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206 E.B. Blancaflor, K.D. Chapman Fig.14.1. Structures of selected cannabinoids. a ∆ 9 -Tetrahydrocannabinol, the major active ingredient in marijuana, is a strong ligand for cannabinoid 1 receptors in mammalian brains. b Anandamide is an N-acylethanolamine (NAE) with a 20-carbon acyl chain and four double bonds. It has a wide range of neuromodulatory and physiological functions in vertebrates, and is drawn in two different conformations. c NAE types identified and quantified in plants CB receptors is somewhat surprising given the lack of obvious structural similarity with THC, but nearly all physiological effects elicited by marijuana have been attributed to anandamide and the metabolism of NAEs is now considered an integral part of the “endocannabinoid signaling system”. The activity of anandamide at the CB1 receptor has been attributed by some (Reggio 2003) to its ability to adopt alternative conformations (Fig. 14.1b). Although anandamide is the most studied NAE type in vertebrates, otherendogenousNAEssuchasN-oleoylethanolamine (NAE18:1) and N-palmitoylethanolamine (NAE16:0; Fig. 14.1c) elicit a number of biolog-
14 N-Acylethanolamines in Plants 207 ical effects in animals, including satiety (LoVerme et al. 2005) and antiinflammatory responses (Fowler 2003), respectively. Some of the cellular processesmediatedbyNAEsappeartobemediatedbybothreceptordependent and receptor-independent pathways. For example, anandamide bindingtoCB1receptorsisknowntostimulateGi/o proteins, which in turn influences the activity of a series of second messengers and proteins, including adenylate cyclase, voltage-gated calcium channels, K + channels, phosphatidyl 3-kinase and mitogen-activated protein (MAP) kinase (De Petrocellis et al. 2004; De Fonseca et al. 2005). On the other hand, experiments with mouse cell cultures showing that NAE induction of transcription and MAP kinase phosphorylation are not inhibited by Gi/o protein blockers or CB1 receptor antagonists can be taken as evidence for receptorindependent signaling (Berdyshev et al. 2001). The widespread occurrence of NAEs in various plant species (Chapman 2004), the recent cloning of a plant enzyme involved in the hydrolysis of NAE (Shrestra et al. 2003) and the identification of high-affinity NAE binding proteins in plant tissues whose binding appears to be influenced by CB receptor antagonists (Tripathy et al. 2003) point to intriguing parallels to mammalian endocannabinoid signaling. In this chapter, we review progress in plant NAE research focusing on metabolism and prospective functions while highlighting avenues for future work with the hope of generating excitement in this emerging field within plant physiology. 14.2 NAE Structure and Occurrence in Plants NAEs are fatty acid derivatives with amide linkages to ethanolamine (Fig. 14.1). As such, they are electrically neutral, and as expected have limited solubility in aqueous solutions. Various NAE types have been identified in animals (Schmid et al. 1990), higher plants (Chapman 2004) and some microorganisms (Schmid et al. 1990). For the most part the acyl moieties of NAEs are a reflection of the fatty acid compositions of the parent organisms, although the precise profiles (and quantities) of NAEs in a given organism vary from tissue to tissue. Generally NAEs are present in amounts approximating nanograms per gram of fresh weight, but under certain pathological conditions, NAE levels accumulate to micrograms per gram of fresh weight (Schmid et al. 1990; Chapman 2004). This is particularly striking under conditions of ischemia in mammalian heart and brain, where NAEs accumulate in damaged tissues, but are barely detectable in nearby unaffected tissues (Schmid et al. 1990). In plants, NAEs were first identified in processed, seed-derived products in the 1950s, but not until the 1990s did it become evident that
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František Baluška · Stefano Manc
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Dr. František Baluška University
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VI Preface turn, reward the ants by
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VIII Preface of olfactory response.
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Contents 1 The Green Plant as an In
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Contents XIII 6 Signals and Targets
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Contents XV 11 Amino Acid Transport
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Contents XVII 15 Regulation of Plan
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Contents XIX 21.3 Conclusions and P
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Contents XXI 27.3.2 Catechin Induce
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XXIV Contributors Correa-Aragunde,
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XXVI Contributors Lamattina, L. (e-
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XXVIII Contributors Song, C. Depart
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1 The Green Plant as an Intelligent
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2 Neurobiological View of Plants an
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38 P.W. Barlow Thestimulipresentedt
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40 P.W. Barlow that a tropism is su
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42 P.W. Barlow the auxin flow into
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44 P.W. Barlow afferentnervousimpul
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46 P.W. Barlow analysis. In particu
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48 P.W. Barlow reception of his boo
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50 P.W. Barlow Iijima M, Kono Y (19
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4 How Can Plants Choose the Most Pr
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66 P.M. Neumann Finally, I examined
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68 P.M. Neumann evolutionary progre
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70 P.M. Neumann conclusion is that
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72 P.M. Neumann resources from matu
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6 Signals and Targets Triggered by
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6TargetsofSI 77 6.1.2 Self-Incompat
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6TargetsofSI 79 by Yang 2002) has p
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6TargetsofSI 81 al. 2002). Thus, SI
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6TargetsofSI 83 Fig.6.2. PrABP80 ha
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6TargetsofSI 85 many of the genes e
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6TargetsofSI 87 [Ca 2+ ]i may signa
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6TargetsofSI 89 is crosstalk betwee
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6TargetsofSI 91 Hepler PK, Vidali L
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6TargetsofSI 93 Snowman BN, Kovar D
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96 T. Nürnberger, B. Kemmerling Wh
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98 T. Nürnberger, B. Kemmerling Fo
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100 T. Nürnberger, B. Kemmerling p
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102 T. Nürnberger, B. Kemmerling i
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104 T. Nürnberger, B. Kemmerling r
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106 T. Nürnberger, B. Kemmerling F
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108 T. Nürnberger, B. Kemmerling M
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8 Nitric Oxide Involvement in Incom
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124 M.L. Lanteri et al. 9.1.1 Auxin
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126 M.L. Lanteri et al. Fig.9.1. Sc
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128 M.L. Lanteri et al. Fig.9.2. NO
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130 M.L. Lanteri et al. 9.3.1 Nitri
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132 M.L. Lanteri et al. Fig.9.3. Sc
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134 M.L. Lanteri et al. Bellamine J
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136 M.L. Lanteri et al. Pagnussat G
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138 S.J. Murch H 3C CH3 CH3 N H 2C
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140 S.J. Murch edible plants (Manch
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142 S.J. Murch However, over the la
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144 S.J. Murch of monoamine, amino
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146 S.J. Murch On Guam and in other
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148 S.J. Murch 10.4 Conclusions and
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150 S.J. Murch Lindstrom H, Luthman
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11 Amino Acid Transport in Plants a
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17 Touch-Responsive Behaviors and G
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17 Touch-Responsive Behaviors and G
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18 Oscillations in Plants Sergey Sh
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18 Oscillations in Plants 263 Tempo
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18 Oscillations in Plants 265 Dries
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18 Oscillations in Plants 267 backg
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18 Oscillations in Plants 269 The f
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18 Oscillations in Plants 271 prehe
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18 Oscillations in Plants 273 Cardo
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18 Oscillations in Plants 275 Shaba
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278 K.Trebacz,H.Dziubinska,E.Krol W
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280 K.Trebacz,H.Dziubinska,E.Krol T
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282 K.Trebacz,H.Dziubinska,E.Krol E
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284 K.Trebacz,H.Dziubinska,E.Krol 1
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286 K.Trebacz,H.Dziubinska,E.Krol n
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288 K.Trebacz,H.Dziubinska,E.Krol D
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290 K.Trebacz,H.Dziubinska,E.Krol S
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292 R. Stahlberg, R.E. Cleland, E.
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310 E.Davies,B.Stankovic It is assu
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312 E.Davies,B.Stankovic 21.2 Evide
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314 E.Davies,B.Stankovic Fig.21.3.
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316 E.Davies,B.Stankovic Relative m
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318 E.Davies,B.Stankovic 1992; Beel
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320 E.Davies,B.Stankovic Hentze MW,
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322 J. Fromm, S. Lautner in the ran
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324 J. Fromm, S. Lautner cells (Sam
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326 J. Fromm, S. Lautner 22.5 Ion C
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328 J. Fromm, S. Lautner hastobedon
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330 J. Fromm, S. Lautner Beilby MJ,
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332 J. Fromm, S. Lautner Williams S
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334 S. Mancuso, S. Mugnai like the
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336 S. Mancuso, S. Mugnai 2,000 nM
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338 S. Mancuso, S. Mugnai the fourt
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340 S. Mancuso, S. Mugnai “slow-w
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342 S. Mancuso, S. Mugnai 23.6 Airb
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344 S. Mancuso, S. Mugnai that tree
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346 S. Mancuso, S. Mugnai Fort C, F
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348 S. Mancuso, S. Mugnai Pophof B,
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24 Electrophysiology and Phototropi
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370 E. Wagner et al. Table 25.1. Fl
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372 E. Wagner et al. Exudation [µl
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374 E. Wagner et al. metabolism at
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376 E. Wagner et al. The circadian
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378 E. Wagner et al. Fig.25.5. Time
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380 E. Wagner et al. Fig.25.7. Patt
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382 E. Wagner et al. Fig.25.9. Time
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384 E. Wagner et al. Fig.25.11. a K
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386 E. Wagner et al. 25.9 Conclusio
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388 E. Wagner et al. Lecharny A, Wa
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26 Signals and Signalling Pathways
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404 L.G. Perry et al. properties (S
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406 L.G. Perry et al. Fig.27.1. A s
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408 L.G. Perry et al. phytotoxins i
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410 L.G. Perry et al. monooxygenase
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412 L.G. Perry et al. 27.4 (±)-Cat
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414 L.G. Perry et al. (±)-catechin
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416 L.G. Perry et al. mineralizatio
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418 L.G. Perry et al. Dyer AR (2004
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420 L.G. Perry et al. Singh HP, Bat
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422 V.Ninkovic,R.Glinwood,J.Petters
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436 Subject Index defense 67, 95-10
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438 Subject Index sieve-tube-elemen
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