Y. Terada et al., Structure-activity relationship of phloroglucinol compounds from Eucalyptus as marine antifoulants, BIOS BIOT B, 63(2), 1999, pp. 276-280
Environmental pollution has resulted in the use of organo-tin and organo-co
pper compounds as antifouling agents being prohibited. Non-toxic natural pr
oducts are considered to be environmentally friendly antifouling agents. Se
veral phloroglucinol compounds isolated from three species of Eucalyptus ha
ve demonstrated strong attachment-inhibiting activity against the blue muss
el. 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 inhi
bitor was applied as a template, the repulsion energy of the other compound
s 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 electrost
atically resemble the template molecule are more active.