Alternariol
Solid powder
Others
Alternariol is a mycotoxin produced by fungi of the Alternaria genus. It is commonly found in contaminated food and feed, and has been associated with various health problems in humans and animals. In recent years, alternariol has gained attention as a potential therapeutic agent due to its bioactivity and potency. This paper aims to provide a comprehensive review of alternariol, including its method of synthesis or extraction, chemical structure and biological activity, biological effects, applications, future perspectives, and challenges.
258.23 g/mol
258.23 g/mol
Formulation:
258.23 g/mol
Source:
Usage:
Alternariol
The product is for non-human research only. Not for therapeutic or veterinary use.
Catalog Number: BT-258562
CAS Number: 641-38-3
Molecular Formula: C14H10O5
Molecular Weight: 258.23 g/mol
CAS Number | 641-38-3 |
---|---|
Product Name | Alternariol |
Molecular Formula | C14H10O5 |
Molecular Weight | 258.23 g/mol |
Appearance | Solid powder |
InChI | InChI=1S/C14H10O5/c1-6-2-7(15)5-11-12(6)9-3-8(16)4-10(17)13(9)14(18)19-11/h2-5,15-17H,1H3 |
InChI Key | CEBXXEKPIIDJHL-UHFFFAOYSA-N |
IUPAC Name | 3,7,9-trihydroxy-1-methylbenzo[c]chromen-6-one |
Canonical SMILES | CC1=CC(=CC2=C1C3=C(C(=CC(=C3)O)O)C(=O)O2)O |
Description | Alternariol is a mycotoxin produced by fungi of the Alternaria genus. It is commonly found in contaminated food and feed, and has been associated with various health problems in humans and animals. In recent years, alternariol has gained attention as a potential therapeutic agent due to its bioactivity and potency. This paper aims to provide a comprehensive review of alternariol, including its method of synthesis or extraction, chemical structure and biological activity, biological effects, applications, future perspectives, and challenges. |
Method of Synthesis or Extraction | Alternariol can be synthesized or extracted from various sources, including fungi, plants, and chemical synthesis. The most commonly used methods for alternariol extraction are solvent extraction and solid-phase extraction. Solvent extraction involves the use of organic solvents such as methanol, ethanol, and acetone to extract alternariol from the sample. Solid-phase extraction involves the use of a solid-phase sorbent to selectively extract alternariol from the sample. Both methods have their advantages and disadvantages in terms of efficiency and yield. Solvent extraction is relatively simple and efficient, but it may result in low yield and environmental and safety concerns. Solid-phase extraction is more selective and yields higher purity, but it is more time-consuming and expensive. |
Chemical Structure and Biological Activity | Alternariol has a chemical structure consisting of a dihydrocoumarin moiety and a tetramic acid moiety. It has been shown to exhibit various biological activities, including antibacterial, antifungal, antiviral, and anticancer activities. The mechanism of action of alternariol is not fully understood, but it is believed to involve the inhibition of DNA synthesis and the induction of oxidative stress. Alternariol has been shown to target various biological pathways, including the MAPK/ERK pathway, the NF-κB pathway, and the PI3K/Akt pathway. |
Biological Effects | Alternariol has been shown to have both therapeutic and toxic effects on cell function and signal transduction. It has been shown to induce apoptosis and cell cycle arrest in cancer cells, and to inhibit the growth of bacteria and fungi. However, alternariol has also been shown to have toxic effects on human and animal cells, including genotoxicity, cytotoxicity, and immunotoxicity. The potential therapeutic and toxic effects of alternariol depend on the dose, duration, and route of exposure. |
Applications | Alternariol has various applications in medical research, environmental research, and industrial research. In medical research, alternariol has been studied for its potential role in drug development, particularly in the treatment of cancer and infectious diseases. Clinical trials have shown promising results in the use of alternariol as an anticancer agent. However, further research is needed to determine its safety and efficacy in humans. In environmental research, alternariol has been studied for its effects on ecosystems and its role in pollution management. It has been shown to have toxic effects on aquatic organisms and to contribute to the contamination of food and feed. In industrial research, alternariol has been used in manufacturing processes to improve product quality and efficiency. However, health and safety considerations must be taken into account when using alternariol in industrial settings. |
Future Perspectives and Challenges | The use and study of alternariol face several challenges, including its toxicity, limited availability, and lack of standardization. Possible solutions and improvements include the development of safer and more efficient methods for alternariol synthesis and extraction, the standardization of analytical methods for alternariol detection and quantification, and the identification of safer and more effective analogs of alternariol. Future trends and prospects in the application of alternariol in scientific research include the development of new therapeutic agents and the exploration of its potential in other fields, such as agriculture and biotechnology. Conclusion Alternariol is a mycotoxin with both therapeutic and toxic effects. Its method of synthesis or extraction, chemical structure and biological activity, biological effects, applications, future perspectives, and challenges have been discussed in this paper. Further research is needed to fully understand the potential of alternariol as a therapeutic agent and to address the challenges associated with its use and study. |
Melting Point | 350°C |
Other CAS Number | 641-38-3 |
Physical Description | Solid |
Pictograms | Acute Toxic |
Shelf Life | >2 years if stored properly |
SMILES | CC1=CC(=CC2=C1C3=C(C(=CC(=C3)O)O)C(=O)O2)O |
Solubility | Soluble in DMSO |
Storage | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
Synonyms | Alternariol |
Reference | 1: Lou J, Yu R, Wang X, Mao Z, Fu L, Liu Y, Zhou L. Alternariol 9-methyl ether from the endophytic fungus Alternaria sp. Samif01 and its bioactivities. Braz J Microbiol. 2016 Jan-Mar;47(1):96-101. doi: 10.1016/j.bjm.2015.11.004. Epub 2016 Jan 27. PubMed PMID: 26887231; PubMed Central PMCID: PMC4822747. 2: Simon H, Hoffmann G, Hübner F, Humpf HU, Karst U. Electrochemical simulation of metabolic reactions of the secondary fungal metabolites alternariol and alternariol methyl ether. Anal Bioanal Chem. 2016 Apr;408(10):2471-83. doi: 10.1007/s00216-016-9344-z. Epub 2016 Feb 11. PubMed PMID: 26869346. 3: Dellafiora L, Dall'Asta C, Cruciani G, Galaverna G, Cozzini P. Molecular modelling approach to evaluate poisoning of topoisomerase I by alternariol derivatives. Food Chem. 2015 Dec 15;189:93-101. doi: 10.1016/j.foodchem.2015.02.083. Epub 2015 Feb 24. PubMed PMID: 26190606. 4: Soukup ST, Kohn BN, Pfeiffer E, Geisen R, Metzler M, Bunzel M, Kulling SE. Sulfoglucosides as Novel Modified Forms of the Mycotoxins Alternariol and Alternariol Monomethyl Ether. J Agric Food Chem. 2016 Nov 23;64(46):8892-8901. Epub 2016 Nov 15. PubMed PMID: 27776211. 5: Fernández-Blanco C, Font G, Ruiz MJ. Role of quercetin on Caco-2 cells against cytotoxic effects of alternariol and alternariol monomethyl ether. Food Chem Toxicol. 2016 Mar;89:60-6. doi: 10.1016/j.fct.2016.01.011. Epub 2016 Jan 21. PubMed PMID: 26802676. 6: Tiessen C, Ellmer D, Mikula H, Pahlke G, Warth B, Gehrke H, Zimmermann K, Heiss E, Fröhlich J, Marko D. Impact of phase I metabolism on uptake, oxidative stress and genotoxicity of the emerging mycotoxin alternariol and its monomethyl ether in esophageal cells. Arch Toxicol. 2017 Mar;91(3):1213-1226. doi: 10.1007/s00204-016-1801-0. Epub 2016 Jul 15. PubMed PMID: 27422292; PubMed Central PMCID: PMC5316404. 7: Estiarte N, Crespo-Sempere A, Marín S, Sanchis V, Ramos AJ. Effect of 1-methylcyclopropene on the development of black mold disease and its potential effect on alternariol and alternariol monomethyl ether biosynthesis on tomatoes infected with Alternaria alternata. Int J Food Microbiol. 2016 Nov 7;236:74-82. doi: 10.1016/j.ijfoodmicro.2016.07.001. Epub 2016 Jul 4. PubMed PMID: 27454782. 8: Graf E, Schmidt-Heydt M, Geisen R. HOG MAP kinase regulation of alternariol biosynthesis in Alternaria alternata is important for substrate colonization. Int J Food Microbiol. 2012 Jul 16;157(3):353-9. doi: 10.1016/j.ijfoodmicro.2012.06.004. Epub 2012 Jun 9. PubMed PMID: 22726725. 9: Liu Y, Rychlik M. Biosynthesis of seven carbon-13 labeled Alternaria toxins including altertoxins, alternariol, and alternariol methyl ether, and their application to a multiple stable isotope dilution assay. Anal Bioanal Chem. 2015 Feb;407(5):1357-69. doi: 10.1007/s00216-014-8307-5. Epub 2015 Jan 11. PubMed PMID: 25577349. 10: Hildebrand AA, Kohn BN, Pfeiffer E, Wefers D, Metzler M, Bunzel M. Conjugation of the mycotoxins alternariol and alternariol monomethyl ether in tobacco suspension cells. J Agric Food Chem. 2015 May 20;63(19):4728-36. doi: 10.1021/acs.jafc.5b00806. Epub 2015 May 7. PubMed PMID: 25912034. 11: Abou-Hany RA, Urraca JL, Descalzo AB, Gómez-Arribas LN, Moreno-Bondi MC, Orellana G. Tailoring molecularly imprinted polymer beads for alternariol recognition and analysis by a screening with mycotoxin surrogates. J Chromatogr A. 2015 Dec 18;1425:231-9. doi: 10.1016/j.chroma.2015.11.055. Epub 2015 Nov 28. PubMed PMID: 26632518. 12: Juan-García A, Juan C, Manyes L, Ruiz MJ. Binary and tertiary combination of alternariol, 3-acetyl-deoxynivalenol and 15-acetyl-deoxynivalenol on HepG2 cells: Toxic effects and evaluation of degradation products. Toxicol In Vitro. 2016 Aug;34:264-73. doi: 10.1016/j.tiv.2016.04.016. Epub 2016 Apr 27. PubMed PMID: 27131905. 13: Fleck SC, Sauter F, Pfeiffer E, Metzler M, Hartwig A, Köberle B. DNA damage and repair kinetics of the Alternaria mycotoxins alternariol, altertoxin II and stemphyltoxin III in cultured cells. Mutat Res Genet Toxicol Environ Mutagen. 2016 Mar;798-799:27-34. doi: 10.1016/j.mrgentox.2016.02.001. Epub 2016 Feb 8. PubMed PMID: 26994491. 14: Fernández-Blanco C, Juan-García A, Juan C, Font G, Ruiz MJ. Alternariol induce toxicity via cell death and mitochondrial damage on Caco-2 cells. Food Chem Toxicol. 2016 Feb;88:32-9. doi: 10.1016/j.fct.2015.11.022. Epub 2015 Dec 9. PubMed PMID: 26683312. 15: Saha D, Fetzner R, Burkhardt B, Podlech J, Metzler M, Dang H, Lawrence C, Fischer R. Identification of a polyketide synthase required for alternariol (AOH) and alternariol-9-methyl ether (AME) formation in Alternaria alternata. PLoS One. 2012;7(7):e40564. doi: 10.1371/journal.pone.0040564. Epub 2012 Jul 6. PubMed PMID: 22792370; PubMed Central PMCID: PMC3391263. 16: Solhaug A, Wisbech C, Christoffersen TE, Hult LO, Lea T, Eriksen GS, Holme JA. The mycotoxin alternariol induces DNA damage and modify macrophage phenotype and inflammatory responses. Toxicol Lett. 2015 Nov 19;239(1):9-21. doi: 10.1016/j.toxlet.2015.08.1107. Epub 2015 Sep 2. PubMed PMID: 26341179. 17: Broggi L, Reynoso C, Resnik S, Martinez F, Drunday V, Bernal AR. Occurrence of alternariol and alternariol monomethyl ether in beverages from the Entre Rios Province market, Argentina. Mycotoxin Res. 2013 Feb;29(1):17-22. doi: 10.1007/s12550-012-0147-6. Epub 2012 Oct 19. PubMed PMID: 23334721. 18: Ackermann Y, Curtui V, Dietrich R, Gross M, Latif H, Märtlbauer E, Usleber E. Widespread occurrence of low levels of alternariol in apple and tomato products, as determined by comparative immunochemical assessment using monoclonal and polyclonal antibodies. J Agric Food Chem. 2011 Jun 22;59(12):6360-8. doi: 10.1021/jf201516f. Epub 2011 May 23. PubMed PMID: 21534631. 19: Schwarz C, Kreutzer M, Marko D. Minor contribution of alternariol, alternariol monomethyl ether and tenuazonic acid to the genotoxic properties of extracts from Alternaria alternata infested rice. Toxicol Lett. 2012 Oct 2;214(1):46-52. doi: 10.1016/j.toxlet.2012.08.002. Epub 2012 Aug 13. PubMed PMID: 22906495. 20: Fernández-Blanco C, Font G, Ruiz MJ. Oxidative DNA damage and disturbance of antioxidant capacity by alternariol in Caco-2 cells. Toxicol Lett. 2015 Jun 1;235(2):61-6. doi: 10.1016/j.toxlet.2015.03.013. Epub 2015 Mar 28. PubMed PMID: 25827405. |
PubChem Compound | Alternariol |
Last Modified | May 30 2023 |