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hydroxybenzoyl; R' = H

Figure 8. Formation of bisflavanols.

A fraction designated as theafulvin has been separated but not resolved. It accounts for only a small proportion of the thearubigin fraction. It is a buff-colored material containing some proanthocyanidin groups, but most of its mass is not completely characterized (44). Theacitrins have also been isolated. They are red substances, similar to the theaflavins but possibly containing additional carboxylic acid groups. They are also present in very small quantities (45,46). Separation techniques have not yet provided methodology for the resolution of the major portion of the thearubigin mixture.

Degradative treatments of the unresolved material have been helpful in piecing together more information. Acid hydrolysis results in the formation of cyanidin and delphinidin (Fig. 9), suggesting proanthocyanidin structures (47). Other degradative procedures have provided evidence for the presence of heterogeneous polymers of fla-vanols and flavanol gallates (48).

Decreases in theaflavins and bisflavanols during fermentation suggest that these compounds are further oxidized and subsequently incorporated into the thearubigin complex. It is also likely that catechin quinones oxidize (8), (10), and glycosides of (11), (12), and (13), leading to incorporation of their oxidation products as well (29). In ad

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