StructureOdor Relationships of Semisynthetic <i>β</i>‐Santalol Analogs

Delasalle, Céline; March, Claire A. de; Meierhenrich, Uwe J.; Brevard, Hugues; Golebiowski, Jérôme; Baldovini, Nicolas

doi:10.1002/cbdv.201400082

Cited by 10 publications

(10 citation statements)

References 56 publications

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“…Introducing an alcohol or keto function significantly alters the olfactory properties of natural terpene hydrocarbons and artificial sesquiterpene‐like ketones . Selectively oxidized sesquiterpenes could thus serve for structure–odor relationship studies …”

Section: Resultsmentioning

confidence: 99%

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New Sesquiterpene Oxidations with CYP260A1 and CYP264B1 from Sorangium cellulosum So ce56

et al. 2015

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Sesquiterpenes are natural products derived from the common precursor farnesyl pyrophosphate (FPP) but are highly diverse in structure and function. Cytochrome P450 enzymes (P450s) exhibit the unique ability to introduce molecular oxygen into non-activated C-H bonds. In plant biosynthetic pathways, P450s commonly derivatize sesquiterpene hydrocarbons. However, the potential of bacterial P450s for terpene derivatization is still underinvestigated. This work compares the substrate specificities and regioselectivities of the sesquiterpene hydroxylases CYP260A1 and CYP264B1 from myxobacterium Sorangium cellulosum So ce56. Four tested substrate classes (eremophilanes, humulanes, caryophyllanes, and cedranes) were converted by both P450s. The achievable variety of oxidations is demonstrated on the model substrates (+)-nootkatone and zerumbone. Increasing the number of functionally investigated P450s, this study represents a step towards the selective derivatization of sesquiterpenes.

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Section: Resultsmentioning

confidence: 99%

“…[48] Selectively oxidized sesquiterpenes couldt hus serve for structure-odor relationship studies. [49]…”

Section: Applications Of the Oxidized Sesquiterpene Productsmentioning

confidence: 99%

New Sesquiterpene Oxidations with CYP260A1 and CYP264B1 from Sorangium cellulosum So ce56

et al. 2015

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“…The impact of sensitivity to this compound on food acceptability and selection has also been demonstrated: ‘sensitive’ and ‘insensitive’ subjects presented different preference patterns for foods containing cis‐3‐hexenol. Several halogenated volatiles, described as powerful odorants, have been identified as off‐odours in mineral water, orange juice, salted Gouda cheese, cocoa powder, dried fruit, wine, fish sauce, and chicken . However, specific anosmias to some of these compounds were found in 50% of the population, raising doubts as to the validity of panels selected at random or without due caution for quality control.…”

Section: Discussionmentioning

confidence: 99%

Molecular determinism of specific anosmia to 2‐bromo‐4‐methylphenol

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et al. 2016

Flavour & Fragrance J

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Several studies have revealed considerable variations in human chemosensory capacities. Considerable interindividual differences in sensitivity to various odorants and specific hyposmias are well known. Many chemical studies have focused on elucidating structure-odour relationships on the basis of detection threshold measurements. The basic idea of quantitative structure-activity relationship studies is that a molecule's structure provides information about its biological activity. In a recent sensory assay of 2-bromo-4-methylphenol, Barbe et al. (2014) highlighted a noticeable bimodal distribution of individual sensitivity with large interindividual differences. The aim of the present study was to investigate the link between the chemical structure of 2-bromo-4-methylphenol and this bimodal distribution. The olfactory phenotypes for a selection of six structurally related halogenated compounds were compared using detection thresholds determination. This study revealed that specific anosmia for 2-bromo-4-methylphenol was apparently linked to the halogenated substitution position

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“…Very different chemicals trigger a typical "camphor" smell, while a single molecule, the so-called "cat-ketone" odorant, elicit two totally different smells as a function of its concentration [4]. At best, such SOR rules are obtained for a very tiny fraction of the chemical space, emphasizing that they must be decomposed into sub-rules associated with given molecular topologies [5]. A simple, universal and perfect rule does probably not exist, but instead, a combination of several sub-rules should be put forward to encompass the complexity of SOR.…”

Section: Introductionmentioning

confidence: 99%

Local Subgroup Discovery for Eliciting and Understanding New Structure-Odor Relationships

et al. 2016

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Abstract. From a molecule to the brain perception, olfaction is a complex phenomenon that remains to be fully understood in neuroscience. A challenge is to establish comprehensive rules between the physicochemical properties of the molecules (e.g., weight, atom counts) and specific and small subsets of olfactory qualities (e.g., fruity, woody). This problem is particularly difficult as the current knowledge states that molecular properties only account for 30% of the identity of an odor: predictive models are found lacking in providing universal rules. However, descriptive approaches enable to elicit local hypotheses, validated by domain experts, to understand the olfactory percept. Based on a new quality measure tailored for multi-labeled data with skewed distributions, our approach extracts the top-k unredundant subgroups interpreted as descriptive rules description → {subset of labels}. Our experiments on benchmark and olfaction datasets demonstrate the capabilities of our approach with direct applications for the perfume and flavor industries.

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StructureOdor Relationships of Semisynthetic β‐Santalol Analogs

Cited by 10 publications

References 56 publications

New Sesquiterpene Oxidations with CYP260A1 and CYP264B1 from Sorangium cellulosum So ce56

New Sesquiterpene Oxidations with CYP260A1 and CYP264B1 from Sorangium cellulosum So ce56

Molecular determinism of specific anosmia to 2‐bromo‐4‐methylphenol

Local Subgroup Discovery for Eliciting and Understanding New Structure-Odor Relationships

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