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MedKoo Cat#: 540144 | Name: Fumonisin B1
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Fumonisin B1 is a mycotoxin and grain contaminant. It inhibits sphingosine acyltransferase and disrupts sphingolipid metabolism. It is less toxic than fumonisin B2.

Chemical Structure

Fumonisin B1
Fumonisin B1
CAS#116355-83-0

Theoretical Analysis

MedKoo Cat#: 540144

Name: Fumonisin B1

CAS#: 116355-83-0

Chemical Formula: C34H59NO15

Exact Mass: 721.3885

Molecular Weight: 721.83

Elemental Analysis: C, 56.57; H, 8.24; N, 1.94; O, 33.25

Price and Availability

Size Price Availability Quantity
5mg USD 550.00 Ready to ship
10mg USD 950.00 2 Weeks
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Related CAS #
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Synonym
Fumonisin-B1; Macrofusine; Fumonisin B(1); FB1; NSC 629151; NSC629151; NSC-629151
IUPAC/Chemical Name
(2R,2'R)-2,2'-((((5R,6R,7S,9S,11R,16R,18S,19S)-19-amino-11,16,18-trihydroxy-5,9-dimethylicosane-6,7-diyl)bis(oxy))bis(2-oxoethane-2,1-diyl))disuccinic acid
InChi Key
UVBUBMSSQKOIBE-DSLOAKGESA-N
InChi Code
InChI=1S/C34H59NO15/c1-5-6-9-20(3)32(50-31(44)17-23(34(47)48)15-29(41)42)27(49-30(43)16-22(33(45)46)14-28(39)40)13-19(2)12-24(36)10-7-8-11-25(37)18-26(38)21(4)35/h19-27,32,36-38H,5-18,35H2,1-4H3,(H,39,40)(H,41,42)(H,45,46)(H,47,48)/t19-,20+,21-,22+,23+,24+,25+,26-,27-,32+/m0/s1
SMILES Code
CCCC[C@H]([C@H]([C@@H](OC(C[C@H](C(O)=O)CC(O)=O)=O)C[C@H](C[C@@H](CCCC[C@H](C[C@@H]([C@@H](N)C)O)O)O)C)OC(C[C@H](C(O)=O)CC(O)=O)=O)C
Appearance
Solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#C21M11C29
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Fumonisin B1 is an inhibitor of sphingosine N-acyltransferase (ceramide synthase) and disrupts de novo sphingolipid biosynthesis.
In vitro activity:
FB1 (fumonisin B1) treatment also increased endoplasmic reticulum stress due to the rapid increase of calcium ions and ROS levels. In addition, FB1 induced massive DNA damage and chromatin decondensation. Reference: Food Chem Toxicol. 2021 Aug;154:112326. https://pubmed.ncbi.nlm.nih.gov/34111490/
In vivo activity:
For these purposes, adult male C57BL/6 mice were injected with FB1 (fumonisin B1) (8 mg/kg, i.p.) or its vehicle and 30 min thereafter received with a low dose of the classical convulsant pentylenetetrazol (PTZ, 30 mg/kg, i.p.) or its vehicle. After behavioral evaluation the cerebral cortex and the hippocampus were collected for analysis of Na(+),K(+)-ATPase activity, mitochondrial membrane potential (ΔΨm) and mitochondrial complex I and II activities. FB1 reduced the latency for PTZ-induced myoclonic jerks and increased the number of these events. Altogether, present results indicate that FB1 causes brain hyperexcitability in vivo, and that mitochondrial dysfunction may represent a potential underlying mechanism. Reference: Neurotoxicol Teratol. 2015 Sep-Oct;51:61-7. https://pubmed.ncbi.nlm.nih.gov/26342287/
Solvent mg/mL mM
Solubility
DMSO 6.1 8.46
DMF 5.0 6.93
Ethanol 10.0 13.85
PBS (pH 7.2) 1.0 1.39
Water 16.7 23.09
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 721.83 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Paul S, Jakhar R, Bhardwaj M, Chauhan AK, Kang SC. Fumonisin B1 induces poly (ADP-ribose) (PAR) polymer-mediated cell death (parthanatos) in neuroblastoma. Food Chem Toxicol. 2021 Aug;154:112326. doi: 10.1016/j.fct.2021.112326. Epub 2021 Jun 7. PMID: 34111490. 2. Yu S, Jia B, Liu N, Yu D, Zhang S, Wu A. Fumonisin B1 triggers carcinogenesis via HDAC/PI3K/Akt signalling pathway in human esophageal epithelial cells. Sci Total Environ. 2021 Sep 15;787:147405. doi: 10.1016/j.scitotenv.2021.147405. Epub 2021 Apr 30. PMID: 34000555. 3. Bódi V, Csikós V, Rátkai EA, Szűcs A, Tóth A, Szádeczky-Kardoss K, Dobolyi Á, Schlett K, Világi I, Varró P. Short-term neuronal effects of fumonisin B1 on neuronal activity in rodents. Neurotoxicology. 2020 Sep;80:41-51. doi: 10.1016/j.neuro.2020.06.007. Epub 2020 Jun 16. PMID: 32561249. 4. Poersch AB, Trombetta F, Souto NS, de Oliveira Lima C, Braga AC, Dobrachinski F, Ribeiro LR, Soares FA, Fighera MR, Royes LF, Oliveira MS, Furian AF. Fumonisin B1 facilitates seizures induced by pentylenetetrazol in mice. Neurotoxicol Teratol. 2015 Sep-Oct;51:61-7. doi: 10.1016/j.ntt.2015.08.007. Epub 2015 Sep 2. PMID: 26342287.
In vitro protocol:
1. Paul S, Jakhar R, Bhardwaj M, Chauhan AK, Kang SC. Fumonisin B1 induces poly (ADP-ribose) (PAR) polymer-mediated cell death (parthanatos) in neuroblastoma. Food Chem Toxicol. 2021 Aug;154:112326. doi: 10.1016/j.fct.2021.112326. Epub 2021 Jun 7. PMID: 34111490. 2. Yu S, Jia B, Liu N, Yu D, Zhang S, Wu A. Fumonisin B1 triggers carcinogenesis via HDAC/PI3K/Akt signalling pathway in human esophageal epithelial cells. Sci Total Environ. 2021 Sep 15;787:147405. doi: 10.1016/j.scitotenv.2021.147405. Epub 2021 Apr 30. PMID: 34000555.
In vivo protocol:
1. Bódi V, Csikós V, Rátkai EA, Szűcs A, Tóth A, Szádeczky-Kardoss K, Dobolyi Á, Schlett K, Világi I, Varró P. Short-term neuronal effects of fumonisin B1 on neuronal activity in rodents. Neurotoxicology. 2020 Sep;80:41-51. doi: 10.1016/j.neuro.2020.06.007. Epub 2020 Jun 16. PMID: 32561249. 2. Poersch AB, Trombetta F, Souto NS, de Oliveira Lima C, Braga AC, Dobrachinski F, Ribeiro LR, Soares FA, Fighera MR, Royes LF, Oliveira MS, Furian AF. Fumonisin B1 facilitates seizures induced by pentylenetetrazol in mice. Neurotoxicol Teratol. 2015 Sep-Oct;51:61-7. doi: 10.1016/j.ntt.2015.08.007. Epub 2015 Sep 2. PMID: 26342287.
1: Jebali A, Yasini Ardakani SA, Shahdadi H, Balal Zadeh MH, Hekmatimoghaddam S. Modification of nanocellulose by poly-lysine can inhibit the effect of fumonisin B1 on mouse liver cells. Colloids Surf B Biointerfaces. 2015 Feb 1;126:437-43. doi: 10.1016/j.colsurfb.2014.12.047. Epub 2015 Jan 3. PubMed PMID: 25601749. 2: Magoha H, De Meulenaer B, Kimanya M, Hipolite D, Lachat C, Kolsteren P. Fumonisin B1 contamination in breast milk and its exposure in infants under 6 months of age in Rombo, Northern Tanzania. Food Chem Toxicol. 2014 Dec;74:112-6. doi: 10.1016/j.fct.2014.09.008. Epub 2014 Sep 30. PubMed PMID: 25280923. 3: Torres O, Matute J, Gelineau-van Waes J, Maddox JR, Gregory SG, Ashley-Koch AE, Showker JL, Zitomer NC, Voss KA, Riley RT. Urinary fumonisin B1 and estimated fumonisin intake in women from high- and low-exposure communities in Guatemala. Mol Nutr Food Res. 2014 May;58(5):973-83. doi: 10.1002/mnfr.201300481. Epub 2013 Dec 23. PubMed PMID: 24375966. 4: Cirlini M, Hahn I, Varga E, Dall'Asta M, Falavigna C, Calani L, Berthiller F, Del Rio D, Dall'Asta C. Hydrolysed fumonisin B1 and N-(deoxy-D-fructos-1-yl)-fumonisin B1: stability and catabolic fate under simulated human gastrointestinal conditions. Int J Food Sci Nutr. 2015 Feb;66(1):98-103. doi: 10.3109/09637486.2014.979316. Epub 2014 Dec 4. PubMed PMID: 25472591. 5: Poersch AB, Trombetta F, Souto NS, de Oliveira Lima C, Braga AC, Dobrachinski F, Ribeiro LR, Soares FA, Fighera MR, Royes LF, Oliveira MS, Furian AF. Fumonisin B1 facilitates seizures induced by pentylenetetrazol in mice. Neurotoxicol Teratol. 2015 Sep-Oct;51:61-7. doi: 10.1016/j.ntt.2015.08.007. Epub 2015 Sep 2. PubMed PMID: 26342287. 6: Cortinovis C, Caloni F, Schreiber NB, Spicer LJ. Effects of fumonisin B1 alone and combined with deoxynivalenol or zearalenone on porcine granulosa cell proliferation and steroid production. Theriogenology. 2014 May;81(8):1042-9. doi: 10.1016/j.theriogenology.2014.01.027. Epub 2014 Jan 30. PubMed PMID: 24576714. 7: Harrer H, Laviad EL, Humpf HU, Futerman AH. Identification of N-acyl-fumonisin B1 as new cytotoxic metabolites of fumonisin mycotoxins. Mol Nutr Food Res. 2013 Mar;57(3):516-22. doi: 10.1002/mnfr.201200465. Epub 2012 Dec 23. PubMed PMID: 23281112. 8: Peluque E, Neres NB, Michelin EC, Reis TA, Rosim RE, Oliveira CA, Sousa RL, Corrêa B, Fernandes AM. Fumonisin B1 in cereal mixtures marketed in Brazil. Food Addit Contam Part B Surveill. 2014;7(1):46-8. doi: 10.1080/19393210.2013.841294. Epub 2013 Oct 25. PubMed PMID: 24779980. 9: Ling S, Wang R, Gu X, Wen C, Chen L, Chen Z, Chen QA, Xiao S, Yang Y, Zhuang Z, Wang S. Rapid detection of fumonisin B1 using a colloidal gold immunoassay strip test in corn samples. Toxicon. 2015 Dec 15;108:210-5. doi: 10.1016/j.toxicon.2015.10.014. Epub 2015 Oct 23. PubMed PMID: 26525659. 10: Clarke R, Connolly L, Frizzell C, Elliott CT. Cytotoxic assessment of the regulated, co-existing mycotoxins aflatoxin B1, fumonisin B1 and ochratoxin, in single, binary and tertiary mixtures. Toxicon. 2014 Nov;90:70-81. doi: 10.1016/j.toxicon.2014.07.019. Epub 2014 Aug 7. PubMed PMID: 25110174. 11: Sancak D, Ozden S. Global histone modifications in Fumonisin B1 exposure in rat kidney epithelial cells. Toxicol In Vitro. 2015 Oct;29(7):1809-15. doi: 10.1016/j.tiv.2015.07.019. Epub 2015 Jul 21. PubMed PMID: 26208285. 12: Antonissen G, Devreese M, Van Immerseel F, De Baere S, Hessenberger S, Martel A, Croubels S. Chronic exposure to deoxynivalenol has no influence on the oral bioavailability of fumonisin B1 in broiler chickens. Toxins (Basel). 2015 Feb 16;7(2):560-71. doi: 10.3390/toxins7020560. PubMed PMID: 25690690; PubMed Central PMCID: PMC4344641. 13: Gui H, Jin Q, Zhang Y, Wang X, Yang Y, Shao C, Cheng C, Wei F, Yang Y, Yang M, Song H. [Development of an aptamer/fluorescence dye PicoGreen-based method for detection of fumonisin B1]. Sheng Wu Gong Cheng Xue Bao. 2015 Sep;31(9):1393-400. Chinese. PubMed PMID: 26955717. 14: Denli M, Blandon JC, Salado S, Guynot ME, Casas J, Pérez JF. Efficacy of AdiDetox™ in reducing the toxicity of fumonisin B1 in rats. Food Chem Toxicol. 2015 Apr;78:60-3. doi: 10.1016/j.fct.2015.01.024. Epub 2015 Feb 4. PubMed PMID: 25660482. 15: Ren W, Huang Z, Xu Y, Li Y, Ji Y, Su B. Urchin-like gold nanoparticle-based immunochromatographic strip test for rapid detection of fumonisin B1 in grains. Anal Bioanal Chem. 2015 Sep;407(24):7341-8. doi: 10.1007/s00216-015-8896-7. Epub 2015 Aug 22. PubMed PMID: 26297453. 16: Zhang J, Qiao Y, Wang X, Pei J, Zheng J, Zhang B. [Absorption of fumonisin B1 and B2 by Lactobacillus plantarum ZJ8]. Wei Sheng Wu Xue Bao. 2014 Dec 4;54(12):1481-8. Chinese. PubMed PMID: 25876334. 17: Loiseau N, Polizzi A, Dupuy A, Therville N, Rakotonirainy M, Loy J, Viadere JL, Cossalter AM, Bailly JD, Puel O, Kolf-Clauw M, Bertrand-Michel J, Levade T, Guillou H, Oswald IP. New insights into the organ-specific adverse effects of fumonisin B1: comparison between lung and liver. Arch Toxicol. 2015 Sep;89(9):1619-29. doi: 10.1007/s00204-014-1323-6. Epub 2014 Aug 26. PubMed PMID: 25155190. 18: Chuturgoon A, Phulukdaree A, Moodley D. Fumonisin B1 induces global DNA hypomethylation in HepG2 cells - An alternative mechanism of action. Toxicology. 2014 Jan 6;315:65-9. doi: 10.1016/j.tox.2013.11.004. Epub 2013 Nov 23. PubMed PMID: 24280379. 19: Zhao Y, Wang J, Liu Y, Miao H, Cai C, Shao Z, Guo R, Sun B, Jia C, Zhang L, Gigolashvili T, Wang Q. Classic myrosinase-dependent degradation of indole glucosinolate attenuates fumonisin B1-induced programmed cell death in Arabidopsis. Plant J. 2015 Mar;81(6):920-33. doi: 10.1111/tpj.12778. PubMed PMID: 25645692. 20: Minervini F, Garbetta A, D'Antuono I, Cardinali A, Martino NA, Debellis L, Visconti A. Toxic mechanisms induced by fumonisin b1 mycotoxin on human intestinal cell line. Arch Environ Contam Toxicol. 2014 Jul;67(1):115-23. doi: 10.1007/s00244-014-0004-z. Epub 2014 Feb 19. PubMed PMID: 24549592.