scholarly journals Analysis of Hydroxy Fatty Acids from the Pollen of Brassica campestris L. var. oleifera DC. by UPLC-MS/MS

2013 ◽  
Vol 2013 ◽  
pp. 1-6 ◽  
Author(s):  
Nian-Yun Yang ◽  
Yi-Fang Yang ◽  
Kun Li
Keyword(s):  
Fatty Acids ◽  
Brassica Campestris ◽  
Octadecadienoic Acid ◽  
Molecular Ions ◽  
Hydroxy Fatty Acids ◽  
Hydroxyl Group ◽  
Electrospray Tandem Mass Spectrometry ◽  
Fragment Ions ◽  
First Time ◽  
Alcoholic Hydroxyl

Ultraperformance liquid chromatography coupled with negative electrospray tandem mass spectrometry (UPLC-ESI-MS/MS) was used to determine 7 hydroxy fatty acids in the pollen of Brassica campestris L. var. oleifera DC. All the investigated hydroxy fatty acids showed strong deprotonated molecular ions [M–H]−, which underwent two major fragment pathways of the allyl scission and the β-fission of the alcoholic hydroxyl group. By comparison of their molecular ions and abundant fragment ions with those of reference compounds, they were tentatively assigned as 15,16-dihydroxy-9Z,12Z-octadecadienoic acid (1), 10,11,12-trihydroxy-(7Z,14Z)-heptadecadienoic acid (2), 7,15,16-trihydroxy-9Z,12Z-octadecadienoic acid (3), 15,16-dihydroxy-9Z,12Z-octadecadienoic acid (4), 15-hydroxy-6Z,9Z,12Z-octadecatrienoic acid (5), 15-hydroxy-9Z,12Z- octadecadienoic acid (6), and 15-hydroxy-12Z-octadecaenoic acid (7), respectively. Compounds 3, 5, and 7 are reported for the first time.

scholarly journals Fatty Acyl Esters of Hydroxy Fatty Acid (FAHFA) Lipid Families

Metabolites ◽  
2020 ◽  
Vol 10 (12) ◽  
pp. 512
Author(s):  
Paul L. Wood
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Hydroxy Fatty Acid ◽  
Fatty Acyl ◽  
Hydroxy Fatty Acids ◽  
Wax Esters ◽  
Hydroxyl Group ◽  
Cellular Functions ◽  
Health And Disease ◽  
Branched Chain

Fatty Acyl esters of Hydroxy Fatty Acids (FAHFA) encompass three different lipid families which have incorrectly been classified as wax esters. These families include (i) Branched-chain FAHFAs, involved in the regulation of glucose metabolism and inflammation, with acylation of an internal branched-chain hydroxy-palmitic or -stearic acid; (ii) ω-FAHFAs, which function as biosurfactants in a number of biofluids, are formed via acylation of the ω-hydroxyl group of very-long-chain fatty acids (these lipids have also been designated as o-acyl hydroxy fatty acids; OAHFA); and (iii) Ornithine-FAHFAs are bacterial lipids formed by the acylation of short-chain 3-hydroxy fatty acids and the addition of ornithine to the free carboxy group of the hydroxy fatty acid. The differences in biosynthetic pathways and cellular functions of these lipid families will be reviewed and compared to wax esters, which are formed by the acylation of a fatty alcohol, not a hydroxy fatty acid. In summary, FAHFA lipid families are both unique and complex in their biosynthesis and their biological actions. We have only evaluated the tip of the iceberg and much more exciting research is required to understand these lipids in health and disease.

scholarly journals Incorporation of lipoxygenase products into cholesteryl esters by acyl-CoA:cholesterol acyltransferase in cholesterol-rich macrophages

1988 ◽  
Vol 256 (3) ◽  
pp. 807-814 ◽  
Author(s):  
S N Mathur ◽  
E Albright ◽  
F J Field
Keyword(s):  
Fatty Acids ◽  
Foam Cell ◽  
Fatty Acyl ◽  
Hydroxy Fatty Acids ◽  
Cholesteryl Esters ◽  
Acat Activity ◽  
Lipoxygenase Products ◽  
First Time ◽  
Total Membrane ◽  
Cholesteryl Ester Accumulation

Macrophages which were incubated with acetylated low-density lipoproteins, resulting in cholesteryl ester accumulation, incorporated the monohydroxyeicosatetraenoic acids (5-, 15-, and 12-HETEs) into cholesteryl esters. The esterification of these hydroxy fatty acids to cholesterol by total membrane preparations of cholesterol-rich macrophages was dependent on the synthesis of the fatty acyl-CoA derivative, and was catalysed by acyl-CoA:cholesterol acyltransferase (ACAT). Stimulation of membrane ACAT activity by 25-hydroxycholesterol increased the synthesis of cholesteryl 12-HETE by 40%. In contrast, inhibiting ACAT activity by progesterone and compound 58-035 decreased cholesteryl 12-HETE production by 60% and 90% respectively. Although 5-, 15- and 12-HETE were esterified to cholesterol by ACAT, these monohydroxy fatty acids were less optimal as substrates compared with oleic acid or arachidonic acid. The hydrolysis and release of 12-HETE and the other monohydroxyeicosatetraenoic acids from intracellular cholesteryl esters and phospholipids occurred at a faster rate than for the more conventional fatty acids, oleate and arachidonate. Cholesteryl esters which contain hydroxy fatty acids therefore provide only a transient storage for lipoxygenase products, as these fatty acids are released into the medium as readily as hydroxy fatty acids found in phospholipids and triacylglycerols. The data provide evidence, for the first time, of an ACAT-dependent esterification of the lipoxygenase products 5-, 15- and 12-HETEs to cholesterol in the macrophage-derived foam cell. The channelling of these monohydroxy fatty acids to cholesteryl esters provides a mechanism which can alter the amount of lipoxygenase products incorporated into cellular phospholipids, thus averting deleterious changes to cell membranes. ACAT, by catalysing the esterification of monohydroxyeicosatetraenoic acids to cholesterol, could play a key role in regulating the amount of lipoxygenase products in the pericellular space of the cholesterol-enriched macrophage.

Identification of New Hydroxy Fatty Acids and Ferulic Acid Esters in the Wood of Eucalyptus globulus

Holzforschung ◽  
2002 ◽  
Vol 56 (2) ◽  
pp. 143-149 ◽  
Author(s):  
C. S. R. Freire ◽  
A. J.D. Silvestre ◽  
C. Pascoal Neto
Keyword(s):  
Fatty Acids ◽  
Chemical Composition ◽  
Ferulic Acid ◽  
Eucalyptus Globulus ◽  
Fatty Alcohols ◽  
Hydroxy Fatty Acids ◽  
Gas Chromatography Mass Spectrometry ◽  
Published Data ◽  
First Time ◽  
Acid Esters

Summary The chemical composition of the dichloromethane extract of Eucalyptus globulus wood cultivated in Portugal was studied by gas chromatography-mass spectrometry, prior to and after alkaline hydrolysis. In addition to previously identified lipophilic extractives, 22 free or esterified compounds (14 fatty acids, 2 fatty alcohols and 6 aromatic compounds) were identified for the first time in E. globulus wood. One of these, ferulic acid, was esterified with three different fatty alcohols and with two α-hydroxyfatty acids. Some of the newly identified compounds, particularly the a-hydroxy-fatty acids are responsible for recently reported pitch problems during pulp production in a Portuguese mill. The differences found in the E. globulus chemical composition, when compared with published data, are expected to be related to variations in the location of growth and genetic factors.

scholarly journals Fatty acids and their esters from Cicuta virosa L.

2014 ◽  
Vol 14 ◽  
pp. 71-74
Author(s):  
U Jargalsaikhan ◽  
S Javzan ◽  
D Selenge ◽  
D Nedelcheva ◽  
S Philipov ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Ethyl Ester ◽  
Octadecadienoic Acid ◽  
Acid Ethyl Ester ◽  
Hexadecanoic Acid ◽  
Unsaturated Esters ◽  
Aerial Parts ◽  
First Time

n-Hexane and chloroform fractions of aerial parts and roots of Cicuta virosa L. were investigated by GC-MS. As a result of the study 25 fatty acids and their esters have been identified. Two unsaturated esters such as linoleic acid ethyl ester (IX, 16.66%), and n- hexadecanoic acid ethyl ester (VII, 10.12%), the fatty acid n-hexadecanioc acid (VI, 8.10%) made up the bulk of the aerial parts. Four unsaturated esters such as linoleic acid ethyl ester (IX, 10.15%), dibutylphthalate (XII, 9.55%), n-hexadecanoic acid ethyl ester (VII, 8.19%) and 9, 12, 15 - octadecatrienoic acid ethyl ester (X, 5.9%), two fatty acids as n-hexadecanoic acid (VI, 8,15%) and 9,12-octadecadienoic acid (VIII, 4,5%) predominated in the roots of Cicuta virosa L. These known fatty acids and their esters were found for the first time in this plant species. DOI: http://dx.doi.org/10.5564/mjc.v14i0.203 Mongolian Journal of Chemistry 14 (40), 2013, p71-74

α-Glucosidase Inhibition and Docking Studies of 5-Deoxyflavonols and Dihydroflavonols Isolated from Abutilon pakistanicum

2019 ◽  
Vol 23 (17) ◽  
pp. 1857-1866
Author(s):  
Munawar Hussain ◽  
Zaheer Ahmed ◽  
Shamsun N. Khan ◽  
Syed A. A. Shah ◽  
Rizwana Razi ◽  
...  
Keyword(s):  
Methanolic Extract ◽  
Docking Studies ◽  
Hydroxyl Group ◽  
Coumaric Acid ◽  
In Vitro Activity ◽  
Aerial Parts ◽  
First Time ◽  
Acid Esters ◽  
Phenol Moiety

Three new 5-deoxyflavonoid and dihydroflavonoids 2, 3 and 4 have been isolated from the methanolic extract of Abutioln pakistanicum aerial parts, for which structures were elucidated explicitly by extensive MS- and NMR-experiments. In addition to these, 3,7,4′-trihydroxy-3′-methoxy flavonol (1) is reported for the first time from Abutioln pakistanicum. Compound 2 and 4 are p-coumaric acid esters while compounds 2–4 exhibited α-glucosidase inhibitory activity. Docking studies indicated that the ability of flavonoids 2, 3 and 4 to form multiple hydrogen bonds with catalytically important residues is decisive hence is responsible for the inhibition activity. The docking results signified the observed in-vitro activity quite well which is in accordance with previously obtained conclusion that phenol moiety and hydroxyl group are critical for the inhibition of α-glucosidase enzyme.

Inductive effect in EI-mass spectra of some 5,6-dihalogenides and 5,6-halohydrins of 5α-cholestan-3β-ol and 3β-acetoxy-5α-cholestane

1982 ◽  
Vol 47 (11) ◽  
pp. 2946-2960 ◽  
Author(s):  
Antonín Trka ◽  
Alexander Kasal
Keyword(s):  
Mass Spectra ◽  
Inductive Effect ◽  
Molecular Ions ◽  
Hydroxyl Group ◽  
Halogen Atoms ◽  
Derivatives Of

Partial EI-mass spectra of 3β-hydroxy- and 3β-acetoxy-5α-cholestanes substituted in positions 5α-, 6β- or 5α,6β- with a hydroxyl group or halogen atoms (fluorine, chlorine, bromine) are presented. The molecular ions of 5α,6β-disubstituted derivatives of 3β-hydroxy-5α-cholestane (or of its 3-acetate) are considerably more stable than the corresponding monosubstituted derivatives if at least one of the pair of the vicinal substituents is chlorine or fluorine. This increase in stability, most striking in 5α- and 6β-fluoro compounds, is explained by the inductive effect.

scholarly journals Bufadienolides from the Skin Secretions of the Neotropical Toad Rhinella alata (Anura: Bufonidae): Antiprotozoal Activity against Trypanosoma cruzi

Molecules ◽  
2021 ◽  
Vol 26 (14) ◽  
pp. 4217
Author(s):  
Candelario Rodriguez ◽  
Roberto Ibáñez ◽  
Luis Mojica ◽  
Michelle Ng ◽  
Carmenza Spadafora ◽  
...  
Keyword(s):  
Vero Cells ◽  
Chemical Diversity ◽  
Hydroxyl Group ◽  
Antitrypanosomal Activity ◽  
The Family ◽  
Toad Venom ◽  
Skin Secretions ◽  
Pharmacological Potential ◽  
First Time ◽  
Mcf 7

Toads in the family Bufonidae contain bufadienolides in their venom, which are characterized by their chemical diversity and high pharmacological potential. American trypanosomiasis is a neglected disease that affects an estimated 8 million people in tropical and subtropical countries. In this research, we investigated the chemical composition and antitrypanosomal activity of toad venom from Rhinella alata collected in Panama. Structural determination using mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy led to the identification of 10 bufadienolides. Compounds identified include the following: 16β-hydroxy-desacetyl-bufotalin-3-adipoyl-arginine ester (1), bufotalin (2), 16β-hydroxy-desacetyl-bufotalin-3-pimeloyl-arginine ester (3), bufotalin-3-pimeloyl-arginine ester (4), 16β-hydroxy-desacetyl-bufotalin-3-suberoyl-arginine ester (5), bufotalin-3-suberoyl-arginine ester (6), cinobufagin-3-adipoyl-arginine ester (7), cinobufagin-3-pimeloyl-arginine ester (8), cinobufagin-3-suberoyl-arginine ester (9), and cinobufagin (10). Among these, three new natural products, 1, 3, and 5, are described, and compounds 1–10 are reported for the first time in R. alata. The antitrypanosomal activity assessed in this study revealed that the presence of an arginyl-diacid attached to C-3, and a hydroxyl group at C-14 in the structure of bufadienolides that is important for their biological activity. Bufadienolides showed cytotoxic activity against epithelial kidney Vero cells; however, bufagins (2 and 10) displayed low mammalian cytotoxicity. Compounds 2 and 10 showed activity against the cancer cell lines MCF-7, NCI-H460, and SF-268.

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