11113-62-5

Basic information

• Product Name: ENNIATIN FROM MICROBIAL SOURCE
• Synonyms: ENNIATIN FROM MICROBIAL SOURCE;Enniatin microbial;Enniatin coMplex;(3S,6R,9S,12R,15S,18R)-3,9,15-tri(butan-2-yl)-4,10,16-trimethyl-6,12,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
• CAS NO: 11113-62-5
• Molecular Formula: C36H63N3O9.C35H61N3O9.C34H59N3O9.C33H57N3O9
• Molecular Weight: 2643.46
• Mol File: 11113-62-5.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 827°Cat760mmHg
• Flash Point: 454°C
• Appearance: /
• Density: 1.036g/cm³
• Vapor Pressure: 1.71E-27mmHg at 25°C
• Refractive Index: 1.459
• Storage Temp.: 2-8°C
• Solubility: Soluble in DMSO
• CAS DataBase Reference: ENNIATIN FROM MICROBIAL SOURCE(CAS DataBase Reference)
• NIST Chemistry Reference: ENNIATIN FROM MICROBIAL SOURCE(11113-62-5)
• EPA Substance Registry System: ENNIATIN FROM MICROBIAL SOURCE(11113-62-5)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 22-36/37/39-45
• RIDADR: 2811
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 11113-62-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 11113-62-5 differently. You can refer to the following data:
1. Enniatins are a complex of depsipeptides produced by several Fusarium species. Typically, the complex contains 4 major components: A, A1, B and B1 together with minor amounts of enniatins C, D, E and F. The enniatins act as ionophores. Recently their effects on acyl-CoA cholesterol transferase, as nematocides and the selectivity of their antitumour action have received more focus.
2. Enniatin complex is a complex mixture of Fusarium produced depsipeptide ionophores.This compound can be used to control contamination in fermentation of gaseous substrates.

Biological Activity

enniatins, analogues of beauvericin, is a regular cyclic hexadepsipeptide isolated from fusarium species of fungis, also they have been isolated from other genera, such as verticillium and halosarpheia [1]. they have been involved in many biological activities, such as antiinsectan, antifungal, antibiotic and cytotoxic [1].

in vitro

fusafungine is a mixture of several enniatins with bacteriostatic activity against most micro-organisms responsible for infections and superinfections of the respiratory tract. fusafungine has been developed for treatment of upper respiratory tract infections by oral and/or nasal inhalation. fusafungine in low concentrations down-regulated the expression of intercellular adhesion molecule-1 (icam-1) by activated macrophages, inhibited the production of the proinflammatory cytokines il-1, tnfα and il-6 and inhibited the release of oxygen free radicals by inflammatory macrophages without altering their phagocytic activity. fusafungine also inhibited t-cell activation and proliferation, and the synthesis of ifn-γ by activated t cells [2]. exposure 8 h to enniatins at nanomolar concentrations significantly stimulated cell proliferation. at low micromolar concentrations, enniatins exihibited profound apoptosis-inducing effects against various human cancer cell types. in the fluorescence-activated cell sorting analysis, enniatins induced cell cycle arrest in the g0/g1 phase. in human cancer cells, elevated enn concentrations induced profound p53-dependent cytostatic and p53-independent cytotoxic activities [3]. enniatin easily incorporated into the cell membrane in which it formed cation-selective pores [4].

Purification Methods

It is a cyclic peptidic ester antibiotic which is recrystallised from EtOH/water but is deactivated in alkaline solution. [Ovchinnikov & Ivanov in The Proteins (Neurath and Hill eds) Academic Press, NY, Vol V pp. 365 and 516 1982, Tomeda et al. J Antibiot 45 1626 1992.]

references

[1] sy-cordero a a, pearce c j, oberlies n h. revisiting the enniatins: a review of their isolation, biosynthesis, structure determination and biological activities[j]. the journal of antibiotics, 2012, 65(11): 541-549.[2] german-fattal m. fusafungine, an antimicrobial with anti-inflammatory properties in respiratory tract infections[j]. clinical drug investigation, 2001, 21(9): 653-670.[3] dornetshuber r, heffeter p, kamyar m r, et al. enniatin exerts p53-dependent cytostatic and p53-independent cytotoxic activities against human cancer cells[j]. chemical research in toxicology, 2007, 20(3): 465-473.[4] kamyar m, rawnduzi p, studenik c r, et al. investigation of the electrophysiological properties of enniatins[j]. archives of biochemistry and biophysics, 2004, 429(2): 215-223.

InChI:InChI=1/C33H57N3O9/c1-16(2)22-31(40)43-26(20(9)10)29(38)35(14)24(18(5)6)33(42)45-27(21(11)12)30(39)36(15)23(17(3)4)32(41)44-25(19(7)8)28(37)34(22)13/h16-27H,1-15H3/t22-,23-,24-,25?,26?,27?/m0/s1