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雌三醇向雌酮的转化:一种细菌代谢雌三醇的策略。

Conversion of estriol to estrone: A bacterial strategy for the catabolism of estriol.

机构信息

Institute of Organic Contaminant Control and Soil Remediation, College of Resources and Environmental Sciences, Nanjing Agricultural University, Nanjing 210095, PR China.

Institute of Animal Husbandry and Poultry Science, Nanjing 210017, PR China.

出版信息

Ecotoxicol Environ Saf. 2024 Jul 15;280:116564. doi: 10.1016/j.ecoenv.2024.116564. Epub 2024 Jun 11.

Abstract

Natural estrogens, including estrone (E1), 17β-estradiol (E2), and estriol (E3), are potentially carcinogenic pollutants commonly found in water and soil environments. Bacterial metabolic pathway of E2 has been studied; however, the catabolic products of E3 have not been discovered thus far. In this study, Novosphingobium sp. ES2-1 was used as the target strain to investigate its catabolic pathway of E3. The metabolites of E3 were identified by high performance liquid chromatography-high resolution mass spectrometry (HPLC-HRMS) combined with stable C-labeling. Strain ES2-1 could almost completely degrade 20 mg∙L of E3 within 72 h under the optimal conditions of 30°C and pH 7.0. When inoculated with strain ES2-1, E3 was initially converted to E1 and then to 4-hydroxyestrone (4-OH-E1), which was then cleaved to HIP (metabolite A6) via the 4, 5-seco pathway or cleaved to the B loop via the 9,10-seco pathway to produce metabolite with a long-chain ketone structure (metabolite B4). Although the ring-opening sequence of the above two metabolic pathways was different, the metabolism of E3 was achieved especially through continuous oxidation reactions. This study reveals that, E3 could be firstly converted to E1 and then to 4-OH-E1, and finally degraded into small molecule metabolites through two alternative pathways, thereby reducing E3 pollution in water and soil environments.

摘要

天然雌激素,包括雌酮(E1)、17β-雌二醇(E2)和雌三醇(E3),是普遍存在于水和土壤环境中的潜在致癌污染物。E2 的细菌代谢途径已被研究,但迄今为止尚未发现 E3 的代谢产物。在本研究中,以诺氏菌 ES2-1 为目标菌株,研究其 E3 的代谢途径。采用高效液相色谱-高分辨质谱(HPLC-HRMS)结合稳定 C 标记法鉴定 E3 的代谢产物。在 30°C 和 pH 值 7.0 的最佳条件下,ES2-1 菌株在 72 h 内几乎可以完全降解 20 mg·L 的 E3。当接种 ES2-1 菌株时,E3 首先转化为 E1,然后转化为 4-羟基雌酮(4-OH-E1),然后通过 4,5-裂环途径裂解为 HIP(代谢物 A6),或通过 9,10-裂环途径裂解为带有长链酮结构的代谢物(代谢物 B4)。尽管这两种代谢途径的开环序列不同,但 E3 的代谢主要通过连续氧化反应来实现。本研究表明,E3 可首先转化为 E1,然后转化为 4-OH-E1,最终通过两种替代途径降解为小分子代谢物,从而减少水和土壤环境中 E3 的污染。

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