FB1

Names

[ Name ]:
FB1

[Synonym ]:
2,2'-{(19-amino-11,16,18-trihydroxy-5,9-dimethylicosane-6,7-diyl)bis[oxy(2-oxoethane-2,1-diyl)]}dibutanedioic acid
Fumonisin B1 from Fusarium moniliforme,Macrofusine
Fumonisin B1
FB1
1,2,3-Propanetricarboxylic acid, 1,1'-[1-(12-amino-4,9,11-trihydroxy-2-methyltridecyl)-2-(1-methylpentyl)-1,2-ethanediyl] ester
2,2'-{(19-Amino-11,16,18-trihydroxy-5,9-dimethylicosane-6,7-diyl)bis[oxy(2-oxoethane-2,1-diyl)]}disuccinic acid
(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(2-oxoethane-2,1-diyl)]}disuccinic acid
1,2,3-Propanetricarboxylic Acid 1,1'-[1-(12-amino-4,9,11-trihydroxy-2-methyltridecyl)-2-(1-methylpentyl)-1,2-ethanediyl] Ester
Fumonisin B1,1,1'-[(1S,2R)-1-[(2S,4R,9R,11S,12S)-12-Amino-4,9,11-trihydroxy-2-methyltridecyl]-2-[(1R)-1-methylpentyl]-1,2-ethanediyl-1,2,3-(2R,2'R)-propanetricarboxylicacidester.
(2R,2'R)-2,2'-{[(5R,6R,7S,9S,11R,16R,18S,19S)-19-Amino-11,16,18-trihydroxy-5,9-dimethyl-6,7-icosanediyl]bis[oxy(2-oxo-2,1-ethanediyl)]}disuccinic acid
1,2,3-Propanetricarboxylic acid, 1-[(1S,3S,5R,10R,12S,13S)-13-amino-1-[(1R,2R)-1-[(3R)-3,4-dicarboxy-1-oxobutoxy]-2-methylhexyl]-5,10,12-trihydroxy-3-methyltetradecyl] ester, (2R)-
2,2'-{(19-Amino-11,16,18-trihydroxy-5,9-dimethyl-6,7-icosanediyl)bis[oxy(2-oxo-2,1-ethanediyl)]}disuccinic acid

Biological Activity

[Description]:

Fumonisin B1 is a mycotoxin produced from Fusarium moniliforme. Fumonisin B1 is a potent inhibitor of sphingosine N-acyltransferase (ceramide synthase) and disrupts de novo sphingolipid biosynthesis. Fumonisin B1 is the most abundant and toxic fumonisin[1][2].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Others >> Others

[Target]

Sphingosine N-acyltransferase[2]

[In Vitro]

Fumonisin B1 alters the gene expression and signal transduction pathways in monkey kidney cells[3]. Fumonisin B1 increases the initial disruption of sphingolipid metabolism and the accumulation of sphinganine in LLC-PK1 kidney cells, causes DNA damage of apoptotic type in rat astrocytes[3].

[References]

[1]. Henry MH, et al. The toxicity of fumonisin B1, B2, and B3, individually and in combination, in chicken embryos. Poult Sci. 2001 Apr;80(4):401-7.

[2]. Shephard GS, et al. Disruption of sphingolipid metabolism in non-human primates consuming diets of fumonisin-containing Fusarium moniliforme culture material. Toxicon. 1996 May;34(5):527-34.

[3]. Wang SK, et al. Effect of fumonisin B₁ on the cell cycle of normal human liver cells. Mol Med Rep. 2013 Jun;7(6):1970-6.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
924.9±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C₃₄H₅₉NO₁₅

[ Molecular Weight ]:
721.830

[ Flash Point ]:
513.2±34.3 °C

[ Exact Mass ]:
721.388489

[ PSA ]:
288.51000

[ LogP ]:
2.20

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.528

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TZ8350000

CHEMICAL NAME :: 1,2,3-Propanetricarboxylic acid, 1,1'-(1-(12-amino-4,9,11-trihydroxy-2-methyltridecyl) -2- (1-methylpentyl)-1,2-ethanediyl)ester

CAS REGISTRY NUMBER :: 116355-83-0

LAST UPDATED :: 199807

DATA ITEMS CITED :: 18

MOLECULAR FORMULA :: C34-H59-N-O15

MOLECULAR WEIGHT :: 721.94

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 399 mg/kg/21D-I

TOXIC EFFECTS :: Liver - changes in liver weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 175 mg/kg/13W-C

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Kidney, Ureter, Bladder - changes in bladder weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 350 mg/kg/14D-I

TOXIC EFFECTS :: Blood - changes in spleen Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 582 mg/kg/2Y-C

TOXIC EFFECTS :: Liver - other changes Liver - changes in liver weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 30 mg/kg/4D-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Kidney, Ureter, Bladder - other changes in urine composition Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - dehydrogenases

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 884 mg/kg/13W-C

TOXIC EFFECTS :: Liver - multiple effects Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - multiple enzyme effects

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1050 mg/kg/14D-I

TOXIC EFFECTS :: Liver - changes in liver weight Blood - changes in bone marrow (not otherwise specified) Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 16 mg/kg/6D-I

TOXIC EFFECTS :: Liver - other changes Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 150 mg/kg

SEX/DURATION :: female 8-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 900 mg/kg

SEX/DURATION :: female 7-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 225 mg/kg

SEX/DURATION :: female 7-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 900 mg/kg

SEX/DURATION :: female 7-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 900 mg/kg

SEX/DURATION :: female 7-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 12 mg/kg

SEX/DURATION :: female 8-9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Rodent - rat Liver

DOSE/DURATION :: 1 mg/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 391,39,1997 *** REVIEWS *** IARC Cancer Review:Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 56,445,1993

Safety Information

[ Symbol ]:

GHS02, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H319

[ Precautionary Statements ]:
P210-P305 + P351 + P338-P370 + P378-P403 + P235

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
T: Toxic;Xn: Harmful;F: Flammable;

[ Risk Phrases ]:
R40

[ Safety Phrases ]:
36/37-16

[ RIDADR ]:
UN 3172

[ WGK Germany ]:
3

[ RTECS ]:
TZ8350000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
29221990

Articles

Deoxynivalenol-mimic nanobody isolated from a naïve phage display nanobody library and its application in immunoassay.

Anal. Chim. Acta 887 , 201-8, (2015)

In this study, using mycotoxin deoxynivalenol (DON) as a model hapten, we developed a nanobody-based environmental friendly immunoassay for sensitive detection of DON. Two nanobodies (N-28 and N-31) w...

The novel HDAC inhibitor AR-42-induced anti-colon cancer cell activity is associated with ceramide production.

Biochem. Biophys. Res. Commun. 463 , 545-50, (2015)

In the current study, we investigated the potential activity of AR-42, a novel histone deacetylase (HDAC) inhibitor, against colon cancer cells. Our in vitro results showed that AR-42 induced ceramide...

Fumonisin measurement from maize samples by high-performance liquid chromatography coupled with corona charged aerosol detector.

J. Chromatogr. Sci. 52(10) , 1181-5, (2014)

Fumonisins are a class of mycotoxins produced mainly by Fusarium species, which is primary fungal contaminant of the maize and maize-derived products around the world. The B-series fumonisins (FB1, FB...

FB1