N-Acylethanolamines in human reproductive fluids

Herbert Schuel, Lani J. Burkman, Jack Lippes, Kent Crickard, Ellyn Forester, Daniele Piomelli, Andrea Giuffrida

Research output: Contribution to journalArticle

164 Citations (Scopus)

Abstract

N-Acylethanolamines (NAEs) are an important family of lipid-signaling molecules. Arachidonylethanolamide (anandamide) (AEA), palmitoylethanolamide (PEA), and oleoylethanolamide (OEA) are co-produced from similar phospholipid precursors when neurons are stimulated. AEA is an endogenous agonist (endocannabinoid) for cannabinoid receptors. It binds with higher affinity to type CB1 than to type CB2 cannabinoid receptors. PEA does not bind to CB1, while the hypothesis that it reacts with putative CB2-like receptors has been questioned. OEA does not activate currently known cannabinoid receptors, but it mimics the effects of AEA and cannabinoids in reducing the fertilizing capacity of sea urchin sperm. OEA and PEA also act as entourage compounds by inhibiting the hydrolysis of AEA by fatty acid amide hydrolase. Cannabinoid receptors and/or AEA are present in mammalian reproductive organs including the testis, epididymis, prostate, ovary, uterus, sperm, preimplantation embryo and placenta, as well as prostatic and mammary carcinomas. We now report that analysis by high-performance liquid chromatography/mass spectrometry (HPLC/MS) shows the presence of AEA, PEA, and OEA in human seminal plasma, mid-cycle oviductal fluid, follicular fluid, amniotic fluid, milk, and fluids from malignant ovarian cysts. Previous studies showed that AEA-signaling via cannabinoid receptors regulates capacitation and fertilizing potential of human sperm, early embryonic development and blastocyst implantation into the uterine mucosa of rodents, as well as proliferation of human mammary and prostatic carcinomas. Current results imply that NAEs also may modulate follicular maturation and ovulation, normal and pathological ovarian function, placental and fetal physiology, lactation, infant physiology, and behavior. Collectively, these findings suggest that NAEs in human reproductive fluids may help regulate multiple physiological and pathological processes in the reproductive system, and imply that exogenous cannabinoids delivered by marijuana smoke might impact these processes. This study has potential medical and public policy ramifications because of the incidence of marijuana abuse by adolescents and adults in our society, previously documented reproductive effects of marijuana, and the ongoing debate about medicinal use of marijuana and cannabinoids.

Original languageEnglish (US)
Pages (from-to)211-227
Number of pages17
JournalChemistry and Physics of Lipids
Volume121
Issue number1-2
DOIs
StatePublished - Dec 31 2002
Externally publishedYes

Fingerprint

Cannabinoid Receptors
Cannabinoids
Cannabis
Cannabinoid Receptor CB2
Spermatozoa
Fluids
Physiology
Medical Marijuana
Marijuana Abuse
Breast Neoplasms
Physiological Phenomena
Cannabinoid Receptor Agonists
Infant Behavior
Follicular Fluid
Endocannabinoids
Ovarian Cysts
Sea Urchins
Epididymis
Plasma (human)
Blastocyst

Keywords

  • Amniotic fluid
  • Eicosanoids
  • Endocannabinoids
  • Fertilization
  • Follicular fluid
  • Milk
  • Ovarian cysts
  • Oviductal fluid
  • Reproduction
  • Seminal plasma

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics

Cite this

Schuel, H., Burkman, L. J., Lippes, J., Crickard, K., Forester, E., Piomelli, D., & Giuffrida, A. (2002). N-Acylethanolamines in human reproductive fluids. Chemistry and Physics of Lipids, 121(1-2), 211-227. https://doi.org/10.1016/S0009-3084(02)00158-5

N-Acylethanolamines in human reproductive fluids. / Schuel, Herbert; Burkman, Lani J.; Lippes, Jack; Crickard, Kent; Forester, Ellyn; Piomelli, Daniele; Giuffrida, Andrea.

In: Chemistry and Physics of Lipids, Vol. 121, No. 1-2, 31.12.2002, p. 211-227.

Research output: Contribution to journalArticle

Schuel, H, Burkman, LJ, Lippes, J, Crickard, K, Forester, E, Piomelli, D & Giuffrida, A 2002, 'N-Acylethanolamines in human reproductive fluids', Chemistry and Physics of Lipids, vol. 121, no. 1-2, pp. 211-227. https://doi.org/10.1016/S0009-3084(02)00158-5
Schuel H, Burkman LJ, Lippes J, Crickard K, Forester E, Piomelli D et al. N-Acylethanolamines in human reproductive fluids. Chemistry and Physics of Lipids. 2002 Dec 31;121(1-2):211-227. https://doi.org/10.1016/S0009-3084(02)00158-5
Schuel, Herbert ; Burkman, Lani J. ; Lippes, Jack ; Crickard, Kent ; Forester, Ellyn ; Piomelli, Daniele ; Giuffrida, Andrea. / N-Acylethanolamines in human reproductive fluids. In: Chemistry and Physics of Lipids. 2002 ; Vol. 121, No. 1-2. pp. 211-227.
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