57749-43-6

Basic information

• Product Name: EQUISETIN
• Synonyms: EQUISETIN
• CAS NO: 57749-43-6
• Molecular Formula: C22H31NO4
• Molecular Weight: 373.49
• Mol File: 57749-43-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 117-118 °C
• Boiling Point: 513.6 °C at 760 mmHg
• Flash Point: 264.4 °C
• Appearance: /
• Density: 1.187 g/cm³
• Vapor Pressure: 1.07E-12mmHg at 25°C
• Refractive Index: 1.587
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Acetone (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 4.50±1.00(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: EQUISETIN(CAS DataBase Reference)
• NIST Chemistry Reference: EQUISETIN(57749-43-6)
• EPA Substance Registry System: EQUISETIN(57749-43-6)

Safety Data

• Hazardous Substances Data: 57749-43-6(Hazardous Substances Data)

Usage

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

Different sources of media describe the Uses of 57749-43-6 differently. You can refer to the following data:
1. 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.
2. Equisetin is tetramic acid with antibiotic and cytotoxic activity, and a potent inhibitor of HIV-1 integrase.

InChI:InChI=1/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

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Downstream Products

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Relevant articles and documents

Chemo-enzymatic synthesis of equisetin

We here report that the biosynthesis of equisetin, a fungal tetramate natural product with potent anti-infectious activity, relies on Fsa2, a Diels-Alderase that constructs the trans-decalin system of the molecule in a stereo-selective manner. This finding led to the development of a concise chemo-enzymatic route toward the synthesis of equisetin, which involves facile preparation of a linear polyene precursor via 7-steps and Fsa2 activity for equisetin maturation through an intramolecular Diels-Alder reaction, thus exemplifying the significance of the combination of chemical and biological methods to achieve structurally complex cyclic natural products and their derivatives.

Biomimetic synthesis of equisetin and (+)-fusarisetin A

(+)-FusarisetinA belongs to a group of acyl tetramic acid natural products that show potential anticancer activity. Equisetin, a biogenetically related acyl tetramic acid, contains the basic skeleton of (+)-fusarisetinA. We proposed that equisetin and (+)-fusarisetinA share a biosynthetic pathway that starts with naturally occurring (S)-serine and an unsaturated fatty acid. In support of this hypothesis, we have demonstrated that a cyclization sequence involving an intramolecular Diels-Alder reaction followed by a Dieckmann cyclization of polyenoylamino acid yielded equisetin. The aerobic oxidation of equisetin, promoted by either MnIII/O2 or a reactive oxygen species (ROS) produced by visible-light chemistry, gave peroxyfusarisetin, which could be easily reduced to (+)-fusarisetinA. We report herein detailed information on the biogenetic synthesis of equisetin and (+)-fusarisetinA. Make the change to bio! Biomimetic synthesis of equisetin and (+)-fusarisetinA was achieved based on a biosynthetic hypothesis. An intramolecular Diels-Alder reaction followed by a Dieckmann cyclization of polyenoylamino ester furnished equisetin. The aerobic oxidation of equisetin to give (+)-fusarisetinA was mediated by a MnIII/O2 system or reactive oxygen species (ROS) (see scheme). Copyright