Coumarins from the Herb Cnidium monnieri and Chemically Modified Derivatives as Antifoulants against Balanus albicostatus and Bugula neritina Larvae.docVIP

Int. J. Mol. Sci. 2013, 14, 1197-1206; doi:10.3390/ijmOPEN ACCESS International Journal of Molecular Sciences ISSN 1422-0067 /journal/ijms Article Coumarins from the Herb Cnidium monnieri and Chemically Modified Derivatives as Antifoulants against Balanus albicostatus and Bugula neritina Larvae Zhan-Chang Wang , Dan-Qing Feng and Cai-Huan Ke 1,2,* 1,2 2 1 State Key Laboratory of Marine Environmental Science, Xiamen University, Xiamen 361005, China; E-Mail: wzc_ttt@ (Z.-C.W.) 2 Department of Marine Technology and Ocean Engineering, College of Oceanography and Environmental Science, Xiamen University, Xiamen 361005, China; E-Mail: dqfeng@ (D.-Q.F.) * Author to whom correspondence should be addressed; E-Mail: chke@; Tel./Fax: +86-592-218-7420. Received: 11 October 2012; in revised form: 24 November 2012 / Accepted: 11 December 2012 / Published: 9 January 2013 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 ?1 Balanus albicostatus with EC50 values of 4.64, 3.39, 3.38, 4.67 μg mL . Compound 8 could significantly inhibit larval settlement of Bugula neritina with an EC50 value of ?1 3.87 μg mL . 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. Keywords: antifouling activity; Cnidium monnieri; coumarins; osthole; structure-activity relationship  Int. J. Mol. Sci. 2013, 14 1198 1.