Sterigmatocystin
(Synonyms: 甾体半胱氨酸) 目录号 : GC44953甾体半胱氨酸是由曲霉属真菌产生的一种霉菌毒素。
Cas No.:10048-13-2
Sample solution is provided at 25 µL, 10mM.
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].
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.
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. |
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 |
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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 |
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2.
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