http://www.cnr.it/ontology/cnr/individuo/prodotto/ID176339
Differential reactivity of purified bioactive coffee furans, cafestol and kahweol, with acidic nitrite: product characterization and factors controlling nitrosation versus ring opening pathways (Articolo in rivista)
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- Differential reactivity of purified bioactive coffee furans, cafestol and kahweol, with acidic nitrite: product characterization and factors controlling nitrosation versus ring opening pathways (Articolo in rivista) (literal)
- Anno
- 2009-01-01T00:00:00+01:00 (literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
- 10.1021/tx900224x (literal)
- Alternative label
De Lucia, M.; Panzella, L.; Melck, D.; Giudicianni, I.; Motta, A.; Napolitano, A.; d'Ischia, M.; (2009)
Differential reactivity of purified bioactive coffee furans, cafestol and kahweol, with acidic nitrite: product characterization and factors controlling nitrosation versus ring opening pathways
in Chemical research in toxicology
(literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
- De Lucia, M.; Panzella, L.; Melck, D.; Giudicianni, I.; Motta, A.; Napolitano, A.; d'Ischia, M.; (literal)
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- ISI Web of Science (WOS) (literal)
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- Maria De Lucia+, Lucia Panzella+, Dominique Melck?, Italo Giudicianni§, Andrea Motta?, Alessandra Napolitano+, and Marco d'Ischia+,
+Department of Organic Chemistry and Biochemistry and §Centro Interdipartimentale di Metodologie Chimico-Fisiche (CIMCF), University of Naples \"Federico II\", Via Cinthia 4, I-80126 Naples, Italy;
?Istituto di Chimica Biomolecolare del CNR, Comprensorio OliVetti, Edificio A, Via Campi Flegrei 34, I-80078 Pozzuoli Naples, Italy (literal)
- Titolo
- Differential reactivity of purified bioactive coffee furans, cafestol and kahweol, with acidic nitrite: product characterization and factors controlling nitrosation versus ring opening pathways (literal)
- Abstract
- Cafestol and kahweol, coffee-specific furan diterpenes, are believed to cause various physiological
effects in human subjects, including an increase in cholesterol and plasma triacylglycerol levels as well
as cancer chemopreventive effects. Despite the increasing interest in these compounds raised by the
diverse range of biological activities, their reaction behavior and degradation pathways under physiologically
relevant conditions remain uncharted. Herein, we report a detailed investigation of the structural
modifications suffered by cafestol and kahweol in the presence of acidic nitrite under conditions mimicking
those occurring in the stomach during digestion as well as by action of other oxidants. Prior to the chemical
study, an isolation procedure for kahweol from green coffee beans was developed based on Soxhlet
extraction followed by preparative HPLC. Preliminary experiments showed that kahweol is much more
reactive than cafestol toward nitrite at pH 3, as evidenced by inhibition experiments with the
2,3-diaminonaphthalene assay as well as by product analysis in coffee extracts. When exposed to equimolar
nitrite in phosphate buffer, pH 3, kahweol gave as a main product the ring-opened dicarbonyl derivative
1. Under more forcing conditions, cafestol reacted as well to give a main nitrogenous product identified
as the 1-hydroxy-2-pyrrolinone 2. It is concluded that the conjugated double bond in kahweol is a critical
structural element, increasing the susceptibility of the furan ring to protonation rather than nitrosation
and favoring ring-opening routes driven by the irreversible oxidation steps. These results offer a useful
background to assess the effects of coffee-specific lipids in association with abnormally high nitrite levels
from the diet. (literal)
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