N-docosahexaenoylethanolamine detected in human breast milk

Smith, Stephanie L.; Kevala, Karl; Cunningham, Bridget; Rouse, Christopher; Hunt, Carl E.; Kim, Hee‐Yong

doi:10.1016/j.plefa.2018.07.016

Cited by 7 publications

(10 citation statements)

References 16 publications

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“…However, a supplementation influence was not observed, likely due to participants’ consumption of high-DHA food sources in the control group. Despite this, Smith et al (2018) were able to observe that DHA in human milk correlated with the concentration of DHEA ( r = 0.62, p < .001). The correlation between human milk concentrations of DHA and its ethanolamine-derived EC, DHEA, is in line with a previous report by our group where it was also observed that DHA was correlated with DHEA ( r = 0.69, p < .001) and also with its glycerol-derived EC, DHG ( r = 0.95, p ≤ .01; Gaitán et al, 2018).…”

Section: Discussionmentioning

confidence: 77%

Maternal Dietary Fatty Acids and Their Relationship to Derived Endocannabinoids in Human Milk

et al. 2021

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Background Dietary long-chain polyunsaturated fatty acids are known to benefit infant development. After birth, human milk provides arachidonic, eicosapentaenoic, and docosahexaenoic acids to the infant. Endocannabinoids are endogenous lipid mediators derived from the long-chain polyunsaturated fatty acids. Although the roles and the mechanisms of action are not fully understood, previous researchers have suggested that endocannabinoids might play a role in infant feeding behavior. Research Aims To assess (i) maternal dietary intake of long-chain polyunsaturated fatty acids and (ii) their relationship to concentrations of fatty acids and derived endocannabinoids in human milk. Methods For this exploratory-longitudinal study, participants ( N = 24) provided dietary intake data and milk samples. Fatty acids and derived endocannabinoids: Arachidonylethanolamide, arachidonoylglycerol, docosahexaenoyl glycerol, eicosapentaenoyl ethanolamide, and eicosapenaenoyl glycerol were identified in their milk by liquid chromatography-mass spectrometry and correlations to dietary fatty acids were assessed. Results Participants were not consuming recommended amounts of docosahexaenoic acid. Significant correlations ( p ≤ .05) were only found between dietary docosahexaenoic and eicosapentaenoic acids and the concentrations of these in human milk. Moreover, only dietary docosahexaenoic acid was correlated ( p = .031) with its corresponding endocannabinoid, docosahexaenoyl glycerol. Conclusions To the best of our knowledge, this may be one of the first studies evaluating relationships between dietary long-chain polyunsaturated fatty acids and multiple endocannabinoids in human milk. Our findings suggest that endocannabinoid concentrations could be modulated by dietary precursors. Future research studies can be designed based on these data to better elucidate the roles of endocannabinoids in human milk for infant health and development.

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Section: Discussionmentioning

confidence: 77%

Maternal Dietary Fatty Acids and Their Relationship to Derived Endocannabinoids in Human Milk

et al. 2021

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“…Levels of ARA were also unchanged in alcohol-treated rats relative to controls in both HC and ECX. Amounts were quantified by HPLC-MS analysis of area under the curve compared to known standards according to methods described (Smith et al, 2018). Average BACs in the study were less than originally predicted, but as alcohol doses were prepared in vanilla Ensure Plus and supplemented with olive oil, the vehicle for DHA supplementation, the lower-than-expected BAC is attributed in part to the high caloric intake during gavage.…”

Section: Discussionmentioning

confidence: 95%

Moderate blood alcohol and brain neurovulnerability: Selective depletion of calcium‐independent phospholipase A2, omega‐3 docosahexaenoic acid, and its synaptamide derivative as a potential harbinger of deficits in anti‐inflammatory reserve

Schreiber

Tajuddin

Kouzoukas

et al. 2021

Alcoholism Clin & Exp Res

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Background: Repetitive, highly elevated blood alcohol (ethanol) concentrations (BACs) of 350 to 450 mg/dl over several days cause brain neurodegeneration and coincident neuroinflammation in adult rats localized in the hippocampus (HC), temporal cortex (especially the entorhinal cortex; ECX), and olfactory bulb (OB). The profuse neuroinflammation involves microgliosis, increased proinflammatory cytokines, and elevations of Ca +2 -dependent phospholipase A2 (cPLA2) and secretory PLA2 (sPLA2), which both mobilize proinflammatory ω-6 arachidonic acid (ARA). In contrast, Ca +2independent PLA2 (iPLA2) and anti-inflammatory ω-3 docosahexaenoic acid (DHA), a polyunsaturated fatty acid regulated primarily by iPLA2, are diminished. Furthermore, supplemented DHA exerts neuroprotection. Given uncertainties about the possible effects of lower circulating BACs that are common occurring during short-term binges, we examined how moderate BACs affected the above inflammatory events, and the impact of supplemented DHA. Methods and results:Young adult male rats sustaining upper-moderate BACs (~150 mg/dl) from once-daily alcohol intubations were sacrificed with appropriate controls after 1 week. The HC, ECX and OB were quantitatively examined using immunoblotting, neurodegeneration staining, and lipidomics assays. Whereas neurodegeneration, increases in cPLA2 IVA, sPLA2 IIA, and ARA, and microglial activation were not detected, the HC and ECX regions demonstrated significantly reduced iPLA2 levels. Levels of DHA and synaptamide, its anti-inflammatory N-docosahexaenoylethanolamide derivative, also were lower in HC, and DHA supplementation prevented the iPLA2 decrements in HC. Additionally, adult mice maintaining upper-moderate BACs from limited alcohol binges had reduced midbrain iPLA2 levels. Conclusions:The apparently selective depletion by moderate BACs of the metabolically linked anti-inflammatory triad of hippocampal iPLA2, DHA, and synaptamide, and of iPLA2 in the ECX, potentially indicates an unappreciated deficit in brain antiinflammatory reserve that may be a harbinger of regional neurovulnerability.

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“…Human milk also contains other endocannabinoid-like N-acylethanolamines (NAE) such as N-stearoylanolamine (SEA), N-palmitoylamine (PEA), N-oleoylethanolamine (OEA), N-eicosapentaenoylethanolamine (EPEA) and N-docosahexaenoylethanolamine (synaptamide, DHEA). The reported concentrations of these compounds are generally within a similar range to that of AEA (0.04-9 nM) [28,[52][53][54]. The metabolic functions of these compounds are important during early life: OEA, for example, induces satiety, inhibits food intake, and increases energy catabolism [55][56][57].…”

Section: Endocannabinoids and Endocannabinoid-like Metabolites In Hummentioning

confidence: 87%

“…However, these compounds may act in the gut before degradation, although the presence of endocannabinoid receptors in the GI system has not been clearly demonstrated except in inflammatory conditions [61]. A significant correlation was observed between the level of synaptamide and the precursor DHA [53], suggesting that maternal supplementation of DHA can raise the synaptamide level in human milk. Likewise, the levels of other NAEs in human milk can be manipulated by the maternal intake of corresponding fatty acid-rich supplements or diet.…”

Section: Endocannabinoids and Endocannabinoid-like Metabolites In Hummentioning

confidence: 98%

Arachidonic Acid in Human Milk

Salem

Dael

2020

Nutrients

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Breastfeeding is universally recommended as the optimal choice of infant feeding and consequently human milk has been extensively investigated to unravel its unique nutrient profile. The human milk lipid composition is unique and supplies specifically long-chain polyunsaturated fatty acids (LC-PUFAs), in particular, arachidonic acid (ARA, 20:4n–6) and docosahexaenoic acid (DHA, 22:6n–3). Arachidonic acid (ARA) is the most predominant long-chain polyunsaturated fatty acid in human milk, albeit at low concentrations as compared to other fatty acids. It occurs predominantly in the triglyceride form and to a lesser extent as milk fat globule membrane phospholipids. Human milk ARA levels are modulated by dietary intake as demonstrated by animal and human studies and consequently vary dependent on dietary habits among mothers and regions across the globe. ARA serves as a precursor to eicosanoids and endocannabinoids that also occur in human milk. A review of scientific and clinical studies reveals that ARA plays an important role in physiological development and its related functions during early life nutrition. Therefore, ARA is an important nutrient during infancy and childhood and, as such, appropriate attention is required regarding its nutritional status and presence in the infant diet. Data are emerging indicating considerable genetic variation in encoding for desaturases and other essential fatty acid metabolic enzymes that may influence the ARA level as well as other LC-PUFAs. Human milk from well-nourished mothers has adequate levels of both ARA and DHA to support nutritional and developmental needs of infants. In case breastfeeding is not possible and infant formula is being fed, experts recommend that both ARA and DHA are added at levels present in human milk.

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N-docosahexaenoylethanolamine detected in human breast milk

Cited by 7 publications

References 16 publications

Maternal Dietary Fatty Acids and Their Relationship to Derived Endocannabinoids in Human Milk

Maternal Dietary Fatty Acids and Their Relationship to Derived Endocannabinoids in Human Milk

Moderate blood alcohol and brain neurovulnerability: Selective depletion of calcium‐independent phospholipase A2, omega‐3 docosahexaenoic acid, and its synaptamide derivative as a potential harbinger of deficits in anti‐inflammatory reserve

Arachidonic Acid in Human Milk

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