Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials

• Jessica Villegas,
• Bryce C. Ball,
• Katelyn M. Shouse,
• Caleb W. VanArragon,
• Ashley N. Wasserman,
• Hannah E. Bhakta,
• Allen G. Oliver,
• Danielle A. Orozco-Nunnelly and
• Jeffrey M. Pruet

Beilstein J. Org. Chem. 2023, 19, 1511–1524, doi:10.3762/bjoc.19.108

• focused on designing, synthesizing, and testing the altered bioactivity of new variants of two original bioactive molecules found in the Argemone mexicana plant. Herein, we report upon 14 variants of berberine and four variants of chelerythrine that have been screened against a pool of 12 microorganisms

• tumor cytotoxicity effects for a number of the berberine derivatives. Keywords: benzylisoquinoline; berberine; chelerythrine; drug discovery; plant-derived antimicrobials; Introduction The isolation, or creation of novel antimicrobial agents is currently at the forefront of modern healthcare due to

• leaf methanol fractions, the main bioactive phytochemicals were identified as berberine, chelerythrine, and sanguinarine from this same report [9]. These three compounds are known antimicrobial agents, with a wide variety of biological activities [10][11][12]. The antimicrobial effects of berberine are

Come-back of phenanthridine and phenanthridinium derivatives in the 21st century

• Lidija-Marija Tumir,
• Marijana Radić Stojković and
• Ivo Piantanida

Beilstein J. Org. Chem. 2014, 10, 2930–2954, doi:10.3762/bjoc.10.312

• various DNA and RNA were not studied in detail. One of several reasons for the increased research on phenanthridines is the discovery of naturally occurring analogues, e.g., some protoberberine alkaloids (Figure 12, sanguinarine and chelerythrine), widely distributed in several botanical families

• exhibiting many therapeutic applications. Very extensive results would require a focused review, thus some examples are listed below as outline of the importance. Most of the sanguinarine (20) and chelerythrine (21) derivatives were typical DNA and RNA intercalators [100], some of them showing also

• intriguing interactions with ss-RNA, poly(A) [46]. However, either intercalative binding mode or structural similarity to EB did not hamper their biomedical applications. For instance, in a series of 5-methylbenzo[c]phenanthridinium derivatives, based on combination of sanguinarine (20)/chelerythrine (21