The nature and fate of natural resins in the geosphere - VIII. NMR and Py-GC-MS characterization of soluble labdanoid polymers, isolated from Holocene Class I resins

Organic Geochemistry

Volumn 27, Issue 7-8, 1997, Pages 449-464

  Clifford, David J ^a,b,d   Hatcher, Patrick G ^b   Botto, Robert E ^a   Muntean, John V ^a   Michels, Beverly ^c   Anderson, Ken B ^a  

^a ARGONNE NATIONAL LABORATORY   (United States)

^b PENNSYLVANIA STATE UNIVERSITY   (United States)

^c BP EXPLORATION   (United Kingdom)

^d ROYAL NETHERLANDS INSTITUTE FOR SEA RESEARCH   (Netherlands)

Author keywords

Amber; Labdanoid; Maturation; NMR; Py GC MS; Resinite; Structure

Indexed keywords

POLYLABDANOIDS;

ANALYTICAL GEOCHEMISTRY; CHLORINE COMPOUNDS; COMPOSITION; CROSSLINKING; MASS SPECTROMETRY; METHANOL; MOLECULAR STRUCTURE; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; PYROLYSIS; SOLVENT EXTRACTION;

ORGANIC POLYMERS;

EID: 0031581478     PISSN: 01466380     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0146-6380(97)00043-0     Document Type: Article

References (50)

1. van Aarssen, B. K. G. (1992) Structural assignment and catagenetic behaviour of macromolecular constituents of recent and fossil natural resins. PhD thesis, Technical University of Delft, The Netherlands.
2. van Aarssen B. K. G., de Leeuw J. W. Comment on "Extraction and methylation of Latrobe Valley resinites" by M. A. Wilson, P. A. Cole-Clarke, G. D. Willett and P. F. Greenwood, Org. Geochem. Vol. 18, pp. 555-565, 1992. Org. Geochem. 20:1993;105-106.
3. van Aarssen B. K. G., de Leeuw J. W. Comment on "Extraction and methylation of Latrobe Valley resinites" by M. A. Wilson, P. A. Cole-Clarke, G. D. Willett and P. F. Greenwood, Org. Geochem. Vol. 18, pp. 555-565, 1992. Org. Geochem. 20:1993;105-106.
4. Anderson K. B. The nature and fate of natural resins in the geosphere. IV. Middle and upper Cretaceous amber from the Taimyr Peninsula, Siberia - evidence for a new form of polylabdanoid resinite and revision of the classification of Class I resinites. Org. Geochem. 21:1994;209-212.
5. Anderson, K. B. (1995) The nature and fate of natural resins in the geosphere. V. New evidence concerning the structure, composition and maturation of Class I (polylabdanoid) resinites. In Amber, Resinite and Fossil Resins (Edited by Anderson, K. B. and Crelling, J. C.), pp. 105-129. ACS Symposium Series 617, ACS publications.
6. 14C) age scale for description of immature natural resins. An invitation to scientific debate. Org. Geochem. 25:1996;251-253.
7. Anderson K. B., Botto R. E. The nature and fate of natural resins in the geosphere - III. Re-evaluation of the structure and composition of Highate Copalite and Glessite. Org. Geochem. 20:1993;1027-1038.
8. Anderson, K. B. and Le Page, B. A. (1995) The nature and fate of natural resins in the geosphere - VI. Analysis of fossil resins from Axel Heiberg Island, Canadian Arctic. In Amber, Resinite and Fossil Resins (Edited by Anderson, K. B. and Crelling, J. C.), pp. 170-192. ACS Symposium Series 617, ACS publications.
9. Anderson K. B., Winans R. E. The nature and fate of natural resins in the geosphere. 1. Evaluation of pyrolysis-gas chromatography-mass spectrometry for the analysis of natural resins and resinites. Anal. Chem. 63:1991;2901-2908.
10. Anderson K. B., Winans R. E., Botto R. E. The nature and fate of natural resins in the geosphere - II. Identification, classification and nomenclature of resinites. Org. Geochem. 18:1992;829-841.
11. Bastard J., Duc D. K., Fetizon M. CMR spectroscopy of labdanic diterpenes and related substances. J. Nat. Prod. 47:1984;592-599.
12. Bohlmann F., Czerson H. Phytochem. 18:1979;115-119.
13. 13C NMR spectroscopy for quantitative analysis of coals: study of whole coals and maceral concentrates. Energy & Fuels. 1:1987;173-181.
14. Brooks J. D., Steven J. R. The constituents of an Australian brown coal resin. Fuel. 46:1967;13-18.
15. Cano R. J., Borucki M. K. Revival and identification of bacterial spores in 25- to 40-million-year-old Dominican amber. Science. 568:1995;1060-1063.
16. Carman R. M., Cowley D. E., Marty R. A. Diterpenoids XXV. Dundathic acid and polycommunic acid. Aust. J. Chem. 23:1970;1655-1665.
17. Challinor J. M. A pyrolysis-derivatisation-gas-chromatography technique for the structural elucidation of some synthetic polymers. J. Anal. Appl. Pyrol. 16:1989;323-333.
18. Clifford, D. J. (1994) Maturation effects on the chemical composition of polylabdanoid resinites in coal. MSc thesis, The Pennsylvania State University, U.S.A.
19. Clifford, D. J. (1996) An investigation of polylabdanoid (Class I) resinite maturation by characterization of olefinic functional groups. PhD thesis, The Pennsylvania State University, U.S.A.
20. Clifford D. J., Hatcher P. G. Structural transformations of polylabdanoid resinites during maturation. Org. Geochem. 23:1995;407-418.
21. Clifford, D. J. and Hatcher, P. G. (1995b) Maturation of polylabdanoid (Class Ib) resinites. In Amber, Resinite and Fossil Resins (Edited by Anderson, K. B. and Crelling, J. C.), pp. 92-104. ACS Symposium Series 617, ACS publications.
22. 13C NMR and IR analyses of the structure, ageing and botanical origin of Dominican and Mexican ambers. Phytochem. 22:1983;965-968.
23. Desalle R., Gatesy J., Wheeler W., Grimaldi D. DNA sequences from a fossil termite in Oligo-Miocene amber and their phylogenetic implications. Science. 257:1992;1933-1936.
24. Doddrell D. M., Pegg D. T., Bendall M. R. Distortionless enhancement of NMR signals by polarization transfer. J. Mag. Res. 48:1982;323-327.
25. Gough L. J. Conifer resin constituents. Chem. Ind. 50:1964;2059-2060.
26. Grimalt J. O., Simoneit B. R. T., Hatcher P. G. The chemical affinities between the solvent extractable and the bulk organic matter of fossil resin associated with an extinct podocarpaceae. Phytochem. 28:1989;1167-1171.
27. Grimalt J. O., Simoneit B. R. T., Hatcher P. G., Nissenbaum A. The molecular composition of ambers. Org. Geochem. 13:1988;677-689.
28. Lambert J. B., Frye J. S. Carbon functionalities in amber. Science. 217:1982;55-57.
29. Lambert J. B., Frye J. S., Poinar G. O. Amber from the Dominican republic: analysis by nuclear magnetic resonance spectroscopy. Geoarchaeology. 5:1985;43-52.
30. Lambert, J. B., Johnson, S. C. and Poinar, G. O. Jr. (1995) Resin from Africa and South America: criteria for distinguishing between fossilized and recent resin based on NMR spectroscopy. In Amber, Resinite and Fossil Resins (Edited by Anderson, K. B. and Crelling, J. C.), pp. 193-202, ACS Symposium Series 617, ACS publications.
31. Langenheim J. H. Amber: a botanical origin. Science. 163:1969;1157-1169.
32. Langenheim, J. H. (1995) Biology of amber-producing trees: focus on case studies of Hymenaea and Agathis. In Amber, Resinite and Fossil Resins (Edited by Anderson, K. B. and Crelling, J. C.), pp. 1-31, ACS Symposium Series 617, ACS publications.
33. Langenheim J. H., Beck C. W. Infrared spectra as a means of determining botanical sources of amber. Science. 149:1965;52-55.
34. Mills J. S., White R., Gough L. J. The chemical composition of Baltic amber. Chem. Geol. 47:1984;15-39.
35. Mills J. S., White R., Gough L. J. The chemical composition of Baltic amber. Chem. Geol. 47:1985;15-39.
36. Murae, T., Shimokawa, S. and Aihara, A. (1995) Pyrolytic and spectroscopic studies of the diagenetic alteration of resinites. In Amber, Resinite and Fossil Resins (Edited by Anderson, K. B. and Crelling, J. C.), pp. 76-91, ACS Symposium Series 617, ACS publications.
37. Pegg D. T., Doddrell D. M., Bendall M. R. Jr. Correspondence between INEPT and DEPT pulse sequences for coupled spin-half nuclei. J. Mag. Res. 51:1983;264-269.
38. Shaka A. J., Barker P. B., Freeman R. Computer-optimized decoupling scheme for wideband applications and low-level operation. J. Mag. Res. 64:1985;547-552.
39. Shaka A. J., Keeler J., Freeman R. Evaluation of a new broadband decoupling sequence: WALTZ-16. J. Mag. Res. 53:1983;313-340.
40. Shaka A. J., Keeler J., Frenkiel T., Freeman R. An improved sequence for broadband decoupling: WALTZ-16. J. Mag. Res. 52:1983;335-338.
41. Starcuk Z., Sklenar V. Composite pulse sequence with variable performance. J. Mag. Res. 62:1985;113-122.
42. Thomas, B. R. (1969) Kauri Resins - modern and fossil. In Organic Geochemistry - Methods and Results (Edited by Eglington, G. and Murphy, M. J. T.), pp. 599-618. Springer-Verlag, Berlin.
43. Thomas, B. R. (1970) Modern and fossil plant resins. In Phytochemical Phylogeny (Edited by Harborne, J. B.), pp. 59-79. Academic Press, New York.
44. Wenkert E., Buckwalter B. L. Carbon-13 nuclear magnetic resonance spectroscopy of naturally occurring substances - X. Pimaridienes. J. Am. Chem. Soc. 94:1972;4367-4369.
45. Wilson M. A. Comment on the paper by B. G. K. van Aarssen and J. W. de Leeuw, Org. Geochem. Vol. 20, pp. 105-106. 1993. Org. Geochem. 20:1993;1091-1092.
46. Wilson M. A., Collin P. J., Vassallo A. M., Russel N. J. The nature of olefins and carboxyl groups in an Australian brown coal resin. Org. Geochem. 7:1984;161-168.
47. 1H CRAMPS NMR derived hydrogen distributions in various coal macerals. Org. Geochem. 20:1993;985-999.
48. Wilson M. A., Hanna J. V., Cole-Clarke P. A., Greenwood P. F., Willett G. D. Structure and reactivity of Latrobe Valley resinites: characterization of fractions separated on the basis of colour. Fuel. 71:1992;1097-1104.
49. Wilson M. A., Hanna J. V., Cole-Clarke P. A., Willett G. D., Greenwood P. F. Extraction and methylation of Latrobe Valley resinites. Org. Geochem. 18:1992;555-565.
50. Wu X., Burns S. T., Zilm K. W. Spectral editing in CPMAS NMR. Generating subspectra based on proton multiplicities. J. Mag. Res. Series A. 111:1994;29-36.