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  • Effects of synthetic alkamides on Arabidopsis fatty acid amide hydrolase activity and plant development.

Effects of synthetic alkamides on Arabidopsis fatty acid amide hydrolase activity and plant development.

Phytochemistry (2014-12-11)
Lionel Faure, Ronaldo Cavazos, Bibi Rafeiza Khan, Robby A Petros, Peter Koulen, Elison B Blancaflor, Kent D Chapman
ABSTRACT

Alkamides and N-acylethanolamines (NAEs) are bioactive, amide-linked lipids that influence plant development. Alkamides are restricted to several families of higher plants and some fungi, whereas NAEs are widespread signaling molecules in both plants and animals. Fatty acid amide hydrolase (FAAH) has been described as a key contributor to NAE hydrolysis; however, no enzyme has been associated with alkamide degradation in plants. Herein reported is synthesis of 12 compounds structurally similar to a naturally occurring alkamide (N-isobutyl-(2E,6Z,8E)decatrienamide or affinin) with different acyl compositions more similar to plant NAEs and various amino alkyl head groups. These "hybrid" synthetic alkamides were tested for activity toward recombinant Arabidopsis FAAH and for their effects on plant development (i.e., cotyledon expansion and primary root length). A substantial increase in FAAH activity was discovered toward NAEs in vitro in the presence of some of these synthetic alkamides, such as N-ethyllauroylamide (4). This "enhancement" effect was found to be due, at least in part, to relief from product inhibition of FAAH by ethanolamine, and not due to an alteration in the oligomerization state of the FAAH enzyme. For several of these alkamides, an inhibition of seedling growth was observed with greater results in FAAH knockouts and less in FAAH over-expressing plants, suggesting that these alkamides could be hydrolyzed by FAAH in planta. The tight regulation of NAE levels in vivo appears to be important for proper seedling establishment, and as such, some of these synthetic alkamides may be useful pharmacological tools to manipulate the effects of NAEs in situ.

MATERIALS
Product Number
Brand
Product Description

USP
Palmitic acid, United States Pharmacopeia (USP) Reference Standard
Palmitic acid, European Pharmacopoeia (EP) Reference Standard
Supelco
Palmitic acid, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
Supelco
Palmitic acid, Pharmaceutical Secondary Standard; Certified Reference Material
Sigma-Aldrich
n-Dodecyl β-D-maltoside, ≥98% (GC)
Sigma-Aldrich
n-Dodecyl β-D-maltoside, BioXtra, ≥98% (GC)
Sigma-Aldrich
Ethanolamine, liquid, BioReagent, suitable for cell culture, ≥98%
Sigma-Aldrich
Ethanolamine, ≥98%
Supelco
N,O-Bis(trimethylsilyl)trifluoroacetamide with trimethylchlorosilane, with 1% trimethylchlorosilane, for GC derivatization, LiChropur
Sigma-Aldrich
Palmitic acid, BioXtra, ≥99%
Supelco
Palmitic acid, analytical standard
Supelco
N,O-Bis(trimethylsilyl)trifluoroacetamide with trimethylchlorosilane, for GC derivatization, LiChropur, contains 1% TMCS, 99% (excluding TMCS)
Sigma-Aldrich
Ethanolamine, ≥99%
Sigma-Aldrich
Palmitic acid, ≥98% palmitic acid basis (GC)
Supelco
N,O-Bis(trimethylsilyl)trifluoroacetamide with trimethylchlorosilane, for GC derivatization, LiChropur, contains 10% TMCS, 98% (excluding TMCS)
Supelco
Ethanolamine, analytical standard
Supelco
Aucubin, analytical standard
Sigma-Aldrich
Palmitic acid, ≥98%, FCC, FG
Sigma-Aldrich
Lauric acid, ≥98%, FCC, FG
Sigma-Aldrich
Primuline, Dye content 50 %
Sigma-Aldrich
Ethanolamine, ACS reagent, ≥99.0%
Sigma-Aldrich
Propylamine, ≥99%
Sigma-Aldrich
Lauric acid, natural, ≥98%, FCC, FG
Sigma-Aldrich
Ethanolamine, purified by redistillation, ≥99.5%
Sigma-Aldrich
Propylamine, 98%
Sigma-Aldrich
Propylamine, purum, ≥99.0% (GC)
Aucubin, primary reference standard
Sigma-Aldrich
Ethanolamine, puriss. p.a., ACS reagent, ≥99.0% (GC/NT)
Sigma-Aldrich
Palmitic acid, ≥99%
Lauric acid, European Pharmacopoeia (EP) Reference Standard