Polybrominated Diphenyl Ethers from the Indonesian Sponge Lamellodysidea herbacea

Abstract

Four new (1-4) and 10 known polybrominated diphenyl ethers (5-14) have been isolated from the title sponge. The structures of the new entities were elucidated by interpretation of spectroscopic data and chemical transformations. These metabolites showed potent antimicrobial activity against Bacillus subtilis and moderate/weak cytotoxicity against NBT-T2 rat bladder epithelial cells. The major constituent 14 was treated under debromination conditions to give eight derivatives, which were subjected to a structure-activity relationship study. The results indicated that the presence of two phenolic hydroxyl groups and bromines at C-2 and/or C-5, as in 2, is important for the exhibition of antibacterial activity.

Selective determination of mono- and dihydroxylated analogs of polybrominated diphenyl ethers in marine sponges by liquid-chromatography tandem mass spectrometry

“…[5] in sponge tissues, although the profiles of these metabolites differ as a result of the diversity of species involved. The family Dysideidae, in particular, yields a number of hydroxylated polybrominated diphenyl ethers (OH-PBDEs), including dihydroxy (diOH), hydroxy-methoxy (OH-MeO), and dimethoxy (diMeO) analogs of tri-to hexa-BDEs [6,7]. These phenolic PBDE analogs exhibit a variety of bioactivities, such as antibacterial and antifungal properties [8], cytotoxicity, and enzyme inhibition [9].…”

“…These phenolic PBDE analogs exhibit a variety of bioactivities, such as antibacterial and antifungal properties [8], cytotoxicity, and enzyme inhibition [9]. Structure-activity relationships indicate that these activities may depend on the numbers and positions of hydroxyl groups [7]. In addition to PBDE homologs found in marine sponges, OH-PBDEs (e.g., 6-OH-BDE47) and the corresponding MeO-PBDEs (e.g., 2′-MeO-BDE68) have been reported to be present in marine algae [10], mussels [11], fish blood [12], as well as the marine food web [13][14][15][16][17][18].…”

Halioxepine, a New Meroditerpene from an Indonesian Sponge Haliclona sp.

“…The sponges belonging to the genus Haliclona are also prolific sources of unique molecules such as manzamines, 8) haliclonamines, 9) haliclonamides, 10) halipeptins, 11) and others. In our continuing search for new cytotoxic metabolites from Indonesian sponges, 12,13) we collected a small sponge belonging to Haliclona at Baubau, Indonesia. After the 1 H-NMR spectrum of a methanolic extract from the sponge indicated the presence of a unique molecule, we examined the chemical contents.…”

A NEW CYTOTOXIC DOLABELLANE FROM THE INDONESIAN SOFT CORAL <i>Anthelia</i> sp.

“…The isolation procedure was performed on the basis of the previous method [9]. The soft coral specimen (wet weight 121 g) stored in EtOH was extracted four times using Me 2 CO (4 x 150 mL).…”