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the greatly differing weight the plant material was not
weighed.
3.7. (+)-Muurolan-4,7-peroxide (4)
Colourless oil; RICPSIL 5 = 1485; sense of optical rota-
1
tion (benzene): (+); H NMR (500 MHz, C6D6): d 0.78
3.3. Isolation of single constituents of the essential oils
(3H, d, H-12, J = 6.9 Hz), 0.81–0.85 (1H, m, H-9a),
0.87 (3H, d, H-14, J = 6.9 Hz), 1.10 (3H, d, H-13,
J = 6.6 Hz), 1.15 (1H, d, H-5a, J = 11.4 Hz), 1.28 (3H,
s, H-15), 1.30–1.44 (3H, m, H-1, H-3a, H-10), 1.58–
1.62 (2H, m, H-2), 1.66–1.78 (5H, m, H-3b, H-8, H-9b,
H-11), 1.82 (1H, ddd, H-5b, J = 2.2, 4.7, 11.4 Hz), 2.00
(1H, t, H-6, J = 4.7 Hz); 13C NMR (125.7 MHz, C6D6):
see Table 1; MS (EI, 70 eV), m/z (rel. int.): 204 (4), 180
(14), 179 (100), 162 (12), 161 (90), 135 (10), 119 (18),
105 (55), 95 (17), 81 (29), 67 (9), 55 (14), 43 (26). MS
(CI, NH3 gas), m/z (rel. int.): 223 (M+ + 1 À O) (3), 221
(M+ + 1 À H2O) (1), 205 (100), 179 (45), 161 (24) 149
(2) 135 (5). MS (CI, iso-butane gas), m/z (rel. int.): 223
(M+ + 1 À O) (2) 221 (M+ + 1 À H2O) (10), 205 (85)
179 (100), 161 (47), 149 (12), 135 (8).
All isolations were carried out by prep. GC using SE-
30- and/or SE-52-columns combined with at least one
cyclodextrin derived stationary phase.
3.4. Bisabola-1,3,5,7(14)-tetraene (1)
Colourless oil; RICPSIL 5 = 1483; 1H NMR
(500 MHz, C6D6):
d 0.82 (6H, d, H-12, H-13,
J = 6.6 Hz), 1.16 (2H, q, H-10, J = 6.9 Hz), 1.40–1.50
(3H, m, H-11, H-9), 2.12 (3H, s, H-15), 2.44 (2H, t,
H-8, J = 7.5 Hz), 5.05 (1H, d, H-14a, J = 1.3 Hz),
5.34 (1H, d, H-14b, J = 1.6 Hz), 7.01 (2H, d, H-2, H-
4, J = 7.9 Hz), 7.33 (2H, d, H-1, H-5, J = 8.2 Hz); 13C
NMR (125.7 Hz, C6D6): see Table 1; MS (EI, 70 eV),
m/z (rel. int.): 202 [M+] (18), 187 (5), 159 (8), 145
(32), 132 (100), 131 (35), 119 (17), 117 (40), 115 (26),
105 (17), 77 (8), 65 (10), 55 (9), 41 (21). HREIMS
calcd. for C15H22 [M+] m/z 202.1721 found [M+] m/z
202.1723.
3.8. (+)-Plagio-4,7-peroxide (9)
Colourless oil; RICPSIL 5 = 1420; sense of optical
1
rotation (benzene): (+); H NMR (500 MHz, C6D6): d
0.81 (3H, d, H-12, J = 6.3 Hz), 0.91 (3H, d, H-14,
J = 6.3 Hz), 1.01 (1H, dt, H-1, J = 4.7, 12.6 Hz), 1.10–
1.18 (1H, m, H-9a), 1.21–1.28 (2H, m, H-5a, H-3a),
1.23 (3H, d, H-13, J = 6.6 Hz), 1.30 (3H, s, H-15),
1.44–1.58 (3H, H-8, H-2a), 1.64 (1H, dd, H-3b,
J = 5.7, 13.2 Hz), 1.68–1.76 (1H, m, H-10), 1.77–1.91
(2H, m, H-9b, H-2b), 1.94 (1H, dd, H-5b, J = 1.9,
10.4 Hz), 2.12–2.20 (1H, m, H-11), 3.30 (1H, d, H-7,
J = 10.4 Hz); 13C NMR (125.7 MHz, C6D6): see Table
1; MS (EI, 70 eV), m/z (rel. int.): 222 (<1), 221 (1), 220
(1.7), 207 (3), 179 (8), 161 (5), 150 (47), 135 (100), 121
(13), 107 (21), 95 (28), 94 (35), 93 (21), 79 (17), 67
(10), 55 (16), 43 (27). MS (CI, NH3 gas), m/z (rel. int.):
223 (M+ + 1 À O) (3), 221 (M+ + 1 À H2O) (1), 205
(100), 179 (3), 161 (2) 149 (2) 150 (22) 135 (34). MS
(CI, iso-butane gas), m/z (rel. int.): 223 (M+ + 1 À O)
(2) 221 (M+ + 1 À H2O) (18), 205 (100) 179 (12), 161
(8), 150 (76), 135 (67).
3.5. Bisabola-1,3,5,7-tetraene (2)
Colourless oil; RICPSIL 5 = 1557; 1H NMR
(500 MHz, C6D6):
d 0.88 (6H, d, H-12, H-13,
J = 6.9 Hz), 1.28 (2H, q, H-10, J = 6.9 Hz), 1.48–1.60
(1H, m, H-11, J = 6.9 Hz), 1.96 (3H, s, H-14), 2.14(2H,
q, H-9, J = 7.6 Hz), 2.16 (3H, s, H-15), 5.84 (1H, br. t,
H-8, J = 6.9 Hz), 7.04 (2H, d, H-2, H-4, J = 8.2 Hz),
7.34 (2H, d, H-1, H-5, J = 8.2 Hz); 13C NMR
(125.7 Hz, C6D6): see Table 1; MS (EI, 70 eV), m/z
(rel. int.): 202 [M+] (28), 145 (100), 132 (71), 131 (40),
115 (20), 105 (27), 91 (16), 77 (8), 65 (5), 53 (6), 41
(18). HREIMS calcd. for C15H22 [M+] m/z 202.1721
found [M+] m/z 202.1726.
3.6. (À)-Aromadendra-1(10),3-diene (3)
Colourless oil; RICPSIL 5 = 1512; sense of optical
1
rotation (benzene): (À); H NMR (500 MHz, C6D6): d
3.9. (+)-Plagiochiline W (10)
0.55–0.60 (1H, m, H-7), 0.68 (1H, t, H-6, J = 10.4 Hz),
0.98 (3H, s, H-12), 1.08 (3H, s, H-13), 1.55 (3H, s, H-
14), 1.56–1.62 (1H, m, H-8a), 1.66–1.73 (1H, m, H-8b),
1.68 (3H, s, H-15), 2.13–2.27 (2H, m, H-9), 3.00 (1H,
d, H-2a, J = 20.5 Hz), 3.06 (1H, d, H-5, J = 10.7 Hz),
3.14 (1H, d, H-2b, J = 20.5 Hz), 5.34–5.39 (1H, m, H-
3); 13C NMR (125.7 MHz, C6D6): see Table 1; MS
(EI, 70 eV), m/z (rel. int.): 202 [M+] (22), 187 (10), 159
(44), 145 (26), 133 (79), 132 (100), 131 (30), 117 (18),
105 (58), 91 (21), 77 (16), 67 (8), 53 (8), 41 (26). HRE-
IMS calcd. for C15H22 [M+] m/z 202.1721 found [M+]
m/z 202.1729.
Colourless oil; RICPSIL 5 = 1627; sense of optical
1
rotation (benzene): (+); H NMR (500 MHz, C6D6): d
0.49 (1H, dd, H-6, J = 9.5, 11.0 Hz), 0.89 (3H, d, H-15,
J = 7.3 Hz), 0.92 (3H, s, H-12), 0.97–0.99 (1H, m, H-
7), 0.99 (3H, s, H-13), 1.52–1.58 (1H, m, H-4), 1.77
(3H, s, H-14), 1.96 (1H, dd, H-5, J = 4.10, 11.0 Hz),
2.30 (2H, t, H-8, J = 7.6 Hz), 3.49 (1H, dd, H-3a,
J = 5.05, 10.4 Hz), 3.78 (1H, dd, H-3b, J = 2.5,
10.4 Hz), 5.44 (1H, t, H-9, J = 6.3 Hz), 6.78 (1H, s, H-
2); 13C NMR (125.7 MHz, C6D6): see Table 1; MS
(EI, 70 eV), m/z (rel. int.): 218 [M+] (100), 203 (18),