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V4877 Sigma-Aldrich

Verrucarin A from Myrothecium sp.

≥85.0% (HPLC)

Synonym: Muconomycin A

  • CAS Number 3148-09-2

  • Empirical Formula (Hill Notation) C27H34O9

  • Molecular Weight 502.55

  •  MDL number MFCD00056759

  •  PubChem Substance ID 24900750

  •  NACRES NA.77

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, Mold,
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

Description

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.

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
RIDADR 
UN 3462 6.1 / PGI
WGK Germany 
WGK 3
RTECS 
WH1314900

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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