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

Chapman, Kent D.; Moore, Thomas

doi:10.1104/pp.102.3.761

Cited by 42 publications

(27 citation statements)

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“…Such an activity was described previously in dog brain tissue, but its cellular localization and physiological regulation has remained elusive thus far (Natarajan et al, 1983;Schmid et al, 1990). Moreover, the results illustrated in Table 2 appear to rule out the participation in neuronal NAPE biosynthesis of other known mechanisms of amino group N-acylation, including those implicated in the synthesis of NAPE in higher plants (Chapman and Moore, 1993) and of N-acylsphinganine in mammalian tissues (Kishimoto, 1983). While this study was under review, a similar N-acyltransferase activity was also described in rat testis (Sugiura et al, 1996).…”

mentioning

confidence: 79%

“…Experimental evidence suggests that NAPE may be produced by enzymatic N-acylation of PE (Hazlewood and Dawson, 1975;Schmid et al, 1990;Chapman and Moore, 1993). Two possible acyl group donors have been postulated to participate in this reaction: glycerophospholipids, in bacteria and animal tissues (Hazlewood and Dawson, 1975;Schmid et al, 1990), and free fatty acids, in plant tissues (Chapman and Moore, 1993).…”

Section: Resultsmentioning

confidence: 99%

“…Two possible acyl group donors have been postulated to participate in this reaction: glycerophospholipids, in bacteria and animal tissues (Hazlewood and Dawson, 1975;Schmid et al, 1990), and free fatty acids, in plant tissues (Chapman and Moore, 1993). Another acyl donor, fatty acyl-coenzyme A, participates in the N-acylation of sphinganine to N-acylsphinganine, a key step in the pathway of ceramide biosynthesis (Kishimoto, 1983).…”

Section: Resultsmentioning

confidence: 99%

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Biosynthesis of an Endogenous Cannabinoid Precursor in Neurons and its Control by Calcium and cAMP

et al. 1996

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Understanding the mechanisms involved in the biogenesis ofN-arachidonoylethanolamine (anandamide) andNpalmitoylethanolamine is important in view of the possible role of these lipids as endogenous cannabinoid substances. Anandamide (which activates cannabinoid CB1 receptors) andN-palmitoylethanolamine (which activates a CB2-like receptor subtype in mast cells) may both derive from cleavage of precursor phospholipid,N-acylphosphatidylethanolamine (NAPE), catalyzed by Ca2+-activated D-type phosphodiesterase activity. We report here that thede novobiosynthesis of NAPE is enhanced in a Ca2+-dependent manner when rat cortical neurons are stimulated with the Ca2+-ionophore ionomycin or with membrane-depolarizing agents such as veratridine and kainate. This reaction is likely to be mediated by a neuronalN-acyltransferase activity, which catalyzes the transfer of an acyl group from phosphatidylcholine to the ethanolamine moiety of phosphatidylethanolamine. In addition, we show that Ca2+-dependent NAPE biosynthesis is potentiated by agents that increase cAMP levels, including forskolin and vasoactive intestinal peptide. Our results thus indicate that NAPE levels in cortical neurons are controlled by Ca2+ions and cAMP. Such regulatory effect may participate in maintaining a supply of cannabimimeticN-acylethanolamines during synaptic activity, and prime target neurons for release of these bioactive lipids.

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confidence: 79%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Biosynthesis of an Endogenous Cannabinoid Precursor in Neurons and its Control by Calcium and cAMP

et al. 1996

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“…Homogenates were filtered through four layers of presoaked (with homogenization medium) cheesecloth and used directly for enzyme assays and protein estimations. NAPE synthase assays were conducted by previously developed methods (Chapman and Moore, 199313). Reactions were initiated by adding [l-14C]palmitic acid (0.25 pCi [4.4 nmol] of [14C]palmitic acid in 2.5 pL of ethanol) to 0.5 mL of homogenate and briefly vortexing.…”

Section: Nape Synthase Assaymentioning

confidence: 99%

“…Reactions were stopped by the addition of 2 mL of hot propanol (70°C). The synthesis of [14C]NAPE from [l-14C]palmitic acid was assessed after extraction of lipids from the assay reaction mixtures and separation by TLC (Chapman and Moore, 199313). Radioactive NAPE was identified and quantified by radiometric scanning (Bioscan [Washington, DC] system 200 imaging scanner) of TLC plates (Chapman et al, 199513).…”

Section: Nape Synthase Assaymentioning

confidence: 99%

N-Acylphosphatidylethanolamine in Dry and Imbibing Cottonseeds (Amounts, Molecular Species, and Enzymatic Synthesis)

et al. 1995

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KAcylphosphatidylethanolamine (NAPE), an unusual acylated derivative of phosphatidylethanolamine (PE), was recently shown to be synthesized from PE and free fatty acids i n cotyledons of cotton (Gossypium hirsutum L.) seedlings (K.D. Chapman, T.S. Moore [1993] Plant Physiol 102: 761-769). Here we report that NAPE is present in dry seeds of cotton and increases with time of imbibition from 2.31 nmol/seed in dry seeds to 4.26 nmol/seed i n 4-h-soaked seeds. Total phospholipid/seed also increased such that the relative percentage of NAPE was similar i n dry and soaked seeds (2.3 mol% compared to 2.6 mol%, respectively). The major molecular species of NAPE were identified in both dry and soaked seeds by fast atom bombardment mass spectrometry and collisionally activated dissociation tandem mass spectrometry as 16:0/18:2-PE(Kpalmitoyl), 16:0/18:2-PE(N-linoleoyl), and 18:2/18:2-PE(Kpalmitoyl). l h e specific activity of NAPE synthase in seed extracts increased with increasing time of imbibition from 35 pmol h-' mg-' protein in dry seeds to 129 pmol h-' mg-' protein i n 4-h-soaked seeds. Collectively, our results indicate that NAPE is present in dry cottonseeds and synthesized during imbibition. The biosynthesis of NAPE provides a mechanism for maintaining membrane integrity during seed rehydration and may indicate that NAPE plays a protective role i n intracellular membranes of plant tissues, as has been suggested for intracellular membranes of animal tissues.NAPE, which was first identified as a minor constituent of wheat flour (Bomstein, 1965), has recently become recognized as a widespread, albeit minor, phospholipid component in intracellular membranes of plants (Chapman and

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The N‐Acylethanolamine‐Mediated Regulatory Pathway in Plants

Kilaru

Blancaflor

Venables

et al. 2007

Chemistry & Biodiversity

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While cannabinoids are secondary metabolites synthesized by just a few plant species, N-acylethanolamines (NAEs) are distributed widely in the plant kingdom, and are recovered in measurable, bioactive quantities in many plant-derived products. NAEs in higher plants are ethanolamides of fatty acids with acyl-chain lenghts of C12-C(18) and zero to three C=C bonds. Generally, the most-abundant NAEs found in plants and vertebrates are similar, including NAE 16 : 0, 18 : 1, 18 : 2, and 18 : 3. Like in animal systems, NAEs are formed in plants from N-acylphosphatidylethanolamines (NAPEs), and they are hydrolyzed by an amidase to yield ethanolamine and free fatty acids (FFA). Recently, a homologue of the mammalian fatty acid amide hydrolase (FAAH-1) was identified in Arabidopsis thaliana and several other plant species. Overexpression of Arabidopsis FAAH (AtFAAH) resulted in plants that grew faster, but were more sensitive to biotic and abiotic insults, suggesting that the metabolism of NAEs in plants resides at the balance between growth and responses to environmental stresses. Similar to animal systems, exogenously applied NAEs have potent and varied effects on plant cells. Recent pharmacological approaches combined with molecular-genetic experiments revealed that NAEs may act in certain plant tissues via specific membrane-associated proteins or by interacting with phospholipase D-alpha, although other, direct targets for NAE action in plants are likely to be discovered. Polyunsaturated NAEs can be oxidized via the lipoxygenase pathway in plants, producing an array of oxylipin products that have received little attention so far. Overall, the conservation of NAE occurrence and metabolic machinery in plants, coupled with the profound physiological effects of elevating NAE content or perturbing endogenous NAE metabolism, suggest that an NAE-mediated regulatory pathway, sharing similarities with the mammalian endocannabinoid pathway, indeed exists.

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

Cited by 42 publications

References 15 publications

Biosynthesis of an Endogenous Cannabinoid Precursor in Neurons and its Control by Calcium and cAMP

Biosynthesis of an Endogenous Cannabinoid Precursor in Neurons and its Control by Calcium and cAMP

N-Acylphosphatidylethanolamine in Dry and Imbibing Cottonseeds (Amounts, Molecular Species, and Enzymatic Synthesis)

The N‐Acylethanolamine‐Mediated Regulatory Pathway in Plants

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