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SML0301

Hymeglusin

from Fusarium sp., ≥98% (HPLC), powder, HMG-CoA synthase inhibitor

Synonym(s):

(2E, 4E, 7R)-11-[(2R,3R)-3-(Hydroxymethyl)-4-oxooxetan-2-yl]-3,5,7-trimethylundeca-2,4-dienoic acid, Antibiotic 1233A, F-244, L-659,699

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Size/SKUAvailabilityPrice
1 mg

Available to ship TODAYfromMILWAUKEE

$416.00

About This Item

Empirical Formula (Hill Notation):
C18H28O5
CAS Number:
29066-42-0
Molecular Weight:
324.41
UNSPSC Code:
51111800
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
powder

$416.00

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Product Name

Hymeglusin, ≥98% (HPLC), from Fusarium sp.

biological source

Fusarium sp.

Quality Segment

200

assay

≥98% (HPLC)

form

powder

solubility

DMSO: soluble, H2O: insoluble, acetone: soluble, chloroform: soluble, ethyl acetate: soluble

storage temp.

−20°C

SMILES string

O1[C@@H]([C@H](C1=O)CO)CCCC[C@H](C\C(=C\C(=C\C(=O)O)\C)\C)C

InChI

1S/C18H28O5/c1-12(8-13(2)9-14(3)10-17(20)21)6-4-5-7-16-15(11-19)18(22)23-16/h9-10,12,15-16,19H,4-8,11H2,1-3H3,(H,20,21)/b13-9+,14-10+/t12-,15-,16-/m1/s1

InChI key

ODCZJZWSXPVLAW-KXCGKLMDSA-N

Biochem/physiol Actions

Hymeglusin is a specific β lactone inhibitor of eukaryotic hydroxymethylglutaryl-CoA synthase (HMGCS), a key enzyme in the cholesterol biosynthetic pathway.
Hymeglusin is a specific β lactone inhibitor of eukaryotic hydroxymethylglutaryl-CoA synthase (HMGCS), a key enzyme in the cholesterol biosynthetic pathway. Unlike other fungal metabolites, Hymeglusin inhibits mevalonate biosynthesis by acting on HMG-CoA synthase, while other fungal metabolites such as Lovastatin (Mevinolin) and Compactin act as specific competitive inhibitors of the HMG-CoA reductase. Inhibition results from covalent modification of the active Cys129 residue by the enzyme by the formation of a thioester adduct in the active site. Hymeglusin show no inhibitory effect against fatty acid synthetase purified from Sacharomyces serevisiae. Hymeglusin was found to block the growth of Enterococcus faecalis. After removal of the inhibitor from the culture medium, a growth curve inflection point is observed. Upon Hymeglusin inactivation, enzyme activity is restored at a rate that is 8-fold faster for human HMGCS than for the bacterial enzyme (mvaS). Structural studies explain these differences. Hymeglusin was also found to inhibit the replication of the dengue live virus (DEN-2 NGC virus) in K562 cells. Lovastatin inhibits DEN-2 NGC live virus replication in human peripheral blood mononuclear cells.

Preparation Note

A DMSO solution (1 mg/mL) is stable for one month at −20 °C.

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Hymeglusin ≥98% (HPLC), from Fusarium sp.

Sigma-Aldrich

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Hymeglusin

Silybin B phyproof® Reference Substance

PHL82654

Silybin B

Trichostatin A ≥98% (HPLC), from Streptomyces sp.

Sigma-Aldrich

T8552

Trichostatin A

WOBE437 ≥98% (HPLC)

Sigma-Aldrich

SML2110

WOBE437

description

≥98% (HPLC), from Fusarium sp.

description

phyproof® Reference Substance

description

≥98% (HPLC), from Streptomyces sp.

description

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98.0% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

form

powder

form

solid

form

powder

form

powder

Quality Level

200

Quality Level

-

Quality Level

300

Quality Level

-

storage temp.

−20°C

storage temp.

-

storage temp.

−20°C

storage temp.

2-8°C

solubility

DMSO: soluble, acetone: soluble, ethyl acetate: soluble, H2O: insoluble, chloroform: soluble

solubility

-

solubility

methanol: soluble 1.90-2.10 mg/mL, clear, colorless to faint yellow or tan, DMF: soluble, DMSO: soluble, H2O: insoluble, acetone: slightly soluble, acetonitrile: soluble, benzene: slightly soluble, chloroform: slightly soluble, ethyl acetate: slightly soluble, lower alcohols: soluble

solubility

DMSO: 2 mg/mL, clear

biological source

Fusarium sp.

biological source

-

biological source

Streptomyces sp.

biological source

-

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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