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SML0301

Sigma-Aldrich

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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About This Item

Empirical Formula (Hill Notation):
C18H28O5
CAS Number:
29066-42-0
Molecular Weight:
324.41
UNSPSC Code:
51111800
NACRES:
NA.77

product name

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

biological source

Fusarium sp.

Quality Level

200

Assay

≥98% (HPLC)

form

powder

solubility

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

storage temp.

−20°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. 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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Specific binding of beta-lactone 1233A to 3-hydroxy-3-methylglutaryl-coenzyme A synthase.
H Tomoda et al.
The Journal of antibiotics, 46(5), 872-874 (1993-05-01)
M D Greenspan et al.
Proceedings of the National Academy of Sciences of the United States of America, 84(21), 7488-7492 (1987-11-01)
A beta-lactone isolated from Fusarium sp. has been shown to be a potent specific inhibitor of the enzyme 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase [(S)-3-hydroxy-3-methylglutaryl-CoA acetoacetyl-CoA-lyase (CoA-acetylating), EC, 4.1.3.5] from rat liver. The structure of this beta-lactone, termed L-659,699, is (E,E)-11-[3-(hydroxy-methyl)-4-oxo-2-oxytanyl]-3,5,7-trimethyl-2,4
T Sunazuka et al.
The Journal of antibiotics, 45(7), 1139-1147 (1992-07-01)
Simple and efficient syntheses of 1233A analogs were developed and the inhibitory activity of the analogs against hydroxymethylglutaryl coenzyme A (HMG-CoA) synthase was determined. Study of the structure-activity relationships revealed that not only the geometry in beta-lactone moiety but also
D Andrew Skaff et al.
Biochemistry, 51(23), 4713-4722 (2012-04-19)
Hymeglusin (1233A, F244, L-659-699) is established as a specific β-lactone inhibitor of eukaryotic hydroxymethylglutaryl-CoA synthase (HMGCS). Inhibition results from formation of a thioester adduct to the active site cysteine. In contrast, the effects of hymeglusin on bacterial HMG-CoA synthase, mvaS
H Hashizume et al.
Chemical & pharmaceutical bulletin, 42(10), 2097-2107 (1994-10-01)
Structural analogs of 1233A, a microbial metabolite inhibiting 3-hydroxy-3- methylglutaryl coenzyme A (HMG-CoA) synthase, were designed and synthesized. The 2-oxetanone moiety was left intact. All analogs prepared were tested for inhibition of HMG-CoA synthase activity and sterol synthesis in mouse
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