Epicatechin B-ring conjugates: first enantioselective synthesis and evidence for their occurrence in human biological fluids.
Herein, the first enantioselective total synthesis of a number of biologically relevant (-)-epicatechin conjugates is described. The success of this synthesis relied on (i) optimized conditions for the stereospecific cyclization step leading to the catechin C ring; on (ii) efficient conjugation reactions; and on (iii) optimized deprotection sequences. These standard compounds have been subsequently used to elucidate for the first time the pattern of (-)-epicatechin conjugates present in four different human biological fluids following (-)-epicatechin absorption.
Nestle Research Center, P.O. Box 44, CH-1000 Lausanne 26, Switzerland.
Fedor
F
Romanov-Michailidis
Florian
F
Viton
René
R
Fumeaux
Antoine
A
Lévèques
Lucas
L
Actis-Goretta
Maarit
M
Rein
Gary
G
Williamson
Denis
D
Barron
D001826:Body Fluids / Q000737:chemistry*; D002392:Catechin / Q000031:analogs & derivatives* / Q000032:analysis / Q000097:blood / Q000138:chemical synthesis* / Q000652:urine; D003500:Cyclization; D006801:Humans; D015394:Molecular Structure; D013237:Stereoisomerism
D002392:Catechin