Planta Med 2012; 78 - P_41
DOI: 10.1055/s-0032-1307549

Sterioselective Synthesis of S(-) Equol

A Chittiboyina 1, S Rotte 1, C Yalamanchili 2, TJ Smillie 1, IA Khan 1, 2
  • 1National Center for Natural Products Research
  • 2Department of Pharmacognosy, School of Pharmacy, The University of Mississippi, University, MS 38677

Isoflavonoids are secondary metabolites of formonentin (1) and daidzein (2) obtained from plants and act as phytoalexins in the defense against pathogens of the plants[1]. When daidzein (2) is ingested into our body by eating soy and foods thereof, and is transformed to S(-) Equol (3) and other metabolites[2] by the intestinal micro flora such as gut microflora. S(-) Equol (3) which has a chiral center at the C3 position of the chroman ring stimulates the estrogenic response most effectively through binding to the Estrogenic Receptor β (ERβ)[3]. Enantiopure synthesis of S(-) Equol is essential to elucidate its detailed biological effects. In our group, a novel strategy for the enantioselective synthesis of S(-) Equol (3) using Evans alkylation as the critical chiral inducing reaction is presented and the full synthetic details will be presented.

Formononetin 1

Diadzein 2

S(-) Equol 3

Acknowledgements: The United States Department of Agriculture, Agricultural Research Service, Specific Cooperative Agreement No. 58–6408–2-0009 and the University of Illinois Botanical Research Center (BRC) entitled “Botanical Identification, Characterization, Quality Assurance and Quality Control“, funded by NIH, Prime award number 1P50AT006268–02. References: [1] Veitch NC (2007) Natural Product Reports 24: 417–464. [2] Chang Y-C, Nair MG (1995)J Nat Prod 58(12): 1892–1896. [3] Morito K, Hirose T, et al. (2001) Biological & Pharm Bull 24: 351–356.