Discovery of New Cytotoxic Aplaminone Derivatives from the Sea Hare Aplysia kurodai and Elucidation of Their Accumulation from Local Sea Algae through the Food Chain |
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Authors: | Yusuke Hioki Dr Tatsuya Sato Dr Toyoki Iwao Junya Ikuma Dr Atsushi Kawamura Dr Takayuki Ohyoshi Dr Yuta Tsunematsu Dr Masaki Kita |
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Institution: | 1. Graduate School of Bioagricultural Sciences, Nagoya University, Furo-cho, Chikusa, Nagoya, 464-8601 Japan;2. Zakko Club, 395 Ijika, Toba, 517-0026 Japan;3. Toba Fisheries Science Center, 641-9 Ohama, Toba, 517-0015 Japan;4. Faculty of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, 305-8571 Japan |
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Abstract: | The shell-less herbivorous marine mollusk (sea hare) Aplysia kurodai is known to contain a variety of bioactive substances. While these compounds have been thought to originate from sea algae or their associated microbes, most of their origin and acquisition pathways are still unclear. Six new cytotoxic aplaminone derivatives, bromodopamine-terpenoid hybrid molecules, were isolated from A. kurodai. Among them, isoaplaminone had a reverse prenyl group at the C15 aliphatic chain, which is a rare structural feature from the viewpoint of terpenoid biosynthesis. Investigation for chemical components in A. kurodai and the sea algae collected at several different locations revealed that two major aplaminones were contained in the Laurencia complex species at specific sites. Our chemical and ecological studies provide new insights into the origin of marine alkaloid toxins and their dynamism through the food chain. |
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Keywords: | Aplysia kurodai Sea Algae Marine natural products LC–MS/MS Chemical ecology |
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