Abstract
An overview is presented of polycyclic aromatic hydrocarbons containing three or more fused rings that are not the products of thermal reactions during combustion of fossil fuels, but are early diagenic products of higher plant and prokaryotic precursors such as terpenoids, hopanoids and steroids. An attempt is made to summarize the major groups of aromatized compounds that have been isolated from samples of sediments and sedimentary rocks, and to categorize the principal reactions involved in their transformation from terpenoid and steroid precursors. These include abiotic, photochemical and biochemical reactions, while brief attention has been directed to other structural modifications. Advantage has been taken of chemical, photochemical and biochemical analogies to rationalize these reactions. Detailed discussion is presented on microbial reactions that act as primers of aromatization: dehydrogenation, hydroxylation, elimination, loss of tertiary methyl groups, and ring fission reactions. Attention is drawn to critical aspects of identifying biogenic PAHs and to their possible adverse environmental effects.
This is based on a review published in Toxicological and Environmental Chemistry, and its presentation in the present revised and extended form has kindly been authorized by the publisher Gordon and Breach Science Publishers SA.
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References
Abraham W-R (1994) Microbial hydroxylation of sclareol. Phytochemistry 36: 1421–1424
Aeckersberg F, Bak F, Widdel F (1991) Anaerobic oxidation of saturated hydrocarbons to CO2 by a new type of sulfate-reducing bacterium. Arch Microbiol 156: 5–14
Ageta H, Shiojima K, Arai Y (1987) Acid-induced rearrangement of triterpene hydrocarbons belonging to the hopane and migrated hopane series. Chem Pharm Bull 35: 2705–2716
Akhtar M, Barton DHR (1961) The photochemical rearrangement of hypochlorites. J Amer Chem Soc 83: 2213–2214
Anliker R, Rohr, Heusser H (1955) Über Steroide and Sexualhormone. 205 Mitteilung. Über weitere Umlagerungen in der Ringen C and D der Steroide. Heiv Chim Acta 38: 1171–1177
Aoyama Y, Yoshida Y, Sato R (1984) Yeast cytochrome P-450 catalyzing lanosterol 14ademethylation II. Lanosterol metabolism by purified P-45014DM and by intact microsomes. J Biol Chem 259: 1661–1666
Aquino R, de Simone F, Vincieri FF, Pizza C, Gacs-Baitz E (1990) New polyhydroxylated triterpenes from Uncaria tomentosa. J Nat Prod 53: 559–564
Arigoni D, Barton DHR, Bernasconi R, Djerassi C, Mills JS, Wolff RE (1960) The constitutions of dammarenolic and nyctanthic acid. J Chem Soc 1900–1905
Badger GM, Buttery RG, Kimber RWL, Lewis GE, Moritz AG, Napier IM (1958) The formation of aromatic hydrocarbons at high temperature: I. Introduction. J Chem Soc 2449–2452
Badger GM, Donnelly JK, Spotswood TM (1965) The formation of aromatic hydrocarbons at high temperatures: XIV. The pyrolysis of some tobacco constituents. Aust J Chem 18: 249–1266
Bagli JF, Morand PF, Wiesner K, Gaudry R (1964) A simple synthesis of equilin Tetrahedron Lett 8: 387–389
Balch GC, Metcalf MC, Huestis SY (1995) Identification of potential fish carcinogens in sediment from Hamilton Harbour, Ontario, Canada. Environ Toxicol Chem 14: 79–91
Barakat, AO (1994) Computerized GC/MS detection of monoaromatic and triaromatic steroid hydrocarbons in Alamein crude oil. J High Resol Chromatogr 17: 549–552
Barton DHR, Beaton JM (1961) A synthesis of aldosterone acetate. J Amer Chem Soc 83: 4083–4089
Biggs WR, Fetzer JC (1996) Analytical techniques for large polycyclic aromatic hydrocarbons: a review. Trends Anal Chem 15: 196–205
Bird, TG, Fredricks PM, Jones ERH, Meakins GD (1980) Microbiological hydroxylations: 23. Hydroxylations of fluoro-5a-androstanones by the fungi Calonectria decora, Rhizopus nigricans, and Aspsrgillus ohraceus. J Chem Soc Perkin I 750–755
Björseth A, Knutzen J, Skei J (1979) Determination of polycyclic aromatic hydrocarbons in sediments and mussels from Sandefjord, W Norway, by glass capillary chromatography. Sci Total Environ 13: 71–86
Blunt JW, Hartshorn MP, Kirk DN (1969) Reactions of epoxides: XVII “Backbone rearrangements” of cholest-5-ene and 5,6a-epoxy-5a-cholestane. Tetrahedron 25: 149–153
Bowers A, Villotti R, Edwards JA, Denot E, Halpern 0 (1962) Steroids: CCII. A new route to 19-nor steroids. J Amer Chem Soc 84: 3204–3205
Braude EA, Jackman LM, Linstead RP, Lowe G (1960) Hydrogen transfer XII. Dehydrogenation of “blocked” hydroaromatic compounds by quinones. J Chem Soc 3123–3132
Buckel W (1992) Unusual dehydrations in anaerobic bacteria. FEMS Microbiol Revs 88: 211–232
Burchill P, Herod AA, Pritchard E (1982) Estimation of basic nitrogen compounds in some coal liquefaction products. J Chromatogr 246: 271–295
Burchill P, Herod AA, Pritchard E (1982) Identification of sulphur heterocycles in coal tar and pitch. J Chromatogr 242: 1–64
Burgstahler AW (1957) A contribution to the anthrasteroid problem. The location of the aromatic C-methyl group and the position of the conjugated double bond. J Amer Chem Soc 79: 6047–6050
Carman RM (1965) The synthesis of dihydro-and tetrahydro-canaric acid. Aust J Chem 18: 1493–1496
Carman RM, Cowley D (1965) The structure and partial synthesis of canaric acid. Aust J Chem 18: 213–217
Carruthers W, Watkins DAM (1964) The constituents of high-boiling petroleum distillates: VIII. Identification of 1,2,3,4-tetrahydro-2,2,9-trimethylpicene in American crude oil. J Chem Soc: 724–729
Chaffee AL, Folkes CRJ (1988) Polycyclic aromatic hydrocarbons in Australian coals: III. Structural elucidation by proton nuclear magnetic resonance spectroscopy. Org Geochem 12: 261–271
Chaffee AL, Johns RB (1983) Polycyclic aromatic hydrocarbons in Australian coals: I. Angularly fused pentacyclic tri-and tetraaromatic components of Victorian brown coal. Geochim Cosmochim Acta 47: 2141–2155
Chaffee AL, Strachan MG, Johns RB (1984) Polycyclic aromatic hydrocarbons in Australian coals: II. Novel tetracyclic components from Victoria brown coal. Geochim Cosmochim Acta 48: 2037–2043
Clements WH, Oris JT, Wissing TE (1994) Accumulation and food chain transfer of fluoranthene and benzo[a]pyrene in Chironomus riparius and Lepomis macrochirus. Arch Environ Contam Toxicol 26: 261–266
Corbet B, Albrecht P, Ourisson G (1980) Photochemical or photomimetic fossil triterpenoids in sediments and petroleum. J Amer Chem Soc 102: 1171–1173 (1980)
Corbett RE, Smith RAJ (1969) Lichens and fungi: VI. Dehydration rearrangements of 15hydroxyhopanes. J Chem Soc (C) 44–47
Cuvelier, M-E, Berset C, Richard H (1994) Antioxidant constituents in sage (Salvia officinalis). J Agric Food Chem 42: 665–669
Dannenberg H, Neumann H-G (1964) Dehydrierung von Steroiden: VIII. Dehydrierung von Cholesterin mit Chloranil. Liebigs Ann Chem 675: 152–167
de A Azevedo D, de Aquino Neto FR, Simoneit BRT (1990) Mass spectrometric characteristics of a novel series of ring-C monoaromatic tricyclic terpanes found in Tasmanian tasmanite. Org Mass Spectrom 25: 475–480
de A Azevedo D, de Aquino Neto FR, Simoneit BRT (1994) Mass spectrometric characteristics of two novel series of ring-C monounsaturated tricyclic terpanes found in Tasmanian tasmanite. J Mass Spectrometry 30: 247–256
de A Azevedo D, de Aquino Neto FR, Simoneit BRT, PInto AC (1992) Novel series of tricyclic aromatic terpanes characterized in Tasmanian tasmanite. Org Geochem 18: 9–16
Dorbon M, Schmitter JM, Arpino P, Guiochon G (1982) Carbazoles et lactames du pétrole: méthode d’extraction et caracterisation. J Chromatogr 246: 255–269
Dunlap CE, Warren S (1943) The carcinogenic activity of some new derivatives of aromatic hydrocarbons: I. Compounds related to chrysene. Cancer Res 3: 605–607
Dunlap NK, Sabol MR, Bauer PE, Watt DS, Reibenspies JH, Anderson OP, Seifert WK, Moldowan JM (1985) Synthesis of biological markers in fossil fuels: 3. Degraded and rearranged C27 hopanes. J Org Chem 50: 1826–1829
Elks J, Phillips GH, Taylor DAH, Wyman LJ (1954) Studies in the synthesis of cortisone: VIII. A Wagner-Meerwin rearrangement involving rings C and D of the steroid nucleus. J Chem Soc 1739–1749
Ensminger A, Joly G, Albrecht P (1978) Rearranged steranes in sediments and crude oils. Tetrahedron Lett 18: 1575–1578
Farrington JW, Wakeham SG, Lavramento JB, Tripp BW, Teal JM (1986) Aromatic hydrocarbons in New York Bight polychaetes: ultraviolet fluorescence analyses and gas chromatography/gas chromatography-mass spectrometry analyses. Environ Sci Technol 20: 69–72
Fernandez P, Bayona JM (1989) Determination of bioconcentration factors of isomeric polcyclic aromatic hydrocarbons in polychaete worms by HRGC selective liquid crystalline stationary phases. J High Res Chromatogr 12: 802–806
Fieser LF, Fieser M (1949) Natural products related to phenanthrene. Reinhold, New York, pp 147–155
Fieser LF, Fieser M (1949) Natural products related to phenanthrene. Reinhold, New York, p 131
Florey K, Ehrenstein M (1954) Investigations on steroids: XXII. Studies on oubagenin. I. J Org Chem 19: 1174–1195
Fuchino H, Konishi S, Imai H, Wada H, Tanaka N (1994) A biodegradation product of betulin. Chem Pharm Bull 42: 379–381
Garcia KL, Delfino JL, Powell DH (1993) Non-regulated organic compounds in Florida sediments. Water Res 27: 1601–1613
Gerritse J, Gottschal JC (1993) Two-membered mixed cultures of methanogenic and aerobic bacteria in 02-limited chemostats. J Gen Microbiol 139: 1853–1860
Greiner AC, Spyckerelle C, Albrecht P (1976) Aromatic hydrocarbons from geological sources: I. New naturally occurring phenanthrene and chrysene derivatives. Tetrahedron 32: 257–260
Grimmer G, Jacob J, Naujack K-W, Dettbarn G (1983) Determination of polycyclic aromatic compounds emitted from brown-coal-fired residential stoves by gas chromatography/mass spectrometry. Anal Chem 55: 892–900
Habu N, Samejima M, Yoshimoto T (1989) A novel dioxygenase responsible for the Ca-Cß cleavage of lignin model compounds from Pseudomonas sp. TMY 1009. Mokuzai Gakkaishi 35: 26–29
Hammer CF, Savage DS, Thomson JB, Stevenson R (1964) The conversion of ergosterol to a ring-C benzenoid steroid by a selective aromatization reaction. Tetrahedron 20: 929–941
Hanson JR, Reese PB, Takahashi JA, Wilson MR (1994) Biotransformation of some stemodane diterpenoids by Cephalosporium aphidicola. Phytochemistry 36: 1391–1393
Harshbarger JC, Clark JB (1990) Epizootiology of neoplasms in bony fish of North America. Sci Total Environ 94: 1–32
Hase A, Hites RA (1976) On the origin of polycyclic aromatic hydrocarbons in recent sediments, biosynthesis by anaerobic bacteria. Geochim Cosmochim Acta 40: 1141–1143
Hauke V, Graff R, Wehrung P, Trendel JM, Albrecht P, Riva A, Hopfgartner G, Gülacar FO, Buchs A, Eakin PA (1992) Novel triterpene-derived hydocarbons of the arborane/ fernane series in sediments: II. Geochim Cosmochim Acta 56: 3595–3602
Hauke V, Graff R, Wehrung P, Trendel JM, Albrecht P, Schwark L, Keely BJ, Peakman TM (1992). Novel triterpene-derived hydocarbons of the arborane/fernane series in sediments: I. Tetrahedron 48: 3915–3924
Hawkins WE, Walker WW, Overstreet RM, Lytle T, Lytle JS (1988) Dose-related carcinogenic effects of water-borne benzo[a]pyrene on livers of two small fish species. Ecotoxicol Environ Saf 16: 219–231
Hellou J, Payne JF, Upsall C, Fancey LL, Hamilton C (1994) Bioaccumulation of aromatic hydrocarbons from sediments, a dose-response study with flounder (Pseudopleuronectes americanus). Arch Environ Contam Toxicol 27: 477–485
Helmstetter MF, Alden RW (1994) Release rates of polynuclear hydrocarbons from natural sediments and their relationship to solubility and octanol-water partitioning. Arch Environ Contam Toxicol 26: 282–291
Hirschmann R, Snoddy CS, Hiskey CF, Wendler NL (1954) The rearrangement of the steroid C/D rings. J Amer Chem Soc 76: 4013–4025
Hites RA, LaFlamme RE, Windsor JG, Farrington JF, Deuser WG (1980) Polycyclic aromatic hydrocarbons in an anoxic sediment core from the Pettaquamscutt River ( Rhode Island, USA). Geochim Cosmochim Acta 44: 873–878
Hoffman D, Bondinell WE, Wynder EL (1974) Carcinogenicity of methylchrysenes. Science 183: 215–216
Hosansky NL, Wintersteiner 0 (1956) 8,9-seco derivatives of triacetyldihydroveratramine J Amer Chem Soc 78:3126–3131
Hudlickÿ M (1990) Oxidations in organic chemistry. ACS Monograph 186 American Chemical Society, Washington DC
Hussler G, Albrecht P, Ourisson G, Cesario M, Giolhem J, Pascard C (1984) Benzohopanes, a novel family of hexacyclic geomarkers in sediments and crude oils. Tetrahedron Lett 25: 1179–1182
Hussler G, Connan J, Albrecht P (1984) Novel families of tetra-and hexacyclic aromatic hopanoids predominant in carbonate rocks and crude oils. Org Geochem 6:39–49
Hynning PA, Remberger M, Neilson AH, Stanley P (1993) Identification and quantification of 16-nor-and 19-norditerpenes and their chlorinated analogues in samples of sediment and fish. J Chromatogr 643: 439–452
Ingledew WM, Tresguerres MEF, Canovas JL (1971) Regulation of the enzymes of the hydroaromatic pathway in Acinetobacter calco-aceticus. J Gen Microbiol 68: 273–282
Iorizzi M, de Riccardis F, Minale L, Palagiano E, Riccio R, Debitus C, Duhet D (1994) Polyoxygenated marine steroids from the deep water starfish Styracaster caroli. J Nat Prod 57: 1361–1373
Jones KC, Stratford JA, Waterhouse KS, Furlong ET, Giger W, Hites RA, Schaffner C, Johnston AE (1989) Increases in the polynuclear aromatic hydrocarbon content of an agricultural soil over the last century. Environ Sci Technol 23: 95–101
Jones KH, Smith RT, Trudgill PW (1993) Diketocamphane enantiomer-specific `BaeyerVilliger’ monooxygenases from camphor-grown Pseudomonas putida ATCC 171453. J Gen Microbiol 139: 797–805
Kalvoda J, Heusler K, Ueberwasser H, Anner G, Wettstein A (1963) 19-norsteroide: IV. Über die reduktive Atherspaltung bei 5a-halogen-6/3,19-oxido-steroiden. Helv Chim Acta 46: 1351–1369
Kawamura K, Suzuki I, Fujii Y, Watanabe 0 (1994) Ice core record of polycyclic aromatic hydrocarbons over the past 400 years. Naturwiss 81: 502–505
Keith LA, Telliard WE (1979) Priority pollutants: I - a perspective view. Environ Sci Technol 13: 416–423
Knorr M, Schenk D (1968) Zur Frage der Synthese polyzyklischer Aromate durch Bakterien. Arch Hyg 152 /3: 282–285
Kupchan SM, Court WA, Dailey RG, Gilmore CJ, Bryan RF (1972) Triptolide and tripdiolide, novel antileukemic diterpene triepoxides from Tripterygium wilfordii. J Amer Chem Soc 94: 7194–7195
Kutney JP, Hewitt GM, Kurihara T, Salisbury PJ, Sindelar RD, Stewart KL, Townley PM, Chalmers WT, Jacoli GG (1981) Cytotoxic diterpenes triptolide, tripdiolide and cytotoxic triterpenes from tissue cultures of Tripterygium wilfordii. Can J Chem 59: 2677–2683
LaFlamme RE, Hites RA (1978) The global distribution of polycyclic aromatic hydrocarbons in recent sediments. Geochim Cosmochim Acta 42: 289–303
LaFlamme RE, Hites RA (1979) Tetra-and pentacyclic, naturally-occurring, aromatic hydrocarbons in recent sediments. Geochim Cosmochim Acta 43: 1687–1691
Landrum PF (1989) Bioavailability and toxicokinetics of polycyclic aromatic hydrocarbons sorbed to sediments for the amphipod Pontoporeia hoyi. Environ Sci Technol 23: 588–595
Lang KF, H Buffleb (1958) Die Pyrolyse des a-and ß-methyl-naphthalins. Chem Ber 91: 2866–2870
Leppik RA (1989) Steroid catechol degradation, disecoandrostane intermediates accumulated by Pseudomonas transposon mutant strains. J Gen Microbiol 135: 1979–1988
Lijinsky W, Taha CR (1961) The pyrolysis of 2-methylnaphthalene. J Org Chem 26: 3566–3568
Lohmann F, Trendel JM, Hetru C, Albrecht P (1990) C-29 tritiated ß-amyrin: chemical synthesis aiming at the study of aromatization processes in sediments. J Labelled Cmpds Radiopharmaceut 28: 377–386
Lowe SE, Jain MK, Zeikus JG (1993) Biology, ecology and biotechnological applications of anaerobic bacteria adapted to environmental stresses in temperature, pH, salinity, or substrates. Microbiol Revs 57: 451–509
Lu S-T, Kaplan IR (1992) Diterpanes, triterpanes, steranes and aromatic hydrocarbons in natural bitumens and pyrolysates from different humic coals. Geochim Cosmochim Acta 56: 2761–2788
Ludwig B, Hussler G, Wehrung P, Albrecht P (1981) C26–C29 triaromatic steroid derivatives in sediments and petroleums. Tetrahedron Lett 22: 3313–3316
Mackie RI, White BA, Bryant MP (1991) Lipid metabolism in anaerobic ecosystems. Crit Revs Microbiol 17: 449–479
Madyastha KM, Shankar VN (1994) Role of neutral metabolites in microbial conversion of 3ß-acetoxy-19-hydoxycholest-5-ene into estrone. Appl Environ Microbiol 60: 1512–1518
Mahaffey WR, Gibson DT, Cerniglia CE (1988) Bacterial oxidation of chemical carcinogens, formation of polycyclic aromatic acids from benz[a]anthracene. Appl Environ Microbiol 54: 2415–2423
Mann J (1987) Secondary metabolism, 2nd edn. Clarendon Press, Oxford
Matsuzawa S, Garrigues P, Setokuchi O, Sato M, Yamamoto T, Shimizu Y, Tamura M (1990) Separation and identification of monomethylated polycyclic aromatic hydrocarbons in heavy oil. J Chromatogr 498: 25–33
Meador JP, Stein JE, Reichert WL, Varanasi U (1995) Bioaccumulation of polycyclic aromatic hydrocarbons by marine organisms. Revs Environ Contam Toxicol 143: 79–164
Mikesel MD, Kukor JJ, Olsen RH (1993) Metabolic diversity of aromatic hydrocarbon-degrading bacteria from a petroleum-contaminated aquifer. Biodegradation 4: 249–259
Milanova R, Moore M, Hirai Y (1994) Hydroxylation of synthetic abietane diterpenes by Aspergillus and Cunninghamella species: novel route to the family of diterpenes isolated from Tripterygium wilfordii. J Nat Prod 57: 882–889
Moldowan JM, Fago FH (1986) Structure and significance of a novel rearranged mono-aromatic steroid hydrocarbon in petroleum. Geochim Cosmochim Acta 50: 343–351
Moldowan JM, Fao FJ, Carlson RMK, Young DC, van Duyne G, Clardy J, Schoell M, Pillinger CT, Watt DS (1991) Rearranged hopanes in sediments and petroleum. Geochim Cosmochim Acta 55: 3333–3353
Motohasi N, Meyer R, Molnar J, Parkanyi, Fang X (1995) Chromatographic determination of benz[c]acridines and related compounds in airborne carcinogens. J Chromatogr 710: 117–128
Neilson AH (1994) Organic chemicals in the aquatic environment, distribution, fate and toxicity Lewis, Boca Raton, Florida
Neilson AH, Allard A-S, Hynning P-A, Remberger M (1988) Transformations of halogenated aromatic aldehydes by metabolically stable anaerobic enrichment cultures. Appl Environ Microbiol 54: 2226–2236
Niaussat P, Auger C, Mallet L (1970) Apparition relativ de quantités d’hydrocarbures cancérigènes dans des cultures pures de Bacillus badius, en fonction de la présence, dans le milieu, de certains composés chimiques. CR Acad Sci Paris Ser D 270: 1042–1045
Niaussat P, Mallet L, Ottenwaelder J (1969) Apparition de benzo-3,4-pyréne dans diverses souches de phyto-plancton marin cultivées vitro. Rôle éventuel des bactéries associées CR Acad Sci Paris Ser D 268: 1109–1112
Niimi AJ, Dookhran GP (1989) Dietary absorption efficiencies and elimination rates of polycyclic aromatic hydrocarbons (PAHs) in rainbow trout (Salmo gairdneri). Environ Toxicol Chem 8: 719–722
Nishioka M, Chang H-V Lee ML (1986) Structural characteristics of polycyclic aromatic hydrocarbon isomers in coal tars and combustion products. Environ Sci Technol 20: 1023–1027
Ogilvie AG, Hanson JR (1972) The aromatization of some 3-substituted 5a,6a-epoxysteroids. J Chem Soc Perkin I 1981–1983
Oikari A, Holmbom, Bister H (1982) Uptake of resin acids into tissues of the trout (Salmo gairdneri Richardson). Ann Zool Fennici 19: 61–64
Ougham Hj, Taylor DG, Trudgill PW (1983) Camphor revisited: involvement of a unique monooxygenase in metabolism of 2-oxo-A3–4,5,5-trimethylcyclopentylacetic acid by Pseudomonas putida. J Bacteriol 153: 140–152
Ourisson G, Albrecht P, Rohmer M (1979) The hopanoids. Palaeochemistry and biochemistry of a group of natural products. Pure Appl Chem 51: 709–729
Peakman TM, de Leeuw JW, Rijpstra WI (1992) Identification and origin of 48(14)5a-and 4195a-sterenes and related hydrocarbons in an immature bitumen from the Monterey Formation, California. Geochim Cosmochim Acta 56: 1223–1230
Peakman TM, Ellis K, Maxwell JR (1988) Acid-catalysed rearrangements of steroid alkenes: 2. A re-investigation of the backbone rearrangement of cholest-5-ene. J Chem Soc Perkin Trans I 1971–1075
Peakman TM, Maxwell JR (1987) Early diagenic pathways of steroid alkenes. Org Geochem 13: 583–592
Pelletier SW (1992) Studies in the chemistry of natural products, rearrangement reactions of diterpenoid and norditerpenoid alkaloids. J Nat Prod 55: 1–24
Pereira WE, Rostad CE (1983) Terpenoid marker compounds derived from biogenic precursors in volcanic ash from Mount St Helens, Washington. Geochim Cosmochim Acta 47: 2287–2291
Philp RP, Oung J-U (1988) Biomarkers. Anal Chem 60: 887A - 896A
Prairie RL, Talalay P (1963) Enzymatic formation of testololactone. Biochemistry 2: 203–208
RamaKrishna NVS, Cavalieri EL, Rogan EG, Dolnikowski G, Cerny RL, Gross ML, Jeong H, Jankowiak R, Small GJ (1992) Synthesis and structure determination of the adducts of the potent carcinogen 7,12-dimethylbenz[a]anthracene and deoxyribonucleosides formed by electrochemical oxidation: models for metabolic activation by one-electron oxidation. J Amer Chem Soc 114: 1863–1874
Ramdahl T (1983) Retene–a molecular marker of wood combustion in ambient air. Nature 306: 580–583
Rogge WF, Hildemann LM, Mazurek MA, Cass GR (1993) Sources of fine organic aerosol: 2. Noncatalyst and catalyst-equipped automobiles and heavy diesel trucks. Environ Sci Technol 27: 636–651
Rogge WF, Hildemann LM, Mazurek MA, Cass GR (1993) Sources of fine organic aerosol:
Road dust, tire debris, and organometallic brake lining dust: roads as sources and sinks. Environ Sci Technol 27:1892–1904
Rubinstein I, Sieskind O, Albrecht P (1975) Rearranged sterenes in a shale, occurrence and simulated formation. J Chem Soc Perkin I 1833–1836
Schaeffer P, Adam P, Trendel J-M, Albrecht P, Connan J (1995) A novel series of benzohopanes widespread in sediments. Org Geochem 23:87–89
Schaeffer P, Poinsot J, Hauke V, Adam P, Wehrung P, Trendel JM, Albrecht P, Dessort D, Connan J (1994) Novel optically active hydrocarbons in sediments: evidence for an extended biological cyclization of higher regular polyprenols. Angew Chem Int Engl 33: 1166–1169 (1994)
Schink B (1992) Syntrophism among prokaryotes. In: Balows A, Trüper HG, Dworkin M, Harder W, Schleifer K-H (eds) The prokaryotes. Springer, Berlin Heidelberg New York, pp 276–299
Schmidt K (1978) Biosynthesis of carotenoids In: Clayton RK, Sistrom WR (eds) The photosynthetic bacteria. Plenum, New York, pp 729–750
Shapiro RH (1963) In: Djerassi C (ed) Steroid reactions. Holden-Day, San Francisco, pp 371–402
Shiojima K, Arai Y, Masuda K, Takase Y, Ageta T, Ageta H (1992) Mass spectra of pentacyclic triterpenoids. Chem Pharm Bull 40: 1683–1690
Sih CJ, Wang KC, Tai HH (1968) Mechanisms of steroid oxidation by microorganisms: XIII. C22 acid intermediates in the degradation of the cholesterol side chain. Biochemistry 7: 796–807
Simoneit BTR (1977) Diterpenoid compounds and other lipids in deep-sea sediments and their geochemical significance. Geochim Cosmochim Acta 41: 463–476
Simoneit BTR, Grimalt JO, Wang TG, Cox RE, Hatcher PG, Nissenbaum A (1985) Cyclic terpenoids of contemporary resinous plant detritus and of fossil woods, ambers and coals. Org Geochem 10: 877–889
Simoneit BTR, Mazurek MA (1982) Organic matter of the troposphere: II. Natural background of biogenic lipid matter in aerosols over the rural western United States. Atmos Environ 16: 2139–2159
Smith GW (1975) The crystal and molecular structure of 22,29,30-trisnorhopane II, C27H46. Acta Cryst B 31: 522–526
Smith KE, Latif S, Kirk DN, White KA (1988) Microbial transformations of steroids: I. Rare transformations of progesterone by Apiocrea chrysosperma. J Steroid Biochem 31, 83–89
Steadman BL, Farag AM, Bergman HL (1991) Exposure-related patterns of biochemical indicators in rainbow trout exposed to no 2 fuel oil. Environ Toxicol Chem 10: 365–374
Stoudt TH, McAleer WJ, Koslowski MA, Marlatt V (1958) The microbial dehydrogenation of some pregnanes and allopregnanes to 1,4-pregnadienes. Arch Biochem Biophys 74: 280–281
Summons RE, Powell TG (1987) Identification of aryl isoprenoids in source rocks and crude oils: biological markers for the green sulfur bacteria. Geochim Cosmochim Acta 51: 557–566
Sundström G, Larsson A, Tarkpea M (1986) Creosote. In: Hutzinger O (ed) The handbook of environmental chemistry, vol 3, part D. Springer, Berlin Heidelberg New York, pp 159–205
Tan YL, Heit M (1981) Biogenic and abiogenic polynuclear hydrocarbons in sediments from two remote Adirondack lakes. Geochim Cosmochim Acta 45: 2267–2279
Taylor DG, Trudgill PW (1978) Metabolism of cyclohexane carboxylic acid by Alcaligenes strain WI. J Bacteriol 134: 401–411
ten Haven HL, Peakman TM, Rullkötter J (1992) A2-Triterpenes, early intermediates in the diagenesis of terrigenous triterpenoids. Geochim Cosmochim Acta 56: 1993–2000
ten Haven HL, Peakman TM, Rullkötter J (1992) Early diagenetic transformation of higher-plant triterpenoids in deep-sea sediments from Baffin Bay. Geochim Cosmochim Acta 56: 2001–2024
Tezuka Y, Kikuchi T, Dhanabalasingha B, Karunaratne V, Gunatilaka AAL (1994) Studies on terpenoids and steroids: 25. Complete ’H- and 13C-NMR spectral assignments of salaciquinone, a new 7-oxo-quinonemethide dinortriterpenoid. J Nat Prod 57: 270–276
Thomson RH (ed.) The chemistry of natural products. Blackie, Glasgow
Trendel JM, Guilhem J, Crisp P, Repeta D, Connon J, Alprecht P (1990) Identification of two demethylated C28 hopanes in biodegraded petroleum. J Chem Soc Chem Comm 424–425
Trendel JM, Lohmann F, Kintzinger JP, Albrecht P, Chiaroni A, Riche C, Cesario M, Guilhem J, Pascard C (1989) Identification of des-A-triterpenoid hydrocarbons occurring in surface sediments. Tetrahedron 45: 4457–4460
Trudgill PW (1984) Microbial degradation of the alicyclic ring: structural relationships and metabolic pathways. In: Gibson DT (ed) Microbial degradation of organic compounds. Marcel Dekker, New York, pp 131–180
Tsuda K, Nozoe S, Okada Y (1963) An aromatization reaction of a cross-conjugated dienone system with zinc: IV. Synthesis of 11-hydroxyisoequilin and aromatization of the steroid 1,4,8-triene-3,11-dione system. J Org Chem 28: 789–792
Tsuda K, Ohki E, Nozoe S (1963) An aromatization reaction of a cross-conjugated dienone system with zinc: II. Aromatization of steroidal 1,4-dien-3-one and 1,4,6-trien3-one system with zinc. J Org Chem 28: 783–785
Ulubelen A, Topcu G (1992) New abietane diterpenoids from Salvia montbretii. J Nat Prod 55: 441–444
Van Kaam-Peters HME, Köster J, De Leeuw JW, Sinninghe Damsté JS (1995) Occurrence of two novel benzothiophene hopanoid families in sediments. Org Geochem 27: 607616
Varanasi U, Stein JE, Nishimoto M, Reichert WL, Collier TK (1987) Chemical carcinogenesis in feral fish: uptake, activation, and detoxication of organic xenobiotics. Environ Health Perspect 71: 155–170
Wakeham SG, Schaffner C, Giger W (1980) Polycyclic aromatic hydrocarbons in recent lake sediments: I. Compounds having anthropogenic origins. Geochim Cosmochim Acta 44: 415–429
Wakeham SG, Schaffner C, Giger W (1980) Polycyclic aromatic hydrocarbons in recent lake sediments: II. Compounds derived from biogenic precursors during early diagenesis. Geochim Cosmochim Acta 44: 415–429
Wang KC, You B-J, Yan J-L, Lee S-S (1995) Microbial transformation of lanosterol derivatives with Mycobacterium sp. (NRLL B-3805). J Nat Prod 58: 1222–1227
Wang T-G, Simoneit BRT (1991). Organic geochemistry and coal petrology of tertiary brown coal in the Zhoujing mine, Baise Basin, South China: 3. Characteristics of poly-cyclic aromatic hydrocarbons. Fuel 70: 819–829
Wang Z, Fingas M, Sergy G (1994) Study of 22-year old Arrow oil samples using bio-marker compounds by GC/MS. Environ Sci Technol 28: 1733–1746
Wang, Z, Fingas M, Li K (1994) Fractionation of a light crude oil and identification and quantification of aliphatic, aromatic and biomarker compounds by GC-FID and GC-MS: II. J Chromatogr Sci 32: 367–382
Wei H, Songian L (1989) A new maturity parameter based on monoaromatic hopanoids. Org Geochem 16: 1007–1013
Weng C, Gordon MH (1992) Antioxidant activity of quinones extracted from tanshen (Salvia miltiorrhiza Bunge). J Agric Food Chem 40: 1331–1336
Wenkert E, Fuchs A, McChesney JD (1965) Chemical artifacts from the family Labiatae. J Org Chem 30: 2931–2934
Windsor JG, Hites RA (1979) Polycyclic aromatic hydrocarbons in Gulf of Maine sediments and Nova Scotia soils. Geochim Cosmochim Acta 43: 27–33
Wolff, GA, Trendel JM, Albrecht P (1989) Novel monoaromatic triterpenoid hydrocarbons occurring in sediments. Tetrahedron 45: 6721–6728
Yunker MB, Macdonald RW (1995) Composition and origins of polycyclic aromatic hydrocarbons in the Mackenzie River and on the Beaufort Sea Shelf. Arctic 48: 118–129
Zderic JA, Carpino H, Bowers A, Djerassi C (1963) Steroids: CCXXVIII. The synthesis of equilin Steroids 1: 233–249
Zeman EJ (1994) Complex organic molecules found in interplanetary dust particles. Physics Today 47 (3): 17–19
Zheng J, Nicholson RA (1996) Influence of two naturally occurring abietane monocarboxylic acids (resin acids) and a chlorinated derivative on release of the inhibitiory neurotransmitter y-aminobutyric acid from trout brain synaptosomes. Bull Environ Contam Toxicol 56: 114–120
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Neilson, A.H., Hynning, PÅ. (1998). PAHs: Products of Chemical and Biochemical Transformation of Alicyclic Precursors. In: Neilson, A.H. (eds) PAHs and Related Compounds. The Handbook of Environmental Chemistry, vol 3 / 3I. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-49697-7_6
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