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Structural identification and distribution of proanthocyanidins in 13 different hops.
J Agric Food Chem. 2006 May 31; 54(11):4048-56.JA

Abstract

Ten newly isolated hop proanthocyanidin oligomers and flavan-3-ol monomers from 13 different hops have been identified as gallocatechin, gallocatechin-(4alpha-->8)-catechin, gallocatechin-(4alpha-->6)-catechin, catechin-(4alpha-->8)-gallocatechin, catechin-(4alpha-->6)-gallocatechin, afzelechin-(4alpha-->8)-catechin, catechin-(4alpha-->8)-catechin-(4alpha-->8)-catechin, epicatechin-(4beta-->8)-epicatechin-(4beta-->8)-catechin, catechin-(4alpha-->8)-gallocatechin-(4alpha-->8)-catechin, and gallocatechin-(4alpha-->8)-gallocatechin-(4alpha-->8)-catechin, together with seven previously isolated oligomers, namely, catechin, epicatechin, epicatechin-(4beta-->8)-catechin, epicatechin-(4beta-->8)-epicatechin, catechin-(4alpha-->8)-catechin, catechin-(4alpha-->8)-epicatechin, and epicatechin-(4beta-->8)-catechin-(4alpha-->8)-catechin. These compounds were subjected to acid-catalyzed degradation in the presence of phloroglucinol or by partial or complete acid-catalyzed degradation and reaction with benzyl mercaptan followed by desulfurization. The resultant adducts when compared to authentic samples by high-performance liquid chromatography-atmospheric pressure chemical ionization tandem mass spectrometry and high-performance liquid chromatography-electrospray ionization tandem mass spectrometry served to identify the precursors. The composition of proanthocyanidins from 13 different hops was similar, but the concentration of individual compounds showed some differences, which indicated that hop proanthocyanidin profiles are affected by geographic origin and are variable depending on the cultivars.

Authors+Show Affiliations

Department of Chemistry, Oregon State University, Corvallis, Oregon 97331, USA.No affiliation info available

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

16719533

Citation

Li, Hui-Jing, and Max L. Deinzer. "Structural Identification and Distribution of Proanthocyanidins in 13 Different Hops." Journal of Agricultural and Food Chemistry, vol. 54, no. 11, 2006, pp. 4048-56.
Li HJ, Deinzer ML. Structural identification and distribution of proanthocyanidins in 13 different hops. J Agric Food Chem. 2006;54(11):4048-56.
Li, H. J., & Deinzer, M. L. (2006). Structural identification and distribution of proanthocyanidins in 13 different hops. Journal of Agricultural and Food Chemistry, 54(11), 4048-56.
Li HJ, Deinzer ML. Structural Identification and Distribution of Proanthocyanidins in 13 Different Hops. J Agric Food Chem. 2006 May 31;54(11):4048-56. PubMed PMID: 16719533.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Structural identification and distribution of proanthocyanidins in 13 different hops. AU - Li,Hui-Jing, AU - Deinzer,Max L, PY - 2006/5/25/pubmed PY - 2006/6/30/medline PY - 2006/5/25/entrez SP - 4048 EP - 56 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 54 IS - 11 N2 - Ten newly isolated hop proanthocyanidin oligomers and flavan-3-ol monomers from 13 different hops have been identified as gallocatechin, gallocatechin-(4alpha-->8)-catechin, gallocatechin-(4alpha-->6)-catechin, catechin-(4alpha-->8)-gallocatechin, catechin-(4alpha-->6)-gallocatechin, afzelechin-(4alpha-->8)-catechin, catechin-(4alpha-->8)-catechin-(4alpha-->8)-catechin, epicatechin-(4beta-->8)-epicatechin-(4beta-->8)-catechin, catechin-(4alpha-->8)-gallocatechin-(4alpha-->8)-catechin, and gallocatechin-(4alpha-->8)-gallocatechin-(4alpha-->8)-catechin, together with seven previously isolated oligomers, namely, catechin, epicatechin, epicatechin-(4beta-->8)-catechin, epicatechin-(4beta-->8)-epicatechin, catechin-(4alpha-->8)-catechin, catechin-(4alpha-->8)-epicatechin, and epicatechin-(4beta-->8)-catechin-(4alpha-->8)-catechin. These compounds were subjected to acid-catalyzed degradation in the presence of phloroglucinol or by partial or complete acid-catalyzed degradation and reaction with benzyl mercaptan followed by desulfurization. The resultant adducts when compared to authentic samples by high-performance liquid chromatography-atmospheric pressure chemical ionization tandem mass spectrometry and high-performance liquid chromatography-electrospray ionization tandem mass spectrometry served to identify the precursors. The composition of proanthocyanidins from 13 different hops was similar, but the concentration of individual compounds showed some differences, which indicated that hop proanthocyanidin profiles are affected by geographic origin and are variable depending on the cultivars. SN - 0021-8561 UR - https://www.unboundmedicine.com/medline/citation/16719533/Structural_identification_and_distribution_of_proanthocyanidins_in_13_different_hops_ L2 - https://doi.org/10.1021/jf060395r DB - PRIME DP - Unbound Medicine ER -
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