Anti-proliferative and Antioxidant Activities of 1-methoxy-3-methyl-8-hydroxy-anthraquinone, a Hydroxyanthraquinoid Extrolite Produced by Amycolatopsis thermoflava strain SFMA-103

Kumar, C. Ganesh; Mongolla, Poornima; Chandrasekhar, Cheemalamarri; Poornachandra, Y.; Siva, Bandi; Babu, K. Suresh; Ramakrishna, Kallaganti V. S.

doi:10.4014/mbl.1705.05001

Cited by 9 publications

(12 citation statements)

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“…Based on its chromatographic properties, proton and carbon spectra, and available reported data, the compound could be identified as 1-methoxy-3-methyl-8-hydroxy-anthraquinone (Fig. 2 ) (Kumar et al 2017 ).…”

Section: Resultsmentioning

confidence: 99%

Bioactive secondary metabolites from marine Actinomyces sp. AW6 with an evaluation of ADME-related physicochemical properties

et al. 2022

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This study was designed to evaluate the antimicrobial, antioxidant, and cytotoxic potentials of the marine actinomycetes spp. isolated from the Red Sea water, Hurghada, Egypt. Out of 80 actinomycetes isolates, one isolate AW6 was selected based on its antioxidant activity (IC50 about 5.24 µg/mL which scavenged 91% of formed DPPH free radicals) and antimicrobial potential against E. coli, S. aureus, B. subtilis, and P. aeruginosa, A. niger, and C. albicans. The strain was identified based on phenotypic and genotypic analysis, and deposited in the GenBank with accession number OK090864.1. Cultivation of the selected strain on rice, chromatographic purification, and structural elucidation led to the isolation of two compounds C1: umbelliferone, and C2: 1-methoxy-3-methyl-8-hydroxy-anthraquinone. The antimicrobial activity of the obtained compounds showed that C1 and C2 have low antibacterial activity toward S. aureus and E. coli with no pronounced activity toward P. aeruginosa, C. albicans, and A. niger. Additionally, the antioxidant activity of C1 and C2 revealed that C2 has a good antioxidant activity, with DPPH scavenging activity reaching (55.25%), followed by C1 (30.20%). Moreover, both compounds displayed anti-Gyr-B enzyme activity with IC50 value of (3.79 ± 0.21 µM) for C1, and (IC50 = 13 ± 0.71 µM) for C2. The ADME-related physicochemical properties of the obtained compound were predicted using SwissADME web tools and the ProToxii webserver was used to estimate in silico toxicity.

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Section: Resultsmentioning

confidence: 99%

Bioactive secondary metabolites from marine Actinomyces sp. AW6 with an evaluation of ADME-related physicochemical properties

et al. 2022

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“…Owing to the significant XO inhibition potential of the Amycolatopsis thermoflava ICTA 103culture filtrate, further studies were performed for isolation and purification of metabolite from the culture filtrate of the strain. The procedure for isolation and purification was described elsewhere [17] . Briefly, the culture supernatant was treated with resin to adsorb the compound followed by resin washing and drying.…”

Section: Isolation and Purification Of Omc From Amycolatopsis Thermof...mentioning

confidence: 99%

Inhibition of Xanthine oxidase by 1-O-methyl chrysophanol, a hydroxyanthraquinone isolated fromAmycolatopsis thermoflavaICTA 103

Batchu¹,

Reddi

Surapaneni³

et al. 2023

Preprint

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Hyperuricemia caused by elevated levels of serum uric acid is responsible for implication of gout and other associated disorders that influence the human health. So far, Xanthine oxidase (XO) inhibitors are the choice of first line drugs for the treatment of hyperuricemia. The objective of the present study was to isolate a potent XO inhibitor from the actinobacteria and to evaluate its inhibitory mechanism. Initially, XO was isolated from bovine milk using standard protocol and enzyme kinetics were evaluated. Thereafter, culture filtrates of actinobacteria (Amycolatopsis thermoflavaICTA 103),Streptomyces luteireticuliICTA 16,Streptomyces kurssanoviiICTA165 andAmycolatopsis luridaICTA 194) were screened for XO inhibition usingin vitroqualitative NBT plate assay followed by extraction and purification of potent inhibitor 1-O-methyl chrysophanol (OMC), from the culture filtrate ofAmycolatopsis thermoflavaICTA 103, which belongs to hydroxy anthraquinones (HAQ) family. Further,in silicomolecular model building was performed to study the binding affinity of OMC towards XO followed by quantitativein vitrospectroscopic assays. The molecular building study explored the mechanistic view of binding interaction between inhibitor & enzyme and the results were corroborates with thein vitrokinetic study. Thein vitroresults revealed the significant enzyme inhibition potential of OMC with an IC50andKivalue of 24.8 ± 0.072 µM & 2.218 ± 0.3068 µM respectively. These results are comparable to standard allopurinol, however, more significant than its structural analog, chrysophanol. The kinetic analysis revealed that OMC is a reversible slow binding inhibitor and the Lineweaver - Burkplot analysis showed mixed type inhibition of OMC against XO. These results are in agreement with chrysophanol. Findings of this study proposed a new derivative of HAQ in the pipeline of hyperuricemia therapeutic drug candidates.

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“…Compound 19 displayed infusive anti-cancer activity in-vitro to resist lymphoblastic leukemia as well as lung cancer cells, with the IC 50 values of 16.98 and 10.3 µM, separately. In addition, the DPPH assay showed that this compound had favorable capacity to scavenge free radicals with the EC 50 value of 18.2 µg/mL [ 16 ]. Furthermore, compound 19 suppressed α-glucosidase and α-amylase with IC 50 values of 10.32 and 0.91 µM, respectively.…”

Section: Secondary Metabolites From the Genus Amycolatopmentioning

confidence: 99%

Secondary Metabolites of the Genus Amycolatopsis: Structures, Bioactivities and Biosynthesis

Song

Wang

et al. 2021

Molecules

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Actinomycetes are regarded as important sources for the generation of various bioactive secondary metabolites with rich chemical and bioactive diversities. Amycolatopsis falls under the rare actinomycete genus with the potential to produce antibiotics. In this review, all literatures were searched in the Web of Science, Google Scholar and PubMed up to March 2021. The keywords used in the search strategy were “Amycolatopsis”, “secondary metabolite”, “new or novel compound”, “bioactivity”, “biosynthetic pathway” and “derivatives”. The objective in this review is to summarize the chemical structures and biological activities of secondary metabolites from the genus Amycolatopsis. A total of 159 compounds derived from 8 known and 18 unidentified species are summarized in this paper. These secondary metabolites are mainly categorized into polyphenols, linear polyketides, macrolides, macrolactams, thiazolyl peptides, cyclic peptides, glycopeptides, amide and amino derivatives, glycoside derivatives, enediyne derivatives and sesquiterpenes. Meanwhile, they mainly showed unique antimicrobial, anti-cancer, antioxidant, anti-hyperglycemic, and enzyme inhibition activities. In addition, the biosynthetic pathways of several potent bioactive compounds and derivatives are included and the prospect of the chemical substances obtained from Amycolatopsis is also discussed to provide ideas for their implementation in the field of therapeutics and drug discovery.

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Anti-proliferative and Antioxidant Activities of 1-methoxy-3-methyl-8-hydroxy-anthraquinone, a Hydroxyanthraquinoid Extrolite Produced by Amycolatopsis thermoflava strain SFMA-103

Cited by 9 publications

References 0 publications

Bioactive secondary metabolites from marine Actinomyces sp. AW6 with an evaluation of ADME-related physicochemical properties

Bioactive secondary metabolites from marine Actinomyces sp. AW6 with an evaluation of ADME-related physicochemical properties

Inhibition of Xanthine oxidase by 1-O-methyl chrysophanol, a hydroxyanthraquinone isolated fromAmycolatopsis thermoflavaICTA 103

Secondary Metabolites of the Genus Amycolatopsis: Structures, Bioactivities and Biosynthesis

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