scholarly journals Structural insights into oxidation of medium-chain fatty acids and flavanone by myxobacterial cytochrome P450 CYP267B1

2018 ◽  
Vol 475 (17) ◽  
pp. 2801-2817 ◽  
Author(s):  
Ilona K. Jóźwik ◽  
Martin Litzenburger ◽  
Yogan Khatri ◽  
Alexander Schifrin ◽  
Marco Girhard ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Cytochrome P450 ◽  
Saturated Fatty Acids ◽  
Decanoic Acid ◽  
Dodecanoic Acid ◽  
Binding Modes ◽  
Cytochrome P450 Enzymes ◽  
Tetradecanoic Acid ◽  
Medium Chain ◽  
Pharmaceutical Industries

Oxidative biocatalytic reactions performed by cytochrome P450 enzymes (P450s) are of high interest for the chemical and pharmaceutical industries. CYP267B1 is a P450 enzyme from myxobacterium Sorangium cellulosum So ce56 displaying a broad substrate scope. In this work, a search for new substrates was performed, combined with product characterization and a structural analysis of substrate-bound complexes using X-ray crystallography and computational docking. The results demonstrate the ability of CYP267B1 to perform in-chain hydroxylations of medium-chain saturated fatty acids (decanoic acid, dodecanoic acid and tetradecanoic acid) and a regioselective hydroxylation of flavanone. The fatty acids are mono-hydroxylated at different in-chain positions, with decanoic acid displaying the highest regioselectivity towards ω-3 hydroxylation. Flavanone is preferably oxidized to 3-hydroxyflavanone. High-resolution crystal structures of CYP267B1 revealed a very spacious active site pocket, similarly to other P450s capable of converting macrocyclic compounds. The pocket becomes more constricted near to the heme and is closed off from solvent by residues of the F and G helices and the B–C loop. The crystal structure of the tetradecanoic acid-bound complex displays the fatty acid bound near to the heme, but in a nonproductive conformation. Molecular docking allowed modeling of the productive binding modes for the four investigated fatty acids and flavanone, as well as of two substrates identified in a previous study (diclofenac and ibuprofen), explaining the observed product profiles. The obtained structures of CYP267B1 thus serve as a valuable prediction tool for substrate hydroxylations by this highly versatile enzyme and will encourage future selectivity changes by rational protein engineering.

scholarly journals Chemical Composition and Antioxidant Activity of the Fruit Essential Oil of Zizyphus lotus (L.) Desf. (Rhamnaceae)

2017 ◽  
Vol 9 (2) ◽  
Author(s):  
Ourzeddine Widad ◽  
Fadel Hamza ◽  
Mechehoud Youcef ◽  
Chalchat Jean-claude ◽  
Figueredo Gilles ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Chemical Composition ◽  
Essential Oil ◽  
Decanoic Acid ◽  
Antioxidant Property ◽  
Dodecanoic Acid ◽  
Tetradecanoic Acid ◽  
Ethyl Hexadecanoate ◽  
Total Oil ◽  
Β Carotene

The essential oil of the fruit of Zizyphus lotus (L.) Desf. belonging to the Rhamnaceae family, was obtained by steam distillation and analyzed by GC-FID and GC-MS. 38 components were identified corresponding to 92% of the total oil. Fatty acids represented the major fraction (78.9%), followed by hydrocarbons (10.8%) while terpenic fraction constituted only 1.1% of the oil (- and β-eudesmol). The fatty acids fraction contained 23 saturated and unsaturated compounds (67.8 and 11%, respectively) from C8 to C18. The major constituents are in decreasing order: ethyl hexadecanoate (12%), decanoic acid (11%), ethyl dodecanoate (9.4%), ethyl hexadec-9-enoate (7.9%), dodecanoic acid (6.5%), ethyl tetradecanoate (6.1%) and tetradecanoic acid (5%). Several studies described the fatty acid composition of different parts of Zizyphus species in the fixed oil. Our study is the first report devoted to the chemical composition of the essential oil of the fruit of this species. The antioxidant property of this oil was evaluated using β-carotene bleaching method.

scholarly journals Effect of storage on fatty acid profile of butter from cows fed whole or ground flaxseed with or without monensin

2010 ◽  
Vol 39 (10) ◽  
pp. 2297-2303 ◽  
Author(s):  
Daniele Cristina da Silva-Kazama ◽  
Geraldo Tadeu dos Santos ◽  
Paula Toshimi Matumoto Pintro ◽  
Jesuí Vergílio Visentainer ◽  
Ricardo Kazama ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Polyunsaturated Fatty Acids ◽  
Fatty Acid Profile ◽  
Saturated Fatty Acids ◽  
Relative Percentage ◽  
Medium Chain ◽  
Medium Chain Fatty Acids ◽  
Ground Flaxseed ◽  
Chain Fatty Acids

Eight Holstein cows with body weight 570 ± 43 kg and 60 ± 20 lactation days were distributed in a double Latin square design with four 21-day periods to determine the effects of feeding ground or whole flaxseed with or without monensin supplementation (0.02% on a dry matter basis) on fatty acid profile of butter stored for 15 and 45 days. Ground flaxseed supply, in comparison to whole flaxseed, reduced relative percentages of 16:0, cis7-16:1, 17:0, and cis10-17:1 but it increased those of cis9,trans11-18:2, cis3-18:3, and omega 3 fatty acids in butter fat, reducing relative percentage of medium-chain fatty acids and increasing the content of polyunsaturated fatty acids. Supplementation with monensin increased relative percentages of cis9,trans11-18:2 and tended to increase relative percentage of 17:0 and decrease that of saturated fatty acids in butter. Butter from cows fed diet with monensin presented lower relative percentages of cis 6-20:4. Relative percentages of cis 9-16:1, cis10-17:1, 18:0, trans11-18:1, cis9-18:1, cis3-18:3, cis6-20:4 in butter stored for 15 days were higher than those stored for 45 days and the relative percentages of cis3-20:5 tended to decrease with the increase of storage period. As a result, relative percentages of saturated fatty acids and medium-chain fatty acids increased with storage time, while those of monounsaturated and long-chain fatty acids decreased. Butter enriched with polyunsaturated fatty acids may have a shorter shelf life due to the negative effect of storage on fatty acid profile which may cause oxidation and rancidity.

Peroxidase activity of bacterial cytochrome P450 enzymes: Modulation by fatty acids and organic solvents

2010 ◽  
Vol 5 (8) ◽  
pp. 891-899 ◽  
Author(s):  
Kersten S. Rabe ◽  
Michael Erkelenz ◽  
Kathrin Kiko ◽  
Christof M. Niemeyer
Keyword(s):  
Fatty Acids ◽  
Cytochrome P450 ◽  
Organic Solvents ◽  
Peroxidase Activity ◽  
Cytochrome P450 Enzymes

scholarly journals Intestinal absorption and liver uptake of medium-chain fatty acids in non-anaesthetized pigs

1993 ◽  
Vol 69 (2) ◽  
pp. 431-442 ◽  
Author(s):  
E. Guillot ◽  
P. Vaugelade ◽  
P. Lemarchali ◽  
A. Re Rat
Keyword(s):  
Fatty Acids ◽  
Portal Vein ◽  
Intestinal Absorption ◽  
Time Course ◽  
Decanoic Acid ◽  
Growing Pigs ◽  
Portal Blood ◽  
Medium Chain ◽  
Medium Chain Fatty Acids ◽  
Chain Fatty Acids

In order to study the rate of intestinal absorption and hepatic uptake of medium-chain fatty acids (MCFA), six growing pigs, mean body weight 65 kg, were fitted with a permanent fistula in the duodenum and with three catheters in the portal vein, carotid artery and hepatic vein respectively. Two electromagnetic flow probes were also set up, one around the portal vein and one around the hepatic artery. A mixture of octanoic and decanoic acids, esterified as medium-chain triacylglycerols, together with maltose dextrine and a nitrogenous fraction was continuously infused for 1 h into the duodenum. Samples of blood were withdrawn from the three vessels at regular intervals for 12 h and further analysed for their non-esterified octanoic and decanoic acid contents. The concentration of non-esterified octanoic and decanoic acids in the portal blood rose sharply after the beginning of each infusion and showed a biphasic time-course with two maximum values, one after 15 min and a later one between 75 and 90 min. Only 65 % of octanoic acid infused into the duodenum and 54 % of decanoic acid were recovered in the portal flow throughout each experiment. The amounts of non-esterified MCFA taken up per h by the liver were close to those absorbed from the gut via the portal vein within the same periods of time, showing that the liver is the main site of utilization of MCFA in pigs. These results have been discussed with a special emphasis laid on the possible mechanisms of the biphasic time-course of MCFA absorption and the incomplete recovery in the portal blood of the infused fatty acids.

scholarly journals The Production of Biofuels from Coconut Oil Using Microwave

2015 ◽  
Vol 9 (7) ◽  
pp. 93 ◽  
Author(s):  
A Suryanto ◽  
Suprapto Suprapto ◽  
Mahfud Mahfud
Keyword(s):  
Fatty Acids ◽  
Reaction Time ◽  
Lauric Acid ◽  
Myristic Acid ◽  
Saturated Fatty Acids ◽  
Electrical Power ◽  
Coconut Oil ◽  
Raw Material ◽  
Medium Chain ◽  
Acid Reaction

Biofuels including biodiesel, an alternative fuel, is renewable, environmentally friendly, non-toxic and lowemission energy. The raw material used in this work was coconut oil, which contained saturated fatty acids about90% with medium chain (C8-C12), especially lauric acid and myristic acid. Reaction was conducted in batchreactor assisted by microwave. The purpose of this research was to study the effect of power and NaOH catalystin transesterification enhanced by microwave and to obtain a biofuels (biodiesel and biokerosene) derived fromcoconut oil. The reaction was performed by mixing oil and methanol with mole ratio of 1:6, catalystconcentration of 1% w/w with setting electrical power at 100, 264, 400, 600 and 800 W. The reaction time wasconditioned at of 2.5, 5, 7.5, 10 and 15 min. The results showed that microwave could accelerate thetransesterification process to produce biodiesel using NaOH catalyst. The highest yield of biodiesel was 97.76 %,or 99.05 % conversion at 5 min reaction, meanwhile biokerosene was 48% after distillation.

scholarly journals Cytochrome P450 Alkane Hydroxylases of the CYP153 Family Are Common in Alkane-Degrading Eubacteria Lacking Integral Membrane Alkane Hydroxylases

2006 ◽  
Vol 72 (1) ◽  
pp. 59-65 ◽  
Author(s):  
Jan B. van Beilen ◽  
Enrico G. Funhoff ◽  
Alexander van Loon ◽  
Andrea Just ◽  
Leo Kaysser ◽  
...  
Keyword(s):  
Cytochrome P450 ◽  
Pseudomonas Putida ◽  
Chain Length ◽  
Nonheme Iron ◽  
Cytochrome P450 Enzymes ◽  
Medium Chain ◽  
Ferredoxin Reductase ◽  
Medium Chain Length ◽  
Reductase Gene ◽  
Alkane Hydroxylases

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.

Conversion of octanoic acid into long-chain saturated fatty acids in premature infants fed a formula containing medium-chain triglycerides

Metabolism ◽  
1994 ◽  
Vol 43 (10) ◽  
pp. 1287-1292 ◽  
Author(s):  
V.P. Carnielli ◽  
E.J. Sulkers ◽  
C. Moretti ◽  
J.L.D. Wattimena ◽  
J.B. van Goudoever ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Premature Infants ◽  
Octanoic Acid ◽  
Saturated Fatty Acids ◽  
Medium Chain Triglycerides ◽  
Medium Chain ◽  
Long Chain

scholarly journals Transformation of Fatty Acids Catalyzed by Cytochrome P450 Monooxygenase Enzymes of Candida tropicalis

2003 ◽  
Vol 69 (10) ◽  
pp. 5992-5999 ◽  
Author(s):  
William H. Eschenfeldt ◽  
Yeyan Zhang ◽  
Hend Samaha ◽  
Lucy Stols ◽  
L. Dudley Eirich ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Cytochrome P450 ◽  
Oleic Acid ◽  
Candida Tropicalis ◽  
Saturated Fatty Acids ◽  
Dicarboxylic Acids ◽  
Initial Step ◽  
Cytochrome P450s ◽  
Commercial Development ◽  
P450 Monooxygenase

ABSTRACT Candida tropicalis ATCC 20336 can grow on fatty acids or alkanes as its sole source of carbon and energy, but strains blocked in β-oxidation convert these substrates to long-chain α,ω-dicarboxylic acids (diacids), compounds of potential commercial value (Picataggio et al., Biotechnology 10:894-898, 1992). The initial step in the formation of these diacids, which is thought to be rate limiting, is ω-hydroxylation by a cytochrome P450 (CYP) monooxygenase. C. tropicalis ATCC 20336 contains a family of CYP genes, and when ATCC 20336 or its derivatives are exposed to oleic acid (C18:1), two cytochrome P450s, CYP52A13 and CYP52A17, are consistently strongly induced (Craft et al., this issue). To determine the relative activity of each of these enzymes and their contribution to diacid formation, both cytochrome P450s were expressed separately in insect cells in conjunction with the C. tropicalis cytochrome P450 reductase (NCP). Microsomes prepared from these cells were analyzed for their ability to oxidize fatty acids. CYP52A13 preferentially oxidized oleic acid and other unsaturated acids to ω-hydroxy acids. CYP52A17 also oxidized oleic acid efficiently but converted shorter, saturated fatty acids such as myristic acid (C14:0) much more effectively. Both enzymes, in particular CYP52A17, also oxidized ω-hydroxy fatty acids, ultimately generating the α,ω-diacid. Consideration of these different specificities and selectivities will help determine which enzymes to amplify in strains blocked for β-oxidation to enhance the production of dicarboxylic acids. The activity spectrum also identified other potential oxidation targets for commercial development.

Effect of Dietary Inclusion of Medium-Chain Saturated Fatty Acids on Ammonia and Methane Emitting Potential of Dairy Manure

2010 ◽  
Author(s):  
Alexander N Hristov ◽  
Chanhee Lee ◽  
Terri Cassidy ◽  
Maria Long ◽  
Kyle Heyler ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Saturated Fatty Acids ◽  
Dairy Manure ◽  
Medium Chain
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