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2006 | 05 | 1 |

Tytuł artykułu

Chirality and the nature of food authenticity of aroma

Warianty tytułu

PL
Chiralność a natura żywności autentyczność zapachu

Języki publikacji

EN

Abstrakty

EN
The phenomenon of chirality, common in nature, pertains also to food components. The effect of the chiral structure of chemical compounds is the occurrence of optical isomers, i.e. enantiomers. The only source of optically active substances are living organisms, which produce most frequently mostly one of isomers. Proteins and carbohydrates are chiral: amino acids are found in proteins only in the L form, whereas carbohydrates are formed of D-saccharides. Enantiomers may exhibit diverse behaviour in reactions with biologically active compounds of living organisms. Chiral structure of proteins turned out to be significant in the perception of taste perceptions as well as the perception of aroma. The most characteristic phenomenon is chirality among odorants. Numerous compounds essential for aroma are found in nature in the form of two isomers, with considerable predominance of one of them, while the ratio of these isomers is specific and stable. Enantiomers of odorants may differ in the intensity and character of their smell. The phenomenon of chirality has been known since mid-1800; however, it then constituted a serious analytical problem. Only the development of methods facilitating the separation of optical isomers created a possibility to investigate its universality and importance in living organisms. The application of more and more advanced analytical techniques in the control of chiral nature of food ingredients may be used to detect adulterations and especially to determine authenticity of fragrances.
PL
Zjawisko chiralności, które jest powszechne w przyrodzie, dotyczy także składników żywności. Wynikiem chiralnej struktury związków chemicznych jest występowanie izomerów optycznych, czyli enancjomerów. Źródłem optycznie czynnych substancji są wyłącznie organizmy żywe, które wytwarzają najczęściej w znacznej przewadze jeden z izomerów. Chiralne są białka i węglowodany: aminokwasy występują w białkach tylko w formie L, podczas gdy węglowodany zbudowane są z D-sacharydów. Enancjomery mogą wykazywać zróżnicowane zachowanie w reakcjach z biologicznie aktywnymi związkami organizmów żywych. Chiralna struktura białek okazała się istotna zarówno w odbiorze wrażeń smakowych, jak i w percepcji zapachu. Najbardziej charakterystyczne jest zjawisko chiralności wśród związków zapachowych. Wiele istotnych dla aromatu związków występuje w naturze w formie dwóch izomerów, ze znaczną przewagą jednego z nich, przy czym stosunek tych izomerów jest specyficzny i stały. Enancjomery związków zapachowych mogą różnić się intensywnością i charakterem zapachu. Zjawisko chiralności było znane od połowy XIX wieku, stanowiło jednak poważny problem analityczny. Dopiero rozwój metod pozwalających na rozdział izomerów optycznych stworzył możliwość poznania jego powszechności i znaczenia w organizmach żywych. Wykorzystanie coraz bardziej udoskonalonych technik analitycznych w kontroli chiralnej natury składników żywności może służyć do wykrywania zafałszować, a w szczególności do ustalania autentyczności aromatów.

Wydawca

-

Rocznik

Tom

05

Numer

1

Opis fizyczny

p.21-36,ref.

Twórcy

  • Agricultural University of Poznan, Wojska Polskiego 31, 60-624 Poznan, Poland

Bibliografia

  • Adams A., Demyttenaere C.R., De Kimpe N., 2003. Biotransformation of (R)-(+) and (S)-(-)- -limonene to a-terpineol by Penicillium digitatum - investigation on the culture condition. Food Chem. 80, 525-534.
  • Askari C., Kreis P., Mosandl A., Schmarr H.G., 1992. Chiral compounds of essential oils. VII. Quality evaluation of Mentha oils using enantioselective CGC analysis of monoterpenoids constituents. Arch. Pharm. 325, 35-39.
  • Assaf S., Hadar Y., Dosoretz C.G., 1997. l-octen-3-ol and 13-hydroperoxylinoleate are products of distinct pathways in the oxydative breakdown of linoleic acid by Pleurotus pulmonarius. Enzyme Microbial Technol. 21, 484-490.
  • Bauer R.G., Garbe D., Surburg H., 1990. Common fragrance and flavour materials. VCH Ver- lagsgesellschaft Wienheim, Germany.
  • Belitz H.D., Grosch W., 1999. Food chemistry. Springer Berlin.
  • Bemreuther A., Epperlein U., Koppenhoefer B., 1997. Enantiomers: Why they are important and how to resolve them. In: Techniques for analyzing food aroma. Ed. R. Marsili. Marcel Dekker New York, 143-207.
  • Bicchi C., Cordero Ch., Iori C., Rubiolo P., 2000 a. Headspace sorptive extraction (HSSE) in the headspace analysis of aromatic and medicinal plants. J. High Resol. Chromatogr. 23 (9), 539- -546.
  • Bicchi C., Drigo S., Rubiolo P., 2000 b. Influence of fibre coating in headspace solid-phase microextraction-gas chromatographic analysis of aromatic medicinal plants. J. Chromatogr. A, 892, 469-485.
  • Blank L., Grosch W., 1991. Evaluation of potent odorants in dill seed and dill herb (Anethum graveolens L.) by aroma extract dilution analysis. J. Food Sci. 56, 63-67.
  • Bouwmeester H.J., Davis Toxopeus H., 1995. Enantiomeric composition of carvone, limonene and carveols in seeds of dill and annual and biennial caraway varieties. J. Agric. Food Chem. 43, 3057-3064.
  • Brenna E., Fuganti C., Serra S., 2003. Enantioselective perception of chiral odorants. Tetrahedron: Asymmetry 14, 1-42.
  • Chambers IV.E., Smith E.C., Seitz L.M., Sauer D.B., 1998. Sensory properties of musty compounds in food. In: Food flavors: formation analysis and packaging influences. Eds E.T. Contis, C.T. Ho, C.J. Mussinan, T.H. Parliment, F. Shahidi, A.M. Spanier. Elsevier Amsterdam, 173-180.
  • Chen C.C., Chen S.D., Chen J.J., Wu C.M., 1984. Effects of pH value on the formation of volatiles of shiitake (Lentinum edodes) and edible mushroom. J. Agric. Food Chem. 32, 999-1001.
  • Chen C.C., Wu C.M., 1984. Studies on the enzyme reduction of l-octen-3-ol in mushrooms (Aga- ricus bisporus). J. Agric. Food Chem. 32, 1342-1344.
  • Cruz C., Noel-Suberville C., Montury M., 1997. Fatty acids content and some flavor compounds release in two strains of Agaricus bisporus, according to three stages of development. J. Agric. Food Chem. 45, 64-67.
  • Cuvelier M.E., Richard H., Berset C., 1966. Antioxidative activity and phenolic composition of pilot-plant and commercial extracts of sage and rosemary. JAOCS 5, 645-652.
  • Délateur P., Benoit E., Besse S., Soraci A., 1994. Asymetrie moléculaire et pharmacologie comparée. Revue Mèd. Vêt. 145 (7), 551-561.
  • Diaz P., Senorans F.J., Reglero G., Ibanez E., 2002. Trufle aroma analysis by headspace solid phase microextraction. J. Agric. Food Chem. 50, 6468-6472.
  • Dugeloy L., Gunata Z., Bitter S., Sapis J.C., Bammes R., Bayonove C., 1993. Formation of volatile phenols from cinnamic precursors during wine - making: the role of cynnamoyl esterase from commercial enzymic products. In: Progress in flavour precursor studies. Eds P. Schreier, P. Winterhalter. Allured Publishing Corporation USA, 361-378.
  • Engel K.H., Albrecht W., Tressl R., 1995. Chirality and aroma compounds: Bioformation and evaluation. In: Aroma perception formation evaluation. Proceedings of the 4th Wartburg Aroma Symposium, 1994. Eds M. Rothe, H.P. Kruse. Deutsches Institut fur Emâhrungsforschung, Potsdam-Rehbriicke, 229-246.
  • Emberger R., 1981. Aspects of the development of industrial flavor materials. In: Flavour’s Proceedings of the International Conference, 3rd Weurman Symposium, 1981. Ed. P. Schreier. Walter de Griiyter, Berlin, 619-634.
  • Faber B., Bangert K., Mosandl A., 1997. GC-IRMS and enantioselective analysis in biochemical studies in dill (Anethum graveolens L.). Flavour Fragrance J. 12, 305-304.
  • Faber B., Ditrich A., Mosandl A., 1994. Chiral compounds of essential oils. XV. Stereodifferentiation of characteristic compounds of Mentha species by multidimentional gas chromatography. J. Chromatogr. 666, 161-165.
  • Fischer K.H., Grosch W., 1987. Volatile compounds of importance in the aroma of mushrooms (Psalliota bispora). Lebensm. Wiss. u.- Technol. 20, 233-236.
  • Flamini G., Cioni P., Morelli L., 2002. Main-agronomic-productive characteristics of two ecotypes of Rosmarinus officinalis L. and chemical composition of their essential oils. J. Agric. Food Chem. 50,3512-3517.
  • Gandolfi I., Palla G., Delprato F., De Nisco F., Marchelli R., Salovadori C., 1992. D-amino acids in milk as related to heat treatments and bacterial activity. J. Food Sci. 57, 377-379.
  • Gandolfi I., Palla G., Marchelli R., Dossena A., Puelli S., Salovadori C., 1994. D-alanine in fruit juices: A molecular marker of bacterial activity, heat treatments and shelf-life. J. Food Sci. 59, 152-154.
  • Góra J., 1998. Trendy w produkcji i stosowaniu aromatów spożywczych [Trends in production and application of food frangrancesj. Przem. Spoż. 9, 25-30.
  • Grosch W., 1993. Detection of potent odorants in foods by aroma dilution analysis. Trends Food Sci. Technol. 4, 68-73.
  • Güntert M., Bertram H.J., Emberger R., Hopp R., Sommer H., Werkhoff P., 1992. New aspects of the thermal generation of flavour compounds from thiamine. In: Progress in flavour precursors studies. Eds P. Schreier, P. Winterhalter. Allured Publishing Corporation USA, 361-378.
  • Haelval S., Craker L.E., Simon J.E., Charles O.J., 1993. Growth and essential oil in dill Anethum graveolens L. in response to temperature and photoperiod. J. Herbs Spec. Med. Plants 3,47-56.
  • Haffher T., Garbe L.A., Lange H., Tressl R., 1997. Biosynthesis of enantiomeric aroma compounds. In: Flavour perception - aroma evaluation. Proceedings of the 5th Wartburg Aroma Symposium, Eisenach, 1997. Eds M. Rothe, H.P. Kruse. Universität Potsdam.
  • Hormann C.A., Cowart B. J., 1993. Olfactory discrimination of carvone enantiomers. Chem. Senses 18, 573.
  • Huopalahti R., 1986. Gas chromatographic and sensory analyses in the evaluation of the aroma of dill herb, Anethum graveolens L. Lebensm. Wiss. u.- Technol. 19, 27-30.
  • Jaroniewski W., 1994. Rozmaryn lekarski - roślina lecznicza i użytkowa [Rosemary - a medicinal and cultivated plant]. Wiad. Ziel. 36, 3, 6.
  • Juchelka D., Beck T., Hener U., Dettmar F., Mosandl A., 1998. Multidimensional gas chromatography coupled on-line with isotope ratio mass spectrometry (MDGC - IRMS): Progress in the analytical authentication of genuine flavor components. J. High Resol. Chromatogr. 21 (3), 145-151.
  • Juchelka D., Mosandl A., 1996. Authenticity profiles of bergamot oil. Pharmazie 51,417-422.
  • Juchelka D., Steil A., Witt K., Mosandl A., 1996. Chiral compounds of essential oils. XX. Chirality evaluation and authenticity profiles of neroli and petitgrain oils. J. Essent. Oil. Res. 8, 487-497.
  • Kaloustian J., Portugal H., Pauli A.M., Pastor J., 2002. Chemical, chromatographic and thermal analysis of rosemary (Rosmarinus Officinalis L.). J. Appl. Polymer Sei. 8, 747-756.
  • Kaunzinger A., Juchelka D., Mosandl A., 1997. Progress in the authenticity assessment of vanilla. 1. Initiation of authenticity profiles. J. Agric. Food Chem. 45, 1752-1757.
  • Kobayashi A., Winterhalter P., Morita K., Kubota K., 1993. Glycosides in fresh tea leaves precursors of black tea. In: Progress in flavour precursors studies. Eds P. Schreier, P. Winterhalter. Allured Publishing Corporation USA, 257-261.
  • Kokkini S., Karousou R., Lanaras T., 1995. Essential oils of spearmint (carvone-rich) plants from the island of Crete (Greece). Biochem. Syst. Ecol. 23 (4), 425-430.
  • Korczak J., Janitz W., Hęś M., Nogala-Kalucka., Gogolewski M., 1999. Stabilizacja oleju rzepakowego przy wykorzystaniu naturalnych przeciwutleniaczy [Stabilization of rape oil using natural antioxidants]. Rośl. Oleiste 20, 2, 569-579 [in Polish].
  • König W.A., Icheln D., Runga T., Pforr I., Krebs A., 1990. Cyclodextrins as chiral stationary phases in capillary gas chromatography. Part VII. J. High Resolution Chromatogr. 13, 702-707.
  • Kreis P., Mosandl A., 1992. Chiral compounds of essential oils. Part XII. Authenticity control of rose oils using enantioselective multidimentional gas chromatography. Flavour Fragrance J. 7, 199-203.
  • Laska M., Teubner P., 1999. Olfactory discrimination ability of human subjects for ten pairs of enantiomers. Chem. Senses 24, 161-170.
  • Lawrence B.M., 1996. Progress in essential oils. Perfumer Flavorist 21,55-68.
  • Leitereg T.J., Guadagni D.G., Harris J., Mon T.R., Teranishi R., 1971. Chemical and sensory data supporting the difference between the odors of the enantiomeric carvones. J. Agric. Food Chem. 19, 785-787.
  • Lizärraga-Guerra R., Guth H., Lopez M.G., 1997. Identification of the most potent odorants in huitlacoche (Ustilago maydis) and austem pilzen (Pleurotus sp.) by aroma extract dilution analysis and static head-space samples. J. Agric. Food Chem. 45, 1329-1332.
  • Maier N.M., Franco P., Lindner W., 2001. Separation of enantiomers: needs, challenges, perspectives. J. Chromatogr. A 906, 3-33.
  • Maga J.A., 1981. Mushroom flavor. J. Agric. Food Chem. 29, 1-4.
  • Marchelli R., Dossena A., Palla G., 1996. The potential of enantioselective analysis as a quality control tool. Trends Food Sei. Technol. 7 (4), 113-119.
  • Mau J.L., Beelman R.B., Ziegler G.R., 1992. l-octen-3-ol in the cultivated mushroom Agaricus bisporus. J. Food Sci. 57 (3), 704-706.
  • Mau J.L., Chyau C.C., Li J.Y., Tseng Y.H., 1997. Flavor compounds in straw mushrooms Vol- variella volvacea harvested at different stages of maturity. J. Agric. Food Chem. 45 (12), 4746-4729.
  • McLaughlin S., Margolskee R.F., 1994. The sense of taste. Am. Sci. 82, 538-545.
  • Mor J.R., 1992. Biotechnology in the flavour industry. In: Aroma production and application. Proceedings of the 3rd Wartburg Aroma Symposium, Eisenach, 1991. Eds M. Rothe, H.P. Kruse. Deutsches Institut fur Emahrungsforschung. Potsdam Rehbriicke, 17-28.
  • Morrison R.T., Boyd R.N., 1996. Chemia organiczna [Organic chemistry], PWN Warszawa [in Polish],
  • Mosandl A., 1995. Enantioselective capillary gas chromatography and stable isotope ratio mass spectrometry in the authenticity control of flavors and essential oils. Food Rev. Int. 11, 597-664.
  • Mosandl A., Heusinger G., Gessner M., 1986. Analytical and sensory differentiation of l-octen-3- ol enantiomers. J. Agric. Food Chem. 34, 119-122.
  • Mosandl A., Juchelka D., 1997. Advances in the authenticity assessment of citrus oils. J. Essent. Oil Res. 9, 5-12.
  • Mosandl A., Kreis P., 1992. Chiral compounds of essential oils. Part XI. Simultaneous stereoanalysis of lawandula oil constituents. Flavour Fragrance J. 7, 187-193.
  • Nakatani N., Inatani R., 1984. Two antioxidative diterpens from rosemary and revised structure for rosmanol. Agric. Biol. Chem. 48, 2081-2084.
  • Ochocka J.R., Asztemborska M., Zook D.R., Sybilska D., Perez G., Ossicini L., 1997. Enantiomers of monoterpenic hydrocarbons in essential oils from Juniperus communis. Phytochemistry 5, 869-873.
  • Oliver J.E., 2003. (S)(+)-Linalool from oil of coriander. J. Essent. Oil Res. 15, 31-33.
  • Oosterhaven K., Hartmans K.J., Scheffer J.J.C., 1995. Inhibition of potato sprout growth by car- vone enantiomers and their bioconversion in sprouts. Potato Res. 38, 219-230.
  • Oosterhaven K., Leitao A.Ch., Gorris L.G.M., Snid E.J., 1996. Comparative study on the action of (S)-(+)-carvone, in situ, on the potato storage fungi Fusarium solani var. Coeruleum and Fusarium suplhureum. J. Appl. Bacteriol. 80, 535-539.
  • Pino J.A., Rosado A., Goire L, Roncal E., 1995. Evaluation of flavour characteristic compounds in dill herb essential oil by sensory analysis and gas chromatography. J. Agric. Food Chem. 43, 1307-1309.
  • Prescott J., Bell G., 1995. Cross-cultural determinants of food acceptability: Recent research on sensory perceptions and preferences. Trends Food Sci. Technol. 6, 201-205.
  • Rawid U., Putiewsky E., Katzir L, 1992. Chiral GC analysis of (S) (+) and (R) (-)- carvone with high enantiomeric purity in caraway, dill and spearmint oils. Flavour Fragrance J. 7, 289-292.
  • Reichert S., Wiist M., Beck T., Mosandl A., 1998. Stereoisomeric flavor compounds LXX XI. Dill ether and its cis-stereoisomers: synthesis and enantioselective analysis. J. High Resol. Chromatogr. 21 (3), 185-188.
  • Reichert S., Mosandl A., 1999. Stereoisomeric flavor compounds LXXXII. Dill ether and its stereoisomers: synthesis and enantioselective analysis. J. High Resol. Chromatogr. 22 (11), 631-634.
  • Rouhi A.M., 2003. Chiral business. Chem. Eng. News 5, 45-55.
  • Russell G.F., Hills J.I., 1971. Odor differences between enantiomeric isomers. Sci. 4, 1043-1044.
  • Rutkowski A., Gwiazda S., Dąbrowski K., Czapski J., Kamiński E., Pluta A., 1997. Substancje dodatkowe i składniki funkcjonalne żywności [Food additives and functional components]. Agro Food Technol. Czeladź [in Polish],
  • Sadof C.S., Grant G.G., 1997. Monoterpene composition of Pinus sylvestris varieties resistant and susceptible to Dioryctia zimmermani. J. Chem. Ecol. 23 (8), 1917-1927.
  • Salido S., Altarejos J., Nogueras M., Sanchez A., Lugue P., 2003. Chemical composition and seasonal variations of rosemary oil from southern Spain. J. Essent. Oil Res. 15, 10-14.
  • Schiffman, S.S., Pearce, T.C., 2003. Introduction to Olfaction: Perception, Anatomy, Physiology and Molecular Biology. In: Handbook of Machine Olfaction. Ed. T.C. Pierce, S.S. Schiffman, H.T. Nagle, J.W. Gardner. Willey-Wch Weinheim.
  • Schreier P., Appel M., Hartlieb A., Elss S., Heckel F., Hor K., Richling E., Ruff C., Weckerle B., 2003. Gas chromatography isotope ratio mass spectrometry (HRGC - IRMS). Proceedings of the 34th International Symposium on Essential Oils ISEO 2003, Wurzburg, Germany.
  • Schurig V., 2001. Separation of enantiomers by gas chromatography. J. Chromatogr. A 906, 275-299.
  • Seńorans F.J., Ibanez E., Cavero S., Tabera J., Reglero G., 2000. Liquid chromatographic-mass spectrometric analysis of supercritical-fluid extracts of rosemary plants. J. Chromatogr. A 870, 491-499.
  • Serrano E., Palma J., Tinoco T., Venancio F., Martins A., 2002. Evaluation of the essential oils of rosemary Rosmarinus officinalis L. from different zones of “Alentejo” (Portugal). J. Essent. Oil Res. 14, 87-92.
  • Siani A.C., Tappin M.R.R., Ramos M.F.S., Mazzei J.L., Ramos M.C.K.V., de Aquino Neto F. R., Frighetto N., 2002. Linalool from Lippia alba: Study of the reproducibility of the essential oil profile and the enantiomeric purity. J. Agric. Food Chem. 50, 3518-3521.
  • Singh A., Randhava G.S., Mahey R.K., 1987. Oil content and oil yield of dill {Anethum graveolens L.) herb under some agronomic practices. Acta Hortic. 208, 51-60.
  • Smith D.V., Margolskee R.F., 2001. Poznać zmysł smaku [To get to know the sense of taste]. Świat Nauki 5, 46-53 [in Polish],
  • Solomons T.W.G., Fryhle C.B., 2000. Organic chemistry. John Wiley New York.
  • Stelmaszczyk-Kusz A., Kozłowska K., Brzozowska A., 1998. Substancje aromatyczne do żywności - bezpieczeństwo stosowania i metody szacowania ich spożycia [Aromatic substances to be used in food - safety of application and methods to estimate their consumption]. Przem. Spoż. 4, 24-27 [in Polish].
  • Sugawara Y., Hara Chi., Aoki T., Sugimoto N., Masujima T., 2000. Odor distinctiveness between enantiomers of linalool: difference in perception and responses elicited by sensory test and forehead surface potential wave measurement. Chem. Senses 25, 77-84.
  • Venkateshwarlu G., Chandrawadana M.V., Tewari R.P., 1999. Volatile flavour components of some edible mushrooms (Basidiomycetes). Flavour Fragrance J. 14, 191-194.
  • Wawrzeńczyk Cz., 1997. Chemia organiczna. Właściwości chemiczne i spektroskopowe związków organicznych [Organie chemistry. Chemical and spectroscopic properties of organie compounds], Wyd. AR Wrocław [in Polish],
  • Wąsowicz E., 1974. Identification of the volatile flavor compounds in mushrooms, Agaricus bisporus. Bull. Acad. Pol. Sci. 22 (3), 143-151.
  • Weber B., Mass A., Mosandl A., 1995. Stereoisomeric distribution of some chiral sulfur containing trace components of yellow passion fruits. J. Agric. Food Chem. 43, 2438-2441.
  • Weber B., Mosandl A., 1997. Stereoisomeric flavour compounds LXXV: Synthesis and structure - function relationship of 3-methylothiobutanol enantiomers. Z. Lebensm. Unters. Forsch. A 204, 194-197.
  • Zawirska-Wojtasiak R., 2004 a. Charakterystyka składu enancjomerów w wybranych aromatach pochodzenia naturalnego i jej wykorzystanie w kontroli autentyczności tych aromatów [A characteristic of enantiomer composition in selected natural fragrances and its application in the authenticity control of these flavours]. Rocz. AR Pozn. Rozpr. Nauk. 352 [in Polish],
  • Zawirska-Wojtasiak R., 2004 b. Optical purity of (R)-(-)-octen-3-ol in the aroma of various species of edible mushrooms. Food Chem. 86, 113-118.
  • Zawirska-Wojtasiak R., Wąsowicz E., 2000. Enantiomeric composition of limonene and carvone in seeds of dill and caraway grown in Poland. Pol. J. Food Nutr. Sci. 3,9-13.
  • Zawirska-Wojtasiak R., Wąsowicz E., 2002. Estimation of the main dill seeds odorant carvone by solid-phase microextraction and gas chromatography. Nahrung, Food 46, 357-359.
  • Zawirska-Wojtasiak R., Wąsowicz E., Jeleń H., Rudzińska M., Kamiński E., Błażczak P., 1998. Aroma characteristics of dill seeds varieties grown in Poland. Pol. J. Food Nutr. Sci. 2, 181-191.

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