The nature and fate of natural resins in the geosphere. XII. Investigation of C-ring aromatic diterpenoids in Raritan amber by pyrolysis-GC-matrix isolation FTIR-MS
Tóm tắt
Upper Cretaceous amber from the Raritan Formation (Sayerville, New Jersey) has been investigated by Pyrolysis-GC-MS and Pyrolysis-GC-matrix isolation FTIR-MS. Results establish the existence of two distinct forms of amber in this deposit. Both forms are Class Ib ambers, but they are unambiguously differentiated on the basis of their (intact) diterpenoid composition. The presence of callitrisate in both forms, and cupraene in samples designated form 1, strongly suggest that both derive from related-but-distinct species within the Cupressaceae. In addition to callitrisate, dehydroabietate and analogous 17-nor-, 16,17-dinor- and 15,16,17-trinor- analogues of these compounds are also observed. The distributions of these products in multiple samples suggest that they are the result of biological emplacement, rather than diagenetic modification of the parent compounds. This indicates that the distributions of diterpenes observed in these samples are representative of the original bioterpenoids and, hence, are useful for chemotaxonomic analyses.
Tài liệu tham khảo
Langenheim JH: Plant Resins – Chemistry, Evolution, Ecology and Ethnobotany. 2003, Timber Press, Portland, 586-
Nip M, De Leeuw JW, Crelling JC: Chemical structure of bituminous coal and its constituting maceral fractions as revealed by flash pyrolysis. Energy & Fuels. 1992, 6 (2): 125-36. 10.1021/ef00032a003.
Crelling John C, Kruge MA: Petrographic and chemical properties of Carboniferous resinite from the Herrin No. 6 coal seam. International Journal of Coal Geology. 1998, 37 (1–2): 55-71. 10.1016/S0166-5162(98)00021-4.
van Bergen P, Collinson ME, Scott AC, de Leeuw JW: Unusual resin chemistry from Upper Carboniferous Pteridosperm resin rodlets. ACS Symposium Series. 1995, 617 (Amber, Resinite, and Fossil Resins): 149-169.
Anderson Ken B, Winans RE, Botto RE: The nature and fate of natural resins in the geosphere-II. Identification, classification, and nomenclature of resinites. Organic Geochemistry. 1992, 18 (6): 829-41. 10.1016/0146-6380(92)90051-X.
Anderson Ken 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 of resinite and revision of the classification of Class I resinites. Organic Geochemistry. 1994, 21 (2): 209-12. 10.1016/0146-6380(94)90155-4.
Anderson Ken B: The nature and fate of natural resins in the geosphere. Part V. New evidence concerning the structure, composition, and maturation of Class I (polylabdanoid) resinites. ACS Symposium Series. 1995, 617 (Amber, Resinite, and Fossil Resins): 105-29.
Langenheim JH: Biology of amber-producing trees: Focus on case studies of Hymenaea and Agathis. ACS Symposium Series. 1995, 617 (Amber, Resinite, and Fossil Resins): 1-31.
Rice PC: Amber – The Golden Gem of the Ages. 1993, Kosciuszko Foundation, New York, 289-
Grimaldi D: Amber: Window to the Past. 1996, Harry N. Abrams/American Museum of Natural History, New York, 216-
Otto A, Wilde V: Sesqui-, Di-, and Triterpenoids as Chemosystematic Markers in Extant Conifers – A Review. The Botanical Review. 2001, 67 (2): 141-238.
Vavra N: Chemical characterization of fossil resins ("amber") – A critical review of methods, problems and possibilities: determination of mineral species, botanical sources and geographical attribution. Abh Geol B. 1993, 49: 147-157.
Langenheim JH, Beck CW: Catalogue of Infrared Spectra of Fossil Resins (Ambers) I. North And South America. 1968, Botanical Museum Leaflets, Harvard University, 22 (3): 65-120.
Anderson Ken B, LePage Ben A: The nature and fate of natural resins in the geosphere. Part VI. Analysis of fossil resins from Axel Heiberg Island, Canadian Arctic. ACS Symposium Series. 1995, 617 (Amber, Resinite, and Fossil Resins): 170-92.
Otto A, White JD, Simoneit BRT: Natural product terpenoids in Eocene and Miocene conifer fossils. Science. 2002, 297 (5586): 1543-1545. 10.1126/science.1074225.
Otto A, Simoneit BRT, Rember WC: Resin compounds from the seed cones of three fossil conifer species from the Miocene Clarkia Flora, Emerald Creek, Idaho, USA, and from related extant species. Review of Palaeobotany and Palynology. 2003, 126: 225-241. 10.1016/S0034-6667(03)00088-5.
Troost G: Description of a variety of amber, and of a fossil substance supposed to be the nest of an insect discovered at Cape Sable, Magothy River, Ann-ArundelCounty, Maryland. American Journal of Science. 1821, 3: 8-15.
Grimaldi D, Beck CW, Boon JJ: Occurrence, chemical characteristics, and paleontology of the fossil resins from New Jersey. American Museum Novitates. 2948: 1-28.
Grimaldi D, Shedrinsky A, Wampler TP: A remarkable deposit of fossiliferous amber from the Upper Cretaceous (Turonian) of New Jersey. "Studies on fossils in amber, with particular reference to the Cretaceous of New Jersey. Edited by: Grimaldi D. 2000, Backhuys, Publishers, Leiden, The Netherlands, 1-76.
Rowland SJ, Alexander R, Kagi RI: Analysis of trimethylnaphthalenes in petroleum by capillary gas chromatography. Journal of Chromatography. 1984, 294: 407-12. 10.1016/S0021-9673(01)96153-9.
Anderson Ken B, Winans RE: 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. Analytical Chemistry. 1991, 63: 2901-2908. 10.1021/ac00024a019.
Carman RM, Deeth HC: Diterpenoids. XIV. 4-Epidehydroabietic acid from the oleoresin of Callitris. Australian Journal of Chemistry. 1967, 20 (12): 2789-93.
Gough LJ: Callitrisic acid: a new diterpenoid. Tetrahedron Letters. 1968, (3): 295-8. 10.1016/S0040-4039(01)98748-9.
Tabacik C, Poisson C: Juniperus phoenicea diterpenes, minor constituents. Phytochemistry. 1971, 10 (7): 1639-45. 10.1016/0031-9422(71)85039-2.
De Pascual TJ, San Feliciano A, Tabernero ML, Del Corral JMM, Barrero AF, Grande M: Components of the berries of Juniperus phoenicea L. I. Acid fraction. Anales de Quimica. 1978, 74 (3): 459-64.
De Pascual TJ, San Feliciano A, Miguel del Corral JM, Barrero AF: Terpenoids from Juniperus sabina. Phytochemistry. 1983, 22 (1): 300-1. 10.1016/S0031-9422(00)80113-2.
San Feliciano A, Miguel del Corral JM, Gordaliza M, Salinero MA, Del Rey B: Acidic constituents of Juniperus phoenicea subsp. turbinata leaves. Fitoterapia. 1993, 64 (2): 185-6.
Lee C-K, Fang Min J, Cheng Y-S: Abietanes from leaves of Juniperus chinensis. Phytochemistry. 1994, 35 (4): 983-6. 10.1016/S0031-9422(00)90652-6.
Almendros G, Sanz J, Velasco F: Signatures of lipid assemblages in soils under continental Mediterranean forests. European Journal of Soil Science. 1996, 47 (2): 183-196. 10.1111/j.1365-2389.1996.tb01389.x.
El-Sayed AM: Diterpene constituents of Juniperus polycarpos and their antimicrobial and anti-inflammatory activities. Zagazig Journal of Pharmaceutical Sciences. 1998, 7 (1): 80-86.
Guillen MD, Manzanos MJ: Extractable Components of the Aerial Parts of Salvia lavandulifolia and Composition of the Liquid Smoke Flavoring Obtained from Them. Journal of Agricultural and Food Chemistry. 1999, 47 (8): 3016-3027. 10.1021/jf981260r.
Chamy MC, Piovano M, Gambaro V, Garbarino JA, Nicoletti M: Dehydroabietane diterpenoids from Calceolaria ascendens. Phytochemistry. 1987, 26 (6): 1763-5. 10.1016/S0031-9422(00)82285-2.
Chamy MC, Piovano M, Garbarino JA, Gambaro V: Diterpenoids from Caleolaria species. Part 10. Diterpenes from Calceolaria polifolia. Phytochemistry. 1991, 30 (10): 3365-8. 10.1016/0031-9422(91)83211-3.
Zhang H, Sun H: Diterpenoids from Rabdosia kunmingensis. Phytochemistry. 1989, 28 (12): 3405-9. 10.1016/0031-9422(89)80357-7.
Khadzhieva P, Stoyanova-Ivanova B: Callitrisic acid and sterols in the flowers of Bulgarian oil-bearing rose (Rosa damascena Mill). Adv Mass Spectrom Biochem Med. 1976, 1: 303-7.
Hadjieva P, Palacartcheva E, Dyulgerov A, Tzvetkova A: New di- and triterpenoids for Alchemilla genus (Rosaceae). Bulgarian Chemistry and Industry. 2000, 71 (1–2): 56-57.
Garcia Vallejo MC, Nascimento EA, Morais S: Volatile wood oils of the Brazilian Pinus caribaea var. Hondurensis and Spanish Pinus Pinaster var. Mediterranea. Journal of the Brazilian Chemical Society. 1994, 5 (2): 107-12.
McDonald AG, Gifford JS, Dare PH, Steward D: Characterization of the condensate generated from vacuum drying of radiata pine wood. Holz als Roh- und Werkstoff. 1999, 57 (4): 251-258. 10.1007/s001070050052.
McDonald IRC, Porter LJ: Resin and fatty acid composition of Pinus radiata whole wood, and its relation to the yield and composition of New Zealand tall oil. New Zealand Journal of Science. 1969, 12 (2): 352-62.
Arrabal C, Cortijo M, Fernandez de Simon B, Garcia-Vallejo MC, Cadahia E: Pinus pinaster oleoresin in plus trees. Holzforschung. 2002, 56 (3): 261-266. 10.1515/HF.2002.043.
Erdtman H: Chemical principles in chemosystematics. Rec Adv Phytochem. 1968, 1: 13-26.
Basinger JF: The fossil forests of the Buchanan Lake Formation (Early Tertiary), Axel Heiberg Island, Canadian Arctic Archipelago: preliminary floristics and paleoclimate. "Tertiary Fossil Forests of the Geodetic Hills Axel Heiberg Island, Arctic Archipelago". Geological Survey of Canada Bulletin. Edited by: Christy RL, McMillan NJ. 1991, 403: 39-66.
Hollick A, Jeffrey EC: Studies of Cretaceous coniferous remains from KreischerviIle, New York. Mem New York Bot Gard. 1909, 3: 1-138.
Knowlton EH: American amber-producing tree. Science. 1896, 3: 582-584. 10.1126/science.3.68.582.
Enzell CR, Wahlberg I: Mass spectrometric studies of diterpenes. VI. Aromatic diterpenes. Acta Chemica Scandinavica. 1969, 23 (3): 871-91.
Bory S, Fetizon M: Determination of the configuration of di- or triterpene esters by infrared spectroscopy. Bulletin de la Societe Chimique de France. 1964, 3: 570-3.
Zinkel DF, Zank LC, Wasolowski MF: Diterpene resin acids. A compilation of infrared, mass, nuclear magnetic resonance, ultraviolet spectra, and gas chromatographic retention data (of the methyl esters). 1971, U. S. Department of Agriculture, 191-