| Identification | Back Directory | [Name]
EQUISETIN | [CAS]
57749-43-6 | [Synonyms]
LS-64262
EQUISETIN
(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
2,4-Pyrrolidinedione, 5-(hydroxymethyl)-3-[hydroxy[(1S,2R,4aS,6R,8aR)-1,2,4a,5,6,7,8,8a-octahydro-1,6-dimethyl-2-(1E)-1-propen-1-yl-1-naphthalenyl]methylene]-1-methyl-, (3E,5S)- | [Molecular Formula]
C22H31NO4 | [MDL Number]
MFCD01729357 | [MOL File]
57749-43-6.mol | [Molecular Weight]
373.49 |
| Chemical Properties | Back Directory | [Melting point ]
117-118 °C | [Boiling point ]
556.0±50.0 °C(Predicted) | [density ]
1.180±0.06 g/cm3(Predicted) | [storage temp. ]
Hygroscopic, -20°C Freezer, Under inert atmosphere | [solubility ]
Acetone (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
4.50±1.00(Predicted) | [color ]
Pale Beige to Light Brown | [Stability:]
Hygroscopic |
| Safety Data | Back Directory | [HS Code ]
29339900 | [Toxicity]
mouse,LD50,intraperitoneal,63mg/kg (63mg/kg),Antimicrobial Agents and Chemotherapy. Vol. 5, Pg. 634, 1974. |
| Hazard Information | Back Directory | [Description]
Equisetin is a fungal metabolite that has been isolated from Fusarium. It inhibits HIV-1 integrase 3’ end-processing and strand transfer activities. Equisetin inhibits the ATPase activity of rat liver mitochondria and mitoplasts stimulated by 2,4-dinitrophenol (Dnp) in a concentration-dependent manner (IC50 = ~8 nM per mg of protein for both). It also inhibits ADP-stimulated respiration and the mitochondrial transport of ATP, inorganic phosphate, and succinate. Epiequisetin is phytotoxic and inhibits the germination of various seeds and growth of young seedlings. | [Uses]
The tetramic acid, equisetin, is produced by a number of species of Fusarium. Interest in equisetin emerged with reports of its inhibitory activity against HIV-1 integrase in vitro that was mechanistically distinct from previously described inhibitors. Equisetin inhibits 3' end-processing and strand transfer, as well as disintegration catalysed by either the full-length enzyme or the truncated integrase core. | [in vivo]
Equisetin (20-80 mg/kg, i.g., 6 weeks) inhibits obesity and increased energy expenditure in high-fat diet-induced obese mice through inhibition of the enzymatic activity of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1)[5].
Equisetin (10 mg/kg, i.p., 6 h) shows significant anti-infective activity in a mouse model of Staphylococcus aureus ATCC 29213 infection[8].
Equisetin (5-20 mg/kg, p.o., every two days until 12 weeks) prevents atherosclerosis in mice by binding to and inhibiting the activity of STAT3[10].
| Animal Model: | Atherosclerosis model (eight-week-old male ApoE-/- mice were fed with HFD for 12 weeks)[10] | | Dosage: | 5, 20 mg/kg | | Administration: | Oral gavage (p.o.), every two days until 12 weeks | | Result: | Attenuated HFD-induced lipid area in the en face prepared aorta and aortic root.
Attenuated atherosclerotic lesion area (HFD versus HFD+5?mg/kg Equisetin: 31.71 versus 16.95; HFD versus HFD+20?mg/kg Equisetin: 31.71 versus 10.12).
Increased collagen content in the aortic plaques.
Increased α-SMA-positive areas in the plaques in aortic root.
|
| [IC 50]
STAT3 | [storage]
Store at -20°C | [References]
[1] A.E. DESJARDINS R. H P. Molecular biology of Fusarium mycotoxins[J]. International journal of food microbiology, 2007, 119 1: Pages 47-50. DOI: 10.1016/j.ijfoodmicro.2007.07.024
[2] BHARGAVI PATHAM. Post-translational import of protein into the endoplasmic reticulum of a trypanosome: an in vitro system for discovery of anti-trypanosomal chemical entities.[J]. Biochemical Journal, 2009, 419 2: 507-517. DOI: 10.1042/bj20081787
[3] SHEO B. SINGH ? . Equisetin and a novel opposite stereochemical homolog phomasetin, two fungal metabolites as inhibitors of HIV-1 integrase[J]. Tetrahedron Letters, 1998, 39 16: Pages 2243-2246. DOI: 10.1016/s0040-4039(98)00269-x
[4] T K?NIG B S A Kapus. Effects of equisetin on rat liver mitochondria: evidence for inhibition of substrate anion carriers of the inner membrane.[J]. Journal of Bioenergetics and Biomembranes, 1993, 25 5: 537-545. DOI: 10.1007/bf01108410
[5] M.H. WHEELER L. S P R D Stipanovic. Phytotoxicity of equisetin and epi-equisetin isolated from Fusarium equiseti and F. pallidoroseum[J]. Mycological research, 1999, 103 8: Pages 967-973. DOI: 10.1017/s0953756298008119 |
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