Two new pyrrolo-2-aminoimidazoles from a Myanmarese marine sponge,Clathria prolifera |
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Authors: | Woo So-Yeun Win Nwet Nwet Wong Chin Piow Ito Takuya Hoshino Shotaro Ngwe Hla Aye Aung Aung Han Nang Mya Zhang Huiping Hayashi Fumiaki Abe Ikuro Morita Hiroyuki |
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Affiliation: | 1.Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama, 930-0194, Japan ;2.Department of Chemistry, University of Yangon, Yangon, 11041, Myanmar ;3.Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan ;4.Department of Marine Sciences, Myeik University, Yangon, 11041, Myanmar ;5.RIKEN Center for Life Science Technologies, 1-7-22 Suehiro-cho, Tsurumi-ku, Yokohama, Kanagawa, 230-0045, Japan ; |
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Abstract: | Marine organisms such as marine sponges and soft corals are valuable sources of pharmacologically active secondary metabolites. In our ongoing research on the discovery of new secondary metabolites from marine organisms, two new pyrrolo-2-aminoimidazoles, clathriroles A (1) and B (2), were isolated from the water-soluble portion prepared from the methanol and acetone (2:1) extract of the marine sponge, Clathria prolifera, collected in Myanmar. The chemical structures of the isolated compounds were determined using extensive spectroscopic techniques, including NMR, HRESIMS, IR, and optical rotation, and comparisons with the reported literature. The spectroscopic analyses of 1 and 2 suggested that 1 is an enantiomer of antifungal N-methylmanzacidin C isolated from the marine sponge Axinella brevistyla, whereas 2 is a diastereomer of manzacidin D at C-11 isolated from the marine sponge Astrosclera willeyana. To the best of our knowledge, this is the first report of the isolation of the pyrrolo-2-aminoimidazole compounds from C. prolifera. Furthermore, in contrast to the potency of N-methylmanzacidin C against Saccharomyces cerevisiae, the antifungal assay revealed that 1 and 2 lack any activity against this strain. Thus, these observations may suggest that the absolute configurations at both C-9 and C-11 play an important role in controlling the antifungal activity of this type of compound. |
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