Stable Isotope Labeling Pattern of Resveratrol and Related Natural Stilbenes
| Autor: | Marco Cisero, Claudio Fuganti, Giovanni Fronza, Joseph Koziet, Stefano Serra |
|---|---|
| Rok vydání: | 2002 |
| Předmět: |
Magnetic Resonance Spectroscopy
Molecular Structure biology Stereochemistry Stable isotope ratio Chemical structure General Chemistry Resveratrol Deuterium biology.organism_classification Polygonaceae chemistry.chemical_compound Metabolic pathway Hydrolysis Biosynthesis chemistry Glucoside Isotope Labeling Stilbenes General Agricultural and Biological Sciences |
| Zdroj: | Journal of agricultural and food chemistry 50 (2002): 2748–2754. doi:10.1021/jf011103j info:cnr-pdr/source/autori:Fronza G., Fuganti C., Serra S., Cisero M., Koziet J./titolo:Stable isotope labeling pattern of resveratrol and related natural stilbenes/doi:10.1021%2Fjf011103j/rivista:Journal of agricultural and food chemistry/anno:2002/pagina_da:2748/pagina_a:2754/intervallo_pagine:2748–2754/volume:50 |
| ISSN: | 1520-5118 0021-8561 |
| DOI: | 10.1021/jf011103j |
| Popis: | The stable isotope characterization of resveratrol 1 from Polygonum cuspidatum and of related natural stilbenes 11 and 12 obtained by hydrolysis of the corresponding glucosides 2 and 3 from Rheum is reported. The C-6-C-2-C-6 framework of suitably protected derivatives of 1, 2, and 3 has been degraded with ozone to the C-6-C-1 aldehydes 4, 5, 9, and 10, retaining all hydrogen atoms of the precursors. The natural and synthetic derivatives are characterized and distinguished by natural abundance deuterium nuclear magnetic resonance studies. In the case of anisaldehyde 4 the two series show, as expected, the characteristic difference of the aromatic labeling. The formyl deuterium contents of 4 and 5 from resveratrol are remarkably different, seemingly reflecting the different enrichments existing between positions 3 and 2, respectively, of the phenylpropanoid precursor. The positional delta(18)O values of the extractive materials 1-3 were also determined. In this instance a selective deoxygenation procedure was adopted, leading from 1 to the products 6, 7, and 8. The delta(18)O values of the latter compounds reveal, respectively, those at position 4' and positions 3 and 5 of 1. Similarly, the phenolic products 11 and 12 were converted into 13 and 14. From the delta(18)O values of the single components it is possible to design a detailed map of the oxygen fractionations which characterizes the stilbenes 1-3. In particular, the oxygen present at position 4' of the phenylpropanoid moiety of 1-3 shows delta(18)O values of +11.5, +1.8, and +6.7parts per thousand, respectively. Moreover, the phenolic oxygen atom at position 3' of rhapontin 3 shows a value of +11.7parts per thousand. The data are compared with those previously obtained on structurally related compounds. These results show the utility of simple chemical degradations in the stable isotope characterization of structurally complex food components. |
| Databáze: | OpenAIRE |
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