title: Structure-Activity Relationship of Phloroglucinol Compounds from Eucalyptus as Marine Antifoulants.
abstract: Environmental pollution has resulted in the use of organo-tin and organo-copper compounds as antifouling agents being prohibited. Non-toxic natural products are considered to be environmentally friendly antifouling agents. Several phloroglucinol compounds isolated from three species of Eucalyptus have demonstrated strong attachment-inhibiting activity against the blue mussel. In this paper, we discuss the structure-activity relationship of these phloroglucinol compounds on the basis of molecular mechanics calculations. When these compounds were superimposed on each other and the strongest inhibitor was applied as a template, the repulsion energy of the other compounds was proportional to the logarithmic attachment-inhibiting activity. It is concluded that, of the two phloroglucinol rings in sideroxylonal A, ring C is more important, and those compounds that stereochemically and electrostatically resemble the template molecule are more active.
authors.affiliation: a Faculty of Pharmacy, Meijo University.
authors.forename: Y
authors.initials: Y
authors.lastname: Terada
authors.affiliation: a Faculty of Pharmacy, Meijo University.
authors.forename: J
authors.initials: J
authors.lastname: Saito
authors.affiliation: a Faculty of Pharmacy, Meijo University.
authors.forename: T
authors.initials: T
authors.lastname: Kawai
authors.affiliation: b Faculty of Agriculture, Shizuoka University.
authors.forename: I P
authors.initials: IP
authors.lastname: Singh
authors.affiliation: b Faculty of Agriculture, Shizuoka University.
authors.forename: H
authors.initials: H
authors.lastname: Etoh
keywords: marine antifoulant; molecular mechanics calculation; phloroglucinol derivative; structure-activity relationship; superimposition calculation