SML1929

Equisetin

(Fusarium equiseti), ≥97% (HPLC)

• Synonym(s): (3E,5S)-3-[[(1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-[(E)-prop-1-enyl]-4a,5,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]-hydroxymethylidene]-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione
• Empirical Formula (Hill Notation): C₂₂H₃₁NO₄
• CAS Number: 57749-43-6
• Molecular Weight: 373.49
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Quality Level: 200
• biological source: (Fusarium equiseti)
• assay: ≥97% (HPLC)
• form: powder
• solubility: DMSO: soluble 1 mg/mL; chloroform: soluble 5 mg/mL
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: C[C@H]1C[C@]2([H])[C@@]([C@](C)(/C(O)=C3C([C@H](CO)N(C)C/3=O)=O)[C@H](/C=C/C)C=C2)([H])CC1
• InChI: 1S/C22H31NO4/c1-5-6-15-9-8-14-11-13(2)7-10-16(14)22(15,3)20(26)18-19(25)17(12-24)23(4)21(18)27/h5-6,8-9,13-17,24,27H,7,10-12H2,1-4H3/b6-5+/t13-,14-,15-,16-,17+,22-/m1/s1
• InChI key: SLOQQJFOWFUUMP-KNQICWOTSA-N

Description

Biochem/physiol Actions

Equisetin is a tetramic acid analog derived from Fusarium equisti. Equisetin is mainly known for its antibiotic and cytotoxic activity and for its inhibitory effect on HIV-1 integrase. Inhibition of HIV integrase by Equisetin was reported with IC₅₀ values of 5-20 μM. Moreover, it was shown that Equisetin specifically inhibits the substrate anion carriers of the inner membrane of mitochondria and acts nonspecifically on protein membranes and protein hydrophobic domains. In addition, it was demonstrated that Equisetin causes phytotoxicity by causing root Necrosis and was also identified in a mycotoxin cocktail associated with cattle feeding problems.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable