Cerulenin ≥98% (HPLC), from Cephalosporium caerulens ยี่ห้อ Sigma

PROPERTIES

biological source

Cephalosporium caerulens

Quality Level

200

Assay

≥98% (HPLC)

form

powder

mp

93 °C

solubility

acetone: 19.60-20.40 mg/mL, clear to slightly hazy, colorless to yellow

antibiotic activity spectrum

fungi

Mode of action

enzyme | inhibits

storage temp.

−20°C

SMILES string

C/C=C/C/C=C/CCC([C@@H]1[C@H](C(N)=O)O1)=O

InChI

1S/C13H18O3/c1-3-4-5-6-7-8-9-11(15)13-12(16-13)10(2)14/h3-4,6-7,12-13H,5,8-9H2,1-2H3/b4-3+,7-6+/t12-,13+/m0/s1

InChI key

PTNNGEBMCNMENY-JIVMHGEESA-N

Gene Information

human ... FASN(2194)

DESCRIPTION

General description

Chemical structure: fatty acid derivative

Application

Cerulenin has been used:

as a fatty acid synthase inhibitor to study its effects on aldosterone-induced trained immunity[1]

as a blocker of fatty acid synthase to study its effects on the replication of severe acute respiratory syndrome coronavirus 2 (SARS-CoV2)[2]

as a supplement in yeast extract–peptone–dextrose/glycerol (YPD/G) agar plates for the isolation of cerulenin-resistant yeast strains[3]

Biochem/physiol Actions

Cerulenin is a fungal metabolite[4], that is involved in the inhibition of fatty acid synthase by alkylating β-ketoacyl acyl-carrier-protein synthase[5] in several prokaryotic and eukaryotic cells.[6] It also inhibits polyketide synthases and exhibits anti-candida activity. Cerulenin acts as a phytotoxic virulence factor and also blocks the activity of other fungal pathogens in Sarocladium oryzae.[7] It also acts as an effective inducer of apoptosis and cytotoxic effects in tumor cells whereas normal human keratinocytes and fibroblasts resist the effects of cerulenin. Cerulenin plays a role in in vitro inhibition of HIV-1 proteinase.[4]