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(25S)-Cholesten-26-oic acid derivatives from an Indonesian soft coral Minabea sp.
Authors:Weifang Wang  Takahiro Nakazawa  Remy EP Mangindaan  Henki Rotinsulu  Sachiko Tsukamoto
Institution:a Department of Natural Product Chemistry, Tohoku Pharmaceutical University, Aoba-ku, Sendai 981-8558, Japan
b Faculty of Fisheries and Marine Science, Sam Ratulangi University, Kampus Bahu, Manado 95115, Indonesia
c Institute of Molecular and Cellular Biosciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-0032, Japan
d Graduate School of Science, Chiba University, Inage-ku, Chiba 263-8522, Japan
Abstract:(25S)-3-Oxocholesta-1,4-dien-26-oic acid (1) and a new (25S)-18-acetoxy-3-oxocholesta-1,4-dien-26-oic acid (2) were isolated from a soft coral Minabea sp. (cf. aldersladei) collected in North Sulawesi, Indonesia, together with two known cholic-acid-type compounds, 3-oxochol-1,4-dien-24-oic acid (3) and 3-oxochol-4-en-24-oic acid (4). The structures of these compounds were determined on the basis of their spectroscopic data. The absolute stereochemistry at C-25 of 2 was determined by comparative 1H NMR study using chiral anisotropic reagents (S)- and (R)-phenylglycine methyl esters]. This is the first to report compound 1 as a natural product.
Keywords:Soft coral  Minabea sp    (25S)-3-Oxocholesten-26-oic acid  3-Oxocholen-24-oic acid  Steroidal carboxylic acids
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