Phenolic compounds related to heartwood coloration of Millettia pendula

Three novel phenolic compounds were isolated from the heartwood of Millettia pendula along with eight known compounds. Among the known compounds, six were isolated from this species for the first time. Structural determination of the isolated compounds was accomplished using 1D and 2D nuclear magnetic resonance spectroscopy and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Two of the isolated compounds, 2 and 6, showed red and purple pigmentation, respectively. These compounds contained a conjugated π system composed of benzofuran and p-benzoquinone moieties. We therefore hypothesize that a hydroquinone moiety, present in precursors of 2 and 6, is autoxidized by activated oxygen in the air to form p-benzoquinone. The difference in colors between these two compounds was due to the difference in the B ring substituents. Expansion of their conjugated pi systems allows 2 and 6 to absorb and reflect light in the visible region, and results in the characteristic purple coloring of M.pendula.