Pungent and Tingling Compounds in Asian Cuisine

Galopin, Christophe; Furrer, Stefan; Goeke, Andreas

doi:10.1021/bk-2003-0867.ch009

Cited by 28 publications

(30 citation statements)

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“…In order to provide more information about structure-activity relationships of the pungent taste for the sanshoolrelated compounds (Fig. 7), a variety of derivatives was synthesized by Galopin et al (2004). These results confirmed that a Z-double bond in the acyl chain is a Tables 3 and 4 Phytochem Rev key element for the sensory properties, but it is not the only one.…”

Section: Structure-activity Relationshipsmentioning

confidence: 75%

Alkamides: a critical reconsideration of a multifunctional class of unsaturated fatty acid amides

Greger

2015

Phytochem Rev

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Alkamides are natural products formed by connecting straight-chain, mostly unsaturated, aliphatic acids with various amines by an amide linkage. More than 300 derivatives are known from eight plant families consisting of various combinations of 200 acids with 23 amines. Apart from a few saturated derivatives alkamides with unsaturated acid parts are grouped into compounds with purely olefinic patterns and those with olefinic and acetylenic linkages. Derived from C 18 oleic acid the acid parts are modified either by chain elongations to C 28 or by oxidative shortenings to C 4 acid residues. Substrate and regiospecific desaturases and acetylenases are responsible for their characteristic patterns of unsaturation. Amine parts are derived from various amino acids by decarboxylation. Beside the widespread isobutylamines alkamides with six-and five-membered ring amines and those with phenylalanine derived amines are characteristic for the Asteraceae and Piperaceae while benzylamines are restricted to the Brassicaceae. Within the Asteraceae 2-methylbutylamine distinguishes the tribe Heliantheae from Anthemideae characterized by ring amines. Alkamides with elongated olefinic acid parts are mainly found in Piperaceae and Brassicaceae while acetylenic acid parts are typical for Asteraceae. A wide variety of biological activities ranges from the characteristic pungent/ tingling property and high insecticidal toxicity to significant antifungal, antibacterial, antiprotozoal, molluscicidal, cercaricidal, and acaricidal activity. They also act as plant growth-promoting substances. Position and stereochemistry of the double bonds are essential for the different qualities of the pungent taste. Medically alkamides possess anti-inflammatory and analgesic properties and are responsible for immunomodulatory and cannabinomimetic effects.

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Section: Structure-activity Relationshipsmentioning

confidence: 75%

Alkamides: a critical reconsideration of a multifunctional class of unsaturated fatty acid amides

Greger

2015

Phytochem Rev

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“…dihydrospilanthol (21) (Ley et al, 2004). Further unsaturation (alkenic and/or alkynic) generally leads to stronger effects in which the presence of a Z configuration is preferable (Bryant and Mezine, 2002;Galopin et al, 2004;Ley et al, 2004, Ley et al, 2005aSugai et al, 2005). The unnatural 2E,4Z pellitorine cis-isomer (316) has a profound tingling effect compared to the natural all-trans pellitorine (Ley et al, 2004).…”

Section: Tingling and Related Organoleptic Effectsmentioning

confidence: 99%

Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

Boonen

Bronselaer

Nielandt

et al. 2012

Journal of Ethnopharmacology

132

109

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a b s t r a c tEthnopharmacological relevance: N-Alkylamides (NAAs) are a promising group of bioactive compounds, which are anticipated to act as important lead compounds for plant protection and biocidal products, functional food, cosmeceuticals and drugs in the next decennia. These molecules, currently found in more than 25 plant families and with a wide structural diversity, exert a variety of biologicalpharmacological effects and are of high ethnopharmacological importance. However, information is scattered in literature, with different, often unstandardized, pharmacological methodologies being used. Therefore, a comprehensive NAA database (acronym: Alkamid) was constructed to collect the available structural and functional NAA data, linked to their occurrence in plants (family, tribe, species, genus). Materials and methods: For loading information in the database, literature data was gathered over the period 1950-2010, by using several search engines. In order to represent the collected information about NAAs, the plants in which they occur and the functionalities for which they have been examined, a relational database is constructed and implemented on a MySQL back-end. Results: The database is supported by describing the NAA plant-, functional-and chemical-space. The chemical space includes a NAA classification, according to their fatty acid and amine structures. Conclusions: The Alkamid database (publicly available on the website http://alkamid.ugent.be/) is not only a central information point, but can also function as a useful tool to prioritize the NAA Q8 choice in the evaluation of their functionality, to perform data mining leading to quantitative structure-property relationships (QSPRs), functionality comparisons, clustering, plant biochemistry and taxonomic evaluations.

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“…In order to investigate the "gustophore" in various taste molecules, structure/activity investigations based on systematic sensory studies with pure reference compounds have been successfully performed in the past for umamitasting and/or taste-enhancing carboxylic acids [5], bittertasting amino acids and peptides [26,27], bitter-tasting 1-oxo-2,3-dihydro-1H-indolizinium-6-olates [28], sweettasting 2-(4-methoxybenzoyl)benzoic acid derivatives [29,30], pungent and/or tingling shanshool and bungeanool derivatives [31], and, very recently, for 2-(1-pyrrolidinyl)-2-cyclopenten-1-ones and 3-(1-pyrrolidinyl)-2(5H)-furanones exhibiting a physiological cooling effect [32].…”

Section: Introductionmentioning

confidence: 99%

Systematic studies of structure and physiological activity of alapyridaine. A novel food‐born taste enhancer

Soldo

Frank

Ottinger

et al. 2004

Molecular Nutrition Food Res

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By application of taste dilution analysis (+)-(S)-1-(1-carboxyethyl)-5-hydroxy-2-(hydroxymethyl)-pyridinium inner salt was recently successfully identified as a multimodal taste enhancer in beef bouillon. While being taste-less on its own, this so-called alapyridaine was found to intensify the human perception of sweet, salty, and umami taste. To gain information on the molecular requirements of this novel class of taste enhancer, a range of structurally related pyridinium betaines were synthesized, purified, and their physiological activities sensorially evaluated. Removal or modification of the hydroxyl and the hydroxymethyl group, respectively, induced a loss in bioactivity, thus indicating the 2-(hydroxymethyl)-5-hydroxypyridinium moiety as an essential structural element for taste enhancement. Regarding the amino substituent, neither the prolongation or removal of the alkyl chain or the carboxy function in the 1-(1-carboxy-2-ethyl)-moiety, nor the incorporation of an additional carboxy function led to any active derivative, thus demonstrating that also the structure of the nitrogen substituent is rather conserved for taste enhancement. But substitution of the methyl group by a benzyl group yielded a compound showing similar taste enhancing activities as found for alapyridaine. Interestingly, additional insertion of glycine between the 1-(1-carboxy-2-phenylethyl)-moiety and the pyridinium ring resulted in a compound eliciting comparable taste enhancing effects as shown for the compound lacking the glycine spacer. In contrast to these multimodal taste enhancers, substitution of the alanine moiety in alapyridaine by an arginine moiety revealed an one-dimensional taste enhancer exclusively increasing the human sensitivity for salty taste.

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Pungent and Tingling Compounds in Asian Cuisine

Cited by 28 publications

References 0 publications

Alkamides: a critical reconsideration of a multifunctional class of unsaturated fatty acid amides

Alkamides: a critical reconsideration of a multifunctional class of unsaturated fatty acid amides

Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

Systematic studies of structure and physiological activity of alapyridaine. A novel food‐born taste enhancer

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