title: Butenolide inhibits marine fouling by altering the primary metabolism of three target organisms.
abstract: Butenolide is a very promising antifouling compound that inhibits ship hull fouling by a variety of marine organisms, but its antifouling mechanism was previously unknown. Here we report the first study of butenolide's molecular targets in three representative fouling organisms. In the barnacle Balanus (=Amphibalanus) amphitrite, butenolide bound to acetyl-CoA acetyltransferase 1 (ACAT1), which is involved in ketone body metabolism. Both the substrate and the product of ACAT1 increased larval settlement under butenolide treatment, suggesting its functional involvement. In the bryozoan Bugula neritina, butenolide bound to very long chain acyl-CoA dehydrogenase (ACADVL), actin, and glutathione S-transferases (GSTs). ACADVL is the first enzyme in the very long chain fatty acid β-oxidation pathway. The inhibition of this primary pathway for energy production in larvae by butenolide was supported by the finding that alternative energy sources (acetoacetate and pyruvate) increased larval attachment under butenolide treatment. In marine bacterium Vibrio sp. UST020129-010, butenolide bound to succinyl-CoA synthetase β subunit (SCSβ) and inhibited bacterial growth. ACAT1, ACADVL, and SCSβ are all involved in primary metabolism for energy production. These findings suggest that butenolide inhibits fouling by influencing the primary metabolism of target organisms.
authors.affiliation: KAUST Collaborative Research Program, Division of Life Science, Hong Kong University of Science and Technology, Hong Kong SAR, China.
authors.forename: Yi-Fan
authors.initials: YF
authors.lastname: Zhang
authors.forename: Huoming
authors.initials: H
authors.lastname: Zhang
authors.forename: Lisheng
authors.initials: L
authors.lastname: He
authors.forename: Changdong
authors.initials: C
authors.lastname: Liu
authors.forename: Ying
authors.initials: Y
authors.lastname: Xu
authors.forename: Pei-Yuan
authors.initials: PY
authors.lastname: Qian
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000494:pharmacology; D000101:Acetyl-CoA C-Acetyltransferase / Q000378:metabolism; D000214:Acyl Coenzyme A / Q000378:metabolism; D044944:Acyl-CoA Dehydrogenases / Q000378:metabolism; D000818:Animals; D057219:Biofouling / Q000517:prevention & control*; D002013:Bryozoa / Q000187:drug effects* / Q000201:enzymology / Q000254:growth & development; D007814:Larva / Q000187:drug effects / Q000201:enzymology / Q000254:growth & development; D008958:Models, Molecular; D001468:Thoracica / Q000187:drug effects* / Q000201:enzymology / Q000254:growth & development; D014733:Vibrio / Q000187:drug effects* / Q000201:enzymology / Q000254:growth & development
chemical_list: D000214:Acyl Coenzyme A; C004511:butenolide; C012046:succinyl-coenzyme A; D044944:Acyl-CoA Dehydrogenases; D000101:Acetyl-CoA C-Acetyltransferase; D015107:4-Butyrolactone