InChI=1S/C16H32O2/c1-15(2)13-11-9-7-5-3-4-6-8-10-12-14-16(17)18/h15H,3-14H2,1-2H3,(H,17,18) |
ZONJATNKKGGVSU-UHFFFAOYSA-N |
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Cervus nippon
(NCBI:txid9863)
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Found in the preorbital gland secretion.
See:
PubMed
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Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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mammalian metabolite
Any animal metabolite produced during a metabolic reaction in mammals.
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biomarker
A substance used as an indicator of a biological state.
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View more via ChEBI Ontology
14-methylpentadecanoic acid
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14-methyl pentadecylic acid
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LIPID MAPS
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Iso-C16:0
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HMDB
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isohexadecanoic acid
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LIPID MAPS
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isopalmitic acid
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LIPID MAPS
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1776629
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Reaxys Registry Number
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Reaxys
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4669-02-7
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CAS Registry Number
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NIST Chemistry WebBook
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4669-02-7
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CAS Registry Number
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ChemIDplus
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Xin H, Khan NA, Liu X, Jiang X, Sun F, Zhang S, Sun Y, Zhang Y, Li X (2021) Profiles of Odd- and Branched-Chain Fatty Acids and Their Correlations With Rumen Fermentation Parameters, Microbial Protein Synthesis, and Bacterial Populations Based on Pure Carbohydrate Incubation in vitro. Frontiers in nutrition 8, 733352 [PubMed:34631768] [show Abstract] The objectives of this study were to evaluate changes in profiles of odd- and branched-chain fatty acids (OBCFA), including pentadecanoic acid (C15:0), 13-methyltetradecanoic acid (iso-C15:0), 12-methyltetradecanoic acid (anteiso-C15:0), 14-methylpentadecanoic acid (iso-C16:0), heptadecanoic acid (C17:0), 15-methylhexadecanoic acid (iso-C17:0), and 14-methylhexadecanoic acid (anteiso-C17:0) during in vitro fermentation of pure carbohydrates mixtures in the buffer-rumen fluid. The second objective was to correlate the changes in the OBCFA profile to the corresponding changes in ruminal fermentation parameters, microbial crude protein (MCP) synthesis, and bacterial populations. Five pure carbohydrates mixtures containing different cellulose: starch (C:S) ratios, i.e., 0:100, 25:75, 50:50, 75:25, and 100:0, were incubated for 6, 12, 18, and 24 h in vitro. The results showed that there was significant interaction (P < 0.05) between C:S and incubation time for changes in all OBCFA profiles, except iso-C17:0. The highest concentration of total OBCFA (3.94 mg/g dry matter; DM) was observed in the residues after 24 h of fermentation when the C:S was 0:100, while the lowest concentration of OBCFA (1.65 mg/g DM) was produced after 6 h of incubation when the C:S was 50:50. The correlation analysis revealed that the concentration of iso-C16:0 might be a potential marker for the estimation of total volatile fatty acids (ρ = 0.78) and MCP synthesis (ρ = 0.82) in the rumen. Compared to starch degrading bacteria, cellulolytic bacteria had stronger correlations with OBCFA concentrations, and the strongest correlation was found between the population of Ruminococcus flavefaciens with C15:0 concentration (ρ = 0.70). Notably, this is the first paper reporting relationship between OBCFA with rumen fermentation products and microbial protein synthesis based on fermentation of pure carbohydrates mixtures in vitro, and thus avoid confounding interference from dietary protein and fat presence in the in vivo studies. However, more in-depth experiments are needed to substantiate the current findings. | Kristoffersen V, Jenssen M, Jawad HR, Isaksson J, Hansen EH, Rämä T, Hansen KØ, Andersen JH (2021) Two Novel Lyso-Ornithine Lipids Isolated from an Arctic Marine Lacinutrix sp. Bacterium. Molecules (Basel, Switzerland) 26, 5295 [PubMed:34500726] [show Abstract] The Lacinutrix genus was discovered in 2005 and includes 12 Gram-negative bacterial species. To the best of our knowledge, the secondary metabolite production potential of this genus has not been explored before, and examination of Lacinutrix species may reveal novel chemistry. As part of a screening project of Arctic marine bacteria, the Lacinutrix sp. strain M09B143 was cultivated, extracted, fractionated and tested for antibacterial and cytotoxic activities. One fraction had antibacterial activity and was subjected to mass spectrometry analysis, which revealed two compounds with elemental composition that did not match any known compounds in databases. This resulted in the identification and isolation of two novel isobranched lyso-ornithine lipids, whose structures were elucidated by mass spectrometry and NMR spectroscopy. Lyso-ornithine lipids consist of a 3-hydroxy fatty acid linked to the alpha amino group of an ornithine amino acid through an amide bond. The fatty acid chains were determined to be iso-C15:0 (1) and iso-C16:0 (2). Compound 1 was active against the Gram-positive S. agalactiae, while 2 showed cytotoxic activity against A2058 human melanoma cells. | Schwitalla JW, Benndorf R, Martin K, Vollmers J, Kaster AK, de Beer ZW, Poulsen M, Beemelmanns C (2020) Streptomyces smaragdinus sp. nov., isolated from the gut of the fungus growing-termite Macrotermes natalensis. International journal of systematic and evolutionary microbiology 70, 5806-5811 [PubMed:32969785] [show Abstract] The taxonomic position of a novel aerobic, Gram-positive actinobacteria, designated strain RB5T, was determined using a polyphasic approach. The strain, isolated from the gut of the fungus-farming termite Macrotermes natalensis, showed morphological, physiological and chemotaxonomic properties typical of the genus Streptomyces. Based on 16S rRNA gene sequence analysis, the closest phylogenetic neighbour of RB5T was Streptomyces polyrhachis DSM 42102T (98.87 %). DNA-DNA hybridization experiments between strain RB5T and S. polyrhachis DSM 42102T resulted in a value of 27.4 % (26.8 %). The cell wall of strain RB5T contained ll-diaminopimelic acid as the diagnostic amino acid. Mycolic acids and diagnostic sugars in whole-cell hydrolysates were not detected. The strain produced the following major phospholipids: diphosphatidylglycerol, phosphatidylethanolamine, phosphatidylinositol, phosphatidylinositol-mannoside and phosphatidylserine. The menaquinone profile showed hexa- and octahydrogenated menaquinones containing nine isoprene units [MK-9(H6) and MK-9(H8)]. The strain exhibited a fatty acid profile containing the following major fatty acids: 12-methyltridecanoic acid (iso-C14 : 0) 12-methyltetradecanoic acid (anteiso-C15 : 0), 13-methyltetradecanoic acid (iso-C15 : 0) and 14-methylpentadecanoic acid (iso-C16 : 0). Here, we propose a novel species of the genus Streptomyces - Streptomyces smaragdinus with the type strain RB5T (=VKM Ac-2839T=NRRL B65539T). | Kim S, Hwang J, Xuan J, Jung YH, Cha HS, Kim KH (2014) Global metabolite profiling of synovial fluid for the specific diagnosis of rheumatoid arthritis from other inflammatory arthritis. PloS one 9, e97501 [PubMed:24887281] [show Abstract] Currently, reliable biomarkers that can be used to distinguish rheumatoid arthritis (RA) from other inflammatory diseases are unavailable. To find possible distinctive metabolic patterns and biomarker candidates for RA, we performed global metabolite profiling of synovial fluid samples. Synovial fluid samples from 38 patients with RA, ankylosing spondylitis, Behçet's disease, and gout were analyzed by gas chromatography/time-of-flight mass spectrometry (GC/TOF MS). Orthogonal partial least-squares discriminant and hierarchical clustering analyses were performed for the discrimination of RA and non-RA groups. Variable importance for projection values were determined, and the Wilcoxon-Mann-Whitney test and the breakdown and one-way analysis of variance were conducted to identify potential biomarkers for RA. A total of 105 metabolites were identified from synovial fluid samples. The score plot of orthogonal partial least squares discriminant analysis showed significant discrimination between the RA and non-RA groups. The 20 metabolites, including citrulline, succinate, glutamine, octadecanol, isopalmitic acid, and glycerol, were identified as potential biomarkers for RA. These metabolites were found to be associated with the urea and TCA cycles as well as fatty acid and amino acid metabolism. The metabolomic analysis results demonstrated that global metabolite profiling by GC/TOF MS might be a useful tool for the effective diagnosis and further understanding of RA. | Wood WF (2004) Straight and branched-chain fatty acids in preorbital glands of sika deer, Cervus nippon. Journal of chemical ecology 30, 479-482 [PubMed:15112737] [show Abstract] Using GC-MS analysis, 11 major volatile compounds were found in the preorbital gland secretion from a female sika deer, Cervus nippon. These compounds are the C14 through C18 straight-chain fatty acids, (ZZ)-9,12-octadecadienoic acid, 12-methyltridecanoic acid, 13-methyltetradecanoic acid, 14-methylpentadecanoic acid, 14-methylhexadecanoic acid, and 15-methylhexadecanoic acid. The five branched-chain acids make up over 29% of the volatiles in the gland. This is the first time branched-chain carboxylic acids have been reported from ungulate preorbital glands. | Mimura T, Tsujibo H, Nakamura R, Aonuma S, Oda Y, Momose M (1981) Effects of branched chain fatty acids of iso-C12:0 to iso-C16:0 on gastric secretion and experimental ulceration in rats. Journal of pharmacobio-dynamics 4, 844-850 [PubMed:6120223] [show Abstract] We examined the inhibitory activities of branched-chain fatty acids of iso-C12:0 to iso-C16:0 on gastric secretion in rats. Consequently, iso-C13:0 and iso-C15:0 were found to have strong inhibitory activities on gastric secretion in rats. In the case of intraduodenal administration, iso-C15:0 also showed a significant inhibition of gastric juice secretion. Therefore, the effects of iso-C13:0 and iso-C15:0 on ulceration in pylorus-ligated rats and aspirin-induced ulcer were examined. At the doses of 10 and 25 mg/kg, iso-C13:0 and iso-C15:0 significantly decreased the ulcer index in pylorus-ligated rats, and aspirin-induced ulcer was also significantly inhibited at the doses of 25 and 50 mg/kg. Finally, effect of iso-C15:0 on pepsin, Mg++-ATPase and carbonic anhydrase, which are considered to play an important role in the mechanism of gastric juice secretion, was examined in vitro, centering around iso-C15:0 which showed a marked effect in gastric juice secretion inhibitory and anti-ulcerogenic activities. Iso-C15:0 showed inhibitory activity on pepsin and Mg++-ATPase, but entirely no activity on inhibiting carbonic anhydrase. | HANSEN RP, SHORLAND FB, COOKE NJ (1955) The branched-chain fatty acids of ox fat. 3. The isolation of 14-methylpentadecanoic acid (isopalmitic acid) from ox perinephric fat. The Biochemical journal 61, 547-549 [PubMed:13276333] |
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