Study on biodegradation of aromatic compounds by liverwort cultured cells toward bioremediation

苔类植物及其培养细胞可生物合成高含氧的次生代谢产物。我们研究了高度氧化的萜类化合物的生产及其生物合成途径，以验证化学品的氧化降解能力。研究了内分泌干扰物双酚A（BPA）在苔类植物培养细胞中的代谢。通过对培养的苔类植物Lejeunea aquatica细胞进行[2^<-13>C]-、[4^ C]-、<-13>[4^<-2>H_2]-、[4 ^<-2>H_2，4^<-13>C]-和[5^<-2>H_2，5^<-13>C]-甲羟戊酸（MVA）的培养，研究了含氧铜烯（-）-2-铜烯醇、（-）-2，3-二羟基铜烯和（-）2，5-铜醌的生物合成，并<13>对生成的~ 2 H和~ 1C标记化合物进行了~ 2 H和~ 1C NMR分析<13>。标记模式表明红没药基阳离子立体选择性环化为cupenyl阳离子，并提供了1，4-和双1，3-氢化物位移同时参与形成cupenyl的证据。 ...更多信息 从铜烯基阳离子和羟基化至铜烯的芳环，伴随NIH位移，生成2-铜烯醇和2，3-二羟基铜烯。从苔类植物Ptychanthus striatus的培养细胞中分离得到一个新的labdane型二萜化合物Ptychantin O和两个已知的二萜化合物Ptychantin G和F，并通过NMR分析确定了它们的结构研究了内分泌干扰物4-羟苯基丙烷对地钱、条纹地钱和扁平异囊藻培养细胞的影响。大约95%的BPA最初存在（0.12毫米）减少，在5天的培养这些苔类细胞。双酚A降解为4-丙烯基苯酚、4-丙基苯酚、4-羟基苯乙酮、4-异丙基-2-羟基苯酚，并可生物转化为4，4 '-异丙基二酚-O-β-D-（6”-O-甲基）-吡喃葡萄糖苷。并通过投加[^2H]-BPA的方法研究了BPA的生物降解机理<14>。BPA的降解产物被认为是由细胞外过氧化物酶单电子氧化底物形成的。少

The liverworts and their cultured cells biosynthesized highly oxygenated secondary metabolites. We examined the production of highly oxygenated terpenoids and their biosynthetic pathways to verify oxidative degradation capacity of chemicals. An endocrine-disturbing chemical, bisphenol A (BPA) was examined to be metabolized by cultured cells of the liverworts. The following results were obtained.The biosynthesis of oxygenated cuparenes, (-)-2-cuparenol, (-)-2,3-dihydroxycuparene and (-)2,5-cuparenoquinone, has been studied by feeding [2^<-13>C]-, [4^<-13>C]-, [4^<-2>H_2]-, [4^<-2>H_2, 4^<-13>C]-and [5^<-2>H_2, 5^<-13>C]mevalonate (MVA) to cultured liverwort cells, Lejeunea aquatica, followed by ^2H and ^<13>C NMR analysis of the resultant ^2H and ^<13>C labeled compounds. The labeling patterns indicate a stereoselective cyclization of a bisabolyl cation to a cuparenyl cation, and provide evidence for the simultaneous involvement of 1,4-and double 1,3-hydride shifts in the formation of c … More uparene from a cuparenyl cation and hydroxylation to the aromatic ring of cuparene with an NIH shift to generate 2-cuparenol and 2,3-dihydroxycuparene. The NIH shift was also confirmed in the formation of 2,5-cuparenoquinone.One novel labdane-type diterpene, named ptychantin O and two known diterpenes, ptychantin G and F have been isolated from cultured cells of the liverworts, Ptychanthus striatus, and their structures were determined by NMR analyzes.Degradation of BPA, 2,2-bis(4-hydroxyphenyl)propane, an endocrine disturbing chemical, by the cultured cells of liverworts, P.striatus and Heteroscyphus planus, was examined. About 95% of BPA initially present (0.12 mM) decreased in 5 days of culture of these liverwort cells. BPA was degraded to-4-propenylphenol,4-propylphenol,4-hydroxyacetophenone,4-isopropyl-2-hydroxyphenol, and also was biotransformed to 4,4'-isopropilidenediphenol-O-β-D-(6"-O-methyl)-glucopyranoside. Biodegradation mechanism of BPA was also examined by feeding [^2H_<14>]-BPA. The degradation products of BPA were assumed to be formed by the one-electron oxidation of the substrate by extracellular peroxidases. Less