Monoaryl Natural Products

  • O. Theander
  • L. N. Lundgren
Part of the Springer Series in Wood Science book series (SSWOO)

Abstract

In this brief review we will generally restrict ourselves to monoaryl compounds found in woody plants of commercial interest in forestry and agriculture. Because similar monoaryl compounds are often found both in wood and in bark and because there is growing interest in whole-tree utilization, as well as in the use of plant phenols and other extractives as chemicals and other technical products, we will also include bark. Monoaryl compounds in leaves, needles, or other parts of trees — in particular when they illustrate interesting structural features — will be noted to some extent in relation to the chemistry of wood to which they may be translocated.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Agrawal PK, Rastogi RP, 1981 Terpenoids from Cedrus deodara. Phytochemistry 20: 1319–1321CrossRefGoogle Scholar
  2. 2.
    Ahluwalia VK, Seshadri TR, 1957 Constitution of dalbergin. Part. II. J Chem Soc 970–972Google Scholar
  3. 3.
    Ahmed J, Shamsuddin KM, Zaman A, 1984 A pyranocoumarin from Atlantica ceylanica. Phytochemistry 23: 2098–2099CrossRefGoogle Scholar
  4. 4.
    Aiba JC, Gottlieb OR, Maia JGS, Pagliosa FM, Yoshida M, 1978 Benzofuranoid neolignans from Licaria armeniaca. Phytochemistry 17: 2038–2039CrossRefGoogle Scholar
  5. 5.
    Alvarenga MA, et al. (21 authors) 1978 Dihydroisocoumarins and phthalide from wood samples infested by fungi. Phytochemistry 17:511–516Google Scholar
  6. 6.
    Andersson R, Lundgren LN, 1988 Monoaryl and cyclohexenone glycosides from needles of Pinus sylvestris. Phytochemistry 27: 559–562CrossRefGoogle Scholar
  7. 7.
    Andrade CHS, Braz Filho R, Gottlieb OR, 1980 Neolignans from Aniba ferrea. Phytochemistry 19: 1191–1194CrossRefGoogle Scholar
  8. 8.
    Anjaneyulu ASR, Rao AM, Rao VK, Row LR, 1975 The lignans of Gmelina asiatica. Phytochemistry 14: 824CrossRefGoogle Scholar
  9. 9.
    Archangelsky K, 1901 Uber Rhododendrol, Rhododendrin und Andromedotoxin. Arch Exp Pathol Pharmacol 46: 313CrossRefGoogle Scholar
  10. 10.
    Arisawa M, Handa SS, McPherson DD, Lankin DC, Cordell GA, Fong HHS, Farnsworth NR, 1984 Cleosmine A from Simaba multiflora, Soulamea soulameoides, and Matayba arborescens. J Nat Prod 47: 300–307Google Scholar
  11. 11.
    Barton G M, 1968 Significance of Western hemlock phenolic extractives in pulping and lumber. Forest Prod J 18 (5): 76–80Google Scholar
  12. 12.
    Bate-Smith EC, 1962 The simple polyphenolic constituents of plants. In: W E Hillis (ed) Wood extractives. Academic Press New York, 133–158Google Scholar
  13. 13.
    Bhattacharjee SR, Mullick DK, 1960 Isolation of scopoletin, skimmin and umbelliferone from the trunk-bark of Skimmia laureola Hook. J Indian Chem Soc 37: 420–422Google Scholar
  14. 14.
    Bhide KS, Mujumdar RB, Rama Rao AV, 1977 Phenolics from the bark of Chloroxylon smetenia D C. Indian J Chem 15B: 440–444Google Scholar
  15. 15.
    Biswas GK, Chatterjee A, 1970 Isolation and structure of acronylin: a new phenolic compound from Acronychia laurifolia. Chem Ind (London) 20: 654–655Google Scholar
  16. 16.
    Bittencourt AM, Gottlieb OR, Mors WB, Magalhaes MT, Mageswaran S, Ollis WD, Sutherland IO, 1971 The natural occurrence of 6-steryl-2-pyrones and their synthesis. Tetrahedron 27: 1043–1048CrossRefGoogle Scholar
  17. 17.
    Black RA, Rosen AA, Adams SL, 1953 The chromatographic separation of hardwood extractive components giving color reactions with phloroglucinol. J Am Chem Soc 75: 5344–5346CrossRefGoogle Scholar
  18. 18.
    Braz Filho R, Diaz DPP, Gottlieb OR, 1980 Tetronic acid and diarylpropanes from Iryanthera elliptica. Phytochemistry 19: 455–459CrossRefGoogle Scholar
  19. 19.
    Braz Filho R, Magalhaes AF, Gottlieb OR, 1970 New coumarins from Brosimum paraense. An Acad Brasil Cienc 42: 139–142Google Scholar
  20. 20.
    Braz Filho R, Magalhaes AF, Gottlieb OR, 1971 Brosiparin and other coumarins from Brosimum rubescens. An Acad Brasil Cienc 43: 585–586Google Scholar
  21. 21.
    Braz Filho R, Magalhaes AF, Gottlieb OR, 1972 Coumarins from Brosimum rubescens. Phytochemistry 11: 3307–3310Google Scholar
  22. 22.
    Braz Filho R, De Moraes MPL, Gottlieb OR, 1980 Pterocarpans from Swartzia laevicar-Phytochemistry 19: 2003–2006Google Scholar
  23. 23.
    Briggs LH, Cambie RC, 1958 The constituents of Phebalium nudum Hook. I. The bark. Tetrahedron 2: 256–270CrossRefGoogle Scholar
  24. 24.
    Burden RS, Kemp MS, 1983 (-)-7-Hydroxycalamenene, a phytoalexin from Tilia europea. Phytochemistry 22: 1039–1040Google Scholar
  25. 25.
    Campos AM, Khac DD, Fetizon M, 1987 Chromones from Dictyoloma incandescetts.Phytochemistry 26: 2819–2823CrossRefGoogle Scholar
  26. 26.
    Carpenter I, McGarry EJ, Scheinmann F, 1971 The isolation and structure of nine coumarins from the bark of Mammea africana G. Don. J Chem Soc (C), 3783–3790Google Scholar
  27. 27.
    Carpenter R C, Sotheeswaran S, Sultanbawa MUS, Balasubramaniam S, 1980 (-)-5-Methyl- mellein and catechol derivatives from four Semecarpus species. Phytochemistry 19: 445–447Google Scholar
  28. 28.
    Chabeau E, 1938 Chemical composition of the bark of Nemuaron humboldtii. Bull Acad Roy Med Belg 3: 46–66Google Scholar
  29. 29.
    Chakraborty DP, Chowdhury BK, 1967 Mexoticin, a new coumarin from Murraya exotica. Tetrahedron Lett 36: 3471–3473CrossRefGoogle Scholar
  30. 30.
    Chakraborty DP, Roy S, Chakraborty A, Mandai AK, Chowdhury BK, 1980 Structure and synthesis of mexolide: a new antibiotic dicoumarin from Murraya exotica. Tetrahedron 36: 3563–3564CrossRefGoogle Scholar
  31. 31.
    Challice JS, 1973 Distribution of phenols amongst the various tissues of the Pyrus stem. J Sci Food Agric 24: 285–293CrossRefGoogle Scholar
  32. 32.
    Chan WR, Taylor DR, Willis CR, 1967 The structure of sorbifolin, a chromone from Spathelia sorbifolia L., J Chem Soc (C) 2540–2542Google Scholar
  33. 33.
    Chapelle JP, 1973 Isolement de dérivés seco-iridoides d’Anthocleista zambesiaca. Phytochemistry 12: 1191–1192CrossRefGoogle Scholar
  34. 34.
    Chapelle JP, 1976 Grandifloroside et methylgrandifloroside, glucosides iridoides nouveaux d’Anthocleista grandiflora. Phytochemistry 15: 1305–1307CrossRefGoogle Scholar
  35. 35.
    Chatterjee A, Bhattacharya A, 1959 The isolation and constitution of marmin, a new coumarin from Aegle marmelos Correa. J Chem Soc 1922–1924Google Scholar
  36. 36.
    Chatterjee A, Dhara KP, Rej RN, Ghosh PC, 1977 Hexacosylferulate, a phenolic constituent of Pinus roxburghii. Phytochemistry 16: 397–398CrossRefGoogle Scholar
  37. 37.
    Chatterjee A, Dutta CP, Bhattacharyya S, Audier HE, Das BC, 1967 The structure of marmin. Tetrahedron Lett 5: 471–473CrossRefGoogle Scholar
  38. 38.
    Chatterjee A, Roy SK, 1959 Constituents of the heartwood of Aegle marmelos. J Indian Chem Soc 36: 267–269Google Scholar
  39. 39.
    Chen CL, 1970 Constituents of Quercus alba. Phytochemistry 9: 1149CrossRefGoogle Scholar
  40. 40.
    Cordell GA, Chang PTO, Fong HHS, Farnsworth NR,1977 Xylosmacin, a new phenolic glucoside ester from Xylosma velutina. Lloydia 40: 340–343Google Scholar
  41. 41.
    Correa D de B, Gottlieb OR, de Padua AP, 1975 Dihydrocinnamic acids from Hortia badinii. Phytochemistry 14: 2059–2060Google Scholar
  42. 42.
    Correa D de B, Gottlieb OR, de Padua AP, 1979 Dihydrocinnamyl alcohols from Hortia badinii. Phytochemistry 18: 351Google Scholar
  43. 43.
    Crombie L, 1955 Structure and stereochemistry of neoherculin. J Chem Soc 995–998Google Scholar
  44. 44.
    De Diaz AMP, Gottlieb OR, Magalhaes AF, Magalhaes EG, Maia JGS, Santos CC, 1977 The chemistry of Brazilian Lauraceae. XLVI. Notes on Aniba species. Acta Amazonica 7: 41–43Google Scholar
  45. 45.
    De Silva LB, Hearth WHMW, Jennings RC, Mahendran M, Wannigama GP, 1982 Isolation of specioside from Stereospermum personatum. Indian J Chem 21B: 703–704Google Scholar
  46. 46.
    Deshpande VH, Srinivasan R, Rama Rao AV, 1975 Phenolics of the heartwood of five Morus species. Ind J Chem 13: 453–457Google Scholar
  47. 47.
    Dutta P, 1942 Constituents of natural coumarins of Toddalia aculeata. J Indian Chem Soc 19: 425–428Google Scholar
  48. 48.
    Ekman R, 1976 Analysis of lignans in Norway spruce by combined gas chromatography-mass spectrometry. Holzforschung 30: 79–85CrossRefGoogle Scholar
  49. 49.
    Enquiquez RG, Chavez MA, Jauregui F, 1980 Propenylbenzenes from Guatteria gaumeri. Phytochemistry 19: 2024–2025CrossRefGoogle Scholar
  50. 50.
    Erdtman H, Harmatha J, 1979 Phenolic and terpenoid heartwood constituents of Libocedrus yateensis. Phytochemistry 18: 1495–1500CrossRefGoogle Scholar
  51. 51.
    Erickson RL, Pearl IA, Darling SF, 1970 Populoside and grandidentoside from the bark of Populus grandidentata. Phytochemistry 9: 857–863CrossRefGoogle Scholar
  52. 52.
    Eshiett IT, Taylor DAH, 1968 The isolation and structure elucidation of some derivatives of dimethyl-allyl-coumarin, chromone, quinoline, and phenol from Fagara species, and from Cedrelopsis grevei. J Chem Soc (C) 481–484Google Scholar
  53. 53.
    Estes TK, Pearl IA, 1967 Hot-water extractives of the green bark of Populus trichocarpa. Tappi 50: 318–323Google Scholar
  54. 54.
    Ewing J, Hughes GK, Ritchie E, 1950 The chemical constituents of Australian Zanthoxylum species. I. Suberosin, 6-(3,3-dimethylallyl)-7-methoxycoumarin. Aust J Sci Res 3A: 342–345Google Scholar
  55. 55.
    Fernandes JB, Gottlieb OR, 1976 Neolignans from Aniba species. Phytochemistry 15: 1033–1036CrossRefGoogle Scholar
  56. 56.
    Franca NC, Gottlieb OR, Magalhaes MT, Mendes PH, Maia JGS, Da Silva ML, Gottlieb Hem, 1976 Tri-O-methylgalangin from Aniba riparia. Phytochemistry 15: 572–573CrossRefGoogle Scholar
  57. 57.
    Franca NC, Gottlieb OR, Rosa BP, 1975 Juruenolide: A y-lactone from Iryanthera juruensis. Phytochemistry 14: 590–591Google Scholar
  58. 58.
    Franca NC, Gottlieb OR, Suarez AMP, 1973 6-Phenylethyl-5,6-dihydro-2-pyrones from Aniba gigantifolia. Phytochemistry 12: 1182–1184Google Scholar
  59. 59.
    Freudenberg K, Harkin JM, 1963 The glycosides of cambial sap of spruce. Phytochemistry 2: 189–193CrossRefGoogle Scholar
  60. 60.
    Fujii S, Aoki H, Komoto M, Munakata K, 1971 Fluorescent glycosides accumulated in Taphrina wiesneri-infected cherry stems. Agric Biol Chem 35: 1526–1541CrossRefGoogle Scholar
  61. 61.
    Giesbrecht AM, Franca NC, Gottlieb OR, 1974 The neolignans of Licaria canella. Phytochemistry 13: 2285–2293CrossRefGoogle Scholar
  62. 62.
    Goldschmid O, Hergert HL 1961 Examination of Western hemlock for lignin precursors. Tappi 44: 858–870Google Scholar
  63. 63.
    Gottlieb OR, Da Silva ML, Maia JG, 1972 Distribution of coumarins in Amazonian Brosimum species. Phytochemistry 11: 3479–3480Google Scholar
  64. 64.
    Gottlieb OR, Magalhaes MT, 1958 Isolation of piperonylic acid from Ocotea pretiosa. Nature 182: 742–743CrossRefGoogle Scholar
  65. 65.
    Gottlieb OR, Magalhaes MT, 1959 Occurrence of 1 -nitro-2-phenylethane in Ocotea pretiosa and Aniba canelilla. J Org Chem 24: 2070–2071CrossRefGoogle Scholar
  66. 66.
    Gottlieb OR, Mors WB, 1959 Isolation of 5, 6-dehydrokavain and 4-methoxyparacotoin from Aniba firmula Mez. J Org Chem 24: 17–18CrossRefGoogle Scholar
  67. 67.
    Govindachari TR, Pai BR, Subramaniam PS, Ramdas Rao U, Muthukumaraswamy N, 1967 Ferruol A, a new 4-alkylcoumarin. Tetrahedron 23: 4161–4165CrossRefGoogle Scholar
  68. 68.
    Gray AI, 1983 Structural diversity and distribution of coumarins and chromones in the Rutales. Phytochem Soc Eur Ser 22: 97–146Google Scholar
  69. 69.
    Gray AI, Waterman PG, 1978 Coumarins in the Rutaceae. Phytochemistry 17: 845–864CrossRefGoogle Scholar
  70. 70.
    Gujaral VK, Gupta SR, Verma KS, 1979 A new chromone glucoside from Tecomella undulata. Phytochemistry 18: 181–182CrossRefGoogle Scholar
  71. 71.
    Harborne JB, 1964 Biochemistry of phenolic compounds. Academic Press London, 618 ppGoogle Scholar
  72. 72.
    Harborne JB, Simmonds NW, 1974 The natural distribution of the phenolic aglycones. In: Harborne J B (ed) Biochemistry of phenolic compounds. Academic Press New YorkGoogle Scholar
  73. 73.
    Harmatha J, Lubke H, Rybarik I, Mahdalik M, 1978 cis-Coniferyl alcohol and its glucoside from the bark of beech ( Fagus silvatica L. ). Collect Czech Chem Commun 43: 774–780Google Scholar
  74. 74.
    Hasegawa M, Miyoshi T, 1960 Minor elements contained in the wood of Fagaria ailanthoides. J Jap For Soc 42: 222–223Google Scholar
  75. 75.
    Hashimoto K, Nakahara S, Inoue T, Sumida Y, Takahashi M, Masada Y, 1985 A new chromone from agarwood and pyrolysis products of chromone derivatives. Chem Pharm Bull 33: 5088–5091CrossRefGoogle Scholar
  76. 76.
    Hegarty M P, Lahey FN, 1956 The coumarins of Halfordia scleroxyla. Aust J Chem 9: 120–131CrossRefGoogle Scholar
  77. 77.
    Hegnauer R, 1960–1973 Chemotaxonomie der Pflanzen, Vol I-VI. Birkhauser BaselGoogle Scholar
  78. 78.
    Hergert HL, 1960 Chemical composition of tannins and polyphenols from conifer wood and bark. Forest Prod J 10: 610–617Google Scholar
  79. 79.
    Herrmann K, 1978 Hydroxyzimtsäure und Hydroxybenzoesäuren enthaltende Naturstoffe in Pflanzen. Fortsch Chem Org Naturst 35: 73–132CrossRefGoogle Scholar
  80. 80.
    Hillis WE, Inoue T, 1968 The polyphenols formed in Pinus radiata after Sirex attack. Phytochemistry 7: 13–22CrossRefGoogle Scholar
  81. 81.
    Hollis AF, Prager RH, Ritchie E, Taylor WC, 1961 The constituents Flindersia pubescens Bail, and F. schottiana F. Muell. Aust J Chem 14: 100–105Google Scholar
  82. 82.
    Inoue T, Ishidate Y, Fujita M, Kubo M, Fukushima M, Nagai M, 1978 Constituents in the leaves and the stem bark of Acer nikoense Maxim. Yakugaku Zasshi 98: 41–46PubMedGoogle Scholar
  83. 83.
    Inouye H, Okuda T, Hayashi T, 1971 Naphtochinonderivate aus Catalpa ovata G. Don. Tetrahedron Lett 39: 3615–3618Google Scholar
  84. 84.
    Inouye H, Okuda T, Hirata Y, Nagakura N, Yoshizaki M, 1967 Structure of catalpalactone, a new phthalide from catalpa wood. Chem Pharm Bull 15: 786–792CrossRefGoogle Scholar
  85. 85.
    Ishii H, Hosoya K, 1972 Arnottianin: A new dihydropyranocoumarin. Chem Pharm Bull 20: 860Google Scholar
  86. 86.
    Ishii H, Ishikawa T, Sekiguchi H, Hosoya K, 1973 Xanthoarnol. New dihydrofuranocoumarin. Chem Pharm Bull 21: 2346–2348Google Scholar
  87. 87.
    Joshi KC, Prakash L, Singh LB, 1975 6-O-Veratryl catalposide, a new iridoid glucoside from Tecomella undulata. Phytochemistry 14: 1441–1442Google Scholar
  88. 88.
    Joshi KC, Sharma AK, Singh P, 1986 A new ferulic ester from Tecomella undulata. Planta Med 71–72Google Scholar
  89. 89.
    Karrer W 1958 Konstitution und Vorkommen von organischen Pflanzenstoffen. Birkhäuser Basel, 1207 ppGoogle Scholar
  90. 90.
    Karrer W, Cherbuliez E, Eugster CH, 1977 Konstitution und Vorkommen von organischen Pflanzenstoffen. Ergänzungsband 1. Birkhäuser Basel, 1308 ppGoogle Scholar
  91. 91.
    Karrer W, Hürlimann H, Cherbuliez E, 1981 Konstitution und Vorkommen von organischen Pflanzenstoffen. Ergänzungsband 2. Birkhäuser Basel, 939 ppGoogle Scholar
  92. 92.
    Kijjoa A, Giesbrecht AM, Gottlieb OR, Gottlieb HE, 1981 1,3-Diaryl-propanes and propan- 2-ols from Virola species. Phytochemistry 20: 1385–1388Google Scholar
  93. 93.
    Kim Ki-U 1942 J Pharm Soc Japan 62: 455Google Scholar
  94. 94.
    Kimland B, Norin T, 1972 Wood extractives of common spruce, Picea abies ( L.) Karst. Svensk Papperstidn 10: 403–409Google Scholar
  95. 95.
    King FE, Housley JR, King TJ, 1954 Coumarin constituents of Fagara macrophylla, Zanthox- ylum flavum, and Chloroxylon swietenia. J Chem Soc 1392–1399Google Scholar
  96. 96.
    Klimczak M, Kahl W, Grodzinska-Zachwieja Z, 1972 Phenolic acids in poplar Populus. Diss Pharm Pharmacol 24: 181–185Google Scholar
  97. 97.
    Kohlbrenner PJ, Schverch C, 1959 Benzene-alcohol-soluble extractives of Sitka spruce. J Org Chem 24: 166–172CrossRefGoogle Scholar
  98. 98.
    Kritchevsky G, Anderson AB, 1955 The cone solid of coast redwood (Sequoia sempervirens) and giant sequoia ( Sequoia gigantea ). J Org Chem 20: 1402–1406Google Scholar
  99. 99.
    Kubo I, Matsumoto T, Klocke JA, Kamikawa T, 1984 Molluscicidal and insecticidal activities of isobutylamides isolated from Fagara macrophylla. Experientia 40: 340–341CrossRefGoogle Scholar
  100. 100.
    Lahey FN, MacLeod JK, 1968 Halfordin and isohalfordin - revised structures. Tetrahedron Lett 4: 447–451CrossRefGoogle Scholar
  101. 101.
    Lahey FN, Wluka DJ, 1955 Geijerin, a new coumarin from the bark of Geijera salicifolia. Aust J Chem 8: 125–128Google Scholar
  102. 102.
    Lundgren LN, Popoff T, Theander O, 1982 Acrylglycerol glucosides from Pinus sylvestris. Acta Chem Scand B36: 695–699CrossRefGoogle Scholar
  103. 103.
    Majumder PL, Sengupta GC, Dinda BN, Chatterjee A, 1974 Edgeworthin, a new biscoumarin from Edgeworthia gardneri. Phytochemistry 13: 1929–1931CrossRefGoogle Scholar
  104. 104.
    Marcano DDC, Hasegawa M, Castaldi A, 1972 Neutral compounds and alkaloides of Zantox- ylum ocumarense. Phytochemistry 11: 1531–1532CrossRefGoogle Scholar
  105. 105.
    Miki K, Sasaya T, 1979 Glycerol derivatives in the inner bark of Larix leptolepis Gord. Mokuzai Gakkaishi 25: 361–366Google Scholar
  106. 106.
    Moir M, Thomson RH, 1973 A new cinnamaldehyde from Patagonula americana. Phytochemistry 12: 2501–2503CrossRefGoogle Scholar
  107. 107.
    Moir M, Thomson RH, 1973 Cordiachromes from Patagonula americana L. J Chem Soc Perkin Trans I 1556–1561Google Scholar
  108. 108.
    Mondon A, Callsen H, 1975 Chromone und Cumarine aus Cneorum pulverulentum. Chem Ber 108: 2005–2020CrossRefGoogle Scholar
  109. 109.
    Mors WB, Gottlieb OR, Djerassi C, 1957 The chemistry of rosewood. Isolation and structure of anibine and 4-methoxyparacotoin. J Am Chem Soc 79: 4507–4511CrossRefGoogle Scholar
  110. 110.
    Mosihuzzaman M, Hoque MF, Chowdhury TA, Theander O, Lundgren LN, 1988 Phenolic acids in fresh and wretted jute plants ( Corchorus capsularis and Corchorus olitorius ). J Sci Food Agrie 42: 141–147Google Scholar
  111. 111.
    Mujumdar RB, Rama Rao AV, Rathi SS, Venkataraman K, 1975 Swietenone, the first natural t-butyl ketone, from Chloroxylon swietenia. Tetrahedron Lett 11: 867–868CrossRefGoogle Scholar
  112. 112.
    Mujumdar RB, Rathi SS, Rama Rao AV, 1977 Heartwood constituents of Chloroxylon swietenia D C. Indian J Chem 15B: 200Google Scholar
  113. 113.
    Murray RDH, 1978 Naturally occurring plant coumarins. Fortschr Chem Org Naturst 35: 199–429CrossRefGoogle Scholar
  114. 114.
    Nagarajan GR, Parmar VS, 1977 Phloroacetophenone derivatives in Prunus domestica. Phytochemistry 16: 614–615CrossRefGoogle Scholar
  115. 115.
    Nagarajan GR, Rani U, Parmar VS, 1983 Floribin — a new coumarin from Fraxinus floribunda Wall. Pharmazie 38: 72–73Google Scholar
  116. 116.
    Nagasampagi BA, Sriraman MC, Yankov L, Dev S, 1975 Siderin from Cedrela toona. Phyto- chemistry 14: 1673Google Scholar
  117. 117.
    Nair G V, Rudloff E v, 1959 The chemical composition of the heartwood extractives of tamarack (Larix laricina K. Koch ). Can J Chem 37: 1608–1613Google Scholar
  118. 118.
    Neish A, C 1957 Pungenin: A glucoside found in leaves of Picea pungens ( Colorado spruce ). Can J Biochem Physiol 35: 161–167Google Scholar
  119. 119.
    Norin T, Sundin S, Theander O, 1971 Dehydropinifolic acid, a diterpene acid from the needles of Pinus sylvestris L. Acta Chem Scand 25: 607–610CrossRefGoogle Scholar
  120. 120.
    Okorie DA, 1976 A new phthalide and xanthones from Anthocleista djalonensis and A. vogelli. Phytochemistry 15: 1799–1800CrossRefGoogle Scholar
  121. 121.
    Oksanen H, 1960 Paper chromatography of phenolic constituents in the bark of pine. Suom Kemistil 34B: 91–92Google Scholar
  122. 122.
    Oliveira AB de, Fonseca e Silva LG, Gottlieb OR, 1972 Flavanoids and coumarins from Platymiscium praecox. Phytochemistry 11: 3515–3519Google Scholar
  123. 123.
    Palo TR, 1984 Distribution of birch, willow, and poplar secondary metabolites and their potential role as chemical defense against herbivores. J Chem Ecol 10: 499–520CrossRefGoogle Scholar
  124. 124.
    Pearl IA, 1969 Water extractives of American Populus pulpwood species bark — a review. Tappi 52: 428–431Google Scholar
  125. 125.
    Pearl IA, Darling SF, 1959 Salireposide from the bark of Populus tremuloides. J Org Chem 24: 1616CrossRefGoogle Scholar
  126. 126.
    Pearl IA, Darling SF, 1962 Grandidentatin, a new glucoside from the bark of Populus grandidentata. J Org Chem 27: 1806–1809CrossRefGoogle Scholar
  127. 127.
    Pearl IA, Darling SF 1968 Continued studies on the hot water extractives of Populus balsamifera bark. Phytochemistry 7: 1851–1853CrossRefGoogle Scholar
  128. 128.
    Pearl IA, Darling SF 1970 Phenolic extractives of Salix purpurea bark. Phytochemistry 9: 1277–1281CrossRefGoogle Scholar
  129. 129.
    Pearl IA, Darling SF 1970 The structure of salicortin and tremulacin. Tetrahedron Lett 44: 3827–3830CrossRefGoogle Scholar
  130. 130.
    Pearl IA, Darling SF 1971 Studies of the hot water extractives of the bark and leaves of Populus deltoides Bartr. Can J Chem 49: 49–55CrossRefGoogle Scholar
  131. 131.
    Pickles SS 1912 The essential oil of the “Nepal sassafras” or “Nepal camphor” tree. J Chem Soc 101: 1433–1443CrossRefGoogle Scholar
  132. 132.
    Pilo C, Runeberg J 1960 Heartwood constituents of Juniperus chinensis. Acta Chem Scand 14: 353–358CrossRefGoogle Scholar
  133. 133.
    Popoff T, Theander O, Johansson M 1975 Changes in sapwood of roots of Norway spruce, attacked by Fomes annosus. Physiol Plant 34: 347–356CrossRefGoogle Scholar
  134. 134.
    Power F B, Moore C W 1909 The constituents of the bark of Prunus serótina. Isolation of 1-mandelonitrile glucoside. J Chem Soc 95: 243–261CrossRefGoogle Scholar
  135. 135.
    Rama Rao A V, Bhide K S, Mujumdar R B 1980 Isolation of swietenocoumarins G, H and I. Indian J Chem 19B: 1046–1048Google Scholar
  136. 136.
    Ramaiah P A, Row L R, Reddy D S, Anjaneyulu A S R, Ward R S, Pelter A 1979 Isolation and characterization of bergenin derivatives from Macaranga peltata. J Chem Soc Perkin Trans I: 2313–2316Google Scholar
  137. 137.
    Reher G, Kraus L, Sinnwell V, König W A 1983 A neoflavanoid from Coutarea hexandra ( Rubiaceae ). Phytochemistry 22: 1524–1525Google Scholar
  138. 138.
    Ritchie E 1964 Chemistry of Flindersia species. Rev Pure Appl Chem 14: 47–57Google Scholar
  139. 139.
    Ritchie E, Taylor W C, Vautin T K 1965 Chemical studies of the Proteaceae. I: Grevillea robusta A. Cunn and Orites excelsa R. Br. Aust J Chem 18: 2015–2020Google Scholar
  140. 140.
    Rosendal Jensen S, Juhl Nielsen B 1976 A new coumarin, fraxidin 8-O-β-D-glucoside and 10-hydroxy-ligstroside from bark of Fraxinus excelsior. Phytochemistry 15: 221–223CrossRefGoogle Scholar
  141. 141.
    Rowe J W, Conner AH 1979 Extractives in eastern hardwoods. USDA For Serv Gen Tech Rep FPL-18, 67 ppGoogle Scholar
  142. 142.
    Rudioff E v 1965 Guaiacylglycerol and quinol in the heartwood of Pinus resinosa Ait. Chem Ind 4: 180–181Google Scholar
  143. 143.
    Saengchantara S T, Wallace T W 1986 Chromanols, chromanones and chromones. Nat Prod Rep 465–475Google Scholar
  144. 144.
    Sainty D, Delaveau P, Bailleul F, Moretti C 1982 New iridoid from Randia formosa: 10-caffeoyl- deacetyldaphylloside. J Nat Prod 45: 486–488CrossRefGoogle Scholar
  145. 145.
    Sano Y, Sakakibara A 1978 Studies on chemical components of akaezomatsu (Picea glehnii) bark. 3. Isolation of two glycosides of β-hydroxyphenylglycerol. Hokkaido Daigaku Nogakubu Enshurin Kenkyu Hokoku 35: 157–163Google Scholar
  146. 146.
    Santamour F S Jr, Vettel H E 1978 The distribution of rhododendrin in birch ( Betula) species. Biochem Syst Ecol 6: 107–108Google Scholar
  147. 147.
    Savidge R A 1987 Dihydroconiferyl alcohol in developing xylem of Pinus contorta. Phytochemistry 26: 93–94CrossRefGoogle Scholar
  148. 148.
    Sato A, Senda M, Kakutani T, Watanabe Y, Kiato K 1966 Extractives from heartwood of Metasequoia glyptostroboides. Mokuzai Kenkya 39: 13–21Google Scholar
  149. 149.
    Schulte K E, Ruecker G, Klewe U 1973 Some constituents of the bark of Cedrelopsis grevei. Arch Pharm 306: 857–865CrossRefGoogle Scholar
  150. 150.
    Secor J B, Conn J E, Dunn J E, Seigler D S 1976 Detection and identification of cyanogenic glucosides in six species of Acacia. Phytochemistry 15: 1703–1706CrossRefGoogle Scholar
  151. 151.
    Seigler D S 1975 Isolation and characterization of naturally occurring cyanogenic compounds. Phytochemistry 14: 9–29CrossRefGoogle Scholar
  152. 152.
    Seikel M K, Hostettler F D, Niemann G J 1971 Phenolics of Quercus rubra wood. Phytochemistry 10: 2249–2251CrossRefGoogle Scholar
  153. 153.
    Senter P, Zavarin E, Zedier P H 1975 Volatile constituents of Cupressus stephensonii heartwood. Phytochemistry 14: 2233–2235CrossRefGoogle Scholar
  154. 154.
    Shen Z, Theander O 1985 Flavonoid glycosides from needles of Pinus massoniana. Phytochemistry 24: 155–158CrossRefGoogle Scholar
  155. 155.
    Shimomura H, Sashida Y, Adachi T 1987 Phenolic glucosides from Prunus gray ana. Phytochemistry 26: 249–251CrossRefGoogle Scholar
  156. 156.
    Shimomura H, Sashida Y, Adachi T 1988 Phenylpropanoid glucose esters from Prunus burgeriana. Phytochemistry 27: 641–644CrossRefGoogle Scholar
  157. 157.
    Shimomura H, Sashida Y, Oohara M, Tenma H 1988 Phenolic glucosides from Parabenzoin praecox. Phytochemistry 27: 644–646CrossRefGoogle Scholar
  158. 158.
    Singh H, Chawla A S, Kapoor V K, Kumar N, Piatak D M, Nowicki W 1981 Chemical constituents of Erythrina stricta bark. J Nat Prod 44: 526–529CrossRefGoogle Scholar
  159. 159.
    Sosa A, Sosa-Boudouil C 1936 Variations dans la composition du Boulean ( Betula alba L.) au cours de la végétation d’une année. Bull Soc Chim Biol 18: 918Google Scholar
  160. 160.
    Späth E, Jerzmanowska-Sienkiewiczowa Z 1937 Über Fraxidin und Isofraxidin. Ber Deutsch Chem Ges 1019–1020Google Scholar
  161. 161.
    Späth E, Jerzmanowska-Sienkiewiczowa Z 1937 Über Fraxinol, einen neuen Inhaltsstoff der Eschenrinde. Ber Deutsch Chem Ges 698–702Google Scholar
  162. 162.
    Steel J W, Weitzel P F, Audette R C S 1972 Investigation of the bark of Salix peteolaris. J Chromatogr 71: 435–441CrossRefGoogle Scholar
  163. 163.
    Stevens K L, Jurd L, Manners G 1973 Alliodorin, a phenolic terpenoid from Cordia alliodora. Tetrahedron Lett 31: 2955–2958CrossRefGoogle Scholar
  164. 164.
    Subba Rao GSR, Raj K, Kumar V P S 1981 Chemical examination of Clausena willdenovii W & A: Isolation of 3-(1,1-dimethylallyl)xanthyletin from the root and bark. Indian J Chem 20B: 88–89Google Scholar
  165. 165.
    Talapatra S K, Ganguly N C, Goswami S, Talapatra B 1983 Chemical constituents of Casearia graveolens: some novel reactions and the preferred molecular conformation of the major coumarin, micromelin. J Nat Prod 46: 401–408CrossRefGoogle Scholar
  166. 166.
    Tanaka H, Kato I, Ichino K, Ito K 1986 Coumarinolignoids, cleomiscosin A and cleomiscosin B from Aesculus turbinata. J Nat Prod 49: 366CrossRefGoogle Scholar
  167. 167.
    Theander O 1982 Hydrophilic extractives from the needles of Scots pine and Norway spruce. Svensk Papperstidn 9: R64–R68Google Scholar
  168. 168.
    Thieme H 1963 Isolierung eines neuen Phenolglycosids aus Salix triandra L. Die Naturwissenschaften 50: 571CrossRefGoogle Scholar
  169. 169.
    Thieme H 1964 Zur Konstitution des Salidrosides, eines Phenolglycosids aus Salix triandra L. Die Naturwissenschaften 51: 360CrossRefGoogle Scholar
  170. 170.
    Thieme H 1965a Die Phenolglycoside der Salicaceen: Untersuchungen über jahrzeitlich bedingte Veränderungen der Glycosidkonzentrationen, über die Abhängigkeit des Glycosidgehalts von der Tageszeit und von alten Pflanzenorganen. Pharmazie 20: 688–691PubMedGoogle Scholar
  171. 171.
    Thieme H 1965b Die Phenolglycosidspectren und der Glycosidgehalt der mitteldeutschen Salixarten. Pharmazie 20: 570–574PubMedGoogle Scholar
  172. 172.
    Tillekeratne L M V, Jayamanne D T, Weerasuria K D V, Gunatilaka AAL 1982 Lignans of Horsfieldia iryaghedhi. Phytochemistry 21: 476–478CrossRefGoogle Scholar
  173. 173.
    Tsukamoto H, Hisada S, Nishibe S, Roux D G, Rourke J P 1984 Coumarins from Olea africana and Olea capensis. Phytochemistry 23: 699–700CrossRefGoogle Scholar
  174. 174.
    Tyman JHP 1979 Non-isoprenoid long-chain phenols. Chem Soc Rev 8: 499–537CrossRefGoogle Scholar
  175. 175.
    Viera P C, Yoshida M, Gottlieb O R, Filho H F P, Nagern T J, Braz Filho R 1983 Lactones from Iryanthera species. Phytochemistry 22: 711–713CrossRefGoogle Scholar
  176. 176.
    Vrkoc J, Sedmera P 1972 Extractives of Chloroxylon swietenia. Phytochemistry 11: 2647–2648CrossRefGoogle Scholar
  177. 177.
    Waterman P G 1976a 2,4,5-Trimethoxystyrene from Pachypodanthium standtii. Phytochemistry 15: 347Google Scholar
  178. 178.
    Waterman P G 1976b Alkaloids and coumarins from Zanthoxylum flavum. Phytochemistry 15: 578–579CrossRefGoogle Scholar
  179. 179.
    Zavarin E, Anderson A B 1955 Extractive components from incence-cedar heartwood (Libocedrus decurrens Torrey). I. Occurrence of carvacrol, hydrothymoquinone and thymoquinone. J Org Chem 20: 82–88Google Scholar
  180. 180.
    Zoghbi M D G B, Roque N F, Gottlieb O R 1981 Propacin, a coumarinolignoid from Protium opacum. Phytochemistry 20: 180CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1989

Authors and Affiliations

  • O. Theander
  • L. N. Lundgren

There are no affiliations available

Personalised recommendations