5975-78-0 Usage
Description
Zearalanone (ZEA), also known as F-2 toxin, is a nonsteroidal estrogenic mycotoxin produced by various Fusarium species, with Fusarium graminearum being the primary producer. It is a secondary metabolite of Zearalenone (ZON) and is found in moldy hay, high-moisture corn, and corn infected before harvest. Zearalanone is a white to off-white solid and is known for its estrogenic effects in domestic livestock. It is also a metabolite of α-zearalanol, a commercially available growth promotant in animals, making it a useful standard for detecting zearanol-contaminated products and Fusarium-contaminated grains.
Uses
Used in Agricultural Industry:
Zearalanone is used as a detection standard for identifying zearanol-contaminated products and Fusarium-contaminated grains. Its presence in these products can indicate potential health risks for both animals and humans due to its estrogenic effects.
Used in Pharmaceutical Industry:
Zearalanone is used as a secondary metabolite in the synthesis of d,l-Zearalanol, which is a commercially available growth promotant in animals. This application aids in the development and production of growth-enhancing substances for the livestock industry.
Used in Research and Development:
As a secondary metabolite of Zearalenone, Zearalanone is utilized in research and development for understanding the effects of mycotoxins on domestic livestock and their potential impact on human health. This knowledge can contribute to the development of strategies for mitigating the risks associated with mycotoxin contamination in the food and feed supply chain.
Biological Activity
zearalanone (zan) is an estrogen receptor agonist and also an androgen receptor antagonist [1].zearalenone (zen), a β-resorcyclic acid lactone (ral), is a non-steroidal estrogenic mycotoxin biosynthesized by several fusarium species. zearalenone (zen) is the well-known mycotoxin present in numerous agricultural products [1][2][3][4]. in the human endometrial ishikawa cell line, zearalenone (zen) exhibited strong oestrogenicity [4].when incubated fusarium semitectum on sorghum, the ratio of zan to zen remained constant after 5 days, suggesting that zan might not be suitable for use as an internal standard [5].zearalanone, a major phase i metabolite of zearalenone (zen), is an estrogen receptor agonist and also an androgen receptor antagonist. in mcf-7 cells, zearalanone strongly induced cell proliferation with ec50 value of 1.21 nm and showed significant estrogenic activity. zearalanone behaved as full herα agonist. in palm cells, zearalanone acted as a har antagonist that strongly inhibited the luciferase activity induced by 0.3 nm of r1881, the synthetic androgen [1].
Biochem/physiol Actions
Zearalanone is believed to cause vulvovaginitis and estrogenic responses in swine.
references
[1]. molina-molina jm, real m, jimenez-diaz i, et al. assessment of estrogenic and anti-androgenic activities of the mycotoxin zearalenone and its metabolites using in vitro receptor-specific bioassays. food chem toxicol.2014 dec;74:233-9.[2]. baldwin rs, williams rd, terry mk. zeranol: a review of the metabolism, toxicology, and analytical methods for detection of tissue residues. regul toxicol pharmacol. 1983 mar;3(1):9-25.[3]. migdalof bh, dugger ha, heider jg, et al. biotransformation of zeranol: disposition and metabolism in the female rat, rabbit, dog, monkey and man. xenobiotica. 1983 apr;13(4):209-21.[4]. le guevel r, pakdel f. assessment of oestrogenic potency of chemicals used as growth promoter by in-vitro methods. hum reprod. 2001 may;16(5):1030-6.[5]. aoyama k, ishikuro e, noriduki h, et al. formation ratios of zearalanone, zearalenols, and zearalanols versus zearalenone during incubation of fusarium semitectum on sorghum and ratios in naturally contaminated sorghum. shokuhin eiseigaku zasshi. 2015;56(6):247-51.
Check Digit Verification of cas no
The CAS Registry Mumber 5975-78-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,9,7 and 5 respectively; the second part has 2 digits, 7 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 5975-78:
(6*5)+(5*9)+(4*7)+(3*5)+(2*7)+(1*8)=140
140 % 10 = 0
So 5975-78-0 is a valid CAS Registry Number.
InChI:InChI=1/C18H24O5/c1-12-6-5-9-14(19)8-4-2-3-7-13-10-15(20)11-16(21)17(13)18(22)23-12/h10-12,20-21H,2-9H2,1H3
5975-78-0Relevant articles and documents
Synthesis and cytotoxic activities of semisynthetic zearalenone analogues
Tadpetch, Kwanruthai,Kaewmee, Benyapa,Chantakaew, Kittisak,Kantee, Kawalee,Rukachaisirikul, Vatcharin,Phongpaichit, Souwalak
supporting information, p. 3612 - 3616 (2016/07/21)
Zearalenone is a β-resorcylic acid macrolide with various biological activities. Herein we report the synthesis and cytotoxic activities of 34 zearalenone analogues against human oral epidermoid carcinoma (KB) and human breast adenocarcinoma (MCF-7) cells as well as noncancerous Vero cells. Some zearalenone analogues showed moderately enhanced cytotoxic activities against the two cancer cell lines. We have discovered the potential lead compounds with diminished or no cytotoxicity to Vero cells. Preliminary structure–activity relationship studies revealed that the double bond at the 1′ and 2′ positions of zearalenone core was crucial for cytotoxic activities on both cell lines. In addition, for zearalenol analogues, the unprotected hydroxyl group at C-2 and an alkoxy substituent at C-4 played key roles on cytotoxic effects of both cell lines.
Microbial Transformation of Zearalenone. 2. Reduction, Hydroxylation, and Methylation Products
El-Sharkawy, Saleh H.,Abul-Hajj, Yusuf J.
, p. 515 - 519 (2007/10/02)
Microbial transformations have been employed as a means of preparing analogues of the resorcylic acid lactone zearalenone.Microbial transformation products were initially identified by thin-layer chromatography of fermentation extracts and then prepared by large-scale incubations.Each metabolite was subjected to structural elucidation employing carbon-13 and proton NMR, mass spectrometry, and infrared analysis.Metabolites were identified as α- and β-zearalenol, α- and β-zearalanol, zearalanone, 8'(S)-hydroxyzearalenone, 2,4-dimethoxyzearalenone, and 2-methoxyzearalenone.Binding affinities to rat uterine estrogen receptors were carried out.Only those metabolites having a free 4-phenolic group were capable of binding to the estrogen receptor.However, 8'-hydroxyzearalenone, even with a 4-phenolic hydroxyl, did not bind to the receptor.It is possible that hydrogen bonding of the aliphatic hydroxyl groups to the C-6' carbonyl of zearalenone or equilibrium between the hydroxy ketone and its tautomeric hemiketal may lead to distortion of the conformation of the molecule resulting in loss of binding to the receptor.
