Martefragin A (1), a novel indole alkaloid, was isolated from a red alga, Martensia fragilis, by repeated column chromatography. The structure of 1 was elucidated on the basis of spectral analysis of its methyl ester (2), including 1H- and 13C-NMR, 1H-1H correlation spectroscopy (COSY), and 13C-1H COSY. A single crystal X-ray analysis of the hydrochloride of 1 confirmed the assignment. Martefragin A (1) showed inhibitory activity on NADPH-dependent lipid peroxidation in rat liver microsomes. The IC50 values of 1, alpha-tocopherol and ascorbic acid were 2.8, 87 and 200 microM, respectively.
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[Synthetic study of biologically important nitrogen containing natural products: development of new methodology and design of leading compounds for new pharmaceuticals].
Yakugaku Zasshi
April 2003
Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba City 263-8522, Japan.
Synthetic study of biologically important nitrogen-containing natural products and development of new methodologies and design of leading compounds for new pharmaceuticals are described. The first total synthesis of eudistomines, manzamine C, martefragin A, cerebroside B1b, and symbioramide was accomplished and the absolute configurations of the stereogenic centers were determined. A novel methodology useful for the synthesis of alkaloids that have perhydroisoquinoline ring system such as manzamine A and B, and related alkaloids, nakadomarin A and dynemicin A, is presented.
View Article and Find Full Text PDFMartefragin A, a novel indole alkaloid isolated from red alga, inhibits lipid peroxidation.
Chem Pharm Bull (Tokyo)
October 1998
Toyama Prefectural Institute for Pharmaceutical Research, Japan.
Martefragin A (1), a novel indole alkaloid, was isolated from a red alga, Martensia fragilis, by repeated column chromatography. The structure of 1 was elucidated on the basis of spectral analysis of its methyl ester (2), including 1H- and 13C-NMR, 1H-1H correlation spectroscopy (COSY), and 13C-1H COSY. A single crystal X-ray analysis of the hydrochloride of 1 confirmed the assignment.
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