EQUISETIN
EQUISETIN Basic information
- Product Name:
- EQUISETIN
- Synonyms:
-
- EQUISETIN
- LS-64262
- 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)-
- (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
- Citalopram Impurity 39
- (3E,5S)-3-{[(1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-[(1E)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl](hydroxy)methylidene}-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione
- CAS:
- 57749-43-6
- MF:
- C22H31NO4
- MW:
- 373.49
- Mol File:
- 57749-43-6.mol
EQUISETIN Chemical Properties
- 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
EQUISETIN Usage And Synthesis
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.
Uses
Equisetin is tetramic acid with antibiotic and cytotoxic activity, and a potent inhibitor of HIV-1 integrase.
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
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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