Abstract
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.
Key words
Silybum marianum
- Asteraceae - milk thistle - silymarin - silybin - isosilybin
References
-
1
Graf T N, Wani M C, Agarwal R, Kroll D J, Oberlies N H.
Gram-scale purification of flavonolignan diastereoisomers from Silybum marianum (milk thistle) extract in support of preclinical in vivo studies for prostate cancer chemoprevention.
Planta Med.
2007;
73
1495-1501
-
2
Deep G, Oberlies N H, Kroll D J, Agarwal R.
Isosilybin B and isosilybin A inhibit growth, induce G1 arrest and cause apoptosis in human prostate cancer LNCaP and 22Rv1 cells.
Carcinogenesis.
2007;
28
1533-1542
-
3
Deep G, Oberlies N H, Kroll D J, Agarwal R.
Isosilybin B causes androgen receptor degradation in human prostate carcinoma cells via PI3K-Akt-Mdm2-mediated pathway.
Oncogene.
2008;
27
3986-3998
-
4
Deep G, Oberlies N H, Kroll D J, Agarwal R.
Identifying the differential effects of silymarin constituents on cell growth and cell cycle regulatory molecules in human prostate cancer cells.
Int J Cancer.
2008;
123
41-50
-
5
Deep G, Raina K, Singh R P, Oberlies N H, Kroll D J, Agarwal R.
Isosilibinin inhibits advanced human prostate cancer growth in athymic nude mice: comparison with silymarin and silibinin.
Int J Cancer.
2008;
123
2750-2758
-
6
Kroll D J, Shaw H S, Oberlies N H.
Milk thistle nomenclature: why it matters in cancer research and pharmacokinetic studies.
Integr Cancer Ther.
2007;
6
110-119
-
7
Davis-Searles P R, Nakanishi Y, Kim N C, Graf T N, Oberlies N H, Wani M C, Wall M E, Agarwal R, Kroll D J.
Milk thistle and prostate cancer: differential effects of pure flavonolignans from Silybum marianum on antiproliferative end points in human prostate carcinoma cells.
Cancer Res.
2005;
65
4448-4457
-
8
Kim N C, Graf T N, Sparacino C M, Wani M C, Wall M E.
Complete isolation and characterization of silybins and isosilybins from milk thistle (Silybum marianum).
Org Biomol Chem.
2003;
1
1684-1689
-
9
Kim N C, Graf T N, Sparacino C M, Wani M C, Wall M E.
Complete isolation and characterization of silybins and isosilybins from milk thistle (Silybum marianum).
Org Biomol Chem.
2003;
1
3470
-
10
Agarwal R, Agarwal C, Ichikawa H, Singh R P, Aggarwal B B.
Anticancer potential of silymarin: from bench to bed side.
Anticancer Res.
2006;
26
4457-4498
-
11
Ramasamy K, Agarwal R.
Multitargeted therapy of cancer by silymarin.
Cancer Lett.
2008;
269
352-362
Ph.D. Nicholas H. Oberlies
Department of Chemistry and Biochemistry
University of North Carolina at Greensboro
P. O. Box 26170
435 Sullivan Science Building
Greensboro, NC 27402–6170
USA
Telefon: + 1 33 63 34 54 74
Fax: + 1 33 63 34 54 02
eMail: Nicholas_Oberlies@uncg.edu
