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Oxidation of four monoterpenoid indole alkaloid classes by three cytochrome P450 monooxygenases from Tabernaemontana litoralis.
Plant J
December 2024
Department of Chemistry, University of New Brunswick, Fredericton, New Brunswick, E3B 5A3, Canada.
Article Synopsis
- * This study focuses on the biosynthesis of rare MIAs in the Tabernaemontana litoralis plant, identifying new CYP enzymes that specifically modify MIA structures, including the discovery of a new MIA compound.
- * The research enhances our understanding of how MIAs are synthesized and diversified in T. litoralis, suggesting its potential for future studies in this area.
Cytotoxic monoterpenoid indole alkaloids from Tabernaemontana bovina.
Phytochemistry
February 2025
School of Pharmaceutical Sciences, College of Modern Biomedical Industry, Department of Zoology & Yunnan Key Laboratory of Pharmacology for Natural Products, Kunming Medical University, Kunming, 650500, People's Republic of China. Electronic address:
Chemical investigation of the native medicinal plant Tabernaemontana bovina led to the isolation of five previously unreported monoterpenoid indole alkaloids tabernovinaines A-E (1-5) together with twenty-seven known analogs (6-32), including a bisindole alkaloid 1 with the (E)-4-aminobut-3-en-2-one fragment, as well as a unique cage skeleton 2 containing 6/5/8/6/6 ring system. The chemical structures of these unreported compounds were elucidated using mass spectrometry, NMR spectroscopy, circular dichroism, density functional theory calculations, and derivatizations. The activity evaluation shows that the bisindole alkaloid 1 revealed a potential cytotoxic effect by inducing HepG2 cell apoptosis and damaging clonal sphere expansion.
View Article and Find Full Text PDFCathagines A-D, new bisindole alkaloids from Catharanthus roseus.
J Nat Med
November 2024
Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41 Shinagawa-ku, Tokyo, 142-8501, Japan.
Four new bisindole alkaloids, cathagines A (1)-D (4) consisting of an aspidosperma and the fused tetracyclic 3-spirooxindole derived from an iboga type skeleton were isolated from the whole plant of Catharanthus roseus. The structures including absolute stereochemistry were elucidated on the basis of 2D NMR data and CD spectra. Cathagine B (2) showed moderate anti-malarial activity against Plasmodium falciparum 3D7.
View Article and Find Full Text PDFChemical Information Network and Molecular Docking Inspire the Novel Indole Discovery Against Glioma from Tabernaemontana corymbosa.
Chem Biodivers
November 2024
School of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang, 550025, People's Republic of China.
Article Synopsis
- The study investigated the medicinal plant Tabernaemontana corymbosa, focusing on its alkaloid compounds believed to have various pharmacological effects.
- Researchers isolated a new indole alkaloid, tabercorympyline A, along with seven known indoles, using spectroscopic techniques and quantum chemical calculations to determine their structures.
- The isolated compounds were tested for anti-glioma activity in vitro, with some showing significant inhibition of glioma cells, and molecular docking was used to explore potential therapeutic mechanisms.
Genome-based discovery of pachysiphine synthases in Tabernaemontana elegans.
Plant J
December 2024
Biomolécules et Biotechnologies Végétales, EA2106, Université de Tours, Tours, 37200, France.
Article Synopsis
- Plant-specialized metabolism is a rich source of bioactive compounds, like monoterpene indole alkaloids (MIAs), known for their health benefits including anticancer and neuroactive properties.
- The types of MIAs, particularly pachysiphine derivatives, have promising medical applications but are found in very low quantities in certain plant species, and there is a lack of genomic data needed to enhance their production.
- This study presents the genome sequence of the toad tree (Tabernaemontana elegans) and identifies genes that can synthesize pachysiphine, leading to engineered MIAs in yeast, thus paving the way for better production of these valuable compounds for pharmaceutical use.
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