Studies on the Chemistry of Cedrus libani A. Rieh. I. Wood Extractives of Cedrus libani

Holzforschung

Volumn 41, Issue 1, 1987, Pages 27-38

  Haftzoğlu, Harzemşah ^a  

^a BLACK SEA TECHNICAL UNIVERSITY   (Turkey)

Author keywords

Cedrus libani; Fatty acids; Fatty alcohols; Phytosterols; Resin acids; Resin canals; Sesquiterpenes; Unsaponifiables; Wood extractives

Indexed keywords

EID: 0001810074     PISSN: 00183830     EISSN: 1437434X     Source Type: Journal    
DOI: 10.1515/hfsg.1987.41.1.27     Document Type: Article

References (95)

1. Adams, D.R., S.P. Bhatnagar and R.C. Cookson. 1975. Structure and synthesis of a new ketone from Cedrus species; some new constituents of Cedrus atlantica Manet. J. Chem. Soc. Perkin Trans. I (15), 1502-1506.
2. Adams, D.R., S.P. Bhatnagar, R.C. Cookson and R.M. Tud-denham. 1974. Structure and syntheses of a new ketone from the essential oil of Cedrus species. Tetrahedron Letters (44), 3903-3904.
3. Agrawal, P.K. Unpublished results. From ref.: Agrawal and Rastogi 1984.
4. Agrawal, P.K., S.K. Agarwal and R.P. Rastogi. 1980a. Dihydrof-lavonols from Cedrus deodara, Phytöchemistry 79, 893-896.
5. Agrawal, P.K., S.K. Agarwal and R.P. Rastogi. 1980b. A new neolignan and other phenolic constituents from Cedrus deodara. Phytöchemistry 19, 1260-1261.
6. Agrawal, P.K. and R.P. Rastogi. 1981. Terpenoids from Cedrus deodara. Phytöchemistry 20,1319-1321.
7. Agrawal, P.K. and R.P. Rastogi. 1982. Two lignans from Cedrus deodara. Phytöchemistry 21, 1459-1461.
8. Agrawal, P.K. and R.P. Rastogi. 1984. Chemistry of the true cedars. Biochem. Syst. Ecol. 12 (2), 133-144.
9. Agrawal, P.K. and R.P. Rastogi. Unpublished results. From ref.: Agrawal and Rastogi 1984.
10. Agrawal, P.K., R.P. Rastogi and B.-G. Osterdahl. 1983.13c NMR spectral analysis of dihydrobenzofuran lignans. Org. Magn. Reson. 21 (2), 119-121.
11. Assarsson, A. and G. Äkerlund. 1966. Studies on wood resin, expecially the change in chemical composition during seasoning of the wood. Part 4. The composition of the petroleum ether soluble nonvolatile extractives from fresh spruce, pine, birch and aspen wood. Svensk Papperstidn. 69 (16), 517-525.
12. Audier, H.E., S. Bory, M. Fétizon and N-T. Anh. 1966. Spectres de masse de terpenes. III. Influence des liaisons ethyleniques. sur la fragmentation des diterpönes. Bull. Soc. Chim. France (12), 4002-4010.
13. Bajaj, A.G., S. Dev, B. Tagle, J. Telser and J. Clardy. 1980. The, stereochemistry of allohimachalol, Tetrahedron Letters (21), 325-326.
14. Bardyshev, I.I. and A.N. Bulgakov. 1975. Khromatograficheskie metody analiza smolyanykh kislot. Khromatogr. Anal. Khim. Drev. 101-111.
15. Baumgarh, M. 1980. Neue pharmakologisch interessante Naturstoffe. Planta med. 39, 297.
16. Bisarya, S.C. and S. Dev. 1964. Allohimachalol, a new type in ses-quiterpenoids. Tetrahedron Letten (49), 3761 -3765.
17. Bisarya, S.C. and S. Dev. 1968a. Studies in sesquiterpenes -XXXIH. Himachalol. Tetrahedron 24, 3861-3867.
18. Bisarya, S.C. andS. Dev. 1968b. Studiesinsesquiterpenes-XXXIV. Structureof allohimachalol.Tetrahedron 24,3869-3879.
19. Brasch, D.J. and J.K.N. Jones. 1959. Investigation of some ancient woods. Tappi 42 (11), 913-920.
20. Bredenberg, J.B-son and H. Erdtman. 1961. Sesquiterpenes from Cedrus species. Acta Chem. Scand. 15 (3), 685-686.
21. Brooks, C.J.W., W. Henderson and G. Steel. 1973. The use of trimethylsilyl ethers in the characterization of natural sterols and steroid diols by gas chromatography - mass spectrometry. Biochim. Biophys. Acta 296, 431-445.
22. Brooks, C.J.W., H.C. Horning and J.S. Joung. 1968. Characterization of sterols by gas chromatography - mass spectrometry of the trimethyl silyl ethers. Lipids 3 (5), 391-402.
23. Browning, B.L. 1967. Methods of Wood Chemistry. Vol. 1, pp. 152-153. Interscience Publ. London, New York.
24. Bruun, H.H. and S. Gäsland. 1960. Fördelningkromatografiska studier av hartssyrasammansättningen hos kädharts av nordisk tall och gran, finländsk tallhartssyra och katalytiskt modifierad tallhartssyra. Acta Acad. Abo. Math. Phys. 22,122 pp.
25. Challen, S.B. and M. KuCera. 1970. Resin acids of Pinaceae and Cupressaceae species. Drev. Vysk. (2): 69-74. (From: 1971. Chem. Abstr. 74, 55418).
26. Chandra, S., K. Sambasivarao, R. Prakash, V.J. Lai and M. Sabir. 1978. Indian Vet. J. 55, 963. From ref.: Agrawal and Rastogi 1984.
27. Charas, C., C. Ducauze and C. Rävolon. 1978. L'adaptation olfactive et Pallotrophie chez certains Scolytidae splcifiques des con-iferes. C.R. Hebd. Seances Acad. Sci. Ser. D287(4), 285-288.
28. Chopra, C.L., M.C. Bhatia and I.C. Chopra. 1960. In vitro an-tibacterial activity of oils from Indian medicinal plants I.J. Amer. Pharm. Ass. (Sci. Ed.) 49 (12), 780-781.
29. Chopra, I.C., K.L. Handa and A.B. Kar. 1959. Himalayan cedar-wood oil as a substitute for imported cedarwood oil in micro-scopical work. J. Sci. Industr. Res. 18 C (7), 133-134.
30. Crawford, R.J., W.F. Erman and C.D. Broaddus. 1972. Metalation of limonene. A novel method for the synthesis of bisabolane sesquiterpenes. J. Amer. Chem. Soc. 94 (12), 4298-4306.
31. Daunis, J., R. Jacquier, H. Lopez and Ph. Viallefont. 1981. A con-venient synthesis of ar-himachalene and some of its derivatives. J. Chem. Res. (S), 45.
32. Dhar, M.L., M.M. Dhar, B.N. Dhawan, B.N. Mehrotra and C. Ray. 1968. Indian J. Exp. Biol. 6, 232. From ref.: Agrawal and Rastogi 1984.
33. Dikshit, A. and S.N. Dixit. 1982. Cedrus oil - a promising antifungal agent. Indian Perfum. 26 (2-4), 216-227.
34. Edlin, H.L. 1963. A modern sylva or a discourse of forest trees. 7. Cedars - Cedrus species. Quart. J. For. 57 (4), 302-310.
35. Ekman, R. 1979a. Analysis of the nonvolatile extractives in Norway spruce sapwood and heartwood, Acta Acad. Abo. Ser. B 39 (4), 20 pp.
36. Ekman, R. 1979b. A scheme for routineanalysis of Norway spruce wood extractives. Acta Acad. Abo. Ser. B 39 (5), 8 pp.
37. Ekman, R. 1980. New polyenoic fatty acids in Norway spruce wood. Phytochemistry 29, 147-148.
38. Ekman, R. and G. Pensar. 1971. Studies on components in wood. 5. Mass spectrometric Identification of saturated long chain fatty acids in Norway spruce (Picea abies). Finska Kemists. Medd. 80 (3), 40-47.
39. Ekman, R. and G. Pensar. 1973a. Studies on components in wood. 6. Isolation and mass spectrometric identification of monoenoic fatty acids in Norway spruce (Picea abies). Finska Kemists. Medd. 82 (3), 48-59.
40. Ekman, R. and G. Pensar. 1973b. Studies on components in wood. 7. Identification of total fatty acids in birch (Betula verrucosa) by gas chromatography - mass spectrometry. Finska Kemists. Medd. 82 (4), 105-113.
41. Fahn, A., E. Werker and P. Ben-Tzur. 1979. Seasonal effects of wounding and growth substances on development of tramatic resin ducts in Cedrus libani. New Phytol. 82 (2), 537 -544.
42. Garg, S.C. and D.C. Garg. 1980. Perfum. Cosmet. 61, 219. From ref.: Agrawal and Rastogi 1984.
43. Grimal, E. 1902. C.R. 135,582,1057. From ref.: Agrawal and Rastogi 1984.
44. Gupta, R.K., S.K. Saksena, B. Dutt and V. Mahadevan. 1968. Indian J. Vet. Sci. 38,208. From ref.: Agrawal and Rastogi 1984.
45. Hafizoglu, H. 1979. Investigations on Turkish tall oil. Medd. Stift. Abo Akademi Forskningsinstitut (52), 175 pp.
46. Haftzoġlu, H. 1983. Wood extractives of Pinus sylvestris, L., Pinus nigra Am. and Pinus brutia Ten. with special reference to nonpolar components. Holzforschung 37 (6), 321-326.
47. Hergert, H.L. and O. Goldschmid. 1958. Biogenesis of heartwood and bark constituents. I. A new taxifolin glucoside. J. Org. Chem. 25,700-704.
48. Holmbom, B. 1977. Improved gas chromatographic analysis of fatty and resin acid mixtures with special reference to tall oil. J. Amer. Oil Chem. Soc. 54 (7), 289-293.
49. Holmbom, B. and E. Avela. 1971a. Studies on tall oil from pine and birch. 1. Composition of fatty and resin acids in sulfate soaps and in crude tall oils. Acta Acad. Abo. Ser. B 31 (13), 14 pp.
50. Holmbom, B. and E. Avela. 1971b. Studies on tall oil from pine and birch. II. Unsaponifiable constituents in sulfate soaps and in crude tall oils. Acta Acad. Abo. Ser. B 31 (16), 18 pp.
51. Holmbom, B., E. Avela and S. Pekkala. 1974. Capillary gas chromatography - mass spectrometry of resin acids in tall oil rosin. J. Amer. Oil Chem. Soc. 51 (9), 397-400.
52. Holmbom, B. and R. Ekman. 1978. Tall oil precursors of Scots pine and common spruce and their change during sulphate pulping. Acta Acad. Abo. Ser. B 38 (3), 11 pp.
53. Joseph, T.C. and S. Dev. 1961. Structure of himachalenes. Tetrahedron Letters, 216-222.
54. Joseph, T.C. and S. Dev. 1968a. Studies in sesquiterpenes - XXIX. Structure of himachalenes. Tetrahedron 24,3809-3827.
55. Joseph, T.C. and S. Dev. 1968b. Studies in sesquiterpenes -XXXI. The absolute stereochemistry of himachalenes. Tetrahedron 24,3841-3852.
56. Joseph, T.C. and S. Dev. 1968c. Studies in sesquiterpenes -XXXII. Structure of himachalene monohydrochloride and the preparation of fro/u-himachalenes. Tetrahedron 24, 3853 -3859.
57. Joye, N.M.Jr. and R.V. Lawrence. 1967. Resin acid composition of pine oleoresins. J. Chem. Eng. Data 12 (2), 279-282.
58. Kar, K., V.N. Puri, G.K. Patnaik, R.N. Sur, B.N. Dhawan, D.K. Kulshreshtha and R.P. Rastogi. 1975. Spasmolytic constituents of Cedrus deodara (Roxb.) Loud: Pharmacological evaluation of himachalol. J. Pharm. Sci. 64 (2), 258-262.
59. Kayacik, H. 1980. Orman ve Park Agaglannin Özel Sistematigi. I. Cilt. Gymnospermae (AçIk Tohumlular). Istanbul Üniversitesi Orman Fakültesi Yayinlan (2642/281) pp. 172-181. Istanbul.
60. Knights, B.A. 1967. Identification of plant sterols using combined GLC/mass spectrometry. J. Gas Chromatogr. 5 (6), 273-282.
61. Krishnappa, S. and S. Dev. 1978. Studies in sesquiterpenes - LVIII. Deodardione, a sesquiterpene diosphenol, and Iimonenecarboxylic acid, a possible norsesquiterpene - Compounds from the wood of Cedrus deodara Loud. Tetrahedron 34, 599-602.
62. Kulshreshtha, D.K. and R.P. Rastogi. 1975. Constitution of the sesquiterpenoid, centdarol. Phytochemistry 14, 2237-2240.
63. Kulshreshtha, D.K. and R.P. Rastogi. 1976. The Constitution of isocentdarol, a sesquiterpenediol from Cedrus deodara. Phytochemistry 75, 557-558.
64. Lai, J., K. Sambasivarao, S. Chandra, R.C. Naithani, S.K. Chat-topadhyay and M. Sabir. 1976. Indian Vet. J. 55,543. From ref.: Agrawal and Rastogi 1984.
65. Manzoor-i-Khuda, M. and M.A. Saleque. 1964. Constituents of Cedrus deodara (dear wood). Part I. Isolation of dewarene and dewarol. Pakistan J. Sci. Ind. Res. 6 (3), 201-203.
66. Massy, R. 1929. Utilization in medicine of oil and of liquid tar of Cedrus atlantica. Bull. Inst. Pin (56), 30-31. From: 1929. Chem. Abstr. 23,1993.
67. Morris, J. A., A. Khettry and E. W. Seitz. 1979. Soybeans and Inflation. J. Amer. Oil Chem. Soc. 56, 595-599.
68. Narayanamurti, D. and N.R. Das. 1955. Die Abhängigkeit der chemischen Zusammensetzung des Holzes einiger indischer Holzarten von seiner Lage innerhalb des Stammes. Holz RohWerkstoff 13 (2), 52-56.
69. Nilsson, B. 1969. X-ray analysis of himachalene monohydrochloride. Arkiv Kemi 29,415-426.
70. Norin, T. and B. Winell. 1971. Diterpenoids of cones from two Cedrus species. Phytochemistry 10, 2818-2821.
71. Ohta, Y. and Y. Hirose. 1967. The structure of cubenol and epi-cubenol. Tetrahedron Letters (22), 2073-2075.
72. Pande, B.S., S. Krishnappa, S.C. Bisarya and S. Dev. 1971. Studies in sesquiterpenes - XLVII. cis- and trans-Atlantones from Cedrus deodara Loud. Tetrahedron 27,841-844.
73. Pandey, R.C. and S. Dev. 1968. Studies in sesquiterpenes - XXX. Synthesis of ar-himachalene and himachalanes. Tetrahedron 24, 3829-3839.
74. Pfau, A.St. 1932. Über Sesquiterpen-Ketone. Helv. Chim. Acta 15,1481-1483.
75. Pfau, A.St., and PI. Plattner. 1934. Zur Kenntnis der flüchtigen Pflanzenstoffe I. Über Atlanton, den Riechstoff der echten Cedemholzöle. Helv. Chim. Acta 17,129-157.
76. Plattier, M. and P. Teisseire. 1972. Isolation and synthesis of Atlas cedar essence constituents. An. Acad. Bras. Cienc. 44 (Suppl.), 392-404. From: 1976. Chem. Abstr. 84,44390.
77. Plattier, M. and P. Teisseire. 1974. Recherches 19,167. From ref.: Agrawal and Rastogi 1984.
78. Puri, V.N., K. Kar, G.K. Patnaik, B.N. Dhawan, D.K. Kul-shreshtha and R.P. Rastogi. 1975. Spasmolytic constituents of Cedrus deodara Roxb. Loud. II. Isolation and evaluation of allohimachalol and 3 new sesquiterpene alcohols. Indian J. Exp. Biol. 13 (4), 369-370.
79. Rao, G.S.K., S. Dev and P.C. Guha. 1952. Sesquiterpenes. XII. Sesquiterpenes of the essential oil from the wood of the Himalayan Deodar. J. Indian Chem. Soc. 29, 721-730.
80. Roberts, O.D. 1916. The volatile oil from the wood of the Indian Deodar tree. J. Chem. Soc. 109,791-796.
81. Rol, R. 1964. A propos de –cfcdres— Rev. For. Frans. 16 (3), 183-187.
82. Sen-Sarma, P.K. 1963. Studies on the natural resistance of timbers to termite attack. III. Results of accelerated laboratory tests of 9 species of Indian woods against the Mediterranean dry wood termite (yellow necked dry wood termite), Kalotermes flavicol-lis Fabr. Holzforschung Holzverwertung 15, 51-56.
83. Shankaranarayan, R., S.C. Bisarya and S. Dev. 1977. Studies in sesquiterpenes - LIV. Oxidohimachalene, a novel sesquiter-penoid from the wood of Cedrus deodara Loud.fTetrahedron 33, 1207-1210.
84. Shankaranarayan, R., S. Krishnappa, S.C. Bisarya and S. Dev. 1973. Deodarone, a novel sesquiterpene tetrahydro-y-pyrone from Cedrus deodara essential oil. Tetrahedron Letters (6), 427-428.
85. Shankaranarayan, R., S. Krishnappa, S.C. Bisarya and S. Dev. 1977. Studies in sesquiterpenes - LIII. Deodarone and atlan-tolone, new sesquiterpenoids from the wood of Cedrus deodara Loud. Tetrahedron 33,1201-1205.
86. Shankaranarayan, R., S. Krishnappa and S. Dev. 1977. Studies in sesquiterpenes - LIL Isohimachalone: A constituent of the essential oil from wood of Cedrus deodara Loud. Tetrahedron 33, 885-886.
87. Silverstein, R.M., G.C. Bassler and T.C. Morrill. 1974. Spec-trometric Identification of Organic Compounds. John Wiley and Sons. pp. 21-23. New York, London.
88. Simonsen, J.L. and M.G. Rau. 1922. Indian For. Rec. 9,13. From ref.: Agrawal and Rastogi 1984.
89. Spiteller, G. 1966. Massenspektrometrische Strukturanalyse organischer Verbindungen. Verlag Chemie, GmbH. pp. 100-105. Weinheim.
90. Sydov, E.v., K. Anjou and G. Karlsson. 1970. Dicyclic sesquiterpenes. Arch. Mass Spectral Data 1,534-537.
91. Yildinm, H. and B. Holmbom. 1978a. Investigations on the wood extractives of pine species from Turkey. II. Composition of fatty and resin adds in Pinus silvestris and Pinus nigra. Acta Acad. Abo. Ser. B 57(4), 6 pp.
92. Yildinm, H. and B. Holmbom. 1978b. Investigations on the wood extractives of pine species from Turkey. III. Nonvolatile, nonpolar components in Pinus brutia Henry. Acta Acad. Abo. Ser. B 37 (5), 9 pp.
93. Zeman, A. and H. Scharmann. 1972. Massenspektrometrie von Lipiden (eine Zusammenfassung) I. Fette o Seifen * Anstrichmittel 74 (9), 509-519.
94. Zinkei, D.F. and C.C. Engler. 1977. Gas-liquid chromatography of resin acid esters. J. Chromatogr. 136,245-252.
95. Zinkei, D.F., L.C. Zank and M.F. Wesolowski. 1971. Diterpene resin acids - A compilation of infrared, mass, nuclear magnetic resonance, Ultraviolet spectra and gas chromatographic retention data. U.S.D. A. Forest Service, Forest Products Laboratory, Madison, Wis.