char = P;code = 80
char = i;code = 105
char = m;code = 109
char = a;code = 97
char = r;code = 114
char = a;code = 97
char = n;code = 110
char = e;code = 101
char = -;code = 45
char = t;code = 116
char = y;code = 121
char = p;code = 112
char = e;code = 101
char = ;code = 32
char = d;code = 100
char = i;code = 105
char = t;code = 116
char = e;code = 101
char = r;code = 114
char = p;code = 112
char = e;code = 101
char = n;code = 110
char = e;code = 101
char = s;code = 115
char = :;code = 58
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = t;code = 116
char = i;code = 105
char = m;code = 109
char = i;code = 105
char = c;code = 99
char = r;code = 114
char = o;code = 111
char = b;code = 98
char = i;code = 105
char = a;code = 97
char = l;code = 108
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 = 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 = o;code = 111
char = r;code = 114
char = a;code = 97
char = l;code = 108
char = ;code = 32
char = p;code = 112
char = a;code = 97
char = t;code = 116
char = h;code = 104
char = o;code = 111
char = g;code = 103
char = e;code = 101
char = n;code = 110
char = s;code = 115
char = .;code = 46
result sql = Pimarane-type diterpenes: antimicrobial activity against oral pathogens.
Pimarane-type diterpenes: antimicrobial activity against oral pathogens.
char = <;code = 60
char = b;code = 98
char = >;code = 62
char = S;code = 83
char = E;code = 69
char = V;code = 86
char = E;code = 69
char = N;code = 78
char = ;code = 32
char = P;code = 80
char = I;code = 73
char = M;code = 77
char = A;code = 65
char = R;code = 82
char = A;code = 65
char = N;code = 78
char = E;code = 69
char = ;code = 32
char = T;code = 84
char = Y;code = 89
char = P;code = 80
char = E;code = 69
char = -;code = 45
char = D;code = 68
char = I;code = 73
char = T;code = 84
char = E;code = 69
char = R;code = 82
char = P;code = 80
char = E;code = 69
char = N;code = 78
char = E;code = 69
char = S;code = 83
char = ;code = 32
char = R;code = 82
char = E;code = 69
char = -;code = 45
char = I;code = 73
char = S;code = 83
char = O;code = 79
char = L;code = 76
char = A;code = 65
char = T;code = 84
char = E;code = 69
char = D;code = 68
char = ;code = 32
char = F;code = 70
char = R;code = 82
char = O;code = 79
char = M;code = 77
char = ;code = 32
char = V;code = 86
char = I;code = 73
char = G;code = 71
char = U;code = 85
char = I;code = 73
char = E;code = 69
char = R;code = 82
char = A;code = 65
char = ;code = 32
char = A;code = 65
char = R;code = 82
char = E;code = 69
char = N;code = 78
char = A;code = 65
char = R;code = 82
char = I;code = 73
char = A;code = 65
char = ;code = 32
char = B;code = 66
char = A;code = 65
char = K;code = 75
char = E;code = 69
char = R;code = 82
char = ;code = 32
char = A;code = 65
char = N;code = 78
char = D;code = 68
char = ;code = 32
char = T;code = 84
char = W;code = 87
char = O;code = 79
char = ;code = 32
char = S;code = 83
char = E;code = 69
char = M;code = 77
char = I;code = 73
char = -;code = 45
char = S;code = 83
char = Y;code = 89
char = N;code = 78
char = T;code = 84
char = H;code = 72
char = E;code = 69
char = T;code = 84
char = I;code = 73
char = C;code = 67
char = ;code = 32
char = P;code = 80
char = I;code = 73
char = M;code = 77
char = A;code = 65
char = R;code = 82
char = A;code = 65
char = N;code = 78
char = E;code = 69
char = ;code = 32
char = D;code = 68
char = E;code = 69
char = R;code = 82
char = I;code = 73
char = V;code = 86
char = A;code = 65
char = T;code = 84
char = I;code = 73
char = V;code = 86
char = E;code = 69
char = S;code = 83
char = ;code = 32
char = W;code = 87
char = E;code = 69
char = R;code = 82
char = E;code = 69
char = ;code = 32
char = E;code = 69
char = V;code = 86
char = A;code = 65
char = L;code = 76
char = U;code = 85
char = A;code = 65
char = T;code = 84
char = E;code = 69
char = D;code = 68
char = ;code = 32
char = I;code = 73
char = N;code = 78
char = ;code = 32
char = V;code = 86
char = I;code = 73
char = T;code = 84
char = R;code = 82
char = O;code = 79
char = ;code = 32
char = A;code = 65
char = G;code = 71
char = A;code = 65
char = I;code = 73
char = N;code = 78
char = S;code = 83
char = T;code = 84
char = ;code = 32
char = T;code = 84
char = H;code = 72
char = E;code = 69
char = ;code = 32
char = F;code = 70
char = O;code = 79
char = L;code = 76
char = L;code = 76
char = O;code = 79
char = W;code = 87
char = I;code = 73
char = N;code = 78
char = G;code = 71
char = ;code = 32
char = M;code = 77
char = A;code = 65
char = I;code = 73
char = N;code = 78
char = ;code = 32
char = M;code = 77
char = I;code = 73
char = C;code = 67
char = R;code = 82
char = O;code = 79
char = O;code = 79
char = R;code = 82
char = G;code = 71
char = A;code = 65
char = N;code = 78
char = I;code = 73
char = S;code = 83
char = M;code = 77
char = S;code = 83
char = ;code = 32
char = R;code = 82
char = E;code = 69
char = S;code = 83
char = P;code = 80
char = O;code = 79
char = N;code = 78
char = S;code = 83
char = I;code = 73
char = B;code = 66
char = L;code = 76
char = E;code = 69
char = ;code = 32
char = F;code = 70
char = O;code = 79
char = R;code = 82
char = ;code = 32
char = D;code = 68
char = E;code = 69
char = N;code = 78
char = T;code = 84
char = A;code = 65
char = L;code = 76
char = ;code = 32
char = C;code = 67
char = A;code = 65
char = R;code = 82
char = I;code = 73
char = E;code = 69
char = S;code = 83
char = :;code = 58
char = ;code = 32
char = <;code = 60
char = /;code = 47
char = b;code = 98
char = >;code = 62
char = ;code = 32
char = S;code = 83
char = t;code = 116
char = r;code = 114
char = e;code = 101
char = p;code = 112
char = t;code = 116
char = o;code = 111
char = c;code = 99
char = o;code = 111
char = c;code = 99
char = c;code = 99
char = u;code = 117
char = s;code = 115
char = ;code = 32
char = s;code = 115
char = a;code = 97
char = l;code = 108
char = i;code = 105
char = v;code = 118
char = a;code = 97
char = r;code = 114
char = i;code = 105
char = u;code = 117
char = s;code = 115
char = ,;code = 44
char = ;code = 32
char = S;code = 83
char = .;code = 46
char = ;code = 32
char = s;code = 115
char = o;code = 111
char = b;code = 98
char = r;code = 114
char = i;code = 105
char = n;code = 110
char = u;code = 117
char = s;code = 115
char = ,;code = 44
char = ;code = 32
char = S;code = 83
char = .;code = 46
char = ;code = 32
char = m;code = 109
char = u;code = 117
char = t;code = 116
char = a;code = 97
char = n;code = 110
char = s;code = 115
char = ,;code = 44
char = ;code = 32
char = S;code = 83
char = .;code = 46
char = ;code = 32
char = m;code = 109
char = i;code = 105
char = t;code = 116
char = i;code = 105
char = s;code = 115
char = ,;code = 44
char = ;code = 32
char = S;code = 83
char = .;code = 46
char = ;code = 32
char = s;code = 115
char = a;code = 97
char = n;code = 110
char = g;code = 103
char = u;code = 117
char = i;code = 105
char = n;code = 110
char = i;code = 105
char = s;code = 115
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = L;code = 76
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = o;code = 111
char = b;code = 98
char = a;code = 97
char = c;code = 99
char = i;code = 105
char = l;code = 108
char = l;code = 108
char = u;code = 117
char = s;code = 115
char = ;code = 32
char = c;code = 99
char = a;code = 97
char = s;code = 115
char = e;code = 101
char = i;code = 105
char = .;code = 46
char = ;code = 32
char = T;code = 84
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = m;code = 109
char = p;code = 112
char = o;code = 111
char = u;code = 117
char = n;code = 110
char = d;code = 100
char = s;code = 115
char = ;code = 32
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = -;code = 45
char = p;code = 112
char = i;code = 105
char = m;code = 109
char = a;code = 97
char = r;code = 114
char = a;code = 97
char = -;code = 45
char = 8;code = 56
char = (;code = 40
char = 1;code = 49
char = 4;code = 52
char = );code = 41
char = ,;code = 44
char = 1;code = 49
char = 5;code = 53
char = -;code = 45
char = d;code = 100
char = i;code = 105
char = e;code = 101
char = n;code = 110
char = -;code = 45
char = 1;code = 49
char = 9;code = 57
char = -;code = 45
char = o;code = 111
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 = (;code = 40
char = P;code = 80
char = A;code = 65
char = );code = 41
char = ;;code = 59
char = ;code = 32
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = -;code = 45
char = 8;code = 56
char = (;code = 40
char = 1;code = 49
char = 4;code = 52
char = );code = 41
char = ,;code = 44
char = 1;code = 49
char = 5;code = 53
char = -;code = 45
char = p;code = 112
char = i;code = 105
char = m;code = 109
char = a;code = 97
char = r;code = 114
char = a;code = 97
char = d;code = 100
char = i;code = 105
char = e;code = 101
char = n;code = 110
char = -;code = 45
char = 3;code = 51
char = b;code = 98
char = e;code = 101
char = t;code = 116
char = a;code = 97
char = -;code = 45
char = o;code = 111
char = l;code = 108
char = ;;code = 59
char = ;code = 32
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = -;code = 45
char = 1;code = 49
char = 5;code = 53
char = -;code = 45
char = p;code = 112
char = i;code = 105
char = m;code = 109
char = a;code = 97
char = r;code = 114
char = e;code = 101
char = n;code = 110
char = e;code = 101
char = -;code = 45
char = 8;code = 56
char = b;code = 98
char = e;code = 101
char = t;code = 116
char = a;code = 97
char = ,;code = 44
char = 1;code = 49
char = 9;code = 57
char = -;code = 45
char = d;code = 100
char = i;code = 105
char = o;code = 111
char = l;code = 108
char = ;;code = 59
char = ;code = 32
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = -;code = 45
char = 8;code = 56
char = (;code = 40
char = 1;code = 49
char = 4;code = 52
char = );code = 41
char = ,;code = 44
char = 1;code = 49
char = 5;code = 53
char = -;code = 45
char = p;code = 112
char = i;code = 105
char = m;code = 109
char = a;code = 97
char = r;code = 114
char = a;code = 97
char = d;code = 100
char = i;code = 105
char = e;code = 101
char = n;code = 110
char = -;code = 45
char = 3;code = 51
char = b;code = 98
char = e;code = 101
char = t;code = 116
char = a;code = 97
char = -;code = 45
char = a;code = 97
char = c;code = 99
char = e;code = 101
char = t;code = 116
char = o;code = 111
char = x;code = 120
char = y;code = 121
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = s;code = 115
char = o;code = 111
char = d;code = 100
char = i;code = 105
char = u;code = 117
char = m;code = 109
char = ;code = 32
char = s;code = 115
char = a;code = 97
char = l;code = 108
char = t;code = 116
char = ;code = 32
char = d;code = 100
char = e;code = 101
char = r;code = 114
char = i;code = 105
char = v;code = 118
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = e;code = 101
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = P;code = 80
char = A;code = 65
char = ;code = 32
char = w;code = 119
char = e;code = 101
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = m;code = 109
char = o;code = 111
char = s;code = 115
char = t;code = 116
char = ;code = 32
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = e;code = 101
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = m;code = 109
char = p;code = 112
char = o;code = 111
char = u;code = 117
char = n;code = 110
char = d;code = 100
char = s;code = 115
char = ,;code = 44
char = ;code = 32
char = d;code = 100
char = i;code = 105
char = s;code = 115
char = p;code = 112
char = l;code = 108
char = a;code = 97
char = y;code = 121
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = M;code = 77
char = I;code = 73
char = C;code = 67
char = ;code = 32
char = v;code = 118
char = a;code = 97
char = l;code = 108
char = u;code = 117
char = e;code = 101
char = s;code = 115
char = ;code = 32
char = r;code = 114
char = a;code = 97
char = n;code = 110
char = g;code = 103
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = f;code = 102
char = r;code = 114
char = o;code = 111
char = m;code = 109
char = ;code = 32
char = 2;code = 50
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
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 = g;code = 103
char = ;code = 32
char = m;code = 109
char = L;code = 76
char = (;code = 40
char = -;code = 45
char = 1;code = 49
char = );code = 41
char = .;code = 46
char = ;code = 32
char = T;code = 84
char = h;code = 104
char = u;code = 117
char = s;code = 115
char = ,;code = 44
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = i;code = 105
char = s;code = 115
char = ;code = 32
char = c;code = 99
char = l;code = 108
char = a;code = 97
char = s;code = 115
char = s;code = 115
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = m;code = 109
char = p;code = 112
char = o;code = 111
char = u;code = 117
char = n;code = 110
char = d;code = 100
char = s;code = 115
char = ;code = 32
char = s;code = 115
char = e;code = 101
char = e;code = 101
char = m;code = 109
char = s;code = 115
char = ;code = 32
char = p;code = 112
char = r;code = 114
char = o;code = 111
char = m;code = 109
char = i;code = 105
char = s;code = 115
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = a;code = 97
char = s;code = 115
char = ;code = 32
char = a;code = 97
char = ;code = 32
char = c;code = 99
char = l;code = 108
char = a;code = 97
char = s;code = 115
char = s;code = 115
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = n;code = 110
char = e;code = 101
char = w;code = 119
char = ;code = 32
char = e;code = 101
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 = v;code = 118
char = e;code = 101
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = t;code = 116
char = i;code = 105
char = c;code = 99
char = a;code = 97
char = r;code = 114
char = i;code = 105
char = o;code = 111
char = g;code = 103
char = e;code = 101
char = n;code = 110
char = i;code = 105
char = c;code = 99
char = ;code = 32
char = a;code = 97
char = g;code = 103
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = s;code = 115
char = .;code = 46
char = ;code = 32
char = F;code = 70
char = u;code = 117
char = r;code = 114
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = r;code = 114
char = m;code = 109
char = o;code = 111
char = r;code = 114
char = e;code = 101
char = ,;code = 44
char = ;code = 32
char = o;code = 111
char = u;code = 117
char = r;code = 114
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = u;code = 117
char = l;code = 108
char = t;code = 116
char = s;code = 115
char = ;code = 32
char = a;code = 97
char = l;code = 108
char = s;code = 115
char = o;code = 111
char = ;code = 32
char = a;code = 97
char = l;code = 108
char = l;code = 108
char = o;code = 111
char = w;code = 119
char = ;code = 32
char = u;code = 117
char = s;code = 115
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = c;code = 99
char = l;code = 108
char = u;code = 117
char = d;code = 100
char = e;code = 101
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = a;code = 97
char = t;code = 116
char = ;code = 32
char = m;code = 109
char = i;code = 105
char = n;code = 110
char = o;code = 111
char = r;code = 114
char = ;code = 32
char = s;code = 115
char = t;code = 116
char = r;code = 114
char = u;code = 117
char = c;code = 99
char = t;code = 116
char = u;code = 117
char = r;code = 114
char = a;code = 97
char = l;code = 108
char = ;code = 32
char = d;code = 100
char = i;code = 105
char = f;code = 102
char = f;code = 102
char = e;code = 101
char = r;code = 114
char = e;code = 101
char = n;code = 110
char = c;code = 99
char = e;code = 101
char = s;code = 115
char = ;code = 32
char = a;code = 97
char = m;code = 109
char = o;code = 111
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = s;code = 115
char = e;code = 101
char = ;code = 32
char = d;code = 100
char = i;code = 105
char = t;code = 116
char = e;code = 101
char = r;code = 114
char = p;code = 112
char = e;code = 101
char = n;code = 110
char = e;code = 101
char = s;code = 115
char = ;code = 32
char = s;code = 115
char = i;code = 105
char = g;code = 103
char = n;code = 110
char = i;code = 105
char = f;code = 102
char = i;code = 105
char = c;code = 99
char = a;code = 97
char = n;code = 110
char = t;code = 116
char = l;code = 108
char = y;code = 121
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = f;code = 102
char = l;code = 108
char = u;code = 117
char = e;code = 101
char = n;code = 110
char = c;code = 99
char = e;code = 101
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 = a;code = 97
char = n;code = 110
char = t;code = 116
char = i;code = 105
char = m;code = 109
char = i;code = 105
char = c;code = 99
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result sql = SEVEN PIMARANE TYPE-DITERPENES RE-ISOLATED FROM VIGUIERA ARENARIA BAKER AND TWO SEMI-SYNTHETIC PIMARANE DERIVATIVES WERE EVALUATED IN VITRO AGAINST THE FOLLOWING MAIN MICROORGANISMS RESPONSIBLE FOR DENTAL CARIES: Streptococcus salivarius, S. sobrinus, S. mutans, S. mitis, S. sanguinis and Lactobacillus casei. The compounds ent-pimara-8(14),15-dien-19-oic acid (PA); ent-8(14),15-pimaradien-3beta-ol; ent-15-pimarene-8beta,19-diol; ent-8(14),15-pimaradien-3beta-acetoxy and the sodium salt derivative of PA were the most active compounds, displaying MIC values ranging from 2 to 8 microg mL(-1). Thus, this class of compounds seems promising as a class of new effective anticariogenic agents. Furthermore, our results also allow us to conclude that minor structural differences among these diterpenes significantly influence their antimicrobial activity, bringing new perspectives to the discovery of new natural compounds that could be employed in the development of oral care products.

Publication: Molecules 2009 ;14(1)::191-9. :doi: 10.3390/molecules14010191.
Publication Date: 2009
Study Author(s): Porto, Thiago S;Rangel, Rander;Furtado, Niege A J C;de Carvalho, Tatiane C;Martins, Carlos H G;Veneziani, Rodrigo C S;Da Costa, Fernando B;Vinholis, Adriana H C;Cunha, Wilson R;Heleno, Vladimir C G;Ambrosio, Sergio R;
Institution: Núcleo de Pesquisa em Ciências Exatas e Tecnológicas, Universidade de Franca, Franca, SP, Brazil.
Shortcut link to this study:
SEVEN PIMARANE TYPE-DITERPENES RE-ISOLATED FROM VIGUIERA ARENARIA BAKER AND TWO SEMI-SYNTHETIC PIMARANE DERIVATIVES WERE EVALUATED IN VITRO AGAINST THE FOLLOWING MAIN MICROORGANISMS RESPONSIBLE FOR DENTAL CARIES: Streptococcus salivarius, S. sobrinus, S. mutans, S. mitis, S. sanguinis and Lactobacillus casei. The compounds ent-pimara-8(14),15-dien-19-oic acid (PA); ent-8(14),15-pimaradien-3beta-ol; ent-15-pimarene-8beta,19-diol; ent-8(14),15-pimaradien-3beta-acetoxy and the sodium salt derivative of PA were the most active compounds, displaying MIC values ranging from 2 to 8 microg mL(-1). Thus, this class of compounds seems promising as a class of new effective anticariogenic agents. Furthermore, our results also allow us to conclude that minor structural differences among these diterpenes significantly influence their antimicrobial activity, bringing new perspectives to the discovery of new natural compounds that could be employed in the development of oral care products.
PMID: 19127247

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