ChemInform Abstract: SOME STRUCTURAL RELATIONSHIPS AMONG CYTOTOXIC AND ANTITUMOR BENZOPHENANTHRIDINE ALKALOID DERIVATIVES

Stermitz, Frank R.; Larson, Kenneth A.; Kom, D. K.

doi:10.1002/chin.197349461

Cited by 6 publications

(9 citation statements)

References 1 publication

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“…Some of the above-mentioned active compounds were also found to possess cytotoxicity in previous reports. For instance, compounds 5, 7 and 10 were tested against KB tumour cells in vitro (Stermitz et al 1973); compounds 2, 9 and 10 exhibited cytotoxicity against P-388 or HT-29 cell lines (Chen et al 2005). From the view of structure -activity relationship (Deng & Qin 2010), these in vitro results suggested that for the active compounds in this work, cytotoxic activities were enhanced by methoxylation at C-6.…”

Section: Resultsmentioning

confidence: 92%

Cytotoxicity of benzophenanthridine alkaloids from the roots ofZanthoxylum nitidum(Roxb.) DC. var.fastuosumHow ex Huang

Wang

Fan

Tian

et al. 2015

Natural Product Research

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This work aimed to investigate benzophenanthridine from the roots of Zanthoxylum nitidum (Roxb.) DC. var. fastuosum How ex Huang for the first time. Thirteen benzophenanthridines were isolated, and our results of the cytotoxic activities indicated that compound 6 exhibited the best potency against A549, Hela, SMMC-7721 and EJ, with the IC50 values of 27.50, 37.50, 16.95 and 60.42 μM, respectively. Compounds 7 and 11 also showed strong cytotoxicity when tested against the four human cancer cell lines (A549, Hela, SMMC-7721 and EJ), while only compounds 12 and 13 displayed cytotoxicity in inhibiting BALL-1 proliferation among all the compounds. These results suggested that benzophenanthridines may become a valid alternative of potential basis for new anti-proliferative agents.

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Section: Resultsmentioning

confidence: 92%

Cytotoxicity of benzophenanthridine alkaloids from the roots ofZanthoxylum nitidum(Roxb.) DC. var.fastuosumHow ex Huang

Wang

Fan

Tian

et al. 2015

Natural Product Research

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“…Compounds 1a and 2a were synthesised by the literatural method (Slavik & Slavikova, 1977). Compounds 1b, 1c, 2b and 2c were prepared according to the method of Stermitz et al (1973). Compounds 1d and 2d were prepared by previously described methods (Maclean, Gracey, & Saunders, 1969).…”

Section: Syntheses Of 1a-2ementioning

confidence: 99%

“…f. et Thoms., Macleaya and Bocconia species from the Papaveraceae family, and some members of Zanthoxylum (Rutaceae). Although the QBAs are a relatively small class of plant products, they have attracted much attention from researchers because of their bioactivities: anti-inflammatory (Lenfeld et al, 1981), antimicrobial (Mitscher et al, 1978;Navarro, Villarreal, Rojas, & Lozoya, 1996;Odebiyi & Sofowora, 1979), antitumour (Nakanishi, Suzuki, Mashiba, Ishikawa, & Yokotsuka, 1998;Stermitz, Larson, & Kim, 1973;Stermitz et al, 1975;Tin-Wa, Bell, Bevelle, Fong, & Farnsworth, 1974;Zee-Cheng & Cheng, 1975), antiviral (Sethi, 1979), cytotoxic (Cordell & Farnsworth, 1976) and anti-liver mitochondrial monoamine oxidase (Iagodina, Nikol'skaia, & Faddeeva, 2003). With respect to the antimicrobial activities of QBAs, previous research has mainly focused on the total alkaloids containing QBAs from the plant, while only a few studies on 1 and 2 have been reported.…”

Section: Introductionmentioning

confidence: 98%

Structural modification of sanguinarine and chelerythrine and their antibacterial activity

Miao

Yang

Zhou

et al. 2011

Natural Product Research

110

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In this study, five derivatives of sanguinarine (1) and chelerythrine (2) were prepared, with 1 and 2 as starting materials, by reduction, oxidation and nucleophilic addition to the iminium bond C=N+. The structures of all compounds were elucidated on account of their MS, ¹H-NMR and ¹³C-NMR data. The antibacterial activities of all compounds were screened, using Staphylococcus aureus, Escherichia coli, Aeromonas hydrophila and Pasteurella multocida as test bacteria. The minimum bacteriostatic concentration and minimum bactericidal concentration of the active compounds were determined by the turbidity method. The structure-activity relationships of 1 and 2 were discussed. The results showed that 1, 2 and their pseudoalcoholates were found to be potent inhibitors to S. aureus, E. coli and A. hydrophila, while the other derivatives were found to be inactive. The pseudoalcoholates might be the prodrugs of 1 and 2. The iminium bond in the molecules of 1 or 2 was the determinant for antibacterial activity, and the substituents at the 7 and 8 positions influenced the antibacterial activities of 1 and 2 against different bacteria.

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“…Several quaternary benzo[c] phenanthridine alkaloids from M. cordata exhibited cytotoxicity (Stermitz et al . ; Vrba et al . ), protease inhibitory (Iagodina et al .…”

Section: Introductionmentioning

confidence: 99%

Chemical Composition, Antimicrobial Activity and Mechanism of Action of Essential Oil from the Leaves of Macleaya Cordata (Willd.) R. Br

2014

Journal of Food Safety

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The essential oil from the leaves of Macleaya cordata R. Br. obtained by hydrodistillation was analyzed by gas chromatography/mass spectrometry (GC/ MS). Sixty-eight compounds consisting up to 92.53% of the essential oil were identified by GC and GC/MS analysis. The antibacterial activity and minimum inhibitory concentration (MIC) of the essential oil against several pathogens were evaluated. The results showed that bacteria had different sensitivities to essential oil of M. cordata with diameters of inhibition zones ranging from 8.5 ± 0.6 to 18.6 ± 1.9 mm and MIC values from 125 to 500 μg/mL. Among these bacteria, Ralstonia solanacearum was the most sensitive to essential oil. In addition, killtime assay also showed that the essential oil had a significant effect on the growth rate of surviving R. solanacearum. We concluded that the mechanism of action of the essential oil against R. solanacearum might be described as essential oil acting on membrane integrity according to the results of the leakage of electrolytes, the losses of content (proteins and reducing sugars) assays and electron microscopy observation. The treated cell membranes were severely damaged. The results presented here indicate that the essential oil of M. cordata may be a potential source of antimicrobial agents in the future.

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ChemInform Abstract: SOME STRUCTURAL RELATIONSHIPS AMONG CYTOTOXIC AND ANTITUMOR BENZOPHENANTHRIDINE ALKALOID DERIVATIVES

Cited by 6 publications

References 1 publication

Cytotoxicity of benzophenanthridine alkaloids from the roots ofZanthoxylum nitidum(Roxb.) DC. var.fastuosumHow ex Huang

Cytotoxicity of benzophenanthridine alkaloids from the roots ofZanthoxylum nitidum(Roxb.) DC. var.fastuosumHow ex Huang

Structural modification of sanguinarine and chelerythrine and their antibacterial activity

Chemical Composition, Antimicrobial Activity and Mechanism of Action of Essential Oil from the Leaves of Macleaya Cordata (Willd.) R. Br

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