Verrucarin J
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| Category | Antibiotics |
| Catalog number | BBF-03442 |
| CAS | 4643-58-7 |
| Molecular Weight | 484.54 |
| Molecular Formula | C27H32O8 |
| Purity | ≥98% |
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Description
Verrucarin J is produced by the strain of Myrothecium verrucaria NRRL 3003. The ED50 of Verrucarin J on giant cell tumor P-815 cells was about 0.001 μg/mL.
Specification
| Synonyms | Muconomycin B; 2',3'-Didehydro-2'-deoxyverrucarin A; Verrucarin A, 2',3'-didehydro-2'-deoxy-, (2'E)-; Verrucrin J; Verrucosporin J |
| Storage | Store at -20°C |
| IUPAC Name | (1R,3R,8R,12E,18E,20E,24R,25S,26S)-5,13,25-trimethylspiro[2,10,16,23-tetraoxatetracyclo[22.2.1.03,8.08,25]heptacosa-4,12,18,20-tetraene-26,2'-oxirane]-11,17,22-trione |
| Canonical SMILES | CC1=CC2C3(CC1)COC(=O)C=C(CCOC(=O)C=CC=CC(=O)OC4C3(C5(CO5)C(C4)O2)C)C |
| InChI | InChI=1S/C27H32O8/c1-17-8-10-26-15-32-24(30)13-18(2)9-11-31-22(28)6-4-5-7-23(29)35-19-14-21(34-20(26)12-17)27(16-33-27)25(19,26)3/h4-7,12-13,19-21H,8-11,14-16H2,1-3H3/b6-4+,7-5+,18-13+/t19-,20-,21-,25-,26-,27+/m1/s1 |
| InChI Key | GXCGYHWSYNQVHU-UGAPSZEOSA-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 Acicular Crystal |
| Application | For research used only |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Boiling Point | 735.353°C at 760 mmHg |
| Melting Point | >320°C |
| Flash Point | 312.2°C |
| Density | 1.297 g/cm3 |
| Solubility | Soluble in Chloroform |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Verrucarin J is a trichothecene produced by Stachybotrys chartarum. 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. Two marine natural products, penicillide and verrucarin J, are identified from a chemical genetic screen for neutral lipid accumulation effectors in Phaeodactylum tricornutum
Mange Yu, Xiaohui Li, Mingcai Jiang, Xi Chen Appl Microbiol Biotechnol . 2020 Mar;104(6):2731-2743. doi: 10.1007/s00253-020-10411-7.
There are a large number of valuable substances in diatoms, such as neutral lipid and pigments. However, due to the lack of clear metabolic pathways, their applications are still limited. Recently, chemical modulators are found to be powerful tools to investigate the metabolic pathways of neutral lipids. Thus, in this study, to identify new neutral lipid accumulation effectors, we screened the natural products that we separated before in the model diatom Phaeodactylum tricornutum (P. tricornutum) by using Nile-red staining method. Two compounds, penicillide and verrucarin J which were isolated from two marine fungal strains, were identified to promote neutral lipid accumulation. However, penicillide and verrucarin J were also found to significantly inhibit the growth of P. tricornutum through specifically inhibiting the photosynthesis of P. tricornutum. Quantitative analysis results showed that penicillide and verrucarin J significantly increased total lipid and triacylglycerol (TAG) contents, which are consistent with previous Nile-red staining results. The expression of key genes such as DGAT2D, GPAT2, LPAT2, and PAP involved in TAG synthesis and unsaturated fatty acids also increased after penicillide and verrucarin J treatments. Besides, many TAG-rich plastoglobuli formed in plastids shown by increased lipid droplets in the cytosol. Finally, penicillide and verrucarin J were found to reduce the expression of synthetic genes of fucoxanthin, and consequently reduced the content of fucoxanthin, indicating that there might be crosstalk between lipid metabolism and fucoxanthin metabolism. Thus, our work exhibits two useful compounds that could be used to further study the metabolic pathways of neutral lipid and fucoxanthin, which will fulfill the promise of diatoms as low cost, high value, sustainable feedstock for high-value products such as neutral lipid and pigments.
2. Macrocyclic Trichothecenes from Myrothecium roridum Strain M10 with Motility Inhibitory and Zoosporicidal Activities against Phytophthora nicotianae
Musrat Zahan Surovy, M Tofazzal Islam, Hartmut Laatsch, Anja Schüffler, Muhammad Abdul Mojid Mondol J Agric Food Chem . 2015 Oct 14;63(40):8777-86. doi: 10.1021/acs.jafc.5b02366.
The cytotoxicity of the extract obtained from Myrothecium roridum M10 and a characteristic (1)H signal at δH ~8 led to the assumption that verrucarin/roridin-type compounds were present. Upscaling on rice medium led to the isolation of four new metabolites: verrucarins Y (1) and Z (6) (macrocyclic trichothecenes), bilain D (12) (a diketopiperazine derivative), and hamavellone C (14) (an unusual cyclopropyl diketone). In addition, nine known trichothecenes [verrucarin A (3), 16-hydroxyverrucarin A (5), verrucarin B (7), 16-hydroxyverrucarin B (8), verrucarin J (2), verrucarin X (4), roridin A (9), roridin L-2 (10), and trichoverritone (11)] and a bicyclic lactone [myrotheciumone A (15)] were identified. Their structures and configurations were determined by spectroscopic methods, published data, Mosher's method, and considering biosyntheses. Some trichothecenes showed motility inhibition followed by lysis of the zoospores against devastating Phytophthora nicotianae within 5 min. Compounds 2, 3, 7, and 9 also exhibited potent activities against Candida albicans and Mucor miehei.
3. Occurrence of type A, B and D trichothecenes, zearalenone and stachybotrylactam in straw
Sarah Asmussen, Barbara Biermaier, Sebastian Ulrich, Sven Dänicke, Christoph Gottschalk, Eunike Bahlinger, Hana Valenta, Magdalena Twarużek, Margit Schollenberger, Frank Ebel Arch Anim Nutr . 2021 Apr;75(2):105-120. doi: 10.1080/1745039X.2021.1877075.
Straw is the main by-product of grain production, used as bedding material and animal feed. If produced or stored under adverse hygienic conditions, straw is prone to the growth of filamentous fungi. Some of them, e.g.Aspergillus, FusariumandStachybotrysspp. are well-known mycotoxin producers. Since studies on mycotoxins in straw are scarce, 192 straw samples (wheatn= 80; barleyn= 79; triticalen= 12; oatn= 11; ryen= 12) were collected across Germany within the German official feed surveillance and screened for the presence of 21 mycotoxins. The following mycotoxins (positive samples for at least one mycotoxinn= 184) were detected: zearalenone (n= 86, 6.0-785 μg/kg), nivalenol (n= 51, 30-2,600 μg/kg), deoxynivalenol (n= 156, 20-24,000 μg/kg), 15-acetyl-deoxynivalenol (n= 34, 20-2,400 μg/kg), 3-acetyl-deoxynivalenol (n= 16, 40-340 μg/kg), scirpentriol (n= 14, 40-680 μg/kg), T-2 toxin (n= 67, 10-250 μg/kg), HT-2 toxin (n= 92, 20-800 μg/kg), T-2 tetraol (n= 13, 70-480 μg/kg). 15-monoacetoxyscirpenol (30 μg/kg) and T-2 triol (60 μg/kg) were only detected in one barley sample. Macrocyclic trichothecenes (satratoxin G, F, roridin E, and verrucarin J) were also found in only one barley sample (quantified as roridin A equivalent: total 183 μg/kg). The occurrence of stachybotrylactam was monitored for the first time in four samples (n= 4, 0.96-7.4 μg/kg). Fusarenon-X, 4,15-diacetoxyscirpenol, neosolaniol, satratoxin H and roridin-L2 were not detectable in the samples. The results indicate a non-negligible contribution of straw to oral and possibly inhalation exposure to mycotoxins of animals or humans handling contaminated straw.
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 ╳
