Document Detail


Isolation and structural elucidation of some procyanidins from apple by low-temperature nuclear magnetic resonance.
MedLine Citation:
PMID:  12797747     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Procyanidin fractions from apple were separated according to the degree of polymerization using normal phase chromatography. Evaluation of physiological functionalities of procyanidins requires individual structural determination. However, it is difficult to elucidate the structure of procyanidins, in particular those with (+)-epicatechin (1) or (-)-catechin (2) units, and determine whether the interflavanoid bonds are 4beta-->8 or 4beta-->6 without cleavage and acetylation. Structural determination used LC-MS and low-temperature NMR. Nine procyanidins were separated by preparative HPLC consisting of three well-known procyanidins [procyanidin B1 (3), procyanidin B2 (4), and procyanidin C1 (5)] and six new procyanidins [epicatechin-(4beta-->8)-epicatechin-(4beta-->8)-catechin (6); epicatechin-(4beta-->6)-epicatechin-(4beta-->8)-catechin (7); epicatechin-(4beta-->6)-epicatechin-(4beta-->8)-epicatechin (8); epicatechin-(4beta-->8)-epicatechin-(4beta-->6)-catechin (9); epicatechin-(4beta-->8)-epicatechin-(4beta-->6)-epicatechin (10); and epicatechin-(4beta-->8)-epicatechin-(4beta-->8)-epicatechin-(4beta-->8)-epicatechin (11)]. Compounds 6-11 were detected for the first time as apple constituents.
Authors:
Toshihiko Shoji; Motoh Mutsuga; Takatoshi Nakamura; Tomomasa Kanda; Hiroshi Akiyama; Yukihiro Goda
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of agricultural and food chemistry     Volume:  51     ISSN:  0021-8561     ISO Abbreviation:  J. Agric. Food Chem.     Publication Date:  2003 Jun 
Date Detail:
Created Date:  2003-06-11     Completed Date:  2003-07-25     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0374755     Medline TA:  J Agric Food Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  3806-13     Citation Subset:  IM    
Affiliation:
Fundamental Research Laboratory, Asahi Breweries, Ltd., 1-21 Midori 1-chome, Moriya, Ibaraki 302-0106, Japan. toshihiko.shoji@asahibeer.co.jp
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MeSH Terms
Descriptor/Qualifier:
Biflavonoids*
Catechin / chemistry*,  isolation & purification*
Chromatography, High Pressure Liquid
Fruit / chemistry*
Magnetic Resonance Spectroscopy / methods*
Malus / chemistry*
Proanthocyanidins*
Spectrometry, Mass, Electrospray Ionization
Temperature
Chemical
Reg. No./Substance:
0/Biflavonoids; 0/Proanthocyanidins; 154-23-4/Catechin; 20315-25-7/procyanidin B1; 29106-49-8/procyanidin B2; 4852-22-6/procyanidin

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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