The Hopanoids: palaeochemistry and biochemistry of a group of natural products

Ourisson, Guy; Albrecht, Pierre; Rohmer, Michel

doi:10.1351/pac197951040709

Cited by 760 publications

(239 citation statements)

References 9 publications

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“…3) with a low OEP (Table 2) in the samples, particularly n-C 15 , n-C 17 , and n-C 19 in the Ordovician samples, and existence of trace amounts of n-alkylcyclochexanes with a slight odd-over-even predominance around C 17 alkylcyclohexane (Douglas et al, 1991;Fowler, 1992;Fowler et al, 1986) are characteristic features of organic matter derived from Gloeocapsomorpha prisca algae (Hoffmann et al, 1987;Peters et al, 2005;Reed et al, 1986). Bacteriohopanepolyols, which are bacterial membrane lipids, have been considered as the precursor of hopanoid biomarkers (Ourisson and Albrecht, 1992;Ourisson et al, 1979;Ourisson and Rohmer, 1992), consistent with the high relative abundance of homohopanes (C 31 -C 34 ) in all samples (Fig. 4), particularly in the Silurian samples (Peters and Moldowan, 1991).…”

Section: Origin Of Organic Mattermentioning

confidence: 99%

Organic geochemical characteristics of black shales across the Ordovician–Silurian boundary in the Holy Cross Mountains, central Poland

Mustafa

Sephton

Watson

et al. 2015

Marine and Petroleum Geology

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Black shales in the Holy Cross Mountains area of Poland provide a record of environmental change across the Ordovician-Silurian boundary. The changing depositional conditions have generated a variation in organic matter contents above and below the boundary. Investigating the organic constitution of these black shales has the potential to reveal how their organic matter contents were generated and how suitable these rocks and their lateral equivalents may be for exploitation as shale and Silurian rocks, these rocks were buried and subjected to thermal maturation. Rock Eval and Mustafa, K.A., Sephton M.A., Spathopoulos, F., Watson, J.S., Krzywiec, P. Organic geochemical characteristics of black shales across the Ordovician-Silurian boundary in the Holy Cross Mountains, Central Poland, Marine and Petroleum Geology, doi:10.1016/j.marpetgeo.2015.08.018. 2 biomarker thermal maturity parameters all indicate that the organic matter is mature and lies within the oil window. The Ordovician and Silurian shales have direct relevance to recent attempts to discover and exploit shale gas reservoirs in Poland. Our data and interpretations suggest that the relatively low TOC values (<2%) and low maturities for gas generation render these rocks unsuitable for commercial shale gas production. The progressive improvement in conditions for preserving organic matter across the Ordovician-Silurian boundary does, however, leave the possibility that more suitable deposits occur in Early Silurian rocks in other parts of the basin.

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Section: Origin Of Organic Mattermentioning

confidence: 99%

Organic geochemical characteristics of black shales across the Ordovician–Silurian boundary in the Holy Cross Mountains, central Poland

Mustafa

Sephton

Watson

et al. 2015

Marine and Petroleum Geology

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“…The initial biomarkers attributable to bacteria are the hopane series Ourisson, Albrecht, & Rohmer, 1979, 1982Kajukova et al, 1981). The 17a(H),21b(H)-hopanes (VIII) that range from C 27 to C 35 (no C 28 ) were encountered in numerous ancient sediments and petroleums, and diagenesis and maturation of the microbial precursors (e.g., bacteriohopanepolyol, IX, and diploptene, X, Fig.…”

Section: Microbial Biomarkersmentioning

confidence: 99%

“…Microbiota, i.e., bacteria and archaea, are also the major contributors to the biomarker record of the early Earth (Brocks et al, 1999;Summons et al, 1999). The isoprenoids and hopanoids are the most extensively documented alkyl and cyclic biomarkers for bacteria (Ourisson, Albrecht, & Rohmer, 1979;Summons & Jahnke, 1990;Jahnke et al, 1992Jahnke et al, , 1999Ourisson & Rohmer, 1992;Rohmer, 1993;Kates, 1997). It is important to note that a single natural product precursor (phytol in Fig.…”

Section: Biomarkers Of Past Microbial Ecosystemsmentioning

confidence: 99%

A review of current applications of mass spectrometry for biomarker/molecular tracer elucidations

Simoneit

2004

Mass Spectrometry Reviews

130

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Mass spectrometry, especially coupled with gas chromatography or tandem, is the analytical method of choice in elucidations of biomarker compounds present in organic mixtures extracted from geological, environmental, or biological samples. This review describes the biomarker concept; i.e., the precursor natural products to the geological/environmental derivatives, and their application as tracers in the geosphere and ambient environment. The mass spectrometric methods currently utilized for such analyses are reviewed, and typical examples of applications are described with a general key to the literature. © 2004 Wiley Periodicals, Inc., Mass Spec Rev 24:719–765, 2005

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“…Hopanoids are a distinctive class of pentacyclic triterpenoid lipids with wide ranging biogeochemical utility (Ourisson et al, 1979;Rohmer et al, 1984;Brocks et al, 2003). They are biosynthesized primarily by bacteria via cyclization of squalene to yield the C 30 hydrocarbon, diploptene [hop-22(29)-ene;Ochs et al, 1992;Wendt et al, 1997Wendt et al, ,1999.…”

Section: Introductionmentioning

confidence: 99%

“…The tetrahydroxy compound bacteriohopanetetrol (BHtetrol) is generally the most abundant triterpenoid in many species. During diagenesis, BHPs are reduced and defunctionalized to yield a regular series of hopanes, commonly ranging from C 28 to C 35 , more rarely to higher carbon numbers, and with systematic stereochemical variation (Ourisson et al, 1979;Ourisson and Albrecht, 1992).…”

Section: Introductionmentioning

confidence: 99%

Identification and quantification of polyfunctionalized hopanoids by high temperature gas chromatography–mass spectrometry

Sessions

Zhang

Welander

et al. 2013

Organic Geochemistry

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Hopanoids are triterpenoids produced mainly by bacteria, are ubiquitous in the environment, and have many important applications as biological markers. A wide variety of related hopanoid structures exists, many of which are polyfunctionalized. These modifications render the hopanoids too involatile for conventional gas chromatography (GC) separation, so require either laborious oxidative cleavage of the functional groups or specialized high temperature (HT) columns. Here we describe the systematic evaluation and optimization of a HT-GC method for the analysis of polyfunctionalized hopanoids and their methylated homologs. Total lipid extracts are derivatized with acetic anhydride and no further treatment or workup is required. We show that acid or base hydrolysis to remove di-and triacylglycerides leads to degradation of several BHP structures. DB-XLB type columns can elute hopanoids up to bacteriohopane-tetrol at 350 °C, with baseline separation of all 2-methyl/desmethyl homologs. DB-5HT type columns can additionally elute bacteriohopaneaminotriol and bacteriohopaneaminotetrol, but do not fully separate 2-methyl/ desmethyl homologs. The method gave 2-to 7-fold higher recovery of hopanoids than oxidative cleavage and can provide accurate quantification of all analytes including 2-methyl hopanoids. By comparing data from mass spectra with those from a flame ionization detector, we show that the mass spectromet (MS) response factors for different hopanoids using either total ion counts or m/z 191 vary substantially. Similarly, 2-methyl ratios estimated from selected-ion data are lower than those from FID by 10-30% for most hopanoids, but higher by ca. 10% for bacteriohopanetetrol. Mass spectra for a broad suite of hopanoids, including 2-methyl homologs, from Rhodopseudomonas palustris are presented, together with the tentative assignment of several new hopanoid degradation products.

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The Hopanoids: palaeochemistry and biochemistry of a group of natural products

Abstract: More than 100 individual derivatives of hopane have been isolated from sedim~ntary organic matter of most varied origin.

Cited by 760 publications

References 9 publications

Organic geochemical characteristics of black shales across the Ordovician–Silurian boundary in the Holy Cross Mountains, central Poland

Organic geochemical characteristics of black shales across the Ordovician–Silurian boundary in the Holy Cross Mountains, central Poland

A review of current applications of mass spectrometry for biomarker/molecular tracer elucidations

Identification and quantification of polyfunctionalized hopanoids by high temperature gas chromatography–mass spectrometry

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