Discovery of taste modulating octadecadien-12-ynoic acids in golden chanterelles (Cantharellus cibarius).

Abstract:

:Activity-guided fractionation in combination with taste dilution and comparative taste dilution analysis, followed by LC-MS and 1D/2D-NMR experiments, enabled the identification of several C18-acetylenic acids in chanterelles among which (9Z,15E)-14,17,18-trihydroxy-9,15-octadecadien-12-ynoic acid, (9Z,15E)-14-oxo-9,15-octadecadien-12-ynoic acid, (10E,15E)-9-hydroxy-14-oxo-10,15-octadecadien-12-ynoic acid, (10E,15E)-9-hydroperoxy-14-oxo-10,15-octadecadien-12-ynoic acid, (10E,15E)-9,14-dioxo-10,15-octadecadien-12-ynoic acid, (9Z,15E)-14-oxo-9,15-octadecadien-12-ynoic acid methyl ester, (9Z,15E)-17(18)-epoxy-14-oxo-9,15-octadecadien-12-ynoic acid methyl ester and (10E,14Z)-9-hydroperoxy-10,14-octadecadien-12-ynoic acid have not yet been reported in literature. Sensory evaluation in a basic taste recombinant revealed taste modulating thresholds for the octadecadien-12-ynoic acids in the range of 19-105 µmol/l. In comparison, three isolated octadecadienoic acids, namely (10E,14Z)-12-hydroxy-10,14-octadecadienoic acid, (9Z,11Z)-14,18-dihydroxy-9,11-octadecadienoic acid, and (9Z,11Z)-14,17,18-trihydroxy-9,11-octadecadienoic acid, respectively, did not show any taste modulating activity, thus pinpointing the putative key role of the acetylene moiety for kokumi enhancement.

journal_name

Food Chem

journal_title

Food chemistry

authors

Mittermeier VK,Dunkel A,Hofmann T

doi

10.1016/j.foodchem.2018.06.123

subject

Has Abstract

pub_date

2018-12-15 00:00:00

pages

53-62

eissn

0308-8146

issn

1873-7072

pii

S0308-8146(18)31096-3

journal_volume

269

pub_type

杂志文章
  • Preharvest treatments with malic, oxalic, and acetylsalicylic acids affect the phenolic composition and antioxidant capacity of coriander, dill and parsley.

    abstract::The effects of a preharvest treatment with malic (MA), oxalic (OA), or acetylsalicylic (ASA) acid at three concentrations (1, 2 and 3mM) on the bioactivity and antioxidant capacity of coriander, dill, and parsley were investigated. The antioxidant capacity of the herbs extracts was assayed by spectrophotometric method...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2017.01.067

    authors: El-Zaeddi H,Calín-Sánchez Á,Nowicka P,Martínez-Tomé J,Noguera-Artiaga L,Burló F,Wojdyło A,Carbonell-Barrachina ÁA

    更新日期:2017-07-01 00:00:00

  • Dispersive solid-phase extraction followed by high-performance liquid chromatography/tandem mass spectrometry for the determination of ricinine in cooking oil.

    abstract::A rapid and accurate method by liquid chromatography/tandem mass spectrometry (LC-MS/MS) using positive electrospray was established for the determination of ricinine in cooking oils. The homogenized samples, spiked with (13)C6-labelled ricinine as an internal standard, were extracted using ethanol/water (20:80, v/v) ...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2014.02.114

    authors: Cai M,Chen X,Wei X,Pan S,Zhao Y,Jin M

    更新日期:2014-09-01 00:00:00

  • Simultaneous determination of acrylamide, asparagine and glucose in food using short chain methyl imidazolium ionic liquid based ultrasonic assisted extraction coupled with analyte focusing by ionic liquid micelle collapse capillary electrophoresis.

    abstract::Acrylamide (AA) is a known lethal neurotoxin and carcinogen. AA is formed in foods during the browning process by the Maillard reaction of glucose (GL) with asparagine (AS). For the first time, the simultaneous online preconcentration and separation of AA, AS and GL using analyte focusing by ionic liquid micelle colla...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2015.05.047

    authors: Abd El-Hady D,Albishri HM

    更新日期:2015-12-01 00:00:00

  • Characterization of virgin olive oils produced with autochthonous Galician varieties.

    abstract::The interest of Galician oil producers (NW Spain) in recovering the ancient autochthonous olive varieties Brava and Mansa has increased substantially in recent years. Virgin olive oils produced by co-crushing both varieties in two different proportions, reflecting the usual and most common practice adopted in this reg...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2016.05.135

    authors: Reboredo-Rodríguez P,González-Barreiro C,Cancho-Grande B,Valli E,Bendini A,Gallina Toschi T,Simal-Gandara J

    更新日期:2016-12-01 00:00:00

  • Contribution of botanical origin and sugar composition of honeys on the crystallization phenomenon.

    abstract::The present work provides information regarding the statistical relationships among the palynological characteristics, sugars (fructose, glucose, sucrose, melezitose and maltose), moisture content and sugar ratios (F+G, F/G and G/W) of 136 different honey types (including bramble, chestnut, eucalyptus, heather, acacia...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2013.10.097

    authors: Escuredo O,Dobre I,Fernández-González M,Seijo MC

    更新日期:2014-04-15 00:00:00

  • Determination of trichothecenes and zearalenones in grain cereal, flour and bread by liquid chromatography tandem mass spectrometry.

    abstract::Although analytical methods have been already reported for legislated mycotoxins as trichothecenes and zearalenone (ZON) separately, we describe the optimization of a simple and rapid multimycotoxin method for the determination of a total of 12 mycotoxins simultaneously, nine trichothecenes (NIV, DON, FUS-X, DAS, 15-A...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2012.04.051

    authors: Juan C,Ritieni A,Mañes J

    更新日期:2012-10-15 00:00:00

  • Structure-activity relationship study between baicalein and wogonin by spectrometry, molecular docking and microcalorimetry.

    abstract::Flavones (e.g. baicalein and wogonin) extensively used worldwide in food preparation and traditional medicine. In this study, a systematically comparative study of their structure-activity relationships (SAR) on their interaction with BSA, antioxidant activity and antibacterial activity has been carried out by spectro...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2016.04.006

    authors: Tu B,Li RR,Liu ZJ,Chen ZF,Ouyang Y,Hu YJ

    更新日期:2016-10-01 00:00:00

  • Strawberries from integrated pest management and organic farming: phenolic composition and antioxidant properties.

    abstract::Consumer awareness, pesticide and fertilizer contaminations and environmental concerns have resulted in significant demand for organically grown farm produce. Consumption of berries has become popular among health-conscious consumers due to the high levels of valuable antioxidants, such as anthocyanins and other pheno...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2012.03.130

    authors: Fernandes VC,Domingues VF,de Freitas V,Delerue-Matos C,Mateus N

    更新日期:2012-10-15 00:00:00

  • Phenylalanine ammonia-lyase, flavanone 3β-hydroxylase and flavonol synthase enzyme activity by a new in vitro assay method in berry fruits.

    abstract::An HPLC method for the determination of phenylalanine ammonia-lyase, flavanone 3β-hydroxylase and flavonol synthase enzyme activity is proposed. This method is based on the determination of the compounds produced and consumed on the enzymatic reaction in just one chromatographic analysis. Optimisation of the method co...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2013.12.034

    authors: Flores G,De la Peña Moreno F,Blanch GP,Del Castillo ML

    更新日期:2014-06-15 00:00:00

  • Maillard reaction and caramelization during hazelnut roasting: A multiresponse kinetic study.

    abstract::A comprehensive kinetic model indicating the elementary steps of Maillard reaction and caramelization during hazelnut roasting was proposed based on a multi-response kinetic modeling approach. Changes in the concentrations of sucrose, fructose, glucose, amino acids, 3-deoxyglucosone, 1-deoxyglucosone, 3,4-dideoxygluco...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2016.11.159

    authors: Göncüoğlu Taş N,Gökmen V

    更新日期:2017-04-15 00:00:00

  • Betalain rich functional extract with reduced salts and nitrate content from red beetroot (Beta vulgaris L.) using membrane separation technology.

    abstract::An initial laboratory-scale evaluation of separation characteristics of membranes with nominal molecular weight cut-offs (NMWCO) ranging from 30kD down to 0.5kD indicated effective separation of betalains in the 0.5kD region. Subsequent pilot-level trials using 1kD, loose reverse osmosis (LRO) and reverse osmosis (RO)...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2016.07.132

    authors: Mereddy R,Chan A,Fanning K,Nirmal N,Sultanbawa Y

    更新日期:2017-01-15 00:00:00

  • Content evaluation of 4 furanocoumarin monomers in various citrus germplasms.

    abstract::Due to the furanocoumarin compounds in the fruit, the production and consumption of grapefruit have been affected in the past decades since the 'grapefruit juice effect' was declared. To provide elite germplasm and obtain knowledge for future citrus breeding programs, the contents of 4 furanocoumarin monomers (FCMs) i...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2015.04.007

    authors: Xu J,Ma L,Jiang D,Zhu S,Yan F,Xie Y,Xie Z,Guo W,Deng X

    更新日期:2015-11-15 00:00:00

  • Electrochemical fabrication of a novel ZnO/cysteic acid nanocomposite modified electrode and its application to simultaneous determination of sunset yellow and tartrazine.

    abstract::A new nanocomposite (ZnO/Cysteic acid) was deposited on glassy carbon electrode by cyclic voltammetry. Uniform deposition of the nanocomposite was observed by scanning electron microscopy. The electron transfer characteristics of two food additives, sunset yellow and tartrazine, were greatly improved on the modified e...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2017.01.071

    authors: Dorraji PS,Jalali F

    更新日期:2017-07-15 00:00:00

  • Factors affecting the digestibility of raw and gelatinized potato starches.

    abstract::The enzymatic digestibilities of raw and gelatinized starches in various potato starches, as well as sweet potato, cassava, and yam starches, were estimated, along with other starch properties, such as the phosphorus content, median granule size, and rapid visco analyzer (RVA) pasting properties. Furthermore, correlat...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2008.02.027

    authors: Noda T,Takigawa S,Matsuura-Endo C,Suzuki T,Hashimoto N,Kottearachchi NS,Yamauchi H,Zaidul IS

    更新日期:2008-09-15 00:00:00

  • Simultaneous characterisation of silver nanoparticles and determination of dissolved silver in chicken meat subjected to in vitro human gastrointestinal digestion using single particle inductively coupled plasma mass spectrometry.

    abstract::In this study, a chicken meat containing AgNPs (candidate reference material Nanolyse 14) has been used as a model matrix to study the fate and behaviour of AgNPs upon oral ingestion following an in vitro model that included saliva, gastric and intestinal digestions. The behaviour of a 40nm AgNPs standard solution dur...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2016.11.091

    authors: Ramos K,Ramos L,Gómez-Gómez MM

    更新日期:2017-04-15 00:00:00

  • Induction of phenolic metabolites and physiological changes in chamomile plants in relation to nitrogen nutrition.

    abstract::Alternative tools, such as the manipulation of mineral nutrition, may affect secondary metabolite production and thus the nutritional value of food/medicinal plants. We studied the impact of nitrogen (N) nutrition (nitrate/NO3(-) or ammonium/NH4(+) nitrogen) and subsequent nitrogen deficit on phenolic metabolites and ...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2013.07.074

    authors: Kováčik J,Klejdus B

    更新日期:2014-01-01 00:00:00

  • Effect of ripening inhibitor type on formation, stability, and antimicrobial activity of thyme oil nanoemulsion.

    abstract::The objective of this research was to study the impact of ripening inhibitor level and type on the formation, stability, and activity of antimicrobial thyme oil nanoemulsions formed by spontaneous emulsification. Oil-in-water antimicrobial nanoemulsions (10 wt%) were formed by titrating a mixture of essential oil, rip...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2017.10.084

    authors: Ryu V,McClements DJ,Corradini MG,McLandsborough L

    更新日期:2018-04-15 00:00:00

  • Metabolic profiling approach to determine phenolic compounds of virgin olive oil by direct injection and liquid chromatography coupled to mass spectrometry.

    abstract::A LC-MS method involving direct injection of extra-virgin olive oil (EVOO) - after a simple dilution - for determining its phenolic compounds has been developed. Optimization of the most appropriate solvent for sample dilution, selection of the optimum oil/solvent ratio, and establishment of column cleaning strategy a...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2017.03.139

    authors: Olmo-García L,Bajoub A,Monasterio RP,Fernández-Gutiérrez A,Carrasco-Pancorbo A

    更新日期:2017-09-15 00:00:00

  • Comparative study of the oxidative and physical stability of liposomal and nanoliposomal polyunsaturated fatty acids prepared with conventional and Mozafari methods.

    abstract::The relative oxidative stability of freshly prepared and stored liposomal and nanoliposomal systems of docosahexaenoic acid (DHA, 22:6 n-3) and eicosapentaenoic acid (EPA, 20:5 n-3) were investigated. The effects of organic solvents on the oxidative stability of liposomal polyunsaturated fatty acids (PUFAs) produced b...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2012.07.016

    authors: Rasti B,Jinap S,Mozafari MR,Yazid AM

    更新日期:2012-12-15 00:00:00

  • High-sensitivity determination of cadmium and lead in rice using laser-induced breakdown spectroscopy.

    abstract::Stability and sensitivity of toxic elements determination is still unsatisfactory in agricultural product using laser-induced breakdown spectroscopy (LIBS). A simple and low cost sample pretreatment method named solid-liquid-solid transformation method was proposed in this work. The target analytes of cadmium (Cd) and...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2018.07.214

    authors: Yang P,Zhou R,Zhang W,Yi R,Tang S,Guo L,Hao Z,Li X,Lu Y,Zeng X

    更新日期:2019-01-30 00:00:00

  • Effect of origin, breeding and processing conditions on the isotope ratios of bioelements in dry-cured ham.

    abstract::The stable isotope ratios (SIR) of the bioelements ((2)H/(1)H, (13)C/(12)C, (15)N/(14)N, (18)O/(16)O, (34)S/(32)S) of the defatted dry matter and marbling and subcutaneous fat fractions, were assessed on 86 ham samples belonging to six different types, with the aim of ascertaining the effect of origin and production s...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2012.06.084

    authors: Perini M,Camin F,Sánchez del Pulgar J,Piasentier E

    更新日期:2013-02-15 00:00:00

  • Metal ion interactions with methyl gallate characterized by UV spectroscopic and computational methods.

    abstract::A simple biologically active phenolic methyl gallate (MeG) was used as a model compound to identify the nature of the complexes it formed with Al3+, Fe3+, Cu2+, and Sn2+ as analyzed by ultraviolet (UV) spectroscopic and computational methods. The results showed that, among all the metal ions studied in the present stu...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2019.04.083

    authors: Zhang L,Liu Y,Hu X,Wang Y,Xu M

    更新日期:2019-09-30 00:00:00

  • Antioxidant and anti-inflammatory properties of Taiwanese yam (Dioscorea japonica Thunb. var. pseudojaponica (Hayata) Yamam.) and its reference compounds.

    abstract::Dioscorea japonica Thunb. var. pseudojaponica (DP) is consumed as food and widely used in traditional Chinese medicine in Taiwan. The aims of this study are to investigate the antioxidant and anti-inflammatory effects of ethanol extract of DP (EDP) and its reference compounds. Fingerprint chromatogram from HPLC indica...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2013.04.031

    authors: Chiu CS,Deng JS,Chang HY,Chen YC,Lee MM,Hou WC,Lee CY,Huang SS,Huang GJ

    更新日期:2013-11-15 00:00:00

  • Effects of PEF and heat pasteurization on PME activity in orange juice with regard to a new inactivation kinetic model.

    abstract::The inactivation kinetics of pectin methyl esterase (PME) during the shelf life (4°C-180 days) of freshly squeezed orange juice samples processed by both pulsed electric fields (PEF) and heat pasteurization (HP) was evaluated in the study. The PME inactivation level after the PEF (25.26 kV/cm-1206.2 μs) and HP (90°C-2...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2014.05.097

    authors: Agcam E,Akyıldız A,Evrendilek GA

    更新日期:2014-12-15 00:00:00

  • Changes in non-volatile taste components of button mushroom (Agaricus bisporus) during different stages of freeze drying and freeze drying combined with microwave vacuum drying.

    abstract::Button mushroom slices were dehydrated using freeze drying (FD) or FD combined with microwave vacuum drying (FMVD), and the non-volatile component profiles were studied. The results showed that the level of non-volatile components in button mushroom firstly increased during sublimation of FD/FMVD process and then fell...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2014.05.130

    authors: Pei F,Shi Y,Gao X,Wu F,Mariga AM,Yang W,Zhao L,An X,Xin Z,Yang F,Hu Q

    更新日期:2014-12-15 00:00:00

  • Fatty acids attached to all-trans-astaxanthin alter its cis-trans equilibrium, and consequently its stability, upon light-accelerated autoxidation.

    abstract::Fatty acid esterification, common in naturally occurring astaxanthin, has been suggested to influence both colour stability and degradation of all-trans-astaxanthin. Therefore, astaxanthin stability was studied as influenced by monoesterification and diesterification with palmitate. Increased esterification decelerate...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2015.08.077

    authors: de Bruijn WJ,Weesepoel Y,Vincken JP,Gruppen H

    更新日期:2016-03-01 00:00:00

  • Lycium ruthenicum studies: Molecular biology, Phytochemistry and pharmacology.

    abstract::Lycium ruthenicum has been used as ethnic medicine and nutraceutical food. Existing studies of L. ruthenicum can be classifies into three areas: (1) those in which molecular biology methods were used to study its origin, genetic variation and relationships with other species; (2) those in which phytochemical methods w...

    journal_title:Food chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.foodchem.2017.08.026

    authors: Wang H,Li J,Tao W,Zhang X,Gao X,Yong J,Zhao J,Zhang L,Li Y,Duan JA

    更新日期:2018-02-01 00:00:00

  • Film forming ability of gelatins from splendid squid (Loligo formosana) skin bleached with hydrogen peroxide.

    abstract::Properties of gelatin films from splendid squid (Loligo formosana) skin bleached with hydrogen peroxide (H(2)O(2)) at various concentrations (0-8% w/v) were investigated. Tensile strength (TS) and water vapour permeability (WVP) of films decreased, but elongation at break (EAB) increased (p<0.05) as the concentration ...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2012.11.069

    authors: Nagarajan M,Benjakul S,Prodpran T,Songtipya P,Nuthong P

    更新日期:2013-06-01 00:00:00

  • Controlled release of microencapsulated docosahexaenoic acid (DHA) by spray-drying processing.

    abstract::The omega-3-fatty acid, docosahexaenoic acid (DHA) 22:6 n-3, is an important food component for the visual and brain development of infants. In this study two approaches have been explored for the encapsulation of DHA in the pH dependant polymer hydroxyl-propyl-methyl-cellulose-acetate-succinate (HPMCAS). In the first...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2019.01.121

    authors: Loughrill E,Thompson S,Owusu-Ware S,Snowden MJ,Douroumis D,Zand N

    更新日期:2019-07-15 00:00:00

  • Application of the solvent extraction technique to investigation of the anti-inflammatory activity of adlay bran.

    abstract::The current study utilised a bioassay-directed chemical analysis scheme to screen the anti-inflammatory activity of fractions and compounds from adlay bran (AB). Liquid-liquid extraction couple with liquid chromatography-mass spectrometry (LC-MS) was applied to the isolation, analysis and identification of active comp...

    journal_title:Food chemistry

    pub_type: 杂志文章

    doi:10.1016/j.foodchem.2013.08.071

    authors: Huang DW,Wu CH,Shih CK,Liu CY,Shih PH,Shieh TM,Lin CI,Chiang W,Hsia SM

    更新日期:2014-02-15 00:00:00