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Pure Appl. Chem., 1993, Vol. 65, No. 6, pp. 1293-1298

http://dx.doi.org/10.1351/pac199365061293

The biosynthesis of triterpenoids of the hopane series in the Eubacteria: A mine of new enzymatic reactions

M. Rohmer

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  • Guan Hongxiang, Sun Yongge, Mao Shengyi, Zhu Xiaowei, Wu Nengyou: Molecular and stable carbon isotopic compositions of hopanoids in seep carbonates from the South China Sea continental slope. Journal of Asian Earth Sciences 2013. <http://dx.doi.org/10.1016/j.jseaes.2013.10.026>
  • Doğrul Selver Ayça, Talbot Helen M., Gustafsson Örjan, Boult Stephen, van Dongen Bart E.: Soil organic matter transport along an sub-Arctic river–sea transect. Organic Geochemistry 2012, 51, 63. <http://dx.doi.org/10.1016/j.orggeochem.2012.08.002>
  • WELANDER P. V., DOUGHTY D. M., WU C.-H., MEHAY S., SUMMONS R. E., NEWMAN D. K.: Identification and characterization of Rhodopseudomonas palustris TIE-1 hopanoid biosynthesis mutants : Hopanoid biosynthesis in R. palustris TIE-1. Geobiol 2012, 10, 163. <http://dx.doi.org/10.1111/j.1472-4669.2011.00314.x>
  • Řezanka Tomáš, Siristova Lucie, Melzoch Karel, Sigler Karel: N-Acylated Bacteriohopanehexol-Mannosamides from the Thermophilic Bacterium Alicyclobacillus acidoterrestris . Lipid 2011, 46, 249. <http://dx.doi.org/10.1007/s11745-010-3482-4>
  • Kim Jung-Hyun, Talbot Helen M., Zarzycka Barbara, Bauersachs Thorsten, Wagner Thomas: Occurrence and abundance of soil-specific bacterial membrane lipid markers in the Têt watershed (southern France): Soil-specific BHPs and branched GDGTs. Geochem. Geophys. Geosyst. 2011, 12, n/a. <http://dx.doi.org/10.1029/2010GC003364>
  • ROHMER M.: ChemInform Abstract: The Biosynthesis of Triterpenoids of the Hopane Series in the Eubacteria: A Mine of New Enzyme Reactions. ChemInform 2010, 24, no. <http://dx.doi.org/10.1002/chin.199336324>
  • Handley Luke, Talbot Helen M., Cooke Martin P., Anderson Kathleen E., Wagner Thomas: Bacteriohopanepolyols as tracers for continental and marine organic matter supply and phases of enhanced nitrogen cycling on the late Quaternary Congo deep sea fan. Geochem 2010, 41, 910. <http://dx.doi.org/10.1016/j.orggeochem.2010.04.016>
  • Rethemeyer Janet, Schubotz Florence, Talbot Helen M., Cooke Martin P., Hinrichs Kai-Uwe, Mollenhauer Gesine: Distribution of polar membrane lipids in permafrost soils and sediments of a small high Arctic catchment. Geochem 2010, 41, 1130. <http://dx.doi.org/10.1016/j.orggeochem.2010.06.004>
  • Tyler J., Kashiyama Y., Ohkouchi N., Ogawa N., Yokoyama Y., Chikaraishi Y., Staff R. A., Ikehara M., Bronk Ramsey C., Bryant C.: Tracking aquatic change using chlorine-specific carbon and nitrogen isotopes: The last glacial-interglacial transition at Lake Suigetsu, Japan. Geochem Geophys Geosyst 2010, 11, Q09010. <http://dx.doi.org/10.1029/2010GC003186>
  • Xu Yunping, Cooke Martin P., Talbot Helen M., Simpson Myrna J.: Bacteriohopanepolyol signatures of bacterial populations in Western Canadian soils. Geochem 2009, 40, 79. <http://dx.doi.org/10.1016/j.orggeochem.2008.09.003>
  • Cooke Martin P., van Dongen Bart E., Talbot Helen M., Semiletov Igor, Shakhova Natalia, Guo Laodong, Gustafsson Örjan: Bacteriohopanepolyol biomarker composition of organic matter exported to the Arctic Ocean by seven of the major Arctic rivers. Geochem 2009, 40, 1151. <http://dx.doi.org/10.1016/j.orggeochem.2009.07.014>
  • DOUGHTY D. M., HUNTER R. C., SUMMONS R. E., NEWMAN D. K.: 2-Methylhopanoids are maximally produced in akinetes of Nostoc punctiforme: geobiological implications. Geobiology 2009, 7, 524. <http://dx.doi.org/10.1111/j.1472-4669.2009.00217.x>
  • Rohmer Michel: From Molecular Fossils of Bacterial Hopanoids to the Formation of Isoprene Units: Discovery and Elucidation of the Methylerythritol Phosphate Pathway. Lipid 2008, 43, 1095. <http://dx.doi.org/10.1007/s11745-008-3261-7>
  • Talbot Helen M., Summons Roger E., Jahnke Linda L., Cockell Charles S., Rohmer Michel, Farrimond Paul: Cyanobacterial bacteriohopanepolyol signatures from cultures and natural environmental settings. Geochem 2008, 39, 232. <http://dx.doi.org/10.1016/j.orggeochem.2007.08.006>
  • Ohkouchi Naohiko, Nakajima Yoji, Ogawa Nanako O., Chikaraishi Yoshito, Suga Hisami, Sakai Saburo, Kitazato Hiroshi: Carbon isotopic composition of the tetrapyrrole nucleus in chloropigments from a saline meromictic lake: A mechanistic view for interpreting the isotopic signature of alkyl porphyrins in geological samples. Geochem 2008, 39, 521. <http://dx.doi.org/10.1016/j.orggeochem.2007.11.002>
  • Talbot Helen M., Coolen Marco J.L., Damsté Jaap S. Sinninghe: An unusual 17α,21β(H)-bacteriohopanetetrol in Holocene sediments from Ace Lake (Antarctica). Geochem 2008, 39, 1029. <http://dx.doi.org/10.1016/j.orggeochem.2008.01.008>
  • Cooke Martin P., Talbot Helen M., Wagner Thomas: Tracking soil organic carbon transport to continental margin sediments using soil-specific hopanoid biomarkers: A case study from the Congo fan (ODP site 1075). Geochem 2008, 39, 965. <http://dx.doi.org/10.1016/j.orggeochem.2008.03.009>
  • Gibson Robert A., Talbot Helen M., Kaur Gurpreet, Pancost Richard D., Mountain Bruce: Bacteriohopanepolyol signatures of cyanobacterial and methanotrophic bacterial populations recorded in a geothermal vent sinter. Geochem 2008, 39, 1020. <http://dx.doi.org/10.1016/j.orggeochem.2008.04.014>
  • Cooke Martin P., Talbot Helen M., Farrimond Paul: Bacterial populations recorded in bacteriohopanepolyol distributions in soils from Northern England. Geochem 2008, 39, 1347. <http://dx.doi.org/10.1016/j.orggeochem.2008.05.003>
  • Sakata Susumu, Hayes John M., Rohmer Michel, Hooper Alan B., Seemann Myriam: Stable carbon-isotopic compositions of lipids isolated from the ammonia-oxidizing chemoautotroph Nitrosomonas europaea. Geochem 2008, 39, 1725. <http://dx.doi.org/10.1016/j.orggeochem.2008.08.005>
  • Pan Weidong, Vincent Stéphane P.: Synthesis of a deuterated analogue of bacteriohopanetetrol–glucosamine, a probe of complex hopanoid biosynthesis. Org Biomol Chem 2008, 6, 2394. <http://dx.doi.org/10.1039/b803365j>
  • Coolen Marco J. L., Talbot Helen M., Abbas Ben A., Ward Christopher, Schouten Stefan, Volkman John K., Damsté Jaap S. Sinninghe: Sources for sedimentary bacteriohopanepolyols as revealed by 16S rDNA stratigraphy. Environ Microbiol 2008, 10, 1783. <http://dx.doi.org/10.1111/j.1462-2920.2008.01601.x>
  • Pan Weidong, Zhang Yongmin, Liang Guangyi, Rohmer Michel, Sinaÿ Pierre, Vincent Stéphane P.: Diastereoselective Synthesis of Aminobacteriohopanetetrol, a Biomarker for Methanotrophic Bacteria: Confirmation of the Absolute Configuration. C&B 2007, 4, 2182. <http://dx.doi.org/10.1002/cbdv.200790175>
  • Pan Weidong, Sun Chao, Zhang Yongmin, Liang Guangyi, Sinaÿ Pierre, Vincent Stéphane P.: Complex Biohopanoids Synthesis: Efficient Anchoring of Ribosyl Subunits onto a C30 Hopane. Chem Eur J 2007, 13, 1471. <http://dx.doi.org/10.1002/chem.200600659>
  • Medeiros Patricia M., Simoneit Bernd R. T.: Gas chromatography coupled to mass spectrometry for analyses of organic compounds and biomarkers as tracers for geological, environmental, and forensic research. J Sep Science 2007, 30, 1516. <http://dx.doi.org/10.1002/jssc.200600399>
  • Talbot Helen M., Rohmer Michel, Farrimond Paul: Rapid structural elucidation of composite bacterial hopanoids by atmospheric pressure chemical ionisation liquid chromatography/ion trap mass spectrometry. Rapid Commun Mass Spectrom 2007, 21, 880. <http://dx.doi.org/10.1002/rcm.2911>
  • Talbot Helen M., Farrimond Paul: Bacterial populations recorded in diverse sedimentary biohopanoid distributions. Geochem 2007, 38, 1212. <http://dx.doi.org/10.1016/j.orggeochem.2007.04.006>
  • Saito Hiroyuki, Suzuki Noriyuki: Distributions and sources of hopanes, hopanoic acids and hopanols in Miocene to recent sediments from ODP Leg 190, Nankai Trough. Geochem 2007, 38, 1715. <http://dx.doi.org/10.1016/j.orggeochem.2007.05.012>
  • Zhang Chuanlun L., Huang Zhiyong, Li Yi-Liang, Romanek Christopher S., Mills Gary L., Gibson Robert A., Talbot Helen M., Wiegel Juergen, Noakes John, Culp Randy: Lipid Biomarkers, Carbon Isotopes, and Phylogenetic Characterization of Bacteria in California and Nevada Hot Springs. Geomicrobiology J 2007, 24, 519. <http://dx.doi.org/10.1080/01490450701572515>
  • Ershov Yu. V.: 2-C-methylerythritol phosphate pathway of isoprenoid biosynthesis as a target in identifying new antibiotics, herbicides, and immunomodulators: A review. Appl Biochem Microbiol 2007, 43, 115. <http://dx.doi.org/10.1134/S0003683807020019>
  • Bowden Stephen A., Farrimond Paul, Snape Colin E., Love Gordon D.: Compositional differences in biomarker constituents of the hydrocarbon, resin, asphaltene and kerogen fractions: An example from the Jet Rock (Yorkshire, UK). Geochem 2006, 37, 369. <http://dx.doi.org/10.1016/j.orggeochem.2005.08.024>
  • Simoneit Bernd R.T.: A review of current applications of mass spectrometry for biomarker/molecular tracer elucidations. Mass Spectrom Rev 2005, 24, 719. <http://dx.doi.org/10.1002/mas.20036>
  • Bednarczyk Audrey, Hernandez Teresita Carrillo, Schaeffer Philippe, Adam Pierre, Talbot Helen M., Farrimond Paul, Riboulleau Armelle, Largeau Claude, Derenne Sylvie, Rohmer Michel: 32,35-Anhydrobacteriohopanetetrol: an unusual bacteriohopanepolyol widespread in recent and past environments. Geochem 2005, 36, 673. <http://dx.doi.org/10.1016/j.orggeochem.2004.10.014>
  • Talbot Helen M., Farrimond Paul, Schaeffer Philippe, Pancost Richard D.: Bacteriohopanepolyols in hydrothermal vent biogenic silicates. Geochem 2005, 36, 663. <http://dx.doi.org/10.1016/j.orggeochem.2004.10.015>
  • Sugden Mark A., Talbot Helen M., Farrimond Paul: Flash pyrolysis – a rapid method for screening bacterial species for the presence of bacteriohopanepolyols. Geochem 2005, 36, 975. <http://dx.doi.org/10.1016/j.orggeochem.2004.12.003>
  • Dumitrescu Mirela, Brassell Simon C.: Biogeochemical assessment of sources of organic matter and paleoproductivity during the early Aptian Oceanic Anoxic Event at Shatsky Rise, ODP Leg 198. Geochem 2005, 36, 1002. <http://dx.doi.org/10.1016/j.orggeochem.2005.03.001>
  • Pancost Richard D., Zhang Chuanlun L., Tavacoli Joe, Talbot Helen M., Farrimond Paul, Schouten Stefan, Sinninghe Damsté Jaap S., Sassen Roger: Lipid biomarkers preserved in hydrate-associated authigenic carbonate rocks of the Gulf of Mexico. Palaeogeography Palaeoclimatol Palaeoecol 2005, 227, 48. <http://dx.doi.org/10.1016/j.palaeo.2005.04.035>
  • Fouchard Samuel, Llopiz Pierre, Neunlist Serge, Joyeux Cécile: Influence of the temperature and the growth phase on the hopanoids and fatty acids content of Frateuria aurantia (DSMZ 6220). FEMS Microbiological Ecology 2004, 47, 371. <http://dx.doi.org/10.1016/S0168-6496(03)00302-7>
  • Fuhrmann A., Horsfield B., Lopez J. F., Hu Liguo, Zhang Zhanwen: ORGANIC FACIES, DEPOSITIONAL ENVIRONMENT AND PETROLEUM GENERATING CHARACTERISTICS OF THE LACUSTRINE SHAHEJIE FORMATION, ES4 MEMBER, WESTERN DEPRESSION, LIAOHE BASIN (NE CHINA). JPG 2004, 27, 27. <http://dx.doi.org/10.1111/j.1747-5457.2004.tb00043.x>
  • Talbot Helen M., Summons Roger, Jahnke Linda, Farrimond Paul: Characteristic fragmentation of bacteriohopanepolyols during atmospheric pressure chemical ionisation liquid chromatography/ion trap mass spectrometry. Rapid Commun Mass Spectrom 2003, 17, 2788. <http://dx.doi.org/10.1002/rcm.1265>
  • Talbot Helen M., Squier Angela H., Keely Brendan J., Farrimond Paul: Atmospheric pressure chemical ionisation reversed-phase liquid chromatography/ion trap mass spectrometry of intact bacteriohopanepolyols. Rapid Commun Mass Spectrom 2003, 17, 728. <http://dx.doi.org/10.1002/rcm.974>
  • Pancost Richard D, Sinninghe Damsté Jaap S: Carbon isotopic compositions of prokaryotic lipids as tracers of carbon cycling in diverse settings. Chem Geol 2003, 195, 29. <http://dx.doi.org/10.1016/S0009-2541(02)00387-X>
  • Talbot Helen M., Watson Diane F., Pearson Emma J., Farrimond Paul: Diverse biohopanoid compositions of non-marine sediments. Geochem 2003, 34, 1353. <http://dx.doi.org/10.1016/S0146-6380(03)00159-1>
  • Costantino Valeria, Fattorusso Ernesto, Imperatore Concetta, Mangoni Alfonso: A biosynthetically significant new bacteriohopanoid present in large amounts in the Caribbean sponge Plakortis simplex. Tetrahedron 2001, 57, 4045. <http://dx.doi.org/10.1016/S0040-4020(01)00286-1>
  • Bravo Jean-Michel, Perzl Michael, Härtner Thomas, Kannenberg Elmar L., Rohmer Michel: Novel methylated triterpenoids of the gammacerane series from the nitrogen-fixing bacterium Bradyrhizobium japonicum USDA 110. European Journal of Biochemistry 2001, 268, 1323. <http://dx.doi.org/10.1046/j.1432-1327.2001.01998.x>
  • Rosa-Putra Surya, Nalin Renaud, Domenach Anne-Marie, Rohmer Michel: Novel hopanoids from Frankia spp. and related soil bacteria. European Journal of Biochemistry 2001, 268, 4300. <http://dx.doi.org/10.1046/j.1432-1327.2001.02348.x>
  • Douka Eugenia, Koukkou Anna-Irini, Drainas Constantin, Grosdemange-Billiard Catherine, Rohmer Michel: Structural diversity of the triterpenic hydrocarbons from the bacterium Zymomonas mobilis: the signature of defective squalene cyclization by the squalene/hopene cyclase. FEMS Microbiol Lett 2001, 199, 247. <http://dx.doi.org/10.1111/j.1574-6968.2001.tb10682.x>
  • Sharkey Thomas D, Yeh Sansun: ISOPRENE EMISSION FROM PLANTS. annu rev plant physiol plant mol biol 2001, 52, 407. <http://dx.doi.org/10.1146/annurev.arplant.52.1.407>
  • Farrimond P, Head I.M, Innes H.E: Environmental influence on the biohopanoid composition of recent sediments. Geochimica et Cosmochimica Acta 2000, 64, 2985. <http://dx.doi.org/10.1016/S0016-7037(00)00404-X>
  • Watson D.F, Farrimond P: Novel polyfunctionalised geohopanoids in a recent lacustrine sediment (Priest Pot, UK). Geochem 2000, 31, 1247. <http://dx.doi.org/10.1016/S0146-6380(00)00148-0>
  • Duvold Tore, Rohmer Michel: Synthesis of ribosylhopane, the putative biosynthetic precursor of bacterial triterpenoids of the hopane series. Tetrahedron 1999, 55, 9847. <http://dx.doi.org/10.1016/S0040-4020(99)00567-0>
  • Seemann Myriam, Bisseret Philippe, Tritz Jean-Philippe, Hooper Alan B., Rohmer Michel: Novel bacterial triterpenoids of the hopane series from Nitrosomonas europaea and their significance for the formation of the C35 bacteriohopane skeleton. Tetrahetron Lett 1999, 40, 1681. <http://dx.doi.org/10.1016/S0040-4039(99)00064-7>
  • Charon Lionel, Pale-Grosdemange Catherine, Rohmer Michel: On the reduction steps in the mevalonate independent 2-C-methyl-d-erythritol 4-phosphate (MEP) pathway for isoprenoid biosynthesis in the bacterium Zymomonas mobilis. Tetrahetron Lett 1999, 40, 7231. <http://dx.doi.org/10.1016/S0040-4039(99)01531-2>
  • Rodier C, Llopiz P, Neunlist S: C32 and C34 hopanoids in recent sediments of European lakes: novel intermediates in the early diagenesis of biohopanoids. Geochem 1999, 30, 713. <http://dx.doi.org/10.1016/S0146-6380(99)00045-5>
  • Innes Helen E., Bishop Andrew N., Fox Paul A., Head Ian M., Farrimond Paul: Early diagenesis of bacteriohopanoids in Recent sediments of Lake Pollen, Norway. Geochem 1998, 29, 1285. <http://dx.doi.org/10.1016/S0146-6380(98)00108-9>
  • D. Brown Geoffrey: The biosynthesis of steroids and triterpenoids. Nat Prod Rep 1998, 15, 653. <http://dx.doi.org/10.1039/a815653y>
  • Sakata Susumu, Hayes John M., McTaggart Andrew R., Evans Ronald A., Leckrone Kristen J., Togasaki Robert K.: Carbon isotopic fractionation associated with lipid biosynthesis by a cyanobacterium: Relevance for interpretation of biomarker records. Geochimica et Cosmochimica Acta 1997, 61, 5379. <http://dx.doi.org/10.1016/S0016-7037(97)00314-1>
  • Mahato Shashi B., Sen Sucharita: Advances in triterpenoid research, 1990–1994. Phytochemisry 1997, 44, 1185. <http://dx.doi.org/10.1016/S0031-9422(96)00639-5>
  • Innes Helen E., Bishop Andrew N., Head Ian M., Farrimond Paul: Preservation and diagenesis of hopanoids in Recent lacustrine sediments of Priest Pot, England. Geochem 1997, 26, 565. <http://dx.doi.org/10.1016/S0146-6380(97)00017-X>
  • Zhao Ning, Berova Nina, Nakanishi Koji, Rohmer Michel, Mougenot Pascale, Jürgens Uwe J.: Structures of two bacteriohopanoids with acyclic pentol side-chains from the cyanobacterium Nostoc PCC 6720. Tetrahedron 1996, 52, 2777. <http://dx.doi.org/10.1016/0040-4020(96)00013-0>
  • Herrmann Dominique, Bisseret Philippe, Connan Jacques, Rohmer Michel: Relative configurations of carbapseudopentose moieties of hopanoids of the bacterium Zymomonas mobilis and the cyanobacterium ‘Anacystis montana’. Tetrahetron Lett 1996, 37, 1791. <http://dx.doi.org/10.1016/0040-4039(96)00133-5>
  • Simonin Pascale, Jurgens Uwe J., Rohmer Michel: Bacterial Triterpenoids of the Hopane Series from the Prochlorophyte Prochlorothrix Hollandica and their Intracellular Localization. Eur J Biochem 1996, 241, 865. <http://dx.doi.org/10.1111/j.1432-1033.1996.00865.x>
  • Llopiz Pierre, Jürgens Uwe J., Rohmer Michel: Prokaryotic triterpenoids: Bacteriohopanetetrol glycuronosides from the thermophilic cyanobacterium Synechococcus PCC 6907. FEMS Microbiol Lett 1996, 140, 199. <http://dx.doi.org/10.1111/j.1574-6968.1996.tb08336.x>
  • Koukkou Anna I., Drainas Constantin, Rohmer Michel: Towards the characterization of squalene synthase activity in extracts of Zymomonas mobilis. FEMS Microbiol Lett 1996, 140, 277. <http://dx.doi.org/10.1111/j.1574-6968.1996.tb08349.x>
  • Bach Thomas J.: Some new aspects of isoprenoid biosynthesis in plants—A review. Lipid 1995, 30, 191. <http://dx.doi.org/10.1007/BF02537822>
  • Dahl Jeremy, Moldowan J.Michael, Summons Roger E., McCaffrey Mark A., Lipton Paul, Watt D.S., Hope Janet M.: Extended 3β-alkyl steranes and 3-alkyl triaromatic steroids in crude oils and rock extracts. Geochimica et Cosmochimica Acta 1995, 59, 3717. <http://dx.doi.org/10.1016/0016-7037(95)00271-Z>
  • Bisseret Philippe, Seemann Myriam, Rohmer Michel: Dimethyldioxirane oxidation of aminobacteriohopanetriol : Obtention of a putative intermediate in bacterial hopanoid biosynthesis. Tetrahetron Lett 1994, 35, 2687. <http://dx.doi.org/10.1016/S0040-4039(00)77006-7>
  • Ourisson Guy: Pecularities of Sterol Biosynthesis in Plants. J  Plant Physiol 1994, 143, 434. <http://dx.doi.org/10.1016/S0176-1617(11)81803-1>