New insight into the biosynthesis of flavanolignans in the white-flowered variant of Silybum marianum.
It has been demonstrated that besides the known flavanolignan constituents of the white-flowered variant of Silybum marianum, (-)-silandrin A (3a) and (-)-isosilandrin A (4a); their trans-benzodioxane diastereomers, (-)-silandrin B (3b) and (-)-isosilandrin B (4b), are also produced by the plant. Moreover, the isolation of their cis-benzodioxane diastereomers, (-)-isocisilandrin (5) and cisilandrin (6), confirm that the previously proposed biosynthetic pathway involving a nonselective O-beta coupling is correct.
Nyiredy
Sz
S
Béres Pharmaceuticals, Budapest, Hungary.
Samu
Zs
Z
Szücs
Z
Z
Gulácsi
K
K
Kurtán
T
T
Antus
S
S
D053898:Biosynthetic Pathways; D002851:Chromatography, High Pressure Liquid; D044947:Flavonolignans / Q000096:biosynthesis* / Q000737:chemistry / Q000302:isolation & purification*; D020944:Silybum marianum / Q000737:chemistry / Q000378:metabolism*; D012838:Silymarin / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism
D044947:Flavonolignans; D012838:Silymarin; C075820:isosilybin