Zearalenon | 14328-07-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: Zearalenon
• 英文别名: (S,E)-Zearalenone；(12E)-16,18-dihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraene-2,8-dione
• CAS: 14328-07-5
• 化学式: C₁₈H₂₂O₅
• 分子量: 318.37
• InChiKey: MBMQEIFVQACCCH-XVNBXDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

ADMET

代谢

玉米赤霉烯酮口服给药后可迅速吸收。在人体内，大部分吸收的玉米赤霉烯酮不发生代谢。主要代谢物包括α-和β-玉米赤霉醇，以及玉米赤霉烯酮及其代谢物的葡萄糖苷酸结合物。玉米赤霉烯酮及其代谢物主要通过胆汁排泄。(A741, L1912)

Zearalenone is rapidly absorbed after oral administration. In humans, most of the zearalenone absorbed is not metabolized. The main metabolites include alpha- and beta-zeralenol, and the glucuronide conjugates of both the parent compound and its metabolites. Zearalenone and its metabolites are excreted mainly in the bile. (A741, L1912)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

玉米赤霉烯酮的基因毒性源于其能够引起DNA断裂、染色体畸变和DNA加合物形成。它通过增强脂质过氧化、增加氧化应激和诱导细胞凋亡来发挥细胞毒性作用。玉米赤霉烯酮还具有显著的雌激素活性，能引起动物的严重生殖问题。在人类中，玉米赤霉烯酮已显示出能导致儿童早熟、子宫内膜腺癌、女性乳腺增生和乳腺癌。霉菌毒素通常能够通过人类有机阴离子转运体（hOATs）和人类有机阳离子转运体（hOCTs）进入肝脏和肾脏。它们还能抑制这些转运体对阴离子和阳离子的摄取，干扰内源代谢物、药物和外源性物质（包括它们自身）的分泌。这导致有毒化合物在细胞内积累增加，引起肾毒性和肝毒性。（A2960, A3014）

Zearalenone's genotoxicity results from it's ability to cause DNA fragmentation, chromosome aberrations, and DNA adduct formation. It exerts cytotoxic effects by enhancing lipid peroxidation, increasing oxidative stress, and inducing apoptosis. Zearalenone also has significant estrogenic activity, causing severe reproductive problems in animals. In humans, Zearalenone has been shown to cause an earlier onset of puberty in children, endometrial adenocarcinomas, hyperplasia and breast cancer in women. Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. (A2960, A3014)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

3, 其对人类致癌性无法分类。

3, not classifiable as to its carcinogenicity to humans. (L135)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

玉米赤霉烯酮是一种生殖毒素，已被证明会导致家畜不孕、流产或其他繁殖问题。在人类中，它可能导致儿童早熟、子宫内膜腺癌、增生以及女性的乳腺癌。玉米赤霉烯酮还具有免疫毒性、基因毒性和可能导致肾脏和肝脏损伤。

Zearalenone is a reproductive toxin and has been shown to cause infertility, abortion or other breeding problems in livestock. In humans it can cause earlier onset of puberty in children, endometrial adenocarcinomas, hyperplasia, and breast cancer in women. Zearalenone is also immunotoxic, genotoxic, and can cause kidney and liver damage. (L1947, A2960)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服、皮肤、吸入和 parenteral（被污染的药物）。 (A3101)

Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性数据

LD50: >2000 mg/kg（口服，小鼠）(L1912) LD50: >500 mg/kg（腹膜内注射，小鼠）(L1912)

LD50: >2000 mg/kg (Oral, Mouse) (L1912) LD50: >500 mg/kg (Intraperitoneal, Mouse) (L1912)

来源:Toxin and Toxin Target Database (T3DB)

文献信息

• [EN] A PROCESS FOR MANUFACTURING ZERANOL<br/>[FR] PROCÉDÉ DE FABRICATION DE ZÉRANOL
  申请人：INTERVET INT BV

  公开号：WO2010115478A1

  公开（公告）日：2010-10-14

  This invention is directed generally to a process for producing Zeranol that eliminates high pressure and high temperature hydrogenations and provides high selectivity for Zeranol at improved yields.

  这项发明通常涉及一种生产Zeranol的过程，该过程消除了高压和高温氢化反应，并且在高产率下为Zeranol提供了高选择性。
• Polypeptide for the enzymatic detoxification of zearalenone, isolated polynucleotide, and associated additive, use and method
  申请人：Erber Aktiengesellschaft

  公开号：US11136561B2

  公开（公告）日：2021-10-05

  The invention relates to a polypeptide for the enzymatic detoxification of zearalenone, said polypeptide being a monooxygenase which converts the keto group in position 7 of zearalenone into an ester group, the monooxygenase in particular being an amino acid sequence selected from the group comprising sequence ID No. 1, 2 and 3 or a functional variant thereof. The functional variant and at least one of the amino acid sequences has a sequence identity of at least 60%, preferably at least 70%, more preferably at least 80% and most preferably 90%.

  本发明涉及一种对玉米赤霉烯酮进行酶解毒的多肽，所述多肽是一种单加氧酶，可将玉米赤霉烯酮第7位的酮基转化为酯基，所述单加氧酶尤其是选自序列ID No.1、2和3或其功能变体的氨基酸序列。功能变体和至少一个氨基酸序列的序列同一性至少为 60%，优选至少 70%，更优选至少 80%，最优选 90%。
• A PROCESS FOR MANUFACTURING ZERANOL
  申请人：Intervet International B.V.

  公开号：EP2417118A1

  公开（公告）日：2012-02-15
• POLYPEPTIDE FOR THE ENZYMATIC DETOXIFICATION OF ZEARALENONE, ISOLATED POLYNUCLEOTIDE, AND ASSOCIATED ADDITIVE, USE AND METHOD
  申请人：Erber Aktiengesellschaft

  公开号：US20200332269A1

  公开（公告）日：2020-10-22

  The invention relates to a polypeptide for the enzymatic detoxification of zearalenone, said polypeptide being a monooxygenase which converts the keto group in position 7 of zearalenone into an ester group, the monooxygenase in particular being an amino acid sequence selected from the group comprising sequence ID No. 1, 2 and 3 or a functional variant thereof. The functional variant and at least one of the amino acid sequences has a sequence identity of at least 60%, preferably at least 70%, more preferably at least 80% and most preferably 90%.