Large-scale isolation of flavonolignans from Silybum marianum extract affords new minor constituents and preliminary structure-activity relationships.

The gram-scale isolation of the major flavonolignan diastereoisomers from milk thistle ( Silybum marianum) extract provided an entree into the isolation of two related analogues that are present in extremely minute quantities. The isolation and structure elucidation of these two new compounds, which we have termed isosilybin C and isosilybin D due to their structural similarities to isosilybin A and isosilybin B, respectively, afforded a preliminary analysis of structure-activity relationships toward prostate cancer growth, survival, and apoptotic endpoints.

[1]  R. Agarwal,et al.  Isosilibinin inhibits advanced human prostate cancer growth in athymic nude mice: Comparison with silymarin and silibinin , 2008, International journal of cancer.

[2]  R. Agarwal,et al.  Multitargeted therapy of cancer by silymarin. , 2008, Cancer letters.

[3]  R. Agarwal,et al.  Identifying the differential effects of silymarin constituents on cell growth and cell cycle regulatory molecules in human prostate cancer cells , 2008, International journal of cancer.

[4]  R. Agarwal,et al.  Isosilybin B causes androgen receptor degradation in human prostate carcinoma cells via PI3K-Akt-Mdm2-mediated pathway , 2008, Oncogene.

[5]  R. Agarwal,et al.  Gram-scale purification of flavonolignan diastereoisomers from Silybum marianum (Milk Thistle) extract in support of preclinical in vivo studies for prostate cancer chemoprevention. , 2007, Planta medica.

[6]  R. Agarwal,et al.  Isosilybin B and isosilybin A inhibit growth, induce G1 arrest and cause apoptosis in human prostate cancer LNCaP and 22Rv1 cells. , 2007, Carcinogenesis.

[7]  N. Oberlies,et al.  Milk Thistle Nomenclature: Why It Matters in Cancer Research and Pharmacokinetic Studies , 2007, Integrative cancer therapies.

[8]  B. Aggarwal,et al.  Anticancer potential of silymarin: from bench to bed side. , 2006, Anticancer research.

[9]  R. Agarwal,et al.  Milk thistle and prostate cancer: differential effects of pure flavonolignans from Silybum marianum on antiproliferative end points in human prostate carcinoma cells. , 2005, Cancer research.

[10]  Nam-Cheol Kim,et al.  Complete isolation and characterization of silybins and isosilybins from milk thistle (Silybum marianum). , 2003, Organic & biomolecular chemistry.