Mellado Gonzalo G, Zubía Eva, Ortega María J, López-González Pablo J
Departamento de Química Orgánica, Facultad de Ciencias del Mar y Ambientales, Universidad de Cádiz, Apdo. 40, 11510-Puerto Real, Cádiz, Spain.
Steroids. 2004 Apr;69(4):291-9. doi: 10.1016/j.steroids.2004.02.005.
The chemical study of the Antarctic octocoral Dasystenella acanthina has led to the isolation of the new polyoxygenated steroids (24R,22E)-24-hydroxycholest-4,22-dien-3-one (1), 23-acetoxy-24,25-epoxycholest-4-en-3-one (2), 12beta-acetoxycholest-4-en-3,24-dione (3), 12beta-acetoxy-24,25-epoxycholest-4-en-3-one (4), (22E)-25-hydroxy-24-norcholest-4,22-dien-3-one (5), 3alpha-acetoxy-25-hydroxycholest-4-en-6-one (6), and 3alpha,11alpha-diacetoxy-25-hydroxycholest-4-en-6-one (7), whose structures have been established by spectroscopic analysis. The absolute stereochemistry at C-24 in compound 1 has been determined through the 1H NMR study of the corresponding (R)- and (S)-MPA esters. All the new compounds showed significant activities as growth inhibitors of several human tumor cell lines. In addition, cytostatic and cytotoxic effects were also observed on selected tumor cell lines.
对南极八放珊瑚棘刺软珊瑚(Dasystenella acanthina)的化学研究已导致分离出新型多氧化甾体:(24R,22E)-24-羟基胆甾-4,22-二烯-3-酮(1)、23-乙酰氧基-24,25-环氧胆甾-4-烯-3-酮(2)、12β-乙酰氧基胆甾-4-烯-3,24-二酮(3)、12β-乙酰氧基-24,25-环氧胆甾-4-烯-3-酮(4)、(22E)-25-羟基-24-降胆甾-4,22-二烯-3-酮(5)、3α-乙酰氧基-25-羟基胆甾-4-烯-6-酮(6)以及3α,11α-二乙酰氧基-25-羟基胆甾-4-烯-6-酮(7),其结构已通过光谱分析确定。化合物1中C-24处的绝对立体化学已通过对相应的(R)-和(S)-MPA酯的1H NMR研究确定。所有新化合物对几种人类肿瘤细胞系均显示出显著的生长抑制活性。此外,在选定的肿瘤细胞系上还观察到了细胞生长抑制和细胞毒性作用。