Uptake of hydrocarbons by the marine diatomCyclotella cryptica

The accumulation of exogenous hydrocarbons by the marine diatomCyclotella cryptica grown in culture has been studied using gas chromatography. Exposure of the alga to paraffins for 10 days results in accumulation of n-alkanes having between C₁₃ and C₁₆ carbon atoms. The C₁₆ level in the accumulated fraction is twice as high as that in the original oil.     

Comparative Characterization of Extracellular and Intracellular Hydrocarbons of Clostridium pasteurianum

Extracellular and intracellular hydrocarbons produced by Clostridium pasteurianum VKM 1774 during cultivation on glucose-containing media in an argon atmosphere or in the presence of carbon dioxide and molecular hydrogen were analyzed by gas-liquid chromatography. Intracellular hydrocarbons were 50-55% (C₂₅-C₃₅) n-alkanes. Carbon dioxide and molecular hydrogen stimulated synthesis of extracellular hydrocarbons, which comprised 90-95% (C₁₁-C₂₄) n-alkanes.     

Alkane assimilation ability of Pseudomonas C12B originally isolated for degradation of alkyl sulfate surfactants

Summary Pseudomonas C12B (NCIMB 11753) is able to utilize a broad range of alkyl sulfates. The growth on n-alkanes of different chain lenght (C₆–C₁₆) was tested. Pseudomonas C12B assimilated hydrocarbons from C₉–C₁₆. Growth rate on n-decane (1%) that was chosen as the typical sole source of carbon and energy depended on oxygen supply. The addition of surfactants (Triton X-100 and Tween-80) in a nontoxic concentrations resulted in increased biomass yield. Under optimal growth conditions Pseudomonas C12B exhibited the maximal growth rate and yield with C₁₁ as the sole carbon source.     

Abundance of Macroalgal Organic Matter in Biofilms: Evidence from n-Alkane Biomarkers

Biofilm development on titanium panels immersed in the surface waters of Dona Paula Bay was investigated using molecular biomarkers such as n-alkanes and other chemical and biological parameters. Biofilm biomass measured as organic carbon (OC), organic nitrogen (ON), chlorophyll a, diatoms and bacterial numbers on the titanium panels generally increased over the period of immersion. Total lipids and n-alkane concentration also showed similar trends. n-alkanes from C₁₂ to C₃₀ were detected in the biofilm samples, which showed a bimodal distribution. The first mode consisted of n-alkanes > C₂₃ with a strong even over odd predominance. In the second mode, the n-alkanes < C₂₃ were more abundant with odd carbon number maxima at C₁₅, C₁₇ and C₁₉ and a strong odd over even carbon number predominance (Carbon Preference Index > 2). The predominance of these odd-chain n-alkanes strongly indicates that the organic matter derived from macroalgal sources was the major contributor to the biofilm organic matter developed on the titanium panels over the 15 d period of study. The data suggest that molecular characterization is a useful tool in understanding the sources of biofilm organic matter. The observed abundance of macroalgal organic matter during the 15 d period of biofilm development may play an important role in subsequent fouling by micro- and macrofouling organisms.     

Study of genotypic variation of cultivars of winged bean [Psophocarpus tetragonolobus (Stickm.) DC.] with the help of n-alkane profile

The leaf cuticle is covered by epicuticular wax consisting mainly of straight-chain aliphatic hydrocarbons with a variety of substituted groups. Studies have been concentrated on n-alkanes in epicuticular wax of Winged bean [Psophocarpus tetragonolobus (Stickm.) DC.]. Hydrocarbon constituents especially n-alkane analyses of seven cultivars of Winged bean [Psophocarpus tetragonolobus (Stickm.) DC.] have been undertaken. All the n-alkanes in between C₁₄–C₁₈ and C₂₀–C₃₈ are present in each of the species. Among the species, amount of n-alkanes is maximum in IC112417 and relatively low in EC38825. Scanning electron microscopic views were also taken for epicuticular layers and their hydrocarbons of the leaves of all the genotype species of the plant. Qualitative and quantitative characterization of n-alkanes present in the epicuticular wax extracted from the mature leaves can be used as an effective tool in chemo taxonomical work and also for the study of genotypic variation of the different cultivars.     

Incorporation of labelled dietary n-alkanes into cuticular lipids of the grasshopper Melanoplus sanguinipes

Dietary hydrocarbons are incorporated into cuticular lipids of the grasshopper Melanoplus sanguinipes. Dietary secondary alcohols and ketones, however, are not incorporated into the cuticular lipids. In typical experiments from 8 to 28 per cent of the fed labeled n-alkanes are recovered in the cuticular lipids. Most of the radioactivity recovered from feeding the C₂₃ n-alkane and a significant amount from the C₂₅ was found as a secondary alcohol in the form of a wax ester. The C₂₉ and C₃₁ n-alkanes were recovered primarily unchanged as the n-alkane. Eighty-five per cent of injected acetate incorporated into the hydrocarbon fraction is in the branched hydrocarbons. These results show that the insect synthesizes its branched hydrocarbons, whereas a large part of the normal hydrocarbons can be dietary.     

Utilization of phenol by hydrocarbon assimilating yeasts

77 Ascomycetous, basidiomycetous as well as imperfect yeast strains of 46 different species and 20 genera were tested for growth with the substrates n-octane, n-hexadecane, and phenol. Of 59 yeast strains with ascomycetous cell wall structure 33 grew on hydrocarbons and 32 on phenol. No yeast strain out of 26 which are unable to use n-alkanes as a source of carbon and energy grew on phenol. In comparison with the latter 32 out of 33 n-hexadecane assimilating yeasts were also capable of using phenol. All n-octane utilizing yeasts of this group also assimilate phenol as a carbon source for growth.The correlation of the hydrocarbon assimilation with the phenol assimilation seems to be not so strong in the basidiomycetous yeasts. 7 out of 18 strains from this group grew on n-hexadecane and 13 on phenol.Furthermore, it could be shown that the use of hydrocarbons and phenol (as well as methanol) is strongly correlated with the coenzyme Q structure of the respective yeast strain.The results are discussed with respect to the particular chemical properties of the substrates used and the fact that coenzyme Q structure is considered to be an important marker of evolutionary relationships among yeasts.     

GC-MS studies on extracts and distillates from Posidonomia shales (FRG) and from fossil wood out of these shales

Summary In this study Posidonomia shale extracts, Posidonomia shale distillates and extracts of fossil wood (gagat) found in these shales were seperated on GC and identified by GC-MS. Samples were obtained from Dotternhausen oil shale formation (FRG) belonging to LIAS epsilon (Toarcien). Main components were n-alkanes ranging from C₇ to C₂₇ with a maximum at C₁₇ for shales and two maxima at C₁₇ and C₉ respectively for fossil wood. Isoprenoid hydrocarbons present in shales and fossil wood as well were 2,6,10-trimethyltridecane, 2,6,10-trimethylpentadecane, 2,6,10,14-tetramethylpentadecane (pristane) and 2,6,10,14-tetramethylhexadecane (phytane).Numerous low molecular weight cycloalkanes with 6 to 9 carbon atoms were present in fossil wood. Of these, the main constituent could also be found in shales. Also aromatic hydrocarbon compounds were numerous in the low boiling fraction of extracts of fossil wood.The results obtained are discussed with respect to the maturity of the Dotternhausen sediments.     

Fatty Acid Composition of Hydrocarbon-Assimilating Yeast

As a part of extensive program on microbial utilization of hydrocarbons, lipid components of Candida petrophillum SD-14 grown on n-alkanes and glucose as carbon sources were studied. In any carbon source, cellular fatty acids of the yeast contained palmitic, palmitoleic, stearic, oleic and linoleic acids as major components.

When n-tridecane was fed to the yeast, fatty acids with odd- and even-number of carbon atoms were produced in almost identical quantity. Another yeast, Torulopsis petrophillum SD-77, also gave a very similar fatty acid pattern by n-tridecane substrate. These phenomena indicate the existence of C₂ addition and β-oxidation of the fatty acid formed in the yeasts.

In the cases of n-tridecane, n-hexadecane and glucose as substrate, about a half of SD-14’s lipid was phospholipid, which consisted of phosphatidyl ethanolamine and phosphatidyl choline principally. Free alcohol and wax were not detected in any case.     

Epicuticular hydrocarbons of Drosophila pseudoobscura (Diptera; Drosophilidae) Identification of unusual alkadiene and alkatriene positional isomers

Epicuticular hydrocarbons of Drosophila pseudoobscura were analyzed by gas chromatography and mass spectrometry. Methyl-branched alkanes and alkadienes were the predominant hydrocarbons, with lesser amounts of monoenes (14%) and trienes (9%) also present. Alkanes (49%) were mostly odd carbon number 2-methylalkanes (C₂₅–C₃₁). Alkadienes (27%) were odd carbon number components (C₂₅–C₃₃), with the (Z,Z)-5,9-isomer predominating. Monounsaturated hydrocarbons were a mixture of 5-, 7-, 9-, 11-, 13-, 14- and 15-isomers containing 25–33 carbon atoms. The major alkatriene components contained 29–31 carbon atoms and were either 5,19,17- or 5,9,19-isomers. Sodium[1-¹⁴C]acetate was incorporated into each class of hydrocarbon and into each of the major alkadienes.     

Isolation and identification of cuticular compounds from the mediterranean flour moth,Ephestia kuehniella Zeller (Lepidoptera: Pyralidae), their antibacterial activities and biological functions

Cuticular analysis of Ephestia kuehniella females by gas chromatography-mass spectrometry revealed the presence of four groups of chemical compounds including alkane, alcohol, aldehyde and fatty acid. The cuticular n-alkanes ranged from 12 to 18, 20, 23, 24 and 29 carbon atoms in the chain. The most abundant n-alkanes detected in the cuticular extracts were C₁₄ (14.98%) and C₁₈ (8.15%). Cuticular fatty acids included hexadecenoic acid, 9-octadecenoic acid and 9,12-octadecenoic acid. Two types of alcohol including, 2-methyl-Z,Z-3,13-octadecadienol and 9-methyl-Z-10-tetradecen-1-ol acetate, were found in the cuticular lipids of the females. Two aldehyde components, (E)-11-hexadecenal and 9,17-octadecadienal, were identified in the cuticular extract of E. kuehniella. Antibacterial activity of the cuticular compounds was tested against Bacillus subtilis, Bacillus thuringiensis and Escherichia coli. These compounds from the moths inhibited the growth of Gram-positive bacteria. The functional characteristics of the cuticular compounds operating as pheromones, species-associated compounds and host-resistant compounds to bacterial infection are discussed.     

A sensitive bioassay for spider mite (Tetranychus urticae) repellency: a double bond makes a difference

Choice bioassays were used to determine repellency of homologous n-alkanes (C₈H₁₈–C₂₁H₄₄) to spider mites. When tested at 400 μg/cm², the C₁₅–C₁₉ alkanes were highly repellent; the C₁₆ n-alkane, n-hexadecane, was most repellent. Subsequently the EC₅₀ values, the concentration at which 50% of the mites were repelled, were determined for the C₁₅–C₁₉ n-alkanes and their analogous 1-n-alkenes (C₁₅H₃₀–C₁₉H₃₈). The EC₅₀ value for 1-heptadecene, the C₁₇ 1-n-alkene, was the lowest observed. Except for the 17-carbon hydrocarbons, the EC₅₀ values for the n-alkanes were less than those for their analogous 1-n-alkenes. Depending on the compounds evaluated, there was as much as a six-fold difference of repellency between an n-alkane its analogous 1-n-alkene. Thus, the bioassay has sufficient sensitivity to detect behavioral differences associated with the presence or absence of a single double bond. The EC₅₀ values for the most repellent hydrocarbons were similar to that reported for 2,3-dihydrofarnesoic acid, a naturally occurring repellent isolated from trichome secretions of a wild tomato, Solanum habrochaites, and also were similar to concentrations used to evaluate arthropod repellents. Consequently, this bioassay may be useful for providing a better understanding of the relationships between structures and activities of natural products that are repellent to spider mites.     

Hydrocarbons Associated with the Developing Microspores in the Anther Loculus of Tulipa

Abstract: Hydrocarbons associated with the developing microspores in the anther loculus of Tulipa cv. Apeldoorn were investigated. They occurred mainly at chain lengths between C₁₉ and C₂₉. At the lower chain lengths the n-alkanes, at higher chain lengths the alkenes dominated. During microspore development the ratio of unsaturated to saturated hydrocarbons in the extracts changed. While the content of all main hydrocarbons increased, the content of the alkanes C₁₉, C₂₁ and C₂₃ increased to 3.8, 3.4 and 3.3 times the initial value compared to 2.1, 2.0 and 2.2 times in case of the alkenes C₂₅, C₂₇ and C₂₉. Surface lipids from petals, leaves and ripe pollen were analyzed in comparison and these analyses confirmed that a high amount of alkenes was unique for microspores. Iso-heptacosane was the main hydrocarbon from ripe pollen, heptacosene was a main component when microspore extracts were analyzed.     

Intraspecific variation in photosynthetic responses of trebouxioid lichens with reference to the activity of a carbon-concentrating mechanism

The photosynthetic responses of a range of trebouxioid lichens were investigated to determine whether variations in net assimilation rates shown by populations of the same species collected from different habitats could be correlated with adjustments in carbon-concentrating mechanism (CCM) activity. The activity of a CCM was inferred from the high affinity for CO₂ [i.e. low CO₂ compensation point (Γ); low external CO₂ concentration at which half-maximal assimilation rates are reached (K _{0.5 CO2})], the release of a pool of accumulated dissolved inorganic carbon (C_i) during light/dark transient measurements of CO₂ exchange and values for carbon isotope discrimination intermediate between those characteristic of C₃ and C₄ terrestrial plants. Higher net and gross assimilation rates were expressed by lichens collected from shaded woodland habitats. The higher rates were not accounted for by variations in chlorophyll content. Lichens with high assimilation rates also showed an increased affinity for CO₂ as demonstrated by low CO₂ compensation points and K _0.5 values and the magnitude of the C_i pool accumulated upon illumination and released after darkening of the thalli. However, there was no correlation between assimilation rates and organic matter or instantaneous carbon isotope discrimination measurements, with the latter remaining roughly consistent whatever the provenance or species of the lichen material. The data are discussed with reference to significant environmental factors which are likely to control photosynthesis in the habitats studied. Received: 5 April 1997 / Accepted: 9 September 1997     

Initiation of efficient C4 pathway in response to low ambient CO2 during the bloom period of a marine dinoflagellate

Dinoflagellates are important primary producers and major causative agents of harmful algal blooms in the global ocean. Despite the great ecological significance, the photosynthetic carbon acquisition by dinoflagellates is still poorly understood. The pathways of photosynthetic carbon assimilation in a marine dinoflagellate Prorocentrum donghaiense under both in situ and laboratory-simulated bloom conditions were investigated using a combination of metaproteomics, qPCR, stable carbon isotope and targeted metabolomics approaches. A rapid consumption of dissolved CO₂ to generate high biomass was observed as the bloom proceeded. The carbon assimilation genes and proteins including intracellular carbonic anhydrase 2, phosphoenolpyruvate carboxylase, phosphoenolpyruvate carboxykinase and RubisCO as well as their enzyme activities were all highly expressed at the low CO₂ level, indicating that C₄ photosynthetic pathway functioned in the blooming P. donghaiense cells. Furthermore, δ¹³C values and content of C₄ compound (malate) significantly increased with the decreasing CO₂ concentration. The transition from C₃ to C₄ pathway minimizes the internal CO₂ leakage and guarantees efficient carbon fixation at the low CO₂ level. This study demonstrates the existence of C₄ photosynthetic pathway in a marine dinoflagellate and reveals its important complementary role to assist carbon assimilation for cell proliferation during the bloom period.     

Degradation of long-chain n-alkanes by the yeast Candida maltosa

Summary The yeast Candida maltosa precultivated on liquid n-alkanes utilized different solid n-alkanes (especially C₂₀–C₂₅) in the presence of pristane as an organic phase with rates comparable to, or somewhat larger than, those of liquid n-alkanes. Analysis of cellular fatty acids indicated an assimilation of solid n-alkanes via monoterminal oxidation. The resulting fatty acids with substrate chain length were chain-shortened by C₂ units down to an optimal range of chain length from C₁₆ to C₁₈ and incorporated into cellular, lipids directly or after desaturation. The intermediates of chain-shortening with numbers of carbon atoms higher than C₁₈, as well as the unusually long-chain fatty acids of substrate chain length, were detected in trace amounts only. Even-carbon-numbered and odd-numbered fatty acids predominated in experiments with evenchain and odd-chain n-alkanes, respectively. Studies with cerulenin indicated that de novo synthesis of fatty acids was negligible. Oxidation of solid n-alkanes by the yeast C. maltosa yielded fatty acid patterns similar to those of cells grown on liquid n-alkanes.     

The occurrence of monounsaturated n-C21 and polyunsaturated C25 sedimentary hydrocarbons in the lipids of Antarctic marine organisms

Antarctic zooplankton have been found to be a potential source of sedimentary hydrocarbons. Monounsaturated C₂₁ n-alkenes and highly branched polyunsaturated C₂₅ n-alkenes were analysed in the aliphatic fraction of the lipids of Antarctic pelagic and inshore marine organisms. Cluster analysis of the species-based data set produced four main groups: phytoplankton, epipelagic herbivores, epipelagic carnivores and mesopelagic omnivores. The detailed pattern of alkenes exhibited differences within the groups and also with tissue type (krill, Euphausia superba). The origin of alkenes in Antarctic biota appeared to be either synthesis de novo or due to the condensation of smaller molecules. Formation of alkenes by the decarboxylation of fatty acids was not consistent with the hydrocarbon and fatty acid composition of Antarctic zooplankton. There was no evidence for direct assimilation of C₂₁ and C₂₅ alkenes by zooplankton or higher predators from their diet. Zooplankton C₂₅ alkenes are probably transported unaltered directly to the sediment as detritus or via predators in faecal material. Sedimentary C₂₅ alkenes are proposed as biomarkers of recent zooplankton activity in the water column.     

New insight into the contributions of thermogenic processes and biogenic sources to the generation of organic compounds in hydrothermal fluids

Experiments on hydrothermal degradation of Pyrococcus abyssi biomass were conducted at elevated pressure (40 MPa) over a 200–450 °C temperature range in sapphire reaction cells. Few organic compounds could be detected in the 200 °C experiment. This lack was attributed to an incomplete degradation of P. abyssi cells. On the contrary, a wide range of soluble organic molecules were generated at temperatures ≥350 °C including toluene, styrene, C₈–C₁₆ alkyl‐benzenes, naphthalene, C₁₁–C₁₆ alkyl‐naphthalenes, even carbon number C₁₂–C₁₈ polycyclic aromatic hydrocarbons, C₁₅–C₁₈ alkyl‐phenanthrenes and C_8:0–C_16:0 n‐carboxylic acids. The effect of time on the final organic composition of the degraded P. abyssi solutions at 350 °C was also investigated. For that purpose the biomass was exposed for 10, 20, 60, 90, 270 and 720 min at 350 °C. We observed a similar effect of temperature and time on the chemical diversity obtained. In addition, temperature and time increased the degree of alkylation of alkyl‐benzenes. This study offers additional evidence that a portion of the aliphatic hydrocarbons present in the fluids from the Rainbow ultramafic‐hosted hydrothermal field may be abiogenic whereas a portion of the aromatic hydrocarbons and n‐carboxylic acids may have a biogenic origin. We suggest that aromatic hydrocarbons and linear fatty acids at the Rainbow site may be derived directly from thermogenic alteration of material from the sub‐seafloor biosphere. Yet we infer that the formation and dissolution of carboxylic acids in hydrothermal fluids may be controlled by other processes than in our experiments.     

Biosynthesis of acyclic methyl branched polyunsaturated hydrocarbons inPseudomonas maltophilia

Summary The hydrocarbon composition ofPseudomonas maltophilia was determined by gas chromatography-mass spectrometry. Mono-, di- and tri-unsaturated alkenes were identified with a predominance of polyunsaturated components. The carbon chains of the alkenes contained single methyl branches iniso andanteiso position and double methyl branches in theiso-iso andanteiso-anteiso configurations. The composition of the hydrocarbons from cells grown in synthetic media enriched with amino acids or volatile fatty acids demonstrated that the probable precursors incorporated into individual hydrocarbons were branched and normal fatty acid chains in the range from C₃ to C₁₆. The probable fatty acid precursors which were connected together to form the major triunsaturated hydrocarbon chains were two monounsaturated chains, whereas the major liunsaturated chains resulted from condensation of saturated and monounsaturated chains. The probable precursors for the major monounsaturated hydrocarbons were C₁₄ (C₁₅) and C₁₆ (C₁₅) fatty acids. The accumulation of hydrocarbons was not detected until the cells were in the late exponential phase of growth; the maximal levels were reached at the mid-stationary phase of growth.     

Extractive compounds of birch buds (<Emphasis Type="Italic">Betula pendula</Emphasis> Roth.): II. Carbonyl compounds and oxides. Esters

This is the first report devoted to study of the hydrocarbon composition of the extract of buds of European birch Betula pendula (family Betulacea). We have identified saturated (C₁₆ to C₂₈, even number of carbon atoms) and unsaturated (linoleic and linolenic) fatty acids, β-caryophyllene, α-humulene, and the components of epicuticular waxes of cover scales, such as n-alkanes (C₂₁ to C₂₆), esters of fatty acids (C₁₆ to C₂₈, even number of carbon atoms), and fatty alcohols (C₁₈ to C₃₀, even number of carbon atoms). The gas chromatographic retention indices of all identified compounds have been determined.