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Antifouling Brominated Diterpenoids from Japanese Marine Red Alga Laurencia venusta Yamada |
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| Authors: | Ryosuke Fukada Yukimasa Yamagishi Misaki Nagasaka Daiki Osada Kazumi Nimura Iori Oshima Kazuki Tsujimoto Masayuki Kirihara Shinobu Takizawa Norio Kikuchi Takahiro Ishii Takashi Kamada |
| Affiliation: | 1. Faculty of Science and Technology, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka, 437-8555 Japan Contribution: Conceptualization (supporting), Data curation (lead), Writing - original draft (lead);2. Faculty of Life Science and Biotechnology, Fukuyama University, 1 Gakuen-cho, Fukuyama, Hiroshima, 729-0292 Japan;3. Department of Biosciences and Biotechnology, Faculty of Agriculture, University of the Ryukyus, 1 Senbaru, Nishihara, Okinawa, 903-0213 Japan Contribution: Formal analysis (supporting);4. Faculty of Science and Technology, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka, 437-8555 Japan Contribution: Data curation (supporting);5. Shizuoka Prefectural Research Institute of Fishery and Ocean, 136-24 Iwashigashima, Yaizu, Shizuoka, 425-0032 Japan Contribution: Data curation (supporting);6. Faculty of Science and Technology, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka, 437-8555 Japan Contribution: Formal analysis (supporting);7. Faculty of Science and Technology, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka, 437-8555 Japan;8. Artificial Intelligence Research Center, SANKEN, Osaka University, Mihogaoka, Ibaraki, Osaka, 567-0047 Japan;9. Coastal Branch of Natural History Museum and Institute, Chiba, 123 Yoshio, Katsuura, Chiba, 299-5242 Japan Contribution: Methodology (supporting);10. Department of Biosciences and Biotechnology, Faculty of Agriculture, University of the Ryukyus, 1 Senbaru, Nishihara, Okinawa, 903-0213 Japan |
| Abstract: | The marine red algal genus Laurencia has abundant halogenated secondary metabolites, which exhibit novel structural types and possess various unique biological potentials, including antifouling activity. In this study, we report the isolation, structure elucidation, and antifouling activities of two novel brominated diterpenoids, aplysin-20 aldehyde ( 1 ), 13-dehydroxyisoaplysin-20 ( 2 ), and its congeners. We screened marine red alga Laurencia venusta Yamada for their antifouling activity against the mussel Mytilus galloprovincialis. Ethyl acetate extracts of L. venusta from Hiroshima and Chiba, Japan, were isolated and purified, and the compound structures were identified using 1D and 2D NMR, HR-APCI-MS, IR, and chemical synthesis. Seven secondary metabolites were identified, and their antifouling activities were evaluated. Compounds 1 , 2 , and aplysin-20 ( 3 ) exhibited strong activities against M. galloprovincialis. Therefore, these compounds can be explored as natural antifouling drugs. |
| Keywords: | Laurencia venusta halogenated secondary metabolite diterpenoid C15 acetogenin antifouling |