黄曲霉素 G1 | 1165-39-5

• 物质功能分类: 分析化学 - 标准品 - 食品和化妆品标准品
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 黄曲霉素 G1
• 中文别名: 黄曲霉素G1；黄曲霉毒素G1；黄曲霉毒素 G1
• 英文名称: aflatoxin G1
• 英文别名: 1H,12H-Furo(3',2':4,5)furo(2,3-h)pyrano(3,4-c)(1)benzopyran-1,12-dione, 3,4,7a,10a-tetrahydro-5-methoxy-, (7aR-cis)-；(3S,7R)-11-methoxy-6,8,16,20-tetraoxapentacyclo[10.8.0.02,9.03,7.013,18]icosa-1,4,9,11,13(18)-pentaene-17,19-dione
• CAS: 1165-39-5
• 化学式: C₁₇H₁₂O₇
• 分子量: 328.278
• InChiKey: XWIYFDMXXLINPU-WNWIJWBNSA-N

物化性质

• 熔点：
  244-246 °C
• 比旋光度：
  D -556° (chloroform)
• 沸点：
  386.03°C (rough estimate)
• 密度：
  1.3358 (rough estimate)
• 闪点：
  -11 °C
• 溶解度：
  DMF：可溶； DMSO：可溶；乙醇：可溶；甲醇：可溶
• LogP：
  0.679 (est)
• 颜色/状态：
  Crystals ... exhibits green fluorescence
• 蒸汽压力：
  5.86X10-11 mm Hg at 25 °C (est)
• 稳定性/保质期：
  Aflatoxins B1, B2, G1, & G2 in water or chloroform solutions or in solid films were decomposed by UV irridiation.
• 旋光度：
  Specific optical rotation (chloroform): -556 deg at 25 °C/D
• 分解：
  When heated to decomposition it emits acrid smoke and irritating fumes.
• 碰撞截面：
  181.65 Ų [M+Na]+

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

ADMET

代谢

在根霉中产生黄曲霉毒素B3...在大鼠中产生黄曲霉毒素GM1。来自表格/

Yields aflatoxin B3 in rhizopus ... yields aflatoxin gm1 in rat. From table/

来源:Hazardous Substances Data Bank (HSDB)

代谢

黄曲霉毒素B1、黄曲霉毒素B2和黄曲霉毒素G1给大鼠静脉给药后，迅速代谢成7组代谢物，其中6组通过胆汁排出。这三种毒素在2-和4-位置被羟基化。接受黄曲霉毒素G1的大鼠胆汁中含有葡萄糖苷酸。

Aflatoxin B1, aflatoxin B2, & aflatoxin G1 admin iv to rats were rapidly metabolized to 7 groups of metabolites each, 6 of which were excreted in the bile. All 3 toxins were hydroxylated at the 2- & 4-positions. Bile from the rats that had received aflatoxin G1 contained glucuronide.

来源:Hazardous Substances Data Bank (HSDB)

代谢

人类肝脏微粒体与黄曲霉毒素B1和/或黄曲霉毒素G1的孵化产生了致突变代谢物，这些代谢物在沙门氏菌泰菲默里乌姆（TA-1535/psK1002）中诱导了umuC基因的表达。基因毒性的效力排序是...黄曲霉毒素B1>黄曲霉毒素G1。微粒体激活...黄曲霉毒素在与针对p450NF的多克隆抗体共同孵化时被完全抑制，并且对p450NF（硝苯地平氧化酶）的免疫化学测定与微粒体激活...黄曲霉毒素G1和黄曲霉毒素B1相关。P450NF将...黄曲霉毒素转化为致突变代谢物，在含有纯化酶和NADPH生成系统的重组单加氧酶系统中。

...The incubation of human liver microsomes with aflatoxin B1 /or/ aflatoxin G1 ...yielded genotoxic metabolites that induced umuC gene expression in Salmonella typhimurium (TA-1535/psK1002). The rank order of genotoxic potency was ...aflatoxin B1>aflatoxin G1. Microsomal activation of the ...aflatoxins was completely inhibited upon incubation with polyclonal antibodies against p450NF, and immunochemical determinations of p450NF /(nifedipine oxidase)/ in the liver microsomal preparations were correlated with the microsomal activation of ...aflatoxin G1 and aflatoxin B1. P450NF converted the ...aflatoxins to genotoxic metabolites in a reconstituted monooxygenase system containing the purified enzyme and an NADPH generating system. ...

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

评估：有足够的人类证据表明天然存在的黄曲霉毒素混合物具有致癌性。...有足够的实验动物证据表明天然存在的黄曲霉毒素混合物以及黄曲霉毒素B1、G1和M1具有致癌性。总体评估：天然存在的黄曲霉毒素对人类具有致癌性（第1组）。/天然存在的黄曲霉毒素/

Evaluation: There is sufficient evidence in humans for the carcinogenicity of naturally occurring mixtures of aflatoxins. ... There is sufficient evidence in experimental animals for the carcinogenicity of naturally occurring mixtures of aflatoxins and aflatoxins B1, G1 and M1. Overall evaluation: Naturally occurring aflatoxins are carcinogenic to humans (Group 1). /Naturally occurring aflatoxins/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

黄曲霉毒素：已知的人类致癌物。

Aflatoxins: known to be human carcinogens. /Aflatoxins/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

职业性肝毒素 - 第二性肝毒素：在职业环境中的毒性效应潜力是基于人类摄入或动物实验的中毒病例。

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分的中毒物清除。如果患者停止呼吸，开始人工呼吸，最好使用需求阀复苏器、袋阀面罩装置或口袋面罩，按训练操作。如有必要，执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果发生呕吐，让患者前倾或置于左侧（如果可能的话，头部向下）以保持呼吸道畅通，防止吸入。保持患者安静，维持正常体温。寻求医疗帮助。 /毒物A和B/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 基本治疗：建立专利气道（如有需要，使用口咽或鼻咽气道）。如有必要，进行吸痰。观察呼吸不足的迹象，如有需要，协助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，并在必要时进行治疗……监测休克，并在必要时进行治疗……预计癫痫发作，并在必要时进行治疗……对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用0.9%的生理盐水（NS）连续冲洗每只眼睛……不要使用催吐剂。对于摄入，如果患者能吞咽、有强烈的呕吐反射且不流口水，则用水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释……在去污后，用干性无菌敷料覆盖皮肤烧伤……/毒药A和B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

黄曲霉毒素B1和G1及其代谢物以蛋白质结合物的形式存在于全身血液中。这种结合特异地发生在血浆白蛋白上，并且通过肝脏和肾脏细胞的酶促反应进行。白蛋白-黄曲霉毒素结合物是永久性的，结合是一个不可逆的过程。

Aflatoxins B1 & G1 & their metabolites exist in systemic blood as protein conjugates. This conjugation is specific to plasma albumin & proceeds enzymatically by liver & kidney cells. The albumin-aflatoxin conjugate is permanent & conjugation is an irreversible one.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

三组各四头大白母猪在妊娠和哺乳期间分别被喂食含有800 ppb纯化黄曲霉毒素B1（第1组）、800 ppb纯化黄曲霉毒素G1（第2组）或400 ppb B1和400 ppb G1（第3组）的饮食。一个对照组的四头母猪被喂食不含黄曲霉毒素的饮食。在分娩后五天和二十五天从第1组母猪的乳汁样本中发现了黄曲霉毒素B1和M1，黄曲霉毒素G1存在于第2组母猪的乳汁中，三种黄曲霉毒素都出现在第3组母猪的样本中。乳汁中黄曲霉毒素的浓度大约是饲料中的1000倍以下，但在分娩后的25天内有所增加。

Three groups of four Large White sows were fed diets containing either 800 ppb purified aflatoxin B1 (group 1), 800 ppb purified aflatoxin G1 (group 2) or 400 ppb B1 and 400 ppb G1 (group 3) throughout gestation and lactation. A control group of four sows was fed a diet free of aflatoxins. Aflatoxins B1 and M1 were found in milk samples taken five and 25 days after parturition from the sows of group 1, aflatoxin G1 was present in the milk of the sows of group 2 and all three aflatoxins were present in samples from the sows of group 3. The concentration of aflatoxin in the milk was about 1000-fold lower than that in the feed, but increased over the 25 days after parturition.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  6.1(a)
• 危险品标志：
  Xn,T+,F,T
• 安全说明：
  S16,S26,S28,S36,S36/37,S45,S53,S62,S7
• 危险类别码：
  R45
• WGK Germany：
  2,3
• 海关编码：
  29322090
• 危险类别：
  6.1(a)
• 危险标志：
  GHS02,GHS07
• 危险品运输编号：
  UN 3462 6
• 危险性描述：
  H225,H302 + H312 + H332,H319
• 危险性防范说明：
  P210,P280,P305 + P351 + P338

制备方法与用途

产品描述

黄曲霉毒素是黄曲霉菌（Aspergillus flavus）及寄生曲霉（A. parasiticus）中产毒菌株的代谢产物，主要包括黄曲霉毒素B1、B2、G1、G2及其衍生物M1、M2、P1、B2a和G2a等。这些化合物结构相似，其中M1和M2是黄曲霉毒素B1和B2的衍生物。据报道，黄曲霉菌主要产生黄曲霉毒素B1和B2，而寄生曲霉则主要产生黄曲霉毒素G1、G2、B1和B2。我国食品的主要污染菌为黄曲霉菌。

黄曲霉毒素主要污染粮、油及其制品，如花生、花生油、玉米、大米、棉子等。除此以外，核桃、杏仁、榛子、高粱、小麦、黄豆及豆类、马铃薯、蛋、乳及乳制品、肝、香肠或鱼干及辣椒等也均有可能受到污染。根据我国大规模普查食品污染的资料来看，南方高温、高湿地区的粮油及其制品易受污染，而华北、东北、西北地区除个别样品外，一般不会受到黄曲霉毒素的污染。

生物活性

Aflatoxin G1 是一种自然界中产生的黄曲霉毒素，由Aspergillus flavus 和 Aspergillus parasiticus 等霉菌产生。这些毒素在饲料、坚果、葡萄酒、香料和其他粮食作物中被发现，并具有致肝、致畸和致癌的特性。

类别

有毒物品

毒性分级

剧毒

急性毒性

• 腹腔注射 - 大鼠 LD50：14.9 毫克/公斤
• 口服 - 鸭子 LD50: 2.45 毫克/公斤

燃烧危险特性

可燃；燃烧释放刺激烟雾

储运特性

库房应通风、低温干燥，并与食品原料分开存放

灭火剂

干粉、泡沫、砂土、二氧化碳，或使用雾状水进行灭火

反应信息

• 作为反应物：
  描述：

  黄曲霉素 G1 在 水 作用下， 反应 0.5h， 生成 aflatoxin G_2a
  参考文献：
  名称：

  Interference-free analysis of aflatoxin B₁and G₁in various foodstuffs using trilinear component modeling of excitation–emission matrix fluorescence data enhanced through photochemical derivatization

  摘要：

  提出了一种新的“稀释-射击”策略，该策略将自重交替归一化残差拟合算法与光化学衍生增强的二维荧光检测相结合，用于快速分析黄曲霉毒素B1和G1。

  DOI：

  10.1039/c5ra26549e
• 作为产物：
  描述：

  黄曲霉毒素 B1 生成 黄曲霉素 G1
  参考文献：
  名称：

  LAI, F. Y.;DIMSON, P.;WEHR, C. T., PITTSBURGH CONF. AND EXPO. ANAL. CHEM. AND APPL. SPECTROSC., NEW ORLEANS,+

  摘要：

  DOI：

文献信息

• Use of Isotope-Labeled Aflatoxins for LC-MS/MS Stable Isotope Dilution Analysis of Foods
  作者：Christian Cervino、Stefan Asam、Dietmar Knopp、Michael Rychlik、Reinhard Niessner

  DOI：10.1021/jf073231z

  日期：2008.3.1

  stable isotope dilution assay (SIDA) for the determination of aflatoxins in foods was developed. The development of this method was enabled by easily accessible isotope-labeled (deuterated) aflatoxins B2 and G2, which were synthesized by catalytic deuteration of aflatoxin B1 and G1, purified, and well-characterized by NMR and MS. All four aflatoxins of interest (B1, B2, G1, and G2) were quantified in food

  黄曲霉毒素是一组高度致癌的真菌毒素，可在多种食品中找到，包括坚果，谷物和香料。在这项研究中，开发了第一种用于测定食品中黄曲霉毒素的LC-MS / MS稳定同位素稀释法（SIDA）。这种方法的发展是通过容易获得的同位素标记（氘化）黄曲霉毒素B2和G2促成的，黄曲霉毒素B2和G2通过黄曲霉毒素B1和G1的催化氘化反应合成，纯化并通过NMR和MS很好地表征。通过使用这两种标记的内标对食品中所有感兴趣的四种黄曲霉毒素（B1，B2，G1和G2）进行定量。线性校正的响应因子（RF）显示为与基质无关，与标记的黄曲霉毒素B2 /黄曲霉毒素B2和标记的黄曲霉毒素G2 /黄曲霉毒素G2无关。对于标记的黄曲霉毒素B 2 /黄曲霉毒素B 1和标记的黄曲霉毒素B2 /黄曲霉毒素G1，对模型矩阵杏仁和小麦粉进行了基质匹配的校准，显示了RF的显着差异。检测限（LOD）通过在两种模型基质存在下采用统计学方法确定，分别为0
• Novel Aflatoxin Derivatives and Protein Conjugates
  作者：Christian Cervino、Dietmar Knopp、Michael Weller、Reinhard Niessner

  DOI：10.3390/12030641

  日期：——

  Aflatoxins, a group of structurally related mycotoxins, are well known for their toxic and carcinogenic effects in humans and animals. Aflatoxin derivatives and protein conjugates are needed for diverse analytical applications. This work describes a reliable and fast synthesis of novel aflatoxin derivatives, purification by preparative HPLC and characterisation by ESI-MS and one- and two-dimensional NMR. Novel aflatoxin bovine serum albumin conjugates were prepared and characterised by UV absorption and MALDI-MS. These aflatoxin protein conjugates are potentially interesting as immunogens for the generation of aflatoxin selective antibodies with novel specificities.

  黄曲霉毒素是一组结构相关的真菌毒素，以其对人类和动物的毒性和致癌作用而闻名。需要黄曲霉毒素衍生物和蛋白质结合物来进行各种分析应用。本研究描述了一种可靠且快速的新型黄曲霉毒素衍生物合成方法，通过制备性高效液相色谱纯化并通过ESI-MS和一维、二维NMR进行表征。制备了新型黄曲霉毒素牛血清白蛋白结合物，并通过UV吸收和MALDI-MS进行表征。这些黄曲霉毒素蛋白质结合物有望作为免疫原，产生具有新特异性的黄曲霉毒素选择性抗体。
• Kinetic and mechanistic investigations on reductions of aflatoxins by lactic acid
  作者：Ram S. Shukla、Ramtej J. Verma、Daxa N. Mehta

  DOI：10.1016/s0960-894x(02)00533-4

  日期：2002.10

  ion concentration. The experimental results are interpreted in terms of mechanisms involving an initial formation of transient oxonium intermediate, which tends to polarize the olefinic (C=C) carbon, which in turn causes the hydride abstraction from alpha-carbon atom of lactic acid in rate determining step. The proposed mechanisms involve an overall transfer of two protons and two electrons from lactic

  已研究了在稀酸性水溶液（pH 3.35-4.50）中乳酸对AFB（1）还原为AFB（2）和AFG（1）还原为AFG（2）的动力学随乳酸浓度的变化，AFB（1），AFG（1）和37°C的氢离子。发现反应速率相对于乳酸和黄曲霉毒素的浓度为一阶，并且与氢离子浓度无关。用涉及初始形成的瞬态氧鎓中间体的机理解释了实验结果，该中间体倾向于极化烯烃（C = C）碳，这反过来导致速率确定步骤中从乳酸的α-碳原子提取氢化物。
• BAERTSCHI, STEVEN W.;RANEY, KEVIN D.;SHIMADA, TSUTOMU;HARRIS, THOMAS M.;G+, CHEM. RES. TOXICOL., 2,(1989) N, C. 114-122
  作者：BAERTSCHI, STEVEN W.、RANEY, KEVIN D.、SHIMADA, TSUTOMU、HARRIS, THOMAS M.、G+

  DOI：——

  日期：——
• LAI, F. Y.;DIMSON, P.;WEHR, C. T., PITTSBURGH CONF. AND EXPO. ANAL. CHEM. AND APPL. SPECTROSC., NEW ORLEANS,+
  作者：LAI, F. Y.、DIMSON, P.、WEHR, C. T.

  DOI：——

  日期：——

表征谱图