|
|
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result sql = Antitumor activity of resveratrol and its sulfated metabolites against human breast cancer cells.
Antitumor activity of resveratrol and its sulfated metabolites against human breast cancer cells.char = R;code = 82
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char = t;code = 116
char = r;code = 114
char = a;code = 97
char = s;code = 115
char = t;code = 116
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char = t;code = 116
char = o;code = 111
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char = r;code = 114
char = e;code = 101
char = s;code = 115
char = v;code = 118
char = e;code = 101
char = r;code = 114
char = a;code = 97
char = t;code = 116
char = r;code = 114
char = o;code = 111
char = l;code = 108
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char = ;code = 32
char = a;code = 97
char = l;code = 108
char = l;code = 108
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = r;code = 114
char = e;code = 101
char = e;code = 101
char = ;code = 32
char = s;code = 115
char = u;code = 117
char = l;code = 108
char = f;code = 102
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = m;code = 109
char = e;code = 101
char = t;code = 116
char = a;code = 97
char = b;code = 98
char = o;code = 111
char = l;code = 108
char = i;code = 105
char = t;code = 116
char = e;code = 101
char = s;code = 115
char = ;code = 32
char = w;code = 119
char = e;code = 101
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = l;code = 108
char = e;code = 101
char = s;code = 115
char = s;code = 115
char = ;code = 32
char = p;code = 112
char = o;code = 111
char = t;code = 116
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = ;code = 32
char = a;code = 97
char = g;code = 103
char = a;code = 97
char = i;code = 105
char = n;code = 110
char = s;code = 115
char = t;code = 116
char = ;code = 32
char = M;code = 77
char = C;code = 67
char = F;code = 70
char = -;code = 45
char = 7;code = 55
char = ,;code = 44
char = ;code = 32
char = M;code = 77
char = D;code = 68
char = A;code = 65
char = -;code = 45
char = M;code = 77
char = B;code = 66
char = -;code = 45
char = 2;code = 50
char = 3;code = 51
char = 1;code = 49
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = Z;code = 90
char = R;code = 82
char = -;code = 45
char = 7;code = 55
char = 5;code = 53
char = -;code = 45
char = 1;code = 49
char = ;code = 32
char = c;code = 99
char = e;code = 101
char = l;code = 108
char = l;code = 108
char = s;code = 115
char = ;code = 32
char = (;code = 40
char = ;code = 32
char = t;code = 116
char = r;code = 114
char = a;code = 97
char = n;code = 110
char = s;code = 115
char = -;code = 45
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = v;code = 118
char = e;code = 101
char = r;code = 114
char = a;code = 97
char = t;code = 116
char = r;code = 114
char = o;code = 111
char = l;code = 108
char = ;code = 32
char = 3;code = 51
char = -;code = 45
char = ;code = 32
char = O;code = 79
char = -;code = 45
char = s;code = 115
char = u;code = 117
char = l;code = 108
char = f;code = 102
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = ;code = 32
char = <;code = 60
char = ;code = 32
char = t;code = 116
char = r;code = 114
char = a;code = 97
char = n;code = 110
char = s;code = 115
char = -;code = 45
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = v;code = 118
char = e;code = 101
char = r;code = 114
char = a;code = 97
char = t;code = 116
char = r;code = 114
char = o;code = 111
char = l;code = 108
char = ;code = 32
char = 4;code = 52
char = ';code = 39
char = -;code = 45
char = ;code = 32
char = O;code = 79
char = -;code = 45
char = s;code = 115
char = u;code = 117
char = l;code = 108
char = f;code = 102
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = ;code = 32
char = <;code = 60
char = ;code = 32
char = t;code = 116
char = r;code = 114
char = a;code = 97
char = n;code = 110
char = s;code = 115
char = -;code = 45
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = v;code = 118
char = e;code = 101
char = r;code = 114
char = a;code = 97
char = t;code = 116
char = r;code = 114
char = o;code = 111
char = l;code = 108
char = ;code = 32
char = 3;code = 51
char = -;code = 45
char = ;code = 32
char = O;code = 79
char = -;code = 45
char = 4;code = 52
char = ';code = 39
char = -;code = 45
char = ;code = 32
char = O;code = 79
char = -;code = 45
char = d;code = 100
char = i;code = 105
char = s;code = 115
char = u;code = 117
char = l;code = 108
char = f;code = 102
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = );code = 41
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = d;code = 100
char = i;code = 105
char = c;code = 99
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = a;code = 97
char = t;code = 116
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = y;code = 121
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = j;code = 106
char = u;code = 117
char = g;code = 103
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = p;code = 112
char = h;code = 104
char = e;code = 101
char = n;code = 110
char = o;code = 111
char = l;code = 108
char = i;code = 105
char = c;code = 99
char = ;code = 32
char = g;code = 103
char = r;code = 114
char = o;code = 111
char = u;code = 117
char = p;code = 112
char = s;code = 115
char = ;code = 32
char = w;code = 119
char = i;code = 105
char = t;code = 116
char = h;code = 104
char = ;code = 32
char = s;code = 115
char = u;code = 117
char = l;code = 108
char = f;code = 102
char = u;code = 117
char = r;code = 114
char = i;code = 105
char = c;code = 99
char = ;code = 32
char = a;code = 97
char = c;code = 99
char = i;code = 105
char = d;code = 100
char = ;code = 32
char = s;code = 115
char = t;code = 116
char = r;code = 114
char = o;code = 111
char = n;code = 110
char = g;code = 103
char = l;code = 108
char = y;code = 121
char = ;code = 32
char = a;code = 97
char = f;code = 102
char = f;code = 102
char = e;code = 101
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = c;code = 99
char = y;code = 121
char = t;code = 116
char = o;code = 111
char = t;code = 116
char = o;code = 111
char = x;code = 120
char = i;code = 105
char = c;code = 99
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = .;code = 46
char = ;code = 32
char = I;code = 73
char = n;code = 110
char = t;code = 116
char = e;code = 101
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = t;code = 116
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = l;code = 108
char = y;code = 121
char = ,;code = 44
char = ;code = 32
char = a;code = 97
char = l;code = 108
char = l;code = 108
char = ;code = 32
char = s;code = 115
char = u;code = 117
char = l;code = 108
char = f;code = 102
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = m;code = 109
char = e;code = 101
char = t;code = 116
char = a;code = 97
char = b;code = 98
char = o;code = 111
char = l;code = 108
char = i;code = 105
char = t;code = 116
char = e;code = 101
char = s;code = 115
char = ;code = 32
char = w;code = 119
char = e;code = 101
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = d;code = 100
char = u;code = 117
char = c;code = 99
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = a;code = 97
char = b;code = 98
char = o;code = 111
char = u;code = 117
char = t;code = 116
char = ;code = 32
char = 1;code = 49
char = 0;code = 48
char = -;code = 45
char = f;code = 102
char = o;code = 111
char = l;code = 108
char = d;code = 100
char = ,;code = 44
char = ;code = 32
char = b;code = 98
char = u;code = 117
char = t;code = 116
char = ;code = 32
char = s;code = 115
char = h;code = 104
char = o;code = 111
char = w;code = 119
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = n;code = 110
char = e;code = 101
char = a;code = 97
char = r;code = 114
char = l;code = 108
char = y;code = 121
char = ;code = 32
char = e;code = 101
char = q;code = 113
char = u;code = 117
char = a;code = 97
char = l;code = 108
char = ;code = 32
char = c;code = 99
char = y;code = 121
char = t;code = 116
char = o;code = 111
char = t;code = 116
char = o;code = 111
char = x;code = 120
char = i;code = 105
char = c;code = 99
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = w;code = 119
char = a;code = 97
char = r;code = 114
char = d;code = 100
char = s;code = 115
char = ;code = 32
char = n;code = 110
char = o;code = 111
char = n;code = 110
char = m;code = 109
char = a;code = 97
char = l;code = 108
char = i;code = 105
char = g;code = 103
char = n;code = 110
char = a;code = 97
char = n;code = 110
char = t;code = 116
char = ;code = 32
char = M;code = 77
char = C;code = 67
char = F;code = 70
char = -;code = 45
char = 1;code = 49
char = 0;code = 48
char = A;code = 65
char = ;code = 32
char = b;code = 98
char = r;code = 114
char = e;code = 101
char = a;code = 97
char = s;code = 115
char = t;code = 116
char = ;code = 32
char = c;code = 99
char = e;code = 101
char = l;code = 108
char = l;code = 108
char = s;code = 115
char = ;code = 32
char = (;code = 40
char = I;code = 73
char = C;code = 67
char = ;code = 32
char = (;code = 40
char = 5;code = 53
char = 0;code = 48
char = ;code = 32
char = s;code = 115
char = );code = 41
char = :;code = 58
char = ;code = 32
char = 2;code = 50
char = 0;code = 48
char = 2;code = 50
char = -;code = 45
char = 2;code = 50
char = 2;code = 50
char = 8;code = 56
char = ;code = 32
char = m;code = 109
char = i;code = 105
char = c;code = 99
char = r;code = 114
char = o;code = 111
char = M;code = 77
char = );code = 41
char = .;code = 46
char = ;code = 32
char = I;code = 73
char = n;code = 110
char = ;code = 32
char = s;code = 115
char = u;code = 117
char = m;code = 109
char = m;code = 109
char = a;code = 97
char = r;code = 114
char = y;code = 121
char = ,;code = 44
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = t;code = 116
char = r;code = 114
char = a;code = 97
char = s;code = 115
char = t;code = 116
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = v;code = 118
char = e;code = 101
char = r;code = 114
char = a;code = 97
char = t;code = 116
char = r;code = 114
char = o;code = 111
char = l;code = 108
char = ;code = 32
char = i;code = 105
char = t;code = 116
char = s;code = 115
char = ;code = 32
char = s;code = 115
char = u;code = 117
char = l;code = 108
char = f;code = 102
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = m;code = 109
char = e;code = 101
char = t;code = 116
char = a;code = 97
char = b;code = 98
char = o;code = 111
char = l;code = 108
char = i;code = 105
char = t;code = 116
char = e;code = 101
char = s;code = 115
char = ;code = 32
char = s;code = 115
char = h;code = 104
char = o;code = 111
char = w;code = 119
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = p;code = 112
char = o;code = 111
char = o;code = 111
char = r;code = 114
char = ;code = 32
char = c;code = 99
char = y;code = 121
char = t;code = 116
char = o;code = 111
char = t;code = 116
char = o;code = 111
char = x;code = 120
char = i;code = 105
char = c;code = 99
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = h;code = 104
char = u;code = 117
char = m;code = 109
char = a;code = 97
char = n;code = 110
char = ;code = 32
char = m;code = 109
char = a;code = 97
char = l;code = 108
char = i;code = 105
char = g;code = 103
char = n;code = 110
char = a;code = 97
char = n;code = 110
char = t;code = 116
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = n;code = 110
char = o;code = 111
char = n;code = 110
char = m;code = 109
char = a;code = 97
char = l;code = 108
char = i;code = 105
char = g;code = 103
char = n;code = 110
char = a;code = 97
char = n;code = 110
char = t;code = 116
char = ;code = 32
char = b;code = 98
char = r;code = 114
char = e;code = 101
char = a;code = 97
char = s;code = 115
char = t;code = 116
char = ;code = 32
char = c;code = 99
char = a;code = 97
char = n;code = 110
char = c;code = 99
char = e;code = 101
char = r;code = 114
char = ;code = 32
char = c;code = 99
char = e;code = 101
char = l;code = 108
char = l;code = 108
char = ;code = 32
char = l;code = 108
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = s;code = 115
char = .;code = 46
char = ;code = 32
char = H;code = 72
char = o;code = 111
char = w;code = 119
char = e;code = 101
char = v;code = 118
char = e;code = 101
char = r;code = 114
char = ,;code = 44
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = v;code = 118
char = i;code = 105
char = t;code = 116
char = r;code = 114
char = o;code = 111
char = ;code = 32
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = m;code = 109
char = e;code = 101
char = t;code = 116
char = a;code = 97
char = b;code = 98
char = o;code = 111
char = l;code = 108
char = i;code = 105
char = t;code = 116
char = e;code = 101
char = s;code = 115
char = ;code = 32
char = m;code = 109
char = a;code = 97
char = y;code = 121
char = ;code = 32
char = n;code = 110
char = o;code = 111
char = t;code = 116
char = ;code = 32
char = n;code = 110
char = e;code = 101
char = c;code = 99
char = e;code = 101
char = s;code = 115
char = s;code = 115
char = a;code = 97
char = r;code = 114
char = i;code = 105
char = l;code = 108
char = y;code = 121
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = f;code = 102
char = l;code = 108
char = e;code = 101
char = c;code = 99
char = t;code = 116
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = i;code = 105
char = r;code = 114
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = v;code = 118
char = i;code = 105
char = v;code = 118
char = o;code = 111
char = ;code = 32
char = f;code = 102
char = u;code = 117
char = n;code = 110
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ,;code = 44
char = ;code = 32
char = g;code = 103
char = i;code = 105
char = v;code = 118
char = e;code = 101
char = n;code = 110
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = f;code = 102
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = a;code = 97
char = t;code = 116
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = u;code = 117
char = b;code = 98
char = i;code = 105
char = q;code = 113
char = u;code = 117
char = i;code = 105
char = t;code = 116
char = o;code = 111
char = u;code = 117
char = s;code = 115
char = l;code = 108
char = y;code = 121
char = ;code = 32
char = e;code = 101
char = x;code = 120
char = i;code = 105
char = s;code = 115
char = t;code = 116
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = h;code = 104
char = u;code = 117
char = m;code = 109
char = a;code = 97
char = n;code = 110
char = ;code = 32
char = s;code = 115
char = u;code = 117
char = l;code = 108
char = f;code = 102
char = a;code = 97
char = t;code = 116
char = a;code = 97
char = s;code = 115
char = e;code = 101
char = s;code = 115
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = u;code = 117
char = l;code = 108
char = d;code = 100
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = v;code = 118
char = e;code = 101
char = r;code = 114
char = t;code = 116
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = m;code = 109
char = e;code = 101
char = t;code = 116
char = a;code = 97
char = b;code = 98
char = o;code = 111
char = l;code = 108
char = i;code = 105
char = t;code = 116
char = e;code = 101
char = s;code = 115
char = ;code = 32
char = b;code = 98
char = a;code = 97
char = c;code = 99
char = k;code = 107
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = v;code = 118
char = e;code = 101
char = r;code = 114
char = a;code = 97
char = t;code = 116
char = r;code = 114
char = o;code = 111
char = l;code = 108
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = h;code = 104
char = u;code = 117
char = m;code = 109
char = a;code = 97
char = n;code = 110
char = s;code = 115
char = .;code = 46
char = <;code = 60
char = b;code = 98
char = r;code = 114
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result sql = Resveratrol (3,4',5-trihydroxy- trans-stilbene) is a naturally occurring polyphenolic compound found in grapes, wine and medicinal plants with a variety of biological and pharmacological activities including pronounced anticancer properties. These effects are observed despite its extremely low bioavailability and rapid clearance from the circulation due to extensive sulfation and glucuronidation in the intestine and liver. In order to determine whether its metabolites demonstrate any cytotoxic properties, three major human sulfated conjugates of resveratrol were synthesized and their anticancer activity evaluated against three breast cancer cell lines (two hormone-dependent: MCF-7 and ZR-75-1; one hormone-independent: MDA-MB-231) and one immortalized breast epithelial cell line (MCF-10A). We found that, in contrast to resveratrol, all three sulfated metabolites were less potent against MCF-7, MDA-MB-231 and ZR-75-1 cells ( trans-resveratrol 3- O-sulfate < trans-resveratrol 4'- O-sulfate < trans-resveratrol 3- O-4'- O-disulfate) indicating that any conjugation of the phenolic groups with sulfuric acid strongly affecting the cytotoxicity. Interestingly, all sulfated metabolites were reduced about 10-fold, but showed nearly equal cytotoxicity towards nonmalignant MCF-10A breast cells (IC (50 s): 202-228 microM). In summary, in contrast to resveratrol its sulfated metabolites showed poor cytotoxicity in human malignant and nonmalignant breast cancer cell lines. However, the in vitro activity of the metabolites may not necessarily reflect their in vivo function, given the fact that the ubiquitously existing human sulfatases could convert the metabolites back to resveratrol in humans.
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result sql = Antitumor activity of resveratrol and its sulfated metabolites against human breast cancer cells.
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char = s;code = 115
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char = -;code = 45
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char = 3;code = 51
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char = Z;code = 90
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char = 1;code = 49
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char = t;code = 116
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char = a;code = 97
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char = s;code = 115
char = v;code = 118
char = e;code = 101
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char = a;code = 97
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char = o;code = 111
char = l;code = 108
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char = O;code = 79
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char = s;code = 115
char = u;code = 117
char = l;code = 108
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char = a;code = 97
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char = s;code = 115
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char = e;code = 101
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char = a;code = 97
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char = r;code = 114
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char = l;code = 108
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char = 4;code = 52
char = ';code = 39
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char = O;code = 79
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char = s;code = 115
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char = l;code = 108
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char = a;code = 97
char = t;code = 116
char = e;code = 101
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char = t;code = 116
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char = a;code = 97
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char = a;code = 97
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char = o;code = 111
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char = O;code = 79
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char = 4;code = 52
char = ';code = 39
char = -;code = 45
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char = O;code = 79
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char = a;code = 97
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char = f;code = 102
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char = M;code = 77
char = C;code = 67
char = F;code = 70
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result sql = Resveratrol (3,4',5-trihydroxy- trans-stilbene) is a naturally occurring polyphenolic compound found in grapes, wine and medicinal plants with a variety of biological and pharmacological activities including pronounced anticancer properties. These effects are observed despite its extremely low bioavailability and rapid clearance from the circulation due to extensive sulfation and glucuronidation in the intestine and liver. In order to determine whether its metabolites demonstrate any cytotoxic properties, three major human sulfated conjugates of resveratrol were synthesized and their anticancer activity evaluated against three breast cancer cell lines (two hormone-dependent: MCF-7 and ZR-75-1; one hormone-independent: MDA-MB-231) and one immortalized breast epithelial cell line (MCF-10A). We found that, in contrast to resveratrol, all three sulfated metabolites were less potent against MCF-7, MDA-MB-231 and ZR-75-1 cells ( trans-resveratrol 3- O-sulfate < trans-resveratrol 4'- O-sulfate < trans-resveratrol 3- O-4'- O-disulfate) indicating that any conjugation of the phenolic groups with sulfuric acid strongly affecting the cytotoxicity. Interestingly, all sulfated metabolites were reduced about 10-fold, but showed nearly equal cytotoxicity towards nonmalignant MCF-10A breast cells (IC (50 s): 202-228 microM). In summary, in contrast to resveratrol its sulfated metabolites showed poor cytotoxicity in human malignant and nonmalignant breast cancer cell lines. However, the in vitro activity of the metabolites may not necessarily reflect their in vivo function, given the fact that the ubiquitously existing human sulfatases could convert the metabolites back to resveratrol in humans.
Publication: Planta Med. 2009 Sep ;75(11)::1227-30. :doi: 10.1055/s-0029-1185533.
Publication Date: 2009 Sep
Study Author(s): Miksits, Michaela;Wlcek, Katrin;Svoboda, Martin;Kunert, Olaf;Haslinger, Ernst;Thalhammer, Theresia;Szekeres, Thomas;Jäger, Walter;
Institution: Department of Clinical Pharmacy and Diagnostics, University of Vienna, Vienna, Austria.
Shortcut link to this study:
Publication Date: 2009 Sep
Study Author(s): Miksits, Michaela;Wlcek, Katrin;Svoboda, Martin;Kunert, Olaf;Haslinger, Ernst;Thalhammer, Theresia;Szekeres, Thomas;Jäger, Walter;
Institution: Department of Clinical Pharmacy and Diagnostics, University of Vienna, Vienna, Austria.
Shortcut link to this study:
Resveratrol (3,4',5-trihydroxy- trans-stilbene) is a naturally occurring polyphenolic compound found in grapes, wine and medicinal plants with a variety of biological and pharmacological activities including pronounced anticancer properties. These effects are observed despite its extremely low bioavailability and rapid clearance from the circulation due to extensive sulfation and glucuronidation in the intestine and liver. In order to determine whether its metabolites demonstrate any cytotoxic properties, three major human sulfated conjugates of resveratrol were synthesized and their anticancer activity evaluated against three breast cancer cell lines (two hormone-dependent: MCF-7 and ZR-75-1; one hormone-independent: MDA-MB-231) and one immortalized breast epithelial cell line (MCF-10A). We found that, in contrast to resveratrol, all three sulfated metabolites were less potent against MCF-7, MDA-MB-231 and ZR-75-1 cells ( trans-resveratrol 3- O-sulfate < trans-resveratrol 4'- O-sulfate < trans-resveratrol 3- O-4'- O-disulfate) indicating that any conjugation of the phenolic groups with sulfuric acid strongly affecting the cytotoxicity. Interestingly, all sulfated metabolites were reduced about 10-fold, but showed nearly equal cytotoxicity towards nonmalignant MCF-10A breast cells (IC (50 s): 202-228 microM). In summary, in contrast to resveratrol its sulfated metabolites showed poor cytotoxicity in human malignant and nonmalignant breast cancer cell lines. However, the in vitro activity of the metabolites may not necessarily reflect their in vivo function, given the fact that the ubiquitously existing human sulfatases could convert the metabolites back to resveratrol in humans.
PMID: 19350482
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