ReviewNatural product reports2018
Structural and stereochemical diversity in prenylated indole alkaloids containing the bicyclo[2.2.2]diazaoctane ring system from marine and terrestrial fungi.
Review in Natural product reports, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
28 citing papers in PubMed.
- The Mutually Inspiring Biological and Chemical Synthesis of Fungal Bicyclo[2.2.2]diazaoctane Indole Alkaloids.Chemical reviews · 2025Review
- Aspertaichamide B, a new anti-tumor prenylated indole alkaloid from the fungus Aspergillus japonicus TE-739D.Applied microbiology and biotechnology · 2024Article
- Biosynthetic Strategies of Berberine Bridge Enzyme-like Flavoprotein Oxidases toward Structural Diversification in Natural Product Biosynthesis.Biochemistry · 2024Review
- Discovery of Uncommon Tryptophan-Containing Diketopiperazines fromJournal of natural products · 2024Article
- Current Status of Indole-Derived Marine Natural Products: Synthetic Approaches and Therapeutic Applications.Marine drugs · 2024Review
- Construction of C2-indolyl-quaternary centers by branch-selective allylation: enabling concise total synthesis of the (±)-mersicarpine alkaloid.Chemical science · 2024Article
- Fungal P450 Deconstructs the 2,5-Diazabicyclo[2.2.2]octane RingJournal of the American Chemical Society · 2023Article
- An NmrA-like enzyme-catalysed redox-mediated Diels-Alder cycloaddition with anti-selectivity.Nature chemistry · 2023Article
- Combined Toxicity of the Most Common Indoor Aspergilli.Pathogens (Basel, Switzerland) · 2023Article
- Tryptophan-centered metabolic alterations coincides with lipid-mediated fungal response to cold stress.Heliyon · 2023Article
- Article
- Diprenylated cyclodipeptide production by changing the prenylation sequence of the nature's synthetic machinery.Applied microbiology and biotechnology · 2023Article
- Efficient production of a cyclic dipeptide (cyclo-TA) using heterologous expression system of filamentous fungus Aspergillus oryzae.Microbial cell factories · 2022Article
- Unified total synthesis of the brevianamide alkaloids enabled by chemical investigations into their biosynthesis.Chemical science · 2022Article
- Antibacterial spirooxindole alkaloids fromFrontiers in microbiology · 2022Article
- Article
- A general approach to 2,2-disubstituted indoxyls: total synthesis of brevianamide A and trigonoliimine C.Chemical science · 2021Article
- Structural basis of the stereoselective formation of the spirooxindole ring in the biosynthesis of citrinadins.Nature communications · 2021Article
- Total synthesis of brevianamide A.Nature chemistry · 2020Article
- A unified strategy to reverse-prenylated indole alkaloids: total syntheses of preparaherquamide, premalbrancheamide, and (+)-VM-55599.Chemical science · 2020Article
Corrections and comments
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Authors and funding
9 authors.
Funding
Abstract
Covering: up to February 2017 Various fungi of the genera Aspergillus, Penicillium, and Malbranchea produce prenylated indole alkaloids possessing a bicyclo[2.2.2]diazaoctane ring system. After the discovery of distinct enantiomers of the natural alkaloids stephacidin A and notoamide B, from A. protuberus MF297-2 and A. amoenus NRRL 35660, another fungi, A. taichungensis, was found to produce their diastereomers, 6-epi-stephacidin A and versicolamide B, as major metabolites. Distinct enantiomers of stephacidin A and 6-epi-stephacidin A may be derived from a common precursor, notoamide S, by enzymes that form a bicyclo[2.2.2]diazaoctane core via a putative intramolecular hetero-Diels-Alder cycloaddition. This review provides our current understanding of the structural and stereochemical homologies and disparities of these alkaloids. Through the deployment of biomimetic syntheses, whole-genome sequencing, and biochemical studies, a unified biogenesis of both the dioxopiperazine and the monooxopiperazine families of prenylated indole alkaloids constituted of bicyclo[2.2.2]diazaoctane ring systems is presented.
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