Isolation and Characterization of Polybrominated Diphenyl Ethers as Inhibitors of Microtubule Assembly from the Marine Sponge Phyllospongia dendyi Collected at Palau

Abstract

Two new polybrominated diphenyl ethers (1 and 2) were isolated by bioassay-guided separations together with nine known compounds (3-11) from the marine sponge Phyllospongia dendyi collected from Palau. The structures were assigned on the basis of their spectral data. Compounds 3, 7, and 10 showed inhibitory activities to the assembly of microtubule proteins (IC(50): 29.6, 33.5, and 20.9 microM, respectively) and to the meiotic maturation of starfish oocytes (IC(50): 3.6, 4.2, and 4.2 microM, respectively), while 1, 2, 4-6, 8, 9, and 11 were not active at 100 microM. Two phenolic hydroxyls are required for their bioactivities.

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

“…The simultaneous determination of OH-, OH-MeO-, and diOH-PBDEs in phenolic fractions are of great importance in monitoring studies of animals and humans, because these analogs exhibit a variety of bioactivities, depending on the structure (the presence of one or two hydroxyl groups in PBDE molecules) [7][8][9]. For example, diOH-PBDEs and OH-MeO-PBDEs are active against the Gram-positive bacterium Bacillus subtilis, whereas in their methylated analogs (diMeO-PBDEs), such activity is reduced [7].…”

“…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]. Structure-activity relationships indicate that these activities may depend on the numbers and positions of hydroxyl groups [7].…”

Diphenyl Ether Glycoside from the Stems of Ilex litseaefolia Hu et Tang

“…The first brominated diphenyl ether was isolated from sponge (Carté and Faulkner 1981). This kind of compound possesses various bioactivities such as antibacterial (Oh et al 1999), antitumor (Jayasuriya et al 1995;Fuente et al 2003;Liu et al 2004), anti-inflammatory (Wiemer et al 1991), antiviral (Rich et al 1992) and herbicidal (Hargreaves et al 2002) effects. However, ilexfoliaoside (compound 1) may not contribute any bioactivity for I. litseaefolia in view of the isolated yield.…”

Evolution, radiation and chemotaxonomy of Lamellodysidea, a demosponge genus with anti-plasmodial metabolites

“…1 H, 13 C, HSQC and HMBC data readily identiWed the benzenoid rings of the PBDEs and particularly the B ring as a 3,5-dibromo-2-hydroxy(or 2-methoxy)phenoxyl group. Regiochemical assignment of the A ring was achieved by further analysis of the HMBC spectra and comparison of the 1 H and 13 C chemical shifts in diVerent solvents with the literature (Norton et al 1981;Fu et al 1995;Fu and Schmitz 1996;Liu et al 2004;Xu et al 2005;Hanif et al 2007;Calcul et al 2009). …”