Abstract
Application of sequential solvent extraction and reverse phase high-performance liquid chromatography separation in combination with the taste dilution analysis, followed by liquid chromatography–mass spectroscopy and 1D/2D nuclear magnetic resonance experiments revealed 11 flavon-3-ol-O-glycosides as the key astringent and mouth-drying compounds in blanched leaves of spinach (Spinacia oleracea). Among these, in particular, 3′,5-dihydroxy-3-methoxy-6:7-methylendioxy-flavon-4′-O-β-d-glucuronide (3), 5-hydroxy-3,3′-dimethoxy-6:7-methylendioxy-flavon-4′-O-β-d-glucuronide (11), and patuletin-3-O-β-d-glucopyranosyl(1→6)-β-d-glucopyranoside (5) were found with the highest taste dilution factors. By means of the half-tongue test, the human taste thresholds of these astringent molecules were determined to be between 3.0 and 69.0 μmol/l (in water) with the lowest threshold found for the mouth-drying glucuronide (11). Although the glucuronides exhibited rather different taste thresholds, they showed rather similar human dose/response functions.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Aritomi M, Kawasaki T (1984) Three highly oxygenated flavone glucuronides in leaves of Spinacia oleracea. Phytochemistry 23(9):2043–2047
Aritomi M, Komori T, Kawasaki T (1986) Flavonol glycosides in leaves of Spinacia oleracea. Phytochemistry 25(1):231–234
Berahia T, Gaydou EM, Cerrati C, Wallet JC (1994) Mass spectrometry of polymethoxylated flavones. J Agric Food Chem 42:1697–1700
Bergquist SÅM, Gertsson UE, Knuthsen P, Olsson ME (2005) Flavonoids in baby spinach (Spinacia oleracea L.): changes during plant growth and storage. J Agric Food Chem 53:9459–9464
Czepa A, Hofmann T (2003) Structural and sensory characterization of compounds contributing to the bitter off-taste of carrots (Daucus carota L.) and carrot puree. J Agric Food Chem 51:3865–3873
Edenharder R, Keller G, Platt KL, Unger KK (2001) Isolation and characterization of structurally novel mutagenic flavonoids from spinach (Spinacia oleracea). J Agric Food Chem 49:2767–2773
Fang N, Mabry TJ (1989) Isolation and identification of some flavonoids from canned spinach. Rev Latinoamer Quim 20/1:42–44
Ferreres F, Castaner M, Tomas-Barberan FA (1997) Acylated flavonol glycosides from spinach leaves (Spinacia oleracea). Phytochem 45(8):1701–1705
Frank O, Ottinger H, Hofmann T (2001) Characterization of an intense bitter-tasting 1H,4H-quinolizinium-7-olate by application of the taste dilution analysis, a novel bioassay for the screening and identification of taste-active compounds in foods. J Agric Food Chem 49:231–238
Galopin C, Tigani L, Furrer S (2005) Structure property relationship of chemosensates. In: Hofmann T, Rothe M, Schieberle P (eds) State-of-the-art in flavour chemistry and biology. Proceedings of the 7th Wartburg Symposium, pp 61–67
Greenham J, Harborne JB, Williams CA (2003) Identification of lipophilic flavones and flavonols by comparative HPLC, TLC and UC spectral analysis. Phytochem Anal 14:100–118
Kidmose U, Knuthsen P, Edelenbos M, Justesen U, Hegelund E (2001) Carotenoids and flavonoids in organically grown spinach (Spinacia oleracea L.) genotypes after deep frozen storage. J Sci Food Agric 81:918–923
Lesschaeve I, Noble AC (2005) Polyphenols: factors influencing their sensory properties and their effects on food and beverage preferences. Am J Clin Nutr 81:330S–335S
Masanetz C, Guth H, Grosch W (1998) Fishy and hay-like off-flavour of dry spinach. Z Lebensm Unters Forsch 206:108–113
Näf R, Velluz A (2000) The volatile constituents of extracts of cooked spinach leaves. (Spinacia oleracea L.). Flavour Frag J 15:329–334
Ottinger H, Hofmann T (2003) Identification of the taste enhancer alapyridaine in beef broth and evaluation of its sensory impact by taste reconstitution experiments. J Agric Food Chem 51:6791–6796
Ottinger H, Bareth A, Hofmann T (2001) Characterization of natural “cooling” compounds formed from glucose and l-proline in dark malt by application of taste dilution analysis. J Agric Food Chem 49:1336–1344
Scharbert S, Holzmann N, Hofmann T (2004) Identification of the astringent taste compounds in black tea infusions by combining instrumental analysis and human bioresponse. J Agric Food Chem 52:3498–3508
Schwarz B, Hofmann T (2007a) Sensory-guided decomposition of red currant juice (Ribes rubrum) and structure determination of key astringent compounds. J Agric Food Chem 55:1394–1404
Schwarz B, Hofmann T (2007b) Isolation, structure determination, and sensory activity of mouth-drying and astringent nitorgen-containing phytochemicals isolated from red currants (Ribes rubrum). J Agric Food Chem 55:1405–1410
Stark T, Bareuther S, Hofmann T (2005) Sensory-guided decomposition of roasted cocoa nibs (Theobroma cacao) and structure determination of taste-active polyphenols. J Agric Food Chem 53:5407–5418
Wagner H, Maurer I (1977) Synthese von Polyhydroxy-Flavonolmethyläthern mit potentieller cytotoxischer Wirksamkeit—I. Tetrahedr 33:1405–1409
Winter M, Herrmann K (1986) Esters and glucosides of hydroxycinnamic acids in vegetables. J Agric Food Chem 34:616–620
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Brock, A., Hofmann, T. Identification of the Key Astringent Compounds in Spinach (Spinacia oleracea) by Means of the Taste Dilution Analysis. Chem. Percept. 1, 268–281 (2008). https://doi.org/10.1007/s12078-008-9028-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12078-008-9028-y