1-(3,5-dihydroxyphenyl)-10'-hydroxy-1'E-undecen-6'-one

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-(3,5-dihydroxyphenyl)-10'-hydroxy-1'E-undecen-6'-one
• 英文别名: (E)-1-(3,5-dihydroxyphenyl)-10-hydroxy-1-undecen-6-one；(1e,10s)-1-(3,5-Dihydroxyphenyl)-10-Hydroxyundec-1-En-6-One；(E,10S)-1-(3,5-dihydroxyphenyl)-10-hydroxyundec-1-en-6-one
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: TVXRLKRGDWQGQV-MXPWBENCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  玉米烯酮 在 碳酸氢钠 作用下， 以 水 为溶剂， 生成 1-(3,5-dihydroxyphenyl)-10'-hydroxy-1'E-undecen-6'-one
  参考文献：
  名称：

  Biotransformation of the Mycotoxin, Zearalenone, to a Non-estrogenic Compound by a Fungal Strain ofClonostachyssp.

  摘要：

  Zearalenone（玉米赤霉烯酮）是一种具有雌激素活性的真菌毒素，由一个间苯二酚部分与一个14元大环内酯环融合而成，由多种镰刀菌属物种产生。我们发现，Clonostachys rosea IFO 7063能够有效地将玉米赤霉烯酮（1）转化为断裂产物（2），即1-(3,5-二羟基苯基)-10′-羟基-1′E-十一碳烯-6′-酮。此外，断裂产物2在人乳腺癌MCF-7细胞增殖试验中并未表现出与1及17β-雌二醇相似的强雌激素活性。

  DOI：

  10.1271/bbb.66.2723

文献信息

• Biotransformation of the Mycotoxin Zearalenone to its Metabolites Hydrolyzed Zearalenone (HZEN) and Decarboxylated Hydrolyzed Zearalenone (DHZEN) Diminishes its Estrogenicity In Vitro and In Vivo
  作者：Sebastian Fruhauf、Barbara Novak、Veronika Nagl、Matthias Hackl、Doris Hartinger、Valentina Rainer、Silvia Labudová、Gerhard Adam、Markus Aleschko、Wulf-Dieter Moll、Michaela Thamhesl、Bertrand Grenier

  DOI：10.3390/toxins11080481

  日期：——

  Zearalenone (ZEN)-degrading enzymes are a promising strategy to counteract the negative effects of this mycotoxin in livestock. The reaction products of such enzymes need to be thoroughly characterized before technological application as a feed additive can be envisaged. Here, we evaluated the estrogenic activity of the metabolites hydrolyzed zearalenone (HZEN) and decarboxylated hydrolyzed zearalenone

  玉米赤霉烯酮（ZEN）降解酶是一种有前景的策略，可以抵消这种霉菌毒素对家畜的负面影响。在可以设想作为饲料添加剂的技术应用之前，需要彻底表征此类酶的反应产物。在这里，我们评估了由玉米赤霉烯酮-内酰胺酶Zhd101p水解ZEN形成的代谢产物水解玉米赤霉烯酮（HZEN）和脱羧水解玉米赤霉烯酮（DHZEN）的雌激素活性。ZEN，HZEN和DHZEN在两个体外模型中进行了测试：MCF-7细胞增殖测定（0.01-500 nM）和雌激素敏感性酵母生物测定（1-10,000 nM）。此外，我们比较了饮食中ZEN的影响（4。58 mg / kg）和等摩尔日粮浓度的HZEN和DHZEN对雌性仔猪的生殖道形态以及子宫mRNA和microRNA表达的影响（n = 6，暴露4周）。尽管ZEN增加了细胞增殖和报告基因的转录，但HZEN和DHZEN均未引发雌激素反应，这表明这些代谢产物的体外雌激素水平至少比ZEN低50-10
• Polypeptide for hydrolytic cleavage of zearalenone and/or zearalenone derivatives, isolated polynucleotide thereof as well as a polypeptide containing an additive, use of same as well as a process
  申请人：Erber Aktiengesellschaft

  公开号：US10779556B2

  公开（公告）日：2020-09-22

  The invention relates to a polypeptide for the hydrolytic cleavage of zearalenone and/or at least one zearalenone derivative, said polypeptide being a hydrolase having an amino acid sequence selected from the group consisting of SEQ ID NO: 1-15 or a functional variant thereof, wherein the sequence of the functional variant is at least 40% identical to at least one of the amino acid sequences. The invention also relates to: an additive containing the polypeptide; an isolated polynucleotide that encodes the polypeptide; and a method for the hydrolytic cleavage of zearalenone and/or of at least one zearalenone derivative using the polypeptide.

  本发明涉及一种用于水解裂解玉米赤霉烯酮和/或至少一种玉米赤霉烯酮衍生物的多肽，所述多肽是一种水解酶，其氨基酸序列选自 SEQ ID NO: 1-15 或其功能变体组成的组，其中功能变体的序列与至少一个氨基酸序列至少有 40%相同。本发明还涉及：含有该多肽的添加剂；编码该多肽的分离多核苷酸；以及使用该多肽水解裂解玉米赤霉烯酮和/或至少一种玉米赤霉烯酮衍生物的方法。
• POLYPEPTIDE FOR HYDROLYTIC CLEAVAGE OF ZEARALENONE AND/OR ZEARALENONE DERIVATIVES, ISOLATED POLYNUCLEOTIDE THEREOF AS WELL AS A POLYPEPTIDE CONTAINING AN ADDITIVE, USE OF SAME AS WELL AS A PROCESS
  申请人：Erber Aktiengesellschaft

  公开号：US20190124948A1

  公开（公告）日：2019-05-02

  The invention relates to a polypeptide for the hydrolytic cleavage of zearalenone and/or at least one zearalenone derivative, said polypeptide being a hydrolase having an amino acid sequence selected from the group consisting of SEQ ID NO: 1-15 or a functional variant thereof, wherein the sequence of the functional variant is at least 40% identical to at least one of the amino acid sequences. The invention also relates to: an additive containing the polypeptide; an isolated polynucleotide that encodes the polypeptide; and a method for the hydrolytic cleavage of zearalenone and/or of at least one zearalenone derivative using the polypeptide.
• MEANS AND METHODS FOR CLEAVAGE OF ZEARALENONE
  申请人：ERBER AKTIENGESELLSCHAFT

  公开号：US20210371835A1

  公开（公告）日：2021-12-02

  The present invention relates to a method for increasing the stability of an α/β-hydrolase. In addition, the present invention relates to an α/β-hydrolase obtainable by the method of the present invention. Also provided are α/β-hydrolases having a decreased grand average of hydropathy (GRAVY) value and/or comprising specific mutations. In addition, the present invention concerns a use of an α/β-hydrolase of the present invention for degrading zearalenone (ZEN).
• Biotransformation of the Mycotoxin, Zearalenone, to a Non-estrogenic Compound by a Fungal Strain of<i>Clonostachys</i>sp.
  作者：Hideaki KAKEYA、Naoko TAKAHASHI-ANDO、Makoto KIMURA、Rie ONOSE、Isamu YAMAGUCHI、Hiroyuki OSADA

  DOI：10.1271/bbb.66.2723

  日期：2002.1

  Zearalenones are mycotoxins with estrogenic activity consisting of a resorcinol moiety fused to a 14-membered macrocyclic lactone and are produced by various Fusarium species. We found that Clonostachys rosea IFO 7063 was effectively capable of converting zearalenone (1) to cleavage product (2), 1-(3,5-dihydroxyphenyl)-10′-hydroxy-1′E-undecene-6′-one. Moreover, cleavage product 2 did not show potent estrogenic activity like that of 1 and 17β-estradiol in the human breast cancer MCF-7 cell proliferation assay.

  Zearalenone（玉米赤霉烯酮）是一种具有雌激素活性的真菌毒素，由一个间苯二酚部分与一个14元大环内酯环融合而成，由多种镰刀菌属物种产生。我们发现，Clonostachys rosea IFO 7063能够有效地将玉米赤霉烯酮（1）转化为断裂产物（2），即1-(3,5-二羟基苯基)-10′-羟基-1′E-十一碳烯-6′-酮。此外，断裂产物2在人乳腺癌MCF-7细胞增殖试验中并未表现出与1及17β-雌二醇相似的强雌激素活性。