ArticleCommunications chemistry2022
Discovery, total syntheses and potent anti-inflammatory activity of pyrrolinone-fused benzoazepine alkaloids Asperazepanones A and B from Aspergillus candidus.
Article in Communications chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
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- Extracting Value from Marine and Microbial Natural Product Artifacts and Chemical Reactivity.Marine drugs · 2025Review
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- Three-step process for the synthesis of 10,11-dihydro-5RSC advances · 2025Article
- Recent Advances in Anti-Inflammatory Compounds from Marine Microorganisms.Marine drugs · 2024Review
- Discovery of a potential bladder cancer inhibitor CHNQD-01281 by regulating EGFR and promoting infiltration of cytotoxic T cells.Marine life science & technology · 2024Article
- Recent Discovery of Nitrogen Heterocycles from Marine-DerivedMarine drugs · 2024Review
- Anti-Inflammatory Peroxidized Chlorahololide-Type Dimers Are Artifacts of Shizukaol-Type Dimers: From Phenomena Discovery and Confirmation to Potential Underlying Mechanism.Molecules (Basel, Switzerland) · 2024Article
- Cytosporones W and X: Two Mutually Converting Epimers from a Mangrove Endophytic FungusACS omega · 2023Article
- Synthesis, Characterization and Biocompatibility Evaluation of Novel Chitosan Lipid Micro-Systems for Modified Release of Diclofenac Sodium.Biomedicines · 2023Article
Corrections and comments
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Authors and funding
9 authors.
Funding
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Abstract
Natural products are well established as an important resource and play an important role in drug discovery. Here, two pyrrolinone-fused benzoazepine alkaloids, (+)-asperazepanones A (1) and B (2) with a 6/7/5 ring system, together with the artifact (-)-asperazepanone A (1), were isolated from the coral-derived Aspergillus candidus fungus. Their structures including absolute configurations were elucidated by extensive spectroscopic methods, single crystal X-ray diffraction, and ECD calculations. Furthermore, total syntheses of (±)-1 and (±)-2 have been achieved starting from the commercially L-aspartic acid diethyl ester hydrochloride and monoethyl malonate in 7 and 8 steps, respectively. The key step in the syntheses was an intramolecular Friedel-Crafts reaction to build the unique tricyclic skeleton. Interestingly, (+)-2 not only showed obviously inhibitory activity against NO production, but also inhibited potent LPS-induced expression of TNF-α and IL-6 at the concentration of 0.1 μM. It thus represents a potentially promising lead for anti-inflammatory drug discovery.
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Registered trials
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