Ecological and Pharmacological Activities of Polybrominated Diphenyl Ethers (PBDEs) from the Indonesian Marine Sponge Lamellodysidea herbacea

Two known Polybrominated Diphenyl Ethers (PBDEs), 3,4,5-tribromo-2-(2 & PRIME;,4 & PRIME;-dibromophenoxy)phenol (1d) and 3,4,5,6-tetrabromo-2-(2 & PRIME;,4 & PRIME;-dibromophenoxy)phenol (2b), were isolated from the Indonesian marine sponge Lamellodysidea herbacea. The structure was confirmed using C-13 chemical shift average deviation and was compared to the predicted structures and recorded chemical shifts in previous studies. We found a wide range of bioactivities from the organic crude extract, such as (1) a strong deterrence against the generalist pufferfish Canthigaster solandri, (2) potent inhibition against environmental and human pathogenic bacterial and fungal strains, and (3) the inhibition of the Hepatitis C Virus (HCV). The addition of a bromine atom into the A-ring of compound 2b resulted in higher fish feeding deterrence compared to compound 1d. On the contrary, compound 2b showed only more potent inhibition against the Gram-negative bacteria Rhodotorula glutinis (MIC 2.1 mu g/mL), while compound 1d showed more powerful inhibition against the other human pathogenic bacteria and fungi. The first report of a chemical defense by compounds 1d and 2b against fish feeding and environmental relevant bacteria, especially pathogenic bacteria, might be one reason for the widespread occurrence of the shallow water sponge Lamellodysidea herbacea in Indonesia and the Indo-Pacific.

Automated summary

Two PBDEs, 3,4,5-tribromo-2-(2',4'-dibromophenoxy)phenol (1d) and 3,4,5,6-tetrabromo-2-(2',4'-dibromophenoxy)phenol (2b), isolated from the Indonesian marine sponge Lamellodysidea herbacea, showed a wide range of bioactivities, including strong deterrence against pufferfish, potent inhibition against bacterial and fungal strains, and inhibition of Hepatitis C Virus. The addition of a bromine atom into compound 2b resulted in higher fish feeding deterrence, while compound 1d showed more powerful inhibition against other human pathogenic bacteria and fungi. The compounds' chemical defense against fish feeding and pathogenic bacteria might explain the widespread occurrence of Lamellodysidea herbacea in Indonesia and the Indo-Pacific.