char = A;code = 65
char = n;code = 110
char = ;code = 32
char = u;code = 117
char = n;code = 110
char = u;code = 117
char = s;code = 115
char = u;code = 117
char = a;code = 97
char = l;code = 108
char = ;code = 32
char = d;code = 100
char = i;code = 105
char = m;code = 109
char = e;code = 101
char = r;code = 114
char = i;code = 105
char = c;code = 99
char = ;code = 32
char = g;code = 103
char = u;code = 117
char = a;code = 97
char = i;code = 105
char = a;code = 97
char = n;code = 110
char = o;code = 111
char = l;code = 108
char = i;code = 105
char = d;code = 100
char = e;code = 101
char = ;code = 32
char = w;code = 119
char = i;code = 105
char = t;code = 116
char = h;code = 104
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = t;code = 116
char = i;code = 105
char = p;code = 112
char = r;code = 114
char = o;code = 111
char = t;code = 116
char = o;code = 111
char = z;code = 122
char = o;code = 111
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 = n;code = 110
char = d;code = 100
char = ;code = 32
char = f;code = 102
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 = ;code = 32
char = s;code = 115
char = e;code = 101
char = s;code = 115
char = q;code = 113
char = u;code = 117
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 = ;code = 32
char = l;code = 108
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = o;code = 111
char = n;code = 110
char = e;code = 101
char = s;code = 115
char = ;code = 32
char = f;code = 102
char = r;code = 114
char = o;code = 111
char = m;code = 109
char = ;code = 32
char = E;code = 69
char = u;code = 117
char = p;code = 112
char = a;code = 97
char = t;code = 116
char = o;code = 111
char = r;code = 114
char = i;code = 105
char = u;code = 117
char = m;code = 109
char = p;code = 112
char = e;code = 101
char = r;code = 114
char = f;code = 102
char = o;code = 111
char = l;code = 108
char = i;code = 105
char = a;code = 97
char = t;code = 116
char = u;code = 117
char = m;code = 109
char = .;code = 46
result sql = An unusual dimeric guaianolide with antiprotozoal activity and further sesquiterpene lactones from Eupatoriumperfoliatum.
An unusual dimeric guaianolide with antiprotozoal activity and further sesquiterpene lactones from Eupatoriumperfoliatum.
char = T;code = 84
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = C;code = 67
char = H;code = 72
char = (;code = 40
char = 2;code = 50
char = );code = 41
char = C;code = 67
char = l;code = 108
char = (;code = 40
char = 2;code = 50
char = );code = 41
char = ;code = 32
char = e;code = 101
char = x;code = 120
char = t;code = 116
char = r;code = 114
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = a;code = 97
char = e;code = 101
char = r;code = 114
char = i;code = 105
char = a;code = 97
char = l;code = 108
char = ;code = 32
char = p;code = 112
char = a;code = 97
char = r;code = 114
char = t;code = 116
char = s;code = 115
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = E;code = 69
char = u;code = 117
char = p;code = 112
char = a;code = 97
char = t;code = 116
char = o;code = 111
char = r;code = 114
char = i;code = 105
char = u;code = 117
char = m;code = 109
char = ;code = 32
char = p;code = 112
char = e;code = 101
char = r;code = 114
char = f;code = 102
char = o;code = 111
char = l;code = 108
char = i;code = 105
char = a;code = 97
char = t;code = 116
char = u;code = 117
char = m;code = 109
char = ;code = 32
char = L;code = 76
char = .;code = 46
char = ;code = 32
char = e;code = 101
char = x;code = 120
char = h;code = 104
char = i;code = 105
char = b;code = 98
char = i;code = 105
char = t;code = 116
char = s;code = 115
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = t;code = 116
char = i;code = 105
char = p;code = 112
char = r;code = 114
char = o;code = 111
char = t;code = 116
char = o;code = 111
char = z;code = 122
char = o;code = 111
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 = u;code = 117
char = n;code = 110
char = d;code = 100
char = e;code = 101
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 = t;code = 116
char = r;code = 114
char = o;code = 111
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = d;code = 100
char = i;code = 105
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = s;code = 115
char = ,;code = 44
char = ;code = 32
char = e;code = 101
char = s;code = 115
char = p;code = 112
char = e;code = 101
char = c;code = 99
char = i;code = 105
char = a;code = 97
char = l;code = 108
char = l;code = 108
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 = P;code = 80
char = l;code = 108
char = a;code = 97
char = s;code = 115
char = m;code = 109
char = o;code = 111
char = d;code = 100
char = i;code = 105
char = u;code = 117
char = m;code = 109
char = ;code = 32
char = f;code = 102
char = a;code = 97
char = l;code = 108
char = c;code = 99
char = i;code = 105
char = p;code = 112
char = a;code = 97
char = r;code = 114
char = u;code = 117
char = m;code = 109
char = ;code = 32
char = (;code = 40
char = I;code = 73
char = C;code = 67
char = (;code = 40
char = 5;code = 53
char = 0;code = 48
char = );code = 41
char = =;code = 61
char = 2;code = 50
char = .;code = 46
char = 7;code = 55
char = &;code = 38
char = #;code = 35
char = 9;code = 57
char = 5;code = 53
char = 6;code = 54
char = ;;code = 59
char = g;code = 103
char = /;code = 47
char = m;code = 109
char = l;code = 108
char = );code = 41
char = .;code = 46
char = ;code = 32
char = <;code = 60
char = b;code = 98
char = >;code = 62
char = T;code = 84
char = H;code = 72
char = E;code = 69
char = ;code = 32
char = S;code = 83
char = E;code = 69
char = A;code = 65
char = R;code = 82
char = C;code = 67
char = H;code = 72
char = ;code = 32
char = F;code = 70
char = O;code = 79
char = R;code = 82
char = ;code = 32
char = A;code = 65
char = C;code = 67
char = T;code = 84
char = I;code = 73
char = V;code = 86
char = E;code = 69
char = ;code = 32
char = C;code = 67
char = O;code = 79
char = M;code = 77
char = P;code = 80
char = O;code = 79
char = U;code = 85
char = N;code = 78
char = D;code = 68
char = S;code = 83
char = ;code = 32
char = Y;code = 89
char = I;code = 73
char = E;code = 69
char = L;code = 76
char = D;code = 68
char = E;code = 69
char = D;code = 68
char = ;code = 32
char = S;code = 83
char = E;code = 69
char = V;code = 86
char = E;code = 69
char = N;code = 78
char = ;code = 32
char = S;code = 83
char = E;code = 69
char = S;code = 83
char = Q;code = 81
char = U;code = 85
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 = ;code = 32
char = L;code = 76
char = A;code = 65
char = C;code = 67
char = T;code = 84
char = O;code = 79
char = N;code = 78
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 = F;code = 70
char = o;code = 111
char = u;code = 117
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 = l;code = 108
char = y;code = 121
char = ;code = 32
char = s;code = 115
char = i;code = 105
char = m;code = 109
char = i;code = 105
char = l;code = 108
char = a;code = 97
char = r;code = 114
char = ;code = 32
char = g;code = 103
char = u;code = 117
char = a;code = 97
char = i;code = 105
char = a;code = 97
char = n;code = 110
char = o;code = 111
char = l;code = 108
char = i;code = 105
char = d;code = 100
char = e;code = 101
char = s;code = 115
char = ,;code = 44
char = ;code = 32
char = o;code = 111
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = d;code = 100
char = i;code = 105
char = m;code = 109
char = e;code = 101
char = r;code = 114
char = i;code = 105
char = c;code = 99
char = ;code = 32
char = g;code = 103
char = u;code = 117
char = a;code = 97
char = i;code = 105
char = a;code = 97
char = n;code = 110
char = o;code = 111
char = l;code = 108
char = i;code = 105
char = d;code = 100
char = e;code = 101
char = ,;code = 44
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = t;code = 116
char = w;code = 119
char = o;code = 111
char = ;code = 32
char = g;code = 103
char = e;code = 101
char = r;code = 114
char = m;code = 109
char = a;code = 97
char = c;code = 99
char = r;code = 114
char = a;code = 97
char = n;code = 110
char = o;code = 111
char = l;code = 108
char = i;code = 105
char = d;code = 100
char = e;code = 101
char = s;code = 115
char = .;code = 46
char = ;code = 32
char = T;code = 84
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = g;code = 103
char = u;code = 117
char = a;code = 97
char = i;code = 105
char = a;code = 97
char = n;code = 110
char = o;code = 111
char = l;code = 108
char = i;code = 105
char = d;code = 100
char = e;code = 101
char = s;code = 115
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 = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = d;code = 100
char = e;code = 101
char = g;code = 103
char = r;code = 114
char = e;code = 101
char = e;code = 101
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = o;code = 111
char = x;code = 120
char = i;code = 105
char = d;code = 100
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = a;code = 97
char = t;code = 116
char = ;code = 32
char = C;code = 67
char = -;code = 45
char = 1;code = 49
char = 4;code = 52
char = ,;code = 44
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 = a;code = 97
char = ;code = 32
char = h;code = 104
char = y;code = 121
char = d;code = 100
char = r;code = 114
char = o;code = 111
char = x;code = 120
char = y;code = 121
char = l;code = 108
char = ;code = 32
char = g;code = 103
char = r;code = 114
char = o;code = 111
char = u;code = 117
char = p;code = 112
char = ;code = 32
char = u;code = 117
char = p;code = 112
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = a;code = 97
char = ;code = 32
char = f;code = 102
char = r;code = 114
char = e;code = 101
char = e;code = 101
char = ;code = 32
char = c;code = 99
char = a;code = 97
char = r;code = 114
char = b;code = 98
char = o;code = 111
char = x;code = 120
char = y;code = 121
char = l;code = 108
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 = 46
char = ;code = 32
char = T;code = 84
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = d;code = 100
char = i;code = 105
char = m;code = 109
char = e;code = 101
char = r;code = 114
char = i;code = 105
char = c;code = 99
char = ;code = 32
char = g;code = 103
char = u;code = 117
char = a;code = 97
char = i;code = 105
char = a;code = 97
char = n;code = 110
char = o;code = 111
char = l;code = 108
char = i;code = 105
char = d;code = 100
char = e;code = 101
char = ,;code = 44
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 = l;code = 108
char = y;code = 121
char = ;code = 32
char = c;code = 99
char = l;code = 108
char = o;code = 111
char = s;code = 115
char = e;code = 101
char = l;code = 108
char = y;code = 121
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = l;code = 108
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = t;code = 116
char = o;code = 111
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 = n;code = 110
char = o;code = 111
char = m;code = 109
char = e;code = 101
char = r;code = 114
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 = s;code = 115
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = ;code = 32
char = u;code = 117
char = n;code = 110
char = u;code = 117
char = s;code = 115
char = u;code = 117
char = a;code = 97
char = l;code = 108
char = ;code = 32
char = t;code = 116
char = y;code = 121
char = p;code = 112
char = e;code = 101
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char = o;code = 111
char = f;code = 102
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = t;code = 116
char = e;code = 101
char = r;code = 114
char = g;code = 103
char = u;code = 117
char = a;code = 97
char = i;code = 105
char = a;code = 97
char = n;code = 110
char = o;code = 111
char = l;code = 108
char = i;code = 105
char = d;code = 100
char = e;code = 101
char = ;code = 32
char = l;code = 108
char = i;code = 105
char = n;code = 110
char = k;code = 107
char = a;code = 97
char = g;code = 103
char = e;code = 101
char = ;code = 32
char = b;code = 98
char = e;code = 101
char = t;code = 116
char = w;code = 119
char = e;code = 101
char = e;code = 101
char = n;code = 110
char = ;code = 32
char = C;code = 67
char = -;code = 45
char = 1;code = 49
char = 4;code = 52
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = C;code = 67
char = -;code = 45
char = 4;code = 52
char = .;code = 46
char = ;code = 32
char = E;code = 69
char = x;code = 120
char = c;code = 99
char = e;code = 101
char = p;code = 112
char = t;code = 116
char = ;code = 32
char = f;code = 102
char = o;code = 111
char = r;code = 114
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = g;code = 103
char = e;code = 101
char = r;code = 114
char = m;code = 109
char = a;code = 97
char = c;code = 99
char = r;code = 114
char = a;code = 97
char = n;code = 110
char = o;code = 111
char = l;code = 108
char = i;code = 105
char = d;code = 100
char = e;code = 101
char = ;code = 32
char = e;code = 101
char = u;code = 117
char = p;code = 112
char = e;code = 101
char = r;code = 114
char = f;code = 102
char = o;code = 111
char = l;code = 108
char = i;code = 105
char = t;code = 116
char = i;code = 105
char = n;code = 110
char = ,;code = 44
char = ;code = 32
char = a;code = 97
char = l;code = 108
char = l;code = 108
char = ;code = 32
char = S;code = 83
char = T;code = 84
char = L;code = 76
char = s;code = 115
char = ;code = 32
char = d;code = 100
char = e;code = 101
char = s;code = 115
char = c;code = 99
char = r;code = 114
char = i;code = 105
char = b;code = 98
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = h;code = 104
char = e;code = 101
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = w;code = 119
char = e;code = 101
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = h;code = 104
char = i;code = 105
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = r;code = 114
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = u;code = 117
char = n;code = 110
char = k;code = 107
char = n;code = 110
char = o;code = 111
char = w;code = 119
char = n;code = 110
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 = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = f;code = 102
char = l;code = 108
char = a;code = 97
char = v;code = 118
char = o;code = 111
char = n;code = 110
char = o;code = 111
char = i;code = 105
char = d;code = 100
char = ;code = 32
char = a;code = 97
char = g;code = 103
char = l;code = 108
char = y;code = 121
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = e;code = 101
char = s;code = 115
char = ;code = 32
char = e;code = 101
char = u;code = 117
char = p;code = 112
char = a;code = 97
char = f;code = 102
char = o;code = 111
char = l;code = 108
char = i;code = 105
char = n;code = 110
char = ,;code = 44
char = ;code = 32
char = h;code = 104
char = i;code = 105
char = s;code = 115
char = p;code = 112
char = i;code = 105
char = d;code = 100
char = u;code = 117
char = l;code = 108
char = i;code = 105
char = n;code = 110
char = ,;code = 44
char = ;code = 32
char = p;code = 112
char = a;code = 97
char = t;code = 116
char = u;code = 117
char = l;code = 108
char = e;code = 101
char = t;code = 116
char = i;code = 105
char = n;code = 110
char = ,;code = 44
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
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result sql = The CH(2)Cl(2) extract of aerial parts of Eupatorium perfoliatum L. exhibits antiprotozoal activity under in vitro conditions, especially against Plasmodium falciparum (IC(50)=2.7μg/ml). THE SEARCH FOR ACTIVE COMPOUNDS YIELDED SEVEN SESQUITERPENE LACTONES: Four structurally similar guaianolides, one dimeric guaianolide, and two germacranolides. The guaianolides differ in the degree of oxidation at C-14, ranging from a hydroxyl group up to a free carboxylic acid. The dimeric guaianolide, structurally closely related to the monomers, displays an unusual type of interguaianolide linkage between C-14 and C-4. Except for the germacranolide euperfolitin, all STLs described here were hitherto unknown. Furthermore, the flavonoid aglycones eupafolin, hispidulin, patuletin, and kaempferol were identified in the extract, which, except for kaempferol, have not been described as constituents of E. perfoliatum before. The dimeric guaianolide was shown to be the most active constituent against Plasmodium falciparum (IC(50) = 2.0μM) and was less cytotoxic against rat skeletal myoblasts (IC(50) = 16.2μM, selectivity index of about 8).

Publication: Phytochemistry 2011 May ;72(7)::635-44. :doi: 10.1016/j.phytochem.2011.01.025.
Publication Date: 2011 May
Study Author(s): Maas, Mareike;Hensel, Andreas;Costa, Fernando Batista da;Brun, Reto;Kaiser, Marcel;Schmidt, Thomas J;
Institution: Institute of Pharmaceutical Biology and Phytochemistry, University of Münster, Hittorfstraße 56, D-48149 Münster, Germany.
Shortcut link to this study:
The CH(2)Cl(2) extract of aerial parts of Eupatorium perfoliatum L. exhibits antiprotozoal activity under in vitro conditions, especially against Plasmodium falciparum (IC(50)=2.7μg/ml). THE SEARCH FOR ACTIVE COMPOUNDS YIELDED SEVEN SESQUITERPENE LACTONES: Four structurally similar guaianolides, one dimeric guaianolide, and two germacranolides. The guaianolides differ in the degree of oxidation at C-14, ranging from a hydroxyl group up to a free carboxylic acid. The dimeric guaianolide, structurally closely related to the monomers, displays an unusual type of interguaianolide linkage between C-14 and C-4. Except for the germacranolide euperfolitin, all STLs described here were hitherto unknown. Furthermore, the flavonoid aglycones eupafolin, hispidulin, patuletin, and kaempferol were identified in the extract, which, except for kaempferol, have not been described as constituents of E. perfoliatum before. The dimeric guaianolide was shown to be the most active constituent against Plasmodium falciparum (IC(50) = 2.0μM) and was less cytotoxic against rat skeletal myoblasts (IC(50) = 16.2μM, selectivity index of about 8).
PMID: 21329950

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