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1
Koch, Daniel J., Mike M. Chen, Jan B. van Beilen, and Frances H. Arnold. "In Vivo Evolution of Butane Oxidation by Terminal Alkane Hydroxylases AlkB and CYP153A6." Applied and Environmental Microbiology 75, no. 2 (November 14, 2008): 337–44. http://dx.doi.org/10.1128/aem.01758-08.
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ABSTRACT Enzymes of the AlkB and CYP153 families catalyze the first step in the catabolism of medium-chain-length alkanes, selective oxidation of the alkane to the 1-alkanol, and enable their host organisms to utilize alkanes as carbon sources. Small, gaseous alkanes, however, are converted to alkanols by evolutionarily unrelated methane monooxygenases. Propane and butane can be oxidized by CYP enzymes engineered in the laboratory, but these produce predominantly the 2-alkanols. Here we report the in vivo-directed evolution of two medium-chain-length terminal alkane hydroxylases, the integral membrane di-iron enzyme AlkB from Pseudomonas putida GPo1 and the class II-type soluble CYP153A6 from Mycobacterium sp. strain HXN-1500, to enhance their activity on small alkanes. We established a P. putida evolution system that enables selection for terminal alkane hydroxylase activity and used it to select propane- and butane-oxidizing enzymes based on enhanced growth complementation of an adapted P. putida GPo12(pGEc47ΔB) strain. The resulting enzymes exhibited higher rates of 1-butanol production from butane and maintained their preference for terminal hydroxylation. This in vivo evolution system could be useful for directed evolution of enzymes that function efficiently to hydroxylate small alkanes in engineered hosts.
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Lyu, Ruihe, Mohammed S. Alam, Christopher Stark, Ruixin Xu, Zongbo Shi, Yinchang Feng, and Roy M. Harrison. "Aliphatic carbonyl compounds (C<sub>8</sub>–C<sub>26</sub>) in wintertime atmospheric aerosol in London, UK." Atmospheric Chemistry and Physics 19, no. 4 (February 20, 2019): 2233–46. http://dx.doi.org/10.5194/acp-19-2233-2019.
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Abstract. Three groups of aliphatic carbonyl compounds, the n-alkanals (C8–C20), n-alkan-2-ones (C8–C26), and n-alkan-3-ones (C8–C19), were measured in both particulate and vapour phases in air samples collected in London from January to April 2017. Four sites were sampled including two rooftop background sites, one ground-level urban background site, and a street canyon location on Marylebone Road in central London. The n-alkanals showed the highest concentrations, followed by the n-alkan-2-ones and the n-alkan-3-ones, the latter having appreciably lower concentrations. It seems likely that all compound groups have both primary and secondary sources and these are considered in light of published laboratory work on the oxidation products of high-molecular-weight n-alkanes. All compound groups show a relatively low correlation with black carbon and NOx in the background air of London, but in street canyon air heavily impacted by vehicle emissions, stronger correlations emerge, especially for the n-alkanals. It appears that vehicle exhaust is likely to be a major contributor for concentrations of the n-alkanals, whereas it is a much smaller contributor to the n-alkan-2-ones and n-alkan-3-ones. Other primary sources such as cooking or wood burning may be contributors for the ketones but were not directly evaluated. It seems likely that there is also a significant contribution from the photo-oxidation of n-alkanes and this would be consistent with the much higher abundance of n-alkan-2-ones relative to n-alkan-3-ones if the formation mechanism were through the oxidation of condensed-phase alkanes. Vapour–particle partitioning fitted the Pankow model well for the n-alkan-2-ones but less well for the other compound groups, although somewhat stronger relationships were seen at the Marylebone Road site than at the background sites. The former observation gives support to the n-alkane-2-ones being a predominantly secondary product, whereas primary sources of the other groups are more prominent.
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Serebrennikova, Ol'ga Viktorovna, Evgeniya Borisovna Strel’nikova, and Irina Vladimirovna Russkikh. "FEATURES OF LIPID COMPOSITION OF SPHAGNUM AND TRUE MOSSES FROM VARIOUS NATURAL CLI-MATIC ZONES." chemistry of plant raw material, no. 3 (April 12, 2019): 225–34. http://dx.doi.org/10.14258/jcprm.2019034558.
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A composition of 16 lipid samples of sphagnum and true mosses (Bryales) growing at an average annual temperature ranging from -9.1 °C to 1.5 °C is investigated by gas chromatography-mass spectrometry. The individual composition and content of n-alkanes, fatty n-acids and their esters, n-alkane-2-ones, aldehydes, farnesylfuranes, polycyclic aromatic hydrocarbons (PAHs), tocopherols, squalene, steroids, sesqui-, di- and triterpenoids of these mosses are determined. True mosses differ from sphagnum mosses in their lower content of n-alkanes, n-alkan-2-ones, n-aldehydes, tocopherols and cyclic terpenoids, and a higher content of PAHs. Campesterol prevails among steroids of true mosses, while stigmasterol and sitosterol dominate in sphagnum mosses. Sitosterol prevails in sphagnum mosses growing in areas with a negative average annual temperature. An increase in the temperature of the habitat results in a decrease in the relative content of n-alkanes with odd number of carbon atoms in the molecule in true mosses, and a slight decrease in their average chain length in sphagnum mosses. It is shown that terpenoids are the most dependent on natural habitat conditions of mosses. This is indicated by the content of squalene, sesqui- and diterpenoids, the ratio of hydrocarbons to oxygen-containing structures of cyclic triterpenoids, and that of compounds from series of perhydropicene and cyclopentapeperhydrochryzene. The increased humidity of habitat of a moss eliminates the effect of temperature. The stability of composition of n-alkanes and n-alkan-2-ones of sphagnum mosses developing under various conditions makes it possible to consider these compounds as potential chemotaxonomic markers of sphagnum mosses in peat deposits.
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Shu, Bin, Lijun Lin, Yingjun Zhang, Hai Wang, and Hailing Luo. "N-alkane profiles of common rangeland species in northern China and the influence of drying method on their concentrations." Canadian Journal of Plant Science 88, no. 1 (January 1, 2008): 137–41. http://dx.doi.org/10.4141/cjps07008.
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Plant wax alkanes have been used as internal markers to estimate diet composition of grazing animals. However, alkane contents in samples may vary depending on the drying method used. This study was undertaken to determine the alkane profiles and concentrations of 17 common range land species in northern China with two different drying methods. The results showed that regardless of drying methods, the odd-chain alkanes, particular C29 and C33, predominated in cuticular wax in all 17 common species and their component plant parts. The alkane patterns of plant species within the same genus were relatively similar and the differences in alkanes between stem and leaf were generally smaller than those between inflorescences and leaf or stem. The influence of drying methods on alkane concentrations varied depending on family and individual alkane. The effect of drying methods on C29 seemed to be smaller than other alkanes in all the samples. The oven-dry method produced higher concentrations (P < 0.05) in the three major alkanes (C23, C31 and C33) in the Gramineae family than the freeze-dry method. Therefore, studies dealing with alkane concentrations should use the same drying method for all samples. Key words: Alkane pattern, steppe grassland, oven-dry, freeze-dry
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Mayes, R. W., C. S. Lamb, and Patricia M. Colgrove. "The use of dosed and herbage n-alkanes as markers for the determination of herbage intake." Journal of Agricultural Science 107, no. 1 (August 1986): 161–70. http://dx.doi.org/10.1017/s0021859600066910.
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SUMMARYThe recovery in the faeces of the n-alkanes of herbage (odd-chain, C27–C35) and of dosed artificial alkanes (even-chain, C28 and C32) was studied in twelve 4-month-old castrated male lambs. The lambs received three levels of cut, fresh perennial ryegrass or a mixed diet of perennial ryegrass (0·70) and a barley-based concentrate (0·30) (500–900 g D.M./day). C28 and C32 n-alkanes (130 mg each), absorbed onto shredded paper, were given once daily for 17 days to test whether the recoveries of herbage and dosed alkanes were similar to enable their use as markers for determining the herbage intake of grazing sheep. Stearic and palmitic acids (130 mg each) were given with the dosed alkanes to half of the animals with the objective of facilitating emulsification of the dosed alkanes within the digestive tract.With the exception of C27 n-alkane, the faecal recoveries of all alkanes were unaffected by diet, feeding level or emulsifying agent. Faecal recovery of odd- chain herbage n-alkanes increased with increasing C-chain length. The recovery of the dosed C28 n-alkane was slightly greater than the recoveries of both C27, and C29 n-alkanes of herbage. The recoveries of the dosed C32 n-alkane and the herbage C33-alkane were the same.The mean herbage intake estimated using C33 and C32 n-alkanes was identical to the actual herbage intake. Other alkane pairs gave slight underestimates of herbage intake ranging from 3·5% for the C28–C29 pair to 7·6% for the C27–C28 pair. No cyclical pattern of n-alkane excretion throughout the day was observed. Examination of daily variations in faecal alkane concentrations indicated that the start of alkane dosing should precede the sampling of faeces by at least 6 days.These results suggest that accurate estimation of herbage intake in grazing sheep is possible from the simultaneous use of dosed C32 and herbage C33 n-alkanes as markers.The method may be particularly useful in enabling unbiased estimates of herbage intake to be made in animals receiving supplementary feed.
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Smits, Theo H. M., Stefanie B. Balada, Bernard Witholt, and Jan B. van Beilen. "Functional Analysis of Alkane Hydroxylases from Gram-Negative and Gram-Positive Bacteria." Journal of Bacteriology 184, no. 6 (March 15, 2002): 1733–42. http://dx.doi.org/10.1128/jb.184.6.1733-1742.2002.
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ABSTRACT We have cloned homologs of the Pseudomonas putida GPo1 alkane hydroxylase from Pseudomonas aeruginosa PAO1, Pseudomonas fluorescens CHA0, Alcanivorax borkumensis AP1, Mycobacterium tuberculosis H37Rv, and Prauserella rugosa NRRL B-2295. Sequence comparisons show that the level of protein sequence identity between the homologs is as low as 35%, and that the Pseudomonas alkane hydroxylases are as distantly related to each other as to the remaining alkane hydroxylases. Based on the observation that rubredoxin, an electron transfer component of the GPo1 alkane hydroxylase system, can be replaced by rubredoxins from other alkane hydroxylase systems, we have developed three recombinant host strains for the functional analysis of the novel alkane hydroxylase genes. Two hosts, Escherichia coli GEc137 and P. putida GPo12, were equipped with pGEc47ΔB, which encodes all proteins necessary for growth on medium-chain-length alkanes (C6 to C12), except a functional alkane hydroxylase. The third host was an alkB knockout derivative of P. fluorescens CHA0, which is no longer able to grow on C12 to C16 alkanes. All alkane hydroxylase homologs, except the Acinetobacter sp. ADP1 AlkM, allowed at least one of the three hosts to grow on n-alkanes.
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Chen, W., J. M. Scott, G. J. Blair, and R. D. B. Lefroy. "Using plant cuticular alkanes to study plant-animal interactions on pastures." Canadian Journal of Animal Science 79, no. 4 (December 1, 1999): 553–56. http://dx.doi.org/10.4141/a99-046.
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Two experiments were conducted to validate an approach of using plant cuticular alkanes to estimate diet composition and fecal output. In the first experiment, n-alkane patterns of the four major pasture species were determined and compared and a further two sets of pasture mixtures were prepared to validate the use of plant n-alkane patterns to estimate species composition. In the second experiment, estimates of daily fecal output of grazing sheep were compared using controlled-released devices containing either Cr2O3 or alkanes. There were considerable differences in odd-numbered alkanes and in their total content between species. Results from the first experiment, where two sets of pasture mixtures were analyzed suggest that it is feasible to separate species composition using differences in n-alkane pattern. The second experiment showed that accurate estimation of daily fecal output can also be obtained using capsules containing alkanes. Key words: n-alkane, pasture, diet composition, fecal output
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Baldwin, Robert L., and George D. Rose. "How the hydrophobic factor drives protein folding." Proceedings of the National Academy of Sciences 113, no. 44 (October 17, 2016): 12462–66. http://dx.doi.org/10.1073/pnas.1610541113.
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How hydrophobicity (HY) drives protein folding is studied. The 1971 Nozaki–Tanford method of measuring HY is modified to use gases as solutes, not crystals, and this makes the method easy to use. Alkanes are found to be much more hydrophobic than rare gases, and the two different kinds of HY are termed intrinsic (rare gases) and extrinsic (alkanes). The HY values of rare gases are proportional to solvent-accessible surface area (ASA), whereas the HY values of alkanes depend on special hydration shells. Earlier work showed that hydration shells produce the hydration energetics of alkanes. Evidence is given here that the transfer energetics of alkanes to cyclohexane [Wolfenden R, Lewis CA, Jr, Yuan Y, Carter CW, Jr (2015) Proc Natl Acad Sci USA 112(24):7484–7488] measure the release of these shells. Alkane shells are stabilized importantly by van der Waals interactions between alkane carbon and water oxygen atoms. Thus, rare gases cannot form this type of shell. The very short (approximately picoseconds) lifetime of the van der Waals interaction probably explains why NMR efforts to detect alkane hydration shells have failed. The close similarity between the sizes of the opposing energetics for forming or releasing alkane shells confirms the presence of these shells on alkanes and supports Kauzmann's 1959 mechanism of protein folding. A space-filling model is given for the hydration shells on linear alkanes. The model reproduces the n values of Jorgensen et al. [Jorgensen WL, Gao J, Ravimohan C (1985) J Phys Chem 89:3470–3473] for the number of waters in alkane hydration shells.
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LIN, L. J., H. L. LUO, Y. J. ZHANG, and B. SHU. "The effects, in sheep, of dietary plant species and animal live weight on the faecal recovery rates of alkanes and the accuracy of intake and diet composition estimates obtained using alkanes as faecal markers." Journal of Agricultural Science 145, no. 1 (November 14, 2006): 87–94. http://dx.doi.org/10.1017/s002185960600654x.
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Alkanes can be used as natural markers for estimating diet composition, but a factor should be used to correct for incomplete recovery in faeces. Faecal alkane recovery rates may be influenced by diet and animal factors. However, little research has been conducted to evaluate the effects of herbage species and live weight of animals on faecal alkane recoveries. In the current study, faecal recoveries of alkanes were determined in sheep in four different live weight groups (from 20 to 40 kg) fed three plant species (Elymus sibiricum, Leymus chinensis and L. dasystachys). In a second experiment, the accuracy of intake and diet composition estimates, using alkanes as faecal markers, was assessed by feeding known amounts of the same plant species as a three-component mixture. The results showed that faecal alkane recoveries were influenced significantly by herbage species (P<0·01), but no effect of live weight of animals was observed. Total dry matter intake was estimated correctly based on either C31:C32 or C29:C32 alkane pairs. With respect to estimators of E. sibiricum intake, reasonable results could only be obtained if the faecal alkane concentration was corrected based on diet-specific faecal recovery. More accurate estimations were obtained only if the alkanes found in relatively higher concentrations were used in diet composition estimates instead of using all available alkanes. Due to lower alkane concentrations or similar alkane patterns of L. chinensis and L. dasystachys in the diet, estimates of diet composition of these two herbage species were significantly different from the actual ones (P<0·05), implying that other markers need to be used for accurate estimation.
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Hendricksen, R. E., M. M. Reich, R. F. Roberton, D. J. Reid, C. Gazzola, J. A. Rideout, and R. A. Hill. "Estimating the voluntary intake and digestibility of buffel-grass and lucerne hays offered to Brahman-cross cattle using n-alkanes." Animal Science 74, no. 3 (June 2002): 567–77. http://dx.doi.org/10.1017/s1357729800052723.
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AbstractThe n-alkane method was developed in temperate areas as a tool to estimate voluntary intake (VI) at pasture. The present study aimed to investigate the performance of n-alkanes as markers for estimating VI of steers (mean live weight 213 kg) offered a range of tropical grass hays and lucerne. Tropical and temperate forages have different n-alkane profiles and little is known about the issues which affect the accuracy of the method under tropical conditions. In two pen experiments (no. = 20 and no. = 24) n-alkanes were dosed using intraruminal controlled-release devices. Actual mean voluntary dry matter intakes for the diets ranged from 3·12 to 4·60 kg/day and actual mean dry-matter digestibility varied between 439 and 620 g/kg. n-Alkane profiles (C30 to C36) of the diets and the faeces for each animal were determined using gas chromatography. The recovery of each n-alkane was determined for each animal. Recoveries of n-alkanes were highly variable and generally varied between diets and between experiments. When adjacent n-alkanes were used to estimate VI (ratio method), agreement with actual VI was often poor. Despite this, where the recoveries of n-alkane pairs were similar, group mean VI were accurately estimated. From these data, it is concluded that estimation of VI in cattle offered tropical grass hays or lucerne hay, requires measured recoveries of both dosed and natural plant n-alkanes. The dosed and natural n-alkane pairs having the most similar recoveries should be used in the ratio method to estimate VI.
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Vulich, S. A., E. G. O'Riordan, and J. P. Hanrahan. "Use of n-alkanes for the estimation of herbage intake in sheep: accuracy and precision of the estimates." Journal of Agricultural Science 116, no. 2 (April 1991): 319–23. http://dx.doi.org/10.1017/s0021859600077741.
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SUMMARYTwo experiments at Belclare, Co. Galway, in late autumn 1988, evaluated the use of herbage and dosed n-alkanes for estimating herbage intake by sheep. The first experiment examined faecal recoveries of dosed and herbage n-alkanes. The second experiment assessed the accuracy and precision of herbage intake estimates obtained using the n-alkane technique, and tested the effect of supplying n-alkanes to animals either in gelatine. capsules (containing different ratios of n-alkane: cellulose fibre) or in pellets prepared from shredded paper onto which the n-alkanes had been adsorbed. Individually penned wether lambs were offered freshly cut herbage ad libitum (+ 10%) and actual dry matter intake was recorded daily. Intake was estimated using the C31:C32 and C33:C32 (natural:dosed) n-alkane ratios.There was no significant effect of n-alkane chain length on faecal recovery rate for either the dosed n-alkanes (C32 and C36), the herbage odd-chained n-alkanes (C29, C31, C33 and C36) or those used for the estimation of herbage intake (C31, C32 and C33). The accuracy and precision of the n-alkane technique for estimating herbage intake were unaffected by whether the dosed n-alkane was supplied in capsules or pellets or by the n-alkane:cellulose fibre ratio in the capsules. The bias in the estimated intake was – 8% (± 1·1%) and + 3% (± 1·2%) for estimates based on C31:C32 and C33:C32 ratios, respectively. The estimates based on C31:C32 and C33:C32 exhibited similar precision in the estimation of herbage intake, with a R.S.D. of 6% in actual intake when adjusted for variation in estimated intake and a correlation of +0·92 between actual and estimated herbage intake. The C.V. for actual herbage intake was 17%. The repeatability of actual dry matter intake over three consecutive 6-day periods was 0·54 while those of estimated intake were 0·57 and 0·60 for estimates based on C31:C32 and C33:C32, respectively. The results show that the n-alkane technique can provide an accurate and precise estimate of herbage intake.
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BROSH, A., Z. HENKIN, S. J. ROTHMAN, Y. AHARONI, A. ORLOV, and A. ARIELI. "Effects of faecal n-alkane recovery in estimates of diet composition." Journal of Agricultural Science 140, no. 1 (February 2003): 93–100. http://dx.doi.org/10.1017/s0021859602002757.
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The outer surfaces of plant leaves and stems are covered with a waxy layer, a considerable fraction of which comprises n-alkanes which are not digested and, therefore, can be used as markers in animal nutrition studies. Most plant species have a characteristic pattern of n-alkane concentrations in their cuticular wax and this enables the diet composition to be estimated by comparison with the pattern of the n-alkanes in faeces. N-alkane recovery in faeces was determined in a digestibility trial involving three different diets given to four goats, six cows and five calves. The validity of using n-alkane markers to determine diet composition was examined in in vivo feeding trials with goats and cows. The recovery of the odd chain length n-alkanes increased linearly with n-alkane chain length, with no significant differences between treatments. Estimates of diet composition were affected by the faecal n-alkane recovery rate. N-alkanes in plant cuticular wax can be used as natural markers for estimating diet composition, but a recovery factor should be used to correct for incomplete recovery in faeces. More research is needed to extend the findings to wider ranges of diets, animals, environmental conditions and physiological and reproductive states.
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Boadi, D. A., S. A. Moshtaghi Nia, K. M. Wittenberg, and W. P. McCaughey. "The n-alkane profile of some native and cultivated forages in Canada." Canadian Journal of Animal Science 82, no. 3 (September 1, 2002): 465–69. http://dx.doi.org/10.4141/a01-084.
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Frage samples were collected from swards growing in Carberry, Manitoba, Brandon, Manitoba, Saskatoon, Saskatchewan, and St. John’s, Newfoundland, and the alkane concentrations were determined by gas chromatography. Considerable differences were observed in almost all odd-numbered alkanes and in their total content between species. The odd-numbered alkanes were always present in high concentrations compared to the even-chain alkanes in both native and cultivated species. Of the cultivated grasses, the fescues had very high concentrations of CN31 among the odd-chain alkanes, while the legumes tended to have higher concentrations of C29 than C31 or C33. The low concentrations of odd-chain alkanes (< 50 mg kg-1 DM) in little bluestem, indiangrass, reed canarygrass, orchardgrass, timothy and Russian wildrye forages could bias intake calculations of these forages when the double alkane technique is used. Differences between location and cultivar were observed for C29 in timothy and C31 in meadow bromegrass (P < 0.05). There were no effects of location and cultivar on n-alkane concentrations for orchardgrass (P > 0.05). Key words: n-alkanes, forage species, cultivar, location
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LIN, L., G. LIU, and Y. ZHANG. "Study on the n-alkane patterns of five dominant forage species of the typical steppe grassland in Inner Mongolia of China." Journal of Agricultural Science 144, no. 2 (March 6, 2006): 159–64. http://dx.doi.org/10.1017/s0021859606005995.
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The alkane patterns of the dominant forage species of the typical steppe grassland in Inner Mongolia were clarified, and the effects of species, sampling time and site on the concentrations of alkanes were evaluated. The results showed that alkanes with odd-numbered carbon chains in the range C25 (n-pentacosane)–C35 (n-pentatriacontane) were predominant in cuticular wax in five dominant grasses of the typical steppe. The C31 (n-hentriacontane) alkanes were always present in the highest concentration in the grass species, especially in the Stipa daicalensis and Stipa grandis. Samples of Artemisia frigida contained not only high concentrations of odd-chain alkanes, but also the even-chain ones compared with other species. The effects of species and sampling time on alkane concentrations were significant, accounting for 0·912 and 0·067 of the total variance, respectively. The site effects on odd-chain alkanes were less than on even-chain. The results of principal component analysis indicated that the patterns of alkane concentrations in the five dominant species could be clearly distinguished during the whole growing season. Therefore, it should be possible to achieve accurate and precise estimations of intake and diet composition of grazing animals of the typical steppe grassland in Inner Mongolia using the alkane technique.
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Gołębiowski, M., M. Paszkiewicz, A. Grubba, D. Gąsiewska, M. I. Boguś, E. Włóka, W. Wieloch, and P. Stepnowski. "Cuticular and internal n-alkane composition of Lucilia sericata larvae, pupae, male and female imagines: application of HPLC-LLSD and GC/MS-SIM." Bulletin of Entomological Research 102, no. 4 (January 25, 2012): 453–60. http://dx.doi.org/10.1017/s0007485311000800.
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AbstractThe composition of cuticular and internal n-alkanes in Lucilia sericata larvae, pupae, and male and female imagines were studied. The cuticular and internal lipid extracts were separated by HPLC-LLSD, after which the hydrocarbon fraction was identified by GC/MS in selected ion monitoring (SIM) and total ion current (TIC) modes.The cuticular lipids of the larvae contained seven n-alkanes from C23 to C31. The major n-alkane in L. sericata larvae was C29 (42.1%). The total cuticular n-alkane content in the cuticular lipids was 31.46 μg g−1 of the insect body. The internal lipids of L. sericata larvae contained five n-alkanes ranged from C25 to C31. The most abundant compound was C27 (61.71 μg g−1 of the insect body). Eighteen n-alkanes from C14 to C31 were identified in the cuticular lipids of the pupae. The most abundant n-alkanes ranged from C25 to C31; those with odd-numbered carbon chains were particularly abundant, the major one being C29:0 (59.5%). Traces of eight cuticular n-alkanes were present. The internal lipids of L. sericata pupae contained five n-alkanes, ranging from C25 to C31. The cuticular lipids of female imagines contained 17 n-alkanes from C12 to C30. Among the cuticular n-alkanes of females, C27 (47.5%) was the most abundant compound. Four n-alkanes, with only odd-numbered carbon chains, were identified in the internal lipids of females. The lipids from both sexes of L. sericata had similar n-alkane profiles. The cuticular lipids of adult males contained 16 n-alkanes ranging from C13 to C31. C27 (47.9%) was the most abundant cuticular n-alkanes in males. The same n-alkanes only with odd-numbered carbon chains and in smaller quantities of C27 (0.1%) were also identified in the internal lipids of males.The highest amounts of total cuticular n-alkanes were detected in males and females of L. sericata (330.4 and 158.93 μg g−1 of the insect body, respectively). The quantities of total cuticular alcohols in larvae and pupae were smaller (31.46 μg g−1 and 42.08 μg g−1, respectively). The internal n-alkane contents of larvae, pupae, and male and female imagines were significantly higher than the cuticular n-alkane contents (153.53, 99.60, 360.06 and 838.76 μg g−1 of the insect body, respectively).
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Bugalho, Miguel N., John A. Milne, Robert W. Mayes, and Francisco C. Rego. "Plant-wax alkanes as seasonal markers of red deer dietary components." Canadian Journal of Zoology 83, no. 3 (March 1, 2005): 465–73. http://dx.doi.org/10.1139/z05-031.
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n-Alkanes are long-chain hydrocarbons commonly occurring in plant cuticles that can be recovered in herbivore faeces. Differences among plant species in their content of cuticular wax n-alkanes can be exploited to estimate diet composition of herbivores. n-Alkanes have been used mainly in domesticated herbivores feeding on relatively simple diets over short-term periods. Extending the method to wild herbivores feeding on seasonal complex diets is possible provided that n-alkanes act as effective dietary component markers in different seasons. The n-alkane content of browse species and herbage layer and of faeces of red deer (Cervus elaphus L., 1758) males and females in a region with a Mediterranean climate is described. Information on the n-alkane content of plant species was related to that of faeces to estimate the diet composition of red deer. Plant species had distinct n-alkane contents, some of which varied seasonally. The n-alkane content of faeces also varied seasonally and between red deer sexes. Both red deer males and females had relatively high proportion of browse in their diets during summer and of herbage layer in spring, as shown by other studies in Mediterranean environments.
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Mohamad Shahimin, Mohd Faidz, Julia M. Foght, and Tariq Siddique. "Methanogenic Biodegradation of iso-Alkanes by Indigenous Microbes from Two Different Oil Sands Tailings Ponds." Microorganisms 9, no. 8 (July 23, 2021): 1569. http://dx.doi.org/10.3390/microorganisms9081569.
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iso-Alkanes, a major fraction of the solvents used in bitumen extraction from oil sand ores, are slow to biodegrade in anaerobic tailings ponds. We investigated methanogenic biodegradation of iso-alkane mixtures comprising either three (2-methylbutane, 2-methylpentane, 3-methylpentane) or five (2-methylbutane, 2-methylpentane, 2-methylhexane, 2-methylheptane, 2-methyloctane) iso-alkanes representing paraffinic and naphtha solvents, respectively. Mature fine tailings (MFT) collected from two tailings ponds, having different residual solvents (paraffinic solvent in Canadian Natural Upgrading Limited (CNUL) and naphtha in Canadian Natural Resources Limited (CNRL)), were amended separately with the two mixtures and incubated in microcosms for ~1600 d. The indigenous microbes in CNUL MFT produced methane from the three-iso-alkane mixture after a lag of ~200 d, completely depleting 2-methylpentane while partially depleting 2-methylbutane and 3-methylpentane. CNRL MFT exhibited a similar degradation pattern for the three iso-alkanes after a lag phase of ~700 d, but required 1200 d before beginning to produce methane from the five-iso-alkane mixture, preferentially depleting components in the order of decreasing carbon chain length. Peptococcaceae members were key iso-alkane-degraders in both CNUL and CNRL MFT but were associated with different archaeal partners. Co-dominance of acetoclastic (Methanosaeta) and hydrogenotrophic (Methanolinea and Methanoregula) methanogens was observed in CNUL MFT during biodegradation of three-iso-alkanes whereas CNRL MFT was enriched in Methanoregula during biodegradation of three-iso-alkanes and in Methanosaeta with five-iso-alkanes. This study highlights the different responses of indigenous methanogenic microbial communities in different oil sands tailings ponds to iso-alkanes.
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So, Chi Ming, and L. Y. Young. "Initial Reactions in Anaerobic Alkane Degradation by a Sulfate Reducer, Strain AK-01." Applied and Environmental Microbiology 65, no. 12 (December 1, 1999): 5532–40. http://dx.doi.org/10.1128/aem.65.12.5532-5540.1999.
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ABSTRACT An alkane-degrading, sulfate-reducing bacterial strain, AK-01, isolated from a petroleum-contaminated sediment was studied to elucidate its mechanism of alkane metabolism. Total cellular fatty acids of AK-01 were predominantly C even when it was grown on C-even alkanes and were predominantly C odd when grown on C-odd alkanes, suggesting that the bacterium anaerobically oxidizes alkanes to fatty acids. Among these fatty acids, some 2-, 4-, and 6-methylated fatty acids were specifically found only when AK-01 was grown on alkanes, and their chain lengths always correlated with those of the alkanes. When [1,2-13C2]hexadecane or perdeuterated pentadecane was used as the growth substrate, 13C-labeled 2-Me-16:0, 4-Me-18:0, and 6-Me-20:0 fatty acids or deuterated 2-Me-15:0, 4-Me-17:0, and 6-Me-19:0 fatty acids were recovered, respectively, confirming that these monomethylated fatty acids were alkane derived. Examination of the 13C-labeled 2-, 4-, and 6-methylated fatty acids by mass spectrometry showed that each of them contained two 13C atoms, located at the methyl group and the adjacent carbon, thus indicating that the methyl group was the original terminal carbon of the [1,2-13C2]hexadecane. For perdeuterated pentadecane, the presence of three deuterium atoms, on the methyl group and its adjacent carbon, in each of the deuterated 2-, 4-, and 6-methylated fatty acids further supported the hypothesis that the methyl group was the terminal carbon of the alkane. Thus, exogenous carbon appears to be initially added to an alkane subterminally at the C-2 position such that the original terminal carbon of the alkane becomes a methyl group on the subsequently formed fatty acid. The carbon addition reaction, however, does not appear to be a direct carboxylation of inorganic bicarbonate. A pathway for anaerobic metabolism of alkanes by strain AK-01 is proposed.
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Gibu, Kasai, Ikawa, Akiyama, and Fukuda. "Characterization and Transcriptional Regulation of n-Alkane Hydroxylase Gene Cluster of Rhodococcus jostii RHA1." Microorganisms 7, no. 11 (October 23, 2019): 479. http://dx.doi.org/10.3390/microorganisms7110479.
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Gram-positive actinomycete Rhodococcus jostii RHA1 is able to grow on C10 to C19 n-alkanes as a sole source of carbon and energy. To clarify, the n-alkane utilization pathway—a cluster of 5 genes (alkBrubA1A2BalkU) which appeared to be involved in n-alkane degradation—was identified and the transcriptional regulation of these genes was characterized. Reverse transcription-PCR analyses revealed that these genes constituted an operon and were transcribed in the presence of n-alkane. Inactivation of alkB led to the absence of the ability to utilize n-undecane. The alkB mutation resulted in reduction of growth rates on C10 and C12 n-alkanes; however, growths on C13 to C19 n-alkanes were not affected by this mutation. These results suggested that alkB was essential for the utilization of C10 to C12 n-alkanes. Inactivation of alkU showed the constitutive expression of alkB. Purified AlkU is able to bind to the putative promoter region of alkB, suggesting that AlkU played a role in repression of the transcription of alk operon. The results of this study indicated that alkB was involved in the medium-chain n-alkanes degradation of strain RHA1 and the transcription of alk operon was negatively regulated by alkU-encoded regulator. This report is important to understand the n-alkane degradation pathway of R. jostii, including the transcriptional regulation of alk gene cluster.
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Nie, Yong, Jieliang Liang, Hui Fang, Yue-Qin Tang, and Xiao-Lei Wu. "Two Novel Alkane Hydroxylase-Rubredoxin Fusion Genes Isolated from a Dietzia Bacterium and the Functions of Fused Rubredoxin Domains in Long-Chainn-Alkane Degradation." Applied and Environmental Microbiology 77, no. 20 (August 26, 2011): 7279–88. http://dx.doi.org/10.1128/aem.00203-11.
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ABSTRACTTwo alkane hydroxylase-rubredoxin fusion gene homologs (alkW1andalkW2) were cloned from aDietziastrain, designated DQ12-45-1b, which can grow on crude oil andn-alkanes ranging in length from 6 to 40 carbon atoms as sole carbon sources. Both AlkW1 and AlkW2 have an integral-membrane alkane monooxygenase (AlkB) conserved domain and a rubredoxin (Rd) conserved domain which are fused together. Phylogenetic analysis showed that these two AlkB-fused Rd domains formed a novel third cluster with all the Rds from the alkane hydroxylase-rubredoxin fusion gene clusters in Gram-positive bacteria and that this third cluster was distant from the known AlkG1- and AlkG2-type Rds. Expression of thealkW1gene in DQ12-45-1b was induced when cells were grown on C8to C32n-alkanes as sole carbon sources, but expression of thealkW2gene was not detected. Functional heterologous expression in analkBdeletion mutant ofPseudomonas fluorescensKOB2Δ1 suggested thealkW1could restore the growth of KOB2Δ1 on C14and C16n-alkanes and induce faster growth on C18to C32n-alkanes thanalkW1ΔRd, the Rd domain deletion mutant gene ofalkW1, which also caused faster growth than KOB2Δ1 itself. In addition, the artificial fusion of AlkB from the Gram-negativeP. fluorescensCHA0 and the Rds from both Gram-negativeP. fluorescensCHA0 and Gram-positiveDietziasp. DQ12-45-1b significantly increased the degradation of C32alkane compared to that seen with AlkB itself. In conclusion, thealkW1gene cloned fromDietziaspecies encoded an alkane hydroxylase which increased growth on and degradation ofn-alkanes up to C32in length, with its fused rubredoxin domain being necessary to maintain the functions. In addition, the fusion of alkane hydroxylase and rubredoxin genes from both Gram-positive and -negative bacteria can increase the degradation of long-chainn-alkanes (such as C32) in the Gram-negative bacterium.
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Laredo, M. A., G. D. Simpson, D. J. Minson, and C. G. Orpin. "The potential for using n-alkanes in tropical forages as a marker for the determination of dry matter by grazing ruminants." Journal of Agricultural Science 117, no. 3 (December 1991): 355–61. http://dx.doi.org/10.1017/s0021859600067101.
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SUMMARYThe intake of temperate forages by herbivores can be determined using the C33 alkane naturally present in the forage and dosed C32 alkane. To determine whether the technique can be used with tropical forages, the concentrations of C33 alkane were determined in seven species.The leaves of Brachiaria decumbens, Digitaria decumbens, Pennisetum glaucum and Stylosanthes scabra contained sufficient C33 alkane (> 50 mg/kg DM) for the estimation of dry matter intake. Low concentrations of C33 alkane were found in the leaves of Setaria sphacelata, Sorghum sp. and Leucaena leucocephala. Setaria sphacelata was found to contain high concentrations of C27 alkane and therefore intake could be estimated by using C28 as the dosed alkane although the intake would possibly then be underestimated by c. 8%. Leaves of Sorghum sp. contained > 50 mg C31 alkane/kg DM and, with C32 as the dosed alkane, intake would possibly be underestimated by c. 5%. Leucaena leucocephala contained insufficient alkanes to estimate forage intake. The concentration of n-alkanes in Pennisetum glaucum and Sorghum sp. leaves decreased with age.It was concluded that some tropical forages contain insufficient C33 alkane for the measurement of intake by the double alkane technique. In these species, a shorter chain length alkane can sometimes be used, but only with a reduction in accuracy in estimating intake.
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van Beilen, Jan B., Enrico G. Funhoff, Alexander van Loon, Andrea Just, Leo Kaysser, Manuel Bouza, René Holtackers, Martina Röthlisberger, Zhi Li, and Bernard Witholt. "Cytochrome P450 Alkane Hydroxylases of the CYP153 Family Are Common in Alkane-Degrading Eubacteria Lacking Integral Membrane Alkane Hydroxylases." Applied and Environmental Microbiology 72, no. 1 (January 2006): 59–65. http://dx.doi.org/10.1128/aem.72.1.59-65.2006.
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ABSTRACT Several strains that grow on medium-chain-length alkanes and catalyze interesting hydroxylation and epoxidation reactions do not possess integral membrane nonheme iron alkane hydroxylases. Using PCR, we show that most of these strains possess enzymes related to CYP153A1 and CYP153A6, cytochrome P450 enzymes that were characterized as alkane hydroxylases. A vector for the polycistronic coexpression of individual CYP153 genes with a ferredoxin gene and a ferredoxin reductase gene was constructed. Seven of the 11 CYP153 genes tested allowed Pseudomonas putida GPo12 recombinants to grow well on alkanes, providing evidence that the newly cloned P450s are indeed alkane hydroxylases.
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OLIVÁN, M., and K. OSORO. "Effect of temperature on alkane extraction from faeces and herbage." Journal of Agricultural Science 132, no. 3 (May 1999): 305–11. http://dx.doi.org/10.1017/s0021859699006358.
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The solvent extraction of alkanes from faeces and herbage samples at two different temperatures (cold: 15–25°C and hot: 65°C) was studied in four samples of different matrix types (cattle faeces, sheep faeces, hill grass and heather), in two experiments performed at Villaviciosa, Asturias, Spain in 1994. Two internal standards (IS) of different chain length (C22 and C34) were used to estimate alkane concentrations. Significant differences were detected in alkane extraction derived from temperature of extraction, IS and sample matrix. At the cold temperature, long-chain alkane extraction was not complete, resulting in errors in the estimation of alkane concentration when a long-chain alkane (C34) was used as the only internal standard. However, under hot extraction, long- chain alkanes were completely extracted by the heptane, although estimates made with C22 or C34 as IS were not identical. These results suggest that it would be appropriate to use two internal standards with short and long carbon chain, such as C22 and C34, in routine analyses to establish the completeness of alkane extraction, even under hot conditions, by calculating the relative ratio of both IS in extracts compared to the original C22[ratio ]C34 ratio added to the samples. Any increase or decrease in expected peak areas could be adjusted for all the alkanes in the extracts, and the accuracy of alkane concentration measurements (and therefore the reliability of estimates of intake and especially of diet selection) would be improved.
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Dove, H., and RW Mayes. "The use of plant wax alkanes as marker substances in studies of the nutrition of herbivores: a review." Australian Journal of Agricultural Research 42, no. 6 (1991): 913. http://dx.doi.org/10.1071/ar9910913.
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This review discusses the potential use of plant wax components, especially n-alkanes, as markers for estimating herbage intake, estimating the botanical composition of consumed herbage and studying digesta kinetics. Previous approaches to making these measurements are discussed briefly. Attention is drawn to the fact that current methods for estimating intake do not adequately allow for differences between individual animals. It is also suggested that the markers currently used to estimate botanical composition or study digesta kinetics are inadequate. The nature of the chemical constituents of plant waxes is briefly discussed and the concept of using alkanes to estimate intake is introduced. Particular emphasis is given to the fact that although the recovery of alkanes in faeces is not complete, intake can still be estimated using a pair of alkanes (one natural, one dosed) provided these have similar faecal recoveries. The accuracy of estimation of intake is discussed in terms of: obtaining a representative sample of herbage; alkane dosing and faecal sampling procedures; validity of the assumption of similar recoveries for the natural and dosed alkanes; sample preparation and analysis. Published comparisons of estimated and actual intakes are presented, with the conclusion that satisfactory results are obtained if intake is estimated using natural C33 alkane and dosed C32 alkane. The use of the different patterns of alkanes in herbage species, as a means of estimating botanical composition, is then discussed. Results are presented showing this can be done successfully with herbage mixtures or oesophageal extrusa. Procedures are then described for making the corrections for incomplete faecal alkane recovery, necessary to estimate the botanical composition of the herbage consumed by the free-grazing animal. This allows the quantification of the intake of individual plant species by individual animals, and it is suggested that this can be achieved without the need for oesophageally-fistulated (OF) animals. Differences in alkane levels between plant parts within a species are then discussed. It is suggested that these can lead to error in the estimation of intake, if OF animals should consume plant parts different from those consumed by the test animals. However, it is also suggested that differences in alkane levels between plant parts can be used to quantify the intake of these parts, in a manner analogous to the estimation of the intake of individual plant species. The usefulness of alkanes in studies of digesta kinetics is then discussed, principally in relation to the natural alkanes, which remain intimately associated with plant particles in the gut. It is suggested that natural alkanes could prove excellent markers for studies of particle breakdown and digesta flow. The preparation of natural 14C-labelled alkane, for use as a pulse dose in mean retention time studies, is also discussed.
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Charmley, E., D. R. Ouellet, D. M. Veira, R. Michaud, J. L. Duynisveld, and H. V. Petit. "Estimation of intake and digestibility of silage by beef steers using a controlled release capsule of n-alkanes." Canadian Journal of Animal Science 83, no. 4 (December 1, 2003): 761–68. http://dx.doi.org/10.4141/a03-018.
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Twelve beef steers were fed a grass-legume silage either ad libitum or at 70% of ad libitum feeding. Intake and digestibility were measured directly or predicted using the alkane ratio technique. The C32 and C36 alkanes were delivered via a controlled release capsule (CRC) in the rumen. Level of feeding had no effect on digestibility (P > 0.05) but dry matter (DM) intake tended to be greater for steers fed ad libitum (P = 0.08). The release of alkanes from the CRC was erratic and 20% greater than expected. This influenced the exogenous to endogenous alkane ratios. Estimates of intake were therefore derived using both the expected and actual (determined from total collection of feces and their alkane analysis) exogenous alkane release rates. Estimated intakes based on the manufacturers’ release rate were underestimated and associated with high standard errors. For cattle fed restricted silage, estimated intakes obtained with C31:C32, C33:C32 and C33:C36 alkane pairs and using actual measured release rates of exogenous markers were associated with lower standard errors and averaged 87, 102 and 103% of actual values, respectively. For ad libitum-fed cattle the corresponding values were 81, 96 and 96% of actual values. There was no significant difference between actual and estimated DM intake when the C33:C32 and C36:C32 alkane pairs were used. The precision of intake estimates using manufacturers release rates for exogenous alkanes was poor, as evidenced by significant discrepancies (P < 0.05 for four of six estimates) between observed and predicted values averaging 2.26 kg or 30% of DM intake. However, when measured exogenous alkane release rates were used, standard errors were reduced and discrepancies for estimates using C33:C32 and C33:C326 were only 0.4 kg or 6% of DM intake. Fecal recovery of C27, C29, C31 and C33 alkanes was 73.4, 92.7, 85.6 and 100%, respectively. Both C29 and C33 gave good estimates of digestibility because of high recovery. Observed and estimated values were not significantly different. It is concluded that exogenous alkane release from CRCs was not satisfactorily consistent. Reliable estimates of intake could only be made if actual release rate was known. Endogenous alkanes can be used for determination of digestibility, provided fecal recovery is known. Key words: Beef, silage, alkane, intake, digestibility
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Ferreira, L. M. M., M. Oliván, M. A. M. Rodrigues, A. Dias-da-Silva, and K. Osoro. "The use of alkanes as markers for estimating diet composition in sheep and goats." BSAP Occasional Publication 34 (2006): 15–20. http://dx.doi.org/10.1017/s1463981500042205.
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SummaryAn experiment was carried out to evaluate the use of alkanes for estimating diet composition of goats and sheep offered three different dietary treatments. Twelve animals as two groups of 4 crossbred goats (G1, 24 kg live weight; G2, 22 kg) and 4 crossbred sheep (S, 26 kg live weight), were housed in metabolism pens. Animals were offered daily a total of 1 kg DM/100 kg live weight. G1 received 70% ryegrass (Lolium perenne) and 30% gorse (Ulex gallii), G2 received 70% ryegrass and 30% heather (Erica sp.) and S group ate 100% ryegrass. Diet composition was estimated from the alkane concentrations (using all alkanes from C23 to C36 or only odd-chain alkanes C27, C29, C31 and C33) in diet and faeces (with or without correction for incomplete faecal recoveries) using least-squares procedures.Dietary treatment and animal species significantly affected alkane faecal recoveries, except for C24 and C36. When applying the faecal recovery corrections, there were no significant differences between measured proportions of dietary components and those estimated using all alkanes or odd-chain alkanes. In contrast, the proportions calculated without faecal recovery correction differed significantly (P<0.05) from the actual proportions and over-estimated the amount in the diet of those plant components with higher concentrations of long-chain alkanes (Erica sp. and Lolium perenne). The results indicate that alkanes are useful markers to estimate diet composition, however, it was observed that animal species and diet composition influenced the faecal recovery of alkanes. This suggests that the use of the alkane methodology for estimating the diet selection of grazing animals should be preceded by a calculation of the actual alkane faecal recoveries for each experimental condition.
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Thontowi, Ahmad, Elvi Yetti, and Yopi Yopi. "Medium Chain and Long Chain Alkanes Hydroxylase Producing Whole Cell Biocatalyst From Marine Bacteria." ANNALES BOGORIENSES 22, no. 1 (September 10, 2018): 12. http://dx.doi.org/10.14203/ab.v22i1.329.
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Alkanes are major component of crude oil that could be hydrolyzed by the enzyme of alkane hydroxylase. The are three types of alkane hydroxylase based on the chain length of alkane such as short-chain length/SCL (C2-C4), medium-chain length/MCL (C5-C17), and long-chain length/LCL (C>18). The aims of this study were to characterize and identify alkanes-degrading bacteria from these bacteria. The 30 strains from marine were grown on MCL (Pentane-C5H12, Decane-C10H22, and Pentadecane-C15H32) and LCL (n-Paraffin-C12H19C17 and branch of Pristane-C19H40). The study showed twenty-nine isolates have the ability to degrade alkanes compounds, whereas 14 isolates have grown ability on MCL and LCL medium, 11 isolates have the ability to grow on MCL and n-LCL, 3 isolates have the ability only to grow on MCL medium and 1 isolate has the ability only grow on n-LCL medium. The growth test result indicated that 29 isolates have medium-chain alkane monooxygenase and long-chain alkane hydroxylase. Based on 16S rDNA gene analysis, we obtained twenty nine of oil- degrading bacteria, namely a-proteobacteria (57 %), g-proteobacteria (30 %), Flavobacteria (7 %), Bacilli (3%) and Propionibacteriales (3 %). g-Proteobacteria and a-proteobacteria which seems to play an important role in the alkane biodegradation.
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Thontowi, Ahmad, Elvi Yetti, and Yopi Yopi. "Medium Chain and Long Chain Alkanes Hydroxylase Producing Whole Cell Biocatalyst From Marine Bacteria." ANNALES BOGORIENSES 22, no. 1 (June 29, 2018): 12. http://dx.doi.org/10.14203/ann.bogor.2018.v22.n1.12-19.
Full textAbstract:
Alkanes are major component of crude oil that could be hydrolyzed by the enzyme of alkane hydroxylase. The are three types of alkane hydroxylase based on the chain length of alkane such as short-chain length/SCL (C2-C4), medium-chain length/MCL (C5-C17), and long-chain length/LCL (C>18). The aims of this study were to characterize and identify alkanes-degrading bacteria from these bacteria. The 30 strains from marine were grown on MCL (Pentane-C5H12, Decane-C10H22, and Pentadecane-C15H32) and LCL (n-Paraffin-C12H19C17 and branch of Pristane-C19H40). The study showed twenty-nine isolates have the ability to degrade alkanes compounds, whereas 14 isolates have grown ability on MCL and LCL medium, 11 isolates have the ability to grow on MCL and n-LCL, 3 isolates have the ability only to grow on MCL medium and 1 isolate has the ability only grow on n-LCL medium. The growth test result indicated that 29 isolates have medium-chain alkane monooxygenase and long-chain alkane hydroxylase. Based on 16S rDNA gene analysis, we obtained twenty nine of oil- degrading bacteria, namely a-proteobacteria (57 %), g-proteobacteria (30 %), Flavobacteria (7 %), Bacilli (3%) and Propionibacteriales (3 %). g-Proteobacteria and a-proteobacteria which seems to play an important role in the alkane biodegradation.
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Lo Piccolo, Luca, Claudio De Pasquale, Roberta Fodale, Anna Maria Puglia, and Paola Quatrini. "Involvement of an Alkane Hydroxylase System ofGordoniasp. Strain SoCg in Degradation of Solidn-Alkanes." Applied and Environmental Microbiology 77, no. 4 (December 23, 2010): 1204–13. http://dx.doi.org/10.1128/aem.02180-10.
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ABSTRACTEnzymes involved in oxidation of long-chainn-alkanes are still not well known, especially those in Gram-positive bacteria. This work describes the alkane degradation system of then-alkane degrader actinobacteriumGordoniasp. strain SoCg, which is able to grow onn-alkanes from dodecane (C12) to hexatriacontane (C36) as the sole C source. SoCg harbors in its chromosome a singlealklocus carrying six open reading frames (ORFs), which shows 78 to 79% identity with the alkane hydroxylase (AH)-encoding systems of other alkane-degrading actinobacteria. Quantitative reverse transcription-PCR showed that the genes encoding AlkB (alkane 1-monooxygenase), RubA3 (rubredoxin), RubA4 (rubredoxin), and RubB (rubredoxin reductase) were induced by bothn-hexadecane andn-triacontane, which were chosen as representative long-chain liquid and solidn-alkane molecules, respectively. Biotransformation ofn-hexadecane into the corresponding 1-hexadecanol was detected by solid-phase microextraction coupled with gas chromatography-mass spectrometry (SPME/GC-MS) analysis. TheGordoniaSoCgalkBwas heterologously expressed inEscherichia coliBL21 and inStreptomyces coelicolorM145, and both hosts acquired the ability to transformn-hexadecane into 1-hexadecanol, but the corresponding long-chain alcohol was never detected onn-triacontane. However, the recombinantS. coelicolorM145-AH, expressing theGordonia alkBgene, was able to grow onn-triacontane as the sole C source. A SoCgalkBdisruption mutant that is completely unable to grow onn-triacontane was obtained, demonstrating the role of an AlkB-type AH system in degradation of solidn-alkanes.
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Chen, W., R. D. B. Lefroy, G. J. Blair, and J. M. Scott. "Field variations in alkane signatures among plant species in ‘degraded’ and perennial pastures on the Northern Tablelands of New South Wales." Australian Journal of Agricultural Research 49, no. 2 (1998): 263. http://dx.doi.org/10.1071/a97022.
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Differences in concentrations of n-alkanes in the cuticular waxes of plants can be used to estimate the species composition of herbage mixtures or the diet consumed by grazing animals. The objectives of this study were (i) to provide information on the n-alkane (C25-C35) ‘signatures’ or patterns of pasture species occurring in ‘degraded’ and perennial pastures of the Northern Tablelands, New South Wales, and (ii) to examine the extent of the field variation in the signatures. There were considerable differences in odd-numbered alkanes and in their total content between species. There were also significant differences in n-alkane concentrations among species within grasses, legumes, and weeds. For the individual odd-numbered alkanes, differences between species accounted for 87-93% of the total variance in alkane concentration over 3 samplings. Variable results for the temporal effect suggest that time-specific herbage samples are needed in animal diet studies. Analyses of the spatial effect indicate that random cuts over each treatment plot can obtain representative samples of each species. Multivariate statistical analyses using principal component and discriminant analyses indicated that the patterns of alkanes in species occurring on both degraded and perennial pastures were readily distinguishable. These results confirmed that the alkane technique could be used for estimation of diet composition in grazing sheep on the Northern Tablelands, NSW, where differences in n-alkane signatures between species were sufficient and persistent over time.
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Bliedtner, Marcel, Hans von Suchodoletz, Imke Schäfer, Caroline Welte, Gary Salazar, Sönke Szidat, Mischa Haas, Nathalie Dubois, and Roland Zech. "Age and origin of leaf wax <i>n</i>-alkanes in fluvial sediment–paleosol sequences and implications for paleoenvironmental reconstructions." Hydrology and Earth System Sciences 24, no. 4 (April 28, 2020): 2105–20. http://dx.doi.org/10.5194/hess-24-2105-2020.
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Abstract. Leaf wax n-alkanes are increasingly used for quantitative paleoenvironmental reconstructions. However, this is complicated in sediment archives with associated hydrological catchments since the stored n-alkanes can have different ages and origins. 14C dating of the n-alkanes yields independent age information for these proxies, allowing their correct paleoenvironmental interpretation. This also holds true for fluvial sediment–paleosol sequences (FSPSs) that integrate two different n-alkane signals: (i) a catchment signal in fluvial sediments and (ii) an on-site signal from local biomass that increasingly dominates (paleo)soils with time. Therefore, the age and origin of n-alkanes in FSPSs are complex: in fluvial sediment layers they can be pre-aged and reworked when originating from eroded catchment soils or from organic-rich sediment rocks in the catchment. In (paleo)soils, besides an inherited contribution from the catchment, they were formed on-site by local biomass during pedogenesis. Depending on the different relative contributions from these sources, the n-alkane signal from an FSPS shows variable age offsets between its formation and final deposition. During this study, we applied compound-class 14C dating to n-alkanes from an FSPS along the upper Alazani in eastern Georgia. Our results show that preheating the n-alkanes with 120 ∘C for 8 h before 14C dating effectively removed the shorter chains (<C25) that partly originate from n-alkanes from Jurassic black clay shales in the upper catchment. The remaining petrogenic contributions on the longer chains (≥C25) were corrected for by using a constant correction factor that was based on the n-alkane concentrations in a black clay shale sample from the upper catchment. Due to different degrees of pre-aging and reworking, the corrected leaf wax n-alkane ages still indicate relatively large age offsets between n-alkane formation and deposition: while intensively developed (paleo)soils showed no age offsets due to a dominance of leaf wax n-alkanes produced on-site, less intensively developed paleosols showed much larger age offsets due to larger proportions of inherited leaf wax n-alkanes from the fluvial parent material. Accordingly, age offsets in nonpedogenic fluvial sediments were largest and strongly increased after ∼4 ka cal BP. The leaf wax n-alkane homolog distribution from intensively developed (paleo)soils indicates a local dominance of grasses and herbs throughout the Holocene, which was most likely caused by anthropogenic activity. The leaf wax n-alkanes from fluvial sediments show a dominance of deciduous trees and shrubs as well as grasses and herbs in different parts of the catchment between ∼8 and ∼5.6 ka cal BP. Since no older deciduous tree- or shrub-derived n-alkanes were dated, this seems to confirm a delayed regional postglacial reforestation of parts of the catchment compared with western and central Europe.
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Tani, Akio, Takeru Ishige, Yasuyoshi Sakai, and Nobuo Kato. "Gene Structures and Regulation of the Alkane Hydroxylase Complex in Acinetobacter sp. Strain M-1." Journal of Bacteriology 183, no. 5 (March 1, 2001): 1819–23. http://dx.doi.org/10.1128/jb.183.5.1819-1823.2001.
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ABSTRACT In the long-chain n-alkane degraderAcinetobacter sp. strain M-1, two alkane hydroxylase complexes are switched by controlling the expression of twon-alkane hydroxylase-encoding genes in response to the chain length of n-alkanes, while rubredoxin and rubredoxin ruductase are encoded by a single gene and expressed constitutively.
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Endoh-Yamagami, Setsu, Kiyoshi Hirakawa, Daisuke Morioka, Ryouichi Fukuda, and Akinori Ohta. "Basic Helix-Loop-Helix Transcription Factor Heterocomplex of Yas1p and Yas2p Regulates Cytochrome P450 Expression in Response to Alkanes in the Yeast Yarrowia lipolytica." Eukaryotic Cell 6, no. 4 (February 23, 2007): 734–43. http://dx.doi.org/10.1128/ec.00412-06.
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ABSTRACT The expression of the ALK1 gene, which encodes cytochrome P450, catalyzing the first step of alkane oxidation in the alkane-assimilating yeast Yarrowia lipolytica, is highly regulated and can be induced by alkanes. Previously, we identified a cis-acting element (alkane-responsive element 1 [ARE1]) in the ALK1 promoter. We showed that a basic helix-loop-helix (bHLH) protein, Yas1p, binds to ARE1 in vivo and mediates alkane-dependent transcription induction. Yas1p, however, does not bind to ARE1 by itself in vitro, suggesting that Yas1p requires another bHLH protein partner for its DNA binding, as many bHLH transcription factors function by forming heterodimers. To identify such a binding partner of Yas1p, here we screened open reading frames encoding proteins with the bHLH motif from the Y. lipolytica genome database and identified the YAS2 gene. The deletion of the YAS2 gene abolished the alkane-responsive induction of ALK1 transcription and the growth of the yeast on alkanes. We revealed that Yas2p has transactivation activity. Furthermore, Yas1p and Yas2p formed a protein complex that was required for the binding of these proteins to ARE1. These findings allow us to postulate a model in which bHLH transcription factors Yas1p and Yas2p form a heterocomplex and mediate the transcription induction in response to alkanes.
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Ferraz de Oliveira, M. I., A. P. Trigo, J. A. Neves, and M. Cancela d´Abreu. "Validation of the n–alkane technique to measure intake and digestibility in Alentejano pigs under “Montanheira”." BSAP Occasional Publication 34 (2006): 55–61. http://dx.doi.org/10.1017/s1463981500042266.
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SummaryIn the traditional silvo–pastoral system, Alentejano pigs are fattened with acorns and pasture. Although this production system (“Montanheira”) has been characterised, there is a lack of knowledge on intake and digestibility of the diet, mainly due to the absence of tested methodologies in pigs. The n–alkane technique, extensively used in ruminants to estimate diet intake and digestibilitiy, has had less use in pigs. The objective of this experiment was to validate the n–alkane technique in Alentejano pigs. Faecal recoveries of natural and dosed n-alkanes, the diurnal variation of faecal n–alkane concentration, and the time span required to reach a steady state excretion of dosed alkanes were determined. Eight male Alentejano pigs (54.4±9.8 kg LW) were randomly allocated to two groups and placed in metabolic cages. They were fed 0.7 kg of pasture and 0.7kg of ground acorns daily as two meals. Pigs in Group-1 were given once daily artificial C32(40mg/d) and C36(40 mg/d) and those in Group-2 the same alkanes as two daily doses of 20 mg. Steady state excretion of both alkanes was reached 3 days after first dosing. Although no difference (P>0.05) was observed between treatments, the coefficient of variation of feacal alkane concentration when dosed twice daily was generally lower than when dosed once daily. Mean faecal recoveries of n–alkanes increased with increasing carbon-chain length (C25to C36) from 38 to 69%, but were not significantly different from C29, C32, C33and C36(mean 0.694 SEM 0.067). Faecal nalkanes in samples collected every four hours for three days showed no diurnal variation in patterns of excretion apart from a higher concentration of C324 hours after dosing once daily. However variation between animals was lower when artificial alkanes were dosed twice daily than when once daily. The results indicate that the n–alkane techique may be used to estimate intake and digestibility under “Montanheira”, although further validation work needs to be done.
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Wilson, H., A. G. Sinclair, F. D. DeB Hovell, R. W. Mayes, and S. A. Edwards. "Validation of the n-alkane technique for measuring herbage intake in sows." Proceedings of the British Society of Animal Science 1999 (1999): 177. http://dx.doi.org/10.1017/s175275620000332x.
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N-alkanes are components of plant cuticular wax which have been successfully used as markers for the estimation of grass intake and digestibility in grazing ruminants (Dove and Mayes, 1991). Natural n-alkanes are predominately odd chain, and a known dose of an artificial even chain n-alkane (normally c32 or c36) is used to enable intake to be measured. Dietary n-alkanes may behave differently in the gastro-intestinal tract of ruminants and non-ruminants (Mayes et al, 1995). Therefore, in order to utilise this methodology in studies of outdoor pigs, this experiment was carried out to validate the faecal recovery of n-alkanes in this species. Since n-alkanes are soluble in lipid, which is often incorporated at high inclusion levels in pig diets, the experiment was also designed to determine whether n-alkane recovery is influenced by dietary lipid content.
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HAMELEERS, A., and R. W. MAYES. "The use of n-alkanes to estimate supplementary grass silage intake in grazing dairy cows." Journal of Agricultural Science 131, no. 2 (September 1998): 205–9. http://dx.doi.org/10.1017/s0021859698005760.
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A grazing experiment was carried out using 18 Holstein/Friesian dairy cows at the Scottish Agricultural College, Crichton Royal Farm in 1991, to investigate the use of n-alkanes for estimating supplementary grass silage intake by grazing dairy cows. Two groups of animals grazed perennial ryegrass swards and were offered a supplement, consisting of a perennial ryegrass silage, twice daily after milking. Mean group silage intakes were measured daily during the last 5 days of a 12-day experimental period and individual silage intakes were estimated using n-alkanes. Animals were dosed twice daily with paper pellets containing dotriacontane (C32). The silage was marked with hexatriacontane (C36). The mean silage intake, estimated by weighing, was 6·8 kg DM per day. The mean estimated silage intakes were 6·9, 8·7 and 8·3 kg DM per day respectively using odd-chain n-alkanes in the C27−C35 range of naturally occurring alkanes, the odd-chain n-alkanes in the C27−C35 range with C36, and C36 by itself. No significant differences were found due to sampling routine (morning or afternoon) when using the naturally occurring n-alkanes but significant differences did exist when using the C36 alkane in the calculation of supplement intake. The results indicate that the n-alkane technique can be used to estimate the supplementary silage intake of grazing dairy cows using naturally occurring n-alkane patterns.
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Marı́n, Mercedes M., Theo H. M. Smits, Jan B. van Beilen, and Fernando Rojo. "The Alkane Hydroxylase Gene of Burkholderia cepacia RR10 Is under Catabolite Repression Control." Journal of Bacteriology 183, no. 14 (July 15, 2001): 4202–9. http://dx.doi.org/10.1128/jb.183.14.4202-4209.2001.
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ABSTRACT In many microorganisms the first step for alkane degradation is the terminal oxidation of the molecule by an alkane hydroxylase. We report the characterization of a gene coding for an alkane hydroxylase in aBurkholderia cepacia strain isolated from an oil-contaminated site. The protein encoded showed similarity to other known or predicted bacterial alkane hydroxylases, although it clustered on a separate branch together with the predicted alkane hydroxylase of a Mycobacterium tuberculosis strain. Introduction of the cloned B. cepacia gene into an alkane hydroxylase knockout mutant of Pseudomonas fluorescens CHAO restored its ability to grow on alkanes, which confirms that the gene analyzed encodes a functional alkane hydroxylase. The gene, which was namedalkB, is not linked to other genes of the alkane oxidation pathway. Its promoter was identified, and its expression was analyzed under different growth conditions. Transcription was induced by alkanes of chain lengths containing 12 to at least 30 carbon atoms as well as by alkanols. Although the gene was efficiently expressed during exponential growth, transcription increased about fivefold when cells approached stationary phase, a characteristic not shared by the few alkane degraders whose regulation has been studied. Expression of the alkB gene was under carbon catabolite repression when cells were cultured in the presence of several organic acids and sugars or in a complex (rich) medium. The catabolic repression process showed several characteristics that are clearly different from what has been observed in other alkane degradation pathways.
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Charmley, E., and H. Dove. "Using plant wax markers to estimate diet composition and intakes of mixed forages in sheep by feeding a known amount of alkane-labelled supplement." Australian Journal of Agricultural Research 58, no. 12 (2007): 1215. http://dx.doi.org/10.1071/ar07187.
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The feeding of known amounts of supplements to grazing animals can be accomplished relatively easily. If the supplement and the other diet components have distinctive profiles of cuticular wax n-alkanes, then the supplement intake and the alkane profiles of the supplement, other dietary components and faeces can be used to estimate the proportions and hence intakes of several forages by the grazing animal. However, this method requires knowledge of recoveries of n-alkanes in faeces. Twenty four wethers were fed one of four diets comprising equal combinations of 1, 2, 3 or 4 forages. Forages used were subterranean clover, phalaris, annual ryegrass and wheat straw. Forages were chopped using a chaff cutter and fed with solvent-extracted cottonseed meal (CSM) labelled with beeswax and synthetic C28 alkane to provide a characteristic alkane profile. Faecal grab samples were taken from sheep from 14 to 23 days after administration of an intra-ruminal controlled-release device (CRD) containing 1 g of each of C32 and C36 alkane. Total faeces were collected from half the sheep on each treatment in order to measure alkane recoveries in individual sheep. Faecal concentrations of the n-alkanes C25 to C31 and C33 were corrected for recovery using the individual sheep value, the treatment mean or the grand mean for all four treatments. Dietary compositions were then estimated from corrected faecal concentrations of n-alkanes using a least-squares procedure and, together with the known supplement intakes, were used to estimate the intakes of all other diet components. Estimates from this ‘labelled supplement’ method were compared with the amounts fed or those estimated using the alkanes derived from the CRD. The labelled supplement method accurately and precisely estimated dietary component proportions and intake for all treatments when measured recoveries for individual sheep were used. Precision declined when recovery was based on estimated recoveries for treatment means or the grand mean. Estimates of intake based on dietary C33 and the measured release rates of C32 or C36 alkanes from the CRD did not differ from measured intakes. Estimates based on the C32 : C31 alkane pair over-estimated intake. Estimates of whole-diet digestibility based on the various ways of estimating intake were all very close to the digestibilities calculated from directly-measured intakes and faecal outputs. It is concluded that the feeding of a known amount of supplement can be successfully used to estimate dietary proportions and hence intakes of diet components, in mixed diets with up to five ingredients, but this approach requires estimates of faecal alkane recovery.
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Zech, Michael, Sebastian Kreutzer, Roland Zech, Tomasz Goslar, Sascha Meszner, Cameron McIntyre, Christoph Häggi, Timothy Eglinton, Dominik Faust, and Markus Fuchs. "Comparative14C and OSL dating of loess-paleosol sequences to evaluate post-depositional contamination ofn-alkane biomarkers." Quaternary Research 87, no. 1 (January 2017): 180–89. http://dx.doi.org/10.1017/qua.2016.7.
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AbstractThere is an ongoing controversial discussion as to whethern-alkane lipid biomarkers—and organic matter of loess in general—reflect a synsedimentary paleoenvironmental/climate signal or whether they are significantly affected by postdepositional “contamination,” for example related to root and rhizomicrobial activity. In order to address this issue at our study site (the Middle to Late Weichselian loess-paleosol sequence Gleina in Saxony, Germany), we determined and compared radiocarbon ages of bulkn-alkanes and sedimentation ages, as assessed by optically stimulated luminescence (OSL) dating. The bulkn-alkanes of the four dated samples yielded calibrated14C ages ranging from 24.1 to 49.7 cal ka BP (95.4% probability ranges). While the three uppermostn-alkane samples are well within the range or even slightly older than the OSL-inferred sedimentation ages, the lowermostn-alkane sample is slightly younger than the OSL ages. There is hence little or no evidence at our study site forn-alkanes in loess-paleosol sequences being significantly “contaminated” by deep subsoil rooting or microbial processes. We propose a14C isotope mass balance calculation for estimating such contaminations quantitatively. Radiocarbon dating of bulkn-alkanes might have great potential for Quaternary research, and we encourage further comparative14C and OSL studies.
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Zech, M., R. Zech, K. Rozanski, A. Hemp, G. Gleixner, and W. Zech. "Revisiting Mt. Kilimanjaro: Do n-alkane biomarkers in soils reflect the δ<sup>2</sup>H isotopic composition of precipitation?" Biogeosciences Discussions 11, no. 6 (June 3, 2014): 7823–52. http://dx.doi.org/10.5194/bgd-11-7823-2014.
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Abstract. During the last decade compound-specific deuterium (δ2H) analysis of plant leaf wax-derived n-alkanes has become a promising and popular tool in paleoclimate research. This is based on the widely accepted assumption that n-alkanes in soils and sediments generally reflect δ2H of precipitation (δ2Hprec). Recently, several authors suggested that δ2H of n-alkanes (δ2H,sub>n-alkanes) can also be used as proxy in paleoaltimetry studies. Here we present results from a δ2H transect study (~1500 to 4000 m a.s.l.) carried out on precipitation and soil samples taken from the humid southern slopes of Mt. Kilimanjaro. Contrary to earlier suggestions, a distinct altitude effect in δ2Hprec is present above ~2000 m a.s.l., i.e. δ2Hprec values become more negative with increasing altitude. The compound-specific δ2H values of nC27 and nC29 do not confirm this altitudinal trend, but rather become more positive both in the O-layers (organic layers) and the Ah-horizons (mineral topsoils). Although our δ2Hn-alkane results are in agreement with previously published results from the southern slopes of Mt. Kilimanjaro (Peterse et al., 2009, BG, 6, 2799–2807), a major re-interpretation is required given that the δ2Hn-alkane results do not reflect the δ2Hprec results. The theoretical framework for this re-interpretation is based on the evaporative isotopic enrichment of leaf water associated with transpiration process. Modelling results show that relative humidity, decreasing considerably along the southern slopes of Mt. Kilimanjaro (from 78% at ~ 2000 m a.s.l. to 51% at 4000 m a.s.l.), strongly controls δ2Hleaf water. The modelled δ2H leaf water enrichment along the altitudinal transect matches well the measured 2H leaf water enrichment as assessed by using the δ2Hprec and δ2Hn-alkane results and biosynthetic fractionation during n-alkane biosynthesis in leaves. Given that our results clearly demonstrate that n-alkanes in soils do not simply reflect δ2Hprec but rather δ2Hleaf water, we conclude that care has to be taken not to over-interpret δ2Hn-alkane records from soils and sediments when reconstructing δ2H of paleoprecipitation. Both in paleoaltimetry and in paleoclimate studies changes in relative humidity and consequently in δ2Hn-alkane values can completely mask altitudinally or climatically-controlled changes in δ2Hprec.
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Cisneros-Dozal, L. M., X. Xu, C. Bryant, E. J. Pearson, and J. A. J. Dungait. "Grass Material as a Modern Process Standard for 14C Analysis of n-Alkanes." Radiocarbon 58, no. 3 (March 30, 2016): 445–58. http://dx.doi.org/10.1017/rdc.2016.24.
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AbstractOne of the difficulties in reporting accurate radiocarbon results from compound-specific radiocarbon analysis (CSRA) is the lack of suitable process standard materials to correct for the amount and 14C content of carbon added during extensive sample processing. We evaluated the use of n-alkanes extracted from modern grass material (1.224±0.006 fraction modern) as process standards for CSRA. The n-alkanes were isolated using preparative capillary gas chromatography (PCGC) from two independent chemical extraction methods applied to the grass. Since this was our first assessment of the 14C content of the grass n-alkanes, we corrected for extraneous carbon derived from PCGC isolation using commercially available single compounds of modern and 14C-free content. Results were consistent across the two extraction methods showing that the C29n-alkane has a fraction modern value that is within 1σ of the bulk value of the grass while C31n-alkane and less abundant n-alkanes have values within 2σ of the bulk value of the grass. C29 and C31n-alkanes were the most abundant n-alkanes in the grass and, as such, the more feasible for collection of sufficient amounts of carbon for accelerator mass spectrometry (AMS) analysis. Our results suggest that choosing a grass n-alkane with an elution time closest to that of the unknowns may be advisable due to possibly greater effect from GC column bleed (14C-free) at later elution times. We conclude that C29 and C31n-alkanes in modern grass of known 14C content can be used as in-house standards to correct for the addition of 14C-free carbon during sample preparation for 14C analysis of n-alkanes.
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Oliveira, Dimas Estrasulas de, and Luis Orlindo Tedeschi. "Comparing plastic syringes and disposable columns to extract n-alkanes in forage and concentrate feeds." Ciência Rural 40, no. 8 (August 20, 2010): 1844–47. http://dx.doi.org/10.1590/s0103-84782010005000128.
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Saturated aliphatic hydrocarbons (n-alkanes) were extracted from feed, orts, and bovine fecal samples using disposable, plastic 5mL-syringes as an alternative material to disposable columns, which are normally used in the liquid-solid extraction phase of n-alkanes. For both methods, the n-alkane extracts (carbon chain length between 31 and 36 atoms) were identified using gas chromatography. The linear regression between methods were: 1) feces: column Alkane=2.63+0.92×syringeAlkane [r²=0.94, square root of the mean square error (RMSE)=13.7mg kg-1, n=30] from which the intercept and the slope did not simultaneously differ from zero and unity (P>0.05), respectively; 2) feeds: column Alkane=0.36+1.12×syringeAlkane (r²=0.85, RMSE=1.9mg kg-1, n=21) from which the intercept and the slope did not simultaneously differ from zero and unity (P>0.05), respectively; 3) orts: column Alkane=0.49+0.92×syringeAlkane (r²=0.98, RMSE=1.2mg kg-1, n=15) from which the intercept and the slope did not simultaneously differ from zero and unity (P>0.05), respectively. Materials with low concentration of n-alkanes may affect the values obtained in both methods. These results suggested that disposable plastic syringes might be a viable alternative to columns thus, reducing analytical costs.
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McLean, B. M. L., R. W. Mayes, and F. D. DeB Hovell. "The Use of N-alkanes for Estimating Intake and Passage Rate in Horses." Proceedings of the British Society of Animal Science 1996 (March 1996): 98. http://dx.doi.org/10.1017/s0308229600030683.
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Alkanes occur naturally in all plants, although forage crops tend to have higher alkane contents than cereals. N-alkanes have odd-numbered carbon chains. They are ideal for use as markers in feed trials, because, they are inert, indigestible and naturally occurring, and can be recovered in animal faeces. Synthetic alkanes (even-numbered carbon chains) are available commercially and can also used as external markers. Dove and Mayes (1991) cite evidence indicating that faecal recovery of alkanes in ruminants increases with increasing carbon-chain length. Thus the alkane “pairs” (e.g. C35 & C36, and C32 & C33) are used in calculating intake and digestibility because they are long chain and adjacent to each other. However, recent work by Cuddeford and Mayes (unpublished) has found that in horses the faecal recovery rates are similar regardless of chain lengths.
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McLean, B. M. L., R. W. Mayes, and F. D. DeB Hovell. "The Use of N-alkanes for Estimating Intake and Passage Rate in Horses." Proceedings of the British Society of Animal Science 1996 (March 1996): 98. http://dx.doi.org/10.1017/s1752756200592977.
Full textAbstract:
Alkanes occur naturally in all plants, although forage crops tend to have higher alkane contents than cereals. N-alkanes have odd-numbered carbon chains. They are ideal for use as markers in feed trials, because, they are inert, indigestible and naturally occurring, and can be recovered in animal faeces. Synthetic alkanes (even-numbered carbon chains) are available commercially and can also used as external markers. Dove and Mayes (1991) cite evidence indicating that faecal recovery of alkanes in ruminants increases with increasing carbon-chain length. Thus the alkane “pairs” (e.g. C35 & C36, and C32 & C33) are used in calculating intake and digestibility because they are long chain and adjacent to each other. However, recent work by Cuddeford and Mayes (unpublished) has found that in horses the faecal recovery rates are similar regardless of chain lengths.
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Bliedtner, Marcel, Imke K. Schäfer, Roland Zech, and Hans von Suchodoletz. "Leaf wax <i>n</i>-alkanes in modern plants and topsoils from eastern Georgia (Caucasus) – implications for reconstructing regional paleovegetation." Biogeosciences 15, no. 12 (June 29, 2018): 3927–36. http://dx.doi.org/10.5194/bg-15-3927-2018.
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Abstract. Long-chain n-alkanes originate from leaf waxes of higher terrestrial plants, they are relatively resistant against physical and chemical degradation and are preserved in sediment archives for at least millennial timescales. Since their homologue patterns discriminate between vegetation forms, they were increasingly used for paleovegetation reconstructions during the last years. However, before any robust interpretation of the long-chain n-alkane patterns in sediment archives, reference samples from modern vegetation and topsoil material should be investigated at a regional scale. Apart from some temperate and tropical regions, such systematic regional studies on modern plant and topsoil material are still largely lacking.To test the potential of leaf wax-derived n-alkane patterns for paleoenvironmental studies in the semi-humid to semi-arid central southern Caucasus region, we investigated the influence of different vegetation forms on the leaf wax n-alkane signal in modern plants and topsoil material (0–5 cm) from eastern Georgia. We sampled (i) sites with grassland/herbs that included steppe, cultivated grassland and meadows, and (ii) sites that are dominated by deciduous hornbeam forests.The results show that long-chain n-alkanes originate from leaf waxes of higher terrestrial plants and that their homologue pattern allow to discriminate between different vegetation forms: n-Alkanes derived from sites with grassland/herbs are mainly dominated by C31, while n-alkanes derived from sites with deciduous trees/shrubs show high abundances of C29. Thus, long-chain n-alkanes have a great potential when used for regional paleovegetation reconstructions. Moreover, the n-alkane distributions of the topsoils do not show correlations with mean annual temperatures and precipitation along the investigated transect. As degradation of organic matter can affect the leaf wax n-alkane distribution, we further present an updated end-member model that includes our results, accounts for degradation effects and enables semi-quantitative reconstructions of past vegetation changes in the central southern Caucasus region.
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Panayiotou, Constantinos G. "Thermodynamics of alkanol-alkane mixtures." Journal of Physical Chemistry 92, no. 10 (May 1988): 2960–69. http://dx.doi.org/10.1021/j100321a048.
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Mayes, R. V., I. A. Wright, C. S. Lamb, and Alison McBean. "The use of long-chain n-alkanes for estimating intake and digestibility of herbage in cattle." Proceedings of the British Society of Animal Production (1972) 1986 (March 1986): 83. http://dx.doi.org/10.1017/s0308229600015920.
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Studies with sheep suggest that accurate estimates of herbage intake can be obtained by using the herbage alkane tritriacontane (C33) and dosed dotriacontane (C32) as markers, since the faecal recoveries of both alkanes have been shown to be very similar. To validate the technique for herbage intake estimation in grazing cattle there is a need to compare in cattle, the faecal recoveries of both herbage and dosed n-alkanes. It has been observed in sheep that the faecal recoveries of n-alkanes increase as their chain lengths increase, suggesting that the recovery of hexatriacontane (C36), an alkane absent from herbage but available commercially at low cost, should be complete. C36 may therefore have potential as a dosed marker for estimation of faecal output. Thus it may .30 be possible to obtain estimates of both herbage intake and diet digestibility in the same individual grazing animal using n-alkanes as markers. The purpose of the experiment described here was to determine the faecal recoveries in cattle of odd-chain n-alkanes from fresh herbage and of C32 and C36 dosed n-alkanes.
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PIASENTIER, E., S. BOVOLENTA, and F. MALOSSINI. "The n-alkane concentrations in buds and leaves of browsed broadleaf trees." Journal of Agricultural Science 135, no. 3 (November 2000): 311–20. http://dx.doi.org/10.1017/s0021859699008230.
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The concentration of n-alkanes in the cuticular wax of plants can be used to estimate the composition of the diet selected by free-ranging animals. The aims of this study were to characterize the n-alkane profiles of developing leaves and evaluate the degree of chemical discrimination between six browsed broadleaf tree species: European ash (Fraxinus excelsior L.), flowering ash (Fraxinus ornus L.), hornbeam (Carpinus betulus L.), hazel (Corylus avellana L.), mountain ash (Sorbus aucuparia L.) and beech (Fagus sylvatica L). The effect of the stage of development was examined by considering five different vegetative stages: dormant bud (DB), late bud (LB), young leaf (YL), mature leaf (ML) and senescing leaf (SL). Five samples per each vegetative stage and species, gathered in a mixed woodland of the Italian Eastern Alps between February and October, were analysed for their n-alkane concentrations (C23–C36).The residual coefficient of variation was 15·5% on average for the individual n-alkanes considered. There were noticeable differences in individual and total n-alkanes content between species. In particular, C27 was the predominant n-alkane in beech and C33 was found in high proportions in the two species of Fraxinus; hazel and flowering ash had a higher total n-alkanes content than the overall mean, while the lowest values were found in hornbeam and beech. The n-alkane profile also underwent important changes during the vegetative development, with different extent and direction according to the species. In the three successive leaf stages, a tendency for a progressive increase in the longest chain homologues was observed. In any case, the young leaf stage differed most from the contiguous stages.Canonical discriminant analysis indicated that the n-alkane profile of buds and leaves were mathematically distinguishable and the chemical differences between species were persistent over the plant vegetative development.
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Dabirian, Yasaman, Christos Skrekas, Florian David, and Verena Siewers. "Does co-expression of Yarrowia lipolytica genes encoding Yas1p, Yas2p and Yas3p make a potential alkane-responsive biosensor in Saccharomyces cerevisiae?" PLOS ONE 15, no. 12 (December 17, 2020): e0239882. http://dx.doi.org/10.1371/journal.pone.0239882.
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Alkane-based biofuels are desirable to produce at a commercial scale as these have properties similar to current petroleum-derived transportation fuels. Rationally engineering microorganisms to produce a desirable compound, such as alkanes, is, however, challenging. Metabolic engineers are therefore increasingly implementing evolutionary engineering approaches combined with high-throughput screening tools, including metabolite biosensors, to identify productive cells. Engineering Saccharomyces cerevisiae to produce alkanes could be facilitated by using an alkane-responsive biosensor, which can potentially be developed from the native alkane-sensing system in Yarrowia lipolytica, a well-known alkane-assimilating yeast. This putative alkane-sensing system is, at least, based on three different transcription factors (TFs) named Yas1p, Yas2p and Yas3p. Although this system is not fully elucidated in Y. lipolytica, we were interested in evaluating the possibility of translating this system into an alkane-responsive biosensor in S. cerevisiae. We evaluated the alkane-sensing system in S. cerevisiae by developing one sensor based on the native Y. lipolytica ALK1 promoter and one sensor based on the native S. cerevisiae CYC1 promoter. In both systems, we found that the TFs Yas1p, Yas2p and Yas3p do not seem to act in the same way as these have been reported to do in their native host. Additional analysis of the TFs suggests that more knowledge regarding their mechanism is needed before a potential alkane-responsive sensor based on the Y. lipolytica system can be established in S. cerevisiae.
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Cooley, Richard B., Bradley L. Dubbels, Luis A. Sayavedra-Soto, Peter J. Bottomley, and Daniel J. Arp. "Kinetic characterization of the soluble butane monooxygenase from Thauera butanivorans, formerly ‘Pseudomonas butanovora’." Microbiology 155, no. 6 (June 1, 2009): 2086–96. http://dx.doi.org/10.1099/mic.0.028175-0.
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Soluble butane monooxygenase (sBMO), a three-component di-iron monooxygenase complex expressed by the C2–C9 alkane-utilizing bacterium Thauera butanivorans, was kinetically characterized by measuring substrate specificities for C1–C5 alkanes and product inhibition profiles. sBMO has high sequence homology with soluble methane monooxygenase (sMMO) and shares a similar substrate range, including gaseous and liquid alkanes, aromatics, alkenes and halogenated xenobiotics. Results indicated that butane was the preferred substrate (defined by k cat : K m ratios). Relative rates of oxidation for C1–C5 alkanes differed minimally, implying that substrate specificity is heavily influenced by differences in substrate K m values. The low micromolar K m for linear C2–C5 alkanes and the millimolar K m for methane demonstrate that sBMO is two to three orders of magnitude more specific for physiologically relevant substrates of T. butanivorans. Methanol, the product of methane oxidation and also a substrate itself, was found to have similar K m and k cat values to those of methane. This inability to kinetically discriminate between the C1 alkane and C1 alcohol is observed as a steady-state concentration of methanol during the two-step oxidation of methane to formaldehyde by sBMO. Unlike methanol, alcohols with chain length C2–C5 do not compete effectively with their respective alkane substrates. Results from product inhibition experiments suggest that the geometry of the active site is optimized for linear molecules four to five carbons in length and is influenced by the regulatory protein component B (butane monooxygenase regulatory component; BMOB). The data suggest that alkane oxidation by sBMO is highly specialized for the turnover of C3–C5 alkanes and the release of their respective alcohol products. Additionally, sBMO is particularly efficient at preventing methane oxidation during growth on linear alkanes ≥C2, despite its high sequence homology with sMMO. These results represent, to the best of our knowledge, the first kinetic in vitro characterization of the closest known homologue of sMMO.