Article

Influence of gallate esterification on the activity of procyanidin B2 in androgen-dependent human prostate carcinoma LNCaP cells.

Department of Pharmaceutical Sciences, School of Pharmacy, University of Colorado Denver, C238- P15, Research 2, 12700 19th Ave., Aurora, Colorado 80045, USA.
Pharmaceutical Research (impact factor: 4.09). 02/2010; 27(4):619-27. DOI:10.1007/s11095-009-0037-6 pp.619-27
Source: PubMed

ABSTRACT Present study assessed the influence of gallate esterification on the anti-cancer activity of procyanidin B2 (B2) in androgen-dependent human prostate carcinoma LNCaP cells employing B2-3,3'-di-O-gallate (B2-G(2)), two mono-gallate esters B2-3-O-gallate (B2-3G) and B2-3'-O-gallate (B2-3'G) and the parent compound B2, all isolated from grape seed extract (GSE).
Study compounds were isolated from GSE by several chromatographic steps and structures determined by a combination of enzymatic hydrolysis, mass spectrometry and comparisons with standards. Cells, treated with these compounds, were assessed for viability and apoptosis and examined by western blotting.
Gallate esters B2-G(2), B2-3G and B2-3'G significantly decreased LNCaP cell viability; however, B2 and gallic acid were ineffective. Furthermore, only B2-G(2) also significantly decreased cell growth. Decreases in cell viability were largely due to apoptosis induction with B2-G(2) and B2-3'G exhibiting comparable effects, whereas B2-3G was less effective. In mechanistic studies, B2-G(2) and B2-3'G treatments caused caspases-9 and -3 and PARP cleavage, and down-regulated Bcl-2, Bcl-Xl and androgen receptor levels.
Together, our findings demonstrate anti-PCA efficacy of B2-G(2) and suggest that a gallate ester moiety at 3' position of procyanidin B2 contributes more extensively toward the biological activity of the di-gallate ester than esterification of position 3.

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Keywords

3' position
 
androgen receptor levels
 
androgen-dependent human prostate carcinoma LNCaP cells
 
B2-3'G treatments
 
cell growth
 
chromatographic steps
 
comparable effects
 
di-gallate ester
 
gallate ester moiety
 
gallate esterification
 
Gallate esters B2-G(2)
 
grape seed
 
LNCaP cell viability
 
mass spectrometry
 
mono-gallate esters B2-3-O-gallate
 
parent compound B2
 
position 3
 
procyanidin B2
 
procyanidin B2 contributes
 
Study compounds