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| - Floral Procyanidins of the Forage Legume Red Clover(Trifolium pratense L.)
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| - The chemical characteristics of the purified procyanidin polymers of the flowers of the forage legumered clover (Trifolium pratense L.) were studied by 13C NMR, acid-catalyzed degradation with benzylmercaptan, and electrospray ionization mass spectrometry (ESI-MS). The 13C NMR showed that thefraction consisted of predominantly procyanidin polymers. The thiolysis reaction products indicateda mean degree of polymerization (mDP) of 9.3 with epicatechin (81%) as the abundant flavan-3-olextension unit and the terminating units dominated by catechin (95%). ESI-MS showed a range ofoligomeric procyanidin ions (DP of 2−11). The white clover floral prodelphinidins consist of terminalunits with nearly equal proportions of epigallocatechin (52%) and gallocatechin (48%) and extenderunits showing epigallocatechin (56%) and gallocatechin (39%). The dramatic difference in thestereochemistry of the terminal and extender units observed for the red clover floral procyanidinscontrasts with the mixture of cis and trans stereochemistry observed for white clover floralprodelphinidins. Keywords: Leguminosae; red clover flowers; Trifolium pratense; Trifolium repens; proanthocyanidins;procyanidins; prodelphinidins; catechin; 13C NMR; thiolysis; electrospray mass spectrometry
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