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Potent Antifouling Marine Dihydroquinolin-2(1H)-one-Containing Alkaloids from the Gorgonian Coral-Derived Fungus Scopulariopsis sp.

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Abstract

Marine biofouling has a major economic impact, especially when it occurs on ship hulls or aquaculture facilities. Since the International Maritime Organization (IMO) treaty to ban the application of organotin-based paints to ships went into effect in 2008, there is an urgent demand for the development of efficient and environmentally friendly antifouling agents. Marine microorganisms have proved to be a potential source of antifouling natural compounds. In this study, six dihydroquinolin-2-one-containing alkaloids, three monoterpenoids combined with a 4-phenyl-3,4-dihydroquinolin-2(1H)-one (1–3) and three 4-phenyl-3,4-dihydroquinolin-2(1H)-one alkaloids (4–6), were isolated from the gorgonian coral-derived fungus Scopulariopsis sp. collected in the South China Sea. These dihydroquinolin-2-one-containing alkaloids were evaluated against the larval settlement of barnacle Balanus amphitrite, and antifouling activity was detected for the first time for this class of metabolites. All of them except 6 showed strong antifouling activity. Compounds 1 and 2 were discovered to be the most promising non-toxic antilarval settlement candidates. Especially, compound 1 is the strongest antifouling compound in nature until now which showed highly potent activity with picomolar level (EC50 17.5 pM) and a very safety and high therapeutic ratio (LC50/EC50 1200). This represents an effective non-toxic, anti-larval settlement structural class of promising antifouling lead compound.

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Acknowledgments

We would like to thank Prof. Z.-G She and Y. Xu for their useful discussion. This work was supported by the Program of National Natural Science Foundation of China (Nos. 41322037, 41176121, and 41130858), and the Program for New Century Excellent Talents in University, Ministry of Education of China (No. NCET-11-0472).

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Authors and Affiliations

  1. Key Laboratory of Marine Drugs, The Ministry Education of China, School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao, 266003, People’s Republic of China

    Chang-Lun Shao, Ru-Fang Xu, Chang-Yun Wang, Kai-Ling Wang & Mei-Yan Wei

  2. KAUST Global Collaborative Research, Division of Life Science, Hong Kong University of Science and Technology, Clear Water Bay, Hong Kong

    Pei-Yuan Qian

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  1. Chang-Lun Shao
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  2. Ru-Fang Xu
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  5. Kai-Ling Wang
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Correspondence to Chang-Lun Shao.

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Shao, CL., Xu, RF., Wang, CY. et al. Potent Antifouling Marine Dihydroquinolin-2(1H)-one-Containing Alkaloids from the Gorgonian Coral-Derived Fungus Scopulariopsis sp.. Mar Biotechnol 17, 408–415 (2015). https://doi.org/10.1007/s10126-015-9628-x

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  • DOI: https://doi.org/10.1007/s10126-015-9628-x

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