title: Antifouling phenyl ethers and other compounds from the invertebrates and their symbiotic fungi collected from the South China Sea.
abstract: Marine organism-derived secondary metabolites are promising potential sources for discovering environmentally safe antifouling agents. In present study, 55 marine secondary metabolites and their synthesized derivatives were tested and evaluated for their antifouling activities and security. These compounds include 44 natural products isolated from marine invertebrates and their symbiotic microorganisms collected from the South China Sea and 11 structural modified products derived from the isolated compounds. The natural secondary metabolites, covering phenyl ether derivatives, terpenoids, 9, 11-secosteroids, anthraquinones, alkaloids, nucleoside derivatives and peptides, were isolated from two corals, one sponge and five symbiotic fungi. All of the isolated and synthesized compounds were tested for their antifouling activities against the cyprids of barnacle Balanus (Amphibalanus) amphitrite Darwin. Noticeably, five phenyl ether derivatives (9, 11, 13-15) exhibited potent anti-larval settlement activity with the EC50values lower than 3.05 μM and the LC50/EC50ratios higher than 15. The study of structure-activity relationship (SAR) revealed that the introduction of acetoxy groups and bromine atoms to phenyl ether derivatives could significantly improve their antifouling activities. This is the first report on the SAR of phenyl ether derivatives on antifouling activity against barnacle B. amphitrite. The polybrominated diphenyl ether derivative, 2, 4, 6, 2', 4', 6'-hexabromo-diorcinol (13), which displayed excellent antifouling activity, was considered as a promising candidate of environmentally friendly antifouling agents.
authors: Key Laboratory of Marine Drugs, School of Medicine and Pharmacy, The Ministry of Education of China, Ocean University of China, 5 Yushan Road, Qingdao, 266003, People's Republic of China.|Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao, 266071, People's Republic of China.
authors: Chao-Yi
authors: CY
authors: Wang
authors: Key Laboratory of Marine Drugs, School of Medicine and Pharmacy, The Ministry of Education of China, Ocean University of China, 5 Yushan Road, Qingdao, 266003, People's Republic of China.|Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao, 266071, People's Republic of China.|College of Life Science, Shenzhen University, 3688 Nanhai Ave, Shenzhen, 518060, People's Republic of China.
authors: Kai-Ling
authors: KL
authors: Wang
authors: KAUST Global Collaborative Research, Division of Life Science, Hong Kong University of Science and Technology, Clear Water Bay, Hong Kong, People's Republic of China.
authors: Pei-Yuan
authors: PY
authors: Qian
authors: College of Life Science, Shenzhen University, 3688 Nanhai Ave, Shenzhen, 518060, People's Republic of China.
authors: Ying
authors: Y
authors: Xu
authors: Key Laboratory of Marine Drugs, School of Medicine and Pharmacy, The Ministry of Education of China, Ocean University of China, 5 Yushan Road, Qingdao, 266003, People's Republic of China.|Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao, 266071, People's Republic of China.
authors: Min
authors: M
authors: Chen
authors: Key Laboratory of Marine Drugs, School of Medicine and Pharmacy, The Ministry of Education of China, Ocean University of China, 5 Yushan Road, Qingdao, 266003, People's Republic of China.|Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao, 266071, People's Republic of China.
authors: Juan-Juan
authors: JJ
authors: Zheng
authors: Key Laboratory of Marine Drugs, School of Medicine and Pharmacy, The Ministry of Education of China, Ocean University of China, 5 Yushan Road, Qingdao, 266003, People's Republic of China.|Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao, 266071, People's Republic of China.
authors: Min
authors: M
authors: Liu
authors: Key Laboratory of Marine Drugs, School of Medicine and Pharmacy, The Ministry of Education of China, Ocean University of China, 5 Yushan Road, Qingdao, 266003, People's Republic of China. shaochanglun@ouc.edu.cn.|Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao, 266071, People's Republic of China. shaochanglun@ouc.edu.cn.
authors: Chang-Lun
authors: CL
authors: Shao
authors: Key Laboratory of Marine Drugs, School of Medicine and Pharmacy, The Ministry of Education of China, Ocean University of China, 5 Yushan Road, Qingdao, 266003, People's Republic of China. changyun@ouc.edu.cn.|Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao, 266071, People's Republic of China. changyun@ouc.edu.cn.|Institute of Evolution and Marine Biodiversity, Ocean University of China, Qingdao, 266003, People's Republic of China. changyun@ouc.edu.cn.
authors: Chang-Yun
authors: CY
authors: Wang
keywords: Anti-larval settlement; Antifouling; Balanus amphitrite; Marine natural product; Phenyl ether derivative