LC TASTE AS A NOVEL TOOL FOR THE IDENTIFICATION OF FLAVOUR MODIFYING COMPOUNDS
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1 LC TASTE AS A NVEL TL FR THE IDENTIFICATIN F FLAVUR MDIFYING CMPUNDS K.V. Reichelt 1, R. Peter 2, M. Roloff 2, J.P. LEY 2, G.E. Krammer 2, and K.-H. Engel Technische Universität München, Chair of General Food Technology, Am Forum 2, D-8535 Freising-Weihenstephan, Germany Symrise GmbH & Co. KG, Flavor & Nutrition, Research & Innovation, P.. Box 1253, D-371 Holzminden, Germany Abstract LC Taste methodology, which allows direct correlation between analytical data and online in-vivo sensory evaluation, was tested for the ability to identify taste modulating compounds from complex plant derived matrices. Tests were carried out using the known flavour modifying compounds homoeriodictyol (HED), sterubin and hesperetin either alone or in combination to evaluate their taste modifying effects after fractionation via high temperature liquid chromatography. In addition, fractions of Herba Santa methanolic extract, containing these three compounds was also tested. Bitter masking and sweet enhancing effects, respectively, were clearly detectable in the relevant fractions. Introduction Flavour and taste modification (bitter masking, sweet or salt enhancing, etc.) is currently an important topic for the food industry (1, 2). In many products the contents of salt and nutritive sweet carbohydrates have to be reduced which leads to a change in taste profile. Compounds such as polyphenols which are added to various types of foods providing health benefits often show bitter taste. These unwanted side effects are in most cases not tolerated by the consumer. Flavour modifiers are commonly defined as substances which have no typical flavouring properties per se but which are able to modify the flavour profile of other flavouring substances. In combination with other flavouring substances and food ingredients these substances are able to modify the flavour profile of flavoured foods. This consequently leads to a modified perception of the foodstuff by panellists and consumers and is reflected in reproducible changes of flavour profiles in sensory (3). In addition to the fact that these compounds have little or no intrinsic taste, but show their effects only in the presence of taste-active compounds, detection of taste modifiers in natural sources is frequently hindered by the complexity of plant extracts which makes the work laborious as well as time and cost intensive. Typical methods developed for the identification flavour modifying compounds are taste dilution analysis (TDA), comparative taste dilution analysis (ctda) or dose over threshold (DoT) analysis, which in general are rather time consuming (4, 5, 6). To accelerate and to simplify the identification of novel taste modifying compounds from plant extracts, an extension of the known LC Taste methodology (7, 8) was developed, which allows correlating data from real-time analysis and in vivo detection of relevant taste modifying compounds by a specially trained sensory panel (Figure 1). 397
2 Figure 1. Schematic representation of LC Taste device. Experimental Chemicals and extracts. Homoeriodictyol (HED) and sterubin were isolated according to (9). Hesperetin was purchased from Sigma (Steinheim, Germany). Dried Eriodictyon californicum leaves (5 g) were treated with 3.2 l of boiling water for one hour to break up the plant material. The plant material was filtered, dried and extracted 3 times with 2. l of methanol each for one hour. The resulting methanolic extract was evaporated to dryness (97.7 g). High temperature high performance liquid chromatography (HTLC). The HPLC apparatus consisted of two pumps (SunChrom HPLC pump SunFlow ; SunChrom, Friedrichsdorf, Germany), an injector ( µl loop; Midas, Spark, AJ Emmen, The Netherlands), a column oven (Polaratherm Series 9; Selerity Technologies Inc., Salt Lake City, Utah, USA), an ELSD detector (Sedex 85 LT- ELSD, Sedere, Alfortville, Cedex, France) and a diode array detector (SunChrom SpectraFlow, SunChrom, Friedrichsdorf, Germany), monitoring the effluent in a wavelength range between nm and nm. Separations were performed with a Hamilton PRP-1 reversed phase column (Hamilton Company, Reno, Nevada, USA) in a 25 x 1 mm semi-preparative scale with a particle size of 1 μm. After injection of the sample ( µl full loop) the analysis was carried out at 1 C isotherm using a water/ethanol gradient with a flow rate of 3 ml/min to elute the compounds. Sensory studies. Thresholds for basic tastes were determined with a panel of specially trained, healthy persons without any reported taste disorders using sucrose, sodium chloride, citric acid, caffeine and mono sodium glutamate either as described in (1) or after fractionation via high temperature liquid chromatography. Masking and enhancing studies were done using paired comparison test method using water fractionated under the same conditions as a reference. Samples were blinded and coded and presented in randomized order. 398
3 Results In order to determine the performance of both the novel LC Taste technology and the panel, taste recognition thresholds for basic tastes were determined. There were no significant differences between LC Taste and conventional determination of thresholds. Furthermore, known taste modifying compounds such as HED, sterubin (9) and hesperetin (11) (Figure 2) were subjected to HTLC, diluted 1: 1 with standard solutions containing caffeine (5 ppm) and sucrose (5 %), respectively, to yield final concentrations of 5 ppm each and evaluated sensorially by the dedicated panel to determine bitter masking and sweet enhancing effects of these compounds (Figure 3). As a comparison, water was fractionated under the same conditions, diluted with the test solutions as described above and presented to the panellists. Normalized modulation probability factor of both samples, showing the presumption of a tested compound or fraction to have taste modulating effects was calculated as follows NMP = ( n n ) higher lower / n total Me Me H Me H Figure 2. Chemical structures of homoeriodictyol (HED), sterubin & hesperetin from Herba Santa (Eriodictyon californicum (H. & A.) Torr., Hydrophyllaceae). normalized modulation probability Hesperetin HED Sterubin Sweet enhancing Bitter masking Figure 3. NMP-factors for hesperetin, HED (tested as sodium salt) and sterubin tested as single compounds (5 ppm each) on caffeine and sucrose solution after fractionation via LC Taste (n= 15). A recombinate from methanolic Herba Santa extract was prepared, containing the before tested compounds HED ( ppm in final solution), hesperetin ( ppm) and sterubin ( ppm) and separated and fractionated via HTLC. The eluate was diluted 1:1 with the testing solutions containing sucrose or caffeine and evaluated by the sensory panel to determine the taste modulating properties of the recombinate fractions in comparison to samples containing no test compound (Figure 4). 399
4 sweet enhancing effects (1), (2) (3) bitter masking effects Figure 4. NMP-factors for hesperetin (1, ppm), HED (2, ppm; tested as sodium salt), and sterubin (3, ppm) tested as recombinate from Herba Santa extract on caffeine and sucrose solution after fractionation via LC Taste (n= 15). In addition, methanolic Herba Santa extract was separated via HTLC and fractionated. Selected fractions, including those containing HED, hesperetin and sterubin were diluted with testing solutions and evaluated sensorially by an expert panel (n= 8) to identify possible taste modulating effects (Figure 5). As described above, samples fractionated under the same conditions but containing no test compound served as reference samples. enhancing effect masking effect bitter sweet no effect Figure 5. NMP-factors for selected peaks from Herba Santa extract tested on sucrose and caffeine solution after fractionation via LC Taste (n= 8). It was shown that the taste modulating effects of the tested single compounds HED, hesperetin and sterubin were detectable by sensory analysis using LC Taste. The same effect was shown for a recombinate of Herba Santa extract, containing the three compounds mentioned above. Herba Santa extract was separated and fractionated via HTLC under the same conditions. Selected peaks were tested for their taste modulating properties using sucrose and caffeine solution as test solution. Two fractions, containing the taste modulating compounds HED, hesperetin and sterubin clearly showed sweet enhancing and bitter masking effects, respectively. In
5 addition to this known active compounds, three other fractions showed interesting sweet enhancing effects. Several other fractions did not seem to reduce but to enhance bitterness. These fractions will be analysed in detail to know which compounds are responsible for these effects. References 1. Ley J.P. (8) Chem. Percept. 1: Ley J.P., Blings M., Paetz S., Kindel G., Freiherr K., Krammer G.E., Bertram H.- J. (8) In Sweetness and Sweeteners Biology, Chemistry, and Psychophysics (Weerasinghe D.K., DuBois G.E., eds.), American Chemical Society: Washington, DC, USA, 8, pp Krammer G., personal communication. 4. ttinger H., Soldo T., Hofmann T. (3) J. Agric. Food Chem. 51: Soldo T., Hofmann T. (5) J. Agric. Food Chem. 53: Scharbert S., Hofmann T. (5) J. Agric. Food Chem. 53: Roloff M.; Erfurt H.; Kindel G.; Schmidt C.-.; Krammer G.E. (6) W 6/ Krammer G. et al. (6) In Flavour Science: Recent Advances and Trends (Bredie W.L.P., Petersen M.A., eds.), Elsevier: Amsterdam, Netherlands, pp Ley J.P.; Krammer G.; Reinders G.; Gatfield I.L.; Bertram H.-J. (5) J. Agric. Food Chem. 53: Deutsches Institut für Normung, e.v. (5) DIN 1959 Sensorische Prüfverfahren - Bestimmung der Geschmacksempfindlichkeit. 11. Ley J.P.; Kindel G.; Paetz S.; Riess T.; Haug M.; Schmidtmann R.; Kammer G.E. (7) W 7/
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