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Floral Trifolium proanthocyanidins: polyphenol formation and compositional diversity.
J Agric Food Chem. 2006 Jul 26; 54(15):5482-8.JA

Abstract

Recent studies on the biosynthesis of proanthocyandins have identified key genes and enzymes in the formation of 2,3-cis-flavan-3-ols (epiafzelechin, epicatechin, and epigallocatechin). However, the enzymes that catalyze the polymerization of monomer units remain unknown. Studies of proanthocyanidin synthesis have involved the reference plant, Arabidopsis thaliana, forage legumes, tobacco, and grape. For this paper the floral proanthocyanidins of 10 Trifolium species were studied to identify candidates with contrasting proanthocyanidin chemistry, for the identification of factors involved in polymerization. Proanthocyandins were present in the floral portions (3.1-12.2 g/100 g of dry matter) of Trifolium spp. Thiolyic cleavage of proanthocyanidin fractions liberated flavan-3-ol extension units dominated by cis stereochemistry. The terminal units' stereochemistry of T. michelianum was exclusively trans (catechin), that of T. hirtum mixed trans (catechin and gallocatechin), and that of T. vesiculosum equal proportions of trans and cis (catechin and epicatechin). Compositional dispersion for oligomers was determined by MALDI-TOF MS, which showed a range of ions up to approximately 2200 Da. The three Trifolium spp. highlighted, all annuals, may warrant investigation for insights into proanthocyanidins biosynthesis.

Authors+Show Affiliations

Food and Health and Forage Improvement, AgResearch Ltd., Grasslands Research Centre, Palmerston North, New Zealand. lucy.meagher@fonterra.comNo 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

16848535

Citation

Meagher, Lucy P., et al. "Floral Trifolium Proanthocyanidins: Polyphenol Formation and Compositional Diversity." Journal of Agricultural and Food Chemistry, vol. 54, no. 15, 2006, pp. 5482-8.
Meagher LP, Widdup K, Sivakumaran S, et al. Floral Trifolium proanthocyanidins: polyphenol formation and compositional diversity. J Agric Food Chem. 2006;54(15):5482-8.
Meagher, L. P., Widdup, K., Sivakumaran, S., Lucas, R., & Rumball, W. (2006). Floral Trifolium proanthocyanidins: polyphenol formation and compositional diversity. Journal of Agricultural and Food Chemistry, 54(15), 5482-8.
Meagher LP, et al. Floral Trifolium Proanthocyanidins: Polyphenol Formation and Compositional Diversity. J Agric Food Chem. 2006 Jul 26;54(15):5482-8. PubMed PMID: 16848535.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Floral Trifolium proanthocyanidins: polyphenol formation and compositional diversity. AU - Meagher,Lucy P, AU - Widdup,Keith, AU - Sivakumaran,Subathira, AU - Lucas,Richard, AU - Rumball,William, PY - 2006/7/20/pubmed PY - 2006/8/30/medline PY - 2006/7/20/entrez SP - 5482 EP - 8 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 54 IS - 15 N2 - Recent studies on the biosynthesis of proanthocyandins have identified key genes and enzymes in the formation of 2,3-cis-flavan-3-ols (epiafzelechin, epicatechin, and epigallocatechin). However, the enzymes that catalyze the polymerization of monomer units remain unknown. Studies of proanthocyanidin synthesis have involved the reference plant, Arabidopsis thaliana, forage legumes, tobacco, and grape. For this paper the floral proanthocyanidins of 10 Trifolium species were studied to identify candidates with contrasting proanthocyanidin chemistry, for the identification of factors involved in polymerization. Proanthocyandins were present in the floral portions (3.1-12.2 g/100 g of dry matter) of Trifolium spp. Thiolyic cleavage of proanthocyanidin fractions liberated flavan-3-ol extension units dominated by cis stereochemistry. The terminal units' stereochemistry of T. michelianum was exclusively trans (catechin), that of T. hirtum mixed trans (catechin and gallocatechin), and that of T. vesiculosum equal proportions of trans and cis (catechin and epicatechin). Compositional dispersion for oligomers was determined by MALDI-TOF MS, which showed a range of ions up to approximately 2200 Da. The three Trifolium spp. highlighted, all annuals, may warrant investigation for insights into proanthocyanidins biosynthesis. SN - 0021-8561 UR - https://www.unboundmedicine.com/medline/citation/16848535/Floral_Trifolium_proanthocyanidins:_polyphenol_formation_and_compositional_diversity_ L2 - https://doi.org/10.1021/jf0609025 DB - PRIME DP - Unbound Medicine ER -