Hydrolysis of N-acylated glycerophospholipids by phospholipases A2 and D: A method of identification and analysis

Schmid, Patricia C.; Natarajan, Viswanathan; Weis, Barbara K.; Schmid, Harald H.O.

doi:10.1016/0009-3084(86)90022-8

Cited by 27 publications

(21 citation statements)

References 31 publications

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“…The NAPE fractions were hydrolyzed with phospholipase D ( Streptomyces chromofuscus ) as described (22) in the presence of deuterated NAEs to serve as internal standards. NAEs were isolated by TLC on silica gel H, using hexane:diethylether:acetone:glacial acetic acid (40:20:20:1, by vol) as developing solvent, and derivatized.…”

Section: Methodsmentioning

confidence: 99%

Production and physiological actions of anandamide in the vasculature of the rat kidney.

Deutsch¹,

Goligorsky²,

Schmid³

et al. 1997

J. Clin. Invest.

327

276

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The endogenous cannabinoid receptor agonist anandamide is present in central and peripheral tissues. As the kidney contains both the amidase that degrades anandamide and transcripts for anandamide receptors, we characterized the molecular components of the anandamide signaling system and the vascular effects of exogenous anandamide in the kidney. We show that anandamide is present in kidney homogenates, cultured renal endothelial cells (

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Section: Methodsmentioning

confidence: 99%

Production and physiological actions of anandamide in the vasculature of the rat kidney.

Deutsch¹,

Goligorsky²,

Schmid³

et al. 1997

J. Clin. Invest.

327

276

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“…After cooling, the NAE-tBDMS derivatives were extracted into 50 l of hexane for gas chromatography-mass spectrometry (GC-MS). The NAPE fractions were reacted with phospholipase A 2 (Trimeresurus flavoviridis) and phospholipase D (Streptomyces chromofuscus) as described to release the NAE moiety (22). The d4 NAE standard mixture was added to the tubes before the phospholipase A 2 reaction, and NAEs were subsequently purified by TLC on layers of silica gel H, developed in hexane͞diethylether͞acetone͞glacial acetic acid (40:20:20:1, by vol), scraped off, eluted, and derivatized.…”

Section: Methodsmentioning

confidence: 99%

Changes in anandamide levels in mouse uterus are associated with uterine receptivity for embryo implantation

Schmid

Paria

Krebsbach

et al. 1997

Proc. Natl. Acad. Sci. U.S.A.

240

166

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Anandamide (N-arachidonoylethanolamine) is an endogenous ligand for both the brain-type (CB1-R) and spleen-type (CB2-R) cannabinoid receptors. This investigation demonstrates that the periimplantation mouse uterus contains the highest levels of anandamide (142-1345 pmol͞ mol lipid P; 1-7 g͞g wet weight) yet discovered in a mammalian tissue. The levels f luctuate with the state of pregnancy; down-regulation of anandamide levels is associated with uterine receptivity, while up-regulation is correlated with uterine refractoriness to embryo implantation. Anandamide levels are highest during the nonreceptive phase in the pseudopregnant uterus and in the interimplantation sites, and lowest at the site of embryo implantation. The lower levels of uterine anandamide at the implantation sites may be a mechanism by which implanting embryos protect themselves from the detrimental effects of this endogenous ligand. We also observed a reduced rate of zona-hatching of blastocysts in vitro in the presence of anandamide, and inhibition of implantation by systemic administration of a synthetic cannabinoid agonist CP 55,940. These adverse effects were reversed by SR141716A, a specific CB1-R antagonist. Taken together, the results suggest that an aberrant synthesis of anandamide and͞or expression of the cannabinoid receptors in the uterus͞embryo may account for early pregnancy failure or female infertility.

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“…This NAPE was suspended in 1 mL of warm (34°C) diethyl ether. Enzymic hydrolysis of NAPE (by phospholipase A 2 and then phospholipase D; Schmid et al, 1986) and isolation and separation of derivatives was performed as described previously (Chapman and Moore, 1993).…”

Section: Assessment Of the Position Of Acyl Addition To Napementioning

confidence: 99%

Catalytic Properties of a Newly Discovered Acyltransferase That Synthesizes N-Acylphosphatidylethanolamine in Cottonseed (Gossypium hirsutum L.) Microsomes

Chapman

Moore

1993

Plant Physiol.

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We recently demonstrated that cotyledons of cotton (Gossypium hirsutum 1.) seedlings synthesize N-acylphosphatidylethanolamine (NAPE), an unusual acylated derivative of phosphatidylethanolamine (PE), during postgerminative growth (K.D. Chapman and T.S. Moore [1993] Arch Biochem Biophys 301: 21-33). Here, we report the discovery of an acyltransferase enzyme, fatty acid: diacylphosphatidylethanolamine N-acyltransferase (designated NAPE synthase), that synthesizes NAPE from PE and free fatty acids (FFA) in cottonseed microsomes. ["CINAPE was synthesized from ["C]palmitic acid and endogenous PE in a time-, pH-, temperature-, and protein concentration-dependent manner. ]palmitic acid into NAPE at low concentrations (10 p~, highaffinity site) but not at high concentrations (50 PM, low-affinity site), indicating that the two putative sites can be distinguished by their fatty acid preferences.

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Hydrolysis of N-acylated glycerophospholipids by phospholipases A2 and D: A method of identification and analysis

Cited by 27 publications

References 31 publications

Production and physiological actions of anandamide in the vasculature of the rat kidney.

Production and physiological actions of anandamide in the vasculature of the rat kidney.

Changes in anandamide levels in mouse uterus are associated with uterine receptivity for embryo implantation

Catalytic Properties of a Newly Discovered Acyltransferase That Synthesizes N-Acylphosphatidylethanolamine in Cottonseed (Gossypium hirsutum L.) Microsomes

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