28714-26-3

Usage

Uses

Used in Pharmaceutical Industry:
(+)-Aerothionin is used as an antimycobacterial agent for its ability to target and combat mycobacterial infections, such as tuberculosis. Its unique bromine-containing structure contributes to its effectiveness in treating drug-resistant strains of mycobacteria.
Used in Research and Development:
(+)-Aerothionin serves as a valuable compound in the field of research and development, particularly in the study of bromine-containing alkaloids and their potential applications in medicine. Its complex structure and antimycobacterial properties make it an interesting subject for further investigation and potential development of new drugs and therapies.

Biological Activity

aerothionin is derived from marine sponges with an antimycobacterial activity.antimycobacterial drugs are used in the treatment of diseases caused by mycobacterium genus, such as tuberculosis and leprosy.

in vitro

in a continuation of efforts to identify bioactive compounds from red sea verongid sponges, the organic extract of the sponge suberea species afforded seven compounds including aerothionin, together with two new dibrominated alkaloids and four known compounds. in-vitro cytotoxicity study showed that aerothionin and subereaphenol c had potent cytotoxic activity against hela cell line with ic50 values of 29 and 13.3 μm, respectively. [1].

in vivo

red sea suberea mollis sponge extract (smse), which contains aerothionin, was evaluated for its protective effect on carbon tetrachloride- (ccl4-) induced acute liver injury in rats. rats were orally administered three different concentrations of smse along with ccl4 for 14 days. smse could significantly reduce liver enzyme activities and hepatic mda formation. in addition, smse was able to restore no, sod, gsh, gpx, and cat. the histopathological results further confirmed these in-vivo findings [2].

IC 50

29 μm for hela cells proliferation

references

[1] shaala, l. a.,youssef, d.t.a.,badr, j.m., et al. bioactive secondary metabolites from the read sea marine verongid sponge suberea species. mar.drugs 13, 1621-1631 (2015).[2] abbas at, el-shitany na, shaala la, ali ss, azhar ei, abdel-dayem ua, youssef dt. red sea suberea mollis sponge extract protects against ccl4-induced acute liver injury in rats via an antioxidant mechanism. evid based complement alternat med. 2014;2014:745606.

Upstream product

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• 28687-76-5 N,N'-bis<3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-2-hydroxyiminopropionyl>-1,4-butanediamine 
• 87580-09-4 (5S*,6R*)-methyl 7,9-dibromo-8-methoxy-6-oxo-1-oxa-2-azaspiro<4.5>deca-2,7,9-triene-3-carboxylate 
• 110-60-1 1,4-diaminobutane 
• 87580-07-2 methyl 2-hydroxyimino-3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)propionate 
• 87580-08-3 methyl 7,9-dibromo-8-methoxy-6-oxo-1-oxa-2-azaspiro<4.5>deca-2,7,9-triene-3-carboxylate 
• 35353-87-8 methyl (3,5-dibromo-2-hydroxy-4-methoxyphenyl)acetate 
• 28687-76-5 3-(3,5-Dibromo-2-hydroxy-4-methoxy-phenyl)-N-(4-{3-(3,5-dibromo-2-hydroxy-4-methoxy-phenyl)-2-[(E)-hydroxyimino]-propionylamino}-butyl)-2-[(E)-hydroxyimino]-propionamide 
• 212688-07-8 methyl (2-hydroxy-4-methoxyphenyl)acetate 
• 209404-16-0 methyl (2-benzyloxy-4-methoxyphenyl)acetate 
• 212688-09-0 3,5-dibromo-2-(p-methoxybenzyloxy)-4-methoxyphenylacetic acid 
• 212688-08-9 methyl [3,5-dibromo-2-(p-methoxybenzyloxy)-4-methoxyphenyl]acetate 
• 212688-10-3 4-[3,5-Dibromo-4-methoxy-2-(4-methoxy-benzyloxy)-phenyl]-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-butyronitrile 
• 212688-12-5 3-[3,5-Dibromo-4-methoxy-2-(4-methoxy-benzyloxy)-phenyl]-N-(4-{3-[3,5-dibromo-4-methoxy-2-(4-methoxy-benzyloxy)-phenyl]-2-oxo-propionylamino}-butyl)-2-oxo-propionamide 

Relevant academic research and scientific papers

Synthesis and structural revision of calafianin, a member of the spiroisoxazole family isolated from the marine sponge, Aplysina gerardogreeni

Calafianin 1 was successfully synthesized by employing a spiroisoxazoline compound, which was produced by electrochemical oxidation of the oximino-phenol derivative 7 followed by reduction. This investigation revealed a structural revision of 1, the trans

Asymmetric synthesis of aerothionin, a marine dimeric spiroisoxazoline natural product, employing optically active spiroisoxazoline derivative

Successful first synthesis of optically pure (+)- and (-)-aerothionins (1) from the racemic spiroisoxazoline derivative 8 has been accomplished. The absolute configuration of natural (+)-1 was determined by comparison of (+)- and (-)-8 with related deriva

Total synthesis, structural revision, and biological evaluation of calafianin, a marine spiroisoxazoline from the sponge, Aplysina gerardogreeni

The reported structure of the natural calafianin (1) and its isomer in the epoxide region 13 were successfully synthesized through the cis- and trans-spiroisoxazoline compounds, which were produced by electrochemical oxidation of the hydroxyimino-phenol d

Syntheses of the marine metabolites verongamine, hemibastadin-2, and aerothionin using the cyano ylide coupling methodology

Syntheses of the marine metabolites verongamine, hemibastadin-2, and aerothionin have been accomplished by a methodology involving the conversion of a carboxylic acid to an acyl cyano phosphorane which may be oxidized to an α,β-diketo nitrile. This strong

Asymmetric Oxidative Cyclization of o-Phenolic Oxime-Esters: First Synthesis of Enantiomerically Enriched Spiroisoxazoline Methyl Esters

A new method for the synthesis of enantiomerically enriched cyclohexadienone spiroisoxazoline (-)-2a has been described. Asymmetric intramolecular oxidative cyclization of the o-phenolic oximeester 1c using a novel optically active tertiary alcohol (-)-3 as a chiral auxiliary proceeded smoothly to afford cyclohexadienone spiroisoxazoline 2c in 83% yield. Opitcally active tertiary alcohol (-)-3 was synthesizied from racemic (1S*,8R*,9R*,10R*)-8-phenyl-1-decalol (4) by optical resolution. Removal of the chiral auxiliary in 2c with CF3COOH followed by methylation gave methyl ester (-)-2a in 74% ee (71% chemical yield) having S-configuration. The absolute configuration of 2a was determined by the synthesis of the marine natural product (+)-aerothionin.

Total syntheses of (±)-aerothionin, (±)-homoaerothionin, and (±)-aerophobin-1

(±)-Aerothionin, (±)-homoaerothionin, and (±)-aerophobin-1 have been successfully synthesized using phenolic oxidation of the methyl pyruvate oxime derivative with thallium(III) trifluoroacetate as a key step. The stereostructure of aerophobin-2 has been also established by comparison of the 1H NMR spectrum with those of related compounds.

TOTAL SYNTHESES OF (+/-)-AEROTHIONIN AND (+/-)-HOMOAEROTHIONIN

Both aerothionin and homoaerothionin, the novel metabolites of the sponges Aplysina aerophoba, A. fistularis and Verongia thiona, have been synthesized in racemic form.