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Isolation and structural elucidation of some procyanidins from apple by low-temperature nuclear magnetic resonance.
J Agric Food Chem. 2003 Jun 18; 51(13):3806-13.JA

Abstract

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+Show Affiliations

Fundamental Research Laboratory, Asahi Breweries, Ltd., 1-21 Midori 1-chome, Moriya, Ibaraki 302-0106, Japan. toshihiko.shoji@asahibeer.co.jpNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

12797747

Citation

Shoji, Toshihiko, et al. "Isolation and Structural Elucidation of some Procyanidins From Apple By Low-temperature Nuclear Magnetic Resonance." Journal of Agricultural and Food Chemistry, vol. 51, no. 13, 2003, pp. 3806-13.
Shoji T, Mutsuga M, Nakamura T, et al. Isolation and structural elucidation of some procyanidins from apple by low-temperature nuclear magnetic resonance. J Agric Food Chem. 2003;51(13):3806-13.
Shoji, T., Mutsuga, M., Nakamura, T., Kanda, T., Akiyama, H., & Goda, Y. (2003). Isolation and structural elucidation of some procyanidins from apple by low-temperature nuclear magnetic resonance. Journal of Agricultural and Food Chemistry, 51(13), 3806-13.
Shoji T, et al. Isolation and Structural Elucidation of some Procyanidins From Apple By Low-temperature Nuclear Magnetic Resonance. J Agric Food Chem. 2003 Jun 18;51(13):3806-13. PubMed PMID: 12797747.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Isolation and structural elucidation of some procyanidins from apple by low-temperature nuclear magnetic resonance. AU - Shoji,Toshihiko, AU - Mutsuga,Motoh, AU - Nakamura,Takatoshi, AU - Kanda,Tomomasa, AU - Akiyama,Hiroshi, AU - Goda,Yukihiro, PY - 2003/6/12/pubmed PY - 2003/7/26/medline PY - 2003/6/12/entrez SP - 3806 EP - 13 JF - Journal of agricultural and food chemistry JO - J. Agric. Food Chem. VL - 51 IS - 13 N2 - 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. SN - 0021-8561 UR - https://www.unboundmedicine.com/medline/citation/12797747/Isolation_and_structural_elucidation_of_some_procyanidins_from_apple_by_low_temperature_nuclear_magnetic_resonance_ L2 - https://dx.doi.org/10.1021/jf0300184 DB - PRIME DP - Unbound Medicine ER -