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M1177

Sigma-Aldrich

Myriocin

from Mycelia sterilia, ≥98% (HPLC), powder, immunosuppressant

Synonym(s):

(2S,3R,4R,6E)-2-Amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-6-eicosenoic acid, ISP-I, Thermozymocidin

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About This Item

Empirical Formula (Hill Notation):
C21H39NO6
CAS Number:
35891-70-4
Molecular Weight:
401.54
MDL number:
MFCD01632772
UNSPSC Code:
51111800
PubChem Substance ID:
24896622
NACRES:
NA.77

Key Documents

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Product Name

Myriocin from Mycelia sterilia, ≥98% (HPLC), powder

Quality Level

200

assay

≥98% (HPLC)

form

powder

color

off-white

solubility

methanol: 2 mg/mL

storage temp.

2-8°C

SMILES string

CCCCCCC(=O)CCCCCC\C=C\C[C@@H](O)[C@H](O)[C@@](N)(CO)C(O)=O

InChI

1S/C21H39NO6/c1-2-3-4-10-13-17(24)14-11-8-6-5-7-9-12-15-18(25)19(26)21(22,16-23)20(27)28/h9,12,18-19,23,25-26H,2-8,10-11,13-16,22H2,1H3,(H,27,28)/b12-9+/t18-,19+,21+/m1/s1

Inchi Key

ZZIKIHCNFWXKDY-GNTQXERDSA-N

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This Item
476300SML1945C1017
Myriocin from Mycelia sterilia ≥98% (HPLC), powder

Sigma-Aldrich

M1177

Myriocin from Mycelia sterilia

Myriocin, Mycelia sterilia A potent immunosuppressant.

Sigma-Aldrich

476300

Myriocin, Mycelia sterilia

IMB-808 ≥98% (HPLC)

Sigma-Aldrich

SML1945

IMB-808

Citrinin from Penicillium citrinum, ≥98% (HPLC)

Sigma-Aldrich

C1017

Citrinin

form

powder

form

solid

form

powder

form

powder

assay

≥98% (HPLC)

assay

≥95% (TLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

Quality Level

200

Quality Level

100

Quality Level

-

Quality Level

200

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

methanol: 2 mg/mL

solubility

DMSO: 25 mg/mL

solubility

DMSO: 2 mg/mL, clear

solubility

-

color

off-white

color

white

color

white to beige

color

-

Application

Myriocin from Mycelia sterilia has been used as an inhibitor of sphingolipid or ceramide biosynthesis in various studies.[1][2][3]

Biochem/physiol Actions

Myriocin from Mycelia sterilia is a fungal metabolite with potent immunosuppressant activity. It inhibits serine palmitoyltransferase at picomolar concentrations blocking synthesis of ceramide, a precursor of sphingomyelin and glycosphingolipids. It disrupts substratum adhesion of melanoma cells. It has been suggested that its immunosuppressant activity in the cytotoxic T-cell line CTTL-2 is due to apoptosis induction.

Preparation Note

The material is readily and completely dissolved in 2 mg/ml methanol after heating at 55°C for several minutes.

Pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000488206
0000488206
0000448170
0000448170
0000420494

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John R Ussher et al.
PloS one, 7(5), e37703-e37703 (2012-05-26)
Diet-induced obesity (DIO) leads to an accumulation of intra-myocardial lipid metabolites implicated in causing cardiac insulin resistance and contractile dysfunction. One such metabolite is ceramide, and our aim was to determine the effects of inhibiting de novo ceramide synthesis on
Fernando Martínez-Montañés et al.
Journal of lipid research, 57(11), 2040-2050 (2016-11-03)
Long-chain bases (LCBs) are the precursors to ceramide and sphingolipids in eukaryotic cells. They are formed by the action of serine palmitoyl-CoA transferase (SPT), a complex of integral membrane proteins located in the endoplasmic reticulum. SPT activity is negatively regulated
Lipopolysaccharide disrupts mitochondrial physiology in skeletal muscle via disparate effects on sphingolipid metabolism
Hansen ME, et al.
Shock, 44(6), 585-585 (2015)
Maija Ruuth et al.
European heart journal, 39(27), 2562-2573 (2018-07-10)
Low-density lipoprotein (LDL) particles cause atherosclerotic cardiovascular disease (ASCVD) through their retention, modification, and accumulation within the arterial intima. High plasma concentrations of LDL drive this disease, but LDL quality may also contribute. Here, we focused on the intrinsic propensity
Quan-Jiang Zhang et al.
Diabetes, 61(7), 1848-1859 (2012-05-16)
Vascular dysfunction that accompanies obesity and insulin resistance may be mediated by lipid metabolites. We sought to determine if vascular ceramide leads to arterial dysfunction and to elucidate the underlying mechanisms. Pharmacological inhibition of de novo ceramide synthesis, using the
View All Related Papers

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