Sterigmatocystin (BioDeep_00000002621)

 

Secondary id: BioDeep_00000383539

human metabolite Endogenous Toxin natural product Volatile Flavor Compounds


代谢物信息卡片


15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-13-one

化学式: C18H12O6 (324.06338519999997)
中文名称: 柄曲霉素
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 1.02%

分子结构信息

SMILES: C12OC3=C(C(O)=CC=C3)C(=O)C=1C(=CC1O[C@@]3([H])OC=C[C@@]3([H])C2=1)OC
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

描述信息

Sterigmatocystin is a mycotoxin of Aspergillus versicolor and Chaetomium species Sterigmatocystin is a poison of the type dermatoxin, from the fungi genus Aspergillus. It appears on crusts of cheese with mold. Sterigmatocystin is a toxic metabolite structurally closely related to the aflatoxins (compare general fact sheet number 2), and consists of a xanthone nucleus attached to a bifuran structure. Sterigmatocystin is mainly produced by the fungi Aspergillus nidulans and A. versicolor. It has been reported in mouldy grain, green coffee beans and cheese although information on its occurrence in foods is limited. It appears to occur much less frequently than the aflatoxins, although analytical methods for its determination have not been as sensitive until recently, and so it is possible that small concentrations in food commodities may not always have been detected. Although it is a potent liver carcinogen similar to aflatoxin B1, current knowledge suggests that it is nowhere near as widespread in its occurrence. If this is the true situation it would be justified to consider sterigmatocystin as no more than a risk to consumers in special or unusual circumstances. Sterigmatocystin is a number of closely related compounds such o-methyl sterigmatocystin are known and some may also occur naturally. The IARC-classification of sterigmatocystin is group 2B, which means it is possibly carcinogenic to humans. In practice, the risk is quite low however, because this substance only appears on cheese crusts with mold, and because of that the chance of daily exposure is very low. Sterigmatocystin is a molded crust is best not to be consumed in whole, but after removing the crust, the cheese can still be consumed. Sterigmatocystin is a different kind of mold than that which appears on cheese itself, which can simply be removed before further consumption
D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2320

同义名列表

5 个代谢物同义名

15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-13-one; 3a,12C-Dihydro-8-hydroxy-6-methoxy-7H-furo[3,2:4,5]furo[2,3-c]xanthen-7-one, 9ci; Sterigmatocystine; Sterigmatocystin; Sterigmatocystin



数据库引用编号

42 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(0)

代谢反应

3 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(3)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

101 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Monika Trienens, Joachim Kurtz, Bregje Wertheim. Rapid but narrow - Evolutionary adaptation and transcriptional response of Drosophila melanogaster to toxic mould. Molecular ecology. 2023 06; 32(11):2784-2797. doi: 10.1111/mec.16885. [PMID: 37066754]
  • Jihui Xi, Dongyun Yang, Huali Xue, Zhiguang Liu, Yang Bi, Yuan Zhang, Xi Yang, Suqin Shang. Isolation of the Main Pathogens Causing Postharvest Disease in Fresh Angelica sinensis during Different Storage Stages and Impacts of Ozone Treatment on Disease Development and Mycotoxin Production. Toxins. 2023 Feb; 15(2):. doi: 10.3390/toxins15020154. [PMID: 36828468]
  • Siqi Ma, Donglin Zhao, Xiaobin Han, Yulong Peng, Tingting Ren, Mei Wang, Jun Wan, Jilin Ding, Xiuchun Du, Fubin Zhao, Yiqiang Li, Chengsheng Zhang. New application of Aspergillus versicolor in promoting plant growth after suppressing sterigmatocystin production via genome mining and engineering. Microbial biotechnology. 2023 01; 16(1):139-147. doi: 10.1111/1751-7915.14176. [PMID: 36415948]
  • Christina Rehagel, Ronald Maul, Kim Lara Gützkow, Ömer Akineden. Enzyme immunoassays for the detection of mycotoxins in plant-based milk alternatives: pitfalls and limitations. Mycotoxin research. 2022 Nov; 38(4):265-274. doi: 10.1007/s12550-022-00467-x. [PMID: 36053453]
  • Huanyan Liang, Qianyu Hou, Yakui Zhou, Lei Zhang, Meihua Yang, Xiangsheng Zhao. Centrifugation-Assisted Solid-Phase Extraction Coupled with UPLC-MS/MS for the Determination of Mycotoxins in ARECAE Semen and Its Processed Products. Toxins. 2022 10; 14(11):. doi: 10.3390/toxins14110742. [PMID: 36355992]
  • Qin Li, Aimin Fu, Mengsha Wei, Yang Xiao, Jie Yin, Jianzheng Huang, Xiao-Nian Li, Qingyi Tong, Chunmei Chen, Hucheng Zhu, Yonghui Zhang. Asperemestrins A-D, Emestrin Hybrid Polymers with Bridged Skeletons from the Endophytic Fungus Aspergillus nidulans. Organic letters. 2022 09; 24(37):6800-6804. doi: 10.1021/acs.orglett.2c02701. [PMID: 36074729]
  • Maria Alonso-Jauregui, Elena González-Peñas, Adela López de Cerain, Ariane Vettorazzi. Genotoxicity of 12 Mycotoxins by the SOS/umu Test: Comparison of Liver and Kidney S9 Fraction. Toxins. 2022 06; 14(6):. doi: 10.3390/toxins14060400. [PMID: 35737061]
  • Beatriz Arce-López, Lydia Alvarez-Erviti, Barbara De Santis, María Izco, Silvia López-Calvo, Maria Eugenia Marzo-Sola, Francesca Debegnach, Elena Lizarraga, Adela López de Cerain, Elena González-Peñas, Ariane Vettorazzi. Biomonitoring of Mycotoxins in Plasma of Patients with Alzheimer's and Parkinson's Disease. Toxins. 2021 07; 13(7):. doi: 10.3390/toxins13070477. [PMID: 34357949]
  • Beatriz Arce-López, Elena Lizarraga, Reyes López de Mesa, Elena González-Peñas. Assessment of Exposure to Mycotoxins in Spanish Children through the Analysis of Their Levels in Plasma Samples. Toxins. 2021 02; 13(2):. doi: 10.3390/toxins13020150. [PMID: 33672088]
  • Benjamin Kövesi, Szabina Kulcsár, Zsolt Ancsin, Erika Zándoki, Márta Erdélyi, Miklós Mézes, Krisztián Balogh. Individual and Combined Effects of Aflatoxin B1 and Sterigmatocystin on Lipid Peroxidation and Glutathione Redox System of Common Carp Liver. Toxins. 2021 02; 13(2):. doi: 10.3390/toxins13020109. [PMID: 33540648]
  • Hongmei Zeng, Jingjing Cai, Hidemi Hatabayashi, Hiroyuki Nakagawa, Hiromitsu Nakajima, Kimiko Yabe. verA Gene is Involved in the Step to Make the Xanthone Structure of Demethylsterigmatocystin in Aflatoxin Biosynthesis. International journal of molecular sciences. 2020 Sep; 21(17):. doi: 10.3390/ijms21176389. [PMID: 32887494]
  • Shuo Gao, Wen-Jing Tian, Zu-Jian Liao, Guang-Hui Wang, De-Quan Zeng, Xiang-Zhong Liu, Xiao-Yao Wang, Hu Zhou, Hai-Feng Chen, Ting Lin. Chemical Constituents from Endophytic Fungus Annulohypoxylon cf. stygium in Leaves of Anoectochilus roxburghii. Chemistry & biodiversity. 2020 Sep; 17(9):e2000424. doi: 10.1002/cbdv.202000424. [PMID: 32672903]
  • Rašić Dubravka, Jakšić Daniela, Hulina Tomašković Andrea, Kifer Domagoj, Kopjar Nevenka, Rumora Lada, Želježić Davor, Peraica Maja, Šegvić Klarić Maja. Sterigmatocystin moderately induces oxidative stress in male Wistar rats after short-term oral treatment. Mycotoxin research. 2020 May; 36(2):181-191. doi: 10.1007/s12550-019-00382-8. [PMID: 31836962]
  • Veronica Zingales, Mónica Fernández-Franzón, Maria-José Ruiz. Sterigmatocystin-induced cytotoxicity via oxidative stress induction in human neuroblastoma cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2020 Feb; 136(?):110956. doi: 10.1016/j.fct.2019.110956. [PMID: 31712107]
  • Taoling Min, Lei Xiong, Yan Liang, Rui Xu, Chenchang Fa, Sheng Yang, Haifeng Hu. Disruption of stcA blocks sterigmatocystin biosynthesis and improves echinocandin B production in Aspergillus delacroxii. World journal of microbiology & biotechnology. 2019 Jul; 35(7):109. doi: 10.1007/s11274-019-2687-9. [PMID: 31280382]
  • Benjamin Kövesi, Csilla Pelyhe, Erika Zándoki, Miklós Mézes, Krisztián Balogh. Effect of short-term sterigmatocystin exposure on lipid peroxidation and glutathione redox system and expression of glutathione redox system regulatory genes in common carp liver. Toxicon : official journal of the International Society on Toxinology. 2019 Apr; 161(?):50-56. doi: 10.1016/j.toxicon.2019.03.001. [PMID: 30849453]
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  • Victor Sobolev, Renee Arias, Kerestin Goodman, Travis Walk, Valerie Orner, Paola Faustinelli, Alicia Massa. Suppression of Aflatoxin Production in Aspergillus Species by Selected Peanut (Arachis hypogaea) Stilbenoids. Journal of agricultural and food chemistry. 2018 Jan; 66(1):118-126. doi: 10.1021/acs.jafc.7b04542. [PMID: 29207242]
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  • Alberto Biancardi, Chiara Dall'Asta. Determination of sterigmatocystin in feed by LC-MS/MS. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2015; 32(12):2093-100. doi: 10.1080/19440049.2015.1094709. [PMID: 26471726]
  • Yasuo Fushimi, Mitsuhiro Takagi, Seiichi Uno, Emiko Kokushi, Masayuki Nakamura, Hiroshi Hasunuma, Urara Shinya, Eisaburo Deguchi, Johanna Fink-Gremmels. Measurement of sterigmatocystin concentrations in urine for monitoring the contamination of cattle feed. Toxins. 2014 Nov; 6(11):3117-28. doi: 10.3390/toxins6113117. [PMID: 25375815]
  • Runsheng Zheng, Hui Xu, Wenli Wang, Ruoting Zhan, Weiwen Chen. Simultaneous determination of aflatoxin B(1), B(2), G(1), G(2), ochratoxin A, and sterigmatocystin in traditional Chinese medicines by LC-MS-MS. Analytical and bioanalytical chemistry. 2014 May; 406(13):3031-9. doi: 10.1007/s00216-014-7750-7. [PMID: 24658469]
  • Xingang Wang, Anne L Robertson, Jingyu Li, Ruth Jinfen Chai, Wang Haishan, Pranvera Sadiku, Nikolay V Ogryzko, Martin Everett, Kanagasundaram Yoganathan, Hongbo Robert Luo, Stephen A Renshaw, Philip W Ingham. Inhibitors of neutrophil recruitment identified using transgenic zebrafish to screen a natural product library. Disease models & mechanisms. 2014 Jan; 7(1):163-9. doi: 10.1242/dmm.012047. [PMID: 24291762]
  • Min Li, Peiwu Li, Hui Wu, Qi Zhang, Fei Ma, Zhaowei Zhang, Xiaoxia Ding, Hengling Wang. An ultra-sensitive monoclonal antibody-based competitive enzyme immunoassay for sterigmatocystin in cereal and oil products. PloS one. 2014; 9(9):e106415. doi: 10.1371/journal.pone.0106415. [PMID: 25184275]
  • Ya-Ming Xu, Patricia Espinosa-Artiles, Mangping X Liu, A Elizabeth Arnold, A A Leslie Gunatilaka. Secoemestrin D, a cytotoxic epitetrathiodioxopiperizine, and emericellenes A-E, five sesterterpenoids from Emericella sp. AST0036, a fungal endophyte of Astragalus lentiginosus1. Journal of natural products. 2013 Dec; 76(12):2330-6. doi: 10.1021/np400762k. [PMID: 24251417]
  • Ying Zhang, Zhi Gang Yao, Juan Wang, Ling Xiao Xing, Yan Xia, Xiang Hong Zhang. Effects of sterigmatocystin on TNF-α, IL-6 and IL-12 expression in murine peripheral blood mononuclear cells and peritoneal macrophages in vivo. Molecular medicine reports. 2012 May; 5(5):1318-22. doi: 10.3892/mmr.2012.788. [PMID: 22344519]
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