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

地钱和它们的培养细胞生物合成高氧的次生代谢物。我们研究了高氧萜类化合物的产生及其生物合成途径，以验证化学物质的氧化降解能力。一种内分泌干扰化学物质双酚A(BPA)被培养的苔类细胞代谢。研究了含氧铜烯类化合物(-)-2-铜烯醇、(-)-2，3-二羟基铜烯和(-)-2，5-铜萜酮的生物合成。H_2，5^&lt；-13&gt；C]甲氧戊酸(MVA)作用于培养的水生地钱草细胞，然后对生成的^2H和^&lt；13&gt；C标记化合物进行^2H和^&lt；13&gt；C的核磁共振分析。标记图谱表明双取代基阳离子向铜烯基阳离子的立体选择性环化，并提供了同时参与c-…形成的1，4-和双1，3-氢化氢转移的证据更多的上游烯从铜烯基阳离子和羟基化到铜烯的芳香环上，与NIH移动生成2-铜烯醇和2，3-二羟基铜烯。从黄花菜的培养细胞中分离得到一个新的二萜类化合物Ptychantin O和两个已知的二萜化合物Ptychantin G和F，其结构经核磁共振分析得到确证。约95%的BPA最初存在(0.12 mm)，在这些苔类细胞培养5天后减少。双酚A可被to-4-propenylphenol，4-propylphenol，4-hydroxyacetophenone，4-isopropyl-2-hydroxyphenol，降解，也可被生物转化为4，4‘-isopropilidenediphenol-O-β-D-(6“-O-methyl)-glucopyranoside.。本文还研究了双酚A的生物降解机理，认为双酚A的降解产物是由胞外过氧化物酶对底物进行单电子氧化形成的。

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