Abstract
Coumarin( 4), 5-methoxycoumarin( 5) and two deep red pigments have been isolated from the extracts of Dalea emoryi. The two pigments, dalrubone and methoxydalrubone differ by a single OMe group and are assigned structures 9 and 10 respectively on the basis of an X-ray crystallographic structure determination as well as their chemical and spectroscopic properties. These pigments appear to be biogenetically derived from a C 6C 3C 6 flavonoid system. Extracts of D. polyadenia were shown to contain coumarin( 4), 5-methoxycoumarin( 5), dalrubone( 9) and 2S-demethoxymatteucinol( 17). Dalrubone undergoes a photochemical oxidation leading to a B-ring contracted product ( 15) having an α-hydroxymethyl ketone group.
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