Fumitremorgin B
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| Category | Mycotoxins |
| Catalog number | BBF-04473 |
| CAS | 12626-17-4 |
| Molecular Weight | 479.57 |
| Molecular Formula | C27H33N3O5 |
| Purity | 98.5% |
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Description
Fumitremorgin B is a natural compound isolated from the fermentation broth of Aspergillus fumigatus LN-4. Fumitremorgin B is a tremorgenic mycotoxin that is active against the phytopathogenic fungi. It has antifeedant activity against armyworm (M. separata) larvae when applied to fresh wheat leaves.
Specification
| Synonyms | Lanosulin; 5H,14H-Pyrrolo(1'',2'':4',5')pyrazino(1',2':1,6)pyrido(3,4-b)indole-5,14-dione, 1,2,3,5a,6,11,12,14a-octahydro-5a,6-dihydroxy-9-methoxy-11-(3-methyl-2-butenyl)-12-(2-methyl-1-propenyl)-, (5aR-(5a-alpha,6-alpha,12-beta,14a-alpha))- |
| Storage | Store at -20°C |
| IUPAC Name | (1R,2S,12S,15S)-1,2-dihydroxy-7-methoxy-10-(3-methylbut-2-enyl)-12-(2-methylprop-1-enyl)-10,13,19-triazapentacyclo[11.7.0.03,11.04,9.015,19]icosa-3(11),4(9),5,7-tetraene-14,20-dione |
| Canonical SMILES | CC(=CCN1C2=C(C=CC(=C2)OC)C3=C1C(N4C(=O)C5CCCN5C(=O)C4(C3O)O)C=C(C)C)C |
| InChI | InChI=1S/C27H33N3O5/c1-15(2)10-12-28-20-14-17(35-5)8-9-18(20)22-23(28)21(13-16(3)4)30-25(32)19-7-6-11-29(19)26(33)27(30,34)24(22)31/h8-10,13-14,19,21,24,31,34H,6-7,11-12H2,1-5H3/t19-,21-,24-,27+/m0/s1 |
| InChI Key | WEIYXEFMCIRZHC-MWGWWEMPSA-N |
| Source | Fumitremorgin B is a mycotoxin that has been found in the fungus Aspergillus fumigatus. |
Properties
| Appearance | Powder |
| Antibiotic Activity Spectrum | Fungi |
| Boiling Point | 724.3±60.0°C (Predicted) |
| Melting Point | 205-207°C |
| Density | 1.35±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in DMSO, Methanol, Chloroform |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Fumitremorgin B is a tremorgenic mycotoxin. Tremorgenic mycotoxins exert their toxic effects by interfering with neurotransmitter release, possibly by causing degeneration of nerve terminals. They are thought to inhibit gamma-aminobutyric acid (GABA) receptors, both pre- and postsynaptic, as well as inhibit transmitter breakdown at the GABA-T receptors. This would initially increase neurotransmitter levels, potentiating the GABA-induced chloride current, then lead to decreased levels of neurotransmitter in the synapse. |
Reference Reading
1. Structural basis for endoperoxide-forming oxygenases
Takahiro Mori, Ikuro Abe Beilstein J Org Chem. 2022 Jun 21;18:707-721. doi: 10.3762/bjoc.18.71. eCollection 2022.
Endoperoxide natural products are widely distributed in nature and exhibit various biological activities. Due to their chemical features, endoperoxide and endoperoxide-derived secondary metabolites have attracted keen attention in the field of natural products and organic synthesis. In this review, we summarize the structural analyses, mechanistic investigations, and proposed reaction mechanisms of endoperoxide-forming oxygenases, including cyclooxygenase, fumitremorgin B endoperoxidase (FtmOx1), and the asnovolin A endoperoxygenase NvfI.
2. Structural Insight into the Catalytic Mechanism of the Endoperoxide Synthase FtmOx1
Lian Wu, Zhanfeng Wang, Yixin Cen, Binju Wang, Jiahai Zhou Angew Chem Int Ed Engl. 2022 Mar 14;61(12):e202112063. doi: 10.1002/anie.202112063. Epub 2022 Feb 3.
The 2-oxoglutarate (2OG)-dependent non-heme enzyme FtmOx1 catalyzes the endoperoxide biosynthesis of verruculogen. Although several mechanistic studies have been carried out, the catalytic mechanism of FtmOx1 is not well determined owing to the lack of a reliable complex structure of FtmOx1 with fumitremorgin B. Herein we provide the X-ray crystal structure of the ternary complex FtmOx1⋅2OG⋅fumitremorgin B at a resolution of 1.22 Å. Our structures show that the binding of fumitremorgin B induces significant compression of the active pocket and that Y68 is in close proximity to C26 of the substrate. Further MD simulation and QM/MM calculations support a CarC-like mechanism, in which Y68 acts as the H atom donor for quenching the C26-centered substrate radical. Our results are consistent with all available experimental data and highlight the importance of accurate complex structures in the mechanistic study of enzymatic catalysis.
3. On the reaction mechanism of an endoperoxide ring formation by fumitremorgin B endoperoxidase. The right arrangement makes a difference
Anna Miłaczewska, Tomasz Borowski Dalton Trans. 2019 Nov 21;48(43):16211-16221. doi: 10.1039/c9dt02581b. Epub 2019 Oct 3.
Fumitremorgin B endoperoxidase (FtmF) belongs to 2-oxoglutarate dependent dioxygenases and catalyzes an unusual oxidative reaction of endoperoxide formation at the final stage of biosynthesis of verruculogen - a mycotoxin produced by Aspergillus and Penicillinum strains. The published crystal structure of FtmF (PDB: ), which is of overall good quality, contains a model of the substrate bound in the active site, which, however, has very low occupancy and its conformation does not comply with the small molecule crystal structure. Moreover, a previous computational study that employed a model based on this crystal structure revealed a substantial reaction barrier, which might indicate that the model of FtmF/substrate complex can have serious errors. The purpose of this work was to model with computational methods the structure of the enzyme-substrate complex and to investigate the mechanisms of the enzymatic reaction. Docking, molecular dynamics simulation and DFT results, all indicate the substrate most likely binds in the active site in a configuration very different from that originally suggested. Moreover, for this newly proposed structure of the enzyme-substrate complex, the reaction energy profile is characterised exclusively by low barriers and it successfully explains the observed regiospecificity of the enzymatic process. Finally, a plausible binding site for ascorbate was found and it is suggested that ascorbate is involved in the final step of the FtmF reaction.
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 ╳
