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Search for "berberine" in Full Text gives 13 result(s) in Beilstein Journal of Organic Chemistry.
Photoinduced in situ generation of DNA-targeting ligands: DNA-binding and DNA-photodamaging properties of benzo[c]quinolizinium ions
Beilstein J. Org. Chem. 2024, 20, 101–117, doi:10.3762/bjoc.20.11
- structurally related alkaloids berberine [61][62][63][64][65] and coralyne [36][66][67] have been shown already to act as efficient photosensitizers for DNA damage. To the best of our knowledge, however, benzo[c]quinolizinium derivatives have not been investigated with respect to their DNA-photodamaging
Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials
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
- (five Gram-positive and four Gram-negative bacteria, and three fungi). Additionally, the crystal structures of two berberine variants are described. Several berberine variants show enhanced antibacterial activity compared to the unaltered plant-derived molecule. We also report promising preliminary
- 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
Synthesis of 10-O-aryl-substituted berberine derivatives by Chan–Evans–Lam coupling and investigation of their DNA-binding properties
Beilstein J. Org. Chem. 2021, 17, 991–1000, doi:10.3762/bjoc.17.81
- berberrubine and berberine derivatives were synthesized by the Cu2+-catalyzed Chan–Evans–Lam coupling of berberrubine with arylboronic acids and subsequent 9-O-methylation. The reaction is likely introduced by the Cu2+-induced demethylation of berberrubine and subsequent arylation of the resulting 10-oxyanion
- functionality. Thus, this synthetic route represents the first successful Cu-mediated coupling reaction of berberine substrates. The DNA-binding properties of the 10-O-arylberberine derivatives with duplex and quadruplex DNA were studied by thermal DNA denaturation experiments, spectrometric titrations as well
- -DNA by terminal stacking. Keywords: berberine alkaloids; Cu-mediated coupling reactions; DNA recognition; nucleic acids; quadruplex DNA; Introduction Berberine (1a) is the most prominent member of the protoberberine family, i.e., a group of tetracyclic isoquinolinium alkaloids [1]. Like many members
Synthesis and investigation of quadruplex-DNA-binding, 9-O-substituted berberine derivatives
Beilstein J. Org. Chem. 2020, 16, 2795–2806, doi:10.3762/bjoc.16.230
- berberine derivatives was synthesized by the Cu-catalyzed click reaction of 9-propargyladenine with 9-O-(azidoalkyl)berberine derivatives. The association of the resulting berberine–adenine conjugates with representative quadruplex-forming oligonucleotides 22AG dA(G3TTA)3G3 and a2 d(ACAG4TGTG4)2 was
- examined with photometric and fluorimetric titrations, thermal DNA denaturation analysis, and CD spectroscopy. The results from the spectrometric titrations indicated the formation of 2:1 or 1:1 complexes (ligand:G4-DNA) with log Kb values of 10–11 (2:1) and 5–6 (1:1), which are typical for berberine
- with one representative ligand from the series that such berberine–adenine conjugates exhibit a selective binding, specifically a selectivity to quadruplex DNA in competition with duplex DNA, and a preferential thermal stabilization of the G4-DNA forms 22AG and KRAS. Notably, the experimental data do
Synthesis of new dihydroberberine and tetrahydroberberine analogues and evaluation of their antiproliferative activity on NCI-H1975 cells
Beilstein J. Org. Chem. 2020, 16, 1606–1616, doi:10.3762/bjoc.16.133
- Molecular Biology, Department of Biomolecular Sciences, University of Urbino “Carlo Bo”, Via Saffi 2, 61029 Urbino, Italy 10.3762/bjoc.16.133 Abstract Dihydroberberine (DHBER), the partially reduced form of the alkaloid berberine (BER), is known to exhibit important biological activities. Despite this fact
- various inflammatory diseases. The main component of this rhizome is berberine (BER), an alkaloid with numerous pharmacological properties, which include anticancer and anti-inflammatory activities [1]. However, the low bioavailability, poor solubility, and moderate nucleic acid binding affinity
Synthesis of 9-O-arylated berberines via copper-catalyzed CAr–O coupling reactions
Beilstein J. Org. Chem. 2019, 15, 1575–1580, doi:10.3762/bjoc.15.161
- Qiaoqiao Teng Xinhui Zhu Qianqian Guo Weihua Jiang Jiang Liu Qi Meng Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China 10.3762/bjoc.15.161 Abstract Berberine is a widely used antimicrobial
- 9-O-phenylene-bridged berberine dimer (5) was synthesized by copper-catalyzed cross-coupling of tetrahydroberberrubine and aryl iodides, followed by oxidation with I2. Keywords: arylation; berberines; cross-coupling; copper; lipophilicity; structural modification; Introduction Berberine (BBR) is a
- the fact that 9-O-functionalization is well-established. Therefore, to further diversify the BBR structure and to provide more potent drug candidates in the future, we herein report the first synthetic study on 9-O-arylated berberine. Results and Discussion In an analogous manner as described for 9-O
Synthesis of a water-soluble 2,2′-biphen[4]arene and its efficient complexation and sensitive fluorescence enhancement towards palmatine and berberine
Beilstein J. Org. Chem. 2018, 14, 2236–2241, doi:10.3762/bjoc.14.198
- , Shanghai 200444, P. R. China 10.3762/bjoc.14.198 Abstract A water-soluble 2,2′-biphen[4]arene (2,2’-CBP4) containing eight carboxylato moieties was synthesized and characterized. Its complexation behavior towards two alkaloids, palmatine (P) and berberine (B), was investigated by means of fluorescence and
- = (2.29 ± 0.27) × 106 M−1) is 3.9 times larger than that of P (Ka = (5.87 ± 0.24) × 105 M−1). Keywords: berberine; biphenarenes; host–guest complexes; molecular recognition; palmatine; Introduction Host–guest chemistry in water is significantly important due to its extensive applications in biology
- carboxylato moieties, 2,2’-CBP4 (Scheme 1), and its binding behavior and fluorescent spectrum characteristic towards two alkaoilds, palmatine (P) and berberine (B), in water solution. In particular, the fluorescence intensities of the two guests have been considerably enhanced after complexation. As a member
A practical and efficient approach to imidazo[1,2-a]pyridine-fused isoquinolines through the post-GBB transformation strategy
Beilstein J. Org. Chem. 2017, 13, 817–824, doi:10.3762/bjoc.13.82
- ], and antitumor activities [11]. For example, the natural alkaloids berberine (IV) and narciclasine (V) possess antiplasmodial and antiviral activity, respectively [12][13]. Indotecan (VI) and its analog idimitecan (VII) were identified as topoisomerase I inhibitors, and were promoted into phase I
Interactions between photoacidic 3-hydroxynaphtho[1,2-b]quinolizinium and cucurbit[7]uril: Influence on acidity in the ground and excited state
Beilstein J. Org. Chem. 2017, 13, 203–212, doi:10.3762/bjoc.13.23
- , berberine and coptisine, which were also shown to bind to CB[7] [38][39][40] and may thus serve as an appropriate comparison. Results Synthesis Hydroxynaphthoquinolizinium 2 was synthesized by the established cyclodehydration route (Scheme 1) [41][42]. Thus, the quaternization of 2-(1,3-dioxolan-2-yl
- that can thread nicely into the binding site. Notably, the structurally resembling alkaloids berberine (8a) and palmatine (8b), that contain an angularly annelated quinolizinium unit, also bind to CB[7]. But whereas palmatine (8b) has essentially the same binding constant as 2 (Kb = 4.3 × 104 M−1, in
- phosphate buffer) [39], berberine has a significantly higher affinity (Kb = 4.2 × 105 M−1, in phosphate buffer) [40]; although both complexes are proposed to have nearly the same structure. The origin of these inconsistent data has not been assessed or discussed so far. But these observations suggest that
Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides
Beilstein J. Org. Chem. 2016, 12, 1512–1550, doi:10.3762/bjoc.12.148
- mechanism is reminiscent of the formation of a tetrahydropyridine ring by the berberine bridge enzyme in plant alkaloid biosynthesis. It starts with S-adenosyl-L-methionine (SAM)-dependent methylation of the secondary hydroxy group in 81 by the O-methyltransferase Leu14 (Scheme 14a) [71][72][73][74
Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins
Beilstein J. Org. Chem. 2016, 12, 662–669, doi:10.3762/bjoc.12.66
- -methoxyhydnocarpin has been described to enhance the antimicrobial activity of berberine [19]. In the light of steadily growing antibiotic resistance any potent and nontoxic MDR inhibitor is of utmost importance. Hydnocarpin has also antineoplastic activity due to sensitizing multidrug-resistant cancer cell lines
Beyond catalyst deactivation: cross-metathesis involving olefins containing N-heteroaromatics
Beilstein J. Org. Chem. 2015, 11, 2223–2241, doi:10.3762/bjoc.11.241
- temperature (Scheme 11) [48]. This method was used to prepare polycyclic scaffolds that can be encountered in diverse alkaloid natural products such as coralyne and berberine (Scheme 12) [49]. Similarly, enyne ring-closing metathesis reactions were performed to access a variety of vinyl-3,4
The chemistry of isoindole natural products
Beilstein J. Org. Chem. 2013, 9, 2048–2078, doi:10.3762/bjoc.9.243
- , a term designated by Shamma [75], are abundantly found in South American members of the botanical family of Berberis (Berberidaceae). Along with the ever present isoquinoline berberine (92), the isoindole-containing benzazepines chilenine (93) [76], lennoxamine (94) [77] and chilenamine (95) [78
- cyclization gives the tetracyclic carbon skeleton, which upon further methylation and oxidation furnishes berberine (92) [80]. Prechilenine (102), itself isolated as its O-methyl ether is formed via oxidation [78]. A base-catalyzed semipinacol-type rearrangement yields 93 [76]. Chilenine (93) can be further
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