Differentiation of monoepoxide isomers of polyunsaturated fatty acids and fatty acid esters by low-energy charge exchange mass spectrometry

Background: Fatty acid esters of hydroxy fatty acids (FAHFAs) are a group of fatty acids with potential anti-inflammatory and anti-diabetic effects. The blood levels of FAHFAs and their regulation in humans have hardly been studied.Objective: We aimed to investigate serum FAHFA levels in well-characterized human cohorts, to evaluate associations with age, sex, BMI, weight loss, diabetic status, and diet.Methods: We analyzed levels of stearic-acid-9-hydroxy-stearic-acid (9-SAHSA), oleic-acid-9-hydroxy-stearic-acid (9-OAHSA) and palmitic-acid-9-hydroxy-palmitic-acid (9-PAHPA) as well as different palmitic acid-hydroxy-stearic-acids (PAHSAs) by HPLC-MS/MS with the use of an internal standard in various cohorts: A cohort of different age groups (18–25y; 40–65y; 75–85y; Σn = 60); severely obese patients undergoing bariatric surgery and non-obese controls (Σn = 36); obese patients with and without diabetes (Σn = 20); vegetarians/vegans (n = 10) and omnivores (n = 9); and young men before and after acute overfeeding with saturated fatty acids (SFA) (n = 15).Results: Omnivores had substantially higher FAHFA levels than vegetarians/vegans [median (25th percentile; 75th percentile) tFAHFAs = 12.82 (7.57; 14.86) vs. 5.86 (5.10; 6.71) nmol/L; P < 0.05]. Dietary overfeeding by supplementation of SFAs caused a significant increase within 1 week [median tFAHFAs = 4.31 (3.31; 5.27) vs. 6.96 (6.50; 7.76) nmol/L; P < 0.001]. Moreover, obese patients had lower FAHFA levels than non-obese controls [median tFAHFAs = 3.24 (2.80; 4.30) vs. 5.22 (4.18; 7.46) nmol/L; P < 0.01] and surgery-induced weight loss increased 9-OAHSA level while other FAHFAs were not affected. Furthermore, significant differences in some FAHFA levels were found between adolescents and adults or elderly, while no differences between sexes and between diabetic and non-diabetic individuals were detected.Conclusions: FAHFA serum levels are strongly affected by high SFA intake and reduced in severe obesity. Age also may influence FAHFA levels, whereas there was no detectable relation with sex and diabetic status. The physiological role of FAHFAs in humans remains to be better elucidated.Trial Registration: All studies referring to these analyses were registered in the German Clinical Trial Register (https://www.drks.de/drks_web/) with the numbers DRKS00009008, DRKS00010133, DRKS00006211, and DRKS00009797.

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Investigation of Z- and E-Unsaturated Fatty Acids, Fatty Acid Esters, and Fatty Alcohols at the Air/Water Interface by Infrared Spectroscopy

Langmuir ◽

10.1021/la00001a039 ◽

1995 ◽

Vol 11 (1) ◽

pp. 225-230 ◽

Cited By ~ 25

Author(s):

Arne Gericke ◽

Heinrich Huehnerfuss

Keyword(s):

Fatty Acids ◽

Infrared Spectroscopy ◽

Fatty Acid ◽

Unsaturated Fatty Acids ◽

Fatty Alcohols ◽

Fatty Acid Esters ◽

Water Interface ◽

Air Water Interface ◽

Acid Esters

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Synthesis of (-)-menthol fatty acid esters in and from (-)-menthol and fatty acids – novel concept for lipase catalyzed esterification based on eutectic solvents

Molecular Catalysis ◽

10.1016/j.mcat.2018.08.003 ◽

2018 ◽

Vol 458 ◽

pp. 67-72 ◽

Cited By ~ 23

Author(s):

Magdalena Hümmer ◽

Selin Kara ◽

Andreas Liese ◽

Ina Huth ◽

Jens Schrader ◽

...

Keyword(s):

Fatty Acids ◽

Fatty Acid ◽

Fatty Acid Esters ◽

Novel Concept ◽

Acid Esters

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SELECTIVITY OF CANDIDA RUGOSA LIPASE IMMOBILIZED ONTO LAYERED DOUBLE HYDROXIDES AS CATALYST IN SYNTHESIS OF FATTY ACID ESTERS

Jurnal Teknologi ◽

10.11113/jt.v78.8647 ◽

2016 ◽

Vol 78 (5-6) ◽

Author(s):

Mohd Basyaruddin Abdul Rahman ◽

Siti Salhah Othman ◽

Noor Mona Md Yunus

Keyword(s):

Fatty Acids ◽

Fatty Acid ◽

Chain Length ◽

Candida Rugosa ◽

Candida Rugosa Lipase ◽

Carbon Chain ◽

Fatty Acid Esters ◽

Carbon Chain Length ◽

Chain Lengths ◽

Acid Esters

The enzymatic selectivity of Lipase from Candida rugosa immobilized onto a calcined layered double hydroxide (CLDHs-CRL) towards the chain-length of fatty acids and alcohols in the synthesis of fatty acid esters was investigated. The results showed that CMAN-CRL catalyzed the esterification process with fatty acids of medium chain lengths (C10-C14) effectively while, CNAN-CRL and CZAN-CRL exhibited high percentage conversion in fatty acids with carbon chain lengths of C8-C12 and C10-C18, respectively. In the alcohol selectivity study, CMAN-CRL showed high selectivity toward alcohols with carbon chain lengths of C4, C6 and C10. On the other hand, both CNAN-CRL and CZAN-CRL exhibited rather low selectivity towards longer carbon chain length of alcohols.

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Impact of Selected Cosmetic Ingredients on Common Microorganisms of Healthy Human Skin

Cosmetics ◽

10.3390/cosmetics6030045 ◽

2019 ◽

Vol 6 (3) ◽

pp. 45 ◽

Cited By ~ 1

Author(s):

Dorota Dobler ◽

Thomas Schmidts ◽

Sören Wildenhain ◽

Ilona Seewald ◽

Michael Merzhäuser ◽

...

Keyword(s):

Fatty Acids ◽

Fatty Acid ◽

Human Skin ◽

Chain Length ◽

Skin Diseases ◽

Free Acid ◽

Fatty Alcohols ◽

Fatty Acid Esters ◽

Bacterial Strains ◽

Acid Esters

Human skin is a complex ecosystem and is host to a large number of microorganisms. When the bacterial ecosystem is balanced and differentiated, skin remains healthy. However, the use of cosmetics can change this balance and promote the appearance of skin diseases. The skin’s microorganisms can utilize some cosmetic components, which either promote their growth, or produce metabolites that influence the skin environment. In this study, we tested the ability of the Malassezia species and some bacterial strains to assimilate substances frequently used in dermal formulations. The growth capability of microorganisms was determined and their lipase activity was analyzed. The growth of all Malassezia spp. in the presence of free acids, free acid esters, and fatty alcohols with a fatty chain length above 12 carbon atoms was observed. No growth was observed in the presence of fatty alcohol ethers, secondary fatty alcohols, paraffin- and silicon-based substances, polymers, polyethylene glycols, quaternary ammonium salts, hydroxy fatty acid esters, or fatty acids and fatty acid esters with a fatty chain length shorter than 12 carbon atoms. The hydrolysis of esters by Malassezia lipases was detected using High Performance Thin Layer Chromatography (HPTLC). The production of free fatty acids as well as fatty alcohols was observed. The growth promotion or inhibition of bacterial strains was only found in the presence of a few ingredients. Based on these results, formulations containing microbiome inert ingredients were developed.

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