An efficient one-pot synthesis of anthraquinone derivatives catalyzed by alum in aqueous media

Madje, Balaji R.; Shelke, Kiran F.; Sapkal, Suryakant B.; Kakade, Gopal K.; Shingare, Murlidhar S.

doi:10.1080/17518251003776877

Cited by 24 publications

(14 citation statements)

References 29 publications

(6 reference statements)

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“…Recently, the synthesis of anthraquinone derivatives has attracted significant interest. Various synthesis methods have been reported, the most common of which is the intramolecular condensation of aryl and O -arylbenzoic acids, using fuming sulfuric acid, benzoyl chloride, concentrated sulfuric acid, benzoyl chloride, zinc chloride, and POCl 3 /P 2 O 3 C l4 as catalyst, which produces anthraquinone derivatives [ 18 ]. Anthraquinone and its associated derivatives were previously synthesized by a chemical pathway, although this method was expensive and involved several hurdles [ 19 ].…”

Section: Introductionmentioning

confidence: 99%

Microbial Synthesis of Non-Natural Anthraquinone Glucosides Displaying Superior Antiproliferative Properties

et al. 2018

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Anthraquinones, naturally occurring bioactive compounds, have been reported to exhibit various biological activities, including anti-inflammatory, antiviral, antimicrobial, and anticancer effects. In this study, we biotransformed three selected anthraquinones into their novel O-glucoside derivatives, expressing a versatile glycosyltransferase (YjiC) from Bacillus licheniformis DSM 13 in Escherichia coli. Anthraflavic acid, alizarin, and 2-amino-3-hydroxyanthraquinone were exogenously fed to recombinant E. coli as substrate for biotransformation. The products anthraflavic acid-O-glucoside, alizarin 2-O-β-d-glucoside, and 2-amino-3-O-glucosyl anthraquinone produced in the culture broths were characterized by various chromatographic and spectroscopic analyses. The comparative anti-proliferative assay against various cancer cells (gastric cancer-AGS, uterine cervical cancer-HeLa, and liver cancer-HepG2) were remarkable, since the synthesized glucoside compounds showed more than 60% of cell growth inhibition at concentrations ranging from ~50 μM to 100 μM. Importantly, one of the synthesized glucoside derivatives, alizarin 2-O-glucoside inhibited more than 90% of cell growth in all the cancer cell lines tested.

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Section: Introductionmentioning

confidence: 99%

Microbial Synthesis of Non-Natural Anthraquinone Glucosides Displaying Superior Antiproliferative Properties

et al. 2018

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“…Anthraquinones are a group of naturally occurring important compounds that can also be obtained synthetically (Madje et al 2010;Puenner et al 2013;Seidel et al 2013;Xu et al 2010). The economic significance of anthraquinones such as in manufacture of dyes and pigments have caused advanced studies to be conducted, which focused on optical spectroscopy and photochemistry properties of the compound (Gordon & Gregory 1983).…”

Section: Introductionmentioning

confidence: 99%

Isolation and Photophysical Properties of Di- and Tri-substituted Natural Anthraquinones from Malaysian Morinda citrifolia

Adnan¹,

Nasuha²,

Abdullah³

et al. 2018

JSM

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Five di-and tri-substituted natural anthraquinones, i.e. nordamnacanthal (1), damnacanthal (2), rubiadin (3), 1-methoxy-2-methyl-3-hydroxyanthraquinone (4) and 1-hydroxy-3-methoxyanthraquinone (5) were subjected to photophysical studies. The results indicated that steric hindrance and intramolecular hydrogen bonding are important factors that affect absorption and emission spectral of these natural anthraquinones. Besides that, emission properties were significantly enhanced with formation of intramolecular hydrogen bonding in 1,3-dihydroxy-2-aldehyde tri-substituted anthraquinone 1. This gave rise to formation of two additional quasi aromatic rings extending the π-conjugation system in the anthraquinone structure.

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“…[1][2][3]. Anthraquinone structural motif is present in many natural dyes, pigments, vitamins, enzymes etc [4]. Among 700 natural anthraquinones identified, about 200 compounds were isolated from plants and remaining from lichens, fungi and others [5][6].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of antioxidative anthraquinones as potential anticancer agents

et al. 2021

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Antioxidant and antibacterial activities of natural anthraquinones namely chrysophanol (1) and emodin (2), and synthesized anthraquinones viz. 2-methylanthraquinone (3), anthraquinone (4), 2-bromoanthraquinone (5), rubiadin (6), chrysophanol diacetate (7), rubiadin diacetate (8) and 1,8-dimethoxy-3-methylanthraquinone (9) were investigated. Anthraquinones 9, 3, 6, 5 and 2 exhibited a high DPPH• radical scavenging capacity (IC50 = <500 μg/mL) showing their therapeutic potentiality for the treatment of cancers. These anthraquinones 1-9 have also displayed a weak to moderate antibacterial activity against Bacillus subtilis. Chrysophanol diacetate (7) including emodin (2) have been appeared as the valuable antibacterials. BIBECHANA 18 (2) (2021) 143-153

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An efficient one-pot synthesis of anthraquinone derivatives catalyzed by alum in aqueous media

Cited by 24 publications

References 29 publications

Microbial Synthesis of Non-Natural Anthraquinone Glucosides Displaying Superior Antiproliferative Properties

Microbial Synthesis of Non-Natural Anthraquinone Glucosides Displaying Superior Antiproliferative Properties

Isolation and Photophysical Properties of Di- and Tri-substituted Natural Anthraquinones from Malaysian Morinda citrifolia

Synthesis of antioxidative anthraquinones as potential anticancer agents

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