alexa Natural deuterium distribution in branched-chain medium-length fatty acids is nonstatistical: a site-specific study by quantitative 2H NMR spectroscopy of the fatty acids of capsaicinoids.
Pharmaceutical Sciences

Pharmaceutical Sciences

Journal of Bioequivalence & Bioavailability

Author(s): Markai S, Marchand PA, Mabon F, Baguet E, Billault I,

Abstract Share this page

Abstract Quantitative 2H NMR spectroscopy has been used to determine the natural abundance site-specific 2H isotopic content of 6,7-dihydrocapsaicin (1) and capsaicin (2). Prior to analysis, the fatty acyl moieties were released as methyl 8-methylnonanoate (3) and methyl E-8-methylnon-6-enoate (4), respectively. A marked and similar nonstatistical isotopic distribution of (2)H is observed for both fatty acids. Notably, it can be seen that: 1) the isobutyl portion of 3 is more impoverished in 2H than the methylenic portion; 2) the isobutyl portion of 4 is more impoverished than that of 3; 3) an alternating pattern occurs in the (2H/1H)i between the C3 to C7 positions; and 4) the ethylenic hydrogens at C6 and C7 of 4 are, respectively, impoverished and unchanged relative to these positions in 3. These observations are compatible with the proposed biosynthetic origins of the different parts of 1 and 2, and with the view that 1 is a proximal precursor of 2. Furthermore, it can be suggested that, firstly, the hydrogen atoms at C3 to C7 originate alternatively from the substrate and from the environment and, secondly, that the Delta6-E desaturation is introduced by a mechanism closely mimicking that of the Z desaturation of higher plants.
This article was published in Chembiochem and referenced in Journal of Bioequivalence & Bioavailability

Relevant Expert PPTs

Relevant Speaker PPTs

Recommended Conferences

Relevant Topics

Peer Reviewed Journals
 
Make the best use of Scientific Research and information from our 700 + peer reviewed, Open Access Journals
International Conferences 2017-18
 
Meet Inspiring Speakers and Experts at our 3000+ Global Annual Meetings

Contact Us

 
© 2008-2017 OMICS International - Open Access Publisher. Best viewed in Mozilla Firefox | Google Chrome | Above IE 7.0 version
adwords