Synthesis of proposed structure of ledebourin A.

Naturally occurring homoisoflavonoids have attracted significant attention in the field of medicinal chemistry due to their potential health benefits and diverse range of biological properties. Recently, C-prenylated homoisoflavonoids, namely ledebourin A, B, and C, were isolated from the bulbs of Ledebouria floribunda and have exhibited potent antioxidant activity. In this study, we successfully synthesized ledebourin A and its regioisomer, compounds 1 and 9. By comparing the NMR spectra of the synthesized compounds with those of reported ledebourin A, we observed discrepancies. Nonetheless, our synthesis and subsequent findings offer valuable insights into the structural revision and biological activities of these unique prenylated homoisoflavonoids. Both synthesized compounds 1 and 9 exhibited no toxicity towards Hep-G2 cells and displayed the ability to recover glyceraldehyde-induced cell death, suggesting their potential as protective agents against liver damage.