Chemical structures of odorants that suppress ion channels in the olfactory receptor cell

Kishino, Yukako; Kato, Hiroyuki; Kurahashi, Takashi; Takeuchi, Hiroko

doi:10.1007/s12576-011-0142-2

Cited by 12 publications

(8 citation statements)

References 29 publications

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“…8 Within structurally similar substances, the degree of suppression is nearly proportional to their oil/water partition coefficient, especially at the same pH (Log D ). 12 Also in the present study, substances having similar Log D showed similar SRs. Because of the time and hydrophobicity dependence, it is hypothesised that the suppression effect is started from the integration of these suppressive substances into the lipid bilayer of the plasma membrane.…”

Section: Discussionsupporting

confidence: 76%

“…ORCs were enzymatically dissociated from olfactory epithelia of newts ( Cynops pyrrhogaster ) as previously described, and were identified by their morphology and electrical properties. 12,14,15 The animal was used because they have larger ORCs than other vertebrates. Experiments were performed in compliance with the latest ethical guidelines for animal experimentation at the Osaka University based on international experimental regulations.…”

Section: Methodsmentioning

confidence: 99%

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Suppression of olfactory signal transduction by insecticides

Takeuchi

Kurahashi

2019

npj Sci Food

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2,4,6-Trichloroanisole (TCA) is a well-known, potent off-flavour compound present in various foods and beverages. TCA has been hypothesised to be a universal cause of flavour loss experienced in daily life. Here, however, we show that titres for the suppression of olfactory transducer channels caused by low-quality bananas are much higher than those for that caused by the TCA itself contained in the banana. We resurveyed other components of low-quality bananas and found that bananas also contain an insecticide (chlorpyrifos), and that it suppresses olfactory transducer channels. Other insecticides also suppressed olfactory transducer channels. Hence, even after passing safety examinations, certain insecticides may decrease the quality of foods and beverages by reducing their intrinsic scents.

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Section: Discussionsupporting

confidence: 76%

Section: Methodsmentioning

confidence: 99%

Suppression of olfactory signal transduction by insecticides

Takeuchi

Kurahashi

2019

npj Sci Food

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“…As shown in the present study, the solution in the puffer pipette was diluted by one or two orders of magnitude when ejected into the superfusion bath. Stimulus solutions were also applied by using a U-tube system (26).…”

Section: Methodsmentioning

confidence: 99%

“…We further applied TCA and other drugs with a U-tube system (26), by which the chemicals can be directly applied at more accurate concentrations (Fig. 4B).…”

Section: +mentioning

confidence: 99%

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2,4,6-Trichloroanisole is a potent suppressor of olfactory signal transduction

Takeuchi

Kato

Kurahashi

2013

Proc. Natl. Acad. Sci. U.S.A.

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We investigated the sensitivity of single olfactory receptor cells to 2,4,6-trichloroanisole (TCA), a compound known for causing cork taint in wines. Such off-flavors have been thought to originate from unpleasant odor qualities evoked by contaminants. However, we here show that TCA attenuates olfactory transduction by suppressing cyclic nucleotide-gated channels, without evoking odorant responses. Surprisingly, suppression was observed even at extremely low (i.e., attomolar) TCA concentrations. The high sensitivity to TCA was associated with temporal integration of the suppression effect. We confirmed that potent suppression by TCA and similar compounds was correlated with their lipophilicity, as quantified by the partition coefficient at octanol/water boundary (pH 7.4), suggesting that channel suppression is mediated by a partitioning of TCA into the lipid bilayer of plasma membranes. The rank order of suppression matched human recognition of offflavors: TCA equivalent to 2,4,6-tribromoanisole, which is much greater than 2,4,6-trichlorophenol. Furthermore, TCA was detected in a wide variety of foods and beverages surveyed for odor losses. Our findings demonstrate a potential molecular mechanism for the reduction of flavor.olfactory masking | ion channel | patch-clamp T hroughout culinary history, consumers have been disturbed by naturally generated off-flavor substances that can greatly reduce the palatability of foods and beverages. Because off-flavors appear at very low concentrations of contaminants, chemical identification of responsible compounds has been limited. One of the most potent off-flavor compounds identified to date is 2,4,6-trichloroanisole (TCA), known specifically for inducing a cork taint in wines (1). In general, off-flavor compounds have been thought to induce unpleasant exogenous smells (2-9), and would therefore be expected to excite specific olfactory receptors (10) transducing malodors. However, we found that TCA did not generate excitatory responses in single olfactory receptor cells (ORCs), but potently suppressed cyclic nucleotide-gated (CNG) channels in these cells. Because CNG channels play a key role in olfactory transduction, suppression of these channels suggests a reduction of endogenous odors, rather than an addition of exogenous odors. Surprisingly, TCA exerted a much more potent suppressive effect on CNG channels (100-1,000-fold) than other known olfactory masking agents that have been widely used in perfumery. It was also more potent than a well-known CNG channel blocker, L-cis-diltiazem. We could account for such high suppressive potency in terms of temporal integration and slow recovery from suppression by TCA. The order of potency of CNG suppression by TCA analogues or precursors was identical to that of the human detection of the corresponding off-flavors, i.e., TCA equivalent to 2,4,6-tribromoanisole(TBA), which is much greater than 2,4,6-trichlorophenol (TCP; precursor of TCA), suggesting that cork taint is related to TCA suppression of CNG channels. We further confi...

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The Mechanism of Olfaction

Sell¹

2014

Chemistry and the Sense of Smell

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Chemical structures of odorants that suppress ion channels in the olfactory receptor cell

Cited by 12 publications

References 29 publications

Suppression of olfactory signal transduction by insecticides

Suppression of olfactory signal transduction by insecticides

2,4,6-Trichloroanisole is a potent suppressor of olfactory signal transduction

The Mechanism of Olfaction

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