Equisetin

Modify Date: 2024-01-03 15:04:33

Equisetin structure	Common Name	Equisetin
	CAS Number	57749-43-6	Molecular Weight	373.48600
	Density	1.187 g/cm3	Boiling Point	513.6ºC at 760 mmHg
	Molecular Formula	C₂₂H₃₁NO₄	Melting Point	N/A
	MSDS	N/A	Flash Point	264.4ºC

Use of Equisetin

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].

Name	(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
Synonym	More Synonyms

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.

Description

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.

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

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

Precursor 9
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CAS#:5524-05-0 (+)-dihydrocarvone CAS#:38339-60-5 (1S,8Ξ)-2-oxo-t... CAS#:122902-65-2 (2R,4aR,5S,6R,8... CAS#:122902-57-2 (1S,4aR,7R,8aR)...
CAS#:122902-61-8 (1S,2R,4aS,6R,8...
DownStream 0