1. In addition, the pregnane steroids Δ1-pregnene-3βol-20-one, Δ4-pregnene-3,20-dione, Δ4-pregnene-3βol-20-one, and Δ1,4-pregnadiene-3,20-dione were isolated.
2. For subergorgic acid (1): m.p. 179–180°; [α]D -230° (c. 0.7, CHCl3); 1H NMR (360 MHz, CDCl3): δ 6.43 (1H, bs, C-9), 3.01 (1H, q, J=7 Hz, C-11), 2.37 (1H, dd, J=16.7, 6.7, C-3), 2.09 (1H, dd, J=8.8, 6.7, C-5), 2.01 (1H, dd, J=16.7, 12.6. C-3), 1.22 (3H, s, C-13), 1.13 (3H, d, J=7.3, C-15), 1.12 (3Hd, J=6.4C-12); 13C NMR (50 MHz, CDCl3): δ217.8 (s, C-2), 169.6 (s, C-14), 152.1 (d, C-9), 136.6 (s, C-10), 68.5 (s, C-1), 61.7 (s, C-8), 62.6, 51.6, 33.3 (all d's, C-4, C-5, and C-11), 49.9, 38.2, 28.3 (all t's, C-3, C-6, and C-7), 23.4, 19.9, 17.7 (all q's, C-12, C-13, and C-15); HRMS (EI): M+ m/z=248.1405 (26%), M+-H2O 230.1332 (100%), 215.1118 (29%), M+-COOH 203.1443 (27%), 202 (30%); IR (CH2Cl2): 1730. 1690, and 1645 cm-1.
3. For methyl ester 2: 1H NMR (CDCl3): δ 6.28 (1H, s, C-9), 3.73 (3H, s, OMe), 3.02 (1H, q, J=7.1, C-11), 2.35 (1H, dd, J=16.6, 6.8, C-3), 2.08 (1H, dd, J=8.9, 6.8, C-5), 2.00 (1H, dd, J=16.6, 12.6, C-3), 1.20 (3H, s, C-13), 1.12 (3H, d, J=6.4, C-12), 1.11 (3H, d, J=7.1, C-15); IR (CCl4): 1730, 1710, 1650, 1540, 1520, 1490, and 1460 cm−1.
4. For alcohol 3: 1H NMR (360 MHz, CDCl3): δ 5.14 (1H, s, C-9), 4.18 (3H, m, C-2 and C-14), 2.76 (1H, q, J=7, C-11), 1.93 (1H, ddd, J=15, 10, 4, C-3), 1.30 (3H, d, J=7, C-15), 1.15 (3H, s, C-13), 1.13 (3H, d, J=6.6, C-12); IR (CCl4): 3600, 1640, 1540, 1520, 1500, and 1450 cm−1. For alcohol 4: 1H NMR (CDCl3): δ 5.25 (1H, s, C-9), 4.36 (1H, bs, C-2), 4.15 (2H, AB q, J=13.4, C-14), 2.36 (1H. q, J=7, C-11), 1.33 (3H, s, C-13). 1.05 (3H, d, J=7, C-15), 1.04 (3H, d, J=6.4, C-12); IR (CCl4): 3600, 1640, 1540, 1510, 1490, and 1450 cm−1. The stereochemistries of 3 and 4 were based on the downfield shift of the 1H NMR signal of C-13 in 4 and the similar shift of C-15 in 3.