On our quest for new bioactive molecules from marine sources, two cyclic imines (, ) were isolated from a dinoflagellate extract, inhibiting the growth of the respiratory syncytial virus (RSV). Compound was identified as a known molecule portimine, while was elucidated to be a new cyclic imine, named kabirimine. The absolute stereochemistry of was determined by crystallographic work and chiral derivatization, whereas the structure of was elucidated by means of spectroscopic analysis and computational study on all the possible isomers. Compound showed potent cytotoxicity (CC < 0.097 µM) against HEp2 cells, while exhibited moderate antiviral activity against RSV with IC = 4.20 µM (95% CI 3.31-5.33).
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http://dx.doi.org/10.3390/md17060353 | DOI Listing |
Org Lett
January 2025
Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, California 95616, United States.
The reactivity between sulfonimidamide-derived imines and cyclic anhydrides has been investigated. Sulfonimidamide imines readily react with homophthalic anhydride under mild conditions in the presence of non-nucleophilic bases to yield complex lactam products with high diastereoselectivity. Furthermore, it was discovered that sulfonimidamide imines react with homophthalic anhydride in the absence of a base to yield distinct diastereomer products with high diastereoselectivity.
View Article and Find Full Text PDFChemistry
January 2025
VIT University, Materials Chemistry Division, School of Advanced Sciences, VIT University, 632014, Vellore, INDIA.
Amidines are a vital class of bioactive compounds and often necessitate multiple components for their synthesis. Therefore, exploring efficient and sustainable methodologies for their synthesis is indispensable. Herein, we disclose an alternative and greener method for synthesizing an unexplored new class of amidines through the photochemical synergistic effect of copper/nitroxyl radical catalysis.
View Article and Find Full Text PDFMar Drugs
January 2025
Toxicology of Contaminants Unit, Fougères Laboratory, ANSES (French Agency for Food, Environmental and Occupational Health & Safety), 35306 Fougères, France.
The pinnatoxins (PnTXs) and portimines, produced by , have been detected in several countries, raising concerns for human health. Although no human poisoning from these toxins has been reported so far, they have been shown to distribute throughout the rodent body after oral administration. Therefore, we investigated the impact of PnTX analogs (PnTX-A, -E, -F, -G, and -H) and portimine (8, 16, and 32 ng/mL) on intestinal barrier integrity and their oral bioavailability using human Caco-2 cell monolayers treated for 2, 6, and 24 h.
View Article and Find Full Text PDFInt J Mol Sci
December 2024
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov Str., 8, Kazan 420088, Russia.
Alkaloids are predominantly nitrogen-containing heterocyclic compounds that are usually isolated from plants, and sometimes from insects or animals. Alkaloids are one of the most important types of natural products due to their diverse biological activities and potential applications in modern medicine. Cyclic imines were chosen as starting compounds for the synthesis of alkaloids due to their high synthetic potential.
View Article and Find Full Text PDFMar Drugs
December 2024
Centre for Environment Fisheries and Aquaculture Science (CEFAS), Barrack Road, Weymouth DT4 8UB, UK.
Harmful algal biotoxins in the marine environment are a threat to human food safety due to their bioaccumulation in bivalve shellfish. Whilst official control monitoring provides ongoing risk management for regulated toxins in live bivalve molluscs, no routine monitoring system is currently in operation in the UK for other non-regulated toxins. To assess the potential presence of such compounds, a systematic screen of bivalve shellfish was conducted throughout Great Britain.
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