Sterigmatocystin
(Synonyms: 甾体半胱氨酸) 目录号 : GC44953
Sterigmatocystin is a mycotoxin produced by fungi of the genus Aspergillus[1].
Cas No.:10048-13-2
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
| Cell experiment [1]: | |
|
Cell lines |
HEK293 cells |
|
Preparation Method |
Sterigmatocystin at varying concentrations (0-128 µM or 1-42.7 µg/mL) was mixed with HEK293 cells and incubated at 37°C for 2 days. The cytotoxic effects of sterigmatocystin on cell proliferation were measured with MTT assays, and the cells' morphology was also recorded under a light microscope in each treatment. |
|
Reaction Conditions |
0-128 µM or 1-42.7 µg/mL; at 37°C for 2 days |
|
Applications |
The results showed that sterigmatocystin did not show significant cytotoxicity to HEK 293 cell line at a concentration of 64 µM (21.3 µg/mL) or lower. The density of living cells was significantly lower when the concentration reached 128 µM, compared to that of the control. Consistently, sterigmatocystin at 128 µM caused a significantly lower density of live cells under a light microscope. |
| Animal experiment [2]: | |
|
Animal models |
male Wistar rats |
|
Preparation Method |
Sterigmatocystin and 5-methoxysterigmatocystin were intratracheally instilled in male Wistar rats using doses (0.3 mg SterigmatocystinC/kg of lung weight (l.w.); 3.6 mg 5-methoxysterigmatocystin/kg l.w.; toxin combination 0.3 + 3.6 mg/kg l.w.) that corresponded to concentrations detected in the dust of damp indoor areas in order to explore cytotoxicity, vascular permeability, immunomodulation and genotoxicity. |
|
Dosage form |
0.3 mg Sterigmatocystin/kg of lung weight (l.w.); 3.6 mg 5-methoxysterigmatocystin/kg l.w.; toxin combination 0.3 + 3.6 mg/kg l.w. |
|
Applications |
In an alkaline comet assay, both mycotoxins provoked a similar intensity of DNA damage in rat lungs, while in a neutral comet assay, only 5-M-sterigmatocystin evoked significant DNA damage. |
|
References: [1] Niu G, et al. Sterigmatocystin Limits Plasmodium falciparum Proliferation and Transmission. Pharmaceuticals (Basel). 2021 Nov 29;14(12):1238. |
|
Sterigmatocystin is a mycotoxin produced by fungi of the genus Aspergillus[1]. IC50 of sterigmatocystin against P. falciparum transmission was about 16 μg/mL or 48 μM[2]. Sterigmatocystin inhibited P. falciparum proliferation in the blood with an IC50 of 34 µM and limited the sexual parasites to infect mosquitoes with an IC50 of 48 µM[2].
In vitro, treatment with 0.78, 1.56 and 3.12 μM sterigmatocystin in human neuroblastoma (SH-SY5Y) cells for 24h induced an increase in ROS (reactive oxygen species) generation and LPO (lipid peroxidation) as well as a depletion of GSH (antioxidant no-enzymatic) levels, an increase in GSSG (oxidized to glutathione disulphide) content and a decrease in GSH/GSSG ratio at the highest concentrations[3]. In human gastric epithelial GES-1 cells, exposure to 3 µM of sterigmatocystin for 24 h induced DNA damage, which subsequently activated ATM-Chk2 and ATM-p53 signalling pathways resulting in G2 arrest[4]. In vitro, treatment with 3 and 6 μM sterigmatocystin respectively for 1 h significantly increased more DNA strand breaks and the expression level of ROS (reactive oxygen species) and 8-OHdG (8-hydroxydeoxyguanosine) in HepG2 cells[5].
In vivo, demonstrated that male Wistar rats were orally treated with a single sterigmatocystin dose (10, 20 and 40 mg/kg b.w.) increased the expression level of malondialdehyde (MDA; all sterigmatocystin doses) and catalase (CAT; 10 mg/kg b.w.) in plasma, decreased the expression level of glutathione peroxidase (GPx; 20 and 40 mg/kg b.w.) in the liver, and increased the expression level of MDA and superoxide dismutase (SOD) in kidneys (all sterigmatocystin doses)[6].
甾体半胱氨酸是由曲霉属真菌产生的一种霉菌毒素[1]。甾体半胱氨酸对恶性疟原虫传播的IC50约为16 μg/mL或48 μM[2]。甾体半胱氨酸抑制恶性疟原虫在血液中的增殖，IC50为34 μM，限制有性寄生虫感染蚊子，IC50为48 μM[2]。
体外试验表明，用0.78、1.56和3.12 μM的甾体半胱氨酸在人类神经母细胞瘤（SH-SY5Y）中处理24小时，诱发ROS（活性氧）生成和LPO（脂质过氧化）增加，以及GSH（抗氧化剂无酶）水平耗尽，GSSG（氧化为谷胱甘肽二硫化物）含量增加，最高浓度时GSH/GSSG比例下降[3]。在人类胃上皮细胞GES-1中，暴露于3 µM的甾体半胱氨酸24小时诱发DNA损伤，随后激活ATM-Chk2和ATM-p53信号通路，导致G2停滞[4]。在体外，用3和6μM的甾体半胱氨酸处理1小时，可显著增加HepG2细胞中更多的DNA链断裂以及ROS（活性氧）和8-OHdG（8-羟基脱氧鸟苷）的表达水平[5]。
体内药效试验表明，雄性Wistar大鼠口服单一剂量的甾体半胱氨酸（10、20和40 mg/kg b.w.）后，血浆中丙二醛（MDA）和过氧化氢酶（CAT；10mg/kg b.w.）的表达水平增加，过氧化氢酶（CAT）；10 mg/kg b.w.），肝脏中谷胱甘肽过氧化物酶（GPx；20和40 mg/kg b.w.）的表达水平下降，肾脏中MDA和超氧化物歧化酶（SOD）的表达水平上升[6]。
References:
[1] Zingales V, et al. Sterigmatocystin-induced cytotoxicity via oxidative stress induction in human neuroblastoma cells. Food Chem Toxicol. 2020 Feb;136:110956.
[2] Niu G, et al. Sterigmatocystin Limits Plasmodium falciparum Proliferation and Transmission. Pharmaceuticals (Basel). 2021 Nov 29;14(12):1238.
[3] Zingales V, et al. Sterigmatocystin-induced DNA damage triggers cell-cycle arrest via MAPK in human neuroblastoma cells. Toxicol Mech Methods. 2021 Sep;31(7):479-488.
[4] Dabelić S, et al. Sterigmatocystin, 5-Methoxysterigmatocistin, and Their Combinations Are Cytotoxic and Genotoxic to A549 and Hepg2 Cells and Provoke Phosphorylation of Chk2, but Not Fancd2 Checkpoint Proteins. Toxins (Basel). 2021 Jun 30;13(7):464.
[5] Gao W, et al. Sterigmatocystin-induced oxidative DNA damage in human liver-derived cell line through lysosomal damage. Toxicol In Vitro. 2015 Feb;29(1):1-7.
[6] Dubravka R, et al. Sterigmatocystin moderately induces oxidative stress in male Wistar rats after short-term oral treatment. Mycotoxin Res. 2020 May;36(2):181-191.
| Cas No. | 10048-13-2 | SDF | |
| 别名 | 甾体半胱氨酸 | ||
| Canonical SMILES | OC1=CC=CC(O2)=C1C(C3=C2C([C@@](C=CO4)([H])[C@@]4([H])O5)=C5C=C3OC)=O | ||
| 分子式 | C18H12O6 | 分子量 | 324.3 |
| 溶解度 | Acetone: 5 mg/ml | 储存条件 | 4°C, protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
||
| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 3.0836 mL | 15.4178 mL | 30.8356 mL |
| 5 mM | 0.6167 mL | 3.0836 mL | 6.1671 mL |
| 10 mM | 0.3084 mL | 1.5418 mL | 3.0836 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Sterigmatocystin: A mycotoxin to be seriously considered
Food Chem Toxicol 2018 Aug;118:460-470.PMID:29842907DOI:10.1016/j.fct.2018.05.057.
Sterigmatocystin is a carcinogenic compound that affects several species of crops and several species of experimental animals. The Sterigmatocystin biosynthetic pathway is the best known and most studied. The International Agency for Research on Cancer classifies Sterigmatocystin in the Group 2B. Three groups of analytical methods to determine Sterigmatocystin in food can be found: chromatographic, ELISA immunoassays and chemical sensors. In addition, Sterigmatocystin is a precursor of aflatoxin B1 in those cases where cereals and/or food are contaminated with fungi capable of producing aflatoxins. Chemical structures of Sterigmatocystin and aflatoxin B1 are similar. These mycotoxins are pathogens of animals and cereals, producing a major economic impact on biotechnology and agricultural and food industries. This review summarizes different aspects related to Sterigmatocystin such as its biosynthesis, toxicological studies and analytical methods for its determination.
Sterigmatocystin: Occurrence, toxicity and molecular mechanisms of action - A review
Food Chem Toxicol 2020 Dec;146:111802.PMID:33035632DOI:10.1016/j.fct.2020.111802.
The mycotoxin Sterigmatocystin (STE) is produced mainly by Aspergillus fungi. It has been reported to occur in grains and grain-based products, cheese, coffee, spices and beer. The STE is a known biogenic precursor of aflatoxin B1, sharing with it several structural and biological similarities. The STE has been shown to be hepatotoxic and nephrotoxic in animals and it has been classified as possible human carcinogen (group 2B) by IARC. The STE has been reported to cause a marked decrease in cell proliferation in different mammalian cells. Data available on literature suggest that the cellular mechanisms underlying STE-induced toxicity include the induction of oxidative stress, mitochondrial dysfunction, apoptosis, cell cycle arrest, as well as alteration of immune system function and activation of different signalling pathways. Moreover, STE resulted to be genotoxic, being able to form DNA-adducts and induce DNA damage. Despite its strong cytotoxicity, no risk assessments have been still carried out by authorities due to the lack of toxicity data, so research on STE toxicological impact is still going on. This review reports information available regarding STE toxicity and its related mechanisms of action with the aim of updating information regarding last researches on this mycotoxin.
Sterigmatocystin Limits Plasmodium falciparum Proliferation and Transmission
Pharmaceuticals (Basel) 2021 Nov 29;14(12):1238.PMID:34959639DOI:10.3390/ph14121238.
As part of our drug discovery program against malaria, the Penicillium janthinellum extract was discovered to inhibit P. falciparum proliferation in blood and transmission to mosquitoes. Bioactivity-guided fractionation of P. janthinellum extraction was carried out using chromatographic techniques. We determined the activities of fractions against Plasmodium falciparum asexual stage parasite proliferation in culture and sexual stage parasite transmission to mosquitoes using standard membrane feeding assays (SMFA). One active compound was isolated. Based on mass spectrometry and nuclear magnetic resonance profiles, the compound was structurally determined to be Sterigmatocystin. Sterigmatocystin inhibited P. falciparum proliferation in the blood with an IC50 of 34 µM and limited the sexual parasites to infect mosquitoes with an IC50 of 48 µM. Meanwhile, Sterigmatocystin did not show any acute toxicity to human kidney cells at a concentration of 64 µM or lower. Sterigmatocystin can be used as a drug lead for malaria control and as a probe to understand molecular mechanisms of malaria transmission.
Sterigmatocystin: occurrence in foodstuffs and analytical methods--an overview
Mol Nutr Food Res 2010 Jan;54(1):136-47.PMID:19998385DOI:10.1002/mnfr.200900345.
Sterigmatocystin (STC) is a mycotoxin produced by fungi of many different Aspergillus species. Other species such as Bipolaris, Chaetomium, Emiricella are also able to produce STC. STC producing fungi were frequently isolated from different foodstuffs, while STC was regularly detected in grains, corn, bread, cheese, spices, coffee beans, soybeans, pistachio nuts, animal feed and silage. STC shows different toxicological, mutagenic and carcinogenic effects in animals and has been recognized as a 2B carcinogen (possible human carcinogen) by International Agency for Research on Cancer. There are more than 775 publications available in Scopus (and more than 505 in PubMed) mentioning STC, but there is no summary information available about STC occurrence and analysis in food. This review presents an overview of the worldwide information on the occurrence of STC in different foodstuffs during the last 40 years, and describes the progress made in analytical methodology for the determination of STC in food.
Aflatoxin B1 and Sterigmatocystin: method development and occurrence in tea
Food Addit Contam Part B Surveill 2022 Mar;15(1):31-37.PMID:34596493DOI:10.1080/19393210.2021.1984316.
Tea is one of the most popular beverage in the world and may be contaminated by fungi and mycotoxins during processing. To analyse aflatoxin B1 (AFB1) and Sterigmatocystin (STC) in three types of tea, a simple, fast, sensitive and reliable method of these two myxotoxins was developed. Recoveries obtained ranged from 95.9% to 118.0% and the RSDs were between 0.3% and 11.2%. The range of LODs was 0.2-0.45 µg/kg for AFB1 and 0.04-0.12 µg/kg for STC. The range of LOQs was 0.67-1.73 µg/kg for AFB1 and 0.13-0.40 µg/kg for STC. The optimised procedure was applied to analyse 126 tea samples randomly collected from different markets in China. AFB1 was not detected, but STC was determined in 17 samples with concentrations ranging from 0.13 to 4.48 µg/kg. The detection rate of STC was 5%, 8.9% and 33.3% in black tea, green tea and Oolong tea, respectively.