Enantiomers of sesquiterpene and diterpene hydrocarbons in Araucaria species

Phytochemical Analysis

Volumn 11, Issue 2, 2000, Pages 99-105

  Pietsch, Martin ^a   König, Wilfried A ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

Author keywords

A. bidwillii; A. heterophylla; Araucaria araucana; Cyclodextrin derivatives; Diterpenes; Enantioselective gas chromatography; Sesquiterpenes; Stereochemical analysis

Indexed keywords

CYCLODEXTRINS; ENANTIOSELECTIVITY; GAS CHROMATOGRAPHY; GAS OILS; GASES; OLEFINS;

A BIDWILLII; A HETEROPHYLLA; ARAUCARIA ARAUCANA; CYCLODEXTRIN DERIVATIVES; DITERPENE HYDROCARBONS; DITERPENES; ENANTIOSELECTIVE GAS CHROMATOGRAPHY; SESQUITERPENE HYDROCARBONS; SESQUITERPENES; STEREOCHEMICAL ANALYSIS;

ENANTIOMERS;

CYCLODEXTRIN DERIVATIVE; DITERPENE; HYDROCARBON; SCLAREOL; SESQUITERPENE; VEGETABLE OIL;

ARTICLE; CAPILLARY GAS CHROMATOGRAPHY; ENANTIOMER; GAS CHROMATOGRAPHY; STEREOCHEMISTRY;

ARAUCARIA; ARAUCARIA ARAUCANA; ARAUCARIA BIDWILLII; ARAUCARIA HETEROPHYLLA;

EID: 1642633607     PISSN: 09580344     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1565(200003/04)11:2<99::AID-PCA494>3.0.CO;2-9     Document Type: Article

References (32)

1. Almqvist, S. O., Enzell, C. R. and Wehrli, F. W. (1975). Carbon-13 NMR Studies of labdane diterpenoids. Acta Chem. Scand. B29, 695-702.
2. 13C-NMR spectroscopy of natural substances. Org. Magn. Res. 12, 429-431.
3. Bevan, C. W. L., Ekong, D. E. U. and Okogun, J. I. (1968). West African timbers. Part XXII. The diterpenes of Oxystigma oxyphyllum Harms. J. Chem. Soc. C, 1067-1070.
4. Briggs, L. H. and White, G. W. (1975). Constituents of the essential oil of Araucaria araucana. Tetrahedron 31, 1311-1314.
5. Bruns, K., (1968). Diterpene V, Über die C13-Konfiguration der Diterpene aus Araucaria imbricata, Pavon (Araucariaceae). Tetrahedron 24, 3417-3423.
6. Bruns, K. and Weissmann, G. (1966). Die Konfiguration der Diterpene aus Araucaria imbricata, Pavon (A. araucana). Tetrahedron Lett. 17, 1901-1903.
7. Bülow, N. and König, W. A. (1996). Essential Oils: Basic and Applied Research, Proceedings of the 27th International Symposiumon Essential Oils, Vienna, (Franz, Ch., Mathe, A. and Buchbauer, G., eds.), Allured Publishing Corporation, Coral Stream.
8. Caputo, R. and Mangoni, L. (1974). Diterpenes from Araucaria bidwilli. Phytochemistry 13, 467-470.
9. Caputo, R., Mangoni, L., Monaco, P. Pelosi, L. and Previtera, L. (1976a). Neutral diterpenes from Araucaria bidwillii. Phytochemistry 15, 1401-1402.
10. Caputo, R., Mangoni, L., Monaco, P. and Previtera, L. (1976b). XXXII / Diterpenoids of Araucariacea. VII. Minor diterpenes from the resin of Araucaria imbricata. Gazz. Chim. Ital. 106, 1119-1121.
11. Chandra, G., Clark, J., McLean, J., Pauson, P. L. Watson, J., Reed, R. I. and Tabrizi, F. M. (1964). New diterpenes from Araucaria imbricata. J. Chem. Soc. IV, 3648-3655.
12. De Santis, V. and Medina, J. D. (1981). Crystalline racemic labda-8(20),13-dien-15-oic acid in the trunk resin of Eperua Purpurea. J. Nat. Prod. 44, 370-372.
13. Dönnecke, J., Paul, C., König, W. A., Svensson, L. A., Gyllenhaal, O., and Vessman, J. (1996). Immobilisation of heptakis(6-O-tert.butyl-2,3-di-O-methyl)-β-cyclodextrin for capillary gas chromatography, supercritical fluid chromatography and micro-liquid chromatography. J. Microl. Sep: 8, 495-504.
14. Garbarino, J. A., Oyarzun, M. L. and Gambro, V. (1987). Labdane diterpenes from Araucaria araucana. J. Nat. Prod. 50, 935-936.
15. Garcia-Alvarez, M. C., Rodriguez, B., Valverde, S., Fraga, B. M. and Gonzalez, A. G. (1981). Carbon-13 NMR spectra of some ent-rosane diterpenoids. Phytochemistry 20, 167-169.
16. Golte, W. (1993). Erdgeschichtliche Forschung. Vol. 27. Franz Steiner, Stuttgart.
17. Grande, M., Moran, J. R., Macias, M. J. and Mancheno, B. (1993). Carbon-13 nuclear magnetic resonance spectra of some tetracyclic diterpenoids isolated from Elaeoselinum species. Phytochem. Anal. 4, 19-24.
18. Gupta, A. S. and Dev, S. (1963). Chromatography of organic compounds I. Thin-layer chromatography of olefins. J. Chromatogr. 12, 189-195.
19. Hardt, I. H. and König, W. A. (1994). Preparative enantiomer separation with modified cyclodextrins as chiral stationary phases. J. Chromatogr. A666, 611-615.
20. Hardt, I. H., Rieck, A., Fricke, C. and König, W. A. (1995). Enantiomeric composition of sesquiterpene hydrocarbons of the essential oil of Cedrela Odorata L. Flav. Fragr. J. 10, 165-171.
21. Huneck, S. and Klein, E. (1967). Inhaltsstoffe der Moose III. Über die vergleichende Gas- und Dünnschichtchromatographische Untersuchung der Ätherischen Öle einiger Lebermoose und die Isolierung von (-)-Longifolen und (-)-Longiborneol aus Scapania undulata (L.) Dum. Phytochemistry 6, 383-390.
22. Joulain, D. and König, W. A. (1998). The Atlas of Spectral Data of Sesquiterpene Hydrocarbons. E.B., Hamburg.
23. König, W. A., Gehrcke, B., Icheln, D., Evers, P., Dönnecke, J. and Wang, W. (1992). New selectively substituted cyclodextrins as stationary phase for the analysis of chiral constituents of essential oils. J. High Res. Chromatogr. 15, 367-372.
24. König, W. A., Rieck, A., Hardt, I., Gehrcke, B., Kubeczka, K.-H. and Muhle, H. (1994). Enantiomeric composition of the chiral constituents of essential oils - Part 2: Sesquiterpene hydrocarbons. High Res. Chromatogr. 17, 315-320.
25. Moulines, J., Lamidey, A.-M., Bats, J.-P. and Morisson, V. (1981). A short and efficient synthesis of (+)-13-epimanoyl oxide from sclareol. Synth. Comm. 23, 2991-2998.
26. Niwa, M., Igutchi, M. and Yamamura, S. (1980). Co-occurrence of (-)- and (+)-germacrene-D in Solidago altissima L: determination of the optical rotation of the optically pure germacrene-D. Chem. Pharm. Bull. 28, 997-999.
27. Noma, M., Suzuki, F., Gamu K. and Kawashima N. (1982). Two labdane diterpenoids from Nicotiana raimondii. Phytochemistry 21, 395-397.
28. Perry, N. B. and Weavers, R. T. (1985). Foliage diterpenes of Dacrydium intermedium: identification, variation and biosynthesis. Phytochemistry 24, 2899-2904.
29. Pietsch, M. and König, W. A. (1997). Enantiomeric composition of the chiral constituents of essential oils - Part 3: Diterpene hydrocarbons. J. High Res. Chromatogr. 20, 257-260.
30. Torrenegra, R., Robles, J., Waibel, R., Löwel, M. and Achenbach, H. (1994). Diterpenes and diterpene xylosides from Conyza trihecatactis. Phytochemistry 35, 195-199.
31. Weissmann, G. and Bruns, K. (1965). Terpene aus dem Harz von Araucaria imbricata, Pavon (A. Araucana). Naturwissenschaften 52, 185-186.
32. Weissmann, G., Bruns, K. and Grützmacher, H. F. (1965). Terpene aus dem Harz von Araucaria imbricata, Pavon (A. araucana). Tetrahedron Lett. 51, 4623-4626.