Bioactive Polybrominated Diphenyl Ethers from the Marine Sponge Dysidea sp.

Abstract

A new polybrominated diphenyl ether ( 9), together with eight known compounds, were isolated from the crude organic extract of the marine sponge Dysidea sp. collected from the Federated States of Micronesia. Their structures were elucidated on the basis of various NMR spectroscopic data. These compounds exhibited inhibitory activities against Streptomyces 85E in the hyphae formation inhibition (HFI) assay and displayed antiproliferative activities against the human breast adenocarcinoma cancer cell line MCF-7. Compound 6 was selected for further evaluation in a cell cycle progression study.

Diphenyl ethers from Aspergillus sp. and their anti-Aβ42 aggregation activities

“…HR-ESI MS spectra were recorded using a Waters Synapt G2 mass spectrometer. 1D and 2D NMR spectra were recorded using a Bruker AV-400 spectrometer using solvent signals (DMSO-d 6 : δ H 2.50/δ C 39.5) as the internal standards. The analytical HPLC was performed on a Dionex HPLC system equipped with an Ultimate 3000 pump, an Ultimate 3000 diode array detector (DAD), an Ultimate 3000 Column Compartment, an Ultimate 3000 autosampler (Dionex, USA) and an Alltech (Grace) 2000 ES evaporative light scattering detector (ELSD) (Alltech, USA) using a reversed-phase C18 column (5 μm, 4.6 × 250 mm; Phenomenex, Gemini).…”

“…[10,11], Leathesia nana [12], Phyllanthus atropurpureus [13], Symphyocladia latiuscula [14], and so on. Diphenyl ethers exhibit a wide range of interesting biological activities, such as antimicrobial [1,3,6,8,10], cytotoxic [2,6,9], radical-scavenging [11], enzyme inhibitory [5], actin inhibitory [15], anti-HSV-1 [2], and phytocidal activities [16,17]. In early chemical investigation, we reported the isolation of two diphenyl ethers, 2-isopentenyldiorcinol (9) and diorcinol (10), from a strain of endolichenic fungus Aspergillus sp.…”

“…16-20-8-1) was re-fermented at the same scale. Further chemical investigation was carried out, which led to the isolation of eight compounds with the character of diphenyl ether structure, including four sterigmatocystins (1)(2)(3)(4) and four diphenyl ethers (5)(6)(7)(8). Among them, there were two new compounds, oxisterigmatocystin D (1), 9-acetyldiorcinol B (6), and six known compounds, oxisterigmatocystin A (2) [20], oxisterigmatocystin C (3) [20], sterigmatocystin (4) [21], diorcinol B (5) [22], violaceol-I (7) [23] and violaceol-II (8) [23] (Fig.…”

Contemporary 14C radiocarbon levels of oxygenated polybrominated diphenyl ethers (O-PBDEs) isolated in sponge–cyanobacteria associations

“…The OH- or MeO-functional group substitution in the ortho position of the diphenyl ether backbone is often found in compounds isolated from marine species and has helped to elucidate the origin of the PBDE metabolites observed at different trophic level organisms (Marsh et al, 2004). To date, more than 40 O-PHDEs are known to be derived from sponge–cyanobacteria associations (Zhang et al, 2008; Calcul et al, 2009), exhibiting bromine or chlorine atoms or both. However, the fourth compound isolated reported here, 2′-MeO-6-OH-BDE120, to our knowledge has not been previously described in the literature, although closer bromine substitution patterns were found in similar hydroxyl-methoxy-diphenyl ether structures isolated from marine sponges (Fu et al, 1995; Utkina et al, 2001; Oda et al, 2005).…”

Induced Production of Halogenated Diphenyl Ethers from the Marine‐Derived Fungus Penicillium chrysogenum

“…Encouraged by the detection of bioactive halogenated secondary metabolites, we manipulated the fermentation of P. chrysogenum by the addition of halide salts in an effort to gain access to a wider cross-section of polyhalogenated diphenyl ethers (PHDEs). PHDEs are known natural products that have been reported to occur in marine species such as sponge [10], ascidian (tunicate) [11], green alga [12], fish [13], and marine mammal [13]. These groups of substances have also been reported in fungus [14] and human [15].…”