V4877

Sigma-Aldrich

Verrucarin A from Myrothecium sp.

≥85.0% (HPLC)

Synonym(s):
Muconomycin A
Empirical Formula (Hill Notation):
C27H34O9
CAS Number:
Molecular Weight:
502.55
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 3462 6.1 / PGI

WGK Germany

WGK 3

Certificate of Analysis
Certificate of Origin
Maria C Dzialo et al.
The Journal of biological chemistry, 289(44), 30511-30524 (2014-09-19)
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...
Ying Wang et al.
Cancer research, 74(5), 1506-1517 (2014-01-07)
Virtually all transcription factors partner with coactivators that recruit chromatin remodeling factors and interact with the basal transcription machinery. Coactivators have been implicated in cancer cell proliferation, invasion, and metastasis, including the p160 steroid receptor coactivator (SRC) family composed of...
Dorrah Deeb et al.
International journal of oncology, 49(3), 1139-1147 (2016-08-31)
Pancreatic ductal adenocarcinoma (PDA) remains one of the most difficult to treat of all malignancies. Multimodality regimens provide only short-term symptomatic improvement with minor impact on survival, underscoring the urgent need for novel therapeutics and treatment strategies for PDA. Trichothecenes...
Chien-Shan Cheng et al.
Cancer cell international, 19, 92-92 (2019-04-24)
In the past decade, increasing research attention investigated the novel therapeutic potential of steroidal cardiac glycosides in cancer treatment. Huachansu and its main active constituent Bufalin have been studied in vitro, in vivo and clinical studies. This review aims to...
Antonio L Amelio et al.
Proceedings of the National Academy of Sciences of the United States of America, 104(51), 20314-20319 (2007-12-14)
Signal transduction pathways often use a transcriptional component to mediate adaptive cellular responses. Coactivator proteins function prominently in these pathways as the conduit to the basic transcriptional machinery. Here we present a high-throughput cell-based screening strategy, termed the "coactivator trap,"...

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