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Equisetin

Names

[ CAS No. ]:
57749-43-6

[ Name ]:
Equisetin

[Synonym ]:
Equisetin

Biological Activity

[Description]:

Equisetin is an N-methylserine-derived acyl tetramic acid isolated from a terrestrial fungus Fusarium equiseti NRRL 5537[1]. Equisetin is a tetramate-containing natural product with antibiotic and cytotoxic activity[2]. Equisetin inhibits the growth of Gram-positive bacteria and HIV-1 integrase activity but shows no activity against Gram-negative bacteria[3]. Equisetin is a Quorum-sensing inhibitor (QSI) that attenuates QS-regulated virulence phenotypes in P. aeruginosa without affecting the growth of bacterias, serves as a leading compound for the treatment of P. aeruginosa infections[4].

[Related Catalog]:

Research Areas >> Infection
Signaling Pathways >> Metabolic Enzyme/Protease >> HIV Integrase

[References]

[1]. Burmeister HR, et al. Antibiotic produced by Fusarium equiseti NRRL 5537. Antimicrob Agents Chemother. 1974 Jun;5(6):634-9.

[2]. Vesonder RF, et al. Equisetin, an antibiotic from Fusarium equiseti NRRL 5537, identified as a derivative of N-methyl-2, 4-pyrollidone. J Antibiot (Tokyo). 1979 Jul;32(7):759-61.

[3]. Lee J, et al. The hierarchy quorum sensing network in Pseudomonas aeruginosa. Protein Cell. 2015 Jan;6(1):26-41.

[4]. Zhang M, et al. Equisetin as potential quorum sensing inhibitor of Pseudomonas aeruginosa. Biotechnol Lett. 2018 May;40(5):865-870.

Chemical & Physical Properties

[ Density]:
1.187 g/cm3

[ Boiling Point ]:
513.6ºC at 760 mmHg

[ Molecular Formula ]:
C22H31NO4

[ Molecular Weight ]:
373.48600

[ Flash Point ]:
264.4ºC

[ Exact Mass ]:
373.22500

[ PSA ]:
77.84000

[ LogP ]:
2.95920

[ Index of Refraction ]:
1.587

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
KD7986000
CHEMICAL NAME :
Equisetin
CAS REGISTRY NUMBER :
57749-43-6
LAST UPDATED :
199403
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C22-H31-N-O4
MOLECULAR WEIGHT :
373.54

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
63 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AMACCQ Antimicrobial Agents and Chemotherapy. (American Soc. for Microbiology, 1913 I St., NW, Washington, DC 20006) V.1- 1972- Volume(issue)/page/year: 5,634,1974

Synthetic Route

Precursor & DownStream