Identification of the oleic acid ethanolamide (OEA) isomer cis-vaccenic acid ethanolamide (VEA) as a highly abundant 18:1 fatty acid ethanolamide in blood plasma from rats and humans

Röhrig, Waldemar; Waibel, Reiner; Perlwitz, Christopher; Pischetsrieder, Monika; Hoch, Tobias

doi:10.1007/s00216-016-9720-8

Cited by 11 publications

(13 citation statements)

References 48 publications

(70 reference statements)

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“…The findings by Röhrig et al [1] suggest that the unknown peak we observed in our study [3] is likely to be VEA. Interestingly, the mean peak area ratio of OEA to VEA in plasma samples from our group of about 3.5 is close to the mean value of 2.4 reported by Röhrig et al for human plasma samples [1]. In plasma of 16 apparently healthy humans, we measured by GC-MS/MS OEA concentrations of 18 ± 6 nM, which suggest an approximate VEA mean concentration of 5 nM.…”

supporting

confidence: 61%

“…We identified the compound eluting at 17.86 min as OEA, yet the peak eluting at 17.92 remained unknown [3]. The findings by Röhrig et al [1] suggest that the unknown peak we observed in our study [3] is likely to be VEA. Interestingly, the mean peak area ratio of OEA to VEA in plasma samples from our group of about 3.5 is close to the mean value of 2.4 reported by Röhrig et al for human plasma samples [1].…”

supporting

confidence: 53%

“…Reply by the authors of [1]: We thank Dr. Dimitrios Tsikas for this highly interesting comment, which provides an important link between our study and Dr. Tsikas' own excellent contributions in this field.…”

mentioning

confidence: 79%

“…Dear Editors, dear authors: I read with great interest the recent research paper by Röhrig et al in Anal Bioanal Chem 2016 [1], which reported on the unequivocal identification of cis-vaccenic acid ethanolamide (VEA) in blood plasma from rats and humans. VEA is an isomer of cis-oleic acid ethanolamide (OEA).…”

mentioning

confidence: 99%

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Letter to the Editor regarding “Identification of the oleic acid ethanolamide (OEA) isomer cis-vaccenic acid ethanolamide (VEA) as a highly abundant 18:1 fatty acid ethanolamide in blood plasma from rats and humans”

Tsikas

2017

Anal Bioanal Chem

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supporting

confidence: 61%

supporting

confidence: 53%

mentioning

confidence: 79%

mentioning

confidence: 99%

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Letter to the Editor regarding “Identification of the oleic acid ethanolamide (OEA) isomer cis-vaccenic acid ethanolamide (VEA) as a highly abundant 18:1 fatty acid ethanolamide in blood plasma from rats and humans”

Tsikas

2017

Anal Bioanal Chem

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“…a‐left), and has been identified as cis ‐vaccenic acid ethanolamide (also called ‘vaccenoylethanolamide’, VEA) as previously reported by Rohrig et al . (). Also, we were able to identify and separate AEA and its isomer (O‐AEA) (Fig.…”

Section: Methodsmentioning

confidence: 97%

Fatty acid amide hydrolase (FAAH) regulates hypercapnia/ischemia‐induced increases in n‐acylethanolamines in mouse brain

Lin

Metherel

Jones

et al. 2017

Journal of Neurochemistry

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N-acylethanolamines (NAEs) are endogenous lipid ligands for several receptors including cannabinoid receptors and peroxisome proliferator-activated receptor-alpha (PPAR-α), which regulate numerous physiological functions. Fatty acid amide hydrolase (FAAH) is largely responsible for the degradation of NAEs. However, at high concentrations of ethanolamines and unesterified fatty acids, FAAH can also catalyze the reverse reaction, producing NAEs. Several brain insults such as ischemia and hypoxia increase brain unesterified fatty acids. Because FAAH can catalyze the synthesis of NAE, we aimed to test whether FAAH was necessary for CO -induced hypercapnia/ischemia increases in NAE. To test this, we examined levels of NAEs, 1- and 2-arachidonoylglycerols as well as their corresponding fatty acid precursors in wild-type and mice lacking FAAH (FAAH-KO) with three Kill methods: (i) head-focused, high-energy microwave irradiation (microwave), (ii) 5 min CO followed by microwave irradiation (CO + microwave), and (iii) 5 min CO only (CO ). Both CO -induced groups increased, to a similar extent, brain levels of unesterified oleic, arachidonic, and docosahexaenoic acid and 1- and 2-arachidonoylglycerols compared to the microwave group in both wild-type and FAAH-KO mice. Oleoylethanolamide (OEA), arachidonoylethanolamide (AEA), and docosahexaenoylethanolamide (DHEA) levels were about 8-, 7-, and 2.5-fold higher, respectively, in the FAAH-KO mice compared with the wild-type mice. Interestingly, the concentrations of OEA, AEA, and DHEA increased 2.5- to 4-fold in response to both CO -induced groups in wild-type mice, but DHEA increased only in the CO group in FAAH-KO mice. Our study demonstrates that FAAH is necessary for CO - induced increases in OEA and AEA but not DHEA. Targeting brain FAAH could impair the production of NAEs in response to brain injuries.

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Endocannabinoid and steroid analysis in infant and adult nails by LC–MS/MS

et al. 2022

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A common method to quantify chronic stress is the analysis of stress markers in keratinized matrices such as hair or nail. In this study, we aimed to validate a sensitive liquid chromatography–tandem mass spectrometry (LC–MS/MS) method for the combined quantification of steroid hormones and endocannabinoids (eCBs) in the keratinized matrix nail. Furthermore, we aimed to investigate the suitability of the nail matrix for the detection of these stress markers in a pilot study. An LC–MS/MS method was used for the simultaneous identification and quantification of four eCBs (2-arachidonoylglycerol (2-AG), anandamide (AEA), oleoylethanolamide (OEA), palmitoylethanolamide (PEA)) and five steroid hormones (cortisol, cortisone, androstenedione, progesterone, testosterone) in human nails using a surrogate analyte method for each analyte. The method was validated in terms of selectivity, response factor, linearity, limit of quantification (LOQ), precision, accuracy, matrix effect, recovery, robustness, and autosampler stability. Nail samples were extracted for 1 h with methanol following a clean-up with a fully automated supported liquid extraction (SLE). The influence of nail weight on the quantification was investigated by using 0.5–20 mg of nail sample. As a proof of concept, nail samples (N = 57) were analyzed from a cohort representing newborns (1 month old), children (between 1 and 10 years), and adults (up to 43 years). It could be shown that the established workflow using a 1 hour extraction and clean-up by SLE was very robust and resulted in a short sample preparation time. The LC–MS/MS method was successfully validated. Matrix effects with ion enhancement occurred mainly for 2-AG. Sample weights below 5 mg showed variations in quantification for some analytes. Certain analytes such as PEA and progesterone could be accurately quantified at a sample weight lower than 5 mg. This is the first study where steroids and eCBs could be simultaneously detected and quantified in infant and adult nails. These results show that nails may serve as an alternative keratinized matrix (compared to hair) for the retrospective monitoring of cumulative eCB and steroid hormone levels. The combined assessment of eCBs and steroids from nails could provide a new approach to gain new insights into stress exposure in newborns and adults. Graphical abstract

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Identification of the oleic acid ethanolamide (OEA) isomer cis-vaccenic acid ethanolamide (VEA) as a highly abundant 18:1 fatty acid ethanolamide in blood plasma from rats and humans

Cited by 11 publications

References 48 publications

Letter to the Editor regarding “Identification of the oleic acid ethanolamide (OEA) isomer cis-vaccenic acid ethanolamide (VEA) as a highly abundant 18:1 fatty acid ethanolamide in blood plasma from rats and humans”

Letter to the Editor regarding “Identification of the oleic acid ethanolamide (OEA) isomer cis-vaccenic acid ethanolamide (VEA) as a highly abundant 18:1 fatty acid ethanolamide in blood plasma from rats and humans”

Fatty acid amide hydrolase (FAAH) regulates hypercapnia/ischemia‐induced increases in n‐acylethanolamines in mouse brain

Endocannabinoid and steroid analysis in infant and adult nails by LC–MS/MS

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