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Ring contraction and ring expansion reactions in terpenoid biosynthesis and their application to total synthesis. [PDF]
Kratena N, Heinzig N, Gärtner P.
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AbstractFungal meroterpenoids are a diverse group of hybrid natural products with impressive structural complexity and high potential as drug candidates. In this work, we evaluate the promiscuity of the early structure diversity‐generating step in fungal meroterpenoid biosynthetic pathways: the multibond‐forming polyene cyclizations catalyzed by the ...
Makoto Fujita +2 more
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Organic Letters, 2022
The biosynthetic gene cluster of atlantinone B (10) was discovered in Penicillium chrysogenum MT-40. A multifunctional cytochrome P450 (AtlD) encoded by the cluster is responsible for the formation of the unique lactone-bridged ring and the 16β-hydroxyl of atlantinone B, and a new terpene cyclase (AtlC) can unprecedentedly accept the demethylated ...
Bo-wen Qi +11 more
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The biosynthetic gene cluster of atlantinone B (10) was discovered in Penicillium chrysogenum MT-40. A multifunctional cytochrome P450 (AtlD) encoded by the cluster is responsible for the formation of the unique lactone-bridged ring and the 16β-hydroxyl of atlantinone B, and a new terpene cyclase (AtlC) can unprecedentedly accept the demethylated ...
Bo-wen Qi +11 more
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The chemistry and biology of fungal meroterpenoids (2009–2019)
Organic & Biomolecular Chemistry, 2021The structural features, biological activities, and fungal biodiversity of 1585 new meroterpenoids were comprehensively overviewed (2009–2019).
Minghua Jiang +3 more
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Unusual chemistries in fungal meroterpenoid biosynthesis
Current Opinion in Chemical Biology, 2016Meroterpenoids are polyketide and terpenoid hybrid natural products with remarkable biological activities. Recent progress in fungal meroterpenoid biosynthesis has revealed several unusual enzyme reactions and novel enzymes, including unique terpene cyclization reactions by a novel family of membrane-bound terpene cyclases and post-cyclization ...
Yudai, Matsuda +3 more
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Meroterpenoid enantiomers from Ganoderma sinensis
Fitoterapia, 2016Zizhines A-F (1-6), six pairs of new meroterpenoid enantiomers and a known meroterpenoid (7) were isolated from the fruiting bodies of Ganoderma sinensis. The structures and absolute configurations of the new substances were assigned by spectroscopic and computational methods.
Wen-Wen, Cao +3 more
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Racemic meroterpenoids from Ganoderma cochlear
Fitoterapia, 2018Ganoderma cochlear, as edible and medicinal fungus, has long been used to prevent and treat various diseases. As our continuously phytochemical investigation of this fungus, a HPLC-UV-guided method led to the isolation of nine previously undescribed aromatic meroterpenoids with different ring systems, including six pairs of racemates, (±)-cochlearins A-
Xingrong, Peng +7 more
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Cannabinoid-like meroterpenoids from Peperomia incana
Phytochemistry, 2023Ten previously undescribed metabolites were isolated from Peperomia incana (Haw.) A. Dietr. (Piperaceae), among which four contained a chromene moiety, two were identified as meroterpene lactones, and four were cannabinoid-like compounds. While the chemical structures of the compounds were assigned based on HRESIMS and 1D and 2D-NMR spectra analyses ...
Hamed, Abdelaaty +10 more
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Cellular and biochemical antileukemic mechanisms of the meroterpenoid Oncocalyxone A
Journal of Toxicology and Environmental Health, Part A, 2020Oncocalyxone A, a 1,4-benzoquinone derived from Cordia oncocalyx, exhibits anti-inflammatory, antimicrobial and antidiabetic properties. The aim of this study was to (1) examine the cytotoxic actions of oncocalyxone A on human normal and tumor cell lines and (2) determine mechanistic actions underlying effects upon leukemia cells using cellular and ...
Aline Borba Sbardelotto +8 more
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