Synthesis and biological evaluation of novel 8-aminomethylated oroxylin A analogues as α-glucosidase inhibitors

Babu, T. Hari; Rao, V. Rama Subba; Tiwari, Ashok Kumar; Babu, K. Suresh; Srinivas, P.; Ali, Amtul Z.; Rao, J. Madhusudana

doi:10.1016/j.bmcl.2008.01.055

Cited by 46 publications

(16 citation statements)

References 15 publications

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“…The activity of quinone-containing compounds against mites can be related to the generation of reactive oxygen species [ 25 ], inhibition of mitochondrial respiration [ 26 , 27 ], and DNA intercalation and breakdown. Some shikonins were also active against the stored product pests, Acanthoscelides obtectus and Epilachna varivestis [ 28 ].…”

Section: Discussionmentioning

confidence: 99%

Identification of Onosma visianii Roots Extract and Purified Shikonin Derivatives as Potential Acaricidal Agents against Tetranychus urticae

et al. 2017

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There is an increasing need for the discovery of reliable and eco-friendly pesticides and natural plant-derived products may play a crucial role as source of new active compounds. In this research, a lipophilic extract of Onosma visianii roots extract containing 12% of shikonin derivatives demonstrated significant toxicity and inhibition of oviposition against Tetranychus urticae mites. Extensive chromatographic separation allowed the isolation of 11 naphthoquinone derivatives that were identified by spectral techniques and were tested against Tetranychus urticae. All the isolated compounds presented effects against the considered mite and isobutylshikonin (1) and isovalerylshikonin (2) were the most active, being valuable model compounds for the study of new anti-mite agents.

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Section: Discussionmentioning

confidence: 99%

Identification of Onosma visianii Roots Extract and Purified Shikonin Derivatives as Potential Acaricidal Agents against Tetranychus urticae

et al. 2017

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“…Previous reports [ 49 , 50 , 51 , 60 , 61 ] have shown that the bioactivity increased when aminomethyl groups were incorporated at the C-8 position. Our results are consistent with this.…”

Section: Discussionmentioning

confidence: 97%

“…The inhibitory activities of adriamycin salicylamide Mannich base against MCF-7 and PC-3 cells are four times better than that of adriamycin, while simultaneously reducing the clinical side effects [ 48 ]. In addition, several studies have shown that 8-aminomethylated oroxylin A analogs demonstrated significantly improved α-glucosidase inhibitory activity [ 49 ], nitrogen-containing baicalein/quercetin analogs exhibited potent CDK1/cyclin B inhibitory activity [ 50 ], and 8-aminomethylluteolin derivatives displayed potential anti-inflammatory activity [ 51 ].…”

Section: Introductionmentioning

confidence: 99%

Nitrogen-Containing Apigenin Analogs: Preparation and Biological Activity

Zhao

Wang

et al. 2012

Molecules

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A series of nitrogen-containing apigenin analogs 4a–j was synthesized via Mannich reactions to develop anticancer, antibacterial, and antioxidant agents from plant-derived flavonoids. The chemical structures of these compounds were confirmed using 1H-NMR, 13C-NMR, and ESI-MS. The in vitro biological activities of the analogs were evaluated via assays of their antiproliferative, antibacterial, and antioxidant activities. The prepared apigenin analogs exhibited different antiproliferative activities against four human cancer cell lines, namely human cervical (HeLa), human hepatocellular liver (HepG2), human lung (A549), and human breast (MCF-7) cancer cells. Compound 4i showed the most favorable in vitro antiproliferative activity with IC50 values of 40, 40, 223, and 166 μg/mL against HeLa, HepG2, A549, and MCF-7, respectively. The 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity assay also showed that 4i had the most potent antioxidant activity, with the smallest IC50 value (334.8 μg/mL). The antibacterial activities of the analogs were determined using a two-fold serial dilution technique against four pathogenic bacteria, namely Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa. All the prepared apigenin analogs exhibited more potent activities than the parent apigenin. Compounds 4h and 4j, in particular, exhibited the best inhibitory activities against the Gram-positive bacteria Staphylococcus aureus and Bacillus subtilis with MIC values of 3.91 and 1.95 μg/mL, respectively.

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“…1 H NMR (300 MHz, CDCl 3 ): δ 2.03 (s, 3H, 9 0 -CH 3 ), 2.24 (s, 3H, 2-CH 3 ), 3.14 (dd, 2H, J=6.8 Hz, 14.8 Hz, H-2 0 ), 3.98 (s, 3H, 5-OMe), 3.90 (dd, 1H, J=5.4 Hz, 17.1 Hz, H-6 0 a), 4.03 (dd, 1H, J=5.4 Hz, 17.1 Hz, H-6 0 b), 4.27 (dd, 2H, J=6.8 Hz, 14.8 Hz, H-3 0 ), 7.15 (dd, 1H, J=1.1 Hz, 8.5 Hz, H-6), 7.62 (t, 1H, J=7.5 Hz, 8.5 Hz, H-7), 7.75 (dd, 1H, J=1.1 Hz, 7.5 Hz, H-8). 13 (11), 260 (63), 248 (47), 234 (79), 220 (9), 203 (100), 175 (33), 147 (11), 99.1 (15).…”

Section: Methodsmentioning

confidence: 99%

“…1 H NMR (300 MHz, CDCl 3 ): δ 0.89 (d, 3H, J= 5.8 Hz, 1 00 -CH 3 ), 0.90 (t, 3H, J=7.2 Hz, 3 00 -CH 3 ), 1.25-1.28 (2H, m, H-2 00 ), 1.48-1.52 (1H, m, H-1 00 ), 2.03 (s, 3H, 9 0 -CH 3 ), 2.24 (3H, s, 2-CH 3) , 3.84 (dd, 2H, J=6.8 Hz, 14.8 Hz, H-2 0 ), 3.98 (s, 3H, -OMe), 4.44 (dd, 2H, J=6.8 Hz,14.8 Hz, H-3 0 ), 4.63 (dd, 1H, J=7.2 Hz, H-6 0 ), 7.15 (dd, 1H, J= 1.1, 8.5 Hz, H-6), 7.62 (t, 1H, J=7.5 Hz, 8.5 Hz, H-7), 7.75 (dd, 1H, J=1.1 Hz, 7.5 Hz, H-8). 13 16), 301 (12), 288 (23), 260 (9), 217 (100), 202 (58), 175 (42), 99 (8).…”

Section: -(8-methoxymentioning

confidence: 99%

Synthesis and Insect Antifeedant Activity of Plumbagin Derivatives with the Amino Acid Moiety

Sreelatha

Hymavathi

Babu

et al. 2009

J. Agric. Food Chem.

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A series of plumbagin derivatives (4a-4k) containing an amino acid moiety were synthesized under mild esterification conditions in excellent yields (35%-80%) and screened for their antifeedant activities in tobacco caterpillar (Spodoptera litura) and castor semilooper (Achaea janata) using a no-choice laboratory bioassay. The parent compound plumbagin lacked significant activity, but the analogues were effective in reducing feeding by two insect species. The introduction of an N-acetyl-l-amino acid side chain to the Michael adduct of plumbagin at the third position of the quinone moiety significantly increased antifeedant activity. Several of the analogues were also toxic or caused developmental abnormalities following topical administration.

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Synthesis and biological evaluation of novel 8-aminomethylated oroxylin A analogues as α-glucosidase inhibitors

Cited by 46 publications

References 15 publications

Identification of Onosma visianii Roots Extract and Purified Shikonin Derivatives as Potential Acaricidal Agents against Tetranychus urticae

Identification of Onosma visianii Roots Extract and Purified Shikonin Derivatives as Potential Acaricidal Agents against Tetranychus urticae

Nitrogen-Containing Apigenin Analogs: Preparation and Biological Activity

Synthesis and Insect Antifeedant Activity of Plumbagin Derivatives with the Amino Acid Moiety

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