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Fumitremorgin B

CAS# 12626-17-4

Fumitremorgin B

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Quality Control of Fumitremorgin B

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Chemical structure

Fumitremorgin B

3D structure

Chemical Properties of Fumitremorgin B

Cas No. 12626-17-4 SDF Download SDF
PubChem ID 105113 Appearance Powder
Formula C27H33N3O5 M.Wt 479.57
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES CC(=CCN1C2=C(C=CC(=C2)OC)C3=C1C(N4C(=O)C5CCCN5C(=O)C4(C3O)O)C=C(C)C)C
Standard InChIKey WEIYXEFMCIRZHC-MWGWWEMPSA-N
Standard 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Fumitremorgin B

The fermentation broth of Aspergillus fumigatus LN-4.

Biological Activity of Fumitremorgin B

Description1. Fumitremorgen B is a mycotoxin, it exhibits a certain degree of genotoxicity, it can cause DNA damage in human lymphocytes. 2. Fumitremorgin B exhibits antifungal activities, it also shows significant toxicity toward brine shrimps,with the median lethal concentration (LC(50)) value of 13.6 ug/mL. 3. Fumitremorgin B possess antifeedant activity against armyworm larvae. 4. Fumitremorgin B shows an inhibitory activity on the cell cycle progression of mouse tsFT210 cells in the M phase, with the MIC value of 26.1 microM.
TargetsAntifection

Fumitremorgin B Dilution Calculator

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Fumitremorgin B Molarity Calculator

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Preparing Stock Solutions of Fumitremorgin B

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.0852 mL 10.426 mL 20.852 mL 41.704 mL 52.13 mL
5 mM 0.417 mL 2.0852 mL 4.1704 mL 8.3408 mL 10.426 mL
10 mM 0.2085 mL 1.0426 mL 2.0852 mL 4.1704 mL 5.213 mL
50 mM 0.0417 mL 0.2085 mL 0.417 mL 0.8341 mL 1.0426 mL
100 mM 0.0209 mL 0.1043 mL 0.2085 mL 0.417 mL 0.5213 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Fumitremorgin B

Genotoxicity assessment of five tremorgenic mycotoxins (fumitremorgen B, paxilline, penitrem A, verruculogen, and verrucosidin) produced by molds isolated from fermented meats.[Pubmed:14627292]

J Food Prot. 2003 Nov;66(11):2123-9.

A number of toxinogenic fungal species, particularly producers of tremorgenic mycotoxins, have been isolated from traditional fermented meats. Tremorgenic mycotoxins are a group of fungal metabolites known to act on the central nervous system, causing sustained tremors, convulsions, and death in animals. However, the mode of action of these mycotoxins has not been elucidated in detail, and their genotoxic capacity has hardly been investigated. Because genotoxicity is one of the most prominent toxicological end points in food safety testing, we assessed the genotoxicity of five tremorgenic mycotoxins (fumitremorgen B, paxilline, penitrem A, verrucosidin, and verruculogen) associated with molds found in fermented meats. The mycotoxins were tested in two short-term in vitro assays with the use of different genotoxic end points in different phylogenetic systems (the Ames Salmonella/mammalian-microsome assay and the single-cell gel electrophoresis assay of human lymphocytes). According to the results obtained in this study, all of the investigated mycotoxins except penitrem A exhibited a certain degree of genotoxicity. Verrucosidin appeared to have the highest toxic potential, testing positive in both assays. Verruculogen tested positive in the Salmonella/mammalian-microsome assay, and paxilline and fumitremorgen B caused DNA damage in human lymphocytes. The use of fungal starter cultures to avoid tremorgen contamination in fermented meats is recommended.

Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus. I. Taxonomy, fermentation, isolation and biological properties.[Pubmed:8698634]

J Antibiot (Tokyo). 1996 Jun;49(6):527-33.

Two novel diketopiperazines named tryprostatins A (1) and B (2) and a new natural product belonging to the diketopiperazine series, designated as demethoxyfumitremorgin C (3), together with four known diketopiperazines, fumitremorgin C (4), 12,13-dihydroxyfumitremorgin C (5), Fumitremorgin B (6) and verruculogen (7), were isolated from the fermentation broth of Aspergillus fumigatus BM939 by the combined use of solvent extraction, silica gel column chromatography, preparative TLC and repeated-preparative HPLC. The diketopiperazines showed an inhibitory activity on the cell cycle progression of mouse tsFT210 cells in the M phase with the MIC values of 16.4 microM (1), 4.4 microM (2), 0.45 microM (3), 4.1 microM (4), 60.8 microM (5), 26.1 microM (6) and 12.2 microM (7), respectively.

Metabolites from Aspergillus fumigatus, an endophytic fungus associated with Melia azedarach, and their antifungal, antifeedant, and toxic activities.[Pubmed:22409377]

J Agric Food Chem. 2012 Apr 4;60(13):3424-31.

Thirty-nine fungal metabolites 1-39, including two new alkaloids, 12beta-hydroxy-13alpha-methoxyverruculogen TR-2 (6) and 3-hydroxyfumiquinazoline A (16), were isolated from the fermentation broth of Aspergillus fumigatus LN-4, an endophytic fungus isolated from the stem bark of Melia azedarach. Their structures were elucidated on the basis of detailed spectroscopic analysis (mass spectrometry and one- and two-dimensional NMR experiments) and by comparison of their NMR data with those reported in the literature. These isolated compounds were evaluated for in vitro antifungal activities against some phytopathogenic fungi, toxicity against brine shrimps, and antifeedant activities against armyworm larvae (Mythimna separata Walker). Among them, sixteen compounds showed potent antifungal activities against phytopathogenic fungi (Botrytis cinerea, Alternaria solani, Alternaria alternata, Colletotrichum gloeosporioides, Fusarium solani, Fusarium oxysporum f. sp. niveum, Fusarium oxysporum f. sp. vasinfectum, and Gibberella saubinettii), and four of them, 12beta-hydroxy-13alpha-methoxyverruculogen TR-2 (6), Fumitremorgin B (7), verruculogen (8), and helvolic acid (39), exhibited antifungal activities with MIC values of 6.25-50 mug/mL, which were comparable to the two positive controls carbendazim and hymexazol. In addition, of eighteen that exerted moderate lethality toward brine shrimps, compounds 7 and 8 both showed significant toxicities with median lethal concentration (LC(50)) values of 13.6 and 15.8 mug/mL, respectively. Furthermore, among nine metabolites that were found to possess antifeedant activity against armyworm larvae, compounds 7 and 8 gave the best activity with antifeedant indexes (AFI) of 50.0% and 55.0%, respectively. Structure-activity relationships of the metabolites were also discussed.

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