Absolute stereochemistry of citrinadins a and B from marine-derived fungus |
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Authors: | Mugishima Takao Tsuda Masashi Kasai Yuu Ishiyama Haruaki Fukushi Eri Kawabata Jun Watanabe Masayuki Akao Kenichi Kobayashi Jun'ichi |
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Institution: | Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan. |
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Abstract: | Structure: see text]. Citrinadin A (2) is a pentacyclic indolinone alkaloid isolated from the cultured broth of a fungus, Penicillium citrinum, which was separated from a marine red alga. The absolute stereochemistry of the pentacyclic core in 2 and its new congener, citrinadin B (1), was elucidated by analysis of the ROESY spectrum for the chlorohydrin derivative (3) of 1 as well as comparison of the electronic circular dichroism (ECD) spectra for 1 and 2 with those of known spirooxiindole alkaloids. On the other hand, the absolute configuration at C-21 bearing an epoxide ring was assigned as S by comparison of the vibrational circular dichroism (VCD) spectra of 1 with those of model compounds 2S- and 2R-2,3-epoxy-3,3-dimethyl-1-phenylpropan-1-one (4a and 4b, respectively). |
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