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N-Acylethanolamines: Formation and Molecular
Composition of a New Class of Plant Lipids1
Kent D. Chapman*,
Swati Tripathy,
Barney Venables, and
Arland D. Desouza
Department of Biological Sciences, Division of Biochemistry and
Molecular Biology, University of North Texas, Denton, Texas 76203-5220
(K.D.C., S.T., A.D.D.); and TRAC Laboratories, 113 South Cedar,
Denton, Texas 76201 (B.V.)
Recently, the biosynthesis of an
unusual membrane phospholipid,
N-acylphosphatidylethanolamine (NAPE), was found to
increase in elicitor-treated tobacco (Nicotiana tabacum
L.) cells (K.D. Chapman, A. Conyers-Hackson, R.A. Moreau, S. Tripathy
[1995] Physiol Plant 95: 120-126). Here we report
that before induction of NAPE biosynthesis,
N-acylethanolamine (NAE) is released from NAPE in cultured tobacco cells 10 min after treatment with the fungal elicitor
xylanase. In radiolabeling experiments [14C]NAE (labeled
on the ethanolamine carbons) increased approximately 6-fold in the
culture medium, whereas [14C]NAPE associated with cells
decreased approximately 5-fold. Two predominant NAE molecular species,
N-lauroylethanolamine and
N-myristoylethanolamine, were specifically identified by
gas chromatography-mass spectrometry in lipids extracted from culture
medium, and both increased in concentration after elicitor treatment.
NAEs were found to accumulate extracellularly only. A microsomal
phospholipase D activity was discovered that formed NAE from NAPE; its
activity in vitro was stimulated about 20-fold by mastoparan,
suggesting that NAPE hydrolysis is highly regulated, perhaps by
G-proteins. Furthermore, an NAE amidohydrolase activity that catalyzed
the hydrolysis of NAE in vitro was detected in homogenates of tobacco
cells. Collectively, these results characterize structurally a new
class of plant lipids and identify the enzymatic machinery involved in
its formation and inactivation in elicitor-treated tobacco cells.
Recent evidence indicating a signaling role for NAPE metabolism in
mammalian cells (H.H.O. Schmid, P.C. Schmid, V. Natarajan [1996] Chem
Phys Lipids 80: 133-142) raises the
possibility that a similar mechanism may operate in plant cells.
1
This research was supported by grants from the
U.S. Department of Agriculture-National Research Initiative Competitive
Grants Program to K.D.C., agreement nos. 94-37304-1230 and
96-35304-3862.
*
Corresponding author; e-mail kent{at}jove.acs.unt.edu; fax
1-940-565-4136.
Plant Physiol. (1998) 116: 1163-1168
Copyright Clearance Center: 0032-0889/98/116/1163/06
© 1998 American Society of Plant Physiologists
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