Three proanthocyanidin trimers possessing A-type interflavanoid linkages, epicatechin-(4beta-->6)-epicatechin-(4beta-->8, 2beta-->O-->7)-epicatechin (4), epicatechin-(4beta-->8, 2beta-->O-->7)-epicatechin-(4beta-->8)-epicatechin (5), and epicatechin-(4beta-->8)-epicatechin-(4beta-->8, 2beta-->O-->7)-epicatechin (6), were isolated from the ripe fruits of Vaccinium macrocarpon (cranberry) and prevented adherence of P-fimbriated Escherichia coli isolates from the urinary tract to cellular surfaces containing alpha-Gal(1-->4)beta-Gal receptor sequences similar to those on uroepithelial cells. The structure of 4 was elucidated by a combination of spectroscopic methods and acid-catalyzed degradation with phloroglucinol. Also isolated were the weakly active epicatechin-(4beta-->8, 2beta-->O-->7)-epicatechin (procyanidin A2) (3) and the inactive monomer epicatechin (1) and the inactive dimer epicatechin-(4beta-->8)-epicatechin (procyanidin B2) (2).

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Sixteen linalool derivatives and a variety of aliphatic acids and diacids, aromatic acids, and phenols (total of 61 components) were identified in the methylated diethyl ether extracts of New Zealand nodding thistle (Carduus nutans) honeys using GC-FID and combined GC-MS methods. Separation of the diethyl ether extracts afforded three dominant linalool derivatives which were identified using one-and two-dimensional NMR procedures as (£)-2,6-dimethyl-3,7-octadiene-2,6-diol (3), (Z)-2,6dimethyl-6-hydroxy-2,7-dienal (8), and (£)-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid (characterized as methyl ester, 6). The minor components, a,5-dimethyl-5-ethenyl-2-tetrahydrofuranacetaldehydes [lilac aldehydes (11), four isomers] and /8,5-dimethyl-5-ethenyl-2-tetrahydrofuranethanols [lilac alcohols (10), four isomers], were identified by comparison with synthetic samples. The total level of linalool derivatives in the nodding thistle honey samples was between 15 and 87 Mg/g of honey (average level 43 Mg/g of honey).

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