Structure–Odor Activity Studies on Monoterpenoid Mercaptans Synthesized by Changing the Structural Motifs of the Key Food Odorant 1-<i>p</i>-Menthene-8-thiol

Schoenauer, Sebastian; Schieberle, Peter

doi:10.1021/acs.jafc.6b01645

Cited by 37 publications

(50 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Thiols are important carriers of information-as key food odorants, determining the aroma of foods [6,21], as body odors [18,19], or as environmental odors [20]. The observation that thiols, compared to other volatiles, frequently display particularly low odor thresholds [23][24][25]101], sprouted various theories trying to explain this behavior, with the aim to gain an understanding of odorant information coding at the receptor level. Common to all of these theories is the association of a thiol-receptor interaction with participation of transition metal ions such as copper, zinc, or nickel [27-31, 46, 47].…”

Section: Discussionmentioning

confidence: 99%

“…Thiols play an outstanding role in human olfaction, for instance as body odor [15][16][17][18][19], environmental odors [20], and especially as key food odorants (KFOs), which appear in foods at concentrations above their odor threshold, and critically determine the aroma of foods [21]. Thiol odorants often show very low odor thresholds [6,[21][22][23][24][25]. The olfactory sensitivity for thiols is shown not only for humans but also for spider monkeys (Ateles geoffroyi), squirrel monkeys (Saimiri sciureus), and pigtail macaque (Macaca nemestrina) [26].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Copper-mediated thiol potentiation and mutagenesis-guided modeling suggest a highly conserved copper-binding motif in human OR2M3

Haag

Ahmed

Reiss

et al. 2019

Cell. Mol. Life Sci.

View full text Add to dashboard Cite

Sulfur-containing compounds within a physiological relevant, natural odor space, such as the key food odorants, typically constitute the group of volatiles with the lowest odor thresholds. The observation that certain metals, such as copper, potentiate the smell of sulfur-containing, metal-coordinating odorants led to the hypothesis that their cognate receptors are metalloproteins. However, experimental evidence is sparse-so far, only one human odorant receptor, OR2T11, and a few mouse receptors, have been reported to be activated by sulfur-containing odorants in a copper-dependent way, while the activation of other receptors by sulfur-containing odorants did not depend on the presence of metals. Here we identified an evolutionary conserved putative copper interaction motif CC/CSSH, comprising two copper-binding sites in TMH5 and TMH6, together with the binding pocket for 3-mercapto-2-methylpentan-1-ol in the narrowly tuned human receptor OR2M3. To characterize the copper-binding motif, we combined homology modeling, docking studies, site-directed mutagenesis, and functional expression of recombinant ORs in a cell-based, real-time luminescence assay. Ligand activation of OR2M3 was potentiated in the presence of copper. This effect of copper was mimicked by ionic and colloidal silver. In two broadly tuned receptors, OR1A1 and OR2W1, which did not reveal a putative copper interaction motif, activation by their most potent, sulfur-containing key food odorants did not depend on the presence of copper. Our results suggest a highly conserved putative copper-binding motif to be necessary for a copper-modulated and thiol-specific function of members from three subfamilies of family 2 ORs.

show abstract

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Copper-mediated thiol potentiation and mutagenesis-guided modeling suggest a highly conserved copper-binding motif in human OR2M3

Haag

Ahmed

Reiss

et al. 2019

Cell. Mol. Life Sci.

View full text Add to dashboard Cite

show abstract

“…This is particularly the case for some terpenic odorants, e.g., menthenethiol (“ Grapefruit, fresh, tropical, juicy and mango ”), methylthiomenthone (“ Catty‐ribes like, buchu, blackcurrant odor in dilution ”), thiolinalool (“ Fresh, fruity, bitter grapefruit note in dilution ”), and thiomenthone (“ Catty aroma; dull fruity black currant flavor”) . Several key structures linked to the odor quality of mercapto terpenoids have recently been examined, highlighting the role of an intracyclic double bond and a tertiary thiol group in the side chain.…”

Section: Discussionmentioning

confidence: 99%

Multivariate statistical analysis of a large odorants database aimed at revealing similarities and links between odorants and odors

Tromelin

Chabanet

Audouze

et al. 2017

Flavour & Fragrance J

View full text Add to dashboard Cite

The perception of odor is an important component of smell; the first step of odor detection, and the discrimination of structurally diverse odorants depends on their interactions with olfactory receptors (ORs). Indeed, the perception of an odor's quality results from a combinatorial coding, in which the deciphering remains a major challenge.Several studies have successfully established links between odors and odorants by categorizing and classifying data. Hence, the categorization of odors appears to be a promising way to manage odors.In the proposed study, we performed a computational analysis using odor descriptions of the odorants present in Flavor-Base 9th Edition (2013). We converted the Flavor-Base data into a binary matrix (1 when the odor note appears in the odor description, 0 otherwise). We retained 251 odor notes and 3508 odorants, considering only the orthonasal perception. Two categorization methods were performed: agglomerative hierarchical clustering (AHC), and self-organizing map (SOM). AHC was based on a measure of the distance between the elements performed by multidimensional scaling (MDS) for the odorants, and correspondence analysis (CA) for the odor notes.The results demonstrated that the SOM classes appeared to be less dependent on the frequency of the odor notes than those of the AHC clusters. SOMs are especially useful for identifying the associations between less than 4 or 5 odor notes within groups of odorants.The obtained results highlight subsets of odorants sharing similar groups of odor notes, suggesting an interesting and promising way of using computational approaches to help decipher olfactory coding.

show abstract

“…p-Menthene has been used as a starting material for the synthesis of many practical products, such as endoperoxides and (−) menthol, widely used in pharmacy and in the development of pesticides [10][11][12]. p-Menthene is also used as a food scent in fruit juices and other food products and since a long time in glues, adhesives, and resin synthesis process [13,14]. p-Menthane, which is a flavouring compound, is present for instance in peppermint [15].…”

Section: Introductionmentioning

confidence: 99%

Partial and Total Solvent-Free Limonene’s Hydrogenation: Metals, Supports, Pressure, and Water Effects

Moutombi

Fabiano‐Tixier

Clarisse

et al. 2020

Journal of Chemistry

View full text Add to dashboard Cite

Bio-based solvents menthene and menthane were obtained through limonene’s partial and total hydrogenation under various catalytic conditions. Heterogeneous catalysts based on different active metals and supports (carbon, alumina, and silica) were systematically tested for solvent-free total and partial hydrogenation of limonene under high and low hydrogen pressure. Influences of these catalysts on the formation of menthene, menthane, and cymene, a dehydrogenated product, were determined. The impact of water addition on the conversion and selectivity of the catalysts was also investigated. Amongst all tested catalysts, Rh/Alumina which was never tested for total and partial hydrogenation of limonene was the most effective as 1-menthene was quantitatively produced at low pressure (0.275 MPa) while menthane was mostly obtained at a higher pressure (2.75 MPa). Water addition on Rh/Alumina favoured menthene production even at high pressure. To propose menthane, menthene, and menthane/menthene mixture as an alternative to fossil-based solvents such as n-hexane for the extraction of natural products, β-carotene, vanillin, and rosmarinic acid solubilizations have been investigated. If a modeling approach using COSMO-RS software predicted a comparable solubilization of these 3 compounds for the 3 solvents, experimental assays revealed that menthene solubilizes β-carotene, vanillin, and rosmarinic acid three to five times better than n-hexane.

show abstract

Structure–Odor Activity Studies on Monoterpenoid Mercaptans Synthesized by Changing the Structural Motifs of the Key Food Odorant 1-p-Menthene-8-thiol

Cited by 37 publications

References 24 publications

Copper-mediated thiol potentiation and mutagenesis-guided modeling suggest a highly conserved copper-binding motif in human OR2M3

Copper-mediated thiol potentiation and mutagenesis-guided modeling suggest a highly conserved copper-binding motif in human OR2M3

Multivariate statistical analysis of a large odorants database aimed at revealing similarities and links between odorants and odors

Partial and Total Solvent-Free Limonene’s Hydrogenation: Metals, Supports, Pressure, and Water Effects

Contact Info

Product

Resources

About