ArticleAngewandte Chemie (International ed. in English)2020
Diels-Alder Reactions During the Biosynthesis of Sorbicillinoids.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 37 papers.
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37 citing papers in PubMed, 90 citations in OpenAlex.
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- Anti-Inflammatory Secondary Metabolites fromMarine drugs · 2025Article
- Total synthesis of a sorrentanone ester library and evaluation of its antimicrobial potential.Scientific reports · 2025Article
- Structural and Mechanistic Characterization of the Flavin-Dependent Monooxygenase and Oxidase Involved in Sorbicillinoid Biosynthesis.ACS chemical biology · 2025Article
- Metabolic Engineering of Filamentous FungusJournal of agricultural and food chemistry · 2025Article
- Bioactive sorbicillinoid derivatives from an endophytic fungusFrontiers in microbiology · 2025Article
- Biosynthetic Strategies of Berberine Bridge Enzyme-like Flavoprotein Oxidases toward Structural Diversification in Natural Product Biosynthesis.Biochemistry · 2024Review
- Chemoenzymatic total synthesis of sorbicillactone A.Communications chemistry · 2024Article
- Genome mining and biosynthetic pathways of marine-derived fungal bioactive natural products.Frontiers in microbiology · 2024Review
- Genomics-driven derivatization of the bioactive fungal sesterterpenoid variecolin: Creation of an unnatural analogue with improved anticancer properties.Acta pharmaceutica Sinica. B · 2024Article
- Chemo-enzymatic total synthesis: current approaches toward the integration of chemical and enzymatic transformations.Beilstein journal of organic chemistry · 2024Review
- Mono- and Dimeric Sorbicillinoid Inhibitors Targeting IL-6 and IL-1β from the Mangrove-Derived FungusInternational journal of molecular sciences · 2023Article
- Chemo-enzymatic total synthesis of the spirosorbicillinols.Communications chemistry · 2023Article
- Effects of Carbon, Nitrogen, Ambient pH and Light on Mycelial Growth, Sporulation, Sorbicillinoid Biosynthesis and Related Gene Expression inJournal of fungi (Basel, Switzerland) · 2023Article
- Dearomative logic in natural product total synthesis.Natural product reports · 2022Review
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- Discovery of branching meroterpenoid biosynthetic pathways inChemical science · 2022Article
- Organocatalytic Enantioselective Synthesis of Bicyclo[2.2.2]octenones via Oxaziridinium Catalysed ortho-Hydroxylative Phenol Dearomatization.Angewandte Chemie (International ed. in English) · 2022Article
- Sorbicillinoid Derivatives with the Radical Scavenging Activities from the Marine-Derived FungusJournal of fungi (Basel, Switzerland) · 2022Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 2 countries.
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No grant is acknowledged in the PubMed record.
Abstract
The sorbicillinoids are a class of biologically active and structurally diverse fungal polyketides arising from sorbicillin. Through co-expression of sorA, sorB, sorC, and sorD from Trichoderma reesei QM6a, the biosynthetic pathway to epoxysorbicillinol and dimeric sorbicillinoids, which resemble Diels-Alder-like and Michael-addition-like products, was reconstituted in Aspergillus oryzae NSAR1. Expression and feeding experiments demonstrated the crucial requirement of the flavin-dependent monooxygenase SorD for the formation of dimeric sorbicillinoids, hybrid sorbicillinoids, and epoxysorbicillinol in vivo. In contrast to prior reports, SorD catalyses neither the oxidation of 2',3'-dihydrosorbicillin to sorbicillin nor the oxidation of sorbicillinol to oxosorbicillinol. This is the first report that both the intermolecular Diels-Alder and Michael dimerization reactions, as well as the epoxidation of sorbicillinol are catalysed in vivo by SorD.
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