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V4877

Sigma-Aldrich

Verrucarin A from Myrothecium sp.

≥85.0% (HPLC)

Synonym(s):

Muconomycin A

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About This Item

Empirical Formula (Hill Notation):
C27H34O9
CAS Number:
3148-09-2
Molecular Weight:
502.55
MDL number:
MFCD00056759
UNSPSC Code:
12352200
PubChem Substance ID:
24900750
NACRES:
NA.77

Quality Level

200

Assay

≥85.0% (HPLC)

storage temp.

−20°C

SMILES string

CC1CCOC(=O)\C=C\C=C\C(=O)OC2CC3OC4C=C(C)CCC4(COC(=O)C1O)C2(C)C35CO5

InChI

1S/C27H34O9/c1-16-8-10-26-14-33-24(31)23(30)17(2)9-11-32-21(28)6-4-5-7-22(29)36-18-13-20(35-19(26)12-16)27(15-34-27)25(18,26)3/h4-7,12,17-20,23,30H,8-11,13-15H2,1-3H3/b6-4+,7-5+

InChI key

NLUGUZJQJYVUHS-YDFGWWAZSA-N

General description

Verrucarin derived from the Myrothecium verrucari, a fungal plant pathogen is a macrocyclic trichothecene compound.

Application

Verrucarin A from Myrothecium sp has been used:
  • as a translation initiation inhibitor in P. falciparum W2 strain
  • as a peptidyl transfer inhibitor to test sensitivity in methyltransferase knock-out S. cerevisiae cells
  • to test its cytotoxicity in renal cell carcinoma cells

Biochem/physiol Actions

Verrucarin A binds to the P and A sites in ribosomes and blocks peptide-bond and translation initiation. It inhibits the clear cell renal cell carcinoma (CCRCC) proliferation. Verrucarin A blocks the peptidyl transferase activity and favors apoptosis induction in cancer cells
Verrucarin A is phytotoxic to plantlet cultures and cytotoxic to cultured mammalian cell lines.

Other Notes

Macrocyclic trichothecene mycotoxin.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H310 + H330

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Proceedings of the National Academy of Sciences of the United States of America, 104(51), 20314-20319 (2007-12-14)
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Methylation of various components of the translational machinery has been shown to globally affect protein synthesis. Little is currently known about the role of lysine methylation on elongation factors. Here we show that in Saccharomyces cerevisiae, the product of the
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Neoplasia (New York, N.Y.), 14(8), 771-777 (2012-09-07)
Verrucarin A (VA) is a small molecule derived from the fungal plant pathogen Myrothecium verrucaria and was identified as a selective inhibitor of clear cell renal cell carcinoma (CCRCC) cell proliferation in a high-throughput screen of a library of naturally
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