Secondary Plant Substances

Nonsteroidal Triterpenoids
  • Horst-Robert Schütte
Part of the Progress in Botany/Fortschritte der Botanik book series (BOTANY, volume 50)


Triterpenoids are a group of natural products containing a carbon skeleton of 30 carbon atoms based on 6 isoprene units or biosynthetically derived from such C30 compounds by degradation. Therefore, also the steroids and their precursors belong to the triterpenoids, but traditionally they are considered as a special group. Recent results on the biochemistry of steroids were discussed last year (Progr Bot 49:117 ff). Nonsteroidal triterpenoids are mainly restricted to the plant kingdom, but are ubiquitous amongst the flowering plants (Basu and Rastogi 1967; Kulshreshtha et al. 1972; Brüning and Wagner 1978; Chandler and Hooper 1979; Pant and Rastogi 1979; Das and Mahato 1983; Tanaka and Kasai 1984; Boar 1984; Baas 1985; Conolly and Hill 1986). The majority of natural triterpenes are pentacyclic compounds. Most of them are alcohols (3-OH). They are found free and as glycosides or esters. Free triterpenes are often components of resins or latex. There are some discussions on a role of pentacyclic 3 β-hydroxy-triterpenes in membrane systems (Nes and Heftmann 1981).


Ursolic Acid Oleanolic Acid Fusidic Acid Navel Orange Citrus Juice 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


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  1. Aberhart DJ, Caspi E (1979) J Am Chem Soc 101:1013–1019.CrossRefGoogle Scholar
  2. Anding C, Rohmer M, Ourisson G (1976) J Am Chem Soc 98:1274–1275.PubMedCrossRefGoogle Scholar
  3. Arigoni D, Barton DHR, Corey EJ, Jeger O, Caglioti L, Dev S, Ferrini PG, Glazier ER, Melera A,Pradhan SK, Schaffner K, Sternhell S, Templeton JF, Tobinaga S (1960) Experientia 16:41–49.CrossRefGoogle Scholar
  4. Atallah AM, Aexel RT, Ramsey RB, Threlkeld S, Nicholas HJ (1975) Phytochemistry 14:1927–1932.CrossRefGoogle Scholar
  5. Augus-cinska E, Szakiel A, Wilkomirski B, Kasprzyk Z (1985) Phytochemistry 24:1713–1715.CrossRefGoogle Scholar
  6. Baas WJ (1982) Acta Bot Neerl 31:449–476.Google Scholar
  7. Baas WJ (1985) Phytochemistry 24:1875–1889.CrossRefGoogle Scholar
  8. Baisted DJ (1971) Biochem J 124:375–383.PubMedGoogle Scholar
  9. Baisted DJ, Capstack E Jr, Nes WR (1962) Biochemistry 1:537–541.PubMedCrossRefGoogle Scholar
  10. Balliano G, Caputo O, Viola F, Delprino L Cattel L (1983a) Phytochemistry 22:909–913.CrossRefGoogle Scholar
  11. Balliano G, Caputo O, Viola F, Delprino L Cattel L (1983b) Phytochemistry 22:915–921.CrossRefGoogle Scholar
  12. Banthorpe DV, Charlwood BV (1980) Secondary plant products. In: Bell EA, Charlwood BV (eds) Encyclopedia of Plant Physiology. Springer, Berlin Heidelberg New York. NS Vol 8:185–220.Google Scholar
  13. Barthe GA, Jourdan PS, Mclntosh CA, Mansell RL (1987) J Plant Physiol 127:55–65.Google Scholar
  14. Barton DHR, Pradhan SK, Sternhell S, Templeton JF (1961) J Chem Soc 225-275.Google Scholar
  15. Barton DHR, Gosden AF, Mellows G, Widdowson DA (1969) Chem Commun 184-186.Google Scholar
  16. Barton DHR, Mellows G, Widdowson DA, Wright JJ (1971) J Chem Soc (C) 1142-1148.Google Scholar
  17. Barton DHR, Jarman TR, Watson KG, Widdowson DA, Boar RB, Damps K (1974) Chem Commun 861.Google Scholar
  18. Barton DHR, Jarman TR, Watson KG, Widdowson DA, Boar RB, Damps K (1975) J Chem Soc Perkin I 1134–1138.CrossRefGoogle Scholar
  19. Basu N, Rastogi RP, (1967) Phytochemistry 6:1249–1270.CrossRefGoogle Scholar
  20. Bennett RD (1971) Phytochemistry 10:3065–3068.CrossRefGoogle Scholar
  21. Boar RB (1984) Nat Prod Rep 1:53–65.CrossRefGoogle Scholar
  22. Bouvier P, Berger Y, Rohmer M, Ourisson G (1980) Eur J Biochem 112:549–556.PubMedCrossRefGoogle Scholar
  23. Brüning R, Wagner H (1978) Phytochemistry 17:1821–1858.CrossRefGoogle Scholar
  24. Capstack E, Rosin N, Blondin GA, Nes WR (1965) J Biol Chem 240:3258–3263.Google Scholar
  25. Caputo O, Delprino L, Viola F, Caramiello R, Balliano G (1983) Planta Med 49:176–180.PubMedCrossRefGoogle Scholar
  26. Caspi E, Mulheim LJ (1970) J Am Chem Soc 92:404–406.PubMedCrossRefGoogle Scholar
  27. Caspi E, Greig JB, Zander JM (1968a) Biochem J 109:931–932.PubMedGoogle Scholar
  28. Caspi E, Zander JM, Greig JB, Mallory FB, Conner RL, Landrey J (1968b) J Am Chem Soc 90:3563–3564.CrossRefGoogle Scholar
  29. Caspi E, Greig JB, Zander JM, Mandelbaum A (1969) Chem Commun 28-29.Google Scholar
  30. Cattel L, Balliano G, Caputo O, Viola F (1981) Planta Med 41:328–336.PubMedCrossRefGoogle Scholar
  31. Chandler F, Hooper SN (1979) Phytochemistry 18:711–724.CrossRefGoogle Scholar
  32. Ciborowski P, Wilkomirski B, Zdrojewski W, Kasprzyk Z (1983) Phytochemistry 22:107–109.CrossRefGoogle Scholar
  33. Coates RM (1976) Progr Chem Org Nat Prod 33:73–230.Google Scholar
  34. Connolly JD, Hill RA (1986) Nat Prod Rep 3:421–442.CrossRefGoogle Scholar
  35. Connolly JD, Overton KH, Polonskiy J(1970) Prog Phytochemistry 2:385–455.Google Scholar
  36. Corey EJ, Gross SK (1968) J Am Chem Soc 90:5045–5046.CrossRefGoogle Scholar
  37. Corey EJ, OrtizDeMon-tellano PR (1967) J Am Chem Soc 89:3362–3363.PubMedCrossRefGoogle Scholar
  38. Croteau R, Loomis WD (1973) Phytochemistry 12:1957–1965.CrossRefGoogle Scholar
  39. Das MC, Mahato SB (1983) Phytochemistry 22:1071–1095.CrossRefGoogle Scholar
  40. Datta S, Nicholas HJ (1968) Phytochemistry 7:955–956.CrossRefGoogle Scholar
  41. Delprino L, Balliano G, Cattel L, Benveniste P, Bouvier P (1983) Chem Commun 381-382.Google Scholar
  42. Delprino L, Caputo O, Balliano G, Berta S, Bouvier P, Cattel L (1984) J Chem Res (S) 254-255.Google Scholar
  43. Dietsch A, Delprino L, Benveniste P (1980) J Chem Res (S) 60-61.Google Scholar
  44. Dreyer DL (1965) J Org Chem 30:749–751.CrossRefGoogle Scholar
  45. Dreyer DL (1966a) J Org Chem 31:2279–2281.CrossRefGoogle Scholar
  46. Dreyer DL (1966b) Phytochemistry 5:367–378.CrossRefGoogle Scholar
  47. Dreyer DL (1968) Fortschr Org Chem Naturst 26:190–244.Google Scholar
  48. Dreyer DL (1984) In: Nes WD, Fuller G, Tsai LS (eds) Biochemistry and Function of Isopentenoids in Plants. Decker, New York. pp 209–228.Google Scholar
  49. Ekong DEU, Ibiyemi SA (1985) Phytochemistry 24:2259–2261.CrossRefGoogle Scholar
  50. Ekong DEU, Ibiyemi SA, Olagbemi EO (1971) Chem Commun 1117-1118.Google Scholar
  51. Ekundayo O (1983) Z Pflanzenphysiol 112:139–146.Google Scholar
  52. Elder JW, Benveniste P, Fonteneau P (1977) Phytochemistry 16:490–492.CrossRefGoogle Scholar
  53. Eschenmoser A, Ruzicka L, Jeger O, Arigoni D (1955) Helv Chim Acta 38:1890–1904.CrossRefGoogle Scholar
  54. Ghisalberti EL, DeSouza NJ, Rees HH, Goodwin TW (1970) Phytochemistry 9:1817–1823.CrossRefGoogle Scholar
  55. Godtfredsen WO, Lorek H, VanTamelen EE, Willet JD, Clayton RB (1968) J Am Chem Soc 90:208–209.PubMedCrossRefGoogle Scholar
  56. Goodwin TW (1971) Biochem J 123:293–329.PubMedGoogle Scholar
  57. Goodwin TW (1981) In: Porter JW, Spurgeon SL (eds) Biosynthesis of Isoprenoid Compounds. Wiley, New York. Vol 1, pp 443–480.Google Scholar
  58. Groeneveld HW (1976) Acta Bot Neerl 25:459–473.Google Scholar
  59. Groeneveld HW, Koning J (1976) Acta Bot Neerl 25:227–250.Google Scholar
  60. Groeneveld HW, Roelvink PW (1982) Planta 154:347–351.CrossRefGoogle Scholar
  61. Groeneveld HW, VanDenBurg B (1984) Plant Sci Lett 33:81–91.CrossRefGoogle Scholar
  62. Groeneveld HW, Hagemann J, Vallenga ATN (1982) Phytochemistry 21:1589–1597.Google Scholar
  63. Harrison DM (1985) Nat Prod Rep 2:525–560.PubMedCrossRefGoogle Scholar
  64. Hasegawa S (1976) Agric Food Chem 24:24–26.CrossRefGoogle Scholar
  65. Hasegawa S, Herman Z (1985) Phytochemistry 24:1973–1974.CrossRefGoogle Scholar
  66. Hasegawa S, Herman Z (1986) Phytochemistry 25:2523–2524.CrossRefGoogle Scholar
  67. Hasegawa S, Hoagland JE (1977) Phytochemistry 16:469–471.CrossRefGoogle Scholar
  68. Hasegawa S, Bennett RD, Maier VP (1972a) J Agric Food Chem 20:435–437.CrossRefGoogle Scholar
  69. Hasegawa S, Bennett RD, Maier VP, King AD jr (1972b) J Agric Food Chem 20:1031–1034.PubMedCrossRefGoogle Scholar
  70. Hasegawa S, Maier VP, Bennett RD (1974a) Phytochemistry 13:103–105.CrossRefGoogle Scholar
  71. Hasegawa S, Maier VP, King AD jr (1974b) J Agric Food Chem 22:523–526.PubMedCrossRefGoogle Scholar
  72. Hasegawa S, Maier VP, Border SN, Bennett RD (1974c) J Agric Food Chem 22:1093–1096.PubMedCrossRefGoogle Scholar
  73. Hasegawa S, Brewster LC, Maier VP (1974d) J Food Sci 38:1153–1155.CrossRefGoogle Scholar
  74. Hasegawa S, Bennett RD, Verdon CP (1980a) J Agric Food Chem 28:922–925.CrossRefGoogle Scholar
  75. Hasegawa S, Bennett RD, Verdon CP (1980b) Phytochemistry 19:1445–1447.Google Scholar
  76. Hasegawa S, Pelton VA, Bennett RD (1983) J Agric Food Chem 31:1002–1004.CrossRefGoogle Scholar
  77. Hasegawa S, Bennett RD, Maier VP (1984a) Phytochemistry 23:1601–1603.CrossRefGoogle Scholar
  78. Hasegawa S, Dillberger AM, Choi GY (1984b) J Agric Food Chem 32:457–459.CrossRefGoogle Scholar
  79. Hasegawa S, Vandercook CE, Choi GY, Herman Z, Ou P (1985) J Food Sci 50:330–332.CrossRefGoogle Scholar
  80. Hasegawa S, Herman Z, Ou P (1986a) Phytochemistry 25:542–543.CrossRefGoogle Scholar
  81. Hasegawa S, Herman Z, Orme E, Ou P (1986b) Phytochemistry 25:2783–2785.CrossRefGoogle Scholar
  82. Hasegawa S, Maier VP, Herman Z, Ou P (1986c) Phytochemistry 25:1323–1325.CrossRefGoogle Scholar
  83. Hattori T, Igarashi H, Iwasaki S, Okuda S (1969) Tetrahedron Lett 1023-1026.Google Scholar
  84. Herman Z, Hasegawa S (1985) Phytochemistry 24:2911–2913.CrossRefGoogle Scholar
  85. Herman Z, Hasegawa S, Ou P (1985) J Food Sci 50:118.CrossRefGoogle Scholar
  86. Herman Z, Bennett RD, Ou P, Fong CH, Hasegawa S (1987) Phytochemistry 26:2247–2250.CrossRefGoogle Scholar
  87. Heupel RC, Nes WD (1985) Phytochemistry 24:2905–2909.CrossRefGoogle Scholar
  88. Horan H, McCormick JP, Arigoni D (1973) Chem Commun 73-74.Google Scholar
  89. Hsu AC, Hasegawa S, Maier VP, Bennett RD (1973) Phytochemistry 12:563–567.CrossRefGoogle Scholar
  90. Jaenicke L, Marner FJ (1986) Prog Chem Org Nat Prod 50:1–25.Google Scholar
  91. Janiszowska W, Kasprzyk Z (1977) Phytochemistry 16:1919–1923.CrossRefGoogle Scholar
  92. Jaziri M, Homes J, Vanhaeien M (1987) Phytochemistry 26:999–1000.CrossRefGoogle Scholar
  93. Kasprzyk Z, Wojciechowski Z (1967) Phytochemistry 6:69–75.CrossRefGoogle Scholar
  94. Kasprzyk Z, Wojciechowski Z, Janiszowska W (1970) Phytochemistry 9:561–564.CrossRefGoogle Scholar
  95. Kasprzyk Z, Sliwowski J, Skwarko B (1972) Phytochemistry 11:1961–1966.CrossRefGoogle Scholar
  96. Kawaguchi A, Okuda S (1970) Chem Commun 1012-1013.Google Scholar
  97. Kintia PK, Wojciechowski ZA, Kasprzyk Z (1974) Acta Biochim Pol 21:263–269.PubMedGoogle Scholar
  98. Krick W, Marner FJ, Jaenicke L (1983) IZ Naturforsch 38c:689–692.Google Scholar
  99. Lavie D, Glotter E (1971) Fortschr Chem Org Naturst 29:307–362.PubMedGoogle Scholar
  100. Loomis O, Croteau R (1980) Lipids, structure and function. In: Stumpf PK, Conn EE (eds) The Biochemistry of Plants. A Comprehensive Treatise. Academic Press, London New York. Vol 4, pp 364–418.Google Scholar
  101. Maier VP, Margileth DA (1969) Phytochemistry 8:243–248.CrossRefGoogle Scholar
  102. Maier VP, Hasegawa S, Hera E (1969) Phytochemistry 8:405–407.CrossRefGoogle Scholar
  103. Maier VP, Brewster LC, Hsu AC (1973) J Agric Food Chem 21:490–495.CrossRefGoogle Scholar
  104. Mallory FB, Conner RL, Landrey J, Zander JM, Greig JB, Caspi E (1968) J Am Chem Soc 90:3564–3566.CrossRefGoogle Scholar
  105. Mclntosh CA, Mansell RL (1983) J Agric Food Chem 31:319–325.CrossRefGoogle Scholar
  106. Mclntosh CA, Mansell RL, Rouseff RL (1982) J Agric Food Chem 30:689–692.CrossRefGoogle Scholar
  107. Mercer El, Goodwin TW (1963) Biochem J 88:46p.Google Scholar
  108. Mulheim LJ, Caspi E (1971) J Biol Chem 246:2494–2501.Google Scholar
  109. Nemethy EK, Skurkrud C, Piazza GJ, Calvin M (1983) Biochim Biophys Acta 760:343–349.CrossRefGoogle Scholar
  110. Nes WD, Heftmann E (1981) J Nat Prod 44:377–400.CrossRefGoogle Scholar
  111. Nes WD, Benson M, Heftmann E (1981) Phytochemistry 20:2299–2300.CrossRefGoogle Scholar
  112. Nicol KJ, Chandler BV (1978) J Sci Food Agric 29:795–802.CrossRefGoogle Scholar
  113. Niemann GJ (1985) Planta 166:51–56.CrossRefGoogle Scholar
  114. Niemann GJ, Baas WJ (1985a) J Plant Physiol 118:219–226.Google Scholar
  115. Niemann GJ, Baas WJ (1985b) Physiol Plant 64:371–376.CrossRefGoogle Scholar
  116. Niemann J, Koerselman-Kooy JW (1987) J Plant Physiol 129:395–405.Google Scholar
  117. Nowacki E, Jurzysta M, Dietrych-Szöstak D (1976) Biochem Physiol Pflanz 169:183–186.Google Scholar
  118. Palmer MA, Bowden BJ (1977) Phytochemistry 16:459–463.CrossRefGoogle Scholar
  119. Pant P, Rastogi RP (1979) Phytochemistry 18:1095–1108.CrossRefGoogle Scholar
  120. Peri I, Mor U, Heftmann E, Bondi A, Tencer Y (1979) Phytochemistry 18:1671–1674.CrossRefGoogle Scholar
  121. Piazza GJ, Saggese EJ, Spletzer KM (1987a) Plant Physiol 83:177–180.PubMedCrossRefGoogle Scholar
  122. Piazza GJ, Saggese EJ, Spletzer KM (1987b) Plant Physiol 83:181–184.PubMedCrossRefGoogle Scholar
  123. Polonsky J (1973) Prog Chem Org Nat Prod 30:101–150.Google Scholar
  124. Ponsinet G, Ourisson G (1967) Phytochemistry 6:1235–1243.CrossRefGoogle Scholar
  125. Ponsinet G, Ourisson G (1968) Phytochemistry 7:757–764.CrossRefGoogle Scholar
  126. Rallier A, Bouvier P, Cattel L, Narula A, Benveniste P (1983) Biochem Soc Trans 11:537–543.Google Scholar
  127. Rees H, Mercer El, Goodwin TW (1966) Biochem J 99:726–734.PubMedGoogle Scholar
  128. Rees HH, Britton G, Goodwin TW (1968) Biochem J 106:659–665.PubMedGoogle Scholar
  129. Rohmer M, Ourisson G (1976) Tetrahedron Lett 3641-3644.Google Scholar
  130. Rohmer M, Anding C, Ourisson G (1980a) Eur J Biochem 112:541–547.PubMedCrossRefGoogle Scholar
  131. Rohmer M, Bouvier P, Ourisson G (1980b) Eur J Biochem 112:557–560.PubMedCrossRefGoogle Scholar
  132. Rohmer M, Bouvier-Navé P, Ourisson G (1984) J Gen Microbiol 130:1137–1150.Google Scholar
  133. Rouseff RL, Nagy S (1982) Phytochemistry 21:85–90.CrossRefGoogle Scholar
  134. Rowan MG, Dean PDG (1972) Phytochemistry 11:3111–3118.CrossRefGoogle Scholar
  135. Rowan MG, Dean PDG, Goodwin TW (1971) FEBS Lett 12:229–232.PubMedCrossRefGoogle Scholar
  136. Ruzicka L (1959) Proc Chem Soc 341-360.Google Scholar
  137. Ruzicka L (1963) Pure Appl Chem 6:493–523.CrossRefGoogle Scholar
  138. Scragg AH, Allan EJ (1986) Plant Cell Rep 5:356–359.CrossRefGoogle Scholar
  139. Seo S, Tomita Y, Tori K (1975a) Chem Commun 270-271.Google Scholar
  140. Seo S, Tomita Y, Tori K (1975b) Chem Commun 954-955.Google Scholar
  141. Seo S, Tomita Y, Tori K (1981) J Am Chem Soc 103:2075–2080.CrossRefGoogle Scholar
  142. Seo S, Tomita Y, Tori K, Yoshimura Y (1980) Chem Commun 1275-1277.Google Scholar
  143. Seo S, Uomori A, Yoshimura Y, Takeda K, Sankawa U, Ebizuka Y, Seto H (1986) Chem Commun 1141-1143.Google Scholar
  144. Sharma RK (1970) Phytochemistry 9:565–568.CrossRefGoogle Scholar
  145. Sliwowski J, Kasprzyk Z (1974) Phytochemistry 13:1441–1449.CrossRefGoogle Scholar
  146. Struby K, Janiszowska W, Kasprzyk Z (1972) Phytochemistry 11:1733–1736.CrossRefGoogle Scholar
  147. Suga T, Shishibori T (1975) Phytochemistry 14:2411–2417.CrossRefGoogle Scholar
  148. Szyja W, Wilkomirski B, Kasprzyk Z (1983) Phytochemistry 22:111–113.CrossRefGoogle Scholar
  149. Tanaka O, Kasai R (1984) Prog Chem Org Nat Prod 46:1–76.Google Scholar
  150. Taylor DAH (1984) Prog Chem Org Nat Prod 45:1–102.Google Scholar
  151. Tomita Y, Seo S (1973) Chem Commun 707-708.Google Scholar
  152. Tomita Y, Arata M, Ikeshiro Y (1985) Chem Commun 1087-1088.Google Scholar
  153. Warnaar F (1981) Phytochemistry 20:89–91.CrossRefGoogle Scholar
  154. Warnaar F (1987) Phytochemistry 26:2715–2721.CrossRefGoogle Scholar
  155. Wilkomirski B (1985) Phytochemistry 24:3066–3067.CrossRefGoogle Scholar
  156. Wilkomirski B (1987) Phytochemistry 26:1635–1637.CrossRefGoogle Scholar
  157. Wojciechowski ZA (1975) Phytochemistry 14:1740–1753.CrossRefGoogle Scholar
  158. Wojciechowski ZA (1983) Biochem Soc Trans 11:565–568.PubMedGoogle Scholar
  159. Wojciechowski ZA (1987) In: Schreiber K, Schütte HR, Sembdner G (eds) Conjugated Pland Hormones, Structure, Metabolism and function. Deutscher Verlag der Wissensch, Berlin. pp 297–307.Google Scholar
  160. Zander JM, Wigfield DC (1970) Chem Commun 1599-1600.Google Scholar
  161. Zander JM, Greig JB, Caspi E (1970) J Biol Chem 245:1247–1254.PubMedGoogle Scholar
  162. Zundel M, Rohmer M (1985) Eur J Biochem 150:35–39.PubMedCrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1989

Authors and Affiliations

  • Horst-Robert Schütte
    • 1
  1. 1.Institut für Biochemie der Planzen des Forschungsbereiches Biowissenschaften und MedizinAkademie der Wissenschaften der DDRHalle (Saale)GDR

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