Published:Journal of Chromatographic Science,
ISSN 0021-9665 Volume
46, Number 2, February 2008, pp. 93-96
New Insight into the Biosynthesis of Flavanolignans
in the White-Flowered Variant of Silybum marianum
Sz. Nyiredy[1], Zs. Samu[2], Z. Szücs[1],
K. Gulácsi[3], T. Kurtán[3], and S. Antus[3,4],
[1]Research Institute for Medicinal Plants, P.O. Box 11, H-2011
Budakalász, Hungary;
[2]Béres Pharmaceuticals,
2-4 Mikoviny, H-1037 Budapest, Hungary;
[3]Department of Organic
Chemistry, University of Debrecen, P.O. Box 20, H-4010 Debrecen,
Hungary; and
[4]Research Group for Carbohydrates of Hungarian
Academy of Sciences, University of Debrecen, P.O. Box 94, H-4010
Debrecen, Hungary
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-b coupling is correct.
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