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Key Documents

SML1929

Sigma-Aldrich

Equisetin

(Fusarium equiseti), ≥97% (HPLC)

Synonyme(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

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About This Item

Formule empirique (notation de Hill):
C22H31NO4
Numéro CAS:
Poids moléculaire :
373.49
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Niveau de qualité

Source biologique

(Fusarium equiseti)

Pureté

≥97% (HPLC)

Forme

powder

Solubilité

DMSO: soluble 1 mg/mL
chloroform: soluble 5 mg/mL

Conditions d'expédition

ambient

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

SLOQQJFOWFUUMP-KNQICWOTSA-N

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


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Consulter la Bibliothèque de documents

D Hazuda et al.
Antiviral chemistry & chemotherapy, 10(2), 63-70 (1999-05-21)
We have identified a series of novel inhibitors of human immunodeficiency virus type 1 (HIV-1) integrase by randomly screening natural product extracts using an in vitro biochemical assay designed to identify inhibitors of integrase-catalysed strand transfer. Equisetin recovered from the
T König et al.
Journal of bioenergetics and biomembranes, 25(5), 537-545 (1993-10-01)
The effect of equisetin, an antibiotic produced by Fusarium equiseti, has been studied on mitochondrial functions (respiration, ATPase, ion transport). Equisetin inhibits the DNP-stimulated ATPase activity of rat liver mitochondria and mitoplasts in a concentration-dependent manner; 50% inhibition is caused
Agha W Yunus et al.
Toxins, 7(6), 2188-2197 (2015-06-16)
Cottonseed cake in South East Asia has been associated with health issues in ruminants in the recent years. The present study was carried out to investigate the health issues associated with cottonseed cake feeding in dairy animals in Pakistan. All

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