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2016 ; 41
(4
): 281-92
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Naturally Produced Defensive Alkenal Compounds Activate TRPA1
#MMPMID26843529
Blair NT
; Philipson BI
; Richards PM
; Doerner JF
; Segura A
; Silver WL
; Clapham DE
Chem Senses
2016[May]; 41
(4
): 281-92
PMID26843529
show ga
(E)-2-alkenals are aldehydes containing an unsaturated bond between the alpha and
beta carbons. 2-alkenals are produced by many organisms for defense against
predators and secretions containing (E)-2-alkenals cause predators to stop
attacking and allow the prey to escape. Chemical ecologists have described many
alkenal compounds with 3-20 carbons common, having varied positions of double
bonds and substitutions. How do these defensive alkenals act to deter predators?
We have tested the effects of (E)-2-alkenals with 6-12 carbons on transient
receptor potential channels (TRP) commonly found in sensory neurons. We find that
(E)-2-alkenals activate transient receptor potential ankyrin subtype 1 (TRPA1) at
low concentrations-EC50s 10-100 µM (in 0 added Ca(2+) external solutions). Other
TRP channels were either weakly activated (TRPV1, TRPV3) or insensitive (TRPV2,
TRPV4, TRPM8). (E)-2-alkenals may activate TRPA1 by modifying cysteine side
chains. However, target cysteines include others beyond the 3 in the
amino-terminus implicated in activation, as a channel with cysteines at 621, 641,
665 mutated to serine responded robustly. Related chemicals, including the
aldehydes hexanal and decanal, and (E)-2-hexen-1-ol also activated TRPA1, but
with weaker potency. Rat trigeminal nerve recordings and behavioral experiments
showed (E)-2-hexenal was aversive. Our results suggest that TRPA1 is likely a
major target of these commonly used defensive chemicals.
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