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

Abstract

Manipulation of the fermentation of the marine-derived fungus Penicillium chrysogenum by addition of CaBr(2) resulted in induced production of bromodiphenyl ether analogs. Two new free-radical-scavenging polybrominated diphenyl ethers, 1 and 2, and three known diphenyl ethers, 3,3'-dihydroxy-5,5'-dimethyldiphenyl ether (3), and an inseparable mixture of violacerol-I (4) and violacerol-II (5) were isolated. The structures of the two new polybromodiphenyl ethers 1 and 2 were assigned by combined spectroscopic-data analysis, including deuterium-induced isotope effect. Compounds 1-3, and a mixture of 4 and 5 exhibited radical-scavenging activities against 1,1-diphenyl-2-picrylhydrazyl with IC(50) values of 18, 15, 42, and 6 μM, respectively. With the exception of 3, the compounds were, therefore, more active than the positive control, ascorbic acid (IC(50) 20 μM).

Diorcinols B-E, new prenylated diphenyl ethers from the marine-derived fungus Aspergillus versicolor ZLN-60

“…14 These structurally similar diphenyl ethers showed diverse biological activities such as anti-microbial, 11,15,16 cytotoxic 17 and radical-scavenging activities. 18 To our knowledge, this is the first report for the isolation of prenylated diphenyl ethers from a member of the genus Aspergillus, and compounds 3 and 4 exhibited cytotoxicities.…”

Bioactive Compounds Produced by Strains of Penicillium and Talaromyces of Marine Origin

“…Radical scavenging effects were also reported for compound JBIR-59 ( Figure 3 ), on account of its protective effects against l -glutamate toxicity in neuronal hybridoma N18-RE-105 cells [ 99 ]. A few more products ( Figure 3 ) have been characterized as free radical scavengers based on their activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH), such as the terrestrols [ 64 ], 4,6,4′,6′-tetrabromo-3,3′-dihydroxy-5,5′-dimethyldiphenyl ether and 4,6,2′,4′,6′-pentabromo-3,3′-dihydroxy-5,5′-dimethyldiphenyl ether [ 105 ], the variecolorins [ 102 ], compound JBIR-124 [ 100 ], and sargassopenillines A and E [ 160 ]. Further indirect antitumor effects resulting from detoxification of xenobiotics have been proposed for the meroterpenoid penicillipyrone B ( Figure 3 ) for its ability to induce the enzyme quinone-reductase, which is involved in the reduction of electrophilic quinones [ 151 ].…”

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

“…[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.…”