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. 2013 Mar 28;8(3):e60074. doi: 10.1371/journal.pone.0060074

Table 4. Effect of pure optical isomers of silybin, 2,3-dehydrosilybin, 7-O-methylsilybin, and 7-O-galloylsilybin on HTB9, HCT116, and PC3 cancer cell growth.

Treatments Total cell no. x105 (% growth inhibition)
HTB9 Cells 24 hrs 48 h
30 µM 60 µM 30 µM 60 µM
DMSO 2.5±0.1 5.5±0.2
Silybin A 2.0±0.1# (20%) 2.0±0.3$ (20%) 4.7±0.8* (15%) 3.9±0.3* (29%)
2,3-dehydrosilybin A 1.8±0.1* (28%) 1.3±0.1* (48%) 1.8±0.1* (67%) 1.3±0.0* (76%)
7-O-methylsilybin A 1.5*±0.1* (40%) 1.2±0.1* (52%) 1.8±0.1* (67%) 0.5±0.1* (91%)
7-O-galloylsilybin A 1.7±0.1* (32%) 1.0±0.0* (60%) 1.5±0.1* (73%) 1.1±0.1* (80%)
Silybin B 2.2±0.1 (12%) 1.7±0.2* (32%) 4.2±0.3* (24%) 3.3±0.3* (40%)
2,3-dehydrosilybin B 1.3±0.1* (48%) 1.3±0.1* (48%) 1.5±0.1* (73%) 1.4±0.1* (75%)
7-O-methylsilybin B 2.1±0.1 (16%) 1.2±0.2* (52%) 2.2±0.1* (60%) 0.9±0.1* (84%)
7-O-galloylsilybin B 1.3±0.1* (48%) 0.8±0.2* (68%) 1.4±0.1* (75%) 0.9±0.1* (84%)
HCT116 Cells 24 hrs 48 h
30 µM 60 µM 30 µM 60 µM
DMSO 3.6±0.2 8.6±0.4
Silybin A 3.4±0.3 (6%) 2.9±0.3# (19%) 8.7±0.4 (−1%) 7.0±0.3* (19%)
2,3-dehydrosilybin A 1.9±.0.1* (47%) 1.7±0.2* (53%) 1.7±0.1* (80%) 1.0±0.1* (88%)
7-O-methylsilybin A 2.0±0.3* (44%) 1.2±0.2* (67%) 1.1±0.1* (87%) 0.8±0.2* (90%)
7-O-galloylsilybin A 1.8±0.2* (50%) 1.0±0.1* (72%) 1.0±0.0* (88%) 0.6±0.1* (93%)
Silybin B 3.2±0.1 (11%) 3.3±0.1 (8.3%) 7.2±0.2* (16%) 6.1±0.6* (29%)
2,3-dehydrosilybin B 2.2±0.0* (39%) 1.2±0.1* (67%) 1.3±0.1* (85%) 1.2±0.1* (86%)
7-O-methylsilybin B 2.6±0.3* (28%) 1.3±0.1* (64%) 2.0±0.1* (77%) 1.0±0.1* (88%)
7-O-galloylsilybin B 1.5±0.1* (58%) 1.1±0.1* (69%) 0.8±0.2* (91%) 1.0±0.0* (88%)
PC3 cells 24 hrs 48 h
30 µM 60 µM 30 µM 60 µM
DMSO 2.2±0.10 4.5±0.2
Silybin A 1.9±0.01 (14%) 1.9±0.1 (14%) 4.0±0.2 (11%) 3.7±0.3* (17.8%)
2,3-dehydrosilybin A 0.7±0.0* (68%) 0.1±0.1* (95%) 1.2±0.0* (73%) 1.3±0.1* (71%)
7-O-methylsilybin A 0.8±0.1* (64%) 1.1±0.1* (50%) 1.0±0.2* (78%) 0.9±0.0* (80%)
7-O-galloylsilybin A 1.7±0.4$ (23%) 0.7±0.1* (68%) 0.8±0.1* (82%) 1.1±0.1* (76%)
Silybin B 1.7±0.1$ (23%) 1.6±0.1* (27%) 3.6±0.2* (20%) 3.3±0.1* (27%)
2,3-dehydrosilybin B 1.1±0.1* (50%) 1.1±0.1* (50%) 1.1±0.1* (76%) 1.0±0.1* (78%)
7-O-methylsilybin B 1.2±0.2* (45%) 1.2±0.1* (45%) 1.2±0.3* (73%) 1.3±0.1* (71%)
7-O-galloylsilybin B 0.4±0.0* (82%) 0.3±0.1* (86%) 0.7±0.1* (84%) 0.4±0.1* (91%)
*

p≤0.001;

#

p≤0.01;

$

p≤0.05.