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Safety Information

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

SML0301-BULK:
SML0301-VAR:
SML0301-1MG:
SML0301-1MG-PW:

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Certificates of Analysis (COA)

Lot/Batch Number
072M4036V
14120508
32120502
32120501

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H Tomoda et al.
The Kitasato archives of experimental medicine, 65 Suppl, 1-12 (1993-04-01)
Thiotetromycin is isolated from Streptomyces sp. OM-674 discovered in the course of the screening for antibacterial antibiotics. The antibiotic was found to be a specific inhibitor of type II fatty acid synthase. In order to search acyl-CoA synthetase inhibitors, a
Potent inhibitory effect of antibiotic 1233A on cholesterol biosynthesis which specifically blocks 3-hydroxy-3-methylglutaryl coenzyme A synthase.
S Omura et al.
The Journal of antibiotics, 40(9), 1356-1357 (1987-09-01)
N Aboushadi et al.
Biochemistry, 39(1), 237-247 (2000-01-08)
We have previously identified a CHO cell line (UT2 cells) that expresses only one 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase protein which is localized exclusively in peroxisomes [Engfelt, H.W., Shackelford, J.E., Aboushadi, N., Jessani, N., Masuda, K., Paton, V.G., Keller, G.A.
Dinesh A Nagegowda et al.
The Biochemical journal, 383(Pt. 3), 517-527 (2004-07-06)
3-hydroxy-3-methylglutaryl (HMG)-CoA synthase (HMGS; EC 2.3.3.10) is the second enzyme in the cytoplasmic mevalonate pathway of isoprenoid biosynthesis, and catalyses the condensation of acetyl-CoA with acetoacetyl-CoA (AcAc-CoA) to yield S-HMG-CoA. In this study, we have first characterized in detail a
M D Giron et al.
Archives of biochemistry and biophysics, 302(1), 265-271 (1993-04-01)
Using insect (Drosophila) and rodent mammalian cell cultures we demonstrate that acute mevalonate-mediated suppression of 3-hydroxy-3-methylglutaryl coenzyme A was initiated in the absence of protein synthesis. In addition, insect and mammalian cells depleted (1 h) of putative regulatory post-isopentenyl-1-pyrophosphate metabolites
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