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Merck
CN

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

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About This Item

Empirical Formula (Hill Notation):
C22H31NO4
CAS Number:
57749-43-6
Molecular Weight:
373.49
NACRES:
NA.77
UNSPSC Code:
12352200

Key Documents

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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

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

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

Quality Level

200

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.
Equisetin is a tetramic acid analog derived from Fusarium equisti.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
12170506
067M4154V
12170505
089M4117V

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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
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
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

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