Amber, Resinite, and Fossil Resins

Downloaded by FREIE UNIV BERLIN on March 6, 2017 | http://pubs.acs.org Publication Date: May 5, 1996 | doi: 10.1021/bk-1995-0617.ix002

Author Index Aihara, Α., 76 Anderson, Ken B., 105,170 Bada, Jeffrey L., 255 Beck, CurtW., 130 Clifford, David J., 92 Collinson, M. E., 149 Crelling, JohnC.,218 de Leeuw, J. W., 149 Dutta, Richard, 263 Grimaldi, David Α., 203 Halpine, S. M., 234 Hatcher, Patrick G., 92 Johnson, SuzanneC.,193 Kosmowska-Ceranowicz, Barbara, 130 Lambert, Joseph B., 193 Langenheim, Jean Η., 1

LePage, Ben Α., 170 Li, L., 279 Miller, J. D , 279 Murae, Tatsushi, 76 Nissenbaum, Arie, 32 Poinar, George O., Jr., 193,255 Poinar, Hendrik N., 255 Schobert, Harold H., 263 Scott, A.C.,149 Shimokawa, Shuji, 76 Stout, EdithC.,130 Stout, Scott Α., 43 van Bergen, P. F., 149 Wang, Xueyun S., 255 Yakir, Dan, 32 Yu, Q., 279

Affiliation Index American Museum of Natural History, 203 Amoco Oil Company, 105,170 Kyushu University, 76 NIOZ, 149 National Gallery of Art, 234 Northwestern University, 193 Pennsylvania State University, 92,263 Polish Academy of Science, 130 Southern Illinois University, 218 University of Alberta, 170

University of California-Berkeley, 193,255 University of California-San Diego, 255 University of California-Santa Cruz, 1 University of London, 149 University of Munich, 255 University of Utah, 279 Unocal Corporation, 43 Vassar College, 130 Weizmann Institute of Science, 32

Subject Index A Abstraction of amino acid α-hydrogen, role in racemization and serine dehydration, 256 African resin, distinguishing between fossilized and recent resin, 193-201

Agathis distribution, 21-22 resin production, 22 source of Baltic amber, 22-24 Age of Dominican amber Lambert et al. study, 205,207f,208-209 localities of amber, 204-206/ 290

Anderson and Crelling; Amber, Resinite, and Fossil Resins ACS Symposium Series; American Chemical Society: Washington, DC, 1995.

291


INDEX

Age of Dominican amber—Continued previous studies, 204 relative dating based on inclusion of organisms, 211,214-215 stratigraphie data, 209-213 Aliphatic carbons, role in maturation of polylabdanoid resinites, 97-99 Aliphatic hydrocarbons, Upper Carboniferous pteridosperm resin rodlets, 153,155/,157,161 Amber applications, 171 classification system, 11 definition, 2 Dominican, See Dominican amber history of interest, 33 occurrence, 32 preservation of entrapped fossil materials, 106 research interest, 1 stable isotope composition, 33-41 study techniques, 33 Amber fossils, reasons for interest, 204 Amber matrix, amino acids, 255-261 Amber-producing trees, biology, 1-24 American coals, petrology of resinite, 218-230 American painting, amino acid analysis of paint samples, 240,242-244/ Amino acid analysis system of National Gallery of Art, characterization of proteinaceous paint binders, 234 Amino acid(s) in amber matrix and entombed insects composition, 257-261 experimental procedure, 256-257 inhibition of biomolecular degradation by amber, 261 natural resins, See Trace amino acid composition of natural resins preservation, 255 quantity isolated from intact insect tissues, 259 samples, 256-257 Angiosperms, See Flowering plants

Anhydrous conditions, role in amino acids in amber matrix and entombed insects, 255-261 Anhydrous environment of amber, importance in DNA preservation, 256 Aqueous environment, role in amino acids in amber matrix and entombed insects, 255-261 Araucariaceae, resin production, 5-6 Aromatic hydrocarbons, Upper Carboniferous pteridosperm resin rodlets, 156-159,161 Artists' materials, elucidation of nature, 234-251 Axel Heiberg Island, Canadian ArctiC., fossil resins, 170-190 Β Balsam, description, 11-12 Baltic amber from Agathis chemistry, 22-23 hypothesis to resolve dilemma, 24 massive accumulations, 23 plant remains, 23-24 pros and cons, 22,231 See also Succinite Betulaceae, resin production, 11 Bicadinanes characterization, 43-72 occurrence in oils, 45 Biology, amber-producing trees, 1-24 Biomolecular degradation, inhibition, 261 Blisters, See Spheroidal pockets Branch resin of Hymenaea, chemical ecology, 19-21 Burseraceae, resin production, 9

C 13

C-NMR spectroscopy, age of Dominican amber, 203-215 Canadian ArctiC., fossil resins, 170-190 Carbonyl carbons, role in maturation of polylabdanoid resinites, 95,97



292

A M B E R , RESINITE, AND FOSSIL RESINS

Characterization, macroscopic fossil Columbia, distinguishing between resins from western coals, 280-283 fossilized and recent resin, 193-201 Chemical composition of gedanite and Composition gedanosuccinite, 130-147 amino acid(s) in amber matrix and constituents, 134,136-138 entombed insects, 257-261 experimental procedure, 135 class I resinites, 105-127 GC-MS, 135,139-143 gedanite and gedanosuccinite, 134-143 IR spectroscopy, 143-146 Compounds Τ and W, identification in misidentification, 135 oils, 45 Chemical ecological effects, resins, 5 Conifers, resin production, 5-7,32 Chemical ecology of Hymenaea resins Conventional pyrolysis, maturation branch resin, 19-21 of polylabdanoid resinites, leaf resin, 17-18 99,100/103 pod resin, 18-19 Copals trunk resin, 19-21 description, 12,195,200 Class I resinites NMR spectra, 200-201 Α-ring defunctionalized bicyclic Cross-polarization magic-angle spinning products, 124-127 C-NMR spectroscopy, maturation of description, 150 polylabdanoid resinites, 92-103 distribution of bicyclic products Cupressaceae, resin production, 7 la, 113,114-117 Ib, 112/113 IC., 117,120/ D enantiomeric characteristics vs. chromatographic behavior, 117,119-121 Dammar resin evidence for regular and enantio characterization of hydrocarbons, bicyclic products, 120,122-124,126 43-72 experimental procedure, 111 chemical composition, 265-266 instrumentation, 105 comparison MS, 113,115,117-119i single-stage hydrocracking and reverse structures, 106-107 temperature stage hydrogénation subclassifications, 106 products, 275,276/ Class la ambers, relationship with Utah resinite and liquefaction products, Pseudolarix resinite and succinite, 271,274/275 188-189 composition, 44-45 Class Ib resinites conversion to liquids and solids, 271,272/ definition, 92 description, 12 formation, 92,94/ experimental procedure, 263,266-267 See also Polylabdanoid resinites factors affecting jet fuel stability, 264 Classes II and III, description, 150 feedstock selection, 264-265 Coal(s) hydrocarbons derived, 43-72 American, petrology of resinite, 218-230 liquefaction product western, recovery and characterization of vs. reaction time, 267,270/ macroscopic fossil resins, 279-286 vs. temperature, 267,268/ Coal macerals polycadinene dissociation, 45 description, 76 presence of bicadinanes, 45 maturity vs. degree of modification of previous studies, 263,265 molecular structures, 76 products vs. fraction, 271,273/ 13


293


INDEX

Dammar resin—Continued quantitation of liquefaction product distribution vs. reaction time, 267,271,272/ vs. temperature, 267,269/ samples, 266 structures of products, 275 use as jet fuel, 275 Depurination, description, 256 Diagenetic alteration of resinites, pyrolytic and spectroscopic studies, 76-90 elemental composition, 78/79,81 experimental procedure, 77,79 IR spectra, 80-82/84/ pyrolysis-GC-MS, 83-84,86-90 samples, 79,80 thermal alteration of IR spectra, 81,83,85/ Dipterocarpaceae, resin production, 7-8 Distinguishing between fossilized and recent resin using NMR spectroscopy copal spectra, 195,200-201 exomethylene resonances, 194-199 experimental procedure, 194 samples, 194 saturated resonances, 195 unsaturated carbon resonances, 193 DNA preservation, importance of anhydrous environment of amber, 256 Dominican amber age, 203-215 fossils, 203

Flowering plants, resin production, 7-9,11 Fluorescence microscopy, petrology of resinite in American coals, 218-230 Fly, amino acid preservation, 255 Fossil resins chemical characterization, 193-194 classification, 150 definition, 2 distinguishing from recent resin, 193-201 economics, 279-280 from Axel Heiberg Island experimental procedure, 178 future work, 190 location, 171,174/ MS of compounds, 178-179 product distribution in pyrolyzates of unassociated resinites, 178-188 of associated resinites, 178,181/183 of cone-scale resinites, 182-186 Pseudolarix resinite relationship with succinite and class la ambers, 188-189 samples, 173-178 speculation on botanical nature of trees, 171-173 from western coals, recovery and characterization, 279-286 liberation from other coalmacerals,279 Fourier transform IR spectroscopy, diagenetic alteration of amber, 76-90 G

Ecological effects, resins, 2,5 Egyptian paint binders amino acid analysis of paint samples American painting, 240,242-243,244/ Egyptian paint binders, 243,245-250 ancient use of resin, 250 collagen-containing samples, 245-247/ group A samples, 245,248-249/ Moroccan sandarac resin, 250 Entombed insects, amino acids, 255-261 Evolutionary position, reflection of age of amber, 211,214-215

GC-MS, chemical composition of gedanite and gedanosuccinite, 130-146 Gedanite chemical composition, 134-146 discovery, 130-133 Gedanosuccinite chemical composition, 134-146 discovery, 131-133 Giles Creek resinites, maturation, 92-103 Goodwins resinites, maturation, 92-103 Gymnosperms, See Conifers



294

A M B E R , RESINITE, A N D FOSSIL RESINS

H

M

Hamamelidaceae, resin production, 9 Heaphy resinites, maturation, 92-103 Hydrocarbons in dammar resins and Miocene rocks and oils, See Resinderived hydrocarbons in dammar resins and Miocene rocks and oils Hymenaea chemical ecology of resins, 13,15-17 description, 12-13 distribution, 13 distinguishing between fossilized and recent resin, 193-201 evidence for amber, 21 relation to amber trees, 13,14/

Macroscopic fossil resins from western coals characterization, 280-283 future work, 286 selective flotation, 283-285 solvent refining of concentrates, 285-286 occurrence, 279 Mahakam Delta, Indonesia, resin-derived hydrocarbons in dammar resins and Miocene rocks and oils, 43-72 Maturation, class I resinites, 105-127 Maturation of polylabdanoid resinites cross-polarization magic-angle spinning C-NMR spectroscopy aliphatic carbons, 97-99 carboxyl carbons, 95,97 olefinic carbons, 97 spectra, 95,96/ experimental procedure, 93,95 pathways, 102/103 pyrolysis-GC-MS, 98-100/1011 samples, 93 Maturity role of bicadinane distribution, 61,65,69-72 sediment samples, importance of determination, 76-77 Metasequoia, characterization using pyrolysis-GC-MS, 170-190 Migration, role of bicadinane distribution, 61,65,69-72 Miocene rocks and oils, characterization of hydrocarbons, 43-72 Moroccan sandarac resin, trace amino acid composition, 250

Insects, entombed, amino acids, 255-261 Interconnected canals, description, 3,5 IR spectroscopy chemical composition of gedanite and gedanosuccinite, 130-146 diagenetic alteration of resinites, 76-90 Isotopes, stable, in amber, 33-41

Jet fuel factors affecting stability, 264 feedstock selection, 264-265 use of dammar resin, 365-366

Κ Kenya, distinguishing between fossilized and recent resin, 193-201

I3

Ν

National Gallery of Art, amino acid analysis system for characterization of proteinaceous paint binders, 234 Leaf resin of Hymenaea, chemical ecology, Natural resins chemical composition, 149 17-18 trace amino acid composition, 234-251 Leguminosae, resin production, 7 L


295

INDEX

NMR spectroscopy advantages, 193-194 distinguishing between fossilized and recent resin, 194-201


Ο Oils, Miocene, characterization of hydrocarbons, 43-72 Olefinic carbons, role in maturation of polylabdanoid resinites, 97 Oleoresins, description, 11 Ovoid pockets, description, 3,5

Pseudolarix, characterization using pyrolysis-GC-MS, 170-190 Pteridosperm resin rodlets, Upper Carboniferous, resin chemistry, 149-166 Pyrolysis-GC-MS diagenetic alteration of resinites, 76-90 fossil resins from Axel Heiberg Island, 170-190 maturation of polylabdanoid resinites, 92-103 structure, composition, and maturation of class I resinites, 106,108-109,110/

Ρ Petrology of resinite in American coals primary resinite, 222-230 secondary resinite, 224 Phenols, Upper Carboniferous pteridosperm resin rodlets, 157,160/, 161 Physical ecological effects, resins, 5 Pinaceae, resin production, 5-6 Pinus, characterization using pyrolysis-GC-MS, 170-190 Plant(s), resin production, 32 Plant families of resin-producing trees conifers, 5-7 flowering plants, 7-9,11 Plant resins, contribution to crude oil, 43 Pod resin of Hymenaea, chemical ecology, 18-19 Podocarpaceae, resin production, 7 Polylabdanoid resinites C8-C17 exomethylene depletion, 92-94/ description, 92 maturation, 93-103 polymerization, 92,94/ structure, composition, and maturation, 105-127 See also Class lb resinites Polymeric resins, precursor groups, 150 Primary resinite in American coals, petrology, 222-230 Proteinaceous paint binders, amino acid analysis system, 234

Recent resin, distinguishing from fossilized resin, 193-201 Recovery, macroscopic fossil resins from western coals, 283-286 Resin(s) chemical ecological effects, 5 commercial resin terminology, 10i,l 1-12 definitions, 1 from Africa and South America, criteria for distinguishing between fossilized and recent resin using NMR spectroscopy, 193-201 justification for existence, 2-5 multifarious ecological roles, 2-3 natural, See Natural resins physical ecological effects, 5 production by plants, 32 secretory tissue types, 3,5 Resin chemistryfromUpper Carboniferous pteridosperm resin rodlets, 149-166 aliphatic hydrocarbons, 153,155/157,161 aromatic hydrocarbons, 156-159,161 chemical composition, 161-165 differences between rodlets, 165-166 experimental procedure, 150-153 phenols, 157,160/161 pyrolysis-GC-MS of loose resin rodlets, 153,154/ samples, 151,152/ trace of pyrolyzate of in situ resin rodlets, 153,154/



296

A M B E R , RESINITE, AND FOSSIL RESINS

Resin-derived hydrocarbons in dammar resins and Miocene rocks and oils, 43-72 bicadinane distribution effect on maturity and migration, 61,65,69-72 bulk composition, 48-49 dammar resin characterization generated hydrocarbon heating, 55-63 indigenous hydrocarbons, 49-55 experimental description, 45-46 oils, bicadinanes, 60-68 samples, 46,47r solubility, 48 Resin-producing trees, plant families, 5-9,11 Resin rodlets chemical constituents, 150 origin, 150 Upper Carboniferous pteridosperm, 149-166 Resinite(s) chemical components, 77 classification, 77,106,150 classification system, 11 definition, 2,150 diagenetic alteration, 76-90 factors affecting composition, 77 sources, 77 study techniques, 77,79 Resinite macerals market value, 223 modes of occurrence, 218 occurrence, 218-222 petrology, 222-230 type, 218 Resinous artists' materials, elucidation of nature, 234-251 Resinous material, fossilization, 193 Rocks, Miocene, characterization of hydrocarbons, 43-72

SandaraC., description, 12 Secondary resinite in American coals, petrology, 224

Secretory tissue types, resins, 3,5 Selective flotation, macroscopic fossil resins from western coals, 283-285 Simultaneous pyrolysis methylation, maturation of polylabdanoid resinites, 98/,99,101r Solvent refining of concentrates, macroscopic fossil resins from western coals, 285-286 South American resin, distinguishing between fossilized and recent resin, 193-201 Spectroscopy, diagenetic alteration of resinites, 76-90 Spheroidal pockets, description, 3,5 Stable isotope composition of amber, 33-41 age, 39 C., H, and Ο isotope distribution in organic matter, 37-39 C/H atomic ratios, 39^0 experimental materials, 33 future work, 41 information obtained, 33 isotopic homogeneity in single deposit, 34,36-37 isotopic values, 34,35i localities of collection, 34,35i weathering, 36r,37 Stable isotope ratio, determination, 34 Structural characteristics of resinites, reasons for interest, 106 Structure, class I resinites, 105-127 Succinite abundance, 171 comparison gedanite and gedanosuccinite, 130-146 Pseudolarix resinite and class la ambers, 188-189 See also Baltic amber

Taxodiaceae, resin production, 6 Terpenoid resins, 1^1


297


INDEX

Trace amino acid composition of natural resins artists' materials, 235 botanical nomenclature and artists' materials, 236-237 experimental description, 235 future research, 251 occurrence, 236,238-239* reason for interest, 234-235 sample preparation, 237,240 Trunk resin of Hymenaea, chemical ecology, 19-21

U Upper Carboniferous pteridosperm resin rodlets, resin chemistry, 149-166 Utah fossil resin industry, history, 279-280 Utah resinite, chemical model for reactions, 263-276 W Western coals, recovery and characterization of macroscopic fossil resins, 279-286

Production: Susan Antigone Indexing: Deborah H. Steiner Acquisition: Michelle D. Althuis & Rhonda Bitterli The cover design was suggested by David A. Grimaldi and is based on a photograph by Ed Bridges, provided courtesy of the American Museum of Natural History. Printed and bound by Maple Press, York, PA


Amber, Resinite, and Fossil Resins

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