Trichodermin
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| Category | Antifungal |
| Catalog number | BBF-03422 |
| CAS | 4682-50-2 |
| Molecular Weight | 292.37 |
| Molecular Formula | C17H24O4 |
| Purity | 99% |
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Description
Trichodermin is a terpenoid antibiotic which has anti-fungal and protozoal effects. It is originally isolated from Trichoderma viride.
Specification
| Synonyms | Trichoderonin; NSC 73846; 12,13-Epoxytrichothec-9-en-4-ol acetate; [(2S)-trimethylspiro[[?]-2,2'-oxirane]yl] acetate |
| Storage | Store at 2-8°C |
| IUPAC Name | [(1S,2R,7R,9R,11R,12S)-1,2,5-trimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-11-yl] acetate |
| Canonical SMILES | CC1=CC2C(CC1)(C3(C(CC(C34CO4)O2)OC(=O)C)C)C |
| InChI | InChI=1S/C17H24O4/c1-10-5-6-15(3)12(7-10)21-14-8-13(20-11(2)18)16(15,4)17(14)9-19-17/h7,12-14H,5-6,8-9H2,1-4H3/t12-,13-,14-,15+,16-,17+/m1/s1 |
| InChI Key | HNEGCRMUYSKRRR-IKIFYQGPSA-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 |
| Boiling Point | 371.2°C at 760 mmHg |
| Melting Point | 45-46°C |
| Density | 1.19 g/cm3 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Trichodermin 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. Synthesis of Trichodermin Derivatives and Their Antimicrobial and Cytotoxic Activities
Santiago Gutiérrez, Bastien Cautain, Javier E Barúa, Rosa E Cardoza, Enrique Monte, Francisca Vicente, Rosa Hermosa, Nuria de Pedro, Mercedes de la Cruz, Isidro G Collado Molecules . 2019 Oct 22;24(20):3811. doi: 10.3390/molecules24203811.
Trichothecene mycotoxins are recognized as highly bioactive compounds that can be used in the design of new useful bioactive molecules. InTrichoderma brevicompactum, the first specific step in trichothecene biosynthesis is carried out by a terpene cyclase, trichodiene synthase, that catalyzes the conversion of farnesyl diphosphate to trichodiene and is encoded by thetri5gene. Overexpression oftri5resulted in increased levels of trichodermin, a trichothecene-type toxin, which is a valuable tool in preparing new molecules with a trichothecene skeleton. In this work, we developed the hemisynthesis of trichodermin and trichodermol derivatives in order to evaluate their antimicrobial and cytotoxic activities and to study the chemo-modulation of their bioactivity. Some derivatives with a short chain at the C-4 position displayed selective antimicrobial activity againstCandida albicansand they showed MIC values similar to those displayed by trichodermin. It is important to highlight the cytotoxic selectivity observed for compounds9,13, and15, which presented average IC50values of 2 μg/mL and were cytotoxic against tumorigenic cell line MCF-7 (breast carcinoma) and not against Fa2N4 (non-tumoral immortalized human hepatocytes).
2. Trichodermin (4β-acet-oxy-12,13-epoxy-trichothec-9-ene)
Chu-Long Zhang, Fu-Cheng Lin, Shao-Yuan Chen, Yu-Zhe Chen Acta Crystallogr Sect E Struct Rep Online . 2008 Mar 12;64(Pt 4):o702. doi: 10.1107/S1600536808006168.
In the title natural product, C(17)H(24)O(4), which is a very potent inhibitor of protein synthesis in mammalian cells, the five-membered ring displays an envelope conformation, whereas the two six-membered rings show different conformations, viz. chair and half-chair.
3. Trichodermin (12,13-ep-oxy-trichethec-9-en-4β-yl 4-fluoro-benzoate)
Zong-Cheng Wang, Yong Zhou, Jing-Li Cheng, Xu-Hui Xu, Jin-Hao Zhao Acta Crystallogr Sect E Struct Rep Online . 2010 Jul 24;66(Pt 8):o2097. doi: 10.1107/S1600536810028461.
IN THE TITLE TRICHODERMIN COMPOUND (SYSTEMATIC NAME: 12,13-ep-oxy-trichothec-9-en-4β-yl 4-fluoro-benzoate), C(22)H(25)FO(4), the five-membered ring displays an envelope conformation, whereas the two six-membered rings show the different conformations, viz. chair and half-chair. As for the seven-membered ring, the dihedral angle between the mean planes formed by the four C atoms of the envelope unit and the three C and one O atoms of the six-membered chair is 68.67 (2)°; these two mean planes are nearly perpendicular to the ep-oxy ring with angles of 87.97 (2)and 88.14 (2)°, respectively.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C17H24O4
Molecular Weight (Monoisotopic Mass): 292.1675 Da
Molecular Weight (Avergae Mass): 292.3701 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C17H24O4
Molecular Weight (Monoisotopic Mass): 292.1675 Da
Molecular Weight (Avergae Mass): 292.3701 Da
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
Molecular Formula: C17H24O4
Molecular Weight (Monoisotopic Mass): 292.1675 Da
Molecular Weight (Avergae Mass): 292.3701 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C17H24O4
Molecular Weight (Monoisotopic Mass): 292.1675 Da
Molecular Weight (Avergae Mass): 292.3701 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 ╳
