黄曲霉毒素B1谷胱甘肽缀合物的一些质谱和核磁共振分析研究。
Some mass-spectral and n.m.r. analytical studies of a glutathione conjugate of aflatoxin B1.
作者信息
Moss E J, Judah D J, Przybylski M, Neal G E
出版信息
Biochem J. 1983 Jan 15;210(1):227-33. doi: 10.1042/bj2100227.
Abstract
A system for the formation of an aflatoxin B1-reduced glutathione conjugate in vitro was developed, capable of yielding 80% conversion of aflatoxin B1 into the conjugate. A reverse-phase high-pressure-liquid-chromatography system was also devised that not only facilitates improved resolution of the compound but that, by manipulation of the pH, is also capable of an extensive purification of the compound from other aflatoxin B1 metabolites in a single step. Material produced by these techniques, after further purification, has been used in 1H-n.m.r. and mass-spectroscopic studies. Results were obtained that support the proposed linkage of the aflatoxin B1 to reduced glutathione in a 1:1 molar ratio via a thioether linkage. Amino acid analyses were also consistent with this structure. The absence of a Schiff-base linkage of aflatoxin B1 8,9-dihydrodiol to glutamate was further demonstrated by the presence of a gamma-glutamyltransferase-catalysed-transferable glutamate moiety. These data are consistent with the structure 8,9-dihydro-8-(S-glutathionyl)-9-hydroxy-aflatoxin B1.
摘要
开发了一种体外形成黄曲霉毒素B1 - 还原型谷胱甘肽缀合物的系统，该系统能够将80%的黄曲霉毒素B1转化为缀合物。还设计了一种反相高压液相色谱系统，该系统不仅有助于提高化合物的分离度，而且通过调节pH值，还能够在一步中从其他黄曲霉毒素B1代谢物中对该化合物进行广泛纯化。通过这些技术产生的材料经过进一步纯化后，已用于核磁共振和质谱研究。获得的结果支持了黄曲霉毒素B1与还原型谷胱甘肽以1:1摩尔比通过硫醚键连接的提议。氨基酸分析也与该结构一致。γ-谷氨酰转移酶催化的可转移谷氨酸部分的存在进一步证明了黄曲霉毒素B1 8,9 - 二氢二醇与谷氨酸不存在席夫碱连接。这些数据与8,9 - 二氢 - 8 -（S - 谷胱甘肽基）- 9 - 羟基 - 黄曲霉毒素B1的结构一致。
相似文献
1
Some mass-spectral and n.m.r. analytical studies of a glutathione conjugate of aflatoxin B1.黄曲霉毒素B1谷胱甘肽缀合物的一些质谱和核磁共振分析研究。
Biochem J. 1983 Jan 15;210(1):227-33. doi: 10.1042/bj2100227.
2
The mercapturic acid pathway metabolites of a glutathione conjugate of aflatoxin B1.黄曲霉毒素B1谷胱甘肽共轭物的硫醚氨酸途径代谢产物。
Chem Biol Interact. 1985 Oct;55(1-2):139-55. doi: 10.1016/s0009-2797(85)80124-1.
3
The major metabolite of aflatoxin B1 in the rat is a glutathione conjugate.
Chem Biol Interact. 1978 Sep;22(2-3):239-55. doi: 10.1016/0009-2797(78)90129-1.
4
Oxidation of aflatoxins and sterigmatocystin by human liver microsomes: significance of aflatoxin Q1 as a detoxication product of aflatoxin B1.黄曲霉毒素和杂色曲霉素在人肝微粒体中的氧化作用：黄曲霉毒素Q1作为黄曲霉毒素B1解毒产物的意义。
Chem Res Toxicol. 1992 Mar-Apr;5(2):202-10. doi: 10.1021/tx00026a009.
5
Metabolic basis of the species difference to aflatoxin B1 induced hepatotoxicity.物种对黄曲霉毒素B1诱导的肝毒性差异的代谢基础。
Biochem Biophys Res Commun. 1983 Jul 29;114(2):813-21. doi: 10.1016/0006-291x(83)90854-9.
6
Structural identification of the major DNA adduct formed by aflatoxin B1 in vitro.黄曲霉毒素B1体外形成的主要DNA加合物的结构鉴定。
Proc Natl Acad Sci U S A. 1977 May;74(5):1870-4. doi: 10.1073/pnas.74.5.1870.
7
The formation of 2,3-dihydroxy-2,3-dihydro-aflatoxin B1 by the metabolism of aflatoxin B1 by liver microsomes isolated from certain avian and mammalian species and the possible role of this metabolite in the acute toxicity of aflatoxin B1.从某些禽类和哺乳动物物种中分离出的肝微粒体对黄曲霉毒素B1进行代谢生成2,3 - 二羟基 - 2,3 - 二氢黄曲霉毒素B1，以及该代谢产物在黄曲霉毒素B1急性毒性中可能发挥的作用。
Toxicol Appl Pharmacol. 1981 May;58(3):431-7. doi: 10.1016/0041-008x(81)90095-8.
8
Some high-performance liquid-chromatographic studies of the metabolism of aflatoxins by rat liver microsomal preparations.大鼠肝脏微粒体制剂对黄曲霉毒素代谢的一些高效液相色谱研究。
Biochem J. 1978 Sep 15;174(3):839-51. doi: 10.1042/bj1740839.
9
Synthesis and characterization of aflatoxin B1 mercapturic acids and their identification in rat urine.
Chem Res Toxicol. 1997 Oct;10(10):1144-51. doi: 10.1021/tx960161+.
10
Metabolic basis for the protective effect of the antioxidant ethoxyquin on aflatoxin B1 hepatocarcinogenesis in the rat.抗氧化剂乙氧喹对大鼠黄曲霉毒素B1肝癌发生保护作用的代谢基础。
Cancer Res. 1987 Oct 1;47(19):5218-23.
引用本文的文献
1
Bioactivation and Regioselectivity of Pig Cytochrome P450 3A29 towards Aflatoxin B₁.猪细胞色素P450 3A29对黄曲霉毒素B₁的生物活化和区域选择性
Toxins (Basel). 2016 Sep 12;8(9):267. doi: 10.3390/toxins8090267.
2
Multiple scan modes in the hybrid tandem mass spectrometric screening and characterization of the glutathione conjugate of 2-furamide.多种扫描模式在 2-呋喃甲酰胺半胱氨酸轭合物的混合串联质谱筛选和表征中的应用。
J Am Soc Mass Spectrom. 1991 Jan;2(1):55-68. doi: 10.1016/1044-0305(91)80061-B.
3
Synergistic effect ofSacoglottis gabonensis bark extract.萨戈格罗蒂斯加蓬树皮提取物的协同作用。
Mycotoxin Res. 1988 Mar;4(1):37-43. doi: 10.1007/BF03192088.
4
Interaction of the mycotoxin penicillic acid with glutathione and rat liver glutathione S-transferases.霉菌毒素青霉酸与谷胱甘肽及大鼠肝脏谷胱甘肽S-转移酶的相互作用。
Mycopathologia. 1984 Jun 30;86(3):137-41. doi: 10.1007/BF00441121.
5
Aflatoxin metabolism in humans: detection of metabolites and nucleic acid adducts in urine by affinity chromatography.人类中的黄曲霉毒素代谢：通过亲和色谱法检测尿液中的代谢产物和核酸加合物。
Proc Natl Acad Sci U S A. 1985 Oct;82(19):6492-6. doi: 10.1073/pnas.82.19.6492.
6
Ethoxyquin-induced resistance to aflatoxin B1 in the rat is associated with the expression of a novel alpha-class glutathione S-transferase subunit, Yc2, which possesses high catalytic activity for aflatoxin B1-8,9-epoxide.乙氧喹诱导大鼠对黄曲霉毒素B1产生抗性与一种新型α类谷胱甘肽S-转移酶亚基Yc2的表达有关，该亚基对黄曲霉毒素B1-8,9-环氧化物具有高催化活性。
Biochem J. 1991 Oct 15;279 ( Pt 2)(Pt 2):385-98. doi: 10.1042/bj2790385.
7
The isolation and culture of DHBV-infected embryo and duckling hepatocytes and the effect of aflatoxin B1 or irradiation on these cells.鸭乙肝病毒感染的胚胎和雏鸭肝细胞的分离培养以及黄曲霉毒素B1或辐射对这些细胞的影响。
Br J Cancer. 1991 Mar;63(3):378-85. doi: 10.1038/bjc.1991.89.
8
Molecular cloning and heterologous expression of a cDNA encoding a mouse glutathione S-transferase Yc subunit possessing high catalytic activity for aflatoxin B1-8,9-epoxide.编码对黄曲霉毒素B1-8,9-环氧化物具有高催化活性的小鼠谷胱甘肽S-转移酶Yc亚基的cDNA的分子克隆及异源表达
Biochem J. 1992 Jul 1;285 ( Pt 1)(Pt 1):173-80. doi: 10.1042/bj2850173.
本文引用的文献
1
Inhibition of microsome-mediated binding of aflatoxin B1 to DNA by glutathione S-transferase.谷胱甘肽S-转移酶对微粒体介导的黄曲霉毒素B1与DNA结合的抑制作用。
Cancer Lett. 1980 Apr;9(2):143-9. doi: 10.1016/0304-3835(80)90118-4.
2
Species difference in the binding of aflatoxin B1 to hepatic macromolecules.黄曲霉毒素B1与肝脏大分子结合的种属差异。
Toxicol Appl Pharmacol. 1980 Jan;52(1):177-80. doi: 10.1016/0041-008x(80)90257-4.
3
Formation and identification of glutathione conjugates from 2-nitrosofluorene and N-hydroxy-2-aminofluorene.由2-亚硝基芴和N-羟基-2-氨基芴形成并鉴定谷胱甘肽缀合物
Chem Biol Interact. 1982 Mar 1;39(1):111-27. doi: 10.1016/0009-2797(82)90010-2.
4
Identification and quantitation of methotrexate and methotrexate metabolites in clinical high-dose therapy by high pressure liquid chromatography and field desorption mass spectrometry.通过高压液相色谱法和场解吸质谱法对临床大剂量治疗中的甲氨蝶呤及其代谢产物进行鉴定和定量分析。
Biomed Mass Spectrom. 1982 Jan;9(1):22-32. doi: 10.1002/bms.1200090106.
5
Mechanism of the resistance to cytotoxicity which precedes aflatoxin B1 hepatocarcinogenesis.黄曲霉毒素B1诱导肝癌发生之前对细胞毒性产生抗性的机制。
Carcinogenesis. 1981;2(5):457-61. doi: 10.1093/carcin/2.5.457.
6
Differences in aflatoxin B1-susceptibility of rat and mouse are correlated with the capability in vitro to inactivate aflatoxin B1-epoxide.
Carcinogenesis. 1981;2(4):299-306. doi: 10.1093/carcin/2.4.299.
7
The formation of 2,3-dihydroxy-2,3-dihydro-aflatoxin B1 by the metabolism of aflatoxin B1 by liver microsomes isolated from certain avian and mammalian species and the possible role of this metabolite in the acute toxicity of aflatoxin B1.从某些禽类和哺乳动物物种中分离出的肝微粒体对黄曲霉毒素B1进行代谢生成2,3 - 二羟基 - 2,3 - 二氢黄曲霉毒素B1，以及该代谢产物在黄曲霉毒素B1急性毒性中可能发挥的作用。
Toxicol Appl Pharmacol. 1981 May;58(3):431-7. doi: 10.1016/0041-008x(81)90095-8.
8
A comparison of the effects of pretreatment with phenobarbitone and 3-methylcholanthrene on the metabolism of aflatoxin B1 by rat liver microsomes and isolated hepatocytes in vitro.苯巴比妥和3-甲基胆蒽预处理对大鼠肝微粒体和离体肝细胞体外代谢黄曲霉毒素B1的影响比较。
Chem Biol Interact. 1981 May;35(2):145-57. doi: 10.1016/0009-2797(81)90139-3.
9
10
Effect of microsomally activated AFB1 on GGT activity in 3 rat liver cell lines.微粒体激活的黄曲霉毒素B1对3种大鼠肝细胞系中γ-谷氨酰转移酶活性的影响。
Br J Cancer. 1982 Jun;45(6):945-52. doi: 10.1038/bjc.1982.147.
Zotero 插件