173

    Google Scholar 

  3. Bate-Smith E C 1973 Haemanalysis of tannins: The concept of relative astringency. Phytochemistry 12: 907–912

    Article  CAS  Google Scholar 

  4. Bate-Smith EC 1976 Chemistry and taxonomy of Ribes. Biochem Syst Ecol 4: 13–18

    Article  CAS  Google Scholar 

  5. Bate-Smith E C 1977 Chemistry and taxonomy of the Cunoniaceae. Biochem Syst Ecol 5: 95–105

    Article  CAS  Google Scholar 

  6. Bate-Smith E C 1977 Astringent tannins of Acer species. Phytochemistry 16: 1421–1426

    Article  CAS  Google Scholar 

  7. Bate-Smith E C 1978 Systematic aspects of the astringent tannins of Acer species. Phytochemistry 17: 1945–1948

    Article  CAS  Google Scholar 

  8. Bate-Smith EC 1981 Astringent tannins of the leaves of Geranium species. Phytochemistry 20: 211–216

    Article  CAS  Google Scholar 

  9. Böhm B A 1979 Flavonoids of Tolmiea menziesii. Phytochemistry 18: 1079–1080

    Article  Google Scholar 

  10. Böhm B A, Collins F W, Wilkins C K 1975 The flavonoid glycoside gallates from Tellima grandiflora. Phytochemistry 14: 1099–1102

    Article  Google Scholar 

  11. Bradfield A E, Penney M 1948 The catechins of green tea. Part 2. J Chem Soc 224–2254

    Google Scholar 

  12. Britton G, Haslam E 1965 Gallotannins. Part 12. Phenolic constituents Arctostaphylos uvaursi. J Chem Soc 7312–7319

    Google Scholar 

  13. Britton G, Haslam E, Crabtree P W, Stangroom J E 1966 Gallotannins. Part 13. The structure of Chinese gallotannin. Evidence for a polygalloyl chain. J Chem Soc (C) 783–790

    Google Scholar 

  14. Bu’Lock J D 1965 The biosynthesis of natural products. McGraw-Hill London, 149

    Google Scholar 

  15. Bu’Lock J D 1980 Mycotoxins as secondary metabolites. In: Steyn P S (ed) The biosynthesis of mycotoxins. Academic Press London New York, 1–16

    Google Scholar 

  16. Conn EE, Swain T 1961 Biosynthesis of gallic acid in higher plants. Chem Ind 592–593

    Google Scholar 

  17. Cornthwaite DC,Haslam E 1965 Gallotannins. Part 9. The biosynthesis of gallic acid in Rhus typhina. J Chem Soc 3008–3011

    Google Scholar 

  18. Coxon D T, Holmes A, Ollis W D, Vora V C, Grant M S, Tee J L 1972 Flavonol digallates in green tea leaf. Tetrahedron 28: 2819–2826

    Article  CAS  Google Scholar 

  19. Culvenor C J 1966 The conformation of esters and the ‘acylation shift’. NMR evidence from pyrrolizidine alkaloids. Tetrahedron Lett 1091–1099

    Google Scholar 

  20. Dewick P M, Haslam E 1969 Phenol biosynthesis in higher plants — gallic acid. Biochem J 113: 537–542

    CAS  PubMed  Google Scholar 

  21. Ferrier R J, Collins P M 1972 Monosaccharide chemistry. Penguin London, 40

    Google Scholar 

  22. Fischer E 1919 Untersuchungen über Depside und Gerbstoffe. Springer Berlin, 541

    Google Scholar 

  23. Fischer E, Bergmann K 1918 Über das tannin und die synthese ähnlicher Stoffe. V. Ber Deutsche Chem Ges 51: 1760–1804

    Article  CAS  Google Scholar 

  24. Gilson E R 1903 Sur deux nouveaux glucotannoides. CR Acad Sci 136: 385

    CAS  Google Scholar 

  25. Gonzalez A G, Francisco G G, Friere R, Hernandez R, Salazar J, Suarez E 1976 Lindleyin, a new phenolic gallyl glucoside from Aconium lindleyi. Phytochemistry 15: 344–346

    Article  Google Scholar 

  26. Gross G G 1982 Synthesis of galloyl coenzyme A thiol ester. Z Naturforsch 37C: 778–783

    Google Scholar 

  27. Gross G G 1982 Synthesis of β-glucogallin from UDP glucose and gallic acid by an enzyme from oak leaves. Fed Eur Biochem Lett 148: 67–70

    Article  CAS  Google Scholar 

  28. Gross G G 1983 Synthesis of mono-, di- and trigalloyl- β -D-glucose by β -glucogallin dependent galloyl transferases from oak leaves. Z Naturforsch 38C: 519–523

    Google Scholar 

  29. Gross G G 1983 Partial purification and properties of UDP-glucose: Vanillate 1-O-glucosyl transferase from oak leaves. Phytochemistry 22: 2179–2182

    Article  CAS  Google Scholar 

  30. Gross S R 1978 Recent advances in the chemistry and biochemistry of lignin. In: Swain T, Harborne J B, van Sumere C (eds) Recent advances in phytochemistry — Plant phenolics, vol 12. Plenum Press New York, 177–220

    Google Scholar 

  31. Hagerman A E, Butler L G 1981 The specificity of proanthocyanidin-protein interactions. J Biol Chem 256: 4494–4497

    CAS  PubMed  Google Scholar 

  32. Hahlbrock K 1981 Flavonoids. In: Conn E E (ed) The biochemistry of plants, vol 7. Academic Press London New York, 425–456

    Google Scholar 

  33. Harborne J B 1967 Comparative biochemistry of the flavonoids. Academic Press London New York, 383

    Google Scholar 

  34. Harborne J B 1977 Introduction to ecological biochemistry. Academic Press London New York, 2

    Google Scholar 

  35. Haslam E 1965 Galloyl esters in the Aceraceae. Phytochemistry 4: 495–498

    Article  CAS  Google Scholar 

  36. Haslam E 1966 Chemistry of vegetable tannins. Academic Press London New York, 179

    Google Scholar 

  37. Haslam E 1967 Gallotannins. Part 14. Structure of the gallotannins. J Chem Soc (C) 1734–1738

    Google Scholar 

  38. Haslam E 1969 (+) Catechin-3-gallate and a polymeric procyanidin from Bergenia sp. J Chem Soc (C) 1824–1828

    Google Scholar 

  39. Haslam E 1974 Polyphenol-protein interactions. Biochem J 139: 285–288

    CAS  PubMed  Google Scholar 

  40. Haslam E 1977 Symmetry and promiscuity in procyanidin biochemistry. Phytochemistry 16: 1625–1640

    Article  CAS  Google Scholar 

  41. Haslam E 1982 The metabolism of gallic and hexahydroxydiphenic acid in higher plants. Fortschr Chem Org Naturst 41: 1–46

    Article  CAS  Google Scholar 

  42. Haslam E 1982 Vegetable tannins. In: Conn E E (ed) The biochemistry of plants, vol 7. Academic Press London New York, 527–556

    Google Scholar 

  43. Haslam E, Gupta R K, Al-Shafi S M K, Layden K 1982 The metabolism of gallic acid and hexahydroxydiphenic acid in plants. Part 2. Esters of (S)-hexahydroxydiphenic acid with D-glucopyranose (4Ct). J Chem Soc Perkin I 2525–2534

    Google Scholar 

  44. Haslam E, Haddock E A, Gupta R K 1982 The metabolism of gallic acid and hexahydroxydiphenic acid in plants. Part 3. Esters of (R)- and (S)-hexahydroxydiphenic acid and dehydrohexahydrox- ydiphenic acid with D-glucopyranose (1C4 and related conformations). J Chem Soc Perkin I 2535–2545

    Google Scholar 

  45. Haslam E, Haddock E A, Gupta R K, Al-Shafi S M K, Magnolato D 1982 The metabolism of gallic acid and hexahydroxydiphenic acid in plants. Part 1. Naturally occurring galloyl esters. J Chem Soc Perkin I 2515–2524

    Google Scholar 

  46. Haslam E, Haddock E A, Gupta R K, Al-Shafi S M K, Layden K, Magnolato D 1982 The metabolism of gallic and hexahydroxydiphenic acid in plants: Biogenetic and molecular taxonomic considerations. Phytochemistry 21: 1049–1062

    Google Scholar 

  47. Haslam E, Stangroom J E 1966 The esterase and depsidase activities of tannase. Biochem J 990: 28–31

    Google Scholar 

  48. Haworth R D 1961 Some problems in the chemistry of the gallotannins: Pedler Lecture. Proc Chem Soc 401–410

    Google Scholar 

  49. Haworth R D, da Silva L B 1951 Chebulinic acid. Part 1. J Chem Soc 3511

    Google Scholar 

  50. Haworth R D, da Silva L B 1954 Chebulinic acid. Part 2. J Chem Soc 3611–3617

    Google Scholar 

  51. Herrmann K 1978 Hydroxyzimtsäure und Hydroxybenzosäuren enthaltende Naturstoffe in Pflanzen. Fortschr Chem Org Naturst 35: 73–132

    Article  CAS  Google Scholar 

  52. Hillis W E, Seikel M 1970 Hydrolysable tannins of Eucalyptus delegatensis wood. Phytochemistry 9: 1115–1128

    Article  Google Scholar 

  53. Hoff J E, Oh H I, Armstrong G S, Hoff C A 1980 Hydrophobie interactions in tannic acid - protein complexes. J Agr Food Chem 28: 394–398

    Article  Google Scholar 

  54. Ikeya Y, Taguchi H, Yosioka I, Kobayashi H 1979 The constituents of Schizandra chinensis Baile: Isolation and structure determination of five new lignans, gomisin A, B, C, F and G and the absolute structure of schizandrin. Chem Pharm Bull 27: 1383–1394

    Google Scholar 

  55. Janzen D H 1969 Coevolution. Science 164: 415

    Article  Google Scholar 

  56. Janzen D H 1979 New horizons in the biology of plant defences. In: Rosenthal G A, Janzen D H (eds) Herbivores — their interactions with secondary plant metabolites. Academic Press New York, 331–350

    Google Scholar 

  57. Jochims J C, Taigel G, Schmidt O Th 1968 Protonenresonanze-spektrum und Konforma-tionsbestimmung einiger natürlicher Gerbstoffe. Justus Liebigs Ann Chem 717: 169–185

    Article  CAS  Google Scholar 

  58. Jurd L 1958 Plant polyphenols. III. The isolation of a new ellagitannin from the pellicle of the walnut. J Am Chem Soc 80: 2249–2252

    Article  CAS  Google Scholar 

  59. Keen P C, Haworth R D, Haslam E 1962 Gallotannins. Part 7. Tara gallotannins. J Chem Soc 3814–3818

    Google Scholar 

  60. Knowles P F, Haworth R D, Haslam E 1961 Gallotannins. Part 4. The biosynthesis of gallic acid. J Chem Soc 1854–1859

    Google Scholar 

  61. Loomis W D 1974 Overcoming problems of phenolics and quinones in the isolation of plant enzymes and organelles. Methods Enzymol 31: 528–544

    Article  CAS  PubMed  Google Scholar 

  62. Mayer W 1954 Dehydro-digallusäure. Justus Liebigs Ann Chem 578: 34–44

    Article  Google Scholar 

  63. Mayer W 1973 Otto Theodor Schmidt. Justus Liebigs Ann Chem 1759–1776

    Google Scholar 

  64. Mayer W, Bilzer B, Schauerte K 1971 Isolierung von Castalagin und Vescalagin aus Valoneagerbstoffen. Justus Liebigs Ann Chem 754: 149–151

    Article  CAS  Google Scholar 

  65. Mayer W, Bilzer W, Schilling G 1976 Castavaloninsäure, Isolierung und Strukturmittelung. Justus Liebigs Ann Chem 876–881

    Google Scholar 

  66. Mayer W, Busath H, Schick H 1976 Isovalolaginsäure. Justus Liebigs Ann Chem 2169–2177

    Google Scholar 

  67. Mayer W, Einwiller A, Jochims J C 1967 Die Struktur des Castalins. Justus Liebigs Ann Chem 707: 182–189

    Article  CAS  Google Scholar 

  68. Mayer W, Gorner A, Andra K 1977 Punicalagin und Punicalin, zwei Gerbstoffe aus den Schalen der Granatäpfel. Justus Liebigs Ann Chem 1976–1986

    Google Scholar 

  69. Mayer W, Gunther A, Busath H, Bilzer W, Schilling G 1976 Valolaginsäure. Justus Liebigs Ann Chem 987–995

    Google Scholar 

  70. Mayer W, Kullman F, Schilling G 1971 Die Struktur des Vescalins. Justus Liebigs Ann Chem 747: 51–59

    Article  CAS  Google Scholar 

  71. Mayer W, Kunz N, Loebich F 1965 Die Struktur des Hamamelitannins. Justus Liebigs Ann Chem 688: 232–238

    Article  CAS  Google Scholar 

  72. Mayer W, Schick H, Schilling G 1976 Trillosäure, eine neue Phenolcarbonsäure aus Valoneagerbstoffen. Justus Liebigs Ann Chem 2178–2184

    Google Scholar 

  73. Mayer W, Seitz H, Jochims J C 1969 Die Struktur des Castalins. Justus Liebigs Ann Chem 707: 182–189

    Article  Google Scholar 

  74. Mayer W, Schultz G, Wrede S, Schilling F G 1975 2-O-Cinnamoyl-l-O-galloyl-β-D-glucopyranose aus Rhizoma rhei. Justus Liebigs Ann Chem 946–952

    Google Scholar 

  75. Mayer W, Seitz H Y, Jochims J C, Schauerte K, Schilling G 1971. Struktur des Vescalagins. Justus Liebigs Ann Chem 751: 60–68

    Article  CAS  Google Scholar 

  76. McManus J P, Davis K G, Lilley T H, Haslam E 1981 The association of phenols with proteins. J Chem Soc Comm 309–311

    Google Scholar 

  77. Neish A C, Towers G H N, Chen D, El-Basyouni S Z, Ibrahim R K 1964 The biosynthesis of hydroxybenzoic acids in higher plants. Phytochemistry 3: 485–492

    Article  Google Scholar 

  78. Nielsen B J, Lacour N F, Jensen S R, Bock K 1980 The structure of acer tannin. Phytochemistry 19: 2033

    Article  Google Scholar 

  79. Nierenstein M 1932 Incunabula of tannin chemistry. Edward Arnold London, 116

    Google Scholar 

  80. Nishioka I, Nonaka G, Nishizawa M, Yamagishi T 1982 Tannins and related compounds. Part 5. Structure of Chinese gallotannin. J Chem Soc Perkin I 2963–2968

    Google Scholar 

  81. Nishioka I, Nonaka G, Tanaka T 1982 Tannins and related compounds. Part 3. A new phenolic acid, sanguisorbic acid dilactone and three new ellagitannins sanguins H-l, H-2 and H-3 from Sanguisorba officinalis. J Chem Soc Perkin I 1067–1073

    Google Scholar 

  82. Nishioka I, Nonaka G, Tanaka T, Nita M 1982 A dimeric hydrolysable tannin sanguin H-6 from Sanguisorba officinalis. Chem Pharm Bull 30: 2255–2257

    Article  Google Scholar 

  83. Nishira H, Joslyn M A 1968 The galloyl glucose compounds in green carob pods ( Ceratonia siliqua ). Phytochemistry 7: 2147–2156

    Article  CAS  Google Scholar 

  84. Nonaka G, Harada M, Nishioka I 1980 Eugeniin, a new ellagitannin from cloves. Chem Pharm Bull 28: 685–687

    Article  CAS  Google Scholar 

  85. Nonaka G, Matsumoto Y, Nishioka I 1981 Trapain, a new hydrolysable tannin from Trapa japónica Fleroy. Chem Pharm Bull 29: 1184–1186

    Article  Google Scholar 

  86. Nonaka G, Nishioka I 1983 Tannins and related compounds: Rhubarb. Isolation and structure of a glycerol gallate, gallic acid glucoside gallates, galloyl glucoses and isolindleyin. Chem Pharm Bull 31: 1652–1658

    Google Scholar 

  87. Nonaka G, Nishioka I, Nagasawa T, Oura H 1981 Tannins and related compounds: Rhubarb. Chem Pharm Bull 29: 2862–2870

    Google Scholar 

  88. Nonaka G, Nishizawa N, Yamagishi T, Nishioka I, Baudo H 1982 Novel hydrolysable tannins from Nuphar japonicum. Chem Pharm Bull 30: 1094–1097

    Article  Google Scholar 

  89. Okuda T 1981 Tknnins of medicinal plants and drugs. Heterocycles 15: 1323 - 1342

    Article  CAS  Google Scholar 

  90. Okuda T, Ashida M, Yoshida T 1981 Casuarictin and casuarinin - two new ellagitannins from Casuarina stricta. Heterocycles 16: 1681–1685

    Article  CAS  Google Scholar 

  91. Okuda T, Fujii R, Yoshida T 1980 Revised structures of chebulinic and chebulagic acid. Chem Pharm Bull 28: 3713–3715

    Article  Google Scholar 

  92. Okuda T, Hatano T, Nitta H, Fujii R 1980 Hydrolysable tannins having enantiomeric dehydrohe- xahydroxydiphenoyl group: Revised structure of terchebin and granatin B. Tetrahedron Lett 21: 4361–4364

    Article  CAS  Google Scholar 

  93. Okuda T, Hatano T, Ogawa N 1982 Rugosin D, E, F, and G. Dimeric and trimeric hydrolysable tannins. Chem Pharm Bull 30: 4234–4237

    Google Scholar 

  94. Okuda T, Hatano T, Yasui T 1981 Revised structure of isoterchebin isolated from Cornus officinalis. Heterocycles 16: 1321–1325

    Article  CAS  Google Scholar 

  95. Okuda T, Hatano T, Yazaki K 1982 Dehydrogeraniin, furosinin and furosin, dehydroellagitannins from Geranium thunbergii. Chem Pharm Bull 30: 1113–1116

    Article  CAS  Google Scholar 

  96. Okuda T, Hatano T, Yazaki K 1983 Praecoxin B, C, D and E. Novel ellagitannins from Stachyurus praecox. Chem Pharm Bull 31: 333–336

    Article  CAS  Google Scholar 

  97. Okuda T, Hatano T, Yazaki K, Ogawa N 1982 Rugosin A, B and C and praecoxin A, tannins having a valoneoyl group. Chem Pharm Bull 30: 4230–4233

    Article  CAS  Google Scholar 

  98. Okuda T, Seno K 1978 Mallotusinic acid and mallotinic acid, new hydrolysable tannins from Mallolotus japonicus. Tetrahedron Lett 139–142

    Google Scholar 

  99. Okuda T, Usman-Memon M, Yoshida T 1981 Alnusiin, a novel ellagitannin from Alnus sieboldiana fruits. Heterocycles 16: 1085–1087

    Article  Google Scholar 

  100. Okuda T, Yoshida T, Hatano T 1982 Constituents of Geranium thunbergii Sieb et Zudd. Part 12. Hydrated stereostructure and equilibration of geraniin. J Chem Soc Perkin I 9–14

    Article  Google Scholar 

  101. Okuda T, Yoshida T 1980 13C Nuclear magnetic resonance spectra of corilagin and geraniin. Heterocycles 14: 1743–1747

    Google Scholar 

  102. Okuda T, Yoshida T, Ashida M, Yazaki K 1982 Casuariin, stachyurin and strictinin. New Ellagitannins from Casuarina stricta. Chem Pharm Bull 30: 766–769

    Article  CAS  Google Scholar 

  103. Okuda T, Yoshida T, Hatano T, Koga T, Toh N, Kuriyama N 1982 Circular dichroism of hydrolysable tannins. I. Ellagitannins and gallotannins. Tetrahedron Lett 23: 3937–3940

    Article  CAS  Google Scholar 

  104. Okuda T, Yoshida T, Hatano T, Koga T, Toh N, Kuriyama N 1982 Circular dichroism of hydrolysable tannins. II. Ellagitannins and gallotannins. Tetrahedron Lett 23: 3941–3944

    Google Scholar 

  105. Okuda T, Yoshida T, Hatano T, Yazaki K, Ashida M 1982 Ellagitannins of the Casuarinaceae, Stachyuraceae, Myrtaceae. Phytochemistry 21: 2871–2874

    Google Scholar 

  106. Okuda T, Yoshida T, Koga T, Toh N 1982 Absolute configurations of chebulic, chebulinic and chebulagic acids. Chem Pharm Bull 30: 2655–2658

    Article  Google Scholar 

  107. Okuda T, Yoshida T, Kuwahara M, Usman-Memon M, Shingu T 1982 Agrimoniin and potentillin, an ellagitannin dimer and monomer having an α-glucose core. J Chem Soc Chem Comm 163–164

    Google Scholar 

  108. Okuda T, Yoshida T, Maruyama Y, Usman-Memon M, Shingu T 1982 Gemin B and C, dimeric ellagitannins from Geum japonicum. Chem Pharm Bull 30: 4245–4248

    Article  Google Scholar 

  109. Okuda T, Yoshida T, Usman-Memon M, Shingu T 1982 Structure of gemin A, a new dimeric ellagitannin having α- and β-glucose cores. J Chem Soc Chem Comm 351–353

    Google Scholar 

  110. Ozawa T, Arai N, Takino Y 1978 Structure of a new phenolic glycoside chesnatin from chestnut galls. Agr Biol Chem 42: 1907–1910

    Article  CAS  Google Scholar 

  111. Ozawa T, Haga K, Arai N, Takino Y 1978 Structure of a new phenolic glycoside from chestnut galls. Agr Biol Chem 42: 1511–1514

    Article  CAS  Google Scholar 

  112. Ozawa T, Kobayashi D, Takino Y 1977 Structure of the new phenolic glycosides MP-2 and MP-10 from chestnut galls. Agr Biol Chem 41: 1257–1262

    Article  CAS  Google Scholar 

  113. Ozawa T, Odaira Y, Imegawa H, Takino Y 1980 A new phenolic glycoside acetylcretanin and flavonoids from chestnut galls. Agr Biol Chem 44: 581–587

    Article  CAS  Google Scholar 

  114. Perkin A G, Uyeda Y 1922 Occurrence of a crystalline tannin in the leaves of Acer ginnala. J Chem Soc 66–76

    Google Scholar 

  115. Pohl R, Nahrstedt A, Dumkow K, Janistyn B 1974 Quercetin-galactoside gallate in Euphor- biaceae. Tetrahedron Lett 559–562

    Google Scholar 

  116. Reddy K K, Rajadurai S, Sastry S K N, Nayudamma Y 1964 Studies of the Dhava tannins. 1. The isolation and constitution of a gallotannin from Dhava (Anogeissus latifolia) 17: Aust J Chem 238–245

    Google Scholar 

  117. Roberts E A H, Myers M 1958 Theogallin, a polyphenol occurring in tea. II Identification as a galloyl quinic acid. J Sci Food Agrie 9: 701–705

    Google Scholar 

  118. Robinson W B, Calderón P, van Burén J 1968 Factors influencing the formation of precipitates and hazes by gelatin and condensed and hydrolysable tannins. J Agr Food Chem 16: 479–482

    Article  Google Scholar 

  119. Robinson W B, van Buren J 1969 Formation of complexes between protein and tannic acid. J Agr Food Chem 17: 772–777

    Article  Google Scholar 

  120. Saijo R 1983 Pathway of gallic acid biosynthesis and its esterification with catechins in young tea shoots. Agr Biol Chem 47: 455–460

    Article  CAS  Google Scholar 

  121. Schmidt O Th 1954 Ellagengerbstoffe. Leder 5: 129–134

    CAS  Google Scholar 

  122. Schmidt O Th 1955 Natürliche Gerbstoffe. In: Peach K, Tracey M V (eds) Moderne Methoden der Pflanzenanalyse, vol III. Springer Berlin, 517–548

    Google Scholar 

  123. Schmidt O Th 1956 Gallotannine und Ellagen-Gerbstoffe. Fortschr Chem Org Naturst 13: 71–136

    Google Scholar 

  124. Schmidt O Th 1957 Über Chebulagsäure und Chebulinsäure. Leder 8: 106

    CAS  Google Scholar 

  125. Schmidt O Th, Bernauer K 1954 Brevifolin und Brevifolin-Carbonsäure. Justus Liebigs Ann Chem 588: 211–230

    Article  CAS  Google Scholar 

  126. Schmidt O Th, Blin F, Lademann R 1952 Über die Bindung der Ellagsäure in Corilagin und Chebulagsäure. Justus Liebigs Ann Chem 576: 75–93

    Article  CAS  Google Scholar 

  127. Schmidt O Th, Demmler K 1952 Optisch aktiv 2,3,4,2’,3’,4’-hexamethoxydiphenylcarbonsäure- 6,6’. Justus Liebigs Ann Chem 576: 85–93

    Article  CAS  Google Scholar 

  128. Schmidt O Th, Demmler K 1954 Racemische und optisch aktive 2,3,4,2’,3’,4’-Hexaoxydiphenyl- carbonsäure-6,6’. Justus Liebigs Ann Chem 586: 170–193

    Google Scholar 

  129. Schmidt O Th, Ebert W, Koff M 1969 1,3,4,6-Tetragalloyl-β-D-glucose aus Algarobilla. Justus Liebigs Ann Chem 729: 251–252

    Google Scholar 

  130. Schmidt O Th, Komarek E 1955 Valoneasäure. Justus Liebigs Ann Chem 591: 156–176

    Google Scholar 

  131. Schmidt O Th, Lademann R 1951 Corilagin, ein weiterer kristallisierter Gerbstoff aus Divi-Divi. Justus Liebigs Ann Chem 571: 232–238

    Article  CAS  Google Scholar 

  132. Schmidt O Th, Mayer W 1956 Natürliche Gerbstoffe. Angew. Chem 68: 103–106

    Google Scholar 

  133. Schmidt O Th, Schanz R, Eckert R, Wurmb R 1967 Brevilagin 1. Justus Liebigs Ann Chem 706: 131–153

    Google Scholar 

  134. Schmidt O Th, Schanz R, Wurmb R, Groebke W 1967 Brevilagin 2. Justus Liebigs Ann Chem 706: 154–168

    Article  CAS  Google Scholar 

  135. Schmidt O Th, Schmidt DM 1953 Über das Vorkommen von Corilagin in Myrabolanen. Justus Liebigs Ann Chem 578: 31–34

    Article  Google Scholar 

  136. Schmidt O Th, Schmidt D M, Herok J 1954 Die Konstitution und Konfiguration des Corilagins. Justus Liebigs Ann Chem 587: 67–80

    Article  CAS  Google Scholar 

  137. Schmidt O Th, Schulz J, Feisser H 1967 Die Gerbstoffe der Myrabolanen. Justus Liebigs Ann Chem 706: 187–212

    Article  CAS  Google Scholar 

  138. Schmidt O Th, Schulz J, Wurmb R 1967 Terchebin. Justus Liebigs Ann Chem 706: 169–179

    Article  CAS  Google Scholar 

  139. Schmidt O Th, Wurtele L, Harreus A 1965 Penduculagin, eine 2,3:4,6-Di-S-(-)hexahydroxydiphenoyl-D-glucose aus Knoppern. Justus Liebigs Ann Chem 690: 150–162

    Article  CAS  Google Scholar 

  140. Uddin M, Haslam E 1967 Gallotannins. Part 15. Some observations on the structure of chebulinic acid and its derivatives. J Chem Soc (C) 2381–2384

    Google Scholar 

  141. Wagner H, Iyengar M A, Seligmann O, El-Sissi H I, Saleh NAM, El-Negoumy S I 1974 Prunin- 0-6’-gallate aus Acacia farnesiana. Phytochemistry 13: 2843–2844

    Article  Google Scholar 

  142. White T 1957 Tannins, their occurrence and significance. J Sci Food Agr 8: 377–385

    Article  CAS  Google Scholar 

  143. Wilkins C K, Böhm B A 1976 Ellagitannins from Tellima grandiflora. Phytochemistry 15: 211–214

    Article  CAS  Google Scholar 

  144. Zenk M H 1964 Zur Frage der Biosynthese von Gallusäure. Z Naturforschung 19B: 83–84

    Google Scholar 

  145. Zenk M H 1978 Recent work on cinnamoyl CoA derivatives. In: Swain T, Harborne J B, van Sumere C (eds) Recent advances in phytochemistry, vol 12. Biochemistry of plant phenolics. Plenum Press London, 139–176

    Google Scholar 

Download references

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1989 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Haslam, E. (1989). Gallic Acid Derivatives and Hydrolyzable Tannins. In: Rowe, J.W. (eds) Natural Products of Woody Plants. Springer Series in Wood Science. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-74075-6_13

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-74075-6_13

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-74077-0

  • Online ISBN: 978-3-642-74075-6

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics