Crotocin
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| Category | Antibiotics |
| Catalog number | BBF-01083 |
| CAS | 21284-11-7 |
| Molecular Weight | 332.39 |
| Molecular Formula | C19H24O5 |
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Description
It is produced by the strain of Cephalosporium crotocinigenum. It has the fungal activity of anti-cryptococcus neoforme, candida albicans, Tinea trichoderma of brewer's yeast, and can be inactivated by blood.
Specification
| Synonyms | Antibiotic T; 4-Isocrotonyloxy-7,8-epoxyscirp-9-ene; Trichothec-9-en-4-beta-ol, 7-beta,8-beta:12,13-diepoxy-, crotonate, (Z)-; Trichothec-9-en-4-ol, 7,8:12,13-diepoxy-, (2Z)-2-butenoate, (4beta,7beta,8beta)- |
| IUPAC Name | [(2R,3R,5S,8R,10R,12R,13S)-1,2,6-trimethylspiro[4,9-dioxatetracyclo[8.2.1.02,8.03,5]tridec-6-ene-13,2'-oxirane]-12-yl] (Z)-but-2-enoate |
| Canonical SMILES | CC=CC(=O)OC1CC2C3(C1(C4(C(O2)C=C(C5C4O5)C)C)C)CO3 |
| InChI | InChI=1S/C19H24O5/c1-5-6-14(20)23-12-8-13-19(9-21-19)18(12,4)17(3)11(22-13)7-10(2)15-16(17)24-15/h5-7,11-13,15-16H,8-9H2,1-4H3/b6-5-/t11-,12-,13-,15+,16+,17-,18?,19+/m1/s1 |
| InChI Key | LAQCZBYXNRANFU-PMKNNYEISA-N |
| Source | Trichothecenes are produced on many different grains like wheat, oats or maize by various Fusarium species such as F. graminearum, F. sporotrichioides, F. poae and F. equiseti. |
Properties
| Appearance | Colorless Prismatic Crystal |
| Antibiotic Activity Spectrum | Fungi; Yeast |
| Melting Point | 126 °C |
| Solubility | Soluble in Chloroform, Methanol, Acetone |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Crotocin is a trichothecene. Unlike many other mycotoxins, trichothecenes do not require metabolic activation to exert their biological activity, instead directly reacting with cellular components. Trichothecenes are cytotoxic to most eukaryotic cells due to their powerful ability to inhibit protein synthesis. They do this by freely moving across the plasma membrane and binding specifically to ribosomes with high-affinity. Specifically, they interfere with the active site of peptidyl transferase at the 3'-end of large 28S ribosomal RNA and inhibit the initiation, elongation or termination step of protein synthesis, as well as cause polyribosomal disaggregation. Protein synthesis is an essential function in all tissues, but tissues where cells are actively and rapidly growing and dividing are very susceptible to the toxins. Additionally, binding to ribosomes is thought to activate proteins in downstream signalling events related to immune response and apoptosis, such as mitogen-activated protein kinases. This is known as ribotoxic stress response. Trichothecenes may also induce some alterations in membrane structure, leading to increased lipid peroxidation and inhibition of electron transport activity in the mitochondria. They can further induce apoptosis through generation of reactive oxygen species. Further secondary effects of trichothecenes include inhibition of RNA and DNA synthesis, and also inhibition of mitosis. |
Reference Reading
1. Necrotic oral lesions in chickens fed diacetoxyscirpenol, T-2 toxin, and crotocin
M S Chi, C J Mirocha Poult Sci. 1978 May;57(3):807-8. doi: 10.3382/ps.0570807.
One-day-old broiler chicks were fed a diet containing either 5 ppm diacetoxyscirpenol (DAS), 5 ppm T-2 toxin, 10 ppm crotocin, or a control diet for 3 weeks. Chicks fed the diet containing DAS and T-2 toxin showed yellowish plaque-type lesions on the beak, tongue, and angle of the mouth. Crotocin did not cause such lesions nor any apparent clinical signs. Chicks fed DAS had the lowest weight gain followed by the T-2, crotocin, and control group in that order; however, chicks fed crotocin had the poorest feed conversion ratio.
2. A sensitive enzyme-linked immunosorbent assay for detection of T-2 toxin with monoclonal antibodies
J Chiba, O Kawamura, H Kajii, K Ohtani, S Nagayama, Y Ueno Food Addit Contam. 1988 Oct-Dec;5(4):629-39. doi: 10.1080/02652038809373727.
Six monoclonal antibodies (mAbs, T-2.1, 2, 3, 4, 5, 6) which react with a trichothecene mycotoxin, T-2 toxin (T-2), were prepared. All antibodies specifically reacted with T-2 but less (0.5% of T-2) with the metabolites such as HT-2 toxin and 3'-hydroxy-T-2 toxin. Significant but less than 0.02% cross-reactivity was observed with T-2 triol, 3'-hydroxy-HT-2 toxin and neosolaniol. No significant reaction with other trichothecenes such as deoxynivalenol, nivalenol, fusarenon-X, crotocin, or roridin A was observed. The least detectable amount of T-2 with the best mAb T-2.1 was 2.5 pg T-2 per assay. This specific and highly sensitive assay for T-2 was applied for the quantitation of T-2 in wheat flour spiked with mycotoxin, with combination of a simple extraction procedure.
3. Trichothecenes in food and feed: Occurrence, impact on human health and their detection and management strategies
Dipendra Kumar Mahato, Shikha Pandhi, Madhu Kamle, Akansha Gupta, Bharti Sharma, Brajesh Kumar Panda, Shubhangi Srivastava, Manoj Kumar, Raman Selvakumar, Arun Kumar Pandey, Priyanka Suthar, Shalini Arora, Arvind Kumar, Shirani Gamlath, Ajay Bharti, Pradeep Kumar Toxicon. 2022 Mar;208:62-77. doi: 10.1016/j.toxicon.2022.01.011. Epub 2022 Jan 31.
Trichothecenes (TCNs) are the mycotoxins produced by many fungal species such as Fusarium, Myrothecium, and Stachybotrys and pose a considerable health risk. Based on their characteristic functional moieties, they are divided into four categories: Type A (T-2, HT-2, diacetoxyscirpenol (DAS), harzianum A, neosolaniol (NEO) and trichodermin), Type B (deoxynivalenol (DON), nivalenol (NIV), trichothecin and fusarenon X), Type C (crotocin) and Type D (satratoxin G & H, roridin A and verrucarin A) with types A and B being the most substantial. TCNs cause growth retardation in eukaryotes, suppress seedling growth or regeneration in plants and could be a reason for animal reproductive failure. Due to the increased frequency of occurrence and widespread distribution of TCNs in food and feed, knowledge of their sources of occurrence is essential to strategise their control and management. Hence, this review provides an overview of various types and sources of TCNs, the associated biosynthetic pathways and genes responsible for production in food and feed. Further, various processing and environmental effects on TCNs production, detection techniques and management strategies are also briefly outlined.
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
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
