Ophirasterol, a new C31 sterol from the marine sponge Topsentia ophiraphidites |
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Authors: | Calderón Gladys J Castellanos Leonardo Duque Carmenza Echigo Shizue Hara Noriyuki Fujimoto Yoshinori |
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Institution: | Departamento de Química, Universidad Nacional de Colombia, Ciudad Universitaria, AA 14490, Bogotá, Colombia. |
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Abstract: | Analysis of the sterol fraction obtained from the Colombian Caribbean sponge Topsentia ophiraphidites revealed that this sponge is a rich source of C30 and C31 sterols. Among them, a new C31 sterol, named ophirasterol, was isolated, and its structure was established as (22E,24R)-24-(1-buten-2-yl)cholesta-5,22-dien-3beta-ol (1) by spectral means and comparison with synthetic C-24 epimers with known configuration. Other isolated C30 and C31 sterols were the known 24-ethyl-24-methyl-22-dehydrocholesterol (2), 24-isopropyl-22-dehydrocholesterol (3), 24-isopropylcholesterol (4), 24-ethyl-24-methylcholesterol (5), 24-isopropenyl-25-methyl-22-dehydrocholesterol (6) and 24-isopropenyl-25-methylcholesterol (7), and 24-isopropenyl-22-dehydrocholesterol (8). |
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Keywords: | Marine sterols Topsentia ophiraphidites Ophirasterol C31 sterols Caribbean sponges Orthoester Claisen rearrangement Stereochemistry |
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