Structural diversity of the triterpenic hydrocarbons from the bacterium Zymomonas mobilis: the signature of defective squalene cyclization by the squalene/hopene cyclase

Douka, E

doi:10.1016/s0378-1097(01)00190-2

Cited by 6 publications

(10 citation statements)

References 20 publications

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“…Maximal biomass (2.3 g dry cells l 31 ) was reached for growth at 26 ‡C whereas at 16 ‡C it was slightly lower (up to 1.8 g l 31 ). A severe decrease was observed for cultures at 36 ‡C, never reaching more than 0.5 g dry cells l 31 .…”

Section: Growth Phases and Biomassmentioning

confidence: 93%

“…Final temperature was maintained for 20 min. Fatty acid methyl esters were separated on a HP-5 capillary column (0.20 mmU50 m, 0.33 Wm ¢lm thickness) after an initial step of 1 min at 70 ‡C, by a gradient up to 150 ‡C at a rate of 70 ‡C min 31 , followed by a second gradient up to 290 ‡C at a rate of 8 ‡C min 31 . Final temperature was maintained for 1 min.…”

Section: Analyses By Gc and Gc-msmentioning

confidence: 99%

“…The compounds were identi¢ed by GC co-elution with reference samples and comparison of their mass spectra with those of the standards and those described in the literature [28,30]. Analogous compounds were recently found in Zymomonas mobilis [31] and in Frankia sp. [32].…”

Section: Hopanoids Of F Aurantia Dsmz 6220mentioning

confidence: 99%

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Influence of the temperature and the growth phase on the hopanoids and fatty acids content of Frateuria aurantia (DSMZ 6220)

Joyeux¹,

Fouchard²,

Llopiz³

et al. 2004

FEMS Microbiology Ecology

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The main lipids isolated from Frateuria aurantia (DSMZ 6220) are iso-branched fatty acids and triterpenoids of the hopane family like bacteriohopanetetrol and derived hopanoids, beside trace amounts of diploptene and rearranged compounds like fern-7-ene. The impact of the growth temperature and the growth phase in which cells were harvested on this lipid fingerprint was investigated. As expected, an increase of saturated compounds with temperature is the essential modification in the fatty acid composition. The fatty acid composition also varies significantly during the growth. Global lipid fingerprints, including at least PLFA and triterpenoids are suggested to be a tool for measuring the stress state of bacterial cells. Increasing amounts of C-31 hydroxylated hopanoids with a temperature increase is novel information which deserves attention and further investigation for a better comprehension of the physiological significance of modifications conditioned obviously by environmental changes.

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Section: Growth Phases and Biomassmentioning

confidence: 93%

Section: Analyses By Gc and Gc-msmentioning

confidence: 99%

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Influence of the temperature and the growth phase on the hopanoids and fatty acids content of Frateuria aurantia (DSMZ 6220)

Joyeux¹,

Fouchard²,

Llopiz³

et al. 2004

FEMS Microbiology Ecology

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“…The prevalence of hopanes and hopenes over steranes and sterenes indicates some contribution of microbiota as source of organic matter (Peters et al, 2005;Simoneit, 2005;Volkman et al, 1986;Volkman, 2005). The biological sources of the dominant triterpenes in the lobe sediments, hop-17(21)-ene, EE-hopane and diploptene (hop-22(29)-ene) are microorganisms and ferns (Douka et al, 2001;Innes et al, 1997Innes et al, , 1998Pattituci et al, 1995;Rohmer et al, 1984;Rohmer, 1993;Rontani and Volkman 2005;Sinninghe-Damsté et al, 2014;Welander et al, 2010). They are dominant triterpenes in terrestrial environments with low maturity of the organic matter (Garel et al, 2014).…”

Section: Processes Driving the Hopene And Triterpene Spatial And Tempmentioning

confidence: 99%

Aliphatic hydrocarbons and triterpenes of the Congo deep-sea fan

Méjanelle

Rivière

Pinturier

et al. 2017

Deep Sea Research Part II: Topical Studies in Oceanography

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Hydrocarbons were analyzed in sediments from the Congo River deep-sea fan, from the Congo River, and in sinking particles collected by sediment traps 40 m above the sediment. Studied sites encompassed three lobes of decreasing age of formation along the canyon: sites A, F and C and a another lobe system, disconnected from the active channel since 4 ka, Site E. Terrestrial long-chain odd n-alkanes were dominant in all sediments of the lobe system. Unsaturated terpenoids sourced by higher plants, such as gammacerene, lupene, ursene and oleanene, were also detected. At site C, characterized by high accumulation rates (10-20 cm yr−1), the organic matter spends less time in the oxic layer than at other sites and high phytadiene concentrations (10 to 17 μg gOC−1) evidenced recent terrestrial and phytoplanktonic remains reworked in anaerobic conditions. In these sediments, organic carbon-normalized concentrations of terrestrial alkanes and terpenoids were several fold higher than in the lobe sediments with lower accumulation rates (sites A and F), arguing for a more rapid degradation of terrestrial hydrocarbons than bulk organic carbon in the first steps of pre-diagenesis. Ample variations in the contributions of biomarkers from higher plants, ferns, bacteria and angiosperms, indicate an heterogeneous contribution of the soil and vegetation detritus delivered to the Congo lobe sediments. Lower concentrations in terrestrial hydrocarbons at site E, 45 km away from the active canyon, indicated that river particles are still admixed to the dominant marine organic matter. Diploptene and hop-7(21)ene have a dual origin, from terrestrial and marine microorganisms. Scatter in their relationship to gammacerene argues for a contribution of marine microorganisms, in addition to soils-sourced microorganisms. The close distribution patterns of diploptene, hop-21-ene, hop-7(21)ene and neohop-13(18)-ene is in line with the hypothesis of sequential clay-catalyzed isomerisation of bacterial hopenes. Terrestrial biomarker accumulation fluxes at site C are one order of magnitude higher than vertical pelagic flux, demonstrating the magnitude of the inputs delivered through turbiditic transport in the submarine canyon. Crude oil contamination was evidenced at the disconnected site E (UCM, C21 to Please note that this is an author-produced PDF of an article accepted for publication following peer review. The definitive publisher-authenticated version is available on the publisher Web site. C26 tricyclic diterpanes, CPI) and, in smaller amounts, in some sediments from sites A and C. It may be related to marine crude oil extraction and transport. A short-chain mode of alkanes with an even predominance is evidenced in sediments of the lobe complex and likely sources, crude oil, microorganisms and ferns, are discussed.

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“…The wild type SHC from A. acidocaldarius occasionally fails to promote the second anti-Markovnikov cation, resulting in 1% of the natural products having an accidental 6,6,6,5 dammarane-type skeleton (Pale-Gosdemange et al, 1998;Wendt et al, 2000;Rajmani & Gao, 2003). Similar products were observed from Zymomonas mobilis (Douka et al, 2001) and also were attributed to deficient control by the enzyme. Interestingly, Bradyrhizobium japonicum and Rhodopseudomonas palustris produce minor amounts of tetrahymanol in addition to hopanoids (Kleemann et al, 1990;Bravo et al, 2001).…”

Section: Difficult Control and High Mutability Of Anti-markovnikov Camentioning

confidence: 99%

Hypotheses for the origin and early evolution of triterpenoid cyclases

Fischer

Pearson

2007

Geobiology

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Hopanes and steranes are found almost universally in the sedimentary rock record where they often are used as proxies for aerobic organisms, metabolisms, and environments. In order to interpret ancient lipid signatures confidently we require a complementary understanding of how these modern biochemical pathways evolved since their conception. For example, generally it has been assumed that hopanoid biosynthesis was an evolutionary predecessor to steroid biosynthesis. Here we re‐evaluate this assumption. Using a combined phylogenetic and biochemical perspective, we address the evolution of polycyclic triterpenoid biosynthesis and suggest several constraints on using these molecules as aerobic biomarkers. Amino acid sequence data show that the enzymes responsible for polycyclic triterpenoid biosynthesis (i.e. squalene and 2,3‐oxidosqualene cyclases) are homologous. Numerous conserved domains correspond to active sites in the enzymes that are required to complete the complex cyclization reaction. From these sites we develop an evolutionary analysis of three independent characters to explain the evolution of the major classes of polycyclic triterpenoids. These characters are: (i) the number of unfavourable anti‐Markovnikov ring closures, (ii) all‐chair (CCC) or chair‐boat‐chair (CBC) substrate conformation, and (iii) the choice between squalene and 2,3‐oxidosqualene as the substrate. We use these characters to construct four competing phylogenies to describe the evolution of polycyclic triterpenoid biosynthesis. The analysis suggests that malabaricanoids would be the most ancient polycyclic triterpenoids. The two most parsimonious evolutionary trees are the ones in which hopanoid and steroid cyclases diverged from a common ancestor. The transition from a CCC‐ to CBC‐fold marks the major divergence in the evolution of these pathways, and it is diagnosable in the geological record. However, this transition does not require the simultaneous adoption of the aerobic substrate, 2,3‐oxidosqualene, because these characters are controlled by independent parts of the enzyme.

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Structural diversity of the triterpenic hydrocarbons from the bacterium Zymomonas mobilis: the signature of defective squalene cyclization by the squalene/hopene cyclase

Cited by 6 publications

References 20 publications

Influence of the temperature and the growth phase on the hopanoids and fatty acids content of Frateuria aurantia (DSMZ 6220)

Influence of the temperature and the growth phase on the hopanoids and fatty acids content of Frateuria aurantia (DSMZ 6220)

Aliphatic hydrocarbons and triterpenes of the Congo deep-sea fan

Hypotheses for the origin and early evolution of triterpenoid cyclases

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