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The cholinesterase inhibitory activity was examined of synthetic carbazole‐coumarin hybrids, with long chain hydrocarbons, triazole, or piperazine as linkers. The most effective acetylcholinesterase inhibitor was 7‐((12‐(9H‐carbazol‐9‐yl)dodecyl)oxy)‐2H‐chromen‐2‐one (3 l), with an IC50 value of 6.86 μM and a high selectivity over butyrylcholinesterase. Compound 3 l also exhibited mixed‐type AChE inhibition in a kinetic study, with a Ki value of 4.87 μM. In addition, molecular docking of compound 3 l toward AChE was done to elucidate the inhibition at both the peripheral anionic and catalytic active sites. Furthermore, the HepG2 and Vero cells were unaffected by toxicity from compound 3 l. Therefore, these findings could be exploited to create a number of carbazole‐coumarin hybrids for future potential treatments for Alzheimer's disease. [ABSTRACT FROM AUTHOR]

Artocarpus lacucha, a plant in the Moraceae family, has traditionally been used in Southeast Asian medicine to treat various ailments. This study investigated the insecticidal potential against Spodoptera litura of several compounds extracted from A. lacucha using a topical application method. A sequential extraction method was employed with A. lacucha stems to identify the most toxic crude extract by using hexane, dichloromethane, ethyl acetate, and methanol solvents. Subsequently, the most toxic crude extract was analyzed for chemical composition by HPLC, followed by the isolation process. Among these crude extracts, the ethyl acetate crude extract was the most toxic to second-instar S. litura larvae (24-h LD50 value of ∼9.07 µg/larva). Our results showed that the catechin isolated from the ethyl acetate crude extract exhibited the highest toxicity against this insect (24-h LD50 value of ∼8.37 µg/larva). Additionally, catechin significantly decreased the activities of acetylcholinesterase, carboxylesterases, and glutathione S-transferase in the larvae. These findings suggest that catechin isolated from A. lacucha could be a potential insecticidal agent against S. litura. However, the toxicity and persistence of catechin under field conditions need to be further investigated to develop this novel insecticide. [ABSTRACT FROM AUTHOR]

The discovery of eco-friendly plant-based insecticides is currently booming in research with an attempt to replace synthetic chemical insecticides causing tremendous adverse effects. The present work studied the insecticidal potential of ginger, an important medicinal plant. Four crude extracts from Zingiber officinale rhizomes were evaluated for their contact toxicity against second instars of Spodoptera litura, Spodoptera exigua and Spodoptera frugiperda using the topical application. The hexane extract exhibited the strongest toxicity to S. exigua with the LD50 of 9.92 and 8.40 µg/larva at 24 and 48 h posttreatment, respectively, followed by S. frugiperda. Comparative toxicity of the most abundant secondary metabolites from the hexane extract, gingerols and shogaols, against both insects concluded that 8-shogaol (5) was identified as the most active compound against S. frugiperda with the LD50 of 7.68 and 3.96 µg/larva at 24 and 48 h posttreatment, respectively. [ABSTRACT FROM AUTHOR]

Comprehensive phytochemical examination from different perspectives using preparative and analytical chromatographic techniques combined with spectroscopic/spectrometric methods of the so-called "yellow twig" Nauclea orientalis (L.) L. (Rubiaceae) led to the identification of 13 tryptamine-derived (=monoterpene-indole) alkaloids. The identified alkaloids comprise strictosamide and four of its glucosidic derivatives, three oxindole derivatives, and five yellow-colored angustine-type aglycones. Qualitative and quantitative HPLC analyses showed the enrichment of strictosamide in all studied organs. Based on these results, we performed metabolomic analyses of monoterpene-indole alkaloids and made a 1H NMR in vitro monitoring of enzymatic deglucosylation of strictosamide. A comparison of the stability of strictosamide and its enantiomer vincoside lactam by theoretical calculations was also performed revealing a slightly higher stability of vincoside lactam. Additionally, we conducted two different anti-feedant assays of strictosamide using larvae of the polyphageous moth Spodoptera littoralis Boisduval. The obtained results indicate that generally two different biosynthetic pathways are most likely responsible for the overall alkaloid composition in this plant. Strictosamide is the key compound in the broader pathway and most likely the source of the identified angustine-type aglycones, which may contribute significantly to the yellow color of the wood. Its cross-organ accumulation makes it likely that strictosamide is not only important as a reservoir for the further biosynthesis, but also acts in the plants' defense strategy. [ABSTRACT FROM AUTHOR]

Phytochemical investigation of leaves and stembark of Artocarpus lacucha collected in Thailand resulted in three yet undescribed isomeric flavan-3-ol derivatives (1–3), the four known compounds gambircatechol (4), (+)-catechin (5), (+)-afzelechin (6) and the stilbene oxyresveratrol (7). Compounds 1 to 3 feature 6/6/5/6/5/6 core structures. All structures were deduced by NMR and MS, while density functional theory (DFT) calculations on B3LYP theory level were performed of compounds 1 to 3 to support the stereochemistry in positions 2 and 3 in the C-ring. Possible biosynthetic pathways leading to 4 are discussed. The DPPH assay revealed high radical scavenging activities for 1 (EC50 = 9.4 ± 1.0 µmol mL−1), 2 (12.2 ± 1.1), 3 (10.0 ± 1.5) and 4 (19.0 ± 2.6), remarkably lower than ascorbic acid (EC50 = 34.9) and α-tocopherol (EC50 = 48.6). A cytotoxicity assay revealed moderate but consistent antiproliferative properties of 1 in CH1/PA-1 (ovarian teratocarcinoma) and SW480 (colon carcinoma) cells, with IC50 values of 25 ± 6 and 34 ± 4 µM, respectively, whereas effects in A549 (non-small cell lung cancer) cells were rather negligible. The performed DCFH-DA assay of 1 in the former cell lines confirmed potent antioxidative effects even in the cellular environment. [ABSTRACT FROM AUTHOR]

Phytochemical investigation of Artocarpus lacucha Buch.-Ham (Moraceae) leaves led to the identification of three of the rarely found flavan-benzofuranes named artocarpinol C ( 1 ), 3- epi -artocarpinol C ( 2 ), and artocarpinol D ( 6 ) along with six known flavan derivatives. Thus, a total of six artocarpinols are now described. All their chemical structures and absolute configurations were established by one dimensional (1D)- and two-dimensional (2D) NMR, infrared (IR), electronic circular dichroism (ECD), high-resolution electrospray ionisation mass spectrometry (HR-ESI-MS), and optical rotation (OR). Density functional theory (DFT) calculations based on the B3LYP theory level were conducted to determine the stereochemistry at positions 2 and 3 in the C-ring. All compounds exhibited in vitro radical scavenging activities, and compounds 3 and 5 demonstrated pronounced intracellular antioxidative effects in colon carcinoma cells (SW480), as determined by the DCFH-DA assay. Compounds 3 and 5 exhibited further high affinities for binding to the active site of human glutathione reductase. These molecular properties are discussed with regard to possible applications., Competing Interests: The authors declare no competing financial interest., (© 2024 The Authors. Published by American Chemical Society.)