title: Coumarins from the Herb Cnidium monnieri and chemically modified derivatives as antifoulants against Balanus albicostatus and Bugula neritina larvae.
abstract: In the search for new environmental friendly antifouling (AF) agents, four coumarins were isolated from the herbal plant Cnidium monnieri, known as osthole (1), imperatorin (2), isopimpinellin (3) and auraptenol (4). Furthermore, five coumarin derivatives, namely 8-epoxypentylcoumarin (5), meranzin hydrate (6), 2'-deoxymetranzin hydrate (7), 8-methylbutenalcoumarin (8), and micromarin-F (9) were synthesized from osthole. Compounds 1, 2, 4, 7 showed high inhibitory activities against larval settlement of Balanus albicostatus with EC(50) values of 4.64, 3.39, 3.38, 4.67 μg mL-1. Compound 8 could significantly inhibit larval settlement of Bugula neritina with an EC(50) value of  3.87 μg mL-1. The impact of functional groups on anti-larval settlement activities suggested that the groups on C-5' and C-2'/C-3' of isoamylene chian could affect the  AF activities.
authors.affiliation: State Key Laboratory of Marine Environmental Science, Xiamen University, Xiamen 361005, China. chke@xmu.edu.cn.
authors.forename: Zhan-Chang
authors.initials: ZC
authors.lastname: Wang
authors.forename: Dan-Qing
authors.initials: DQ
authors.lastname: Feng
authors.forename: Cai-Huan
authors.initials: CH
authors.lastname: Ke
mesh_terms: D000818:Animals; D002013:Bryozoa / Q000187:drug effects* / Q000254:growth & development; D031048:Cnidium / Q000737:chemistry*; D003374:Coumarins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D011564:Furocoumarins / Q000737:chemistry / Q000494:pharmacology; D007814:Larva / Q000187:drug effects / Q000254:growth & development; D007928:Lethal Dose 50; D008956:Models, Chemical; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D001468:Thoracica / Q000187:drug effects* / Q000254:growth & development
chemical_list: D003374:Coumarins; D011564:Furocoumarins; D010936:Plant Extracts; C000591095:auraptenol; C015304:isopimpinellin; C031534:imperatorin; C046627:osthol