Sterigmatocystin

Sterigmatocystin

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Sterigmatocystin
Category Mycotoxins
Catalog number BBF-04644
CAS 10048-13-2
Molecular Weight 324.28
Molecular Formula C18H12O6
Purity >95% by HPLC

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Description

Sterigmatocystin is a mycotoxin produced by several species of aspergillus. It is structurally related to the aflatoxins. It is mutagenic, teratogenic and carcinogenic and is less widespread and potent than Aflatoxin. It inhibits acyl-CoA. It is a cholesterol acyltransferase (ACAT) with selectivity for the ACAT2 isoenzyme.

Specification

Synonyms (3aR,12cS)-3a,12c-Dihydro-8-hydroxy-6-methoxy-7H-furo[3',2':4,5]furo[2,3-c]xanthen-7-one; (3aR-cis)-3a,12c-Dihydro-8-hydroxy-6-methoxy-7H-furo[3',2':4,5]furo[2,3-c]xanthen-7-one; NSC 201423; NSC 204985; Sterigmatocystine
Storage Store at -20°C
IUPAC Name (3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one
Canonical SMILES COC1=C2C(=C3C4C=COC4OC3=C1)OC5=CC=CC(=C5C2=O)O
InChI InChI=1S/C18H12O6/c1-21-11-7-12-13(8-5-6-22-18(8)24-12)17-15(11)16(20)14-9(19)3-2-4-10(14)23-17/h2-8,18-19H,1H3/t8-,18+/m0/s1
InChI Key UTSVPXMQSFGQTM-DCXZOGHSSA-N
Source Sterigmatocystin have usually been on mouldy, or poor quality materials such as wheat, maize, animal feed, hard cheese, pecan nuts and green coffee beans.

Properties

Appearance Pale Yellow to Light Yellow Solid
Boiling Point 569.7°C at 760 mmHg
Melting Point >230°C (dec.)
Density 1.51 g/cm3
Solubility Soluble in DMF, DMSO; Moderately soluble in Methanol, Ethanol, Chloroform; Poorly soluble in Water

Toxicity

Carcinogenicity 2B, possibly carcinogenic to humans.
Mechanism Of Toxicity Sterigmatocystin's carcinogenic properties are a result of its ability to form guanyl DNA adducts and bind to DNA. In addition, DNA adduct formation causes enhanced production of reactive oxygen species and an imbalance in antioxidant defense, leading to enhanced lipid peroxidation that causes cell damage. (A2888, A2958, A2959)
Toxicity LD50: 166 mg/kg (Rat, 10 days); LD50: >800 mg/kg (Mouse); LD50: 60-65 mg/kg (Intraperitoneal, Rat).

Reference Reading

1. Monitoring of sterigmatocystin biosynthesis using RT-qPCR in airborne Aspergillus species of the series Versicolores
A Géry, B Basset, M Gosselin, V Séguin, J Bonhomme, D Garon J Microbiol Methods. 2022 Nov;202:106580. doi: 10.1016/j.mimet.2022.106580. Epub 2022 Sep 30.
Aspergilli series Versicolores have been shown to be explanatory variables for different symptoms like coughing and dizziness experienced by residents of mold-damaged homes. Among these species, eight are particularly recurrent in bioaerosols: Aspergillus amoenus, A. creber, A. fructus, A. jensenii, A. protuberus, A. puulaauensis, A. sydowii and A. tabacinus. In order to monitor the biosynthesis of sterigmatocystin (a mycotoxin associated with a risk of cancer development) and the development of these molds, we developed an RT-qPCR tool by targeting the aflR and rho1 genes. A total of 30 fungal isolates representing these eight species were included. For each of them, sterigmatocystin was quantified by UPLC-HRMS and (1 → 3)-β-D-glucan by visible spectrophotometry using Endosafe®-PTS™-Glucan Cartridges. After validation of our method by RT-qPCR, the direct assay was compared to the amount of aflR and rho1 cDNA. The sterigmatocystin and aflR assays showed a significant correlation between these two approaches (p < 0.0001), demonstrated for the first time the production of sterigmatocystin by A. tabacinus and suggested the ability of A. sydowii to synthesize sterigmatocystin. Assays conducted on (1 → 3)-β-D-glucan and rho1 did not show a correlation, supporting the multiplicity of functions performed in fungal cells by the RHO1 GTPase. The proposed tool could allow monitoring of sterigmatocystin biosynthesis by Aspergillus of the series Versicolores under different culture and climatic conditions.
2. Sterigmatocystin-induced DNA damage triggers cell-cycle arrest via MAPK in human neuroblastoma cells
Veronica Zingales, Mónica Fernández-Franzón, Maria-José Ruiz Toxicol Mech Methods. 2021 Sep;31(7):479-488. doi: 10.1080/15376516.2021.1916801. Epub 2021 May 26.
Sterigmatocystin (STE) is a common mycotoxin found in food and feed. Many studies showed that STE is genotoxic. However, up to now, the potential genotoxicity of STE on human neuronal system remains unknown. In this study, we explored the effect of STE on DNA damage and cell-cycle progression on human neuroblastoma SH-SY5Y cells exposed to various concentrations of STE (0.78, 1.56 and 3.12 µM) for 24 h. The results indicated that STE exposure induced DNA damage, as evidenced by DNA comet tails formation and increased γH2AX foci. Additionally, genotoxicity was confirmed by micronuclei (MN) analysis. Furthermore, we found that STE exposure led to cell-cycle arrest at the S and the G2/M phase. Considering the important role played by MAPK and p53 signaling pathways in cell-cycle arrest, we explored their potential involvement in STE-induced cell-cycle arrest by using specific inhibitors. The inhibition of JNK and ERK resulted to attenuate S and G2/M arrest, whereas the inhibition of p38 and p53 attenuated only STE-induced S phase arrest. In conclusion, the present study demonstrates that STE induced DNA damage and triggered MAPK and p53 pathways activation, resulting in cell-cycle arrest at the S and the G2/M phase.
3. Aflatoxin B1 and sterigmatocystin: method development and occurrence in tea
Yarong Zhao, Rui Zeng, Qiongshan Wang, Peirong Chen, Xiangxiang Liu, Xu Wang Food Addit Contam Part B Surveill. 2022 Mar;15(1):31-37. doi: 10.1080/19393210.2021.1984316. Epub 2021 Oct 1.
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.

Spectrum

Predicted LC-MS/MS Spectrum - 10V, Positive

Experimental Conditions

Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da

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