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...

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.