First Synthesis of Racemic Methylophiopogonanone B and Its Inhibitory Activity of Hypoxia-Inducible Factor-1α

Methylophiopogonanone B, a constituent of Ophiopogonis tuber, found to be a potent inhibitor of hypoxia induced factor-1α (HIF-1α) activity, was synthesized from 2,4,6-trihydroxy-3,5-dimethylacetophenone in 57% yield.The synthetic methylophiopogonanone B inhibited the reporter activity at 3 to 10 μg/mL.Methylophiopogonanone B (1) (Figure 1) is a homoisoflavanone, found in Ophiopogonis tuber (Ophiopogon japonicus KER-GAWLER var.genuinus Maxim.or Ophiopogon japonicus KER-GAWLER cv.