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Floral procyanidins of the forage legume red clover (Trifolium pratense L.).
J Agric Food Chem. 2004 Mar 24; 52(6):1581-5.JA

Abstract

The chemical characteristics of the purified procyanidin polymers of the flowers of the forage legume red clover (Trifolium pratense L.) were studied by (13)C NMR, acid-catalyzed degradation with benzyl mercaptan, and electrospray ionization mass spectrometry (ESI-MS). The (13)C NMR showed that the fraction consisted of predominantly procyanidin polymers. The thiolysis reaction products indicated a mean degree of polymerization (mDP) of 9.3 with epicatechin (81%) as the abundant flavan-3-ol extension unit and the terminating units dominated by catechin (95%). ESI-MS showed a range of oligomeric procyanidin ions (DP of 2-11). The white clover floral prodelphinidins consist of terminal units with nearly equal proportions of epigallocatechin (52%) and gallocatechin (48%) and extender units showing epigallocatechin (56%) and gallocatechin (39%). The dramatic difference in the stereochemistry of the terminal and extender units observed for the red clover floral procyanidins contrasts with the mixture of cis and trans stereochemistry observed for white clover floral prodelphinidins.

Authors+Show Affiliations

Nutrition and Behavior and Plant Breeding and Genomics, AgResearch Ltd., Grasslands Research Centre, Private Bag 11008, Palmerston North, New Zealand.No 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

15030214

Citation

Sivakumaran, Subathira, et al. "Floral Procyanidins of the Forage Legume Red Clover (Trifolium Pratense L.)." Journal of Agricultural and Food Chemistry, vol. 52, no. 6, 2004, pp. 1581-5.
Sivakumaran S, Meagher LP, Foo LY, et al. Floral procyanidins of the forage legume red clover (Trifolium pratense L.). J Agric Food Chem. 2004;52(6):1581-5.
Sivakumaran, S., Meagher, L. P., Foo, L. Y., Lane, G. A., Fraser, K., & Rumball, W. (2004). Floral procyanidins of the forage legume red clover (Trifolium pratense L.). Journal of Agricultural and Food Chemistry, 52(6), 1581-5.
Sivakumaran S, et al. Floral Procyanidins of the Forage Legume Red Clover (Trifolium Pratense L.). J Agric Food Chem. 2004 Mar 24;52(6):1581-5. PubMed PMID: 15030214.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Floral procyanidins of the forage legume red clover (Trifolium pratense L.). AU - Sivakumaran,Subathira, AU - Meagher,Lucy P, AU - Foo,Lai Yeap, AU - Lane,Geoffrey A, AU - Fraser,Karl, AU - Rumball,William, PY - 2004/3/20/pubmed PY - 2004/5/8/medline PY - 2004/3/20/entrez SP - 1581 EP - 5 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 52 IS - 6 N2 - The chemical characteristics of the purified procyanidin polymers of the flowers of the forage legume red clover (Trifolium pratense L.) were studied by (13)C NMR, acid-catalyzed degradation with benzyl mercaptan, and electrospray ionization mass spectrometry (ESI-MS). The (13)C NMR showed that the fraction consisted of predominantly procyanidin polymers. The thiolysis reaction products indicated a mean degree of polymerization (mDP) of 9.3 with epicatechin (81%) as the abundant flavan-3-ol extension unit and the terminating units dominated by catechin (95%). ESI-MS showed a range of oligomeric procyanidin ions (DP of 2-11). The white clover floral prodelphinidins consist of terminal units with nearly equal proportions of epigallocatechin (52%) and gallocatechin (48%) and extender units showing epigallocatechin (56%) and gallocatechin (39%). The dramatic difference in the stereochemistry of the terminal and extender units observed for the red clover floral procyanidins contrasts with the mixture of cis and trans stereochemistry observed for white clover floral prodelphinidins. SN - 0021-8561 UR - https://www.unboundmedicine.com/medline/citation/15030214/Floral_procyanidins_of_the_forage_legume_red_clover__Trifolium_pratense_L___ L2 - https://doi.org/10.1021/jf035379y DB - PRIME DP - Unbound Medicine ER -