O-甲基柄曲菌素 | 17878-69-2

• 物质功能分类: 有机原料 - 醚类化合物及其衍生物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 杂色曲霉素
• 中文名称: O-甲基柄曲菌素
• 中文别名: O-甲基杂色曲霉素
• 英文名称: O-methylsterigmatocystin
• 英文别名: 8-O-Methylsterigmatocystin；(3S,7R)-11,15-dimethoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14(19),15,17-heptaen-13-one
• CAS: 17878-69-2
• 化学式: C₁₉H₁₄O₆
• 分子量: 338.317
• InChiKey: JKUJKKGMOZDDJV-ZRNGKTOUSA-N

物化性质

• 熔点：
  265℃
• 沸点：
  564.7±50.0 °C(Predicted)
• 密度：
  1.407±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：可溶；二甲基亚砜：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

制备方法与用途

O-甲基杂色曲霉素是一种真菌毒素，广泛存在于谷物及其制品中。这类生物毒素是由真菌产生的有毒次生代谢产物。

反应信息

• 作为反应物：
  描述：

  O-甲基柄曲菌素 在 还原型辅酶II(NADPH)四钠盐 作用下， 以 丙酮 为溶剂， 反应 84.0h， 生成 黄曲霉毒素 B1
  参考文献：
  名称：

  Evidence for the Probable Final Steps in Aflatoxin Biosynthesis

  摘要：

  The final steps in the biosynthesis of the potent environmental carcinogen aflatoxin B-1 (8) are believed to involve the oxidative cleavage and rearrangement of O-methylsterigmatocystin (7) with loss of a C-1-unit. The means by which this overall transformation occurs is not known and has been addressed using cell-free conversions of samples of radiolabeled 7 that were obtained by the incorporation of either [1-C-14]- or [2-C-14]acetate. The proportion of radioisotope detected in aflatoxin B-1 relative to that of the C-1-unit liberated (formaldehyde, formic acid, or carbon dioxide) was tested. [C-14]Carbon dioxide alone was isolated in the proper stoichiometry to limit the possible mechanisms that can be acting at the conclusion of this biosynthetic pathway.

  DOI：

  10.1021/jo00095a016
• 作为产物：
  描述：

  柄曲菌素 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以77%的产率得到O-甲基柄曲菌素
  参考文献：
  名称：

  Evidence for the Probable Final Steps in Aflatoxin Biosynthesis

  摘要：

  The final steps in the biosynthesis of the potent environmental carcinogen aflatoxin B-1 (8) are believed to involve the oxidative cleavage and rearrangement of O-methylsterigmatocystin (7) with loss of a C-1-unit. The means by which this overall transformation occurs is not known and has been addressed using cell-free conversions of samples of radiolabeled 7 that were obtained by the incorporation of either [1-C-14]- or [2-C-14]acetate. The proportion of radioisotope detected in aflatoxin B-1 relative to that of the C-1-unit liberated (formaldehyde, formic acid, or carbon dioxide) was tested. [C-14]Carbon dioxide alone was isolated in the proper stoichiometry to limit the possible mechanisms that can be acting at the conclusion of this biosynthetic pathway.

  DOI：

  10.1021/jo00095a016

文献信息

• New mycotoxins from the scale insect fungus Aschersonia coffeae Henn. BCC 28712
  作者：Jittra Kornsakulkarn、Siriporn Saepua、Kitlada Srichomthong、Sumalee Supothina、Chawanee Thongpanchang

  DOI：10.1016/j.tet.2012.07.059

  日期：2012.10

  anthraquinones 7–9, together with nine known compounds; sterigmatocystin (10), demethylsterigmatocystin (11), dihydrodemethylsterigmatocystin (12), sterigmatin (13), austocystin F (14), averufin (15), aflatoxin B1, paeciloquinone A, and zeorin, were isolated from the scale insect fungus Aschersonia coffeae Henn. BCC 28712. The structures of these compounds were elucidated using NMR spectroscopic and

  九种新的霉菌毒素；5个呫1 - 5，hydroxanthone 6，和三个蒽醌7 - 9，连同9种已知化合物; 杂色曲霉素（10），demethylsterigmatocystin（11），dihydrodemethylsterigmatocystin（12），sterigmatin（13），austocystin F（14），averufin（15），黄曲霉毒素B1，paeciloquinone A，和zeorin，从该介壳虫真菌分离座壳孢coffeae Henn的。BCC28712。使用NMR光谱和MS光谱分析阐明了这些化合物的结构。化合物1– 3和6 – 9表现出细胞毒活性，而黄酮2和蒽醌8和9也表现出抗疟活性。
• COMPOUNDS FOR INHIBITION OF FUNGAL MYCOTOXIN AND SPORULATION
  申请人：Strasburg Gale M.

  公开号：US20180192648A1

  公开（公告）日：2018-07-12

  Compounds and compositions are described herein that inhibit the biosynthesis of mycotoxins and fungal sporulation. Such compounds and compositions are useful for inhibiting mold. Methods of using such compounds and compositions are also described herein that involve applying the compositions to plants, plant parts, structures, containers, and other surfaces.

  本文描述了一些化合物和组合物，可以抑制霉菌毒素的生物合成和真菌孢子的形成。这些化合物和组合物对于抑制霉菌非常有用。本文还描述了使用这些化合物和组合物的方法，包括将它们应用于植物、植物部分、结构、容器和其他表面。
• 4,7-Diazaindole derivatives and their use as fungicides
  申请人：Bayer CropScience AG

  公开号：EP2338890A1

  公开（公告）日：2011-06-29

  The present invention relates to compounds of formula (I) their process of preparation, their use for preventing and/or controlling fungal infection in plants and/or plant propagation material and for reducing mycotoxin contamination in plants or plant material, and compositions containing these compounds.

  本发明涉及式(I)化合物及其制备方法，用于预防和/或控制植物和/或植物繁殖材料的真菌感染，以及减少植物或植物材料中霉菌毒素污染的用途，以及含有这些化合物的组合物。
• Two distinct O-methyltransferases in aflatoxin biosynthesis
  作者：K Yabe、Y Ando、J Hashimoto、T Hamasaki

  DOI：10.1128/aem.55.9.2172-2177.1989

  日期：1989.9

  The substances belonging to the sterigmatocystin group bear a close structural relationship to aflatoxins. When demethylsterigmatocystin (DMST) was fed to Aspergillus parasiticus NIAH-26, which endogenously produces neither aflatoxins nor precursors in YES medium, aflatoxins B1 and G1 were produced. When dihydrodemethylsterigmatocystin (DHDMST) was fed to this mutant, aflatoxins B2 and G2 were produced. Results of the cell-free experiment with S-adenosyl-[methyl-3H]methionine showed that first the C-6-OH groups of DMST and DHDMST are methylated to produce sterigmatocystin and dihydrosterigmatocystin (O-methyltransferase I) and then the C-7-OH groups are methylated to produce O-methylsterigmatocystin (OMST) and dihydro-O-methylsterigmatocystin (DHOMST) (O-methyltransferase II). However, no methyltransferase activity was observed when either OMST, DHOMST, 5,6-dimethoxysterigmatocystin, 5-methoxysterigmatocystin, or sterigmatin was incubated with the cell extract. Treatment of the cell extract with N-ethylmaleimide inhibited O-methyltransferase I activity but not that of O-methyltransferase II. Furthermore, these O-methyltransferases were different in their protein molecules and were involved in both the reactions from DMST to OMST and DHDMST to DHOMST. The reactions described in this paper were not observed when the same mold had been cultured in YEP medium.

  属于青霉毒素组的物质与黄曲霉毒素有密切的结构关系。将去甲基青霉毒素（DMST）喂食给内源性在YES培养基中既不产生黄曲霉毒素也不产生前体的寄生曲霉菌NIAH-26时，产生了黄曲霉毒素B1和G1。将二氢去甲基青霉毒素（DHDMST）喂食给这种突变体时，产生了黄曲霉毒素B2和G2。使用S-腺苷甲硫氨酸-[甲基-3H]进行的细胞外实验结果表明，首先将DMST和DHDMST的C-6-OH基甲基化，产生青霉毒素和二氢青霉毒素（O-甲基转移酶I），然后将C-7-OH基甲基化，产生O-甲基青霉毒素和二氢-O-甲基青霉毒素（O-甲基转移酶II）。然而，当将O-甲基青霉毒素、DHOMST、5,6-二甲氧基青霉毒素、5-甲氧基青霉毒素或青霉亚素与细胞提取物孵育时，没有观察到甲基转移酶活性。将细胞提取物用N-乙酰丙烯酰亚胺处理，抑制了O-甲基转移酶I的活性，但没有抑制O-甲基转移酶II的活性。此外，这些O-甲基转移酶在其蛋白质分子上有所不同，并参与了从DMST到OMST和从DHDMST到DHOMST的两个反应。当同一种霉菌在YEP培养基中培养时，本文描述的反应未被观察到。
• Identification of O-methylsterigmatocystin as an aflatoxin B1 and G1 precursor in Aspergillus parasiticus
  作者：D Bhatnagar、S P McCormick、L S Lee、R A Hill

  DOI：10.1128/aem.53.5.1028-1033.1987

  日期：1987.5

  G1 were produced; 10 nmol of OMST produced 7.8 nmol of B1 and 1.0 nmol of G1, while 10 nmol of ST produced 6.4 nmol of B1 and 0.6 nmol of G1. A time course study of aflatoxin synthesis in ST feeding experiments with AVN-1 revealed that OMST is synthesized by the mold during the onset of aflatoxin synthesis. The total amount of aflatoxins recovered from OMST feeding experiments was higher than from

  分离的寄生曲霉CP461（SRRC 2043）没有产生可检出的黄曲霉毒素，但积累了O-甲基甾体藻毒素（OMST）。当在低糖培养基中将葡萄球菌毒素（ST）喂入该分离株时，OMST的积累增加，而没有黄曲霉毒素的合成。当将放射性标记的[14C] OMST喂入产寄生虫的非黄曲霉毒素，非ST-和非OMST突变体AVN-​​1（SRRC 163）的静息菌丝体时，用14C标记的黄曲霉毒素B1和G1产生 10nmol OMST产生7.8nmol B1和1.0nmol G1，而10nmol ST产生6.4nmol B1和0.6nmol G1。在AVN-1的ST饲喂实验中对黄曲霉毒素合成的时程研究表明，OMST是在黄曲霉毒素合成开始时由霉菌合成的。从OMST饲喂实验中回收的黄曲霉毒素总量高于将ST饲喂至静息菌丝体的实验。这些结果表明，OMST是黄曲霉毒素和黄曲霉毒素B1和G1之间黄曲霉毒素生物合成途径中的真正