Facile Total Synthesis and Antimicrobial Activity of the Marine Fatty Acids (Z)-2-Methoxy-5-hexadecenoic Acid and (Z)-2-Methoxy-6-hexadecenoic Acid

1998 ◽  
Vol 61 (12) ◽  
pp. 1543-1546 ◽  
Author(s):  
Néstor M. Carballeira ◽  
Anastacio Emiliano ◽  
Norali Hernández-Alonso ◽  
Fernando A. González
Keyword(s):  
Fatty Acids ◽  
Antimicrobial Activity ◽  
Total Synthesis ◽  
Hexadecenoic Acid

scholarly journals Occurrence of Cis-11,12-Methylene-Hexadecanoic Acid in the Red Alga Solieria pacifica (Yamada) Yoshida

Molecules ◽  
2021 ◽  
Vol 26 (8) ◽  
pp. 2286
Author(s):  
Gwang-Woo Kim ◽  
Jae-Man Sim ◽  
Yutaka Itabashi ◽  
Min-Jeong Jung ◽  
Joon-Young Jun
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Red Alga ◽  
Proton Nuclear Magnetic Resonance ◽  
Animal Origin ◽  
Monoenoic Acid ◽  
Resonance Spectroscopy ◽  
Hexadecenoic Acid ◽  
Cyclopropane Fatty Acid ◽  
Hexadecanoic Acid

Fatty acids in marine algae have attracted the attention of natural chemists because of their biological activity. The fatty acid compositions of the Solieriaceae families (Rhodophyceae, Gaigartinales) provide interesting information that unusual cyclic fatty acids have been occasionally found. A survey was conducted to profile the characteristic fatty acid composition of the red alga Solieria pacifica (Yamada) Yoshida using gas chromatography-mass spectrometry (GC-MS), infrared spectroscopy (IR), and proton nuclear magnetic resonance spectroscopy (1H-NMR). In S. pacifica, two cyclopentyl fatty acids, 11-cyclopentylundecanoic acid (7.0%), and 13-cyclopentyltridecanoic acid (4.9%), and a cyclopropane fatty acid, cis-11,12-methylene-hexadecanoic acid (7.9%) contributed significantly to the overall fatty acid profile. In particular, this cyclopropane fatty acid has been primarily found in bacteria, rumen microorganisms or foods of animal origin, and has not previously been found in any other algae. In addition, this alga contains a significant amount of the monoenoic acid cis-11-hexadecenoic acid (9.0%). Therefore, cis-11,12-methylene-hexadecanoic acid in S. pacifica was likely produced by methylene addition to cis-11-hexadecenoic acid.

scholarly journals Antioxidant, Antimicrobial Activities and Fatty Acid Components of Flower, Leaf, Stem and Seed of Hypericum scabrum

2011 ◽  
Vol 6 (11) ◽  
pp. 1934578X1100601 ◽  
Author(s):  
Ali Shafaghat
Keyword(s):  
Fatty Acids ◽  
Gas Chromatography ◽  
Antimicrobial Activity ◽  
Antioxidant Activity ◽  
Radical Scavenging ◽  
Omega 3 Fatty Acids ◽  
Omega 3 ◽  
Hexane Extracts ◽  
Hypericum Scabrum ◽  
Different Parts

The hexane extracts of flower, leaf, stem, and seed of Hypericum scabrum, which were collected from northwestern Iran, were obtained by extraction in a Soxhlet apparatus. The fatty acids were converted to methyl esters and determined by gas chromatography/flame ionization detector (GC/FID) and gas chromatography/mass spectrometry (GC/MS) systems. The hexane extract from the flower, leaf, stem, and seed contained 39.1%, 43.2%, 29.0%, and 37.6% of omega-3 fatty acids, respectively. The other main components of the flower extract were tetracosane (12.2%) and palmitic acid (9.3%), and that of the leaf extract was palmitic acid (7.4%). The stem and seed extracts contained bis(2-ethylhexyl)phthalate (18.7% and 35.7%), nonacosane (11.7% and 3.9%) and linoleic acid (6.5% and 6.9%) as major components. The hexane extracts of different parts from H. scabrum represent an important source of omega-3 fatty acids in several Hypericum species. The antioxidant activity of all hexane extracts was evaluated by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging method. The results indicate that hexane extracts from different parts of H. scabrum possess considerable antioxidant activity. The highest radical scavenging activity was detected in seed, which had an IC50 = 165 μg/mL. The antimicrobial activity of the extracts of those samples were determined against seven Gram-positive and Gram-negative bacteria ( Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, S. epidermidis, Escherichia coli, Pseudomonas aeruginosa, and Klebsiella pneumoniae), as well as three fungi ( Candida albicans, Saccharomyces cerevisiae, and Aspergillus niger). The bioassay showed that the oil exhibited moderate antimicrobial activity. This study reveals that the all parts of this plant are attractive sources of fatty acid components, especially the essential ones, as well as of effective natural antioxidants.

scholarly journals First total synthesis of the (±)-2-methoxy-6-heptadecynoic acid and related 2-methoxylated analogs as effective inhibitors of the Leishmania topoisomerase IB enzyme

2012 ◽  
Vol 84 (9) ◽  
pp. 1867-1875 ◽  
Author(s):  
Néstor M. Carballeira ◽  
Michelle Cartagena ◽  
Fengyu Li ◽  
Zhongfang Chen ◽  
Christopher F. Prada ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Total Synthesis ◽  
Leishmania Donovani ◽  
Dna Topoisomerase ◽  
Triple Bonds ◽  
Weak Intermolecular Interactions ◽  
Topoisomerase Ib ◽  
Effective Inhibition ◽  
Acetylenic Fatty Acid

The fatty acids (±)-2-methoxy-6Z-heptadecenoic acid, (±)-2-methoxy-6-hepta-decynoic acid, and (±)-2-methoxyheptadecanoic acid were synthesized and their inhibitory activity against the Leishmania DNA topoisomerase IB enzyme (LdTopIB) determined. Both 2-OMe-17:1 fatty acids were synthesized from 4-bromo-1-pentanol, the olefinic fatty acid in 10 steps and in 7 % overall yield, while the acetylenic fatty acid in 7 steps and in 14 % overall yield. The 2-OMe-17:0 acid was prepared in 6 steps and in 42 % yield from 1-hexa-decanol. The 2-OMe-17:1 acids inhibited LdTopIB, with the acetylenic acid displaying an EC50 = 16.6 ± 1.1 μM, but the 2-OMe-17:0 acid did not inhibit LdTopIB. The (±)-2-methoxy-6Z-heptadecenoic acid preferentially inhibited LdTopIB over the human TopIB enzyme. Unsaturation seems to be a prerequisite for effective inhibition, rationalized in terms of weak intermolecular interactions between the active site of LdTopIB and either the double or triple bonds of the fatty acids. Toxicity toward Leishmania donovani promastigotes was also investigated, resulting in the order acetylenic > olefinic > saturated with the (±)-2-methoxy-6-heptadecynoic acid displaying an EC50 = 74.0 ± 17.1 μM. Our results indicate that α-methoxylation decreases the toxicity of C17:1 fatty acids toward L. donovani promastigotes, but improves their selectivity index.

Characterization of Aeromonas genomic species by using quinone, polyamine, and fatty acid patterns

1994 ◽  
Vol 40 (10) ◽  
pp. 844-850 ◽  
Author(s):  
Peter Kämpfer ◽  
Klaus Blasczyk ◽  
Georg Auling
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Octadecenoic Acid ◽  
Hexadecenoic Acid ◽  
Genomic Species ◽  
Great Homogeneity ◽  
Hydroxylated Fatty Acids ◽  
Fatty Acid Patterns ◽  
Chemotaxonomic Study

A chemotaxonomic study was carried out on representative strains of 13 Aeromonas genomic species. Quinone, polyamine, and fatty acid patterns were found to be very useful for an improved characterization of the genus and an improved differentiation from members of the families Enterobacteriaceae and Vibrionaceae. The Q-8-benzoquinone was the predominant ubiquinone, and putrescine and diaminopropane were the major poly amines of the genus. The fatty acid patterns of 181 strains, all characterized by DNA–DNA hybridization, showed a great homogeneity within the genus, with major amounts of hexadecanoic acid (16:0), hexadecenoic acid (16:1), and octadecenoic acid (18:1), and minor amounts of the hydroxylated fatty acids (3-OH 13:0, 2-OH 14:0, 3-OH 14:0) in addition to some iso and anteiso branched fatty acids (i-13:0, i-17:1, i-17:0, and a-17:0). Although some differences in fatty acid profiles between the genomic species could be observed, a clearcut differentiation of all species was not possible.Key words: Aeromonas, polyamines, quinones, fatty acids, differentiation.

Depot fatty acids of Aberdeen Angus and Friesian cattle reared on hay and barley diets

1977 ◽  
Vol 89 (3) ◽  
pp. 575-582 ◽  
Author(s):  
W. M. F. Leat
Keyword(s):  
Fatty Acids ◽  
Fatty Acid Composition ◽  
Fatty Acid ◽  
Stearic Acid ◽  
Acid Composition ◽  
Visual Inspection ◽  
Subcutaneous Fat ◽  
Octadecenoic Acid ◽  
Hexadecenoic Acid ◽  
Friesian Cattle

SummaryAberdeen Angus and Friesian cattle were reared from 4 months of age to slaughter weight at 18–24 months on either high-barley or high-hay diets. Samples of subcutaneous fat were taken by biopsy at 3 monthly intervals, and the degree of fatness of each animal was estimated ultrasonically prior to slaughter, and by visual inspection of the carcasses.The barley-fed animals gained weight more rapidly, and fattened more quickly than the hay-fed animals with the Angus being fatter than the Friesian at the same age. The percentage stearic acid (C18:0) in subcutaneous fat decreased with age and was replaced by octadecenoic acid (C18:l) and hexadecenoic acid (C16:l), these changes being more rapid in barley-fed than in hay-fed animals. At the same degree of fatness the depot fats of the Friesians were more unsaturated than those of the Angus, and in both breeds the fatter the animal the more unsaturated was its depot fat.In the hay-fed cattle the percentage C16:0 in subcutaneous fat increased during the last half of the experiment and at slaughter the percentage C16:0 was significantly higher, and C18:l significantly lower, in all depot fats compared with those of the barley-fed animals.It is concluded that the fatty acid composition of bovine depot fats is modulated by the degree of fattening, and can be affected by diet.

scholarly journals Channeling of Eukaryotic Diacylglycerol into the Biosynthesis of Plastidial Phosphatidylglycerol

2006 ◽  
Vol 282 (7) ◽  
pp. 4613-4625 ◽  
Author(s):  
Markus Fritz ◽  
Heiko Lokstein ◽  
Dieter Hackenberg ◽  
Ruth Welti ◽  
Mary Roth ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Double Bond ◽  
Transgenic Plants ◽  
Phosphatidic Acid ◽  
Lipid Analysis ◽  
Photosynthetic Apparatus ◽  
Hexadecenoic Acid ◽  
Transgenic Tobacco Plants ◽  
Tobacco Plants

Plastidial glycolipids contain diacylglycerol (DAG) moieties, which are either synthesized in the plastids (prokaryotic lipids) or originate in the extraplastidial compartment (eukaryotic lipids) necessitating their transfer into plastids. In contrast, the only phospholipid in plastids, phosphatidylglycerol (PG), contains exclusively prokaryotic DAG backbones. PG contributes in several ways to the functions of chloroplasts, but it is not known to what extent its prokaryotic nature is required to fulfill these tasks. As a first step toward answering this question, we produced transgenic tobacco plants that contain eukaryotic PG in thylakoids. This was achieved by targeting a bacterial DAG kinase into chloroplasts in which the heterologous enzyme was also incorporated into the envelope fraction. From lipid analysis we conclude that the DAG kinase phosphorylated eukaryotic DAG forming phosphatidic acid, which was converted into PG. This resulted in PG with 2–3 times more eukaryotic than prokaryotic DAG backbones. In the newly formed PG the unique Δ3-trans-double bond, normally confined to 3-trans-hexadecenoic acid, was also found in sn-2-bound cis-unsaturated C18 fatty acids. In addition, a lipidomics technique allowed the characterization of phosphatidic acid, which is assumed to be derived from eukaryotic DAG precursors in the chloroplasts of the transgenic plants. The differences in lipid composition had only minor effects on measured functions of the photosynthetic apparatus, whereas the most obvious phenotype was a significant reduction in growth.

Total Synthesis of Cardiolipins Containing Chiral Cyclopropane Fatty Acids

2017 ◽  
Vol 82 (15) ◽  
pp. 7832-7838 ◽  
Author(s):  
Shinsuke Inuki ◽  
Ippei Ohta ◽  
Shunichi Ishibashi ◽  
Masayuki Takamatsu ◽  
Koichi Fukase ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Total Synthesis ◽  
Cyclopropane Fatty Acids
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