Abstract
Two new cytotoxic antitumor diterpenoids of the cembrane class, named 14-deoxycrassin (3) and pseudoplexaurol (4), have been isolated from the Caribbean gorgonian octocoralPseudoplexaura porosa. The structure of lactone3, possessing the infrequently encountered α-methylene-δ-lactone ring, has been established from spectral and chemical data and that of alcohol4 has been established from spectral data.
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Literature
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IR (neat)v max 3436, 2932, 2865, 1720, 1617, 1445, 1378, 1264, 1180, 1132, 1096, 1031, 954, 790 cm−1; LREIMSm/z (%) 318(5), 300(4), 275(5), 241(3), 219(3), 193(11), 147(21), 133(26), 121(36), 107(52), 93(60), 81(100), 67(62), 55(80).
1H-NMR (300-MHz, CDCl3) δ 6.40 (1H, d, J=2.1 Hz, H-17α), 5.59 (1H, d, J=2.1 Hz, H-17β), 5.09 (1H, m), 5.02 (1H, t,J=7.5 Hz), 3.96 (1H, d,J=10.2 Hz), 2.32–1.60 (broad envelope), 1.57 (3H, s), 1.53 (3H, s), 1.35 (3H, s), 1.33–1.10 (broad envelope).
The1H−1H COSY spectrum of3 showed the following cross peaks (partial list): H-17α/H-17β, H-13/H-14, H-14/H-1, H-1/H-2, H-2β/H-3, H-7/H-6, H-7/Me-19, H-11/H-10, H-11/Me-20.
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The Selective INEPT spectrum of4 showed the following2,3JCH correlations (partial list): H-17αβ/C-1, C-15 and C-16; H-16/C-15, C-17 and C-1; H-3/C-2 and C-5; H-18/C-3, C-4 and C-5.
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Rodríguez, A.D., Martínez, N. Marine antitumor agents: 14-deoxycrassin and pseudoplexaurol, new cembranoid diterpenes from the Caribbean gorgonianPseudoplexaura porosa . Experientia 49, 179–181 (1993). https://doi.org/10.1007/BF01989427
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DOI: https://doi.org/10.1007/BF01989427