Stable isotope characterization of the ortho-oxygenated phenylpropanoids: Coumarin and melilotol

Journal of Agricultural and Food Chemistry

Volumn 53, Issue 24, 2005, Pages 9383-9388

  Brenna, Elisabetta ^a   Fronza, Giovanni ^b   Fuganti, Claudio ^a   Gatti, Francesco G ^a   Grande, Valentina ^a   Serra, Stefano ^b   Guillou, Claude ^c   Reniero, Fabiano ^c   Serra, Francesca ^c  

^a POLITECNICO DI MILANO   (Italy)

^b CNR   (Italy)

^c JOINT RESEARCH CENTRE   (Italy)

Author keywords

Chroman; Coumarin; Deuterium NMR; Dihydrocoumarin; Extractive; Methyl cinnamate; Positional 18o values; Synthetic

Indexed keywords

COUMARIN; COUMARIN DERIVATIVE; DEUTERIUM; MELILOTOL;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION;

COUMARINS; DEUTERIUM; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

SACCHAROMYCES CEREVISIAE;

EID: 28944432554     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0518507     Document Type: Article

References (19)

1. 2H patterns in natural compounds and its importance fort he elucidation of biosynthetic pathways. Phytochem. Rev. 2003, 2, 61-85.
2. 18O Pattern and biosynthesis of natural plant products. Phytochemistry 2001, 58, 9-32.
3. Martin, G. J.; Martin, M. L. Stable isotope analysis of food and beverages by NMR spectroscopy. Annu. Rep. NMR Spectrosc. 1995, 31, 91-104.
4. Remaud, G. S.; Martin, Y. L.; Martin, G. G.; Martin, G. J. Detection of sophisticated adulterations of natural vanilla flavors and extracts: Application of the SNIF-NMR method to vanillin and p-hydroxybenzaldehyde. J. Agric. Food Chem. 1997, 45, 859-866.
5. 18O) values of extracted and synthetic vanillin. Helv. Chim. Acta 2001, 84, 351-358.
6. Fronza, G.; Fuganti, C.; Pedrocchi-Fantoni, G.; Serra, S.; Zucchi, G.; Fauhl, C.; Guillou, C.; Reniero, F. Stable isotope characterization of raspberry ketone extracted from Taxus baccata and obtained by oxidation of the accompanying alcohol (betuligenol). J. Agric. Food Chem. 1999, 47, 1150-1155.
7. Fronza, G.; Fuganti, C.; Serra, S.; Cisero, M.; Koziet, J. Stable isotope labeling of resveratrol and related natural stilbenes. J. Agric. Food Chem. 2002, 50, 2748-2754.
8. Haslam, E. Shikimic Acid. Metabolism and Metabolites; Wiley: Chicester, United Kingdom, 1993.
9. 2H nuclear magnetic resonance. J. Agric. Food Chem. 2003, 51, 4866-4872.
10. 18 O-value of the p-OH group of L-tyrosine permits the assignment of its origin to plant or animal sources. Eur. Food Res. Technol. 2002, 215, 55-58.
11. 2H aromatic pattern of natural 2-hydroxybenzyl alcohol. J. Agric. Food Chem. 2004, 52, 7747-7751.
12. Bauer, K.; Garbe, D.; Surburg, H. Common Fragrance and Flavor Materials; Wiley-VCH: Weinheim, Germany, 2001; p 221.
13. Bleitreu, H. Untersuchungen über Cumarin. Liebig's Ann. 1846, 59, 177-198.
14. Phipson, T. L. Über das melilotol. Chemisches Central-Blatt. 1875, 646.
15. Perkin, W. H. Bildung von Cumarin und zimmtsäure, und anderen analogen säure aus aromatischen aldehyden. Ber. 1877, 10, 299-300.
16. 2H-ERETIC NMR authentication of the origin of methyl salicylate. J. Agric. Food. Chem. 2005, 53, 5125-5129.
17. Walsh, C. Enzymic Reactions Mechanism; Freeman: San Francisco, CA, 1979; pp 923-929.
18. Sedgwick, B.; Morris, C. Stereohemical course of hydrogen transfer catalysed by enoyl reductase enzymes of the yeast fatty acid synthetase. J. Chem. Soc., Chem. Commun. 1980, 96-97.
19. 2H nuclear magnetic resonance study of the origin of raspberry ketone. J. Agric. Food Chem. 1998, 46, 248-256.