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Enniatin B1

Names

[ CAS No. ]:
19914-20-6

[ Name ]:
Enniatin B1

[Synonym ]:
1,7,13-Trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone, 4,10,16-trimethyl-3,6,9,12,18-pentakis(1-methylethyl)-15-[(1R)-1-methylpropyl]-, (3S,6R,9S,12R,15R,18R)-
1,7,13-Trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone, 4,10,16-trimethyl-3,6,9,12,18-pentakis(1-methylethyl)-15-[(1S)-1-methylpropyl]-, (3S,6R,9S,12R,15S,18R)-
(3R,6R,9S,12R,15S,18R)-3-[(2R)-2-Butanyl]-6,9,12,15,18-pentaisopropyl-4,10,16-trimethyl-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
(3S,6R,9S,12R,15S,18R)-3-[(2S)-2-Butanyl]-6,9,12,15,18-pentaisopropyl-4,10,16-trimethyl-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone

Biological Activity

[Description]:

Enniatin B1 is a Fusarium mycotoxin. Enniatin B1 inhibits acyl-CoA: cholesterol acyltransferase (ACAT) activity with an IC50 of 73 μM in an enzyme assay using rat liver microsomes[1]. Enniatin B1 crosss the blood-brain barrier[2]. Enniatin B1 decreases the activation of ERK (p44/p42). Enniatin B1 inhibits moderately TNF-α-induced NF-κB activation[3].

[Related Catalog]:

Research Areas >> Cancer
Research Areas >> Cardiovascular Disease
Research Areas >> Infection
Signaling Pathways >> MAPK/ERK Pathway >> ERK
Signaling Pathways >> Metabolic Enzyme/Protease >> Acyltransferase
Signaling Pathways >> Stem Cell/Wnt >> ERK

[Target]

ACAT

ERK

NF-κB


[In Vitro]

CCF-STTG1 cells are sensitive to Enniatin B1 (IC50=4.4 μM)[2].

[References]

[1]. Tomoda H, et al. Inhibition of acyl-CoA: cholesterol acyltransferase activity by cyclodepsipeptide antibiotics. J Antibiot (Tokyo). 1992 Oct;45(10):1626-32.

[2]. Krug I, et al. Transport of enniatin B and enniatin B1 across the blood-brain barrier and hints for neurotoxic effects in cerebral cells. PLoS One. 2018 May 16;13(5):e0197406.

[3]. Wätjen W, et al. Enniatins A1, B and B1 from an endophytic strain of Fusarium tricinctum induce apoptotic cell death in H4IIE hepatoma cells accompanied by inhibition of ERK phosphorylation. Mol Nutr Food Res. 2009 Apr;53(4):431-40.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
833.8±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C34H59N3O9

[ Molecular Weight ]:
653.847

[ Flash Point ]:
458.0±34.3 °C

[ Exact Mass ]:
653.425110

[ PSA ]:
139.83000

[ LogP ]:
3.58

[ Vapour Pressure ]:
0.0±3.1 mmHg at 25°C

[ Index of Refraction ]:
1.460

[ Storage condition ]:
?20°C

[ Water Solubility ]:
DMSO: soluble10mg/mL

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301-H311-H331

[ Precautionary Statements ]:
P261-P280-P301 + P310-P311

[ Hazard Codes ]:
T

[ Risk Phrases ]:
23/24/25

[ Safety Phrases ]:
45

[ RIDADR ]:
2811

[ Packaging Group ]:
I

Related Compounds