Inoue Daisuke, Hara Shoji, Kashihara Mari, Murai Yusaku, Danzl Erica, Sei Kazunari, Tsunoi Shinji, Fujita Masanori, Ike Michihiko
Division of Sustainable Energy and Environmental Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.
Appl Environ Microbiol. 2008 Jan;74(2):352-8. doi: 10.1128/AEM.01708-07. Epub 2007 Nov 16.
Three bacteria capable of utilizing bis(4-hydroxyphenyl)methane (bisphenol F [BPF]) as the sole carbon source were isolated from river water, and they all belonged to the family Sphingomonadaceae. One of the isolates, designated Sphingobium yanoikuyae strain FM-2, at an initial cell density of 0.01 (optical density at 600 nm) completely degraded 0.5 mM BPF within 9 h without any lag period under inductive conditions. Degradation assays of various bisphenols revealed that the BPF-metabolizing system of strain FM-2 was effective only on the limited range of bisphenols consisting of two phenolic rings joined together through a bridging carbon without any methyl substitution on the rings or on the bridging structure. A BPF biodegradation pathway was proposed on the basis of metabolite production patterns and identification of the metabolites. The initial step of BPF biodegradation involves hydroxylation of the bridging carbon to form bis(4-hydroxyphenyl)methanol, followed by oxidation to 4,4'-dihydroxybenzophenone. The 4,4'-dihydroxybenzophenone appears to be further oxidized by the Baeyer-Villiger reaction to 4-hydroxyphenyl 4-hydroxybenzoate, which is then cleaved by oxidation to form 4-hydroxybenzoate and 1,4-hydroquinone. Both of the resultant simple aromatic compounds are mineralized.
从河水中分离出三种能够以双（4-羟苯基）甲烷（双酚F [BPF]）作为唯一碳源的细菌，它们均属于鞘脂单胞菌科。其中一种分离菌株，命名为矢野鞘氨醇单胞菌FM-2菌株，在诱导条件下，初始细胞密度为0.01（600nm处的光密度）时，能在9小时内完全降解0.5 mM BPF，且无任何延迟期。对各种双酚的降解试验表明，FM-2菌株的BPF代谢系统仅对由两个酚环通过桥连碳连接在一起且环上或桥连结构上无任何甲基取代的有限范围的双酚有效。基于代谢产物的产生模式和代谢产物的鉴定，提出了一条BPF生物降解途径。BPF生物降解的第一步涉及桥连碳的羟基化形成双（4-羟苯基）甲醇，随后氧化为4,4'-二羟基二苯甲酮。4,4'-二羟基二苯甲酮似乎通过拜耳-维利格反应进一步氧化为4-羟基苯基4-羟基苯甲酸酯，然后通过氧化裂解形成4-羟基苯甲酸酯和1,4-对苯二酚。这两种生成的简单芳香化合物都被矿化。
