Roridin A
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| Category | Antibiotics |
| Catalog number | BBF-02635 |
| CAS | 14729-29-4 |
| Molecular Weight | 532.62 |
| Molecular Formula | C29H40O9 |
| Purity | ≥98% |
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Description
It has antifungal effect, and it can inhibit 50% of mast cell tumor P815 cells at 0.001 μg/mL in vitro.
Specification
| Synonyms | Roridine A; Roridan A; NSC 200737; Antibiotic 379X; Verrucarin A, 7'-deoxo-7'-(1-hydroxyethyl)- |
| Storage | Store at -20°C |
| IUPAC Name | (1R,3R,8R,12S,13R,17R,18E,20Z,24R,25S,26S)-12-hydroxy-17-[(1R)-1-hydroxyethyl]-5,13,25-trimethylspiro[2,10,16,23-tetraoxatetracyclo[22.2.1.03,8.08,25]heptacosa-4,18,20-triene-26,2'-oxirane]-11,22-dione |
| Canonical SMILES | CC1CCOC(C=CC=CC(=O)OC2CC3C4(C2(C5(CCC(=CC5O3)C)COC(=O)C1O)C)CO4)C(C)O |
| InChI | InChI=1S/C29H40O9/c1-17-9-11-28-15-35-26(33)25(32)18(2)10-12-34-20(19(3)30)7-5-6-8-24(31)38-21-14-23(37-22(28)13-17)29(16-36-29)27(21,28)4/h5-8,13,18-23,25,30,32H,9-12,14-16H2,1-4H3/b7-5+,8-6-/t18-,19-,20-,21-,22-,23-,25+,27-,28-,29+/m1/s1 |
| InChI Key | NSFWWJIQIKBZMJ-PAGWOCKZSA-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 Crystalline |
| Antibiotic Activity Spectrum | fungi; neoplastics (Tumor) |
| Boiling Point | 752.4±60.0°C at 760 mmHg |
| Melting Point | 198-204°C |
| Density | 1.29±0.1 g/cm3 |
| Solubility | Soluble in Chloroform (≥10 mg/mL) |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Roridin A 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. |
| Toxicity | LD50: 1.0 mg/kg (Intravenous, Mouse). |
Reference Reading
1. Production and characterization of monoclonal antibodies to the macrocyclic trichothecene roridin A
R Hack, G Terplan, E Märtlbauer Appl Environ Microbiol . 1988 Sep;54(9):2328-30. doi: 10.1128/aem.54.9.2328-2330.1988.
Two murine monoclonal antibodies to the macrocyclic trichothecene roridin A are described. Screening for antibody production was performed on absorbed anti-mouse immunoglobulin serum as double-antibody solid phase, and further characterization was done on affinity-purified anti-mouse IgG serum. The antibodies, designated 5G11 and 4H10, had affinity constants for roridin A of 9.25 X 10(7) and 1.7 X 10(7) liters/mol, respectively. In monoclonal antibody-based direct enzyme immunoassays, these IgG1 antibodies had detection limits for roridin A of 0.4 ng/ml (0.02 ng per assay) and 1.8 ng/ml (0.09 ng per assay), respectively. Both antibodies were most specific for the tested macrocyclic trichothecenes. The relative cross-reactivities of antibody 5G11 with roridin A, roridin J, verrucarin A, satratoxin G, and satratoxin H were 100.0, 43.8, 16.7, 3.7, and 18.9%, respectively; for antibody 4H10 they were 100.0, 6.3, 64.0, 4.4, and 4.9%, respectively.
2. [Preparation of antibodies to roridin A and their applications]
G P Kononenko, E V Zotova, N A Soboleva, V G Zorian, A A Birkin Prikl Biokhim Mikrobiol . 2000 Jul-Aug;36(4):428-32.
Polyclonal rabbit antibodies against a conjugate synthesized through condensing BSA and disubstituted roridin A hemisuccinate allowed roridin A to be determined in solutions at a sensitivity of 0.2 ng/ml. The cross-reactivity of structural analogues--roridin A, verrucarin, and verrucarol--amounted to 100, 2.5, and 0.03%, respectively. The data showed that these antibodies determine roridin A in an indirect heterogeneous enzyme immunoassay in cereal straw samples at a sensitivity of 20 micrograms/kg.
3. The cytotoxicity of macrocyclic trichothecenes, roridin A and verrucarin A, on murine T-cells is reduced by Ia-negative splenic adherent cells
S Kumagai, Y Sugita-Konishi, T Mizuochi Toxicon . 1994 Sep;32(9):1051-7. doi: 10.1016/0041-0101(94)90389-1.
The in vitro effect of macrocyclic trichothecenes, roridin A and verrucarin A, and a non-macrocyclic trichothecene, T-2 toxin, on the concanavalin A-induced murine T-cell blastogenesis was investigated. The macrocyclic trichothecenes inhibited the blastogenesis of both thymocytes and splenocytes, splenocytes being more resistant than thymocytes. Such resistance to macrocyclic trichothecenes was not observed in splenic T-cells separated from the other cell population, nor in splenocytes depleted of adherent cells. In order to find the cell population responsible for resistance, the toxins were incubated with fractionated splenic cells and then cytotoxicity of the supernatants of the incubation mixtures was examined by using T-cell blastogenesis assay. The results showed that the splenocytes depleted of Ia-negative cells had the ability to reduce the cytotoxicity of the macrocyclic trichothecenes, but not that of T-2.
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 ╳
