V4877

Verrucarin A

from Myrothecium sp., ≥85.0% (HPLC), CCRCC inhibitor

• Synonym(s): Muconomycin A
• Empirical Formula (Hill Notation): C₂₇H₃₄O₉
• CAS Number: 3148-09-2
• Molecular Weight: 502.55
• UNSPSC Code: 12352200
• PubChem Substance ID: 24900750
• NACRES: NA.77
• MDL number: MFCD00056759
• Assay: ≥85.0% (HPLC)
• Quality level: 200

Properties

• Product Name: Verrucarin A from Myrothecium sp., ≥85.0% (HPLC)
• 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[1] is a macrocyclic trichothecene compound.[2]

Application

Verrucarin A from Myrothecium sp has been used:

• as a translation initiation inhibitor in P. falciparum W2 strain[3]
• as a peptidyl transfer inhibitor to test sensitivity in methyltransferase knock-out S. cerevisiae cells[4]
• to test its cytotoxicity in renal cell carcinoma cells[1]

Biochem/physiol Actions

Verrucarin A binds to the P and A sites in ribosomes and blocks peptide-bond and translation initiation.[3] It inhibits the clear cell renal cell carcinoma (CCRCC) proliferation.[1] Verrucarin A blocks the peptidyl transferase activity and favors apoptosis induction in cancer cells[2]

Verrucarin A is phytotoxic to plantlet cultures and cytotoxic to cultured mammalian cell lines.

Other Notes

Macrocyclic trichothecene mycotoxin.

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H300 + H310 + H330
• pcodes: P260 - P262 - P264 - P280 - P302 + P352 + P310 - P304 + P340 + P310
• Hazard Classifications: Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk: WGK 3
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges