Podophyllotoxin related lignans in plants and cell cultures of Linum flavum

The isolation and structure elucidation of 5′-demethoxy 5-methoxypodophyllotoxin and a number of structurally closely related minor compounds of M,s 370, 400 and 430, from in vitro cultured cells are reported. All compounds possess the same stereochemical configuration at C-1, C-2, C-3 and C-4, but differ in their hydroxylation and methoxylation patterns at C-5, C-4′ and C-5′. Further, podophyllotoxin itself and matairesinol, a hypothetical biosynthetic precursor were detected. Data on the quantities of the previously isolated 5-methoxypodophyllotoxin and its 4-β- d-glucoside, as well as of 5′-demethoxy 5-methoxypodophyllotoxin and related compounds present in plants and cell cultures is presented.